Betty Pearl's Sissy Stories 20.1
Menu => Active Sissy Stories => Topic started by: sissyboy1212 on May 31, 2020, 12:42:25 PM
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Hi I've been toying around with a story idea for a while. Will add more as I get time.
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PART 1
“Josh take out the trash before you leave! I’ve already asked you twice and I’m not asking again!” As the 15-year old raced out the door to meet his delinquent friends and pretended not to hear her, Gwendolyn Hartley sighed. Josh’s behavior had increasingly become a problem and as a single mother she felt frustrated that she had not been able to correct it. After an ugly divorce, her husband had run off with his secretary and had been a non-factor in raising the children although she had taken him to the cleaners in the settlement.
Two years after the divorce, when Josh was ten, Her ex was killed in a car accident while he was driving drunk (again) and had careened off the road into an unforgiving tree. Although the love had long been lost, Gwendolyn had grieved for him and never spoke badly of him in front of her children. She had moved on, but she was saddened by the way he had wasted the latter part of his life.
As for Josh, she had tried taking his allowance and taking away privileges, but he seemed to revert right back after a short time. His grades had dropped and this new group of "friends" had not been a good influence. They weren't engaged in school activities or events and their main pastime seemed to be just lazing around and making sarcastic comments.
Last week she had gotten a call from school that Josh had two days detention after smarting off to a teacher, and on Saturday she had definitely smelled cigarette smoke on his clothes when he came back from hanging out with his no-good buddies. His dress had gotten increasingly sloppy despite the nice clothes she bought for him. The neat polo shirts hung nearly untouched in the closet while he wore the same old ratty jeans and faded (often dirty) tee shirts. Last week, she had given him money with instructions for a haircut but he had blown it on a video game or some other nonsense instead. She had been furious. As a result, his light brown hair was now getting long and it was always mussed hanging over his ears and eyes. She was sure he thought it made him look "cool" in front of those friends.
Why couldn’t he be more responsible like Kathy, his 12-year old sister? She certainly did not want him following in his father’s footsteps.
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Sissyboy1212, you have got to continue this story soon. Now that we have the information about this delinquent young boy, we need to know what is going to happen. I am sure that his sister, Kathy, will be in on all of the consequences that he will have to face. I can't wait for the next episode.
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Sissyboy1212,
That's a good start to your story.
It could certainly take a number of directions. Based on the contents in the first section, I'm going to make a guess or two.
Josh and his delinquent "friends" do something which results in Josh being the only one caught mugging a woman to get cigarette/beer money. The mugging victim is the daughter of a prominent judge, and the assault and robbery charges could send him to adult prison for at least 10 years unless his mother agrees instead to have him committed to a residential rehab school to teach him to respect females by having him dress and act like a female for at least 2 years while being taught basic academic subjects for a high school diploma in addition secretarial, domestic, and cosmetology skills.
That long light brown hair is going to grow a lot longer and he will have to do his own hair and makeup to meet his schooling requirements.
If he messes up in female rehab school, it will be right to adult mens prison general population still in dresses and makeup.
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I have something a little less harsh in mind than some of the stories on here, but rest assured young master Josh will get his comeuppance. A bit more setting up to do first.
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PART 2
“Hi Mom, it’s OK I’ll take it out for you,” Kathy said as she bounced into the room. Good grades, nice friends and well-adjusted at home, Kathy was almost the exact opposite of Josh. She was involved in activities at school and was progressing nicely with her dance classes. Josh too had been so much better behaved just 18 months ago, but that was before these new “cool” friends. His mother knew that part of Josh’s acting out was inevitable due to normal adolescence, but she worried that it was getting beyond the usual boundary-pushing. She also worried about the example he was setting for Kathy, but thankfully there were no signs so far that she was following her brother’s lead. If anything, she was much more mature and seemed happier and more stable. Again, Gwendolyn wondered what it would take to get Josh to be more like his sister.
As she watched Kathy walk out the door with the bag of garbage, Gwendolyn was struck by how much her daughter had grown. While Josh was on the shorter side and the teen growth spurt had not really kicked in, Kathy was shooting up and now she and her brother were nearly the same height at about 5’2”. Kathy already showed every indication of being tall like her mother who stood at almost six feet. While Kathy was prone to be a girly-girl at times she was also athletic and graceful. Dance and other physical activities like gymnastics came easy to her. Josh’s father had been a petite man of 5’7”, and Josh showed every indication of inheriting those genes. Josh had so far exhibited no interest in sports and was frankly sort of scrawny and soft. No wonder he was so easily influenced by those other kids. Gwendolyn feared that Josh had other bad traits from his father lurking in his genes. As she realized how similar her children were physically (for now) but so different in their demeanor, a vague idea crossed her mind. Perhaps she could get Josh to… follow his sister’s lead?
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Following his sister's lead sounds very exciting!
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Sissyboy1212, you are doing a good job of keeping this story interesting. Now, we will see how he follows in his sister's footsteps. Me thinks something is afoot here. Let's see the next installment in this story.
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I really like it so far. There's nothing more adorable than a rude boy being turned into a cute little sister.
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Thank you all for the kind comments. I like writing but I am sort of sporadic. I don't like feeling as if it's a chore but something fun to do when I'm in the mood. I have a fairly specific idea for where poor Josh is going to find himself... I'm just figuring out the best way to get him there :)
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PART 3
The children’s spring break was next week, and Gwendolyn had planned to take them to a friend’s beach house at a sleepy little beach town several hours away. This was not a tourist trap destination with lots of attractions. It had more of a small town vibe favored by locals and people who wanted a quiet time. In fact, the beach house was not really a vacation house at all but more of a second home. Mrs. Meriweather, an old family friend who was recently widowed and a retired school teacher, had insisted they use it for free.
Mrs. Meriweather had described it thusly: “It’s a bit dated but we always kept it like a proper home with extra clothes and personal things there to make it homey. It was never rented out to strangers but we let friends use it from time to time. We used to summer there before Robert got sick. Now that the girls are older, they still love to visit, but it sits empty more than I would like. Please enjoy it and make yourself at home.”
The little coastal town where it was located was almost a flashback in time with a 50s-style soda shop on the short Main Street along with several local shops and even a tidy little community theater where they held town halls, school concerts, pageants, weddings and the like. Gwendolyn was looking forward to the break and a new environment for the kids.
Kathy, of course, was excited for the vacation, but Josh had been moping as usual about not being to hang with his “buds” and bemoaning the fact that there would be nothing to do. “They don’t even have a movie theater or amusement park!” was just one of his many complaints.
On Thursday, as Gwendolyn was packing things for the trip, the phone rang. It was the school again. Josh and his friends had been throwing rocks at recess and broke a window in the gym. He had detention again today and Friday, and the principal warned that his next offense would risk suspension or worse. This was getting serious.
After she hung up, Gwendolyn thought about how she would handle Josh when she picked him up from school. She looked at some of the things she was preparing for the trip and in that moment she decided it was time for more drastic measures. Feeling a sudden rush of excitement as she formed the outlines of a plan, she realized she would need to move quickly and run some errands to put it into motion.
They were leaving Saturday morning for the beach, and she had to put some things in place. First though… a sanity check.
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Sissyboy1212, You give us just enough story to hook us on each segment and then we have to wait until the next segment is posted. You are killing us Sissyboy1212. We love the story and can't wait for more. Hee Hee Hee.
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I'm really sort of surprised at the poll I posted with this story. I find it amazing that there have been over 1200 views of this thread but only 34 bothered to vote (I set it up so even guests can vote and one of the 34 was me -- Hee Hee). I would kindly encourage everyone to engage a little more with this awesome resource. It won't hurt much I promise :)
For those who have posted encouraging comments so far (Andlat, CuddleBunns, dolly bo peep, Sissy Little Girl) and to all the others who contribute. Please know I am grateful for your comments and read every word. Hugs!
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PART 4
Gwendolyn called her sister Karen who was also a divorcee (although with no children of her own). She started the conversation with a question: “Am I crazy, but I’ve been thinking…” As she shared her ideas, Karen was thoughtful at first. Karen was a very proper and no-nonsense woman who was well acquainted with Josh’s budding delinquency.
When Karen had a moment to think it through, however, she chuckled out loud and said she’d be happy to help any way she could. “It will be a pleasure to make sure he doesn’t turn out like his father! I didn’t realize you were open to something like that. You certainly wouldn’t be the first worried mother to turn to unconventional discipline.”
The two women chatted for a while, at times giddily, and Karen agreed to watch the house while they were on vacation. She was also all too happy to assist with “the arrangements”. As they said goodbye, Karen offered a word of caution: “Remember it’s best to rip the Band-Aid off cleanly… no half-measures!”
Later that afternoon after some shopping, Gwendolyn arrived at the school to retrieve her errant son as required by school policy. Josh, expecting to get a tongue lashing or worse, was surprised and a little unnerved to find his mother in a good mood. “Aren’t you mad?” he finally got up the courage to ask.
“Oh honey, of course I’m disappointed in you and you’re grounded," she replied almost gaily. "No TV or internet except for homework for three weeks. No going out with those horrible friends of yours. But I love you, Joshua, and we are going to get you back on the right track.” Josh was uneasy at how casually she seemed to be taking all this but said nothing else. Her use of his full name was an indicator he had long known about that his mother was serious. The evening passed mostly uneventfully. Josh had been quietly hoping that part of his “punishment” would include canceling the crummy trip to that boring beach town, but Gwendolyn assured him that it was still on.
“I think some extra family time together will do us all some good, and why would I punish Kathy for YOUR misbehavior? Be sure and pack your suitcase honey!”
Kathy chimed in, “Oh Joshy we are going to have such fun together!” She was truly excited and couldn’t stop going on about it. “We can swim and play and have ice cream… Just you and me like when we were younger!”
“Great,” Josh mumbled. He didn't even complain about her calling him "Joshy" like when she was a toddler. Something about this situation was gnawing at him. It wasn't quite right. His mother was acting… different.
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Sissyboy1212,
I responded to your poll.
You are doing a good job of building up suspense.
Will Josh pack his own suitcase? If he actually does (most likely his preferred grubby t shirts and jeans) will something happen to them? Will his wardrobe be limited to what Mother brings or what happens to be in the beach house that fits?
Will Josh's time at the beach town be spent as big brother Joshua, or possibly big sister Jessica?
We are eager to see what you reveal in your next chapter.
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Sissyboy1212, It sounds like Joshy is in deep doo-doo. He just doesn't know the extent of it yet. Hopefully, he will make a pretty little girl. So, keep going because you have us on the edge of our seats.
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Sissyboy1212, I really enjoy the setup you've introduced here so far. It sounds like Josh's mother is going to get lots of help punishing him. I can't wait to see where this goes in the future.
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Cue the suspenseful music, bring in the fake suitcase or forget the suitcase Josh packs, pack the ultra-feminine girly clothes for Josh and hide in the car before they leave, remove all means for Josh to communicate with others and bring on the "vacation". Hardly seems like it's going to be a vacation for Josh but he seems bent on pushing things to the limit. Maybe in the future he'll listen to his gut to be wary of his mother and be on the defensive. If he was thinking, he would be doing some snooping and eavesdropping for better intelligence. After all, he's 15 so he should not be completely obtuse or one would hope. Doubt he would ever suspect what awaits him but he might secret away in the car an escape bag to allow him to flee at any unforeseen eventuality. Would love it if his suitcase, with his clothes, came along as a tease that maybe he can escape his punishment.
Excellent story so far (plausible, realistic and suspenseful), Sissyboy1212. Thanks for taking the time and effort.
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Thank you all. I've realized that there is a lot of "build up" here. I didn't really plan it, but it's just turning out that way. But let's not kid ourselves, we all know where this is headed ;D LOL. You will just have to judge if the wait was worth it.
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sissyboy1212, the wait is always worth it with your story. I can't wait for the next part of your story. There are going to be some real changes in store.
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PART 5
Saturday morning arrived and they all chipped in to pack the car. Of course, it seemed as if little perfect Kathy had packed her pink suitcase a week in advance. Josh had thrown a few raggedy tee shirts, underwear and socks in his overnight bag at the last minute and figured that would be fine. He wasn’t trying to impress any “posers” on this loser trip. He actually thought he had been somewhat responsible by remembering to throw in his toothbrush.
Josh had cleverly hidden half a pack of cigarettes in his undies. He figured he would at least be able to sneak onto the beach to smoke one or two. Although he really didn’t like them (yet), he thought cigarettes would make him look cool in front of his friends and was trying to learn this subversive habit to impress them. His mother seemed to have already forgotten his trouble last week, and he decided he was in the clear. Since there seemed to be no further repercussions from his latest detention, he assumed it was over and his uneasiness vanished. He’d complain a bit but serve out his rather light punishment. Then he’d be right back to his old ways. He was already thinking of new ways to get around his mother. “Lucky for me, it looks like she’s a pushover,” he thought to himself.
It was an unseasonably warm day (thanks global warming!), and despite the A/C they were all pretty hot and tired when they arrived at Mrs. Meriweather’s house. Kathy and his mother seemed to chat endlessly on the way about all the things they were looking forward to. Everytime they tried to draw Josh into the conversation, he would mumble out a one or two word answer, and he generally acted annoyed with the whole venture. They had stopped on the way for lunch, and so it was already early afternoon. Josh had expected something like a beach house, but this place looked more like a Victorian grandmother’s place: Doilies on all the furniture, elaborate ball and claw furniture, a formal sitting room, and plush carpeting.
After the exhausting trip, Josh’s mother told them it was best to get cleaned up and refreshed before dinner. Josh, relieved to be free of the car, bolted straight to the shower. “Joshua your room is to the right,” he heard his mother call. He figured his mother and sister could unload the car… not his problem. While he was in the shower, he thought he heard the door open, but when he called out no one answered. Must have been his imagination. Josh was annoyed that the soap and shampoo in the place left a sweet, heavy strawberry scent.
He turned off the shower, wrapped the flimsy towel around his waist and strutted into the adjoining bedroom. God, how had he not noticed what a horror this room was? It had obviously been furnished for a girl. He decided he would have to trade rooms with Kathy. She would love this one anyway.
An elaborate white wooden dresser stood next to the wall, and an old painting of a graceful ballerina hung near it. The floor was dark hardwood with a plush pink and white rug. Wispy pink curtains hung at the large windows, and there was a little vanity table with a big mirror next to the wall. The table was accompanied by a dainty swivel stool covered in pink fabric, and a fancy music box sat on top of the dresser. There was a plush sitting chair by the window also covered in pink. Several antique dolls wearing elaborate dresses sat on a decorative bench between the two big windows. Another antique, full-length oval mirror stood by the double closet doors. The white four-post canopy bed was bedecked with a frilly pink bedspread and several fluffy pink pillows. A sheer, gauze-like curtain hung down from above the bed with tiny pink ribbons and bows woven into its delicate fabric. Finally, laid out on the ultra-feminine bedspread, he realized there were two very different sets of clothing neatly arrayed before him.
None of these clothes were his. Obviously, his crazy mother had gotten things mixed up. As the confused boy took in his surroundings, he realized the bag he had packed was nowhere to be found. It then dawned on him that even the clothes he had worn on the trip -- the ones he had carelessly tossed on the floor a few minutes before -- were also gone. Even his underwear.
Still feeling a little coc-ky, he called out rather rudely “Mom, where are my clothes? These are Kathy’s… or at least some of them are anyway!”
After a moment, the heavy wooden door opened and Gwendolyn Hartley strode calmly into the ornate bedroom. She slowly turned and locked the door behind her with an old timey key attached to a delicate chain. With an ominous click, she removed the key, hung the chain around her neck and tucked the key into her blouse. Then, she purposefully marched across the room and sat in the formal sitting chair. Slowly crossing her legs, she drilled her eyes purposefully into her son’s. Her blue eyes seemed to fully appraise him in a new light. Standing before his mother in only his bath towel, Josh’s bravado melted like ice cream on a summer day. He had never seen her like this.
After an uncomfortably long silence, she spoke in a calm but firm tone.
“Joshua, we will now discuss your future.”
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Wow, sissyboy1212, I am loving the level of description you are putting into the story. It makes me feel like I'm really there. I can't wait to find out what Josh's new life will entail.
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sissyboy1212, you are killing me. I was hoping mom would at least say something to Josh about his new wardrobe. Somehow, I think he is going to be a very pretty little sister.
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Thank you again for the comments. Sissy Little Girl, hee hee. Sorry, I really don't enjoy stories that have no enjoyable setup at all but just jump right in such as "Danny was a bad boy so his Mommy decided he would be a girl now and made him wear a pretty pink poofy dress. He was so embarrassed. The End."
Maybe I'm going too far the other way, but I appreciate you all the same ;D
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PART 6
The teenage boy looked at his mother with a mixture of trepidation and confusion. “What do you mean… my future?” he managed to gulp out in a quiet voice. Standing nearly naked in front of his mother this way was intensely unsettling. The Hartleys had always been more private as a family about such things. He suddenly could not decide what to do with his hands other than cling tightly to his towel. He was self-conscious about where he should be looking. First at his mother… then the floor… the wall… the floor again… the door… back to his mother… the floor again. Why couldn’t he find the right place for his hands? He felt his face redden and heart start beating faster. Worst of all, he was horrified to realize he was falling victim to that common spontaneous affliction of teenage boys everywhere, and his “little man” was showing up at the worst possible time.
“Joshua, you’ve been on a bad path for some months now. Your grades have dropped. You are misbehaving. Those people you hang out with are not your friends, and they are a bad influence on you. The habits you are forming now will be with you for the rest of your life.”
She paused and bored into him with those eyes again, and she softened for a moment. “Honey, I love you too much to let you fall off the cliff. I lost your father years before the divorce and his death. I can’t… I won’t… lose you too.”
“I love you Joshua,” she said again. It was obvious she expected a response.
“I love you too,” the shamed boy said quietly.
His mother’s eyes hardened again and she continued, “So this is what’s going to happen. I’ve made arrangements with your school and you are not returning to school after spring break. You need a change in your environment. I had a long talk with your principal, and in the end she was in full agreement that helping you make better choices right now was more important than a little more math and English. There are only six weeks left until summer anyway, so you won’t miss much if you return to school in the fall.
Josh’s mind was reeling. This was too much too fast. But at that last bit he managed to mumble the question, “Wh… What… What do you mean IF I go back?” He didn’t love his school, but the notion that it was being taken away from him, perhaps permanently, made him start sweating even more.
“Well Joshua, the whole point of this is to teach you to make better choices,” his mother replied ominously. “That was a very good question, and it brings us right to your first important choice.”
Uncrossing her legs and standing, Gwendolyn gestured toward the bed. “You obviously noticed the clothing on the bed: Two paths. These represent your first choice.”
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sissyboy1212,
I'm catching up and really like the way you are building things up.
Now Josh has to pick his poison - which set of clothes will he choose?
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sissyboy1212, another great chapter with lots of conundrums. No school for the rest of the year. Maybe no school in the fall. And now, a change of clothes. I don't know if Josh know what's up from what's down. Let's get another chapter of this fantastic story. :D
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PART 7
Josh’s eyes darted to the set of crisply folded clothing nearest to him. “Ah yes, that is the official athletic uniform of Sterncourt Military Academy for Boys,” his mother began. “It’s one of the highest rated military boarding schools on the East Coast. I’ve put the brochure right there with the uniform.”
On the bed before the red-faced teen lay a plain gray tee shirt with the single word “Sterncourt” emblazoned in black block letters on the front. Next to it was a set of navy blue athletic shorts with the same “Sterncourt” logo in white letters on the right leg. Next to that lay a pair of plain, white, canvas athletic shoes with a single black stripe and a pair of plain white cotton crew-length athletic socks.
“Look at the brochure,” his mother encouraged, “You could soon be one of those boys.” The poor boy’s mind was swirling. On the front, he read the subtitle “Molding Boys into Men Since 1924.” Shuddering a bit, he saw color photos of athletic boys sporting buzz cuts and doing calisthenics, marching in formation, and sitting attentively in austere classrooms. Words and phrases like “disciplined,” “rigorous,” “no-nonsense,” “demanding,” “strenuous,” “compulsory,” “highly regimented” and “strong code of peer accountability” jumped off the pages at him. Josh read with increasing concern that “Every minute of a cadet’s day is carefully structured and strictly supervised to ensure he remains on track physically, academically and socially. Cadets are required to participate in daily morning and evening inspections. Night and weekend group study halls are mandatory and monitored. All boys will participate in one or more contact sports such as football, wrestling or boxing. While parent visits are permitted at any time, we encourage a certain degree of family distance in the first year to let the Sterncourt mindset fully take hold.”
Finally, in a tiny footnote on the last page, Josh paled as he read the following disclaimer: “Corporal punishment is an integral part of the ‘Sterncourt Way’ to instill discipline. While administered only as a last resort, Sterncourt incorporates firm paddling into its program of corrective rehabilitation for infractions as necessary. To that end, a signed parental consent form for corporal punishment must accompany all applications for enrollment. For the safety and protection of students and faculty, paddlings are always witnessed by at least three faculty members and two senior members of the student council. In practice, these are typically executed in full view of the offending cadet’s platoon, and Saturday afternoons have become known colloquially as ‘Paddling Time.’ Please refer any additional questions on this topic to an administrator.”
Josh was already undersized and puny for his age. He had very soft and fine features and so far had not developed the muscles of many of his peers. He had never shown any athletic skill or inclination. He felt without a doubt that he would get eaten alive in a place like that. He had enough trouble fitting in with the boys at his current school. He couldn’t even get his brain to process the idea of being trapped somewhere like Sterncourt.
His mother interrupted his thoughts. “I spoke to the admissions director of Sterncourt yesterday. They will be happy to take you as a transfer student, and they are quite used to taking in new students mid-term for a variety of reasons. They said you would be placed in a special ‘catch-up’ program until the summer to learn your military drills and work on your physical fitness. When the other boys go home for the summer, you would stay for their intensive summer program to get you caught up with your classmates for the fall. Although it’s true they had some problems with hazing several years ago, the admissions director has assured me that is no longer a problem at Sterncourt.”
His mother went on, “The admissions director explained their process to me. The school handbook expressly forbids hazing. Any boy who reports being hazed is immediately removed to a special protective barracks while the school administration investigates. This usually takes two or three days. Afterwards, all the other boys in his dorm are re-educated and tested on the hazing policy to ensure they understand it. If anyone is found to be guilty of hazing another boy, they are given detention for at least three days at the first offense. Only then is the victim safely returned to his peers, secure in the knowledge that they have well learned their lesson. The school is very confident this works since no boy has ever reported a second hazing incident after they put this system in place.”
Josh cringed, and he was absolutely horrified by what she said next.
“If we leave this afternoon, we can be there by six o’clock. The admissions paperwork is already filled out, and they can receive you into a group dormitory tonight. If you so choose, you will wake up at dawn tomorrow morning in a bunk bed to start your first day at Sterncourt.”
“It could be a great opportunity for you,” his mother concluded seriously.
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sissysissyboy1212 boy1212, WOW!!!! I know there has to be another part to this. Not sure what it can be; but, I can't wait for the next chapter to arrive. I'm sitting on the edge of my highchair anxiously waiting to find out what happens next. :D :D :D :D :D :D :D :D :D
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Thank you Sissy Little Girl ;)
I already know where Joshy is going to wind up, and I have a rough idea of how he gets there, but the journey is still a little mysterious right now to me as well.
Glad you enjoy and thank you. Hugs!
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sissyboy1212,
I really enjoyed the last chapter.
You are doing an excellent job in building the tension while we do have a good idea of where this is leading. I liked the detailed description of what would await at the military boarding school.
A lot of us are anticipating the delicious details of the alternate choice.
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PART 8
“But of course, there is the alternative,” she continued. Looking him in the eye she added, “To be absolutely clear, this is all your choice.”
Josh looked forlornly at the second set of clothes. They had to belong to his sister, but as he looked at them more closely, he was crestfallen to realize they would almost certainly fit him. Between his late development and his sister’s accelerated maturity, he had been dismayed for a while now that she was taller than him despite being three years younger. (Every time this was pointed out, he inevitably turned bright red and sulked.)
“I’ll admit this choice is a little less… pre-determined… than going off to Sterncourt. It would truly be a bit of an adventure we would take together as a family without knowing exactly where we wind up. But the world as you know it will be turned a little on its side,” she added with the barest hint of a mischievous grin.
“The basic idea would be to help you rediscover your inner goodness. Kathy is younger than you, but she is more mature. The idea would be for some of her maturity to rub off on you. But to get there, we have to give you a behavior re-boot, so to speak. I thought this was pretty out there, but after talking to your Aunt Karen, I found out there are more families who’ve tried this type of thing then you might imagine.”
“To be blunt, you would basically turn to a more feminine way of life for a while to bring out the softer and kinder parts of you. A key part of that will be dressing the part. It doesn’t matter to me if you want to truly be a girl or just be a boy who likes girly things. The clothes and dress are an important part of making a clean break with your ruinous ways.”
“I’ll admit, the thought of having two daughters, or even one daughter and one sweet son who loves girly things appeals to me. It will be a little harder for all of us, but I’m willing to do it for your sake,” she said to the petrified teen.
His mother’s statement hung in the air for an uncomfortably long time. Josh felt lightheaded as if he were in a bad dream.
His thoughts ran wild and were completely scattered. “This can’t be happening… does she mean to make me a girl? I’m a teenage boy! I’ll be miserable if I have to go to that military school… but I’m a BOY! I’m not some sissy girl.” In a final fit of resistance, the panicked boy blurted out, “This is stupid! I won’t do it! Where are my normal clothes!?!”
With sudden speed, Gwendolyn Hartley stepped forward and grabbed her son by the arm. “Joshua Cassidy Hartley! I’m trying to save you from yourself and you will do this!” she said sternly. He had barely registered the fact that she used his full name (which she only did when she was really upset) when, shocking her son completely, she sat on the side of the bed, yanked him over her knee and began swatting his behind.
As he received the first spanking he could remember since he was a toddler, the teenaged boy was distraught. Truthfully, the spanking was not delivered with much force at all, but the emotional impact of the unexpected turn of events pushed the boy over the edge. Embarrassed and confused, he suddenly burst into tears surprising them both. After only 5 or 6 swats, his mother stood the red-faced teen back up.
“I know this is a lot to take in, Joshua, but I am determined to see this through.” She returned immediately to the decision confronting him. “Your old clothes are not here. Either way, you won’t be needing them anymore. These are your options. What will it be?”
Defeated and still sniffling, Josh brushed his hand across the Sterncourt tee shirt. It felt rough and starchy. Hesitating again, his heart sank as he realized how rapidly and unexpectedly this moment of decision had arrived. Noting his reluctance, his mother said, “I was afraid the other option was just too far out there. I’ll make this easier for you. Let's get you ready to drive to Sterncourt.” She exhaled slowly, almost wearily, with an obvious air of disappointment.
“No,” Josh said in a very soft, wavering voice. He could not yet meet his mother’s eyes. Gwendolyn paused, arched her eyebrow and watched him expectantly. After another excruciating silence, he finally looked up at her with a quivering lip. His face still red, Josh couldn’t believe the words that came out of his mouth next. In the same small and childish voice, he said “No… you said I could choose.”
With dread, Josh fixed his gaze on the pair of pink nylon panties lying on the bed. They were an ultra-girly, baby pink color with a hint of satiny sheen. Dainty ruffled white lace frills circled the waistband and elasticized leg openings. The lace was accented with tiny pink satin bows atop the delicate frills.
“What is your choice Joshua?” his mother asked more gently. She softened as she caught a fleeting glimpse of the sweet little boy her son used to be.
Josh opened his mouth slightly but couldn’t speak in reply. He just couldn’t find the words. Instead, with a trembling hand, the chastened teenage boy reached reluctantly for his new panties… and his new life.
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Part 8 is beautifully written and Josh's choice is well-dramatized.
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sissyboy1212, WTG!!!! Josh had a big decision to make. Go to Sterncourt and learn military discipline or dress like a girl and develop his softer, more feminine side. I think Josh is going to love being a girl. Can't wait to read more. 8) 8) 8) 8) 8)
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Thank you both for the lovely comments. Things are heating up for poor Joshy now. I've written a bit ahead and am trying to chart out a lovely little journey for him. Installment writing means you can't go back and change the beginning, so I'm trying to keep in mind where he is headed. Glad you enjoy!
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sissyboy1212, I can't wait for the next chapter. You have me on pins and needles waiting for your next chapter. Thank you for the compliments because we REALLY do love this story. 8) 8) 8) 8) 8) 8) 8)
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PART 9
Incredibly unsettled, Josh turned from his mother, dropped his towel and stepped nervously into the panties. He shivered as he tugged them up his smooth legs. Unlike some of his peers who were proudly sporting new body hair, he had just the barest beginnings of nearly invisible peach fuzz. He shuddered when he pulled his panties slowly into place. They fit snugly against his skin and boy parts. The panties were so silky and smooth… unlike his normal underwear. He was suddenly horrified as his little man reawakened. Reluctantly turning, the sheepish teenaged boy now stood before his mother with his frilly new panties on full display.
Gwendolyn appraised her wayward son with satisfaction as he took those first tentative steps. If this worked as planned, Josh would soon lose his balance and slide irreversibly into a new girly world. She had some extra “pushes” planned to make it certain, of course. To avoid spoiling the moment, she forced herself to remain silent. She discreetly noted, however, the physical reaction that added to her child’s discomfort. She reassured herself that a plan was already in motion to address THAT little problem.
She stole a glance at her watch. Incredibly, they had only been in this house about two hours. My how quickly this had progressed! Her original plan had been to start either in the evening or tomorrow morning. But the opportunity had presented itself when Josh rushed so selfishly into the house to shower, and she took it. Karen’s admonition to avoid “half-measures” was lodged firmly in her brain. “Rip the Band-Aid off cleanly indeed,” she thought with a smile.
In truth, this notion had taken root in Gwendolyn’s mind. Over the course of the last week, this had grown from a half-baked idea to correct her son’s behavior into… something else. The idea of Josh becoming more girlish filled her with happiness. Josh had always been, if not feminine, then at least sensitive. He was never a rough and tumble boy. She felt certain this recent “bad boy” act was not his true nature. She wanted to help him uncover whatever was there. And, she had to admit, she secretly loved the idea of him being feminine and girly, or even sissy. She had always hated the macho crap anyway. With a full heart, she snapped back to the present.
“Oh Joshy don’t you look sweet!” she said softly when she couldn’t hold it any longer. Gwendolyn beamed and spoke, “How do you like your panties sweetheart?”
Josh’s response could not properly be categorized as words. A little squeaky croak was all Gwendolyn could detect. She smiled at him and said gently, “Joshy, we will have to work on your communication skills as we go forward.”
His head spinning, Josh felt he had stepped into an alternate reality. He had just agreed to… what exactly? To be a girl? Or just dress like one? Or be a sissy boy? Or something else in between? But, unbelievably, he had actually chosen this! Maybe military school was a better way? “No,” he finally decided, “whatever this is will be better than Sterncourt.” It seemed to be the least bad choice, but still he had made the choice to pick up those panties… now his panties.
Josh grimaced as he deduced what was supposed to come next. Still reeling, he held his breath and hesitantly reached for the next dainty item. It looked like a bra, but it was much more childish than the ones he knew Kathy wore. He guessed it was some kind of training bra. It matched his girly pink panties and was adorned with the same delicate elasticized frilly lace and tiny bows. They were obviously a matching set. Skinny pink spaghetti straps went over the shoulders and he assumed, correctly, it must go on over his head like a cropped tank top as there was no clasp in the back.
He held it gingerly for a moment as if it might bite him. Gwendolyn spoke carefully, “It’s called a bralette. It’s a sort of first training bra for little girls who haven’t started developing but want to get used to wearing one. You don’t really have a chest at all yet, so I thought this would be perfect for you. Let me help you with your new bralette.”
“My bralette?” he cringed silently. Even the word “bralette” was such a sissy word that it seemed to cause him physical discomfort at just the sound of it. “What a weird word,” he pondered aimlessly. The word “bralette” conveyed a level of girlishness that “bra” alone didn’t approach. With Gwendolyn’s coaxing, he returned to the moment and hesitantly lifted his thin arms up. She deftly slid his new “bralette” over his shoulders and adjusted it onto his bosom. “Chest, dammit,” he thought. “I have a chest not a bosom!” What was happening? Second thoughts crept in. Was this really better than going to a military school?
Gwendolyn fussily adjusted the willowy shoulder straps until they lightly caressed his slender shoulders in just the right way to gain her approval. Further chagrined, Josh gloomily eyed the large pink bow centered on his slim chest. He suspected the material in his bralette must contain some spandex as the silky fabric hugged his skin snugly. He briefly focused on the ruffled lacy trim that now encircled his torso. An electric tingle ran through the cringing 15-year old boy as he stood in his new bra (bralette?) and panty set.
Abruptly, he gasped. For the first time, Josh glimpsed himself in the full-length mirror. He awkwardly stepped toward it. With his long, just-washed hair, smooth skin and delicate build, he was horrified to see that he looked like a tween girl in her (his?) new frilly undergarments. (Pronouns were becoming confusing.) He inhaled another whiff of the strawberry scented shampoo. How had this roller coaster of events come so far and so fast? What had he agreed to? He stood transfixed by his reflection. His heart raced and his feet were glued to the floor. He lost track of time, mesmerized by the red-faced girly-boy staring back at him.
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PART 10
Gwendolyn interrupted her confused son’s thoughts. With a start, Josh realized his mother had drawn close to his side. Lost in his own head, he hadn’t seen her move. Yet she now held a puffy pink clothes hanger. Of course the hanger itself wasn’t the problem… rather it was what the hanger itself held. Josh stared with dismay at the pink and white item he had especially tried to avoid thinking about. The sinking feeling in his tummy told him that the moment he had dreaded most was now at hand.
Inside the world of his mind, putting on this particular garment would effectively shred what little remained of his “bad boy” act. Somewhat irrationally since he was already wearing panties, the flustered teen felt he was standing on a threshold. Until that moment, he somehow thought his normal life could be clawed back. His eyes darted feverishly around the girlish room, but he saw no escape. Worst of all, he had willingly agreed to this. But maybe there was still a way out…
Sensing a rise in his agitation and perhaps a last shadow of resistance, Gwendolyn delivered another nudge. “Remember Joshy, this is your decision. A big part of this will be learning to follow through on your commitments.“ She continued, “Otherwise… “ she let her voice trail off and cast a studied glance at the Sterncourt uniform still beckoning from the bed.
Increasingly caught in a trap of his own design, and knowing where the other path led, Josh’s spirits plummeted. The brief flicker of rebellion vanished, and his eyes dropped back to the floor. He again took painful note of his sissyish bralette and panties.
With a perfectly manicured index finger, Gwendolyn pushed Josh’s chin up until he was forced to study himself in the mirror. With her other hand, she held the hanger under his chin so that the girly garment was draped across the self-conscious teen’s body. “If this is to really work, you must make an honest effort,” she coaxed. “Take a good look honey, and tell me what you want,” she directed. Her words hung in the air for yet another interminable moment.
Josh peered at his reflection and paused. Then, in a downcast tone of surrender, he said simply, “Ok.” It was all he felt he could muster.
“OK what?” she asked, a tad too impatiently. She cautioned herself that this was a critical moment. She took an almost imperceptible breath.
“Josh, you must be clear about what you are asking,” she continued. “I need to make absolutely sure I know what you want to choose.” The possibility of Sterncourt still lingered like a weight on his chest.
During Gwendolyn’s conversations with Karen, they had concluded Josh needed to choose his new life as much as possible. She felt her role was to “help” him reach the correct choices. As Karen had put it, “Maybe it’s like a casino. It’s quite all right if he has a small victory now and then, but in the end the house always wins!” They had both laughed, but that was the plan. Gwendolyn intended to rig this game so the final outcome was never in doubt. A simple “Ok” just would not do.
“Mom…” he started uncertainly before she interrupted him.
“I think ‘Mommy’ is more appropriate now. It will help you break your old habits,” she continued. Although this was phrased as a suggestion, her firm tone made clear what was expected. “And certainly a ‘please’ is always nice too.”
The dejected teen had not called his mother “Mommy” since he was a small child. The moment overwhelmed him and he exhaled with a shudder. Josh’s next words came with little conscious thought, almost as though the girly boy in the mirror was speaking on his own. In a timid voice, Josh stammered, “Mo… Mo… Mommy, will you help me?” he asked, adding “please” as a hasty afterthought.
With a sweet and confident smile, Gwendolyn prodded her unsettled teenage son, “Will I help you what sweetie? Please tell me what it is you want.”
Josh winced. It wasn’t enough that he was doomed to be turned into a sissy. He had to ask for it? Swallowing hard and thoroughly chastened as his cheeks glowed their brightest red yet, he quietly mumbled his next words. “Mommy, will you please help me put on the dress?”
“Nearly there,” his mother thought with glee. She pressed her agonized son again, “Whose dress is it, honey?”
It was finally clear to Josh what she wanted to hear, and he was ready to say nearly anything to get out of this moment. The teenage boy’s next words were music to Gwendolyn’s ears. She would treasure them for years to come:
“Mommy, will you please help me put on my dress?”
Smiling broadly, Gwendolyn replied “Of course, sweetie! You only had to ask!”
The red-faced teen’s knees weakened as blood rushed to his head. Butterflies flew wildly in his stomach and his little man perked up yet again. His emotions swirled.
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sissyboy1212, I love it. Josh will now become a girl and right now, he hates thinking about it. Of course, he hates the thought of Sterncourt even more. I have a feeling that mommy is going to really enjoy Josh's new life. And now, he has to put on the dress. Great job as usual. Keep up the good work.
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Sissyboy1212,
I'm enjoying your story's measured, methodical progression with your description of Josh's thoughts as each step happens.
I'm looking forward to the next steps.
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PART 11
The pink gingham dress stole Josh’s breath. Incredibly sissyish, it was something a little girl would be thrilled to wear. Removing the pink creation from the hanger, his mother went on, “This is a fun little spring/summer dress I just thought would be perfect for your first!” Josh noticed how happy she seemed. He wished desperately that the floor would open a hole for him to fall through, but it was not to be. “It’s perhaps a tad fancier than the average casual dress, but I wanted your first one to be extra special. It will still be fine for everyday wear,” she encouraged. Smiling broadly at him, she added, “Well let’s not waste any more time. Let’s put you in it!”
“This can’t be happening,” Josh fretted to himself. “I’m a fifteen-year old boy, and I’m letting myself get put into a dress!” Standing awkwardly in his bralette and panties, he waited gloomily as his mother carefully removed the gingham dress from the hanger. She excitedly held it open for him. Despondent, he tried to come to grips with the unreal course of events. With a sinking feeling he thought, “I’m going to be turned into a sissy… it’s actually going to happen.” Not only was he going to be sissified, but he had asked for this himself. Specifically and clearly. Although the other option had been awful, nothing could change the reality that he had made his own choice. That was the truth. He stared with dread at the dress which beckoned him.
Although fascinated by her son’s expressions, Gwendolyn was eager to proceed. Her thinking had rapidly come a long way. The hesitation and uncertainty she felt in that first conversation with Karen just days earlier had been replaced with a sense of purpose. She felt elation at the prospect of sissifying her son in order to save him. She nodded expectantly as she gestured for him to step into the garment. Resigned to his fate, the teenage boy took a slow, shaky breath. Then, Josh skittishly stepped into his dress.
Standing there red as a beet, he obeyed his mother’s instructions and slipped his arms into the short puffy sleeves while she pulled them up. The openings were elasticated, and they drew closely around even his slender arms. Josh normally wore old loose fitting tee shirts which hid his skinny build. With chagrin, he saw that the way these sleeves billowed up toward his shoulders would accentuate how delicate and girlish his arms were below.
With a buoyant smile, his mother dramatically whooshed the dress up over his chest and fitted it into place. She couldn’t help but giggle joyfully. Josh, on the other hand, felt his skin crawl. The breezy cotton material floated over his body before settling airily into place. He could feel his dress gliding smoothly against his bralette and panties as intense new sensations assailed him. The dress tickled as it seemed to dance across his legs and groin. He shivered as she began buttoning him up in back. While she methodically fastened the seemingly endless line of buttons, he unhappily realized it would be hard to remove his dress without help. With each button she closed, the dress hugged his slim torso closer and closer. When she finished the last one at the back of his neck, the crisp white collar brushed lightly against his throat just enough to remind him it was there.
Next, his mother first pulled and then cinched something around his waist. As she tied it taut, it belatedly dawned on him that there was a sash tie in back which made the bottom flare out. He deduced from the way she fussed meticulously with the knot that she was tying a bow at the small of his back. “Great,” he thought glumly. He peered down at his poofy skirt. The lacy edge of an attached white tulle petticoat peeked out prissily from under the pink gingham and rustled airily against his skin.
At last, Josh’s back bow was adjusted to Gwendolyn’s liking. Truth be told, she enjoyed this more than she cared to admit. The sight of her helpless son buttoned tightly and securely into his new frock enthralled her. “He won’t be getting out of that easily,” she thought with satisfaction. Observing his facial expressions, she realized he knew it too. She involuntarily licked her lips. To her, his worries and consternation were almost... delicious. She finally spoke again, intentionally compounding his discomfort. With a veneer of helpfulness, she explained, “This dress doesn’t really need the petticoat, but it does add some fun to the look.”
“Fun?” the miserable boy thought, “this is the exact opposite of fun!” But he was growing more docile now. Acceptance was already taking root in the corners of his mind. Although Josh’s conscious brain still loathed every aspect of his transformation, his subconscious was busily at work. Any lingering traces of resistance seemed to be disintegrating quickly. Each tiny movement he made caused his dress to crinkle and tingle across his skin with a cascading effect. His heart fluttered and his cheeks burned as feelings collided inside him: Shame, anxiety, worry, excitement... arousal. What was happening to him?
In a daze, he blinked sheepishly. Meanwhile, Gwendolyn admired her handiwork with undisguised delight.
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sissyboy1212, Josh has now been confronted and dressed in his very first dress. The emotions running thru his head right now are totally opposite of his mom, Gwendolyn. It looks like he is going to become a nice little girl.
Keep up the good work and hurry with the next chapter. PLEASE......
8) 8) 8) 8) 8) 8) 8) 8)
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sissyboy1212,
Like Sissy Little Girl, I enjoyed your last chapter.
I like the pace of your writing, including the delicious details.
Will your next chapter continue with the transformation? What are the best hosiery and shoes to go with that cute gingham dress? Are pigtails and ribbons the obvious choice for his hair? What jewelry/accessories will mommy find appropriate? What input will sister Kathy have?
We are waiting eagerly for your next chapter.
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Thank you both for the sweet comments. The next chapter is mostly written and you will definitely learn more about poor Josh’s transformation. The details are my favorite parts of these stories, so I try to add them in.
The trade off is that the plot moves slowly. Of course it’s a shame that this means Joshy’s discomfort just keeps getting dragged out, but it really can’t be helped. Tsk, Tsk.
Besides, he’s not going anywhere!
And Kathy will make her reappearance soon. Some of her next part is already drafted too.
Hugs!
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sissyboy1212,
Take all the time you need. I absolutely adore your writing style and have been loving the last couple of parts. Don't let anybody pressure you into writing at a pace you're not comfortable with. I think I speak for most of us here when I say I'd rather read a great, detailed story delivered slowly than a sloppy, rushed one. Keep up the great work hun, you're doing great!
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PART 12
Gwendolyn, however, was absolutely thrilled with her son’s sweet and feminine appearance. Fidgeting submissively before her, Josh looked nothing like that misbehaving boy trying to be somebody he wasn’t. Her excitement grew with each new step her son took into girlishness. She realized that seeing him this way only made her want to take it further. She felt more and more sure this was the right path.
Steering the flustered teen back to the full-length antique mirror, her happiness spilled over. “Why you’re as nervous as a cat!” she teased him playfully. “It’s only a dress, darling, and it fits you so nicely!” She continued to gently box him in. “Joshy, you look absolutely precious,” she said gaily. “How does your new dress make you feel, honey?”
Getting a first full view of himself, Josh was shocked at his girlish and delicate image. His mouth fell open at the reflection. His wispy build, long hair and girly dress made him look much younger than fifteen. Seeing that he looked like a girl of nine (or ten at the most) crushed him. Objectively, he knew anyone who saw him would see only a pretty little girl.
His pink gingham dress featured a vintage suspender bib across the chest in front, and the bib was fastened with large white buttons to two wide gingham straps. The straps ran playfully over his slender shoulders to attach in back. A white blouse underneath was sewn to the skirt and bib so it was all one piece. The collar his mother had buttoned earlier was rounded in a very girly way. Finicky pink embroidery adorned the edges of both the dainty collar and his short sleeves. With the back sash tied, his petticoat and skirt poofed out so that the lacy hem ended a few inches above his knees. The final humiliating touch was a cartoonish pink butterfly with a happy smile sewn to the center of his gingham bib. The plush rug seemed to swallow up his petite bare feet. Darling little girl or prissy sissy boy, did it even matter at this point?
His eyes darted to his mother, and he saw she expected an answer to her question. Remembering the earlier ordeal when he first asked for her help with his dress, Josh knew he had to try harder for an acceptable response. He shut his eyes and searched for the right words. As he shifted his weight nervously, Josh’s petticoat rustled and swished, and he smelled the heavy strawberry shampoo again. The elastic sleeves lightly tickled him as they circled his slender arms, and he was conscious of the way his bralette hugged his small chest. He was almost grateful for his petticoat and skirt as they concealed the way his body was responding to all these sensations. He was painfully aware that his panties were poking out underneath all that tulle and lace. Finally opening his eyes, he even managed to force a weak smile.
“Mo- Mommy, I think my new dress is very pretty,” the abashed sissy boy said softly to his mother. “Thank you for helping me put it on,” he added feebly. He fervently hoped that would be good enough. He still couldn’t believe he was saying “Mommy” again.
Savoring every aspect of her son’s new girlishness, Gwendolyn was giddy. She seized the opportunity, however, to push him a bit further. “Oh, Joshy I’m so glad you like it… but how does it make you feel, sweetie? Does it make you FEEL pretty?” she asked eagerly. She ended with a light admonition, “Be honest, darling.”
Josh cringed, but deep down he already knew the answer. Suddenly queasy, he was forced to confront the unavoidable truth. He had seen himself, and it was pointless to lie.
With another weak smile, he replied, “Yes, Mommy. Thank you so much. My new dress makes me feel so pretty.”
Gwendolyn grabbed her sissy son and pulled him close. Embracing him tightly, she kissed him lovingly on the top of his head. He suddenly felt so weak and small next to her, but the warm hug lifted his spirits. “Oh Joshy, I just know you’ve made the right choice!” she gushed, “This is going to be so good for you… for all of us!” Then she added, “I know this is a lot for you to absorb at once, sweetheart, but I’m sure your sister is wondering what’s going on back here.” Smiling sweetly, Gwendolyn concluded, “I think it’s time to show her.”
Caught up in events of the last hour, Josh had almost forgotten about Kathy. This snapped him back immediately. “Oh crap!” he thought.
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I would like to echo CuddleBunns last comment. The slow, careful drawing out of detail, all types of detail, is the best way to capture, and to invoke in the reader, the complexity of emotions that accompanies such yearnings and transformations. Thank you for sharing your writing.
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sissyboy1212, Another Great chapter. Josh is now getting in touch with his feminine side and I think he will really like it. I also like the fact that Josh looks like a 9 or 10 year old girl instead of the 15 year old boy. Keep em coming, sissyboy1212. You've got us hooked.
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Cuddlebunns, sweet baby katie and Sissy Baby Girl,
Thank you for your encouragement and sweet comments. The details have always been the best part for me, and it makes the little sissy in me gush to read your feedback. (The little sissy inside me has always been a 'pleaser' LOL).
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PART 13
A new wave of anxiety washed over him. He dreaded the prospect of Kathy seeing him like this, but he knew it was already decided. He had agreed to this. “No,” he corrected himself sadly, “I ASKED for it.” His next humiliation was unavoidable.
Seeing her son’s renewed unease, Gwendolyn spoke, “This may be confusing for her, but I know she will be supportive once she sees how important this is to you.” Gwendolyn continued teasingly, “Besides, I know you’re excited to show off your pretty dress!” Sweetly twisting the knife and prolonging the inevitable, she finished, “Won’t that be fun, Joshy? I just know Kathy’s going to love it!”
His mother retrieved the key from her bosom and walked purposefully to the bedroom door. She unlocked it with a click and slowly pulled it open. The door creaked softly on its hinges. She locked eyes with her pretty son as an amused smile crept onto her face. Pausing again to relish the moment, she was gratified to see him blushing again. Powerless to stop the chain of events, Josh stood awkwardly as his cheeks warmed up nicely. Fixing her eyes on the flushed teenager, she called out cheerfully for his sister, “Kathy, would you please come into the bedroom with your brother and me? There is something we want to show you.”
Then Josh heard his sister coming down the hall. He tried to brace himself. This was only getting worse.
Unbeknownst to Josh, however, Kathy, already had an idea what this was about. Two days before the trip, Gwendolyn had spoken privately with her daughter. Although Kathy was mature for her age, the drastic changes that Josh might soon undergo would certainly shock her unless she was prepared.
On the first day of Josh’s last suspension, Gwendolyn sat Kathy down at the kitchen table for a serious conversation. Without detailing all the potential plans to correct Josh’s behavior, she made clear that Kathy might soon see some drastic changes in her older brother. “Kathy,” Gwendolyn began, “Your brother is on a destructive path. We are going to try and help him return to the sweet brother you remember and love.”
Kathy didn’t really grasp everything her mother was saying, but she knew enough that she had been worried about her big brother for some time. “Are you saying we are going to make Josh nice again?” she asked. “Yes, dear,” her mother responded. “It’s possible he may have to go away for a little while, but I think it’s more likely he will stay with us. For this to work, I’ll need your help,” she added. “When we go on our beach trip, some unusual things may happen very suddenly and Josh and I will need your help. Can I count on you?”
Kathy thought this over for a second. “Of course Mom. He’s my big brother, and I’ll do anything to help,” she said with determination. “But I’m kind of confused. What’s going on?”
Her mother replied kindly, “Well that’s just it. Sometimes as we get older, we realize that we have things to learn even from people younger than us,” she smiled. “For a time, you might need to think of Josh as, well, your little brother… or perhaps even your little sister. A lot of this will depend on him. Can you do that?” Gwendolyn asked expectantly.
“Little sister?” Kathy asked in surprise. “If it’s going to help Josh, then I will try my best.” Almost as an aside, she crinkled her nose and added, “Did you know he’s been sneaking around smoking cigarettes too?”
“Yes, I think I’ve found all his hiding places and gotten rid of them all,” her mother reassured.
“Thank goodness! But I’m still not sure what all this means?” she continued.
Gwendolyn realized again how remarkably perceptive her daughter was. She had come right back to the central question. She hugged her daughter. Then, she delicately began to explain how some boys decide to be different.
This topic was something Kathy had already been exposed to recently after a gender non-conforming boy had joined Kathy’s class at school. Without saying it directly, Gwendolyn hinted that Josh might be that way too, but he just might not know it yet. She described how she thought the confusion in his head might be making him misbehave, and it was up to them to help him work through it all. As it dawned on Kathy that Josh might be “just like Leslie but he doesn’t know it yet,” she became enamored with the idea. “Leslie is awesome, and he always has the cutest clothes!” she gushed. If it turned out Josh was the same kind of special boy, then she might be able to share outfits with him and do other fun things you just couldn’t do with regular brothers.
Finally, Gwendolyn told Kathy that this would be their secret until they got to the beach. She didn’t want to ruin the surprise for Josh. Gwendolyn felt sure that Kathy would be ready to help when the time came.
And so now, Josh cringed as his little sister entered the bedroom to see his humiliation.
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sissyboy1212, You have pushed a button with me. I wish I would have had a mom that would have made me wear girls clothes. In fact, at one point I needed a striped shirt to wear in a musical. She couldn't find one in the boys department so she checked the girls department where she found one. She took the label out of it and I wore that shirt till it wore out. When I finally transitioned and became my true self, she told me that I probably would have been thrilled to death to have a girls shirt. My mom was very perceptive in regards to me. And I miss her so much. :'( :'( :'( :'( :'( :'( :'(
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Sissy Little Girl, thanks for the nice comment. I am grateful that it struck a chord with you. Although in my story, Josh's mother has done (and will do) manipulative things, I am trying to paint her as a loving (but slightly weird and dysfunctional) mother. As I'm sure people on this board fully get, the actions directed at Josh by his mother and everyone else are inspired by things I'd wish were done to me.
For me, Josh is the hero (and the lucky winner) in the story. He's just not quite figured it out yet LOL. He probably won't anytime soon :)
Thanks again!
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sissyboy1212,
I'm catching up and like Sissy Little Girl, sarahpenguin, and nappy1 enjoying your story.
It looks to me like Joshy is going to be presented as Kathy's little sister and the little beach town where they aren't know seems like an excellent place for him to develop his feminine presentation, and with it more acceptable habits which would carry over if he is ever allowed to go back to being a boy.
If the feminization process hits major snags, the threat of diapers could certainly be used.
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:D Thanks for compliment, sissyboy1212.
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“...inspired by things I wish had been done to me.” Sigh.... Yes. Let that Muse continue to inspire you.
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PART 14
As Kathy bounced in, she was generally prepared for the situation that awaited her. In truth, similar to her mother, she had actually started looking forward to the idea of having a girly brother. It had been very difficult for her not to let anything slip during the car ride. On the trip, she had even daydreamed about outfits that would look cute on him.
She remembered well that when she was a little girl of six or seven, she had occasionally been able to persuade him to play dress up with her. One particular time, she was very sad and upset after her best friend moved away to another city. To cheer her up, Josh agreed to play tea party with Kathy and her dolls if she promised not to tell anyone. After she pleaded with him, he had even put on her pink dance tutu and a sparkly princess tiara from her Halloween costume. With a pair of his mother’s white tights and a Hello Kitty tee shirt that was oversized for her, he had looked great! She had begged him to let her put some lipstick on him, but that was where he drew the line. Still, they’d had a wonderful bonding time, and she treasured the memory. It’s one of the reasons she truly adored her brother. If he would do all that just to make her feel better, she knew he was still good inside. Would she actually get to relive that memory?
Even with all that time to prepare, however, she still gasped when she saw her brother in his dress. She couldn’t believe how cute he looked. He looked just like a girl… and she was thrilled. “Wow!” she exclaimed, “Josh, you look so pretty!” Looking at her mother and then back at her brother, she said innocently, “but why are you dressed like that?”
Gwendolyn spoke so Josh wouldn’t have to, “Kathy, Josh has decided that he wants to explore girl things for a while. He thinks it will help him be a more sensitive and loving brother and son.”
“Is all that true Josh?” Kathy asked incredulously. Even though she had expected something like this, it still felt unreal.
Blushing a deep red, Josh looked at his mother first. Gwendolyn nodded slightly and silently mouthed the words “Tell her!”
Turning nervously to his sister, Josh finally spoke again, “Yes Kathy, it’s true. I’ve asked Mommy to help me. I hope you’ll help me too.” The crazy words seemed to be coming easier to him now. It was almost like he was watching a bad movie.
His use of the word “Mommy” was not lost on his sister, and she remembered the part about her pretending to be the big sister for a while.
Grabbing his hands, Kathy replied instantly, “Of course, Joshy. You’re my brother and I will love helping you. We’re going to have so much fun!” She then hugged him tightly, and tears formed in the corners of Josh’s eyes. He had always loved his sister, and her embrace moved him. “I love your dress,” she told her sissy brother. “Did you pick it out yourself?”
Turning plaintively to his mother, Josh saw the same look that indicated an appropriate answer was required from him. He was beginning to understand this routine by now, and he knew the type of answer that was expected. “Mommy picked it out for me, and I asked her to let me wear it. It makes me feel soooo pretty!” Without thinking, Josh drew out the word “so” in a very childish way. Why did he do that? His throat tightened a bit and a cold bead of sweat ran down the small of his back. What was happening to him?
After allowing a moment for Josh’s statement to sink in, Gwendolyn piped up, “Kathy, I was just thinking that Joshy’s hair needs some attention. Would you like to help?” Almost ecstatic, Kathy nodded vigorously in response.
“Well Joshy, shall we do your hair?” his mother asked. “With that cute dress, your hair is still much too boyish to go with it right now.”
The butterflies in his tummy went crazy again, but he felt powerless. Hating the words, but with less hesitation than before, he replied “Yes please Mommy.” He gave her another forced smile as a single tear finally fell out of the corner of his eye.
Kathy and Gwendolyn exchanged an excited look.
“Kathy dear, there are some packages on the bed in my room. Would you please bring them in here?” Gwendolyn beamed.
As Kathy scampered away, Gwendolyn pointed her son toward the ultra-feminine vanity dresser.
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sissyboy1212, I can't wait for the next chapter. Josh is well on his way to girlhood. Kathy is only too happy to help her brother become the sister she has so missed. Somehow, I bet Josh is going to get pigtails for his new hairdo. That way, he will look much younger than Kathy.
Keep it up, sissyboy1212. You've got a fantastic story going.
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PART 15
Josh’s mother motioned for him to sit on the pink-cushioned stool. As his petticoat rustled and flitted ceaselessly, she showed him how to properly gather his skirt as he sat down and then smooth it out. The lacy hem of his petticoat settled breezily on his bare thighs. Grasping his small hands in hers, Gwendolyn folded them girlishly onto his lap for him. “Just keep them loosely folded like that on your skirt, dear, and your petticoat won’t push up so much. Correcting his posture, she added, “And please sit up straight.” She made some additional adjustments to his hand placement and pushed his knees and feet close together as if he were one of her favorite dolls. “It’s good for you to practice keeping your skirt in place, and this will also help you stop fidgeting so,” she added.
She turned the stool so he faced the mirror and lightly ran her fingers through his longish light brown hair. Humming softly, she picked up a hair brush from the vanity table and began brushing his hair. She occasionally prodded him gently whenever he showed any sign of slouching or allowed his knees to drift apart. Josh could only sit demurely as his mother methodically stripped away another layer of his boyishness.
Returning with the packages, Kathy was again amazed at the vision of girlishness her brother was becoming. As she put the packages on the canopy bed, she noticed for the first time the Sterncourt uniform still lying there. “Mom, what’s this for?” she asked a bit puzzled. Josh perked up at this unpleasant reminder. It provided additional incentive for him to follow through on his decision and commit to this surreal descent into girlishness. He’d made his bed, and he was going to have to lie in it. Even if it was a frilly pink canopy bed.
“Never mind that. I’ll put it away shortly.” Arching her eyebrow pointedly at Josh, Gwendolyn responded, “I don’t think we’re going to need it after all.” This was followed almost immediately by a single word: “Knees,” she admonished Josh as she pushed his knees together again--a little more firmly than before, “you don’t want anyone to see your panties, dear.”
Hearing this, Kathy tried to stifle a giggle. “He’s wearing panties?”
Gwendolyn replied, “Of course, and a little something else.” Continuing to Josh, “tell your sister about your pretty underthings, honey. I know she’s curious and it’s quite all right.”
Seeing no choice, Josh said with little enthusiasm, ”Mommy is talking about my bralette. It’s a pretty pink just like my panties. They are a matching set.” Kathy couldn’t believe her ears to hear her brother talking like this.
Smiling as she returned to Kathy, Gwendolyn asked, “Would you like to finish brushing out his hair?” Kathy nodded eagerly. Gwendolyn handed her the hairbrush and then moved to tend to the packages. Earlier, when Josh had stormed in the door, he hadn’t seemed to notice a number of packages on the doorstep. Gwendolyn had come to appreciate the value of online ordering and express delivery in this modern world.
The sight of her daughter sweetly brushing out her sissified brother’s hair filled her with a warm happy feeling. But then, with a trace of annoyance, she noticed that Josh’s legs were once more hanging sloppily apart. It detracted from the overall girlish image she hoped to achieve. “Knees, Joshua!” she corrected him yet again. Rapidly clapping his knees back together, Josh noted her use of his full first name with unease.
Then Gwendolyn had a clever idea. Grabbing her purse, she retrieved from it a slim, mirrored compact case which contained her cheek cream blush. The circular metal case had a pewter finish and resembled an oversized coin. Bending down, she once again pressed her son’s knees together and slipped the makeup case between them. “Joshy, honey, this little trick will help you remember your modesty. Just keep my makeup case pressed between your knees, and make sure you don’t let it drop,” she directed. He wasn’t certain, but Josh thought he detected the hint of a threat in her closing words. Squeezing his legs together to hold his mother’s cosmetic case in place also caused him to squeeze… other things. With the nervous squeezing against his ever-rustling petticoat, he was chagrined as a predictable physical reaction happened. Reluctant to test his mother’s patience, however, he was careful to keep pressing his legs together. She noted with satisfaction that his legs were finally staying together properly. It really made him look much more feminine.
Throughout all this, Kathy had continued working meticulously but lovingly with Josh’s soft hair. After a few minutes, her gentle brushing, and his focus on holding his mother’s makeup case in place, had put him almost in a trance. The seconds dragged by at an excruciating pace for the aroused teenage boy. He felt so girlish… boys just don’t sit that way. He was so embarrassed, but at the same time he couldn’t deny how strangely pleasant it felt to have his hair so tenderly brushed. Kathy, having gotten out all his tangles, used a comb to experiment this way and that with hairstyles that might suit him best. She finally decided his bangs were long enough to sweep them over to the side of his head. “Joshy, I think if we pull your bangs over like this it will be super cute!” she told her self-conscious brother. “Mom, do you have a hair clip?”
“I’m already ahead of you dear,” Gwendolyn replied with a grin. Setting a pink cardboard box on the vanity dresser, she dramatically lifted its lid. Josh ogled the multicolored array of girls’ hair accessories in the box with dismay. “I saw this starter set online and had them delivered here just for your brother,” she explained helpfully. “Of course I’m sure he’ll be happy to share them with you if there’s one you’d like to try,” she said with a twinkle.
As Josh cringed, his mother read the paper that was packed with the set: “This cute 36-piece pack of hairbows, clips and barrettes has options to match all her outfits and dresses. Great for every day or special occasions! With all these colors she will be the center of attention!” Gwendolyn added, “I think this is the right choice for today.” She lifted a large floppy hairbow fashioned out of pale pink and white gingham. It was at least five inches long and about two inches wide.
“Ooohh pretty!” Kathy cooed. “It matches his dress and it’s going to look darling in his hair. It’s perfect!”
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sissyboy1212,
I enjoyed reading your nicely detailed next steps in Josh's transformation.
Getting used to wearing dresses with petticoats, and modifying his posture will certainly take some effort, in addition to enduring having a feminine hairstyle, with hair clips, barrettes, and ribbons included.
I'm eager to read what happens next.
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sissyboy1212, the detail that you use in your story is amazing. Poor Josh is starting to look like a young girl. I am sure that Kathy and his mom are enjoying this no end. He is also learning deportment from his mom on how to sit like a young girl. The box of hair bows, barrettes and other accessories are a fantastic addition.
I can't wait for the next chapter. :P
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PART 16
With a sinking feeling, Josh sat motionless as Kathy worked a small dollop of styling mousse into his hair to make it “a little more poofy.” Then she gathered his bangs and carefully twisted them together onto the right side of his head. Pulling his hair gently as she teased it into place, she took the prissy gingham bow from Gwendolyn and used its attached alligator clip to secure everything in place. She made a few last adjustments and stepped back to inspect her work. Josh immediately felt the alligator clip exerting a constant light tug on his hair as if to remind him it was there. Studying his reflection, Josh saw that the cutesy hairbow pulled his hair back in a way that framed his face adorably. “I’m such a fairy now,” he said softly to the mirror.
“Sissy, dear. You’re much more of a sissy than a fairy,” Gwendolyn gently interrupted him. This startled Josh as he hadn’t meant to speak out loud. “But you can ask to be a fairy for Halloween if your heart is set on it!” she chuckled lovingly.
This remark brought another fond memory back. “You’ve already sort of done that anyway. Remember when you were twelve you went as Peter Pan? You looked so cute in your little green leotard and that adorable Peter Pan hat!” Even though he had thought he was getting too old for trick or treating, he had agreed to go as Peter Pan because Kathy wanted to be Tinkerbell. She had begged him to go with her. He had to admit it was a great costume… especially after he let his mother put some light makeup on him to add freckles and make his cheeks more rosy. The crowning touch had been a dusting of sparkly glitter makeup to match Kathy’s. It had wound up being more effeminate than he had expected, but it was a lovely time even if a few folks had snickered at his costume. His unguarded reference to a fairy had obviously met with Gwendolyn’s approval. “Don’t you just love your hair like this sweetheart?” she prompted him.
Becoming more accustomed to this ritual, Josh replied, “Yes Mommy I feel so pretty. I just looove the way my hairbow goes with my brown hair. Kathy, thank you so much for doing it for me.” Josh gushed a little more than he truly intended, and for some reason he had stretched out the word “love” very girlishly. God he sounded so sissy-ish.
“Brunette,” Gwendolyn corrected him. “We call girls and girly-boys with brown hair ‘brunettes.’” From the start of this, she had schemed for him to say and repeat girlish and childish words as much as possible. In time, she hoped that it would have a subduing effect and he would talk like a sweet little girl all the time without thinking.
“Thank you Mommy. Of course I meant ‘brunette.’ I really adore my cute gingham hairbow. It goes so well with my… brunette hair,” Josh replied. Gwendolyn noted approvingly that her prodding was already generating the desired effects. Her son’s answers were growing longer and more flowery. Josh had always possessed an excellent vocabulary, although over the last year he had hidden it behind faux-rebellious teenage boy posturing. She was so tired of hearing “yeah” and “uh-huh” from him. And every time she had asked him how his day was and received a sullen “OK” in reply had bothered her to no end. She intended to bring his vocabulary back and make him use it. Especially the sweeter and more refined parts of it.
Kathy bent down and kissed him sweetly on the cheek. “Oh Joshy we are going to have such fun together! It makes me so happy that you’ve decided to do this,” she told him excitedly.
Gwendolyn smiled appreciatively for a moment at her two children. Turning to Kathy, “The other boxes have his new shoes. Would you get them please?” Then she addressed her girlified son, “I couldn’t decide which ones would look the best with that adorable dress, so I have a couple pairs for you to try and choose from. We need to start building your wardrobe anyway. Won’t that be fun, dear?”
“Oh yes Mommy. I’m sure they are all wonderful and I can’t wait to try them on,” he replied almost automatically if still flatly. His weak smile was still forced, but perhaps a little less so.
“Joshy these are both so precious. You’ll have a hard time choosing!” Kathy said gaily.
“Shoes… great,” Josh thought dejectedly, “I’m a brunette, and now I get to try on girls’ shoes. At least I know what’s coming next.” He remained highly conscious of the hairbow’s foreign presence in his hair, and in the mirror he saw it bounced a bit every time he tilted his head. His fine facial features looked very girlish. And of course he continued to carefully press his mother’s cosmetic case between his knees. The throbbing under his skirt had subsided somewhat but it was still there. The little appliqué butterfly on his gingham bib seemed to giggle at his predicament. He was reluctant to risk moving his hands, so they remained folded daintily on his lap. In exquisite agony, the jittery teenaged boy wriggled his bare toes on the plush rug and sighed.
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sissyboy1212, Oh, poor Josh. Inside, he is hating his girlified appearance and when he answers, there is no joy there. I wish I could have had this done to me; but, that didn't happen. I had to wait till I was 44 to become my true self.
Keep up the good work. 8)
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In everyday life there are choices, Josh was at the cross road and given two choices by his mother. Going forward or back was not an option. A great opening to your story. Now the decision is on shoes. In this decision it can be either one or the other, or perhaps both.
Then there is the authors decision. To Continue the story or not. Sissyboy, I hope you decide to continue the story. Please
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Thank you for the kind words and encouragement. I definitely intend to continue this adventure. Life gets in the way of writing sometimes though. There is more to Josh's story, but it will come in time.
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PART 17
As Kathy eagerly brought over the first pair of shoes, their mother retrieved her cosmetic case and then swiveled the feminized boy slightly on the stool to face Kathy. “I’ll take this back while you try on your shoes, but remember your modesty sweetheart,” she cautioned him. Josh was relieved to relax his knees but then he groaned softly as he saw the shoes.
They were a very girlish pair of cute open toe white patent sandals with a low block heel. The sandals had buckle ankle straps with narrow straps that looped gaily across the top of the foot. As Kathy knelt down to strap them on his feet, Josh couldn’t take his eyes off the little white flower applique on top which practically screamed “Girly Girl!” Kathy expertly slid them over his feet and then buckled the shiny white straps snugly around his ankles.
“Well stand up honey and let’s see them on you,” Gwendolyn beamed.
Josh stood up a little unsteadily and took some tentative steps.
“Those are adorable!” Kathy exclaimed. “I just love how strappy and cute they are on your feet. And those flowers on top are just to die for!”
Looking at Josh, Gwendolyn asked “What do you think darling?”
“Oh Mommy,” the sissified boy began almost without thinking, “they are so pretty.” Cringing, he continued, “I just love the little flowers on top.” He hoped that was sufficiently gushy.
“Give us a twirl Josh,” Kathy prodded. Reluctantly and carefully, Josh turned slowly around causing his petticoat and skirt to rustle and swish.
“I agree that those really do complete the outfit,” Gwendolyn agreed. She also noted with satisfaction that the summery sandals fit his small feet perfectly. She had done her homework on sizes before ordering them online. They made his feet look even more delicate and deliciously feminine.
“Should we try the other pair, Mom?” Kathy asked.
“Those really are perfect, but we'll let Josh pick since he's the one who will be wearing them." She then added with a knowing look, "After all this is all his choice."
As the embarrassed boy stood there, Kathy retrieved another pair of sandals. “Those are just as girly as these,” Josh thought glumly. This low-heeled pair was a soft pink with even narrower straps to encircle the foot and ankle very delicately. The straps were dotted with small black polka dots, and Josh counted two, no three, shiny little silver buckles on each. They looked like a nightmare to get into. At least the ones he had on his feet now were white and not pink. Maybe that was something.
“Mommy, if it’s all right I think I will stick with my cute flower sandals,” Josh decided. “I think they go better with my pretty dress,” he added just to be safe.
Gwendolyn eyed her son for a moment, and then smiled warmly. “I agree sugarplum, those white sandals look so precious. You've made a great choice! You will have lots of chances to wear the other ones. Besides, I think it’s getting time for something to eat.”
His mother guided him back again to the full length mirror, so he could take in his completed look. Looking at himself, Josh saw nothing but a pretty little girl staring back. His floppy gingham hairbow was pinned stiffly in his long hair. The bow sash on his pink gingham dress made the petticoat poof out and tickle his legs. His fussy little girl collar was snug around his neck, his strappy flower sandals just completed the sissyish look. Josh couldn’t believe how quickly this had happened to him.
Gwendolyn was overjoyed with her son’s transformation. There was hardly a trace of that rambunctious fifteen year old boy that had barreled through the door a couple of hours ago. “I’ve got some sandwiches in the kitchen. After that, I think it would be nice to stretch our legs and walk into the village.”
Kathy giggled and headed for the kitchen. For a moment, Josh froze. Somehow, up to this point, he had thought that maybe he would just stay in the house. The idea that now he would have to go out in public dressed this way brought a whole new wave of anxiety over him. “Into the village?” he croaked the question.
“Of course, silly,” his mother responded. “You didn’t get all dressed up to stay in the house, did you? It will be a marvelous chance to show off your new dress.”
“No half-measures,” Gwendolyn repeated the mantra happily to herself.
Lightheaded, Josh started taking small mincing steps toward the bedroom door to maintain his balance as he started to get used to his flowery, unfamiliar shoes.
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Just happened to find the perfect picture of Josh's new sandals. Such a lucky little sissy. Tried to post the picture but had no luck so follow the link to see Josh's new shoes. Pictures really are worth a thousand words but will only enhance not replace the excellent work of the authors.
https://www.rackroomshoes.com/p/brittany-sandal/742021?
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Guilty! Those are the inspiration. I saw them online and knew they would be perfect for Joshy! :P
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PART 18
After their meal of sandwiches and chips, Kathy kept asking Josh to twirl around for her. She loved the way his skirt floated so airily around her brother’s waist. While Gwendolyn was clearing things away in the kitchen, Kathy got the idea to teach Josh how to do a curtsy, so they practiced that for a few minutes. At Kathy’s insistence, Josh did a passable curtsy for his mother to her utter delight and his great chagrin. Before the flustered boy knew it, his mother had whipped out her cellphone and taken several pictures.
In short order, Josh was propelled out the door by his mother and Kathy for an early evening stroll into town. It was a short walk in the hot evening weather, but Josh had to walk more carefully than he was used to in his new sandals. With a light breeze blowing, he found that his skirt and petticoat tended to float up occasionally. The frothy tulle danced merrily over his legs as he tried to get used to walking this way.
Gwendolyn loved the sight of her son stepping so daintily, and she reminded him to make sure his dress didn’t blow up and expose his panties. Red-faced, Josh did his best to walk modestly as they moved onto the main street of the little town. Kathy was also dressed girlishly but much more casually in a denim skirt and fashion tee shirt. To anyone watching, she was clearly the older sister. People smiled at the mother and her daughters as they passed. No one seemed to realize Josh was a boy underneath, but that did nothing to ease his discomfort.
As they walked they came upon a quaint little dress shop with fancy dresses and very feminine clothing in the window. There was a sign on the window in elaborate script writing that announced the name “Smyth’s Clothing and Bridal, Bespoke Fashion for Ladies and Children since 1955.”
“Oh my those are lovely, don’t you think?” Gwendolyn looked at the beautiful dresses admiringly. The window display seemed to be nothing but soft pastels, ruffes and gauzy lace. There was only one boys outfit that Josh could see, a fancy little sailor suit that looked like it was meant for a toddler.
“Oh yes,” Kathy agreed, “Can we go in and look around? I’ll bet we could find something nice for you in there Josh. Wouldn’t that be fun?”
Put on the spot, Josh replied, “Oh yes Kathy that would be very nice.” Beet-red, the feminized boy felt trapped. However, a moment later, he finally caught a break as he saw a very well-dressed older lady exiting the door. She appeared to be the shop owner who was closing up for the day.
“Oh dear,” Gwendolyn sighed, “it looks like they are closed. Perhaps another time.” Josh breathed a huge sigh of relief. The last thing he wanted to do right now was look for dresses and girlish clothes. He found himself clinging near his mother as he wished they would move on from the shop quickly. It was such a girlish looking place it felt almost radioactive to him.
Overhearing their conversation, the lady turned to them. “Why what lovely girls! Yes I’m afraid I’m closed for the day, but you are more than welcome to come back next week. I’m Dolores Smyth, and this shop is my little piece of heaven. I’d be happy to help you find something you like,” she said agreeably. “My mother started this business years ago. She was the original ‘Mrs. Smyth.’ I took it over from her twenty years ago and have been running it ever since.”
“Thank you so much, Dolores,” Gwendolyn replied warmly. “I’m Gwendolyn Hartley, and we are here for a little vacation during the kids’ spring break. We’re staying at the house of a friend. Perhaps you know Mrs. Meriweather?”
“Why yes we’re acquainted. She and her girls were customers for years. It’s a pretty small town,” Mrs. Smyth replied.
“You really have some very nice pieces in the display,” Gwendolyn offered as they made small talk. Kathy listened to the conversation with interest as Josh squirmed self-consciously.
“Why thank you Gwendolyn, and are these precious angels your children?” she asked.
“Yes of course,” Gwendolyn answered. “Where are my manners?” Turning to Kathy and Josh, she directed, “Please introduce yourselves to Mrs. Smyth.”
“Hi I’m Kathy,” Kathy introduced herself. “I really like your shop and hope we can come back soon.”
“Thank you dear, you are welcome any time,” Mrs. Smyth responded. “And this must be your younger sister,” she gestured to Josh. Sensing his shyness, she continued, “That’s a lovely gingham dress you are wearing and such a pretty hairbow. What’s your name dear?”
Blushing furiously now, Josh didn’t speak for a moment. Now this lady was going to realize he was a boy. Gwendolyn fixed her gaze pointedly at her sissified son. This was an interesting moment. Finally, after several awkward seconds, he stammered to Mrs. Smyth, “I’m J… I’m Josh.” He immediately dropped his eyes and studied the sidewalk. Knowing that more was expected, he continued awkwardly, “your dresses are very pretty.”
In a moment of surprise and then clarity, Dolores Smyth arched her eyebrow and appraised Josh much more carefully. A different kind of smile appeared at the corners of her mouth and her eyes gleamed. “I see. Josh, is it?” she said, not unkindly. “Well young master Josh you wouldn’t be the first special boy to visit my shop. I’ve helped a few lucky boys find pretty frocks over the years. Why should girls have all the fun? You come back and I promise we will find something scrumptious for you.”
Seeing his mother looking expectantly, Josh knew a reply was required. “thank you very much, Mrs. Smyth. That sounds wonderful.” The expression on his face seemed to say that he didn’t find it wonderful at all, but Mrs. Smyth seemed not to notice.
Gwendolyn nodded approvingly. “We will definitely come back to see you, Dolores, thank you so much.”
Mrs. Smyth replied with a giggle, “it would be my absolute pleasure. I don’t get this chance very often. I think it’s been at least five years since the last one. And he’s lucky to have such a marvelously feminine build.” Mrs. Smyth happily handed Gwendolyn a business card. “How old is he? I’m guessing eleven or twelve perhaps?” Mrs. Smyth asked.
“Josh is fifteen,” Gwendolyn replied knowingly.
This seemed to genuinely shock Mrs. Smyth. “Goodness, most boys his age are not nearly as delicate. I’d never have pegged him as a teenager.” Speaking cheerily to Josh, she added “Indeed you really are an extra special little boy. I can’t wait to get my hands on you, my dear.”
Genuinely worried now, Josh noticed his sister insistently gesturing at him. When it dawned on him what she wanted, Josh looked pleadingly at his mother. Gwendolyn gave her son a piercing look, and he sensed that same edge of firmness in his mother as when she had pushed his knees together earlier. Grimacing slightly, Josh delicately took the hem of his skirt in both hands, placed his right foot behind his left, and performed a wobbly curtsy as he said, “Thank you, Mrs. Smyth.”
Mrs. Smyth was impressed and thrilled with the sweet gesture. Kathy beamed and Gwendolyn nodded approvingly. With that final flourish, they said their goodbyes.
Mortified, Josh didn’t trust himself to speak and his face was hot. He had just curtsied in public like a simpering little girl. Not only was he already exposed as a boy, but now he had a trip back to the dress shop to dread. The breeze lifted his petticoat again and he had to hold it down as he walked. He felt the breeze catch his hairbow too but it was clipped securely in his light brown, or rather his brunette hair. It wasn’t going anywhere. Kathy was excited about the prospect of helping shop for her sissy brother. Gwendolyn hummed happily to herself as they continued their walk. This was really going splendidly.
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sissyboy1212, Josh is in a predicament. Mrs. Smyth knows he is a boy and a delicate one at that. She is going to have tons of fun fitting him in pretty dresses and frocks. I am really enjoying this story. Great job.
:D
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PART 19
The remainder of their evening stroll was mostly uneventful, with people generally smiling at the children and their mother dressed so prettily. They did stop in the old fashioned soda fountain and had some ice cream, which Josh had to admit was nice. The older teenage boy behind the counter grinned at them as he served up their ice cream, and they all sat at a sidewalk table while they ate in full view of passers-by. Gwendolyn asked one of the teenagers working in the shop to take some pictures of them eating the ice cream so she could capture the moment. Josh did his best to smile and look normal. Several passers-by remarked on Josh’s pretty dress, but otherwise thankfully didn’t engage in conversation.
There was one moment where Josh got a little too relaxed while eating and let his knees dangle apart again. When this happened, his mother whispered “Knees!” to him again, and she slipped her makeup case from her purse back between his knees while they sat there. It was a humiliating situation for Josh, but no one but Kathy seemed to notice. As she giggled again, he straightened up his posture at once and sat very sweetly for the rest of the time while they ate. Gwendolyn noticed that her sweet son was taking much more careful and dainty bites--probably due to the fact that he was so self-conscious. She smiled as it was such a contrast from the way he normally gobbled his food.
When they returned to the house, it was dark and they were all tired. Josh began wondering what he would have to sleep in. He held some faint hope that his mother might not have thought about sleepwear, but he was not optimistic. She seemed to have planned for everything else. As Josh thought about how his world had been so upended today, he couldn’t stop coming back to the idea that is was all his choice. Yes, the other option had been truly rotten, but he was still the one who took the panties and put them on. He ASKED for his dress. He picked his shoes. He had even thanked Mrs. Smyth for basically saying how much of a sissy he was, and then he had curtsied of all things. He was exhausted and eager to get out of his dress and these clothes.
Josh didn’t have to wait long as his mother came into the ultra girly room.
“I know today has been a busy day,” she smiled. “I thought I’d help you get undressed and ready for bed. Would you like that honey?”
“Yes Mommy,” he replied eagerly. “I’m so tired.”
She hugged him warmly. “I’m so proud of you my darling. You’ve been brave today, but I feel you made the right decision. You are already so girlish and sweet. I’m happy to be able to help you. Will you do that thing you did for Mrs. Smyth again for me? I want to see it one more time before bed.”
Knowing there was really no choice here, Josh said “Yes Mommy.”
“And you know what it’s called right? It’s important to call things by their proper names,” she prodded.
Sighing, Josh said sweetly, “Yes Mommy of course. It’s called a curtsy. I’ll be happy to do a curtsy for you.”
Gwendolyn loved hearing the sissyish words roll off her son’s tongue, and she was practically giddy to see him dip sweetly for her in another pretty curtsy. “That’s so sweet, dear. You’re getting better with practice,” she encouraged. Gwendolyn fully intended to inject girlishness and femininity into every aspect of her son’s life. “No going back,” she thought to herself. “No half-measures.”
Then she helped him unbuckle his sandals and placed them in his closet. She untied his dress sash and unbuttoned him so he could finally slip his lovely dress off. She then had him neatly hang it in the closet, and she showed him how to fluff it out on the hanger to reduce any wrinkling. She gently removed his hair bow and had him place it carefully on the vanity in his storage box. As he stood again in just his bralette and panties, she told him to go brush his teeth. When he returned, he sighed as he saw that his mother had indeed not overlooked sleepwear after all.
Beaming, she held out his new pajamas to him. “Aren’t these just precious?” she exclaimed. The bottoms were a soft and closely fitted set of thin stretchy leggings. They were white with little pink hearts all over and cuffed high on the ankles with a delicate fringe of tulle. Gwendolyn told him he could pull them on over his panties and sleep like that. He slid them up his slender legs and shivered as they felt a little cool. They weren’t tights, but they fit closely around his legs and were very girlish. His mother helped him lift off his bralette and held out the top to him. The top was a soft pink made of the same stretchy material with a big darker pink heart design on the front. It had short cap sleeves fringed again in tulle, and as he slid it on it clung to his narrow chest. It was cut short and left his belly button exposed so that his heart covered leggings remained in full view.
“Well don’t you look good enough to eat?” Gwendolyn giggled.
Josh didn’t know how to respond to that. He fidgeted awkwardly with his girlish pajama top and tried in vain to pull it down over his tummy.
Then his mother asked him a more direct question, “Joshy sweetie, do you like your new jam-jams?”
“Oh yes Mommy I love them. They are so cute and comfy!” he gushed more enthusiastically than he felt.
“Your Aunt Karen will love to hear that,” Gwendolyn told him. “She helped me pick them out for you.”
This was another unpleasant surprise at the end of the day. “You.. you mean Aunt Karen knows about all this?” he asked tentatively. This was all moving too quickly.
“Yes dear, I was going to tell you later, but we don’t keep secrets from family. She helped me do the planning. I also already sent her some of the pictures of you in your dress. You can call her tomorrow and thank her yourself,” his mother concluded.
Then Kathy came in to say goodnight, and she raved over how cute his jammies were. They both insisted on getting kissed goodnight, something Josh had not done since he was a little boy. Then, Gwendolyn tucked her son into his plush pink canopy bed.
“Goodnight princess,” she teased.
“Good night Mommy,” Josh dutifully replied.
His thoughts swirled. How had he gotten himself in this mess? Despite his consternation, though, he was so tired he soon drifted off into a deep sleep.
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sissyboy1212, Josh really got a crash course in femininity. HIs outfit sounds like it was to die for. I wish I had one like that; but I don't wear dresses anymore unless I go to a funeral or a class reunion. Because I am a m2f, I wear only female clothes now. That's why these stories resonate with me. I wish I could have had these things happen to me when I was kid.
:D
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PART 20
Josh bounced high into the air. He wore an enormous frilly pink petticoat that rustled all around him. His petticoat twinkled in the soft light and seemed to be dusted with a generous helping of shiny glitter. As he started falling, his petticoat whooshed up around his head to expose his elaborately frilled pink and white panties. Tiny specks of glitter flew off it to create a sparkly cloud as he fell. He landed on a huge satiny cushion that seemed to quickly pull him in. It felt like a big pink marshmallow as he sank into it. He also seemed to be encased in a strange type of clingy shirt with no apparent armholes. It pinned his arms tightly to his sides like a big pink stretchy sleeve. He felt his legs being held together somehow too. Once he finally reached the bottom of his fall in the cushion, he was chest deep in its confines. Then, he abruptly shot back out like a rocket high into the air again to repeat the whole process. The cushion was like a springy trampoline which repeatedly launched him back up. It was scary but exhilarating at the same time!
His pulse quickened as he saw a crowd of people laughing and clapping as he shot through the air. He couldn’t quite see their faces. Someone whistled every time his petticoat flew up right before he dropped out of sight again into the spongy cushion. There was a huge lace collar or shawl covering his neck that came all the way up to partially cover his mouth. It tickled him ceaselessly, and it only got worse as his breath quickened. Next, he realized a ridiculously huge pink satin hairbow was pinned securely in his hair. It was at least a foot long, and he could see the ends of it flopping down from the corners of his eyes. Curly pink ribbon streamers with ornate white lace were attached to the hairbow, and they floated playfully all around his face. He caught a glimpse of his ankles and knees as he flipped again in the air. They were wrapped snugly together with a thick pink gingham ribbon. Someone had gone to a lot of trouble to tie it all off into an exquisite bow halfway up his calves. Catching a glimpse of his feet, he was surprised to see that he wasn’t wearing proper shoes. His feet were encased in fuzzy oversized pink cotton balls that were sprinkled with glitter as well.
Again, Josh sprang up and then dropped down for what felt like the hundredth time as his petticoat fluttered airily. The pace was accelerating, and every time he landed he sank a little deeper. He finally saw who was doing the whistling, and it was a couple of teenage boys wearing Sterncourt uniforms, chuckling and hooting every time they saw his panties. Time seemed to freeze for a moment and he saw the taller of the two hold up a huge placard that read “SISSY” in big pink letters. Next, the other boy held up a sign that said “CURTSY” in the same pink lettering. They both cheered loudly, and the taller one winked jauntily at him.
As he shot into the air again, he rose much higher than before and his heart raced. Finally his momentum slowed, and he started to fall again. Faster and faster, he picked up speed as his petticoat flew up wildly. After a seeming eternity, he reached the cushion and sank very deeply into it… the deepest yet. He was nearly breathless as it enveloped him in a satin cocoon. His stomach flipped over and over, and it got much darker. The satin seemed to pulse as it squeezed him tighter and tighter, making him very lightheaded. He heard buzzing in his ears. Suddenly, he shuddered all over and gasped frantically for air…
With a start, Josh woke up.
After several confusing seconds, he remembered where he was as he looked up at the gauzy pink canopy in the morning light. The events of the previous day came crashing back to him. Then, he made an awful discovery. His panties were a sticky wet mess, and his stomach sank as he digested the unpleasant truth. He’d had a wet dream. What was happening to him? He was unnerved by how vivid and powerful the dream was. He needed to clean himself up before anyone found out. Throwing the covers off, he sat up on the edge of his girlish bed in his sissyish heart pajamas, once again taking in the ultra-feminine room.
A moment later, however, Josh realized he was too late as his mother entered the room.
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sissyboy1212, that was some dream. I guess all of this feminization is having an effect on Josh, even when he is sleeping. He had hated the idea of going to Sterncourt and i only seemed plausible that he would include it in his dream. Keep the chapters coming.
8)
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PART 21
“I thought I heard you stirring around in here. Wake up sleepyhead, we have a busy day ahead!” she smiled at him sweetly. “How did you sleep?” she asked her girlified son.
“Fine Mom, uhh Mommy,” Josh remembered belatedly to use the right word. Still disoriented, he timidly tried to cover the obvious wet spot on the front of his heart-covered leggings. This only succeeded in drawing his mother’s attention to it.
Gwendolyn quickly grasped the situation. She didn’t want to focus too much on this since it might backfire and hinder all their progress. It was too risky and also unfair. He was still a teenager after all. Making him ashamed of his body would be counterproductive. She only wanted him to be more feminine, so she had to be cautious. Still, she sensed an opportunity to put this in the proper context. She would persuade but not force. “I see,” she said kindly. “Did someone have a little accident?” she asked gently. “You can tell me.”
His mother’s question hung in the air for several long, agonizing moments. He was already embarrassed, but the way she talked to him like he was a child made it all the worse. Reaching the inevitable conclusion that it was pointless to pretend otherwise, Josh cringed and said, “Yes Mommy.”
“It’s OK,” she soothed him as she lightly stroked his hair. “Little squirties happen sometimes. Is that what happened? Did you have a little squirtie? Tell me please.”
Grimacing, Josh replied slowly, “Yes Mommy. Uhh, do we have to call it that?” he asked tentatively.
“Honey, remember we are trying to break old bad habits,” she explained evenly. “You have nothing to be ashamed of. These things are only natural. But, calling this a “little squirtie” instead of something more crude and vulgar seems more in line with what you are trying to achieve, right?” she questioned.
Hearing her explain it that way, it all made a weird kind of logical sense to Josh. “I guess so,” he finally responded, adding “Mommy” after a moment.
Gwendolyn smiled again, “So can you try again to tell me what happened honey?”
Taking a breath to steel himself, Josh skittishly admitted, “Mommy, I made a little squirtie in my panties while I was sleeping.” Josh could scarcely believe the sissyish words he was using. The scary thing was that speaking this way was sounding more normal to him.
His mother continued, “Don’t worry about it buttercup. Go put your soiled pajamas and panties in the hamper and hop in the shower to clean up. I put some different bath products in there for you last night. You’ll find a loofah sponge and shower gel, moisturizing shampoo and conditioner. Dry yourself off, and use some of the body lotion on the vanity. Then we will figure out what to wear today, OK sweetie?”
“OK Mommy,” Josh said quickly. Relieved to be done with this conversation but now thinking about this elaborate bathing routine, he scampered into the bathroom to strip off his sticky panties and pajamas. As quickly as he could, he started the shower and jumped in, trying to forget the whole episode. He saw a whole row of ladies bath products that were obviously for him.
As he lathered up the shower gel, he detected a delicate floral scent. It was not as strong as the strawberry but even more feminine. While he was washing, he heard the bathroom door open. “I’m just grabbing your dirty things to throw in the laundry,” his mother called. “I’ll lay some fresh clothes out on the bed for you,” she added.
“Great,” Josh mumbled to himself as he continued with his bath regimen. Sweet-smelling shampoo and then a silky conditioner for his hair. He smelled and felt so girly, but he had to admit it all felt kind of nice. Though he tried mightily to think about other things, his thoughts kept returning to the big pink cushion and his “little squirtie.” He figured he was probably the only teenaged boy in the world who would call it that. “This is crazy,” he thought, and he felt ashamed. That weird dream had really gotten to him. Deep down, however, he was most concerned that part of him… had liked it.
He shook his head and rinsed out the conditioner. He grabbed another fluffy pink towel and dried off. Spying the body lotion, he read on the label that it was “silky and nourishing.” Sheesh. Not wanting to test his mother’s patience, he applied it all over. His skin really did feel silkier now, and it had the same light floral scent as the shampoo.
Meanwhile, in the next room, Gwendolyn lovingly laid out two dainty bra and panty sets on Josh’s bed. She would let him choose his undies for today, and then he could place the others in his dresser drawer. “Decisions, decisions,” she thought happily. In theory, this was all his choice, but she intended to box him in at every turn. She would coax, cajole, confuse and even manipulate her son, but she would not force him. Actually, she conceded, she would not force him unless there was no other option. She was determined. There would be no going back.
Gwendolyn had always been a very organized person, and she found purpose in her new project. Almost giddy, she continued her meticulous planning to extract and discard a few more traces of Josh’s boyishness. “Slow, steady and relentless,” she thought. That was the key. It was really for his own good, after all. Returning to her mantra, she thought “No half-measures.” Josh’s new arrangements were well in motion.
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I’m excited to take the this story forward with a slightly different direction. Thank you for the feedback.
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sissyboy1212, I'm starting to think that Josh is beginning to like some of his new bath regimen. His mom is enjoying the changes that are happening, too. Josh's dream was wild. Can't wait for the new direction you want to take this story in.
8)
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PART 22
When Josh emerged from the bathroom wrapped in his pink towel, he saw Kathy had joined his mother. On the bed he saw the bra and panty sets he was to choose from this morning. The first was mostly white and dotted with delicate little pink and green flowers. The panty set looked very silky with just a little white lace trimming. He sighed as he inspected the other set. This one was light purple and appeared to be made of cotton. Although it had no lace, the bra and panties were edged in darker purple. But the most obvious feature was the cartoony unicorn printed on the side of the panties. She was white with a flowing pink and purple mane. She had a bright yellow horn, long fluttery eyelashes and rosy red cheeks. Very sissyish.
Kathy looked on excitedly to see which one he would pick. “Josh these are so cute. I am so happy you are getting to enjoy pretty things now!” she exclaimed. Getting a whiff of the body lotion, she added, “and you smell so nice and sweet!”
“Once you choose your underthings, Kathy has been begging to pick out your outfit if that’s OK,” his mother said. “Now which bra and panties would you like to wear today? These are both true junior training bras unlike your bralette yesterday.”
Josh looked back and forth at both sets repeatedly. He didn’t want to put on either one of them. Finally, he settled on the one that looked a tiny bit less girlish. “I guess the white ones Mommy,” he said reluctantly.
“The white what, dear? Please be a little more specific,” Gwendolyn prodded.
“Here we go again,” Josh thought dejectedly to himself. Then he spoke meekly, “Mommy I would like to wear the white bra and panty set today please.”
Kathy squealed in delight. “Ooohh Josh can I please pick out the rest of your outfit? Mommy showed me some of the things she bought for you, and I know what would be perfect today!”
Almost grateful that he wouldn’t have to make another horrible choice, Josh quickly said “Sure Kathy, thank you.” She darted from the room, and Josh gingerly slipped on his new panties, shivering a bit as the lacy edges tickled his thighs. His mother helped him with his training bra, and he was surprised to see there were no straps over the shoulders like his bralette had. He remarked, “this one feels different Mommy.”
“Yes dear, I see you noticed,” she smiled. “This is a girls bandeau training bra. It doesn’t have straps. It just goes around your chest like a tube top,” she helpfully explained.
As the stretchy fabric hugged his narrow torso, the familiar sensation of being thoroughly wrapped in girlishness swept back over Josh. The feeling instantly returned his thoughts to the dream, and his little man started to poke in his panties. He blushed and tried to think of anything else.
“Do you like it, dear?” his mother asked smilingly.
With little hesitation this time he answered, “Yes Mommy I love my panties and bandeau bra. Thank you so much.” Then, almost surprising himself, he elaborated, “The little flowers are just darling.” After he said that, he was almost confused. “Why did I add all that?” he wondered to himself.
Gwendolyn was surprised as well at his additional flourish, but it pleased her immensely. “Oh that’s wonderful dear! Now put the other set away in your dresser, please. It’s best to keep everything neat and tidy,” Gwendolyn instructed. Her panty-clad son complied and took his unicorn bra and panty set to the dresser, knowing that soon he would be wearing that one too. “Now you’ll have something else to look forward to,” his mother beamed.
“What a treat,” the sissified boy thought. “Yes Mommy, I can hardly wait,” he said out loud.
As Josh turned from the dresser, Kathy returned merrily to the room. She was excitedly carrying her sissy brother’s outfit selection for the day. Josh had been holding onto a distant hope that it might be something like shorts, even though they would certainly be girls shorts. But as soon as he saw what she carried, those hopes were dashed. Standing in his bra and panties, he realized how silly that notion had been. Resigned once again to his girlish path, he did his best to smile and look appreciative as Kathy proudly presented him his next pretty dress. Less than 24 hours into this, and he now had two. He was awash in a sea of femininity, and he knew that it had barely begun.
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sissyboy1212, I swear, sissyboy1212, if you were a baseball player you would have hit anther one out of the park. 24 hours into his new feminine life and Josh has a new dress and underwear. I can't wait to see what happens in his girlhood saga. ;) ;) ;) ;) ;) ;) ;) ;) ;) ;) ;) ;) ;) ;) ;) ;) ;)
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Excellent story so far, sissyboy! Joshy can't escape and he's the "victim" of his own choices. Especially enjoy knowing Joshy's inner thoughts of humiliation, frustration and distress as he complies with his mummy's every request. Thank you for your writings.
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Thank you both Sissy Little Girl and babycakes for the nice comments. I appreciate your taking the time to read and react.
Hugs!
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sissyboy1212, No problem. You have provided a riveting story and you deserve all of the accolades that receive. Keep up the good work and get that next chapter out.
:P
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Very much enjoying this delightful tale. Thank you so much!
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PART 22
Seeing the dress, Josh knew at once he would be strapping on his polka dot sandals today. They were a perfect match for this girly-girl frock. He glumly examined it more closely. It was a delicate, baby pink sundress dotted all over with small black polka dots. Sleeveless with dainty spaghetti straps, it had generous off-the-shoulder ruffling across the top and around the hemline. The pink frock was made of a gauzy translucent material that looked incredibly feminine and wispy. An elasticized waist caused the skirt to flare out prominently. He detected multiple layers of the thin fabric rustling under the skirt which accentuated the flare even more.
“I just love this dress,” Kathy told her brother. “It’s made of chiffon. It’s a perfect summer dress. It’s just so light and breezy. It’s like something a fairy would wear. I can’t wait to get you in it, but there’s something else you need first!” Grinning, Kathy produced a thin plastic package and proceeded to open it up. “These white tights will be adorable with your dress, she added. Josh was horrified to see several rows of white ruffles on the seat of the opaque white tights as Kathy carefully removed them from the package.
Gwendolyn added helpfully, “Those are girls sandal toe tights, so there won’t be any unsightly seams on your toes. They are made to wear with sandals, and they’ll be lovely on you. Would you like to try on your tights now dear?”
Josh gulped softly and cleared his throat, “Ye.. Yes Mommy. Please let me put on my nice white tights now. The ruffles are sooo pretty.”
Kathy had him sit on the stool. She showed him how to gather his dainty tights at the toe and carefully slide them up his legs. Standing, he shivered involuntarily as he pulled them up over his panties and around his waist. His mother adjusted the frilly ruffles properly so they were nice and even on his bottom. Looking down, Josh saw the tights just made him look even more lithe and girlish. He felt new sensations of pressure and friction on his groin, and he was already having a physical reaction. He began to feel warm.
“Absolutely precious,” his mother said approvingly. “I was a little worried the Girls Size Large might be too small for a teenager, but they fit you perfectly.”
“Time for the dress!” Kathy announced. “Lift your arms, Joshy”
Josh smiled weakly and did as he was told, and Kathy slipped the gossamer-like dress over his head. It floated gracefully down into place and settled mid-thigh against his tights-encased legs. Kathy fastened a few buttons in back and then smoothed out her brother’s feathery skirt. She pulled the thin spaghetti straps into place and adjusted the ruffling off his shoulders just so. Stepping back to admire her handiwork, she was very pleased.
“Look in the mirror Joshy,” she said as she pointed him back toward the ornate full length mirror, “you’re adorable!” Josh saw his reflection and, just like yesterday, saw a waifish young girl staring back. This dress conspicuously highlighted his narrow, undeveloped shoulders unlike the boy clothes he normally picked to hide them. He looked and felt so… delicate in it. For the moment he was grateful, however, that at least it covered him up a bit down below. “And your other sandals will look fabulous with it too!” Kathy helpfully added, confirming his initial thoughts about the shoes.
“How does your dress feel, honey?” Gwendolyn asked pointedly.
“My dress feels nice and light, Mommy. The chiffon is so airy,” her son replied. The word “chiffon” just screamed sissy to him. He realized now that his bandeau bra paired wonderfully with this dress as well with no extra straps spoiling the look. He was chagrined at how slender and feminine he looked.
Kathy guided him back to the puffy stool and in no time at all had his matching polka dot sandals buckled snugly on his feet over the beautiful white tights. One, two, three, four, five, six tiny silver buckles in all.
“Those sandal toe tights really make all the difference. All nice and smooth with no sloppy seams,” Gwendolyn observed. “Don’t you love them Josh honey?” she prompted.
Josh studied his tighted feet strapped securely in his dainty pink polka dot sandals and wiggled his toes. It all looked so foreign to him. Then he answered his mother, “Oh mommy I love my tights. They feel so nice.” He felt a little shame as that second part was completely true. His little man could attest to that.
But his response was a tad too perfunctory for his mother. “Oh darling, you don’t really sound that excited. Use your words to express yourself, sweetie,” Gwendolyn continued. “I know you have an excellent vocabulary. Are they adorable? Or charming? Or perhaps delightful?”
Wrinkling his nose, Josh realized that his mother had upped the ante. What was good enough yesterday was obviously not enough today. He had to try harder. In a more bubbly tone, Josh exclaimed. “Oooh Mommy, you’re right! I do love my pretty ruffled tights with my chiffon dress. The whole outfit is simply… precious!” He tried to sell the enthusiasm, but he inwardly groaned as he heard the word “precious” escape his lips. Disturbingly, the whole exchange seemed to make his little man more active.
“Wonderful, darling! Much better!” his mother said approvingly as more boyishness was scraped away.
Kathy grabbed the hairbrush and said, “I have a different idea for your hair today.” She brushed his hair straight back and pulled out a pretty pink hairband. The U-shaped accessory was covered in soft pink fabric, and she pushed it onto her brother’s head so that it held his hair back.
Josh was mesmerized as he watched her work in the mirror. At one point, he was startled when he heard his mother’s voice, “Knees Joshy. Remember your posture.” Josh immediately straightened up on the stool into a much more girlish position. Gwendolyn was gratified to see him clap his knees tightly together and fold his hands carefully into his lap as he had been taught.
“Yes Mommy, I remember,” he answered. He really didn’t want to hold the makeup case again. Forcing his knees and legs together this way already increased the maddening tingling caused by the tights. He didn’t need any added pressure. Kathy continued to work on his hair. She tugged and combed a few strands of hair forward to give him wispy bangs and soften his look. She teased it some more and then spritzed hairspray to hold the bangs where she wanted them. Josh felt the pink headband clinging gently to his scalp, and he figured there must be little grippers or teeth keeping it in place. Gwendolyn couldn’t resist snapping a few photos of her children in this sweet moment—Josh sitting so prettily in his dress and tights while Kathy lovingly styled his hair.
“Stand up honey, and let’s have a look,” Gwendolyn insisted as Kathy finished.
Josh stood and was once again a vision of sissy glory. Kathy and his mother fawned over how pretty and girlish he looked. “Give us a curtsy, Joshy” Kathy encouraged him, “Pleeease!” Smiling weakly, Josh demurely bowed his head and dipped into a dainty curtsy. Clapping, Kathy said, “I think that was your best one yet!”
“Thank you Kathy,” Josh bashfully replied, not entirely sure how to receive this compliment. Gwendolyn insisted on a few more pictures of him on the plush sitting chair by the window. Josh dutifully gathered his skirt and sat down as carefully as he could. Gwendolyn noted appreciatively that he smoothed out his skirt without being prodded. He looked momentarily unsure about what to do with his hands, but then he sighed and folded them prettily on his lap.
“Don’t forget to smile, sweetheart,” his mother directed. Silently cringing, Josh smiled feebly and posed girlishly while his mother took several more photos.
Satisfied, Gwendolyn put down her phone and said, “Kathy you should also go put on something nice. I’ll freshen up too. I’ve made us Sunday brunch reservations for later this morning, and we’ll leave in a bit.” Kathy squealed with delight and headed to change. Josh paled at the thought of going out again in public so soon, once again dressed like the perfect little girl. “Josh you can make up your canopy bed and then wait in the sitting room while we get ready, OK honey?”
“Yes Mommy,” the sissyish boy replied. Subconsciously, he swished his fluttery skirt as he stood and felt it tickle his tights-covered legs. Then he stepped carefully to the bed to make it up. He was very aware of his bra as he reached for the fluffy pillows, and felt a little air on his backside as he bent over to straighten the sheets.
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sissyboy1212, Joshy is really getting the full girly treatment from Kathy and Gwendolyn. He is definitely having a hard (no pun intended) time with the tights. And now, he gets to go to a Sunday brunch. Sounds like fun!!!!
;)
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This is the inspiration for the lovely chiffon dress. Imagine it with smaller, black polka dots, a little more ruffling and several more layers under the skirt to make it very full.
And this is the inspiration for the polka dot sandals. I added the little silver buckles in my imagination.
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sissyboy1212, I love the images that you posted. Your making me jealous and I want that outfit. Keep going with this story and keep adding those visual post, too.
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I love the dress... it is totally dreamy. Girls are so lucky.
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Many thanks for the images sissyboy! They really add to the story. After all, a picture is worth a thousand words! :D
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I love the dress... it is totally dreamy. Girls are so lucky.
Yes, Sweet Baby Katie, we girls are lucky. We get to wear dreamy outfits that make feel like we are princess'. To take a phrase from the musical, "Bye, Bye, Birdie," I enjoy being a girl.
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PART 23
Josh made his bed like his mother wanted. (For the last 24 hours, he had been making his bed in more ways than one!) As he gazed around the girly room, it dawned on him that this was one of the few times he had been alone since this whole ordeal started aside from sleeping. He looked at the gauzy canopy bed and the little pink ribbons dancing down. Shifting his gaze to the dolls, he realized that’s almost what he felt like… a pretty and fragile doll. He examined the dolls more closely. There were three of them, and he saw small engraved nameplates on the bench. He hadn’t noticed those before. Their names were Penelope, Maddie, and Eliza. Penelope was wearing a pink gingham dress resembling the one he wore yesterday. She had blonde pigtails tied in pretty pink bows and wore pink patent Mary Jane shoes. His closet door was still ajar, and he saw his own gingham dress hanging there sweetly. Without really thinking, he picked up the doll and walked to the closet. Holding Penelope, he lightly brushed the lacy petticoat of his hanging dress and compared the dresses. Remembering he was supposed to go wait in the sitting room, he closed the closet door. Absentmindedly, he propped Penelope up on the bed instead of putting her back on her bench. He’d move her back later.
Sighing, he returned to the full-length mirror. The bashful little girl looking back was a picture of sugar and spice. Fifteen? He knew he looked ten or eleven at the very most. His thoughts drifted back to his dream. His little man perked up just remembering it. The way the tights felt constantly reminded him of being suc-ked down into the big pink cushion. His bedroom door was open, but he was all alone in the room. He took a deep breath and smelled his floral scent. Whatever this was, he knew down deep, was better than Sterncourt.
On a whim, he grabbed his skirt and playfully swished it around while he watched himself in the mirror. His breath got a little quicker. He started to feel the familiar taboo mixture of arousal and shame that had been teasing him throughout this entire process. He knew he should stop, but nonetheless he kept swishing his skirt back and forth. Swish, swish swish. It fascinated him to watch the chiffon dress dance and rustle over his tights. HIS chiffon dress and HIS ruffled tights. He paused for a moment as if in thought, and then he slowly lifted his skirt just enough in back to run his fingers across his ruffled bottom. It all felt strange and forbidden. Chiding himself silently, he pulled his hand back abruptly and let his skirt waft back down. His little man was fully awake now—but buried deep under his floral panties, ruffled tights and chiffon dress. Josh touched the front of his skirt to adjust himself through all the layers of girlishness, and it felt electric. He had to stop.
Yanking his hand back again, he shook his head sharply and stepped off the plush rug onto the hardwood. His polka dot sandals made a soft clacking noise on the polished wooden floor. Despite himself, he turned again to the mirror. The way Kathy had styled his hair with the pretty pink hairband really made him look younger. He touched the hairband and the fabric covering was surprisingly soft to the touch. He stopped to listen intently. He could hear the faint noises of his mother and Kathy getting ready elsewhere in the house, but they weren’t nearby. He wasn’t sure exactly why he did what he did next. Studying his reflection closely, he curtsied as gracefully as he could.
Spying the swivel stool, he listened carefully again. Still no one nearby. He pulled the stool out where he could see it in the mirror and then sat down. He tried to sit demurely and keep his legs together. “Knees, Joshua, Knees!” he reprimanded himself. He watched himself in the mirror as he folded his hands various ways. Sitting like this, his hands were folded on top of his chiffon skirt right above his little man. He squeezed his legs together tighter and shuddered slightly. It felt very nice, but he was wary of making another “little squirtie” right now. He was playing with fire.
He pushed off with his feet to spin around on the stool and straightened out his legs as he twirled. The white tights were such a contrast with his colorful skirt and shoes. He stopped spinning and breathed deeply. Surrendering hesitantly to temptation, he pulled his skirt up again with one hand. With the other, he tickled the front of his tights and closed his eyes. His pulse accelerated. In his mind’s eye, he was tumbling through the air again high above the satiny pink cushion. He hooked his thumb in the top of his tights and slowly began to pull them dow—
“Josh! where are you, honey? We’re ready to go!” he heard his mother call abruptly. Snapped rudely from his trance, his face grew hot. He heard her footsteps in the hallway now. “Josh, I don’t want to be late!” she called again.
Josh smoothed his skirt frantically. His frustrated little man was practically screaming at him. “I’m coming Mommy, I’m coming!” he squeaked nervously. He could tell she was near the open door.
A second later, Gwendolyn appeared in the doorway. She saw that the canopy bed had been neatly made as she asked… but why was there a doll on the bed? Josh was blushing furiously. And why was the vanity stool in the middle of the room?
Gwendolyn turned a probing gaze on her son. Josh was crimson. She didn’t know precisely what was going on here, but her intuition was whispering to her, and she had suspicions. Whatever Josh had been up to, however, she sensed that it was not necessarily disrupting her plans right now. She felt sure she would ferret it out in time.
Her gaze lingered a bit longer on her fidgeting sissified son. Then, with a sly grin, she delivered another little nudge. “Oh I see you’ve been playing with the pretty dolls. How sweet! But, come along, honey. It’s time for brunch! You can have more time with your dollies later.”
Humiliated even more, Josh silently chastised himself for leaving the doll on the bed. Still, he was eager to escape this moment and quickly blurted out using his best sing-song voice, “Yes Mommy of course! I can’t wait for our lovely brunch!” His little man was still angry, but it was starting to calm down. Now his mother thought he was playing with dolls—which was basically true—but at least she didn’t know the rest.
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sissyboy1212, Josh is getting deeper into his girlish way of life. Unfortunately, he can't catch a break and his mommy or Kathy always see to show up at the wrong time. He even made a mistake of leaving Penelope on his bed and had his mom see it there. Now, she thinks he likes to play with dolls. Better buck up, Joshy because you are in this for the long haul.
:P
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Please continue the story. Excellent story line so far. Like Josh I would not have chosen military school and the excessive discipline. After all this girl thing is for only a few weeks while we are on vacation right? Sure it is Josh. Keep thinking that.
Again please continue.
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PART 24
Josh saw Kathy had changed into a sleeveless navy dress. She looked every bit a maturing teenage girl. Tastefully dressed but still casual. In her modest heels, she practically towered over him now. Anyone would think he was her little sister.
They all piled into the car. Normally, Josh would have barged his way into the front seat, but he was moving more carefully now and was relegated to the back. He had a bit of trouble gathering all his dress as he got in the back seat, and Kathy had to buckle his seat belt when he couldn’t find the connector under his frothy skirt. Even in the car, his mother had him keep his knees together. “Practice makes perfect, honey” she admonished.
Arriving at the cute little restaurant by the water, they were seated at a lovely little table by the window. It seemed to have a bit of an old English theme. The restaurant was busy with the brunch crowd, and Josh was keenly aware of people looking at him. Other boys and girls with their families seemed to be wearing mostly shorts. He didn’t see many skirts or dresses, so he stood out somewhat. He felt sure they all thought he was just a pretty little girl, and he tried very hard to look the part. He just concentrated on maintaining his posture and keeping his skirt under control. He especially focused on keeping his legs clamped together, wary of his mother’s cosmetics case. Sitting in this crowded restaurant on his chiffon skirt in his panties and tights made him feel constantly uneasy.
They enjoyed a nice meal, though, and Gwendolyn again noticed how Josh ate more delicately. He was definitely preoccupied with the way he was dressed. As they finished, Josh was chagrined to see a familiar face approach their table. It was Mrs. Smyth from the dress shop!
“Well hello, Gwendolyn, how lovely to see you all again today,” Mrs. Smyth greeted them. Josh was nervous. She knew his secret.
“Thank you,” Gwendolyn replied, “we look forward to visiting the shop.”
“As do I,” she smiled. There was another nicely dressed lady with her. “This is my good friend Andrea. She runs the salon across the street from my shop, and we’ve been friends for years.” Turning to Andrea, she added, “these are the Hartleys. They are visiting and staying at the Meriweather place.”
“I’m Andrea Lewis. It’s a pleasure to meet you. Don’t you all look lovely!”
Gwendolyn thanked her and Kathy introduced herself. To Josh’s horror, Mrs. Smyth gestured to him next and spoke softly, “Andrea, this is the one I told you about.” And then she whispered loudly, “Can you believe he’s actually fifteen?”
Mrs. Smyth spoke to Josh with a knowing smile, “that is an adorable dress, dear, and I know my frocks! I love the spaghetti straps. They accentuate your petite shoulders so nicely. You’re lucky to have a marvelously narrow frame. Those sandal toe tights emphasize your slender legs and contrast well with that skirt color. Would you indulge me and stand up so I could appreciate it all better?”
Josh was blushing furiously and seemed unable to speak. With her years of experience in fashion, Mrs. Smyth easily recognized and noted every girlish detail of his appearance. Already sensitive about his slight build, Josh winced as she immediately made it the focus of her trained eye. Gwendolyn prodded him, ”well what do you say, honey?”
“Thank you for saying all those sweet things, Mrs. Smyth,” the embarrassed boy finally replied, “Of course I’d be thrilled to show you my dress.” Josh got up carefully and stood awkwardly by the table. Other diners were starting to notice this exchange. In such a small town, it was obvious that most of them knew each other anyway. His mother had him turn around so the ladies could see the back, and he unconsciously twirled his skirt as he did so.
A small girl with her family two tables over called out, “Oooh so pretty! Mrs. Smyth did that dress come from your shop?” She stood up to get a better look. An adolescent boy sitting next to Samantha, obviously her brother, rolled his eyes and turned back to his plate. Now more people were watching.
“No Samantha,” Mrs. Smyth called back, “but I have some lovely ones that are very similar.”
Then she whispered to Gwendolyn, “she is a lovely child, but her brother Justin is a terror—nothing at all like your sweet Josh here. They practically let him run wild!”
Gwendolyn watched all this play out with amazement and delight. How had she been so fortunate to literally stumble upon such a wonderful ally? She’d really had no more elaborate plans for the morning than just getting Josh out in public in another pretty outfit. Dolores Smyth, however, was reinforcing everything that she was trying to do with her wayward son. This was an unexpected godsend. “If she only knew…,” Gwendolyn mused to herself, thinking of how different the reaction might have been to the naughty Josh of last week. Elated, she exchanged a knowing look with Kathy and squeezed her daughter’s hand.
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sissyboy1212, this story gets better with each chapter. I can't wait for the next chapter.
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Discovered a fault in the Chapter numbering
There are -2- Chapter (Part) 22
Re: New Arrangements for Josh
« Reply #76 on: August 22, 2020, 12:29:50 PM »
PART 22
Re: New Arrangements for Josh
« Reply #82 on: August 24, 2020, 04:37:49 PM »
PART 22
Need to increase the 2nd Part 22 to 23 - 23 to 24 - 24 to 25
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What could be better than to be out in a pretty chiffon dress and sweet panties?
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Thanks for pointing out the mis-numbering. Doesn't look like I can go modify the older posts. I guess maybe they "lock" after a period of time. Perhaps a moderator can make the edits? Thanks!
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PART 26 (no you didn't miss PART 25. Just getting the numbering right from here forward after it was kindly pointed out :) Perhaps at some point a mod can correct my mis-numbering from the earlier parts.)
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Mrs. Smyth returned her full attention to Josh, and she gained momentum as she continued to inspect his ensemble. “The whole look is precious. The polka dots are very on trend for young girls. Nice, even proportions. The skirt is short enough to be sassy without being inappropriate. A little bouncy perhaps, but pretty nonetheless. I like the ruffling detail too… very playful but not overdone. The matching sandals and lovely hairband pull it all together sweetly,” Mrs. Smyth complimented him.
Kathy blurted out, “You should see his curtsy!” Josh was certain he saw that boy, Justin, jerk his head around when he heard Kathy say “HIS curtsy.” Glancing over, Josh saw Justin perusing him with renewed interest. “Go ahead!” Kathy whispered.
Seeing no other option, Josh dipped down into a quick curtsy for Mrs. Smyth who was both surprised and flattered by the girlish show of respect. Gwendolyn involuntarily gasped. This was all so surreal and wonderful. A younger couple in their twenties sitting in the corner watched the spectacle attentively. A teenage girl at a different table leaned over to her mother to whisper something.
Grimacing, Josh daintily sat back down. He was weak-kneed and needed to sit. Could this get any worse? He couldn’t believe there was this much to say about his outfit. He caught a glimpse of Justin, and the boy’s eyes were positively bulging. Josh quickly looked away.
“Bravo dear! Very sweet! That was lovely… just lovely!” Mrs. Smyth exclaimed. Then she continued, “your sundress is so light and breezy with that charming flare silhouette. Those extra layers under the skirt really do make all the difference in the fullness of your skirt. It’s chiffon, isn’t it dear? And did I detect the briefest hint of some pretty ruffles on your lovely tights when you twirled around?”
Now beet-red, Josh stammered, “Yes ma’am, you are right. My dress is made of pink chiffon, and I’m wearing some nice ruffled tights underneath.” It was excruciating to have every girly detail of his outfit described in this public setting, and it was another blow to realize he had unwittingly exposed his frilly bottom. Desperately trying to shift attention elsewhere, he said, “Kathy picked it out for me.”
Smiling, Mrs. Smyth said to Kathy, “well you certainly have a nice eye for fashion dear. Very feminine and summery.” Mrs. Smyth further commented, “your navy dress is chic as well. Simple but elegant. Very in style.”
Kathy smiled modestly at the compliment, “Thank you very much. I was just happy to help out when Josh decided he wanted to start trying girly things.”
“She did his hair too,” Gwendolyn explained to Josh’s discomfort as she directed the conversation right back to him. She had relished the last few minutes, and she wanted the focus to remain on her son. “It’s amazing what she’s done with it since he hasn’t had a proper haircut in months!”
“Well you’ve done a wonderful job, Kathy,” Andrea concurred. Reaching out to lightly brush Josh’s hair with her fingers, Andrea said, “but if you want to get that proper haircut this week, I’d be happy to put him in my chair.” Speaking to the blushing boy, Andrea said, “fortunately it’s long enough that you’ll have several nice styles to choose from.”
Catching his mother’s eye, Josh knew he should say something. “Thank you Miss Andrea. That would be so wonderful… if it’s OK with Mommy I mean,” he said softly. He knew it was a long shot, but maybe his mother wouldn’t want to go to all that trouble. He squirmed in his chair causing his chiffon dress to rustle and swish. Reflexively, he pulled his knees together a bit tighter and felt the tingling friction of his ruffled tights rubbing against his thighs.
The childish way Josh addressed his mother did not go unnoticed by Andrea, but she didn’t comment. Speaking again to Gwendolyn, she explained, “truthfully my schedule is rather light this week, so I can easily work him in. In fact, we have enough stylists to take you all for an appointment if you like and get a family discount.”
Grateful for Andrea’s generosity and pleased to have steered the conversation back the right way, Gwendolyn immediately replied, “that would be wonderful, Andrea. You are too kind. Of course we will. Thank you so much!” She was thrilled at this additional opportunity.
“Here’s my business card, just call tomorrow morning and we’ll get you all booked this week. It won’t be a problem,” Andrea replied.
“Joshy you should bring all your hairbows and barrettes so Miss Andrea can see them,” Kathy chimed in. “He’s got a whole box of cute accessories!” she added enthusiastically.
“Bring whatever you like dear,” Andrea smiled, “We should certainly help you make the most of all your pretty things.”
Josh’s skin was crawling now. So much for that long shot. The week ahead was rapidly filling up with all sorts of sissy horrors. A looming visit to the dress shop. A hair appointment. No doubt more girlish outfits. The unicorn bra and panty set in his dresser. The box of hairbows and barrettes on his vanity table.
“See you very soon, Josh!” Andrea told him eagerly as they said their goodbyes. Departing, she added, “that floral scent is lovely by the way.”
She said his name a little too loudly, and the busboy clearing the next table obviously heard it. The lanky teenager didn’t say anything, but he stared intently at Josh for a few agonizing moments. He looked to be fifteen or sixteen. Although he was roughly Josh’s age, he looked much more like a typical teenaged boy who probably played several sports. Chuckling quietly, the boy finished clearing the table and headed to the kitchen.
As his mother paid their check, Josh saw him whispering to another busboy and discreetly pointing in his direction. The second boy’s eyes widened, and they both began to giggle before the manager told them to get back to work.
Josh was beside himself. Everybody in this town was going to know he was a sissy. And he had actually chosen to do this. He stepped daintily behind his mother and sister as they headed for the door, his chiffon dress rustling every step of the way. He absentmindedly reached up and touched his lovely pink hairband. He had to walk right by Samantha and Justin who were still ogling him. He tried to avoid eye contact.
Gwendolyn, however, paused when she saw the face of Justin’s mother. As that boy was silently mouthing something vulgar at Josh, she thought she recognized a kindred spirit. While the ill-mannered Justin continued to make fun of Josh with an exaggerated limp wrist gesture, Gwendolyn spontaneously decided to share a little more with this stranger. Smiling kindly, she bent over and whispered briefly to Justin's mother. As Gwendolyn stood back up, Josh detected a curious look on the other lady's face. Justin's mother was staring intently at Josh now as if seeing him for the first time. Gwendolyn felt rejuvenated, and she continued to the door.
As they exited, Gwendolyn paused to pick up one of those little flyers that advertise local events which were stacked on a table by the door. Reading it, she remarked, “well that looks interesting.” Josh saw her tuck the flyer in her purse.
As they got back in the car, Josh saw the same lanky busboy through the window talking to their waitress. She smiled and waved as they pulled out of the parking lot. Josh sighed and looked down at his chiffon skirt as it poofed up prominently below his seatbelt. He folded his hands on his lap and held it down as best as he could.
From the front seat, he heard a familiar refrain. “Knees, Joshua.” His knees instantly flew back together.
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The busboy is a tantalizing hint of things to come, I'm sure, but I'm especially excited by the impending hair appointment. Sure, hair can be fixed easily, especially when it's a boy going from a girly hairstyle, but it still has a sense of longevity and near-permanence all the same.
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sissyboy1212, Great chapter.
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PART 27
Instead of returning directly home, Gwendolyn drove them to the little boardwalk to see the water which was just off the main street. “We’ve been here over a day and haven’t seen the ocean yet. That just won’t do!” she announced.
Still dressed in their nice brunch clothes, they got out of the car and walked on the boardwalk to admire the scenic water. Lots of people were on the beach, and they paused often to look at everyone having fun. Josh soon realized that the sea breezes here by the water constantly blew his light and airy skirt up. Despite mighty struggles, his pretty ruffled tights were repeatedly exposed every time the wind outwitted him to lift his skirt again.
Kathy chuckled, “Josh you’re going to have to work on that. It looks like you’re already attracting some new admirers!” She pointed to a couple of older teenage boys with deep beach tans watching them. They had obviously been in the water, and they were relaxing on the side of the boardwalk soaking in some sun.
Beet-red, Josh made eye contact with them, and one of the boys smiled weirdly back at him. It was obvious he thought Josh was just a pretty little girl. Deeply embarrassed, he had to look away quickly. The wind continued to blow his delicate skirt around, and he felt his little man growing again in his tights. Josh felt so weak and effeminate compared to these masculine and athletic boys lounging in their board shorts. The sissified boy was acutely aware of this contrast as he minced along the boardwalk desperately trying to control his skirt.
On top of everything else, Josh had an increasingly urgent need to pee. He hadn’t gone in the restaurant… it was too unnerving to use the ladies bathroom, and he hadn’t dared go inside the men’s room dressed as he was. Plus, he had been so eager to get out of that place, he hadn’t really considered asking to go there. So he had just held it. As a result, the pressure had been building for a while. Seeing the ocean with all the water and the waves crashing just made it worse.
Finally, Josh had to speak up. “Mommy,” he began nervously, “I need to pee.” Hearing this, Gwendolyn asked, “Why didn’t you go in the restaurant sweetheart?”
Not wanting to explain all that to his mother, he replied in a small voice, “Uhh I didn’t need to go then.”
“Well you will have to hold it for a few minutes until we find a ladies room, honey. And for goodness’ sake please use language that’s more appropriate. You should say ‘tinkle’ if you have to do number one. Why don’t you try again more nicely while we find one?” she prodded.
Grimacing, Josh tried again, a little more urgently as he felt the pressure mounting. “Mommy, please I need… to tinkle. I really need to go!”
Gwendolyn was satisfied and spotted a facility on the boardwalk that they could use. As they walked that direction, Kathy chuckled and whispered helpfully, “if you ever to have to do a number two, you could always say you need to ‘make a poopsie’. That’s what I said when I was little.”
“Oh yes Kathy you’re right that will be perfect thank you!” Gwendolyn nodded approvingly. “So Joshy, it will be ‘tinkle’ for your number ones and ‘poopsie’ for your number twos, OK?”
“Yes Mommy,” the embarrassed and feminized boy replied. As they approached the bathroom, his mother asked him to repeat his instructions so he wouldn’t forget. Josh complied readily to avoid any further delays, so he repeated several times “Tinkle is for number one and poopsie is for number two. Tinkle is for number one and poopsie is for number two.”
When they finally got to the little shack, the ladies room was occupied, so they stood outside waiting. The pressure was getting worse now and Josh crossed his tights-encased legs causing him more uncomfortable friction. Finally the door opened and a lady came out. Eager to be out of his misery, Josh started to dart into the ladies room, but Gwendolyn was quicker and surprised him by grabbing his hand. “I’d better take you in sweetheart. With your pretty dress, that full skirt, and your tights you may need some help until you’re more used to them. I’ll take you in to tinkle.”
Mortified but having no other options, Josh meekly allowed his mother to lead him into the ladies room. There was one stall with no door. Josh realized that it was going to be a process getting free of all his girly garments to relieve himself, and he was running out of time. He entered the stall while his mother coached him through everything. First he carefully slid his ruffled white tights and then his panties down around his ankles. Next, he had to gather his frothy pink skirt and sit down making sure that everything was clear. But he had another problem now. Freed from all its feminine trappings, his little man was sticking straight up. He finally got it pointed down the right way by leaning very far forward and pushing down a bit. As his flow finally started, his mother called out to him from the other side of the partition “Is everything OK honey?”
His concentration interrupted, Josh replied nervously, “Yes mommy everything is fine!” After a minute, Josh was finally able to relieve himself in fits and starts and wiped himself with a tissue when he was done. He realized that he had inadvertently dribbled a bit on his tights and the floor. Standing up, he pulled his panties and tights back up and walked out. Gwendolyn patiently helped him get his chiffon dress adjusted back correctly. Then she made a slight frown as she saw the damp spots spoiling the look of his pretty white tights.
Next, his mother looked in the stall and saw more untidiness. With all the pressure and complications, Josh’s aim had been somewhat less than perfect leaving drops on the seat and a few on the floor as well. “Josh sweetie,” his mother gently reproached him, “young ladies always clean up after themselves as a courtesy to the person following them.” Josh blushed even brighter and then used some tissue to wipe things up while his mother supervised.
“Hmmm,” she thought out loud, “we may have to look at some other options for you until you get more accustomed to your new outfits. This is twice today you’ve had a little accident” she added, reminding him of his mess that morning. Josh could do nothing but continue blushing silently. “Make sure you wash your hands very well, dear” she finished.
“Yes Mommy,” the sissified teenager complied meekly as he worried what her last comment might foreshadow.
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sissyboy1212, Another great chapter. Josh is really getting lots of training in his girlhood and his mommy loves humiliating him.
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PART 28
After the ordeal in the ladies room, the sky was getting overcast and it looked like it might rain. They all headed back to the car passing the same two teenage boys. Once again, Josh felt incredibly small and sissyish by comparison. He was keenly aware in that moment of the way his thin spaghetti straps drew attention to his waifish shoulders. The flouncy off-the-shoulder ruffling just screamed “sissy.” In contrast, those boys’ shoulders looked so much broader than his. He was probably the same age as them, but his old boyish life already felt as distant as another planet. Without even thinking, he lightly brushed his pink satiny hairband. Then, the emasculated teen shivered slightly as another sea breeze exposed his ruffled tights yet again. As he grappled with his chiffon skirt, he minced as quickly as he could in his polka dot sandals toward the car. He felt he was being swept away uncontrollably on a wave of femininity. Back at the car, Kathy again buckled him into the back seat and he didn’t even think to protest. His voluminous chiffon skirt swished all around him as if determined to wash away any last shreds of maleness as they made their way back to the house.
Thankfully, the rest of the day was mostly uneventful. He kept his polka dot sundress on, but they all stayed inside the house as the storm rolled in. Gwendolyn noticed with appreciation over the course of the afternoon that he seemed to be getting much more in the habit of gathering his skirt when he sat. He appeared to be getting more comfortable in his dress. To pass the time, Josh and Kathy worked on a jigsaw puzzle together. For a while, Josh forgot the way he was dressed and just enjoyed the time with Kathy.
Later in the afternoon, Gwendolyn did a video call with his Aunt Karen. Before they finished their conversation, Gwendolyn called Josh over to say hello. He had always been somewhat intimidated by her domineering demeanor, and he cringed silently when his mother prodded him to show off his pretty dress and twirl around for his aunt to see. He knew that he was going to have to show her eventually, but he just had hoped it wouldn’t be quite so soon. Each little step like this made his situation seem more… permanent.
“Your mother says you can do a lovely curtsey Joshua. Please show me.” It was phrased as a request, but Aunt Karen’s tone of voice made it come across more as an order. She was used to having her way. Of course, Josh performed a curtsey over the video for his aunt. Then he had to thank her for his pajamas. Before the call was over, Gwendolyn had him bring out his pink gingham dress from yesterday so Aunt Karen could see that one too. As his aunt seemed very interested, Josh found himself forced to describe the details of his first dress in very girlish ways. “It’s such pretty pink gingham. It has a nice back bow and the cutest short puffy sleeves…”
“Those are called bubble sleeves, right dear?” Aunt Karen prodded. She was enjoying this immensely although she already knew what both dresses looked like… she had helped pick them out!
“Yes, Aunt Karen, uhh, bubble sleeves and a darling little butterfly applique on the skirt.” Josh was becoming well versed in all the exquisitely feminine details of his girlish outfits. It was like all these girlish little facts and particulars were just lodging themselves in his brain. His mother had him bring out his box of hair accessories as well. It was like a horrible game of “Show and Tell” where he had to recount to his strict aunt all the ways he was turning into a sissy. Finally, after showing her his pink polka dot sandals with the dainty silver buckles and describing the bra and panty set he was wearing, he managed to get off the call.
As she told him goodbye, Aunt Karen said, “I must say this is a welcome change Josh. Good for you sweetie! I’m so pleased to see how hard you are trying. Remember, as your mother and I have discussed, you can only truly change your ways if you make the honest effort.”
“And promise me, honey, that you’ll send a picture of your pajamas tonight so I can see how they look on you!” she continued. “Once I saw all that delicate tulle with those precious hearts, I knew they’d look adorable on you.”
“Yes Aunt Karen,” Josh sighed in surrender, “I promise.”
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sissyboy1212, Josh is slipping farther and farther into Sissie hood. He sure caught the attention of those 2 boys that were watching as his chiffon skirt blew up and gave them a look at his ruffled tights. Great chapter and I can't wait for more.
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PART 29
Later that night, Josh returned to his bedroom to prepare for bed. He paused in front of the full length mirror again. Without really thinking, he swished his chiffon skirt for the umpteenth time today, mesmerized by the way all its layers floated breezily around his waist. Studying his reflection, all he could see was a sissy. He gathered his ever-rustling skirt and sat down on the puffy pink stool. Leaning over, he unbuckled his strappy sandals and took them off. He wiggled his toes as he studied his petite feet clad in his white tights. Turning to his vanity mirror, he carefully (almost reluctantly?) took off his hairband and returned it to the storage box. Unconsciously, he lightly brushed his bangs out of his eyes. About the time he realized that he would need help unbuttoning the back of his dress, his mother knocked softly at the open door. She had obviously been standing there for a few moments. She didn’t speak but smiled sweetly at him. Reflexively, he pulled his knees together and folded his hands as he had been taught.
Gwendolyn’s heart was full as she admired her son perched so daintily on the stool. His white stockinged feet contrasted sweetly with the plush pink rug. She had simply adored watching the way he gently removed his pink hairband. She was thrilled to see her efforts coming to fruition. His rough boyish edges were being continually smoothed away. With his chiffon dress billowing around him, he seemed cocooned in its layers of pink femininity. Neither of them spoke. She stepped behind him and unbuttoned him while he sat demurely and watched her in the mirror. Once she was done, he stood and stepped out of his sundress. Now wearing only his ruffled tights and training bra, he hung it in the closet next to his gingham dress under his mother’s watchful eye.
Gwendolyn relished the exquisite tenderness of this moment as she nurtured her wayward son’s budding femininity. As Josh stood shyly, his mother had one more little surprise for him. He hadn’t noticed when she first entered, but she had brought yet another pair of panties and a small pink box. The panties were a silky lavender material with a fringe of scalloped white lace around the waist and leg holes.
Finally, Gwendolyn broke the silence and spoke, “Aren’t these cute, sweetheart?”
After a moment, Josh replied softly, “Yes Mommy they are very pretty.” Honestly they were pretty, and in any event he was resigned to the fact that he would certainly be wearing them soon. She handed them to him, and he held them gingerly while his mother took another item from the pink cardboard box. He grimaced as he saw the box’s label, and then he remembered his mother’s earlier remark about “other options.”
“Josh, these may help with your… accidents. These are panty liners, and they will just give you a little extra protection.” Somewhat flustered now, Josh gawked as she held up a small pink hourglass-shaped pad. “Girls around your age begin using them when they start getting their periods, and they will help you stay tidy too,” his mother explained. As the reality sunk in that he was going to wear this supremely intimate and feminine item, he felt another meager remnant of his masculinity dissolve. His mother showed him how to use the adhesive strip to secure his panty liner in his panties. As she supervised, Josh positioned the panty liner—HIS panty liner—into place on his lavender panties. Josh felt as though he was a spectator watching this all happen to someone else. He cringed even thinking the words “panty liner.”
Satisfied, Gwendolyn continued, “Now please go brush your teeth and change into these for the night. If you have another ‘little squirtie,’ your panty liner should at least keep us from having to do more laundry.” Handing him the box, she added, “and you can take the rest of your panty liners and put them with your other toiletries.” In a near daze, Josh went into the bathroom. He quickly put his pink box on the vanity and then brushed his teeth. Feeling defeated, he took off his tights, panties and training bra. Then, he slowly put on the fresh lavender panties with his panty liner. The lacy fringe tickled his thighs as he slid them on and aroused him again. He immediately noticed the feel of the liner’s extra bulk, and he also saw that it smoothed out the front of his panties so that he looked even more girlish. Even in its current state, his “little man” was more or less hidden underneath the feminine trappings. A few days ago, he was a normal teenage boy. Now, he was a sissy using his first panty liner. He belatedly realized that he had left his PJs outside on the bed.
He reluctantly emerged from the bathroom in just his lavender panties. While Gwendolyn watched happily, he picked up the freshly laundered pajamas and pulled on his delicate white leggings. Then he slipped on his crop top with the cute little cap sleeves fringed in tulle. It seemed they had shrunk slightly in the wash, so now his leggings were tighter and the top was more clingy. As he looked down at his slender legs, the pink hearts on his leggings seemed to taunt him merrily.
“Doesn’t that feel nice honey, knowing that your panty liner better protects you from little accidents now?” she asked. She had noted his initial reaction when she said “panty liner” so she was repeating the words intentionally now.
“Yes Mommy,” he replied almost automatically. Realizing that she expected a fuller response, he said, “Thank you for my… panty liners.” The words seemed to linger on his tongue as a reminder of how sissified he had become. Once he was dressed in his jammies, Gwendolyn took several photos of him in his PJs for Aunt Karen as he smiled timidly. No matter how hard he tried, his thoughts were consumed by what he was wearing underneath.
“Did you remember to tinkle, honey?” she asked him, reminding him of the earlier episode.
“Yes Mommy I tinkled earlier,” Josh answered, the childish words just adding to his discomfort.
Smiling, his mother said, “Josh I’m proud of the progress you are making. I’m so glad you chose this route. I just feel that it was meant to be, and I’m amazed at how girlish you are already becoming. I promised I would help you, and I’m going to keep my promise!” Of course Gwendolyn had no intention of letting him “choose” any other path, but she felt it was important that he come to accept these decisions as his own. No half-measures!
Josh winced at the “compliments.” Again reminded that all this had been his decision, Josh could only reply, “thank you for helping me Mommy.” Despite his feelings of embarrassment and confusion, however, he also felt his mother’s true affection. No matter what else was going on, he could feel that she genuinely loved him. Maybe it was just her unconventional way of showing it.
She insisted on tucking him in and kissing him goodnight the way she did when he was a child. “Good night Josh. Sweet dreams!” she said as she turned off the light and shut the door.
Lying in the frilly bed, Josh’s mind raced as he tried to imagine how and when he might reclaim his old life. Disturbingly, he found it increasingly hard to see a path leading back to the life of a teenage boy. At the core of it all was a nagging question: Did he actually WANT to be a sissy? He felt like Hansel and Gretel when they realized there were no bread crumbs to lead them out of the forest.
He had made a choice and a commitment. In the span of a couple of days, he now had a new girly wardrobe with more additions surely on the way. His old clothes were completely gone, replaced by dresses hanging in his closet and panties in the drawer. He was awash in a sea of ruffles and tulle. And ribbons and lace. Sandals with flowers and a gingham dress with a Peter Pan collar. He had his own pair of ruffled sandal toe tights. What normal teenage boy even knew there was such a thing as sandal toe tights? What kind of teenage boy wore anything made of chiffon, much less a dress? He wore girls’ pajamas, panties and now a panty liner. How far gone might he be after a week? Or a month? Or months? Could this go on for a year? Or more? All these “firsts” were leaving indelible marks in his brain. His first dress. His first hairbow. His first panties. His first bra.
He was not returning to his old school until at least after the summer. Instead of playing video games he was learning how to curtsey. Could he change his mind at this point and go to Sterncourt after all? He shuddered at the thought. “Definitely not,” he concluded. He knew deep down he wouldn’t choose that even if he could.
This whole town seemed destined to know him as nothing but a sissy boy. Aunt Karen knew about his choice and was thoroughly in on it by all appearances. It seemed inevitable that everyone he knew would eventually come to know him as a sissy. Trips to the hair salon and dress shop loomed. He felt more butterflies in his stomach, and he spied Penelope the doll, illuminated by a night light, sitting prettily on her bench. Mentally exhausted, Josh drifted to sleep.
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Much like “Slow Burn” I love the fact that they hate themselves when they see there becoming sissies. It really adds to the realism
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Thank you! Although I personally wouldn't say Josh hates himself. I think he is extremely embarrassed by what is happening to him, but what really scares him is that deep down he is afraid there is a part of him that likes it. I haven't finished writing the story yet though, so I truly don't know exactly where he is going to wind up. :)
I love dealing with flawed characters. Gwendolyn is certainly one. I think Josh may be one too...
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Personally, I think that Josh's internal struggle is what's keeping me so entertained by this story and excited to see where it goes since I don't think he'll be getting out of it any time soon.
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Let's not forget this is actually Josh's choice. He could have gone to Sterncourt but he chose sissyhood instead. He must have understood, at some level since Gwendolyn laid out the clothes for both choices on his bed, the ramifications of his choice. His mommy is just helping Josh follow through with his decision. The only confusing part of this story is highlighted in Part 29 when the author tells us, "Of course Gwendolyn had no intention of letting him “choose” any other path, but she felt it was important that he come to accept these decisions as his own. No half-measures!" What if Josh had actually chosen Sterncourt and followed through on his decision? Wonder what Gwendolyn's backup plan was or maybe still is if he chooses to opt out of this softer path and try Sterncourt. And what happens when vacation is over and he has to go back to his school? Can't wait to see the story further unfold.
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Thank you for the nice comments. Babycakes, I think that if Josh had chosen Sterncourt initially, then he would have gone to Sterncourt. That might be worth a different story sometime.
But once he made that initial choice, I think it was over. When Gwendolyn saw him in that first dress, his fate was sealed. She was positively giddy seeing him dressed as a girl, and she is emotionally invested in his sissification now. I think for her it has been a process too. At least right now she has no intention of letting him change course. So I think she will go to great lengths to create circ-umstances to support that.
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PART 30
Sunlight filtered into the elaborately feminine bedroom, and Josh woke up. Warm and snug in the pink bedding, he gazed up at the gauzy pink canopy and all the tiny pink ribbons and bows. He could not imagine a more sissyish place for a teenage boy to sleep. He realized that he was extremely aroused, and as he felt down he remembered now what he was wearing. With a sudden flash of panic, he reached down to see if he had had another accident, but thankfully his panties and his new panty liner were dry.
As he shook off his covers, he felt so girlish to see his heart covered leggings clinging to his slender legs. He noticed the door to the bedroom was open, so he realized his mother must have already checked on him. Sighing, he decided to go ahead and shower. He headed to the bathroom and stripped off his lavender panties. Looking at his panty liner, he realized that he didn’t know exactly what to do, but he saw a tiny wet spot on it and decided it was best just to throw it away.
When he was done showering, he heard his mother call to him from the bedroom. “Good morning, honey I hope you slept OK?”
Slipping immediately back into his juvenile role, he answered “Yes Mommy.”
“Did you stay dry last night?” she continued.
Feeling very childish, he stammered quickly, “Yes Mommy. No accidents!”
“Wonderful dear!” she called back. Since they are still clean, you can keep wearing the lavender panties or you can get your unicorn set from the dresser, whichever you’d like. It’s your choice! Just be sure to change your panty liner, sweetheart!” she instructed. “I’ve gotten you something a little more casual to wear today on the bed. I hope you will like it.”
“Great,” Josh muttered. After thinking about it, he decided to stick with the lavender panties. At least they were a little less childish. The sissified boy gingerly put a fresh panty liner in his panties, still unsettled about the whole emasculating process. Finished, he slipped them on, feeling the familiar tickle of the lace. Extremely self-conscious, he exited the bathroom and saw his mother was still there holding another lavender garment. Suddenly self-conscious, he tried to cover his panties with his hands.
“Those panties are actually part of a set, honey. Would you like some help with your bra or would you like to try putting it on yourself?” she smiled pleasantly ignoring his shyness. “You need to get used to putting on your training bra even if you’re not as… developed yet.”
Sighing again, Josh said “I’ll try doing it Mommy.” He glumly reached for the matching lavender training bra, noting the same fringe of white lace as his panties. His mother showed him how to first put his arms through the straps and the fasten it a little sideways on his chest. Finally, she tutored him in how to gently tug it sideways into place and straighten the straps.
“Wonderful, sweetheart! Now you can put on your own bra all by yourself!” she praised him.
Josh smiled weakly. Standing in his pretty lavender bra and panty set, he was once again a complicit and willing partner in his own sissification. His mother beamed at him. “Thank you Mommy,” he said as the familiar heat reddened his face. How many sets of undergarments did he have now? Was it three or four? He was losing track of all the girly and feminine items he had suddenly acquired. His old jeans and tee shirts seemed like something from long ago.
He had seen the blue garment lying on the bed. It was very feminine, but it didn’t look exactly like a dress. It was a baby blue color with a summery floral print design all over.
Seeing his puzzled expression, Gwendolyn explained. “Josh honey this is a girls romper. It’s just a little more casual and functional than a dress but still very fun and sweet. I think you will like it.”
“It’s very pretty, Mommy,” he agreed. He was embarrassed to admit he had been wondering about something else though. Haltingly, he asked, “Mo--, Mommy… should I wear my tights again with the romper?” The sensations of his ruffled tights had left a lasting impression on Josh. He vividly remembered the confusing feelings of confinement and friction… so similar to the feelings he remembered from his dream. They made him feel tingly. He was… curious… to wear them again despite how sissy they were.
Looking at her son questioningly, Gwendolyn paused to think for a moment. Then she decided, “No I don’t think so dear. Those are really when you want to be a tad dressier for a little more special occasion. Let’s be more casual and comfy today.” His question surprised her, but she managed to keep it from showing. If she was reading this correctly, then perhaps… something was taking hold. Perhaps it was better in this one instance to draw it out more slowly. The possibility pleased her immensely.
Josh was somewhat relieved by her answer, but he also felt a twinge of something else. He couldn’t describe it exactly. He asked himself if it was disappointment. “No,” he thought. “I was just curious,” he concluded, convincing himself. As his mother held his romper out for him to step into, Josh realized that it was a one piece garment like a pair of shorts sewn to a girly top. As she helped him pull it into place, Josh was very aware of the elastic at the shoulder and sleeve cuffs which created puffy short sleeves. Turning to his mirror, he saw it had a squared neck and the chest (or bodice as he now knew it was called) was very fitted and clingy, which accentuated the puff sleeves. The shorts seemed very short to him, and they were loose enough that they might be mistaken for a skirt at first glance. Overall, though, he had to admit it seemed more comfortable for moving around in than his dresses.
“What do you think, darling?” his mother asked.
Answering truthfully, he replied, “It’s very comfortable Mommy but still cute.” It still was much more skimpy than what a boy would wear, and he was again keenly aware of how delicate his frame was. He knew he looked like a girl. “Thank you for my pretty new romper.”
Gwendolyn appreciated that even in this more casual outfit, Josh looked every bit as girlish as before. She couldn’t help it. She loved seeing him this way. “You are just so cute honey,” she complimented him with pride.
Embarrassed, Josh was still standing there gawking at his reflection when Kathy bounded in. “Oh my Joshy, I just love that romper on you!” His sister smiled admiringly. “It’s such a sweet look, and it fits you so nicely! I can’t believe I never noticed how petite you are!” Now he blushed more noticeably.
“Thanks Kathy,” he stammered.
“Kathy you’re just in time. Why don’t you start teaching Josh how to do his own hair while I pull together some breakfast and make a phone call?” Gwendolyn asked.
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sissyboy1212, Josh is getting more girly each and every day. Now, he has a romper to wear. I'm sure that he will enjoy it as much as his dresses. Keep going, kid. You are doing a fantastic job with this story.
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I can’t wait until the pull-ups are introduced, perfect with a romper.
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PART 31
Kathy went busily to work, and soon Josh was seated at his vanity learning how to comb and brush his hair into a passably feminine style. Kathy helped him select a pale blue barrette with a plastic flower on it that matched his outfit. With her help, he fastened it into place on the side of his head and left a few strands of his brunette hair falling sweetly across his forehead. She couldn’t resist giggling a bit as she spritzed a little hairspray to hold it in place. Looking in the mirror, Josh saw that he was now a full participant in his own sissification.
“You look adorable, Joshy” Kathy exclaimed. “You’re a natural!”
“Thanks sis,” Josh replied. He felt both embarrassed and a little appreciative. Her compliment was sincere.
Then she surprised him again. “Be still,” she said mischievously, "I want to try something." Kathy reached in her pocket and pulled something out behind him. Then, as he watched her in the vanity mirror, she brought a small pink brush to his lips and stroked them delicately. Josh sat motionless as Kathy coated his lips with pale pink lip gloss and then had him pucker them together. “That color is ‘Sky Pink,’ and I wanted to see how it looked on you,” she said cheerily. “It’s just a hint of color and shine… but not too much,” she explained. “It looks cute,” she concluded. “Younger girls shouldn’t wear much makeup, but a little done right is just fun. This brand stays on really well, so it should last you most of the day without rubbing off,” she added helpfully. “Don’t you love it?” she asked.
Josh stared in the mirror at his shiny lips. Another girly “first,” he couldn’t help but think. He was wearing lip gloss, and Kathy was right. It wasn’t super obvious at first glance, but it was definitely different. His lips were noticeably shinier with a tad more color, and they felt very slick. He felt so girly. “Thank you, Kathy. It feels nice.” He tried to sound sincere — he didn’t want to hurt her feelings.
At Kathy’s insistence, Josh then slipped back into his white sandals with the little flowers on top for the outfit’s finishing touch. Looking again in the mirror, he looked like a girl from top to bottom. He wiggled his open toes in the dainty little patent sandals. He was wearing yet another bra and panty set and a girl’s romper dress. His baby blue flower barrette nicely complimented his brunette hair and glossy lips. The now-familiar sight of a tween girl stared back at him from the mirror. He was dressed perfectly for a casual day at the beach. It was a little disheartening to see how little effort it took to make him look like a sweet little girl, as if that was his natural state. But still, he rationalized that this wasn’t so bad. Feeling a little more comfortable, he thought that maybe he’d gradually get back to more boyish outfits in time. Then, he noticed his lavender bra strap with its delicate white lace showing just a bit. He adjusted it quickly back under his puffy sleeve so that it was hidden again.
“You’ll have to watch out for that today,” Kathy grinned at him. “Can’t be showing everyone your pretty underthings!” Josh blushed shyly, as he realized she was right.
As Kathy and Josh came in for breakfast, Gwendolyn was just getting off the phone. “Great news,” she said happily. “Andrea can take us all this morning at her beauty salon. I told her we’d be there right after breakfast. Isn’t that wonderful?”
Josh had momentarily forgotten about all those other plans. Now, his new reality came crashing back. Being dressed as a girl around his mother and Kathy wasn’t so bad, but going out in front of other people was nerve-wracking. He had hoped that he wouldn’t have to worry about the hair salon until later in the week, or maybe he could still avoid it altogether. With a sinking feeling, he realized those hopes were dashed. He picked at his oatmeal with a sense of looming dread.
“Just think Josh,” Kathy said excitedly. “I bet you’re going to look even more adorable with a new hairstyle! I can’t wait to see what Miss Andrea has in store for you! Isn’t it exciting?” she gushed.
His stomach fluttering, Josh somehow managed to smile back at his sister and say, “Ye--, Yes Kathy.” He gulped hard, and then added, “I can’t wait.” An appointment in a ladies hair salon just was such a completely girlish thing. He regretted now that he had avoided getting a haircut for so long. His hair was full and nearly shoulder length. He thought he was being a rebel. He again had the sensation of something important slipping away from him, just out of his grasp. He couldn’t help but reach up to touch his hair and lightly brush his pretty barrette. He wondered nervously what awaited him today. Miss Andrea had seemed eager to work on his hair yesterday and give him a “proper haircut.” He shivered slightly as he recalled her enthusiastic words: “I’d be happy to put him in my chair!”
For the last few days, Josh had been waging a constant internal battle trying to cling to his vanishing masculinity. In this moment, however, the idea of just surrendering to the onrushing wave of girlishness seemed to take over his thoughts. He had already surrendered on the outside. After all, Kathy believed he wanted to do this, and he had stopped overtly pushing back on his mother since the spanking a few days ago. But he was still fighting on the inside. He didn’t want to be a sissy. He still believed that he would get through this and somehow be the same teenage boy again. He clung tenaciously to that hope. But now, for a moment, he truly considered for the first time just caving in. He immediately tried to dismiss the idea and promised himself he would never do that. Nonetheless, there was now a new crack in his mental resistance.
Meanwhile, Gwendolyn was over the moon. She and Kathy had managed to do a fair enough job with his hair in its current state, but she was eager to see him with a suitable girl’s hairstyle. It was still somewhat boyish despite their best efforts, but that would happily change today. She delighted for a few moments in imagining various cute hairstyles on him. She could see her son’s nervousness as he fidgeted in his darling little romper, and she realized he must be having similar thoughts. Then, she noticed something different.
“Josh, are you wearing lip gloss?” his mother asked him.
Before he could answer, Kathy piped up, “I let him use some of mine Mom. I hope it’s OK.”
“Oh it’s fine dear. Josh, it actually looks rather sweet on you. It definitely makes your lips look fuller. But both of you should remember a little bit goes a long way with makeup. Neither of you need much.” Gwendolyn advised. “It’s generally not hygienic to share lip gloss though, honey. I mean you wouldn’t want to share your toothbrush would you? We will get you some of your own,” she told him with a grin.
But then Gwendolyn saw something else amiss, and her expression clouded. Seeing this, Josh doublechecked his lacy bra straps. They seemed to be in order, though, tucked away under the cute elasticated sleeves.
“Knees, Joshy,” his mother said softly but firmly.
The romper-clad boy’s face reddened, and his knees instantly flew back together. Gwendolyn thought to herself that breaking this budding little bad habit might require some additional measures. For now, she retrieved her pewter compact case from her purse and tucked it between her feminized son’s knees.
“Please hold that while you finish your breakfast dear,” she directed. Now blushing furiously, Josh clasped the makeup case between his knees as he grew more anxious about his imminent hair appointment. For some reason, his “little man” perked up and rubbed against his panty liner.
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sissyboy1212, that was another great chapter. Poor Josh will be on his way to his hair appointment soon. Can't wait to read what style he will get. Keep up the good work.
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PART 32
The morning flew by in a blur. Before Josh knew it, Kathy was excitedly leading him by the hand into Miss Andrea’s salon. It was decorated with soft pastels and looked very modern but extremely feminine. Soft contemporary music played in the background. Definitely a place that didn’t have many male customers.
Andrea greeted them as they came in. “Good morning ladies! We’re all ready for you!” she said cheerily. “Kathy, this is Gina and you’ll be with her,” she gestured to an attractive younger lady dressed very fashionably.
As Kathy went off to a different station with Gina, she called, “Have fun Josh! I can’t wait to see you later!” Josh smiled weakly as his sister bounced away, leaving him with just Miss Andrea and his mother.
“Gwendolyn, we have a few minutes before Jessica is ready for you. I understand you just want a trim, so you can help us choose a nice style for Josh,” Andrea added. Turning to Josh, Andrea said with anticipation, “And of course, you’ll be in my chair. We’re going to have such fun! By the way, that’s a cute little romper, Josh. It suits you. And your sandals are simply precious!”
“Thank you Miss Andrea,” Josh replied softly, “Mommy gave them to me.”
“I love the little white flowers,” she said kindly. ”And your lip gloss is very pretty. It’s sweet but understated,” she observed. “What shade is that?” she asked sweetly.
“Uhh… it’s Sky Pink, Miss Andrea,” he replied, somewhat embarrassed that he knew the answer to that question. He thought glumly that boys should know about football and video games instead of lip gloss and panty liners. He let out a small sigh.
There were several stations in the spacious salon separated by partitions which gave each client some privacy although they were all open to the central area. She led him to her station at the very end. It appeared they were the first customers of the day. He had butterflies in his tummy and soon he was seated in a large salon chair with white leather cushions and gleaming chrome metal accents. As he sat in his romper awaiting the unknown, Miss Andrea pumped a pedal and raised the chair several inches higher. The elevated chair made him feel so small and exposed as if it was going to swallow him up.
“Well Josh, I know you want to look more feminine, so I can certainly help with that,” Andrea said as she gently removed his blue barrette and placed it in a little tray on the counter. Running her fingers through his hair, she commented, “You’re lucky your hair is nice and thick, and you have a little natural curl. I have some ideas, but did you have anything in particular in mind?”
“Uhhh… “ the flustered boy’s voice trailed off as he looked at his mother.
Gwendolyn piped in, “Well he has been reluctant to get a haircut, so it’s obvious he likes it long. We definitely want to preserve the length. I also think he’d like something versatile so he can change up the styles for different occasions. Isn’t that right sweetheart?”
“Uhh yes Mommy, that’s right. I’d like to keep it longer please… if you think that’s best,” Josh replied almost pleadingly. He had no idea about girls’ hairstyles, but maybe he could wind up with something that wasn’t too overtly girly. Ruefully, he knew he had already made his decision.
Andrea said enthusiastically, “I’m so glad you said that honey. That gives us lots of fun choices for you! I think we’ll enhance your natural waves and boost the volume. We’re going to frame your delicate facial features nicely but add a little bounce. And I want to make sure you keep those lovely bangs. What do you think?”
Realizing that he was well and truly stuck, and catching Gwendolyn’s eye, he replied timidly, “Yes Miss Andrea. That will be wonderful! Whatever you think is best.” Why did he say that? He basically gave her free reign to do as she pleased with his hair. He only had vague ideas what most of these terms meant, but they all sounded extremely girly.
Nodding eagerly, Andrea assured him, “Thank you Josh. I think I know just the thing. You’re going to look adorable! Yesterday, I wondered if you might want more of a unisex style, but I’m glad you trust me. Instead, we’re going to go for something really trendy and cute. You’ll be able to wear it up or down. All the other girls will be jealous!”
Turning to Gwendolyn, she explained, “I’d like to add some highlights too, will that be OK? I just want to lighten the color a bit. I’m going to make you so pretty Josh!”
Gwendolyn beamed back, “Oh of course Andrea. I’m sure Josh will love that. You’re the expert and we’ll trust you!” Returning to Josh, she asked him “Doesn’t that sound great honey?”
Now starting to blush, Josh felt cornered by his own words and choices. It didn’t escape his notice that a subtle shift had taken place, and Miss Andrea was referring to him as a girl. “Yes, Miss Andrea,” he gulped. Then, seeing the expectant look on Gwendolyn’s face to elaborate, he reluctantly added, “I’m so excited to see how it turns out. I’ve never had highlights before.” He squirmed mousily in the padded salon chair.
As Andrea moved to fasten a baby pink nylon cape around Josh to get started, Gwendolyn asked her to wait a moment. “Andrea, we’ve actually been working on his posture and deportment, and it occurs to me we might be able to do two things at once if it’s OK with you. He’s going to be in the chair for a while, right?” Gwendolyn inquired with a tad of mischief. Josh thought he knew what was coming.
“Oh at least two or three hours,” Andrea replied as she wondered where this was headed. “We’re going to do a shampoo and style cut. Next we’ll add the highlights. Then we’ll see where we are and decide how to finish things off,” she explained. Hearing all this, Josh’s spirits sank as he realized what an involved process he was in for. Instinctively, he pulled his drifting knees together and tried to sit up straight. Belatedly, he saw that he had been slouching again.
Gwendolyn, on the other hand, was enthused about her wayward son’s next steps into sissyhood. And what she did next would only enhance it. She reached into her purse and pulled out… not the familiar pewter compact case… but two very feminine ladies silk scarves. One was a rose pink and gold color pattern, and the other was purple, teal and light gray. Puzzled now, Josh watched nervously. As she took the first one and folded it several times diagonally, she explained, “Josh has been trying to learn to sit more like a young lady and keep his knees modestly together, isn’t that right dear?”
Seated in the chair, Josh pulled his knees together more tightly and remembered to fold his hands daintily on his lap. “Yes Mommy. I’m learning how to keep my modesty,” he nearly squeaked. He thought he understood now what she intended. He sat there motionless with a sense of dread.
“You simply must get in the habit of sitting more modestly honey, OK?” his mother asked in a way that was not really a question.
“Yes Mommy of course,” he answered meekly.
With that, Gwendolyn looped the scarf under his knees and drew them closely together with the pink scarf. She then tied them firmly together with a secure double knot. “This will help you get used to keeping your knees together dear,” she chided him. As the teen’s face began to warm, she used the other scarf to tie his ankles together for good measure. She stood back to examine her work approvingly.
Feeling utterly helpless and weak, a fresh wave of humiliation crashed over the feminized teenage boy.
“Oh my,” Andrea said quietly with increasing interest.
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sissyboy1212, Josh is really in a fix. Miss Andrea is going to have fun doing his hair into a girl's hairstyle. He didn't know his mom was going to use the two scarves to tie his knees and ankles together so he would sit more demurely. Great job on this chapter. I can't for more.
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PART 33
Andrea watched this entire exchange take place with fascination. “That should surely help with your posture dear. But are you comfortable that way?” she had to ask.
Glancing at his mother, Josh replied cautiously, “Oh yes Miss Andrea. Mommy has been teaching me how to sit more appropriately. This will, uhh, help me remember,” he added spinelessly.
In her profession, Andrea often was privy to odd or unusual things dealing with her various clients. Josh didn’t seem to object to his treatment. As long as he was OK with it, she had no issues. It certainly didn’t shock her, and it was far from the strangest thing she had seen in her career. Hairdressers had to be discreet if they expected to stay in business. Honestly, it piqued her interest. Then, she thought of one of her other clients and hatched an idea. “You know Josh, since you’re going to be in the chair for a while anyway, we can really do it right if you like,” she said.
It was now Gwendolyn’s turn to be keenly interested, and Josh grew more apprehensive. His knees and legs were already trussed together. What did she mean to “really do it right?”
Andrea explained as she pulled open a drawer, “I have some extra accessories for this chair I use for one of my other customers. She is a wonderful lady with a motor disorder. She was in a car accident years ago, so we have to strap her into the chair when I do her hair so she doesn’t slip down. She tires very easily. She has a great sense of humor, and we actually joke about it now. But the truth is it makes her much more comfortable when she gets her hair done. It allows her to keep sitting upright in the chair during her appointment, and this might work for you too. Sit up straight dear.” As she said this, she reached over and buckled a thickly padded seat belt across Josh’s lap and pulled it snug.
“Now hold still, please,” she instructed. Andrea then pulled two matching shoulder straps down on each side and fastened them across his chest to the lap belt. The padded straps were all white in color and matched the chair. She pulled the straps taut to take out the slack and then fastened everything with a sort of buckle behind the chair. Josh was now pulled securely against the back of the chair. “This will help you sit up straight while we do your hair, honey. Is that comfortable?” she asked the now-confined sissy, “See how it gives you so much better support?”
Josh was in utter disbelief. How had he gotten himself in this situation? He was now basically tied to a chair for a girly hairdo, and the worst part was he had agreed to it! Blushing furiously with embarrassment, he also realized that his little man was wide awake. This feeling of being confined and helpless was making him feel extremely odd. He immediately recalled his dream two nights ago.
“Yes Miss Andrea,” he could scarcely believe the words coming from his mouth. “It’s comfortable,” he said breathlessly. Why couldn’t he just summon the words and tell her to unbuckle him?
“Well if you get tired or uncomfortable, honey, just tell me and we’ll loosen those up a little, but it should really help you as you work on your deportment,” she reminded him. Hearing this, Josh realized that all he had to do was say the word, and he would be let out of this predicament. But, to his shame and confusion, he realized he couldn’t do that. Something inside him was holding him back. What was going on?
In the end, despite his internal conflict, he only replied, “Yes Miss Andrea.”
Gwendolyn was amazed. The sight of her feminized son strapped in this way to get his first girly salon hairstyle was exhilarating, truly beyond anything she had considered before. “Well, this should make for a memorable hair appointment, right Joshy?” she joked with him.
He smiled wanly and nodded his head. His heart was racing at this odd turn of events. Then Gwendolyn noticed some additional straps on the vanity that Andrea hadn’t used. “What are those?” she asked.
“Oh I don’t expect we need those for Josh. Some days are worse for my other client than others. If her tremors are acting up, then we sometimes use those to hold her arms in place,” she explained. “If you’re curious, I can show you how they work Josh,” she added.
The discomfited boy was feeling a little lightheaded at this point. “Uhh… OK sure,” he said shyly, almost automatically, deeply ashamed of himself.
Shrugging, Andrea attached the wide padded straps to the arms of the chair. Then, she pulled them over Josh’s slender arms and rapidly cinched them down. She finished by securing them snugly in place with several thick Velcro straps. It was immediately apparent to Josh there was no chance he would slip out of this on his own. Almost as an afterthought, Andrea reached down and he felt another wide strap being pulled across his already-bound ankles to hold his feet in place against the footrest. Josh was effectively immobilized in the chair. “See how that works?” she asked him, “It’s actually kind of comforting for her when she has bad tremors… sort of the same effect as those weighted blankets which are in vogue. She says it can actually be quite relaxing.”
Gwendolyn was intrigued, and said “That should help him cut down on all his fidgeting. Very interesting!” It was amazing to her how much more docile Josh seemed than even earlier this morning.
Just then, a new voice called from the reception area, “Mrs. Hartley, this is Jessica. I’m ready for you now.”
Gwendolyn looked one last time at her helpless son’s predicament, and said, “have fun dear!” Thinking of all those times before that he had darted away with his hooligan friends when he was supposed to be doing homework or chores, she couldn’t help but add with a chuckle, “Now don’t wander off darling. You sit still and let Miss Andrea give you a pretty hairstyle.” His face beet-red, Josh sat helplessly as Miss Andrea drew the pink nylon cape around him and snapped it snugly around his neck. Andrea hadn’t even bothered to ask him if he wanted to be released from the arm straps. She seemed to already sense the answer.
Gwendolyn savored the sight of her son completely enveloped in this femininity. Her plan to meticulously root out all his boyish bad habits and replace them with girlish sweetness was producing highly satisfactory results. Before Gwendolyn departed to meet Jessica, she snapped some photos with her phone. “I want to capture the ‘Before’ and ‘After’ shots,” she concluded.
Andrea laughed and replied gaily, “I suppose I’ve got a captive audience today.” She playfully tapped Josh on his nose with her finger as she said this, and he blushed more furiously.
Once Andrea had the long cape on him and all the straps were hidden from view, she seemed to forget about them. His knees and ankles were tied together with his mother’s ultra-feminine scarves, and the various padded straps held him securely to the salon chair. Andrea slowly swiveled the captive teen around to face the mirror and brushed his long brunette hair out of his eyes with her fingers. It was like being buckled into a roller coaster as it climbed up the first big hill. His heart beat in anticipation of the coming plunge.
“Well let’s get started, shall we sweetie,” she said to Josh with anticipation, “you’re going to look simply adorable when I’m done with you!”
She spun her new charge back around and gently reclined his head into the sink to start his shampoo. The waiting was over. Powerless to resist, the helpless teenage boy grew slightly dizzy as she began rinsing his hair with the soothing warm water. A wild mix of pleasure and humiliation assaulted his senses. Soon, the delicate smell of a fancy feminine shampoo tickled his nostrils. Miss Andrea hummed softly as she massaged it into his hair. He felt a familiar tingle in his panties.
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A salon trip and hairstyle change has long been one of my favorite sissy scenarios. While not permanent, I've always felt it adds a sense of permanence to the whole affair. "If they're doing my hair, they must be planning to keep this going" type thing. I'm sure Josh will realize that soon if he hasn't already. He's slipping so well into sweet femininity
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Andlat,
Thank you and I agree. A new hairstyle is not irreversible, but psychologically it represents a new level of effort and commitment. All the delicious trappings of a ladies hair salon heighten the experience. I love the idea of him getting trapped deeper and deeper in his new feminine world.
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Andlat,
Thank you and I agree. A new hairstyle is not irreversible, but psychologically it represents a new level of effort and commitment. All the delicious trappings of a ladies hair salon heighten the experience. I love the idea of him getting trapped deeper and deeper in his new feminine world.
It's so true. Mom's not going to pay for a barbershop visit to get his hair back to a boy's style so soon after this trip to the salon. I'm especially excited to see just what style he ends up with!
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sissyboy1212, Josh is going to have a very pretty, feminine hair style. He is all strapped into the chair and the process is beginning and he is helpless to stop it. Sounds like fun to me.
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Very good story so far. I hope you will be able to continue it at some point.
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Poor Josh. It must feel to him as if he's been at the salon for over a month! ;)
I tease, but I felt the urge to revisit this story today, which has only made me all the more excited for its eventual revival!
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I will definitely continue this story at some point. I still have the outline of how it will continue and end up. But real life health issues for family members makes it impossible right now. Too many things happening at once (COVID-related). Everyone stay safe and wear a mask--preferably a pink one ;)
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sissyboy1212, You take care and be safe with this COVID crap going on. Always wear a mask and jump people's butts that don't and put everyone in danger of catching this deadly virus.
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PART 34
Josh felt as though he were slipping into a trance while Miss Andrea gently but methodically shampooed his hair. Unable to move, his thoughts raced and his pulse quickened as she deftly worked her fingers through his hair. Trapped in this ultra-feminine salon, the teenaged boy knew he was taking yet another step to becoming a total sissy. He thought regretfully about how he had let his hair grow longer so he could look cool in front of his friends. Still, he couldn’t deny how pleasant it felt to be pampered like this.
Continuing to hum, Miss Andrea finished the shampoo and rinsed it out with the warm water. Seeing that he was enjoying the shampoo, she said “That feels good doesn’t it sweetheart?”
Answering truthfully, Josh replied “Yes Miss Andrea, it feels really nice. Thank you.”
“Next the conditioner,” she informed her charge. “It’s important to use a high-quality conditioner so we can get that nice lustrous shine.” She smiled down at him and started to work the conditioner into his long hair. “You’re so lucky to have such lovely hair. It gives you so many cute options.”
“Thank you Miss Andrea,” Josh squeaked.
She repeated the process and was soon rinsing the conditioner out with the water again. She turned off the water and began to pat his hair dry with a fluffy white towel. By this point, Josh was disappointed that the nice massaging had to stop. His little man was fully awake and straining against his panty liner by this point. He knew his pretty lavender panties were bulging underneath the romper. Absent-mindedly, he realized that his little man was buried under four layers of girlishness: his panty liner, his panties, his floral girls romper, and finally the pink nylon salon cape. It was a mental picture that seemed to sum up his predicament perfectly.
His thoughts were interrupted when Miss Andrea raised the seat back up and returned him to a sitting position. Josh squirmed slightly as he tried to relieve the pressure on his groin, but all the straps and belts did not allow much movement at all. The silk scarves ensured his knees stayed close together which only made the tension worse.
Seemingly oblivious to everything happening under the cape, Miss Andrea towel-dried his long hair until it was just slightly damp. She then combed it very carefully all the way out. It was hanging well over Josh’s eyes in front and was nearly touching his slender shoulders in back. When she had it all combed out, she picked up her scissors.
“Now is the time for the real work to start,” she said cheerily. “We’re going to make sure we preserve the lovely length, and we'll do some cute layering,” she continued.
Josh sat helplessly as she began to comb and snip his hair. She was much more finicky and measured than the barbers that had always cut his hair before. She worked her way repeatedly back and forth in his damp hair—a tiny snip here, a comb there, then another tiny snip. It was mesmerizing. He was turned away from the mirror so he couldn’t really see what she was doing. He caught an occasional fleeting glimpse of himself in the mirror on the other side of the room, but with his bangs combed over his eyes and Miss Andrea stepping in front of him he was mostly clueless. Through it all, Josh’s little man was in a perpetual state of tension as his emotions ricocheted haphazardly from anxiety to pleasure to embarrassment to dread.
After what seemed a long time, Miss Andrea seemed to be done with the scissors and began to alternate between combing and gentle brushing. As she fussed with his hair, Josh felt the now-familiar weight of hair clips being placed in his long hair. “I’m sectioning your hair now so we can do your highlights, sweetheart. You are just going to be precious!” she explained. As she talked, Josh felt the weight of more hair clips being added. “Have you ever had highlights before, Josh?” she asked.
“No Miss Andrea,” Josh stammered. As she stepped away, Josh saw himself clearly in the mirror for a moment. His head was now covered in bright pink hair clips which divided his hair into small neat sections. He looked so small and girlish with all the hair clips and the pink cape fastened around his neck.
“Well these will add some lovely texture and depth to your style. The other girls will be so jealous!” she added enthusiastically. As she spoke, she began stirring a solution in a small ceramic bowl which gave off a slightly chemical smell.
Josh felt his face redden as that thought sank in. Acutely aware that his hair was being transformed into an unmistakably girlish style, he felt a new sense of deepening permanence. All this girlishness felt more and more irreversible, and it was all his choice. Even if he somehow returned to boys clothes, his hair would remain girlish unless he got a crewcut or something. He shuddered as he knew that he was either going to have a girly hairstyle for the foreseeable future or be forced to look like one of those Sterncourt boys from the brochure. His faint hopes for a longer haircut that looked “cool” on boys slowly evaporated as he stared at all the pink clips in his carefully sectioned hair.
“Here we go!” she said playfully as she swiveled him away from the mirror again. Josh saw she now held what appeared to be a small piece of aluminum foil. She put it on top of his head, and he felt her separating a strand of his hair. Holding that in place, she took a small brush and dipped it in the bowl. She then seemed to brush it onto his hair as if she was painting. Next, he felt her tugging, folding and clipping it firmly in place.
“One down,” she explained, “Only about twenty more to go!”
“Twenty?” Josh thought to himself. His pulse quickened and his face grew even warmer as he now understood just how involved this process would be. His little man perked up again in his panties. Instinctively, he tried to reach down and adjust himself to ease the pressure, but the padded straps still held his arms firmly in place. He felt so sissyish, and he could only sit meekly while Miss Andrea started on his next highlight. The shoulder straps held him snugly against the salon chair and a small bead of sweat trickled down his back. The teenager sighed inwardly as she reached once more for her paintbrush.
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Oh, my! You know just how to focus on every detail as Josh's hair gets oh so methodically done. A wonderful addition, so very well worth the wait!
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sissyboy1212, Josh is really get the treatment at the beauty salon. He is going to look oh, so cute with his highlights. Can't wait for the next chapter.
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PART 35
Working methodically and efficiently, Miss Andrea soon covered the sissified teen’s head in neatly folded foils. As she brushed in the last highlight and folded it into place, she said with satisfaction, “I put in 22, Josh. They will really turn out beautifully I think. I’ll bet you can’t wait to see how pretty you will be!” As she spoke, she turned Josh back to face the mirror.
Grimacing, Josh replied with more enthusiasm than he felt, “Oh yes Miss Andrea, I’m so excited to see how it will look.” Still strapped securely in the padded chair, he gawked at his reflection. His head was completely covered in the small foil squares, and he could only imagine how girlish the final result would be. While he watched in the mirror, Miss Andrea fitted a plastic pink bonnet that looked like a shower cap over his scalp. The pale pink bonnet had little flowers on it and an elastic headband that fitted snugly against his scalp. He noticed belatedly that the cap had a flexible tube attached to it which led in turn to a small machine.
“This is a relatively mild highlighting agent,” Miss Andrea said. “I only use the milder solutions on younger clients to minimize any hair damage. I’ll set the bonnet on a low heat setting just to add some warmth and make the solution work faster.” Setting a timer, she told him, “I’m going to check on your mother and sister and I’ll be back in a few minutes, dear—don’t wander off!” she winked at him. Before he could respond, she turned on the machine and the bonnet immediately filled with gently blowing warm air. He watched powerlessly as she stepped away from the station leaving him confined in the salon chair.
Although he could hear muffled voices elsewhere in the salon, the whirring noise of the machine and the rush of blowing air made it impossible to make out what anyone was saying. Josh was trapped in his own thoughts as the warm air and the chemicals did their work. He couldn’t avoid staring at himself in the mirror, and he realized just how far down the road to girlhood he had traveled. The pink bonnet billowed with the warm air around his head, and it was quite an odd sight to see himself covered completely in pink femininity with only his face visible.
This was all such a new and foreign experience. Despite himself he was becoming more unsettled as the totality of his new situation dominated his thoughts. He shuddered and tried to shift in the seat to get more comfortable, but the straps held him fast. He wiggled his knees a bit but the scarves and straps held his legs clasped closely together and firmly against the footrest of the chair. All he succeeded in doing was agitating his little man again… worse than before.
He closed his eyes and tried to relax. He reminded himself that he had made this choice. He took a deep breath. This was still better than being at Sterncourt, and he had to admit to himself that all the girlish pampering did kind of feel nice. Plus, he was still struggling with the notion down deep that he liked the feeling of being strapped in the plush salon chair. What did Miss Andrea say earlier, that it was kind of the same effect as a weighted blanket? As his thoughts drifted, he began to grow drowsy from the whirring noise and warm air of the bonnet. With his little man still fully at attention, Josh dozed off.
He was confused for a moment when he realized that he was deep down in the plush pink pillow again. He wasn’t bouncing like before. Instead, he was cocooned inside. It felt so soft and comfortable and warm. He shifted around a bit and the cocoon shifted with him. He realized he was wearing the enormous frilly pink petticoat again and it seemed to swallow him whole. He could feel immediately that he was also wearing a clingy pair of white girls tights. The familiar friction of his tights under his petticoat was immediately recognizable. And he was also wearing a scoop neck white leotard top with short cap sleeves. His floppy pink hairbow had somehow doubled in size and it was now giving off a pleasant warmth. He could see a dim light far above his head, and it dawned on him that must be the way out. If he could just make it to the light, he could dress like a boy again.
He began climbing toward the light but quickly realized he was trapped in the pink cushiony cocoon and his preposterously huge petticoat. His arms and legs were completely wrapped in a tangle of pink satin ribbons, and as he licked his lips he realized that they were covered in a thick coat of bright pink lip gloss. He tried climbing harder but he was still totally stuck.
Randomly, it occurred to him that if he could just do one perfect curtsey, then he might be able to escape. Against all reason, he convinced himself that was his only way to pass this test and get out. He tried frantically to find the edges of the billowy tulle petticoat only to discover his hands were tightly encased in little pink satin mitts embroidered in white lace and securely tied off with white ribbons. Still, he attempted to cross his ankles and dip down in a dainty curtsey but it was hopeless. His heart raced as he continued to struggle, and the light began to grow more distant and fade. He called out, but his voice was drowned out by a whirring noise in the background. Breathing harder, he made one last desperate push to perform the most prissy, most adorable curtsey he could muster. He thought for a moment he could almost reach the light and then…
Ding! Miss Andrea’s timer went off and Josh abruptly woke up. Opening his eyes, he found himself still securely strapped in the salon chair. His heart thumping, Josh was horrified as his little man twitched very excitedly. For two or three seconds, Josh trembled with agonizing anticipation and tried to stop the inevitable. Then, all at once, the dam finally burst and his little man pulsed rapidly in release. Josh quivered and shuddered in the chair as a warm sticky mess quickly filled his panties. Josh remained transfixed on his girlish reflection—unable to avert his eyes. After several electrifying seconds, his little man calmed and the tingling began to subside. In the aftermath, Josh turned crimson red as he absorbed what had just happened. He now had to confront the terrible reality that he made a “little squirtie” while getting a girls’ hairstyle in a ladies hair salon. Confined as he was, he could only wait in dread for Miss Andrea to return.
Seconds later, Miss Andrea came back to turn off the machine and the whirring noise stopped. Josh was aghast to see that his mother had returned as well. As the discomfited boy sat in his gooey panties, Miss Andrea removed the bonnet and checked the progress of his highlights. Satisfied, she announced, “I think that’s just perfect.” She continued speaking to Gwendolyn, “After I remove the foils, we’ll get him rinsed out and see where we are!”
Before she began, Gwendolyn snapped another photo of Josh with his head covered in the foils as another memento of the special day. She couldn’t help but notice his furious blushing, but in an odd way it made a cute picture. “Josh, honey, isn’t this wonderful?” she asked. “I know you are going to be just darling when Miss Andrea is done with you!” she continued. “It’s so exciting to see you get your first pretty feminine hairstyle in Andrea’s lovely salon!”
Red-faced, Josh could scarcely get the words out, but he knew his mother wanted a response. “Ye-ye-yes Mommy,” he stammered, “I just know it will be so adorable.”
Miss Andrea swiveled him around and leaned the chair back into the sink so she could remove the foils and rinse his hair. Josh was still blushing and fixated on the gloppy mess which he knew filled his panties. Remembering his panty liner, he fervently hoped that it would conceal what had happened. He tried to close his eyes and calm down as Miss Andrea began removing the foils. His thoughts were a turbulent sea of conflicting emotions.
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sissyboy1212, I'm jealous of Josh. He got his hair highlighted and I know he is going to be oh, so pretty. It's funny that he had his dream again and made a mess in his panties. He is definitely going further down the rabbit hole of femininity. Can't wait for the next chapter.
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Thank you Andlat and Sissy Little Girl. Glad at least a couple of people out of the thousands that read it decided to comment. Thank you for your kind feedback.
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Alas, it is the unfortunate fate of Internet authors to not receive the thanks and appreciation they fully deserve. Speaking only for myself (but probably reflecting the thoughts of many others) I love this story and check in everyday to see if there are updates. Thank you for your wonderful contribution!
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Thank you jenniesissy! That's so true about internet writing LOL. I don't necessarily crave constant attention, but it's nice to get occasional feedback.
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PART 36
Miss Andrea removed the last foil and thoroughly rinsed Josh’s hair with lukewarm water. Despite his current predicament, he relaxed somewhat as she once again massaged and rinsed his scalp.
“Oh my!” Gwendolyn exclaimed. “His highlights are gorgeous, Andrea” she said approvingly as she took in Andrea’s work.
“Wait till you see the finished product,” Andrea agreed, “he’s going to be adorable!”
Josh’s heart sank a little at this exchange, but he was anxiously trying to think of any excuse to slip away and hide his sticky accident. “Miss Andrea, he began timidly, “Could I please use the restroom before you finish my hairstyle?” Remembering to use the proper childish term, he said softly, “I, uhh, I need to tinkle please.”
“Of course, sweetheart,” Miss Andrea replied, “Let me just wrap your hair up while you go.” She toweled his hair a bit and then raised her charge back to a sitting position. Before Josh had a chance to see his highlights, she had wrapped his head in a baby pink terrycloth hair turban. “You’ll need to keep that on while you’re out of the chair, dear,” she advised. Removing his pink cape to reveal all the straps and scarves holding Josh in place, she said, “Oh my goodness, I’d almost forgotten about these.” She began to unbuckle all the straps.
Gwendolyn smiled at her son as she reached down to untie him and retrieve her scarves. “Such an exciting day for you honey. You’re doing very well, Josh, and hopefully we won’t need these again when Miss Andrea finishes your style.” She said this last part encouragingly as if she were still making up her mind.
“Oh Mommy, I’m getting much better at my posture now I think,” Josh said hopefully. “I’ll keep trying.”
“We’ll see, dear,” his mother replied.
Finally released, Josh dared to look down and was immediately relieved that there was no obvious wet spot on his romper. Perhaps, just perhaps, his panty liner had saved him. His muscles were stiff from sitting for so long, and he was glad to stand. He was still a little weak-kneed from the straps and the thrill of his “little squirtie.”
“The ladies room is down the hall to the right, dear,” Miss Andrea directed him.
“Don’t dawdle, Joshy,” his mother added.
Josh moved as quickly as he dared to the restroom and closed the door. It was then that he realized he had another challenge: how to get out his romper. With the shorts attached to the top, he basically had to remove the whole thing to use the restroom. He found that he couldn’t quite reach the buttons in back to access the zipper. To his chagrin, he concluded that he would have to ask for help.
Opening the door, he called, “Mommy, can you please help me unzip my romper?” It was embarrassing to have to ask for help but he saw no other option.
Gwendolyn came to the door and smiled at him, “I was wondering if you’d need some help. Don’t worry, darling, Mommy’s here.” She unbuttoned the top buttons and unzipped him. “I think you can manage the rest dear,” she said as she closed the door and left him alone.
Pulling down his romper, Josh inspected his panties. Although there was a small wet spot on one side, he was happy to see his lavender panties were mostly clean. “Thank goodness for my panty liner!” he thought to himself. A second later, it dawned on him what a sissy thought that was. Still, he was grateful to be mostly dry. He dropped the soiled liner in the small garbage can and looked around. There were some scented wet wipes on a little shelf next to the vanity, and he used one of those to clean himself. They had a heavy lavender scent, but at least he was clean now. He sat down and tinkled, making sure to wipe himself carefully when he was done before pulling his panties back in place. He couldn’t afford another accident now that he had no protection.
He stood up with his romper still around his ankles and covering his cute sandals. Turning, he glimpsed himself in the mirror again. Standing in his lacy training bra and panty set and with the pink turban wrapped around his head, there was nothing about him now that looked remotely boyish. As he appraised his reflection, a deepening sense of shame took root. He was humiliated that he'd had a "little squirtie" as a direct result of being sissified this way.
He felt a sense of slight dread wondering how his hair looked underneath, but he left the turban wrap alone. He knew he’d never get it back on correctly by himself. Sighing, the emasculated teen straightened his bra and pulled his romper back up. Once again, he found he needed help getting fastened back into it.
As he started to call for his mother again, there was a tapping at the door. “Joshy what on earth is taking so long? Please don’t keep Miss Andrea waiting!” she chided.
“Uhh, I just need some help getting zipped back up Mommy,” he replied. Blushing again, he opened the door. Although she looked at him a little curiously, she just zipped and buttoned him back up.
Soon Josh was back in the salon chair. Although Miss Andrea and his mother did not strap him in like before, his mother thought it best to at least buckle his seat belt. And while she didn’t tie his knees together again, she draped the scarf over his bare legs and had him rest his hands on it “as a reminder.”
“Joshy, Miss Andrea and I have been talking, and she has another suggestion for your new look which I think is wonderful,” his mother said with a trace of amusement. “She’s done a fabulous job on you so far, and I’m sure you’ll be pleased with the result.”
Josh snapped to attention and listened intently. He had assumed this painstaking process was almost over after the shampoo, conditioner, haircut and highlights. What more could possibly be left?
“As I discussed with your mother, although you're fortunate to have a natural wave in your hair, some extra curl would frame your delicate features very sweetly,” Miss Andrea explained. “A medium perm to boost your curls would just pull the whole look together,” she continued. Concluding, she asked expectantly, “What do you think Josh?”
“I think it’s a fantastic idea, Andrea,” his mother interrupted. “I know Josh wants to turn over a new leaf with his look, don’t you honey?” she asked.
“A perm?” Josh thought unhappily. He was being given another choice, but his mother’s eyes made it clear what she wanted to hear. Feeling trapped, he already knew what his answer would be. “Uhh sure I guess. If you think it’s best I mean, Miss Andrea” he said with resignation. Catching his mother’s eye, he knew that his halfhearted response was not good enough. Cringing, he said more enthusiastically, “Oh yes please Miss Andrea, I would love to get a perm. I know I’m going to just love my curly hair!”
His mother nodded approvingly at her increasingly feminine son. Soon, she thought gaily, he would be sporting an unmistakably girlish new hairdo. With his lovely highlights and some dainty curls, she was certain he would be a picture of girlishness.
With a flourish, Miss Andrea draped the pink nylon cape around his shoulders again and said eagerly, “You’re going to love it Josh!” Turning him away from the mirror, she unwrapped his still-damp hair and removed the turban.
Josh was sure that by the time she was done, his hair would be unrecognizable. Feeling incredibly sissyish, he remembered to clasp his knees together properly under the cape as he awaited his first perm. With a growing sense of dismay, he could only imagine how girly he would look. He watched anxiously as Miss Andrea picked up a pink perm rod and then meticulously rolled the hair above his forehead. Almost unbelievably, his groin stirred again. He tried not to squirm as she pinned his first perm curler tightly in place.
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Josh just keeps going deeper and deeper, doesn't he? I'm almost as excited as he is to see his new hairdo! :)
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It's been a while since I visited Josh. Not sure when I'll add more to the story, but I felt he should at least get to enjoy his girly new hairstyle.
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PART 37
His mother smiled happily at her sissy son, and she left once again to the waiting area so Miss Andrea could work. “I’ll see you in a bit sweetheart,” she called as she left, “I know you’re in good hands!”
Again, Miss Andrea worked meticulously and precisely on her charge’s hair. Josh fretted silently as she tightly rolled his long damp hair into curler after curler. After a short time, he could feel that his hair was now encased in a girlishly restrictive mound of perm curlers. Miss Andrea smiled at him sweetly as she reached for another squeeze bottle of liquid. Josh continued to clasp his knees together closely under the pink cape.
“Now for the perm solution, dear,” Miss Andrea explained. “I’m using a mild solution since we’ve already colored your hair and we don’t want to damage it. But you are going to be so cute!” She began squirting the solution onto the teenage sissy’s curlers, and the smell of the chemical solution was noticeable.
Josh was chagrined as he grappled with the fact that this could not be undone easily or quickly. No matter what, he was going to have a very girlish hairstyle for a while. It felt like yet another irreversible step in his rapid sissification. Miss Andrea finished with the solution and used a towel to blot up the excess. Setting another timer, she said, “Ten minutes honey. Now you just sit still while those lovely curls get activated! I’ll be back in a few.”
She turned him back to face the mirror and stepped away for a moment. Staring in the mirror, Josh fixated on the lavender mass of curlers on his head. He looked so small and helpless like this. He wiggled again underneath the pink cape and adjusted his romper a bit, but he remained very mindful of keeping his knees together in case his mother returned. He could feel his pretty white sandals clack softly against the footrest. He could only imagine how his hair would look when Miss Andrea was finished, and his thoughts kept returning to her last comment about the “lovely curls” he would soon have.
Soon, the timer dinged again and Miss Andrea returned. She efficiently swiveled him back around and tilted him back to the sink. Leaving his curlers in, she rinsed the boy’s hair thoroughly with lukewarm water. Then, she took yet another bottle and applied it to his hair. “This is the neutralizer Josh dear,” she explained helpfully. She finished applying the neutralizer, and at last Josh could feel her start to begin carefully removing his curlers. She worked more slowly now, taking care to leave Josh’s new curls intact as she took out the lavender curlers.
She returned him to a sitting position and picked up her hair dryer. She put a large diffuser on the end of it and proceeded to slowly dry his hair with cool, gentle air. She worked very deliberately now, and it seemed to be taking forever.
“Ooh Josh this is even better than I had hoped for!” Miss Andrea said happily as she worked. He was still facing away from the mirror, so he could not see what he looked like, but he could now feel an unfamiliar bouncy sensation in his hair as it dried.
As Miss Andrea finished drying his hair, Josh’s mother returned. Seeing her son, she gasped audibly with delight. “Oh my, Andrea, that is adorable!” she said approvingly. Addressing her son, she added “You’re going to just love it, darling. You’ll be the envy of all the other girls!”
Horrified at that idea, Josh felt his cheeks redden. Miss Andrea finished with the dryer and looked excitedly at Josh. “Well you’ve had to wait long enough,” she said expectantly, “it’s time to let you see!” With that, Miss Andrea turned the teenage boy back to face his reflection in the mirror.
Josh was transfixed as he fully took in his new look for the first time. It was everything that he had feared. He now sported what was an unmistakably girl’s hairdo. There was nothing ambiguous or unisex about it. His brunette hair was noticeably lighter with his new golden highlights, and he now had a mass of gently cascading and exceedingly girlish curls. He looked every bit like a sweet pre-teen little girl.
“Don’t you love it Josh?” his mother asked leadingly. “It’s just adorable and it suits you perfectly I think.”
Trapped and defeated, Josh replied, “Yes Mommy I… I love it,” he said softly. “I feel so pretty with my new curls.” Josh could not escape the feeling of… permanence that overcame him now. Nothing about this felt temporary anymore. He could feel himself slipping uncontrollably into complete girlishness as he gazed at his undeniably precious new look. Strangely though, there was a part of him that... liked his new curls. Was that even the right word for what he was feeling?
“Now for the finishing touch,” Miss Andrea said as she misted his hair with a delicate spray gel and teased his new locks gently into place. “And this is a little present from me,” she added as she held out a large baby blue hairbow that matched his romper. “Your new hairstyle will be so versatile for you. I think you’ll enjoy it very much!” she concluded. She gently pulled a bunch of his curly hair to the left side of his head and clipped in the large bow which allowed some of his curls to dangle even more sweetly to the side. In the mirror, Josh could only see an adorable young girl staring back at him.
“All sugar and spice now dear,” his mother said approvingly, “What do you say?” Gwendolyn was absolutely thrilled with Josh’s darling new hairstyle.
“Thank you so much Miss Andrea,” Josh said obediently, “I just love it,” he said with more enthusiasm than he felt. But there was still that little nagging feeling inside that a part of him seemed to enjoy being girly.
“You’re quite welcome my dear,” she replied cheerily. “It was an absolute pleasure. I wanted to style your hair from the moment I saw you in the restaurant.” Miss Andrea removed the cape and Josh got up unsteadily. He was a little wobbly in his pretty sandals after being in the chair for so long and also from the emotions of taking this next plunging step into girlishness. He saw that his pretty new hairbow did in fact match his romper perfectly.
“Time to show your sister!” his mother said exuberantly.
The sissified boy’s shoulders slumped slightly as he slowly followed his mother to the waiting area, his sandals clicking softly as he stepped. Conflicting feelings and emotions swirled inside his head.
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sissyboy1212, I am so glad to see that you are continuing this story. I absolutely love how detailed you are about every aspect of Josh's feminization. From his hair, to his clothes, to his increasingly sissyish demeanor, you really have a way of selling everything, and this story just radiates such a wonderfully bubbly and prissy energy. Details like that are an aspect of my own writing that I honestly wish I was a little better at, but you are absolutely knocking it out of the park with this one. Please continue this story (at whatever pace you are comfortable with, because you don't owe us anything) because it is absolutely A+ material.
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Such a delightful tale - and a wonderful update. Closing my eyes, I could almost imagine it was me rather than Josh at the salon having my hair curled. Thank you so much for this creative, well-written story.
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The mention of the versatility of his new hairstyle is so tantalizing and makes it quite evident that Josh will have a whole variety of new girlish things to learn in regards to his new hairdo. At a certain point, one wonders if the title 'sissy boy' fits anymore and if he's more or less just become a girl, at least for the time being. I'm excited to see what comes next! In the meantime, I think I'm due for a re-read haha
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sissyboy1212,
A while back, about midway through your story I had some non-Covid medical problems and didn't check back until yesterday and started rereading your story from the beginning.
I imagined myself in Josh's place getting feminized step by step by making the choices put before me.
If I had been writing this story I think I would have pretty much followed your plot, but I might have had Mommy issue him a purse (actually a purse of the day) to carry while away from the house which contained wipes and extra panty liners in case a "squirtie" happened, in the same way that girls need to carry wipes and pads when Auntie Flow makes her monthly visit. An additional requirement to report to Mommy when making a ladies restroom request would be mention of needing to change his panty liner.
New required purse contents could be added such as a hair brush and tube of lip gloss.
I really like your pace and level of detail.
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CuddleBunns, Jenniesissy, Andlat, and dolly bo peep,
Thank you all for the lovely comments and feedback. I've also very much enjoyed reading the stories that you write. I just try to put myself in Josh's panties and imagine what I wish would happen to me too :)
Andlat thank you. I rather enjoy thinking of Josh as a sissified boy instead of a girl, but your point is well taken LOL.
dolly bo peep, I hope your medical issues are minor and improving, and the idea about the purse is cute. I have the idea for the next chapter, but finding the time is challenging. I do have some other adorable surprises in store for him when I get around to it :)
Thank you all again.
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I decided to go ahead and work on the next part.
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PART 38
Upon seeing her brother’s new golden curls, Kathy squealed with delight. “Josh it’s so pretty! I love the way your curls just bounce and shine! You are just the cutest!” she gushed.
Josh noticed Kathy’s hair also looked very nice, but her style wasn’t much different than what she wore before. She still had an understated lob cut that looked more fashionable and trendy. Josh realized that Kathy’s hair looked much more mature than his did… just like an older teenage girl who was growing up. It was obvious that he had the little girl’s hairstyle while his little sister looked much more like a young woman. “Thank you sis… your hair looks great too Kathy,” he finally managed to respond.
“Thanks Joshy!” she replied happily.
Gwendolyn insisted on taking several photos of her two children and their lovely new hairdos, so Josh was forced to smile prettily with his sister for the camera. Gwendolyn noted with satisfaction that Kathy clearly looked like the older sister now, especially with her height advantage on her sissified brother.
Josh was acutely conscious of the way his new curls bounced and danced gaily on his head. It was unlike any haircut he had ever had. He turned and caught another glimpse of himself in a mirror and was surprised again by how girlish he looked. Almost mesmerized, he reached up and gently brushed his pretty new blue hairbow with his hand and then touched one of his springy new curls. He tugged it slightly but it immediately popped right back into place.
“Careful dear,” Gwendolyn chided him gently. “You don’t want to ruin your cute new hairstyle after all Miss Andrea’s work.”
Andrea chuckled and said, “Well that’s really the advantage of a perm. As long as you keep your hair conditioned and cared for, those precious curls will just spring right back!”
Josh wasn’t sure if this was supposed to make him feel better, but it just reinforced that he would be stuck with this girlish hair for a while. He sighed softly. Just like the name promised, it was basically permanent.
While Gwendolyn settled up with Andrea and spoke with her a few more moments, Kathy grabbed her brother’s hands and squeezed excitedly. “It’s just like having a cute little sister now!” she said happily. Josh could only smile weakly.
Since it was almost lunchtime, Gwendolyn said that they should get something to eat since they had been in the salon all morning. They walked across the street to a charming little café with outdoor tables and had some nice sandwiches. The waitress was a younger woman named Gina and she complimented them on their nice outfits and hairstyles.
“I especially love your curls, sweetie,” she said nicely to Josh. “They’re just adorable!”
“Thank you,” Josh replied bashfully as he subconsciously touched his hair. He realized that she had no idea he was a boy, and in a weird way he was actually grateful for that. Apparently the town gossip about the sissy boy hadn’t reached her yet.
It was a beautiful spring day, and Josh felt as if he was on display as there were a lot of people walking around in the nice weather. Their table was next to the sidewalk, and there was really no place to hide. Josh realized the cafe was only a couple doors down from Mrs. Smyth’s dress shop. He was pained to remember that was going to happen soon as well. Sighing, he silently hoped that she wouldn’t come by and see them. Mrs. Smyth’s words to him in their initial encounter leapt back into his thoughts: “I can’t wait to get my hands on you, my dear!” He shuddered involuntarily.
While they finished the sandwiches, one of the teenage boys he had seen on the beach the day before walked by. The boy recognized them and smiled. He made eye contact which caused Josh’s cheeks to flush crimson. Josh was supposed to be a teenage boy too, but that time felt so far away now. Kathy giggled mischievously as Josh squirmed uncomfortably in his romper.
“Knees, dear,” his mother said firmly with a glance of annoyance. Josh’s heart jumped as he saw he had momentarily lost his concentration, and his knees were hanging sloppily apart. He clasped them quickly back together. In his consternation, he realized that he needed to use the restroom again. His spirits sank as he remembered he would need help with his romper again.
Cringing, he replied “Yes Mommy, It’s just that I, uhh I think I need to tinkle again,“ he said reluctantly. “I think I’ll need help with my romper again please,” he added.
“Goodness Joshy you just went!” his mother smiled in surprise. Inwardly, she was delighted to hear him use the juvenile word “tinkle” instead of something cruder.
Before he could respond, Kathy piped up and said, “I can help you Josh. I need to go too.” His sister grabbed his hand and led him to the ladies room as Gwendolyn watched. Kathy was behaving more and more like the older sister, and Josh was falling neatly into the role of the younger sibling.
“No half measures,” Gwendolyn repeated to herself determinedly. Any lingering traces of boyish misbehavior and recalcitrance were becoming increasingly hard to detect underneath all those curls and frills. She allowed herself to enjoy the moment and sipped her club soda with satisfaction. Unbeknownst to her children, she had another wonderful treat in store for the afternoon. She knew Kathy would enjoy it. As for Josh, she was now certain he would go along with little meaningful complaint or pouting. It was just one more step down his new path. Regardless of his reactions, however, the arrangements were already in place.
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Much as Gwendolyn herself has noted, Josh has really become the younger sibling, even if he would probably deny it. Boys especially seem to get so hung up on age as the sole indicator of maturity, after all.
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Thank you Andlat! I am a big admirer of all your well written stories also.
There is something deliciously inevitable in these stories about seeing a misbehaving young lad put in his place based on his actual maturity vs. his calendar age. The old cliche seems to be true: girls mature faster.
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PART 39
In the ladies room, Kathy unbuttoned her brother’s romper so he could sit down and relieve himself. Alone in the stall, Josh carefully pulled his romper and panties down around his ankles so he could tinkle. He had to learn to unbutton his romper by himself, he admitted reluctantly. It was humiliating to have to ask for help every time he needed to use the restroom. Girls’ clothes seemed so much more elaborate.
“Remember to wipe with a tissue when you’re done,” Kathy whispered to him from the next stall. Knowing that he was without a panty liner, the sissified boy complied to try and keep his panties clean. In that moment as he delicately blotted the dampness with a piece of tissue and pulled his lavender panties back up, it all seemed to crash down on him how much of a sissy he was now. He traced his finger lightly along the white lace of his panties and felt utterly girlish and weak. With a defeated sigh, he tugged his romper back up and slid his arms back into its puffy elasticated sleeves.
Soon, Kathy was buttoning him snugly back into his floral romper. As she buttoned the top one, Josh felt helplessly encased in all the girlishness of his new situation. He felt a tear well up when Kathy complimented him again on his flouncy curls, but he held it back as she helped him straighten his blue hairbow. Josh could not help but be shocked anew at the prissy girl staring back at him from the bathroom mirror with the golden curls and the big blue hairbow. The short bubble sleeves of his romper only highlighted his slender girlish arms. Dejectedly, he knew he was an absolute picture of sweet girlishness. Sensing perhaps that her brother’s emotions were swirling, Kathy squeezed him in a tender side hug in a moment of sisterly bonding as they both looked in the mirror.
“I adore you this way, Josh,” she whispered. “You look so sweet!”
Returning to the table, they sat down. Reflexively, Josh immediately pressed his knees together, sat up straight and folded his hands on his lap as he had been taught. This obviously pleased his mother and she nodded at him approvingly. Gwendolyn seemed to sense that her son’s conflicting emotions were especially active now. It was written all over his pretty face.
“How do you feel Josh?” she asked gently. “Are you getting used to all your pretty things? I have to admit I enjoy seeing this sweet and more delicate side of you, and seeing you and Kathy close this way reminds me of when you were both younger. Also, your new curls are truly adorable. and the point of all this is to make you feel lovely inside and out,” she continued. She chose her words carefully as she appraised her newly sissified son. “I’m proud of you for making this choice.”
Josh gulped and then replied with more honesty than perhaps he’d intended. “Mommy it’s just all so different and unexpected, I feel a lot of different ways,” he said tentatively. Being reminded again that this was the path he had chosen, he subconsciously touched his curls in a very feminine gesture. “I do feel pretty,” he added in almost a whisper.
Kathy chimed in kindly, “You ARE pretty Joshy, and I love having my sweet and kind brother back.”
They were all quiet for a few moments as if trying to process everything that was happening. Josh’s heart fluttered and his thoughts raced yet again. Was there a part of him that wanted this?
Finally, Kathy broke the silence and changed the subject as something different caught her eye. “Mom, I just noticed your nails. Did you get a manicure?” she asked. “They look great!” she added.
“Why yes dear, thank you,” Gwendolyn replied. “I didn’t really need another hair appointment since I had one just before we left home, so I just asked the stylist to clean it up a tad. Then, I had one of the nail technicians do my nails while I was waiting on the two of you. You were back there quite a while… especially Josh. She did a marvelous job.”
Josh noticed belatedly how his mother’s nails were flashing in the sunshine, and they were now painted a rich plum color.
As the check came, Gwendolyn continued. “As a matter of fact, it’s funny that you mention it, because I have a surprise for the two of you,” she said with a grin. “As I was chatting with Andrea this morning, she said the nail techs were having a really slow week as well, and she offered to throw in mani-pedis for all of us at half price if I wanted. You’re both old enough, so of course I agreed at once. You both have appointments as soon as we are done with our lunch! We’re going to make it a full day of beauty!”
“That’s so awesome!” Kathy said at once. “Thanks Mom!”
Gwendolyn looked at Josh expectantly. “Won’t that be fun dear? This is turning into a real girls day out!” she said leadingly. “Rip the Band-Aid off,” she thought for the hundredth time.
Josh was having a very different reaction than his sister. He had already been slowly and painfully coming to grips with his new girlish hairstyle. He was unsettled now to learn he would be going right back to Miss Andrea’s salon for his first manicure and pedicure. He wished he could disappear into his seat. He could not help staring at his plain fingernails and nervously wondering how sissyish they would soon be. And, just like his hairdo, this was something that would not be easily undone without some effort.
“Th.. Th… thank you Mommy,” he said glumly as his little man tingled unexpectedly, adding to his feeling of unease. It just made everything worse.
“Truthfully, I was sort of hoping to do this for you today. That’s why I didn’t want you to wear your pretty tights this morning,” Gwendolyn continued. Gesturing to Josh’s petite feet in his cute little flowered sandals she said, “It will make you feel so much prettier to clean up those raggedy nails, and some nice polish will complement your sandals wonderfully I think.”
Gwendolyn saw that her latest subterfuge seemed to have passed with little notice. Until today, she had presented every new feminine step to her son as a choice, at least superficially. Ostensibly, he could have chosen not to wear the dress, tights, etc. But first with his hair appointment that morning and now with the mani/pedi, she had merely informed him of the arrangements that were already in place for him. Of course, he could still always try to complain or refuse, but she was betting on his compliance at this point. She didn’t even ask whether he wanted his nails done; she just told him about his appointment. She noted that he didn’t think to push back on her. She was elated at his progress!
Josh stared down at his toes peeking out from the delicate white sandals and felt his face redden again. His perky new curls bounced airily as they caught the gentle spring breeze. His thoughts were consumed by a mental picture of himself sitting powerlessly in the salon while his nails were painted. It was an excruciatingly prissy and girlish image. His heart fluttered as he knew that vision would soon become his reality.
In that moment, Josh could only take stock of his increasingly precarious situation: A looming nail appointment complete with nail polish. A lovely new perm with precious curls and golden highlights. Panties and panty liners and training bras. Dresses and tights and hair accessories. This was all happening so fast. The romper-clad teenage sissy trembled slightly as he contemplated the next impending step of his feminization with chagrin. He felt so far removed from anything remotely boyish.
“Time to go,” Gwendolyn announced as she paid the check.
Kathy excitedly took Josh’s hand again and pulled her sissified brother toward the sidewalk. Trapped once again, the feminized teen followed his sister meekly with mincing steps as they made their way back across the street. His first nail appointment beckoned.
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sissyboy1212,
I really enjoyed those last chapters.
I'm imagining myself as Josh, dressed as a girl on public display in a romper that I can't get in or out of by myself without assistance to use the LADIES room, with my hair in permanent curls and now going back to the salon for a manicure/pedicure.
The closest I came to that in real life was 9 Halloweens ago when I attended two different parties as a bride when I had to cinch up tight to squeeze in and have an attendant zip me in and out of my wedding gown. I gave it away several years after, but think I got my monies worth out of my $25 thrift store purchase.
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Wonderful! Thank you for your sweet writing.
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Thank you Dolly and Katie!!!
So much appreciate your kind comments. Real life has kept me from doing any writing here for a while, but I have some more plans for Josh.
Especially would love to hear about your bridal Halloween costume dolly bo peep :)
Glad you are enjoying :)
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My goodness, Josh just can't catch a break! Of course, I don't think we'd want it any other way.
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This is a well written story with a fresh creative story line. I ask the author to please continue the story.
Josh’s mom has planned this lifestyle change for Josh and she does not plan on it ending very soon. Josh is thinking that he could play along for the two weeks until the vacation ends. Then things can get back to normal.
Josh’s mom has done her planning well. She knew her pansy son would never choose the rigid structured program of Stonecourt and the discipline that went with it.
When investigating Stonecourt, Josh’s mom may have realized after reading the Stonecourt’s brochure what made Stonecourt's program so effective in molding a boy into becoming a man. Stonecourt's program could be used as a model to make necessary changes to Josh.
Why yes, a sissy program for Josh could be modeled after Stonecourt's program?
After all:
The simple curtsy is much like a hand salute in the military.
Mom sets the uniform Josh wears. In this case dresses.
Inspections can be used to insure josh dresses herself properly and keeps her room clean and tidy.
Yes, we need a supervised schedule. Exercises for Girls. Deportment lessons.
If Stonecourt is to be the model, discipline along with peer pressure needs to be used. For little set backs or poor performance, deportment exercises could be used for discipline. Demerits could be given out of course for disobedience or major problems. We too can have a paddle time of sorts. Perhaps a panties down public paddling scheduled for Saturday afternoon would be used for acts of disobedience. Video in peers such as his aunt, school principle, teachers, neighbors and the threat of friends. Maybe a trip to Stonecourt to see how they do paddle time there.
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bobbie99,
Thank you so much for your thoughtful comments and feedback. I do intend to continue this story at some point, but I've just not had time to come back to it lately. I've not really been on the board for the last few months.
You are definitely on the right track with my thoughts in writing this story. I have enjoyed playing with the idea that our young hero gets ever more progressively boxed into deeper and deeper levels of sissyhood by his increasingly overbearing mother. It's not physical force like some of the other stories posted here. The convincing/prodding/manipulating mother with a clear goal in mind is a concept that appeals more to me. I enjoy the idea of all poor Joshy's possible "escape routes" being closed off on by one...
Thank you again for your lovely words. Hugs!
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PART 40
Once again Kathy led her brother into Miss Andrea’s salon. In no time at all, Josh and Kathy were paired up with Denise and Rachel, the nail techs who would do their mani/pedis. Instead of returning to the hair styling stations, Josh soon found himself sitting in a big elevated salon chair near the front windows. Kathy was in an identical chair a few feet away while his mother sat in the waiting area where she could see everything. Both nail technicians were attractive young ladies in their twenties, and soon Josh had his hands and feet soaking in small tubs as the ladies prepared their tools.
Denise spoke first, “I’m Denise, Josh, and I’m going to take good care of you today. Andrea has told me ALL about you.” She continued with a warm grin, “By the way, I love your hair! Those curls are just too adorable!” Next she asked, “Is this your first nail appointment sweetheart?”
Josh felt his cheeks warming as he replied. “Uhh yes it’s my first time, uhh with my nails and everything,” he managed to stammer. He had barely had time to get used to his new girly curls, and the next step of his sissification was already underway. He cringed as Denise pointed out his “adorable” curls.
“Well you can start thinking about the color polish you’ll want, honey, because we have lots of choices,” she said eagerly,” and I know you’ll want your first time to be extra special!”
Josh looked helplessly over at Kathy, and he saw she was listening to this exchange with a grin. She mouthed something to him and nodded her head excitedly.
“Uhh I guess I’d like pink,” he said without much enthusiasm. “Uhhh pink please Miss Denise,” he added quickly as he caught his mother’s eye. He knew he was expected to be sweet and polite. Gwendolyn smiled approvingly at her feminized teen as she watched his next step into girlishness begin.
“Of course he’ll want pink,” Kathy chimed in, “It will match his lip gloss.”
Denise continued with a smile, “Oh but Josh we have more than 20 shades of pink to choose from, so you’ll have to be more specific,” Denise explained. She stepped to a large bookshelf holding what looked like at least a couple hundred bottles of nail polish and selected a tray full of pinks. “You see we have Baby Pink, Coral, Fuchsia, Cotton Candy, Sunrise, Rose Pink, Bubblegum Pink, Spring Plum and several more to choose from! I’ll just set these here so you can think about it while we start working,” she said with a twinkle. She placed the tray of glistening pink nail polish bottles on a small stand right in front of him.
Kathy giggled a bit and said, “Decisions, decisions… they’re all so pretty!”
Chagrined, Josh felt his little man stir. His self-consciousness only increased as the ultra-feminine nail polishes seemed to beckon to him. It drove home the inescapable fact that he would soon have a complete set of prettily painted fingernails and toenails. It only heightened his sense of embarrassed anticipation and he squirmed uncomfortably.
He sat wordlessly as Denise took his hands from their soak and carefully dried them. He had to admit it felt nice to be pampered as she trimmed his cuticles and then carefully clipped and buffed his longish fingernails into graceful, feminine ovals… first his right, then his left. She used a block to buff the nails to a high shine even without any polish.
“Now for your basecoat,” she explained to the increasingly nervous teen. His heart fluttered a bit as she applied the first strokes of clear basecoat polish to his right hand. The polish felt strangely cool on his nails, and he immediately smelled the distinctive odor of the nail lacquer. “This basecoat will strengthen and reinforce your nails to prevent any chipping or splitting,” Denise added helpfully.
The boy was surprised when she pulled out a small gadget which she guided over his right hand. When she switched it on, it emitted a bluish light. She noticed his confusion and said, “Oh Josh this is an LED nail dryer lamp. We use it to cure each coat for about a minute.”
“Ohh…?” he replied, still not quite understanding.
“Josh,” Kathy piped in, “we’re getting gel nails. “They are SO much better than regular polish!” she said cheerfully.
“That’s right Josh,” Denise added. “Some people call it ‘permanent’ nail polish,” she went on. It’s not truly permanent, but it bonds with your nail and will last several weeks or even a month without peeling or chipping! So make sure you pick a color you like because you will have it quite a while!”
The other nail tech, Rachel, spoke next, “But it’s really tricky to remove without ripping up your nails. You can’t take it off with nail polish remover alone. Best to return to a nail salon for that otherwise you could even rip a nail off and hurt yourself. That’s why people call it permanent!”
“Permanent nail polish!” Josh thought in horror. “Weeks with pink painted nails?” His stomach seemed to drop as she repeated the process on his left hand. He couldn’t get the word “permanent” out of his mind as Denise continued to work. Just like his new permanent curly hairstyle, now his nails would be permanent too.
His mother spoke up again, “Oh we won’t need to have it off anytime soon, so they can both enjoy their lovely mani/pedis until they need a maintenance appointment.” Gwendolyn added breezily. “Won’t that be lovely, Joshy?”
As the full gravity of this process sank in, Josh could only reply weakly, “Oh yes Mommy that will be wonderful.” The stress of the moment brought his little man to life. He reddened with embarrassment as this essential part of him seemed to somehow crave his sissification in spite of himself. In short order, Denise repeated the process of drying, clipping, and filing his toenails as well. She slipped pink foam toe spreaders on each of his feet, and soon all his toenails and fingernails glistened with a shiny basecoat as well. He felt so sissyish and trapped at this point. When Denise picked up the tray of pink nail polishes, Josh knew what would come next.
“Decision time sweetheart!” Denise announced. Kathy looked on and his mother stood and stepped closer to get a closer look. “What color should we go with?” Denise cheerfully asked.
Josh froze. He didn’t want to pick any of them. He was beet-red at this point. Kathy finally rescued him, “What about the last one on the right at the top Josh?” she suggested helpfully.
It seemed to break the spell, and the blushing boy said, “Sure can I see that one?”
Denise replied, “Oh that’s one of our most popular colors with the young girls. It’s called Baby Pink Sparkle. It’s such a delicate and sweet pink color with a touch of iridescence that makes it shimmer nicely and catch the eye. Very pretty.”
After a long moment’s hesitation, Josh said simply “Okay.”
Gwendolyn, however, was not satisfied. She cleared her throat purposefully. “Josh, honey you know we’ve talked about this. You should be more clear so Miss Denise knows exactly what you want.” The slight tone of reproach was back in her voice.
Josh knew the type of answer that was expected. After all, this was all his choice. Taking a deep breath, he said, “Yes Miss Denise, I would please like the Baby Pink Sparkle polish. It’s so pretty!” Once again, he was amazed and dismayed at how easily the flowery words seemed to jump from his mouth.
Denise beamed brightly and said “Of course sweetie. Great choice!”
Everything after that was a blur as the subdued boy got two coats of lustrous Baby Pink Sparkle nail polish on each nail plus a shiny protective clear topcoat. Each coat of polish was cured and bonded with the LED light machine which reinforced the permanence of the process to him. He barely registered that Kathy chose the same color so they would match “just like sisters.”
As they finally departed the nail salon after a full day of beauty, poor Josh’s emotions were again on edge. He was sinking ever deeper with no apparent way back. He was only momentarily distracted from his shiny pink nails when the gentle breeze caused one of his new bouncy curls to dance across his forehead. The boy in the cute romper dress and adorable curly hair was lost in thought. Every time he glanced down, he saw how his dainty white sandals complemented his pretty nail polish. His “permanent” nail polish. He sighed again.
Gwendolyn smiled. In her mind, the theme of the day had been “Permanence.” She was very pleased with the results. “No half measures,” she thought to herself.
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Overwhelmed as he is by all these novel experiences, it's little wonder Josh did not pick up on the reference to a "maintenance appointment" in the future. How lucky he is to be so fully immersed with no shortcuts taken in his journey into sissyhood.
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Many thanks Andlat. Your feedback means a lot coming from someone who writes such wonderful stories.
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PART 41
His mind racing, Josh found it impossible to avoid looking at his nails. He repeatedly held out his hands to study his glistening pink nail polish. He couldn’t quite fathom that those delicately feminine hands were his. Lost in his girlish thoughts, he was abruptly startled by a now-familiar voice.
“Well hello again!” Mrs. Smyth spoke to them. Flustered, Josh jerked his head up to see they had met her walking on the sidewalk. “Oh my,” she observed with a grin. “Don’t you all look lovely? I suspect you ladies had a busy day with Andrea.”
Gwendolyn replied cheerfully, “Oh yes, Dolores, we’ve had a lovely time with hair and nails today. Andrea and the girls in her shop treated us just like princesses!”
“And Josh even got a perm!” Kathy added helpfully.
Josh was mortified as Mrs. Smyth studied his new look. Again, she seemed to zero in on him in particular. His cheeks were warm as she said, “Well Josh you look sweet enough to eat!” she said jovially. “Your new curls are absolutely scrumptious my dear. So girlish and bouncy! And another pretty hairbow! A perm is certainly a commitment, but it looks precious on you. So youthful. And those look like gel nails. Denise and Rachel do nice work. What color is that?”
When he didn’t immediately respond, Gwendolyn piped in, “Well answer Mrs. Smyth honey. After all, you picked out your nail polish yourself!”
Josh cringed. He was beyond embarrassed that he knew exactly what color his nail polish was. He had asked for it by name, and now he had to discuss it again. “Uhh. Yes Mrs. Smyth thank you so much. Miss Denise did my nails. Uhh, my nail polish is called Baby Pink Sparkle. In a weak effort to shift the attention, he added, “It’s the same color as my sister Kathy’s.”
“Baby Pink Sparkle, fingers and toes!” Mrs. Smyth observed with a twinkle. She blew right past Josh’s pitiful attempt to distract her. “Well Josh you are becoming quite the little fashion plate I must say. You look adorably cute in that playful romper. The shorts are so full and billowy that at first I thought it was a true skirt. Of course, that outfit is less dressy than your delightful chiffon dress I saw at brunch or that lovely gingham one from the other day, but it’s very cute. I notice you’re wearing your strappy sandals again. The white tights you had on yesterday were lovely, but it would be a shame to hide those pretty pink toenails. The flower sandals pair nicely with your summery romper and show off your pedicure beautifully. I love the delicate white sandals with your baby blue romper. Very feminine. You’re surely the prettiest boy in town my dear! It’s a rare teenaged boy who can pull off such charming outfits. Aren’t you lucky to be so petite! Baby Pink Sparkle indeed!”
Josh knew she meant these as compliments but her words put an exclamation point on how much of a sissy he had become. He had already learned that Mrs. Smyth had a unique talent for noticing even the smallest details of style and fashion. It was excruciating to have every aspect of his girlish appearance examined and highlighted this way. She relished each feminine detail in a way that just magnified his embarrassment. The fact that he was not a real girl but a sissified boy truly seemed to intensify her interest in him. He squirmed uncomfortably to be back under her microscope. Nervously, he recalled her ominous words from their very first encounter: “I can’t wait to get my hands on you, my dear!” For the thousandth time, he was blushing again.
“Th-thank you so much Mrs. Smyth,” he bashfully replied, “that’s all so nice of you to say.”
Josh wondered if Kathy might be jealous of all the attention he was getting, but if anything she seemed even more excited about her brother’s transformation than Mrs. Smyth. As if on cue, she piped in, “They did a great job on his highlights too! I just love helping him get all girly and pretty. The last few days, I’ve felt like he’s the sister I never had!”
“Well as I said before, it’s obvious you have a good eye for fashion,” Mrs. Smyth said to Kathy. “I know young Josh appreciates all your help,” she added kindly. "He's all sugar and spice now!" she declared.
Gwendolyn watched appreciatively while her sissified son reddened and fidgeted. He was just so cute with his pink blushing cheeks and darling new curls. He looked delightfully sweet with his new baby blue hairbow. Today had been another day of wonderful progress! Then, she remembered that there was something else she had intended to check today. She still had it in her purse as a reminder. Perhaps Mrs. Smyth would have some additional information. She opened her purse and searched for a moment. Where was it? Then she found what she was looking for and pulled it out. Smiling, Gwendolyn turned back to Mrs. Smyth.
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Lucky Josh. You are bringing out my envy. Please continue.
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Ooh, a cliffhanger! I can't remember what it is she has, but I can bet it's not good news for Josh!
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sweet baby katie, I am glad you enjoy the continuing story. Rest assured you are not the only one who is envious!
Andlat, yes a cliffhanger. I would politely disagree with you on one small point, however. I personally think it's WONDERFUL news for Josh! He might disagree if we asked him, however! :)
Thank you both for your kind comments.
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PART 42
“You’re very kind Dolores,” Gwendolyn spoke again to Mrs. Smyth. “When you mentioned seeing us yesterday at brunch, I remembered this flyer I picked up as we left the restaurant. Are you familiar with this ‘High Tea Tuesday’ event tomorrow?” Gwendolyn asked. “I wonder if they’d still have any tickets.”
“Oh yes of course,” Mrs. Smyth replied immediately, “It’s a festive time and you can buy tickets at the door. There should be plenty of room for all of you.” She explained, “Two or three times a year, the nice lady who owns the restaurant hosts a ‘High Tea.’ Everyone dresses up in fancy dress and we have an English-style tea with finicky little finger foods. They usually even have scones. Some people go all out with period costumes and everything. It’s a fundraiser for the Ladies Auxiliary. It’s mostly us girls in attendance of course but a few gentlemen show up now and then. You should all get dressed up and come!” she encouraged. As she said the last part about getting dressed up, Josh noticed that Mrs. Smyth deliberately turned her gaze back onto him. She was obviously already picturing him in her very particular idea of “fancy dress.” He shuddered slightly as he recalled the frilly, feminine outfits displayed prominently in her store windows.
“It sounds lovely, but I’m afraid we don’t have any clothes quite that dressy with us,” Gwendolyn said with a trace of disappointment. Hearing this, Kathy looked disappointed too. Josh had been listening to this conversation with growing dismay when it was obvious where it was headed. Consequently, he exhaled in thankful relief when he realized that he wouldn’t be subjected to that overstuffed tea party at least. Moments later, however, he knew he had celebrated too soon.
“Nonsense!” Mrs. Smyth said. “Did you forget who you’re talking to, Gwendolyn? You’ve already promised to visit my shop and this gives you a great reason! I happen to keep some extra vintage outfits in the storeroom at the shop and I’d be thrilled to find you some loaners. Over the years, some of the ladies have donated things they’ve used in the past so others can enjoy them, and I’ve wound up storing them since I have the space. Whenever we do the teas, many of the locals stop by to borrow items for free instead of buying costumes and things they will rarely wear. All I ask is that they cover the dry cleaning costs. I even have several outfits that Mrs. Meriweather gave me when her daughters outgrew them!” she added excitedly. “There are still plenty of nice things to choose from and I just know we can find something to suit you all.”
“You are too kind, Dolores. That’s very generous of you,” Gwendolyn said happily. She was delighted as she imagined her children in wonderfully fancy outfits for tea. Of course, the prospect of putting Josh in another gorgeously feminine outfit appealed to her immediately.
Mrs. Smyth spoke again, “Mrs. Meriweather might also have some things stored at her house that could work, especially items that might fit you Gwendolyn. You’re about her size. You should ask her. I know she’d be thrilled for someone to get some use out of those outfits,” Mrs. Smyth went on. “The tea is at three tomorrow afternoon. Why don’t you come to the shop around noon tomorrow and we will get you all sorted out for tea?”
“Of course we will. Thank you Dolores!” Gwendolyn said with anticipation. “I guess we’re going to high tea!” she said to her children happily.
“I can’t wait to get all dressed up in a fancy dress!” Kathy said eagerly. “Won’t that be fun Josh?” she asked her crestfallen brother.
All three of them—Gwendolyn, Kathy and Mrs. Smyth—turned expectantly to the sissified teenager. Once more the focus of overwhelming feminine attention, Josh was in disbelief. He felt the rug had rudely yanked from under his dainty, sandal-clad feet. “High tea and fancy dress?” he thought in horror. He tried to imagine what a girlish outfit he would have to wear tomorrow. His tummy fluttered and he felt lightheaded. Again, he remembered with dismay that all of this had been his choice. With a forced smile, he finally replied, “Th-that will be wonderful. I can’t wait… to get dressed up in pretty clothes for tea.”
“I must confess I am positively eager to put you in some lovely outfits!” Mrs. Smyth said gaily. “I’ve got a splendid dress in mind for you Kathy.” Then, fixing her attention fully on the feminized fifteen year old boy, she continued gleefully, “And of course Josh I have a few extra special ideas for such an extra special boy. Oh you’re in for such a treat!”
Gwendolyn, feeling slightly giddy, replied, “Feel free to go all out Dolores! It feels like a special occasion!” Then, unintentionally, she blurted the quiet part out loud, “No half measures!” Realizing what she had said, she held her breath and glanced anxiously at Mrs. Smyth.
Mrs. Smyth returned Gwendolyn’s look quizzically, but she did not reply. Instead, the two ladies silently locked eyes, and something unspoken passed between them. In that moment, Mrs. Smyth seemed to gain a deeper understanding of this unusual situation. Mrs. Smyth’s eyebrow arched slightly, and then Gwendolyn’s eyes softened a bit as she relaxed. Next, Mrs. Smyth nodded almost imperceptibly and her cheerful manner returned instantly. “See you tomorrow!” she called jauntily as she departed. “Hmm… no half measures,” she thought to herself.
Oblivious to this subtle exchange, Josh unconsciously brushed the delicately curly fringes from his forehead as he watched Mrs. Smyth march away purposefully. Undeterred, his springy new curls bounced back immediately to dangle adorably in place. He glimpsed his pink sparkly fingernails again as they flashed in the sun… his “Baby Pink Sparkle” fingernails. He realized his hand was trembling. He shivered slightly as his little man jumped, and he was suddenly acutely aware of his bra straps and lace-trimmed panties again. He grimaced slightly as he looked down only to see the baby blue floral romper hugging his slender body.
Permanent girly curls. Permanent nail polish. Hairbows, dresses, bras and panties. And soon, he would be delivered to Mrs. Smyth in her dress shop like a prettily wrapped present. He fretted powerlessly as he thought about her “extra special ideas” for him. His spirits sank even as his little man tingled more excitedly. Helplessly confused by his conflicting feelings, Josh sank inexorably deeper into his exquisitely sissy new world.
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Goodness! Well, now I'm going to spend all day imagining just what outfit Josh has in store for him. A dress seems obvious, but with Josh being a thoroughly sissified boy, who knows what the extra special ideas could be!
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sissyboy1212, I am so glad you are continuing this story. There are so many stories here that dive deep into the world of humiliation, and while I love a good story where a sissy gets humiliated (and this one definitely has it's moments of embarrassment for Josh), there's an undeniable undercurrent of love and warmth to this one that makes it simply intoxicating to read. Gwendolyn clearly loves Josh and wants to make him the best little girly-boy he can possibly be. The idea that she loves feminizing him and it's beyond simply being a punishment at this point makes it all the more sweet. I can't tell you how envious I am that Josh has such a figure in his life to help guide his journey into sissyhood. I'm also very excited to see what kind of outfits Mrs. Smyth puts him in. You've definitley got a great thing going here. Keep it up!
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Thank you Andlat and CuddleBunns for your sweet comments.
CuddleBunns, you have hit precisely on the subset of these stories that truly appeals to me. Of course I love terribly embarrassing sissy situations, but I still want a heavy dose of sweetness mixed in. "Brute force" situations with nothing but extreme humiliation are just less interesting to me. To each their own. Thank you for hitting the nail on the head and I appreciate your kind feedback.
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Fair warning. This may be the last installment of this story for a while. I know where I want Josh to end up, but I'm stumbling a bit figuring out how to get him there. Thanks for the encouragement and hope you enjoy this one.
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PART 43
Josh was still in a daze when they returned to the Meriweather house after their busy day of beauty. Literally and figuratively, things seemed much more permanent now. Dinner flew by and before he knew it, he was back in his pretty pajamas with a fresh panty liner. When he had pulled the panty liner from the box with his pink polished fingers, he was struck again by how incredibly girly he was now. His white leggings with the little hearts and his stretchy pink pajama top seemed even clingier than before. Their tulle fringes tickled him ceaselessly. His mother insisted again on tucking her sissified teen into his frilly pink canopy bed. As she kissed him goodnight, she said, “Remember to keep your scarf on tonight to protect your pretty new curls sweetheart. Don’t you just love them?”
Josh cringed again to be reminded of the latest addition to his bedtime routine. Now, his curly new perm was covered and tied up in a large pink silk scarf. His mother had explained that this would keep his curls from getting too tangled and frizzy overnight as he slept. Of course, it was just another ultra-girly thing he was having to get used to.
“Oh yes Mommy,” he replied with a slight wince. “I just love how bouncy and curly my new perm is.”
“Good night princess,” she said merrily as she turned out the light. “Tomorrow will be a busy and exciting day,” she added as she closed the door. She savored using the word "princess" with Josh as if it were a delightful piece of chocolate.
Although he dreaded tomorrow’s trip to Mrs. Smyth’s dress shop, Josh was exhausted from the events of the day. Despite his racing thoughts, Josh quickly drifted off and was soon immersed in vivid dreams of another elaborately girly transformation.
He dreamed that his entire body was wrapped tightly in wide satiny pink ribbons which completely secured him to a high-backed salon chair. His arms were wrapped tightly to the arms of the chair with more of the same oversized ribbons. He found his hands had been squeezed into sturdy white fingerless gloves made of thick hard rubber. These gloves were in turn fastened down to plate-like fixtures attached to the ends of the chair arms. This arrangement held the palms of his hands tightly down flat against the plates. All his fingers were splayed out and individually wrapped and tied down snugly with more pink ribbons.
He could see the chair was raised up on a pedestal and little spotlights focused on him from above. Although he couldn’t see anyone else, he could hear the excited chatter and giggles of people watching him just beyond the light. Most of the talking was indecipherable but occasionally he heard snippets of conversation peppered with words like “precious,” “permanent,” “prissy-sissy,” and even “far too pretty to be a boy.” He could feel the heat from his blushing cheeks now. A dream version of Miss Andrea worked silently and happily to wind his long hair tightly in endless streams of pink curlers over and over again as he struggled helplessly in his pink ribbons. He watched in horror as a dream version of Miss Denise began to delicately paint bright pink polish onto the nails of his completely immobilized hands.
As Miss Denise applied coat after coat after coat of the lovely nail polish in long even strokes, someone called out, “What color is your nail polish sissy?”
He didn’t want to answer, but the words came out automatically in a sing-song voice. He heard himself say excitedly, “Baby Pink Sparkle! It’s Baby Pink Sparkle! I just love my Baby Pink Sparkle!” The invisible audience broke out in sweetly condescending “Ooohs,” “Ahhs,” and also more than a few snickers. He was horrified that this all served to awaken his little man.
Josh squirmed frantically to free himself, but the ribbons just tightened the more he struggled. A rapidly growing mass of pink curlers was progressively pinned ever more securely in his hair while his fingernails were repeatedly painted with countless coats of polish. Suddenly, Miss Rachel from the salon appeared and firmly lifted up his fine-featured chin. Smiling appreciatively at his helpless state, she produced a tube of shiny pink lip gloss and began applying it to the boy’s quivering lips. Josh smelled and tasted sweet strawberries as Miss Rachel worked methodically to coat his lips with a thick layer of it. As she worked, every few seconds she would squeeze his cheeks and force his lips into a darling pucker. The combined smells of the nail polish, perm chemicals and strawberry lip gloss overwhelmed his senses and made him lightheaded. He felt his pulse racing. His little man was tingling now.
Just then the salon chair began moving forward as if on a conveyor belt and the ladies suddenly vanished. He was alone now except for the invisible audience and still inescapably bound to the chair. His hair was imprisoned in a mass of pink curlers. His nails glistened with shiny nail polish, and his lips were thoroughly coated in pink lip gloss. Right on cue a dim pathway lit up before him as the chair moved. He was immediately fearful of what lay down the path. Josh struggled even harder now but the ribbons held him fast. His heart beat rapidly and he took short quick breaths. He saw someone standing in shadows at the end of the path, and the chair moved him steadily closer to the mystery figure. As he neared it, the light brightened and the crowd murmured loudly. Finally the light came up fully, and he saw Mrs. Smyth smiling eagerly at him. His stomach leapt as the crowd noise turned to buzzing in his ears. His chair stopped directly in front of her. “My, My!” she said excitedly as she looked him over carefully, “what an extra special little boy!”
Josh was beet-red now. The combination of intense embarrassment and nervous anticipation overwhelmed the sissified teen. He gasped involuntarily and let out a soft girlish moan. Unable to hold out any longer, his little man shook once vigorously and then finally let go.
Josh abruptly woke up. His eyes flew open and the first thing he saw was the wispy pink canopy above his bed with all its dangling ribbons. He groaned as he grasped what had happened. Again. He had made another sticky mess in his panties. Another humiliating “little squirtie.” He realized he was still wearing the silk scarf over his curly perm. That part of it wasn’t a dream. One glance at his nails told him that part was real too. Looking to the window, he saw the sun was already up. It was morning. He remembered it was also “High Tea Tuesday.” The teenaged boy’s reality had swiftly become this sissy nightmare.
“Joshy are you awake in there?” he heard his mother call to him. After a pause, he heard her again, “Rise and shine angel, it’s time to get up!”
He groaned again.
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I must say, you have quite the talent for portraying Josh's inner struggle. While it was front and center in this dream sequence and the morning aftermath, it brought further attention to how very much you've done to keep his conflicted feelings present throughout the whole story so far. There are certainly fun stories where the main character is little more than a shell for the reader to occupy, but Josh feels like an actual teen whose shoulder we're looking over as he goes through all these changes.
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Thank you Andlat. That means more than you know. In some ways, that teenage boy is me. That's why I know his feelings so well.
I think Josh is lucky even if he doesn't know it yet.
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sissyboy1212,
I have just been catching up and really enjoying your story.
I did notice a little inconsistency in the name of the military school - in the beginning of your story it was Sterncourt, and the last time it was mentioned, the name changed to Stonecourt. I prefer the initial name of Sterncourt.
I will have to be patient for your next chapters. I am imagining myself in Joshy's place. My mother would not be pleased about my night time "squirtie" so I would be wearing a diaper and plastic pants under my outfit. After all, it is borrowed and we can't be getting stains on it. Furthermore, a rest room visit in the outfit would be almost impossible anyway. The outfit would be complete and authentic all the way, including a corset tightened by my sister, frilly pettipants covering my diaper, and voluminous petticoats. My dress would be a short one for a little girl, so one sudden move or wayward breeze and my frillies would be on display! After I am in the outfit, it will be time to put on my bonnet and attend the high tea.
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Thank you Dolly. That's very sweet and I'm happy you are enjoying Josh's adventures. You describe a lovely little mental picture :) I've already got Josh's perfect outfit planned. It was one of the first things I decided on when I started this story. I just didn't know it would take me so long to get him to tea!
As for the name of the school, I'm fairly certain that you'll see I've always called it Sterncourt. Some of the other posters have accidentally called it by the other name on occasion, but their comments were very nice and I didn't point it out. The school is definitely Sterncourt though.
Thanks again.
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PART 44
Josh leapt out of bed just as his mother opened the bedroom door.
“We have an exciting day ahead, honey, and remember we need to be at Mrs. Smyth’s by noon!” she reminded him as she stepped into the room. Then, almost as if she already knew the answer, she asked, “No accidents again last night I hope?”
Crimson now, Josh tried to cover himself with his hands. Moments earlier, as soon as he had pushed back his bedcovers, he had seen the obvious wet spot on his thin white pajama leggings. He was less lucky than he had been in the salon yesterday. His panty liner had been unable to contain everything this time.
“Uhhh…” the red-faced boy stammered. “I… uhhh…” he began again.
Comprehending now, Gwendolyn asked gently, “Did you have another little accident, sweetheart?”
“Yes Mommy,” the humiliated teen replied reluctantly. Realizing there was no hiding it now, he stared at the floor and said, “I had… a little squirtie.”
“I see,” Gwendolyn said sympathetically, “Well just drop your jammies in the hamper again and go take a nice shower, dear.”
Grateful to escape the embarrassing situation, Josh immediately scampered into the bathroom to clean himself up. As she watched him dart off, Gwendolyn was thankful to now have a solution for this little problem. She had noticed another package on the porch yesterday when they returned, and she had opened it up after the children went to bed. “And not a minute too soon,” she thought. She had planned to have this on hand when Josh made his initial choice, but better late than never. “You really can find anything on the internet,” she chuckled to herself.
In the bathroom, Josh quickly stripped off his damp pajamas and panties, and he daintily deposited his soiled panty liner in the little garbage can. He removed his silk headscarf, and he jumped in the shower rapidly, trying to put the latest embarrassment out of his mind. He remembered his mother had told him to keep his hair dry to protect his new perm, and he mostly succeeded.
He finished his shower and began to dry himself off when he heard his mother calling again from his bedroom. “Joshy, if you’re out of the shower come here for a moment. I’ve got something for you.” Taken a little off guard, he realized that he had no clothes in the bathroom with him. Wrapping a fluffy pink towel around his waist, he stepped back into the room to see what his mother wanted.
“Josh,” she began delicately. “I have something here that I think will help you with your… accidents.” She held up a clear resealable plastic bag that had something pink in it. “This is a… a helpful little device that should help keep you dry.”
He had no idea what he was looking at or how this could possibly help him. Confused, he looked at his mother and said, “I don’t understand.”
Taking the pink plastic device from its package, she explained, “Well you see honey, this little gadget goes right over your private parts. I know it sounds strange, but it’s just a little “helper” to avoid… any more embarrassing situations,” she went on carefully. “Here,” she said as she handed him the device, “the instructions are right there in the bag with some helpful diagrams.”
Vaguely understanding but still not yet fully comprehending, Josh asked hesitantly, “Over my… my privates?”
A little more confidently, his mother continued, “Yes dear. Wouldn’t it be nice not having to worry about more accidents? It’s just something that might help you stay clean and tidy.”
Josh could scarcely believe his ears. “Mom… Mommy, I don’t know…” he started to reply. But then, his voice trailed off. He remembered the whole episode of his “little squirtie” in the hair salon when he was getting his perm. It was bad enough that it had happened in the first place, but at least no one knew about it. He had managed to keep that secret. There was a part of him that was now actually curious about this thing and how it might work.
“Oh Joshy, this is truly your decision if you want to try it,” she explained. She had already decided that this would have to be his choice. It’s the only way it would really stick. She would highlight her preferred option, of course, but it would ultimately be up to him to decide.
After a long pause, the dumbfounded boy could almost not believe what he heard himself say next. “I suppose… it wouldn’t hurt to try it on,” he said.
“OK sweetie,” she said brightly “I’ll help if you need me to, of course, but I thought you’d prefer to manage it yourself if you can. Why don’t I wait here while you go try it on?”
Shivering slightly, Josh took the strange plastic device into the bathroom.
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So nice to get an opportunity to check in with Josh again! Hopefully this helpful little device will make his transition into sissyhood all the easier.
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sissyboy1212,
Thank you for the latest chapter.
That pink device should fix those pesky little squirties, and Josh is trying it on himself, so it is at least technically his decision.
Will Gwendolyn have to help get it fitted properly, or will Josh figure it out himself and then all she will have to do is lock it and take the key (or keys, with one being held by Kathy)?
With those squirties replaced by smaller dribbles, will Josh need slightly larger capacity panty liners, or will the current ones do?
Once Josh, Kathy, and Gwendolyn are in their vintage dresses and attending the high tea, will Josh have to be assisted by Kathy during any rest room visits?
I'm eager to read what happens next.
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PART 45
Closing the door, Josh still didn’t fully grasp why he had agreed… And what exactly was it he had just agreed to? His rapid descent into sissyhood seemed surreal at this point. Just like his dream, there seemed to be no escaping it. As with everything else, he was keenly aware his own choices had led him here.
His mother’s voice again jolted him from his thoughts. “Oh honey, there’s some organic rosehip oil on the counter if you… err… need something to help get everything into its proper place,” she called helpfully.
Standing before the counter, Josh dropped his towel. His heart fluttered as he examined the diagrams more carefully. He didn’t bother reading all the writing since the diagrams were very clear and straightforward. He saw there were actually two pieces of hard pink plastic. One piece was ring-shaped, and the other was obviously meant to go around and over his little man. Now the realization of what he was about to do firmly took hold and his nerves increased. He also saw how the whole thing was supposed to be held in place by a little padlock. He saw there was a tiny open brass lock in the bag too.
“Mommy, uhh there’s a lock here but no key,” he called out with concern. “Does this thing actually lock on?” He was now having serious second thoughts about this whole thing.
“Don’t worry honey… there are two keys. I took them out to make sure they don’t get lost!” she called back. Gwendolyn did her best to hide the anticipation in her voice, “Just use the lock for now and we’ll figure out something else later if we have to.”
His hand shaking a bit, Josh pulled his privates through the ring just like in the diagram. He grimaced a bit as it pinched slightly. He realized now why his mother said he might need the rosehip oil. He found the bottle and squeezed a bit onto his fingers. As he applied the delicately fragrant oil in the right spots, he couldn’t help but notice how sissyish his pink nails looked as he maneuvered the pink plastic ring into place.
All of this activity of course awakened his little man. It was almost like it sensed what was coming. His dainty hands trembling now, he took the other piece of hard plastic and put it over his little man. The device now seemed very small to him, but he was strangely fascinated by the way it looked. Why did it have to be pink though? With the help of the oil, however, the pieces seemed to slide right into place. Looking again at the diagram, he realized all that remained was the lock.
At that point, Josh almost stopped. This whole situation was absurd. But since he had already gone this far, he had a nearly irresistible urge to see what it felt like once he had it all the way on. Weirdly excited, he took the lock and put it into place just to see. Now the device was completely fitted together securely. He let go of it and watched it flop down and dangle. It was like he had just put the last piece of a jigsaw puzzle in place. He was immediately aware of how snug and confining the whole contraption was. He raised it slightly and watched it flop down again in the mirror. His little man was excited but now completely hidden out of sight. The pink plastic cage kept him tightly under control. It all felt strangely exhilarating, and a shiver ran down his spine. Josh knew that only one thing remained. The last step was to close the little lock. He had only agreed to try it on, after all, and now he had done that. He had done what he had said he would. He toyed absentmindedly with the little lock, but after a moment he lost his nerve…
CLICK! His heart jumped. What did he just do? He hadn’t really intended to close the lock. But it was done now! Running his pink polished fingers over his new cage, the full impact of what he had done crashed over him like a wave. It was as if something inside of him had acted all on its own. He quickly found he couldn’t touch himself down there at all! He felt a little panicked and immediately regretted what he had just done. He grabbed the instruction sheet again, this time unfolding it all the way. Surely there was another way to remove this thing! Belatedly, he saw the name of the contraption which he hadn’t bothered to read before: “Total Security Hygienic Chastity Device, Extra Small, Pink.”
Embarrassed and nervous, he did the only thing he could think to do. He put the towel back around his waist and cracked open the door. “Uhhh Mommy,” he called. “I’ve tried it on now,” he said as his little man raged pointlessly in the plastic cage. He burned with humiliation as he asked, “but could you please give me---”
“Your panties, dear?” she inquired sweetly as she finished his question for him. “Of course. I saw you didn’t take any clean panties with you in there, so here you go,” she said as she handed him a pair of panties through the open door. His train of thought interrupted, Josh was momentarily speechless at the panties his mother gave him. These were easily the most sissyish pair yet, and he was a bit surprised to see it was a new pair he hadn’t seen before. Even by his new girlish standards, these were over the top. They were made of silky white satin and absolutely covered all over in elaborate ruffles generously trimmed with delicate lace.
“After your decision the other day, I did some more online shopping for you and found these darling skirted rhumba panties on sale,” his mother explained when she saw his questioning look. “These arrived yesterday. I also got you pink, green and yellow in the same style! I just love how frilly these are with all their ruffles! Aren’t they the cutest sweetheart?”
“They are… adorable Mommy, thank you,” he replied almost without thinking. Unintentionally, he lilted out the word “adorable” in a very feminine way. “More panties,” he thought glumly. Returning to what he really wanted, Josh began again, “Uhhh but Mommy, could I have the key to this thing please now that I’ve tried it on?”
“Oh honey, does it hurt you?” she asked with genuine concern, “does it not fit correctly, dear?”
“No, it seems to fit fine,” he replied truthfully, “I’m just not sure…” His voice trailed off weakly. He couldn’t believe the conversation he was having with his mother.
“Well since it fits properly then why not see if it solves your little problem? There no harm in that is there? Surely you should at least give it a chance honey,” she said reasonably. “If it saves you from even one embarrassing accident then it’s certainly worth the trouble, right?”
“Well, yes but…” he answered slowly. In his flustered state, the feminized boy could not muster a good counterargument. “I guess I could try,” he said reluctantly with a trace of surrender.
“Remember we talked about following through on your commitments?” Gwendolyn asked. At this point, a snippet of concern had crept into her mind. She saw on her son’s face that he was still waging a pseudo macho internal resistance. That was his father’s unwelcome influence popping up again. She knew instinctively it was crucial to handle this moment carefully. Instantly, she decided she had to push through—but with finesse. It was time for another purposeful nudge. Without waiting for a reply, she delivered her closing argument in question form, “This is really a sort of commitment of self-control to yourself, isn’t it dear?” Slyly, she framed his conflict as a battle with himself.
Josh was completely pushed off balance by this idea. He had been preparing to finally assert himself. She couldn’t do this to him! This was too much!
But now he wondered… wasn’t he really doing this to himself? Uncertain, he thought back to all the choices he had made over the last few days. He remembered he could have gone to Sterncourt, but instead he chose this path. No one made him put on his first dress. Or his second. Although his misbehavior had led to this point, lying was something he had never really been able to do. At last, he reluctantly replied, “I guess so.“
“So it’s decided then. Wonderful!” she concluded. With that, she quickly changed the topic, “Now just go slip on your rhumba panties with a fresh panty liner and I’ll help you get dressed,” Pleased that she had successfully navigated this latest challenge, she added cheerily “I just know they’ll make you feel so special and pretty dear!”
It was obvious to Josh that his mother had moved on from the topic of his new accessory and considered the matter closed. Josh closed the bathroom door and dropped his towel. Chagrined, he reached for a fresh panty liner and slipped on his… rhumba panties? These were so different than his other pairs. They were very frilly and satiny on the outside but seemed to be lined with plastic on the inside. His skin tingled a little as he slid his smooth legs through the elasticated leg openings. “Sheesh!” he thought… these looked so very childish. They seemed much fuller than his other pairs as well. Looking in the mirror, he could still slightly detect the outline of his new cage even under all those white ruffles. He gingerly tapped it through his panties to no avail. All that accomplished was to give him another look at his pretty pink nails. Looking up, he saw his perky, curly perm looked every bit as girlish as it did yesterday. With his little man hopelessly trapped, Josh returned to the bedroom to get dressed.
“Oh my goodness Joshy those are just too precious!” Gwendolyn exclaimed. She appreciated the cuteness of her blushing teen in his angelic white rhumba panties. “What do you like the best about them, darling?” she asked pointedly.
“Oh… Mommy,” the cringing boy replied after a pause, “I uhh.. I guess I just like how frilly and silky they are,” he decided. Wasn’t it bad enough he had to “adore” them? Now he had to say what exactly about them he liked? Ughh! After another moment, he continued hesitantly, “But these… my… rhumba panties don’t seem quite like my others?” He posed it as a question. Just saying the words “rhumba panties” aloud seemed to heighten what a sissy he was.
“That’s right honey,” she said cheerily. “These are extra special and frilly. They also have a little added… protection… against any leaky accidents!” Gwendolyn thought with pleasant satisfaction that this morning had already been very productive. She was so looking forward to taking her feminized son to Mrs. Smyth’s shop.
Josh, meanwhile, was also thinking about his looming appointment with Mrs. Smyth. While his mother brimmed with eager anticipation, however, Josh dreaded it. Just like in his dream, he thought with dismay, the appointment with Mrs. Smyth hurtled straight at him.
For very different reasons, both mother and son exuded nervous energy.
"I've laid a nice new outfit out for you on the bed dear. I know you'll just love it!" his mother said sweetly.
Cringing, the panty-clad teen turned his gaze to the clothes lying on his pink bedspread. Securely locked in the unfamiliar pink plastic prison, his little man strained in vain. Josh let out a heavy sigh.
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So excited to find out Josh's outfit in the next chapter!
I also think it may have been a missed opportunity to give Josh the "choice" of using the ladies or the men's public bathroom. Does he want people to think he is a girl or a boy wearing girl's clothes? Perhaps this may be a choice later down the line which allows his Mom and his sister to "help" with his feminzation
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Lovely story, thank You. Love Marci
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One more decisive step on the way into sissyhood. A road with many pleasant twists and turns - all of them permanent.
Nice work and my thanks for a most pleasant journey.
Janet Marie
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Just wanted to thank you for this story. I really appreciate how you're taking your time with it.
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sissyboy1212,
I like that last chapter (actually, I like all of them).
I agree with Party Dress in eagerly anticipating the next outfit and she makes a good point about which public restroom Josh will have to choose. The ladies room seems to be the better choice.
As a consequence of dressing as a girl and wanting to fly under the radar to use the ladies room, Josh will continue to refine voice, vocabulary, and gestures/movements to match his feminine apprearance. Furthermore, to keep up a proper profile, breastforms in a bra might be introduced.
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This is a great story. Please continue. Like your other followers I can't wait for the next chapter.
If I’m right this is the beginning of day four. A lot has changed for Josh. He still seems to think that this was his choice. It would be exciting if his sister started treating him as her much younger sister. I think another choice is coming soon. Another bad versus worse type of choice. I also think this next outfit might be more embarrassing than he would ever imagine.
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Thank you bobbie99 for your nice note! Oh I haven't forgotten about Josh. His story just turned into much more of a saga than I ever expected. I'll write more as I get the inspiration. The overall roadmap for the story was laid out long ago, but I still get stuck deciding about some of the various twists and turns!
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I just read your entire story and loved it. I loved the progression up through and including the "restraint of his little man". Please continue the story of josh/joshy.
As an aside, I have read all your stories on Betty's Site and highly recommend them all.
JaimieS
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I agree completely with bobby99's and Jaimies' comments. Between the Clarissa trilogy (which I hope someday becomes a quadrilogy) and New Arrangements for Josh, you've captured the essence of this genre with a wonderful imagination and superb writing skills. Very appreciative of all you've contributed - and can only hope there will be more. Thank you!
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I will happily echo my agreement with all the other kind comments you have received as I truly enjoy & appreciate your storyline and your style. One question: since Josh is 15, don’t you think he’s a little overdue for his hormones to kick in? Perhaps a visit to a doctor (female?) might be necessary to stave that off until he can make the right choice? He might even have to make that request himself (being a special little boy). Perhaps a hormonal offset might be prescribed to keep him in balance and maybe that might cause his hormones to kick in strongly thus requiring a much greater dose which in itself might cause changes in him both physically & in attitude. You just never know how things turn out until they happen.
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Josh appearing to be dead in the water and lacking any response, I will commit myself to foregoing any further suggestions or comment for eternity.
JM
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More more more pretty please. We all love this story!!
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I read all the comments and would just like to say that there is nothing more to the long gap in this story than the fact that I just got tired of writing for a while and had other things happening in my life. I write for fun, and if it feels like a chore then I don't. Thanks to all those who seem to enjoy my little contributions.
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PART 46
Gingerly, Josh picked up the frilly white training bra which obviously matched his lovely new rhumba panties. He shivered a bit as his mother helped him fasten it snugly around his waifish chest. Gazing at the outfit on the bed, he knew it was time for him to get dressed. First, he picked up the breezy white sleeveless blouse and slipped it on. It was made of thin cotton with some cute pink embroidered detail around the girlishly rounded collar. As he delicately fastened its dainty pearl buttons, he was again keenly aware of his lovely new pink manicured nails.
Next, he stepped into the simple but feminine pink skirt. The color matched the pink embroidery on his new blouse which he left untucked to cutely hang over the top of his skirt. He was immediately aware that this skirt was on the shorter side, and his full rhumba panties made it flare out adorably. He realized at once he would have to be very mindful to keep his ruffled panties safely covered underneath. His little man was pressing urgently against the new pink plastic prison inside his panties, but it was all to no avail. It was securely locked away with no hope of escape.
Smiling happily, his mother said, “That looks so nice and summery on you, dear!” At her prodding, he was again soon wearing his new strappy white sandals. “I just love the way those sandals show off your new pedicure too,” she added sweetly. Glancing down glumly, Josh again took in his prettily polished toenails. His feet looked so dainty and girly in his strappy feminine sandals.
“Have a seat at your vanity table dear, and I’ll show you how easy it will be to care for your new perm.”
“Yes Mommy,” he said meekly as he complied and took his seat. Sitting timidly, he watched in the mirror as his mother gently fluffed and smoothed his new curls. His thoughts went back immediately to his salon experience yesterday with Miss Andrea. The feelings of being overpowered by femininity as she had given him his incredibly girlish new perm were seared indelibly in his memory now. He momentarily became lost in his rapidly swirling thoughts.
Then, his mother spoke and brought him back to the present. “See how simple that is dear? Your springy new curls practically take care of themselves!” she observed, “And those highlights really suit you too!” She casually spritzed a little styling mist on his curls and then she was done.
It was true, his new perm had practically bounced back into place on its own with little effort. He looked so girlish with his lovely cascading curls. As he gazed silently at his incredibly sissyish reflection, he barely reacted at all when his mother fastened a lovely new pink hairbow into his beautifully curled hair.
“I think this will complete the look perfectly don’t you dear?” she asked leadingly.
“Oh yes Mommy,” Josh answered almost immediately, “It’s… super cute,” he added with slightly more forced enthusiasm. He sighed again silently.
“Another day, another new outfit,” he thought glumly to himself as his mother gently guided him back to stand before the full length mirror. As he took in his adorably girlish reflection, his little man continued to strain angrily but futilely in his ruffled panties. His wispy sleeveless blouse and sweet pink skirt made for a darling look. From head to toe, Josh was once again a vision of sweet girlishness.
“Of course,” Gwendolyn observed gaily as she admired his new look, “you’ll get a fancier outfit for ‘High Tea’ this afternoon.” Continuing, she said, “I found a lovely tea-length dress in Mrs. Meriweather’s things that she said I could wear, but we’ll still need Mrs. Smyth’s help for you and Kathy.” Hearing that, Josh winced to be reminded again of the planned events for the day. With nervous anticipation, he knew today was the day Mrs. Smyth would finally “get her hands on him!” His heart skipped as he recalled again how eager she had been to get him dolled up exactly to her liking.
“Oh today is going to be so much fun, dear!” Gwendolyn exclaimed as she gently patted his bare shoulders. “I positively can’t wait to see what Mrs. Smyth has planned for you!” With growing eagerness, she finished, “I just know it’s going to be precious!”
Then, his sister’s voice startled him. “Oh my gosh, Josh you look so adorable!” Kathy said with genuine admiration. He turned his head to see her standing in the doorway with a big smile. “I just love your new skirt!” she added.
Feeling his face warming up again, he simply said, “Thanks Sis.” Practically on pins and needles, Josh knew what was coming next. There was now nothing else standing between him and Mrs. Smyth.
As if on cue, Gwendolyn said, “Oh my look at the time!” Excitedly, she told her children. “It’s nearly time to go!”
Josh’s heart fluttered again. Mrs. Smyth and her dress shop awaited.
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This is such a lovely chapter. I have a few theories about what Josh's tea outfit will be and I'm eager to see which will come true!
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You really are a gifted storyteller. Thanks for sharing.
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PART 47
Precisely at noon, Josh stood nervously in front of Smyth’s Clothing and Bridal… Bespoke Fashion for Ladies and Children since 1955. He didn’t have to stand long, as he immediately found himself being ushered through the door of the shop by his mother. Her eager anticipation was apparent as she draped an arm around her feminized son’s narrow shoulders and guided him gently but firmly inside. Kathy followed right behind them carrying a garment bag with the dress their mother would wear to the tea. A soft chime sounded as the door swung closed behind them.
As Josh gaped at the old-timey décor and all the colorful racks of fancy, frilly clothing he felt almost swallowed up by the overwhelming femininity of the place. The feel of the shop’s cool air on his bare legs made him very aware of his frilly rhumba panties under his darling pink skirt. He squirmed in dreadful anticipation when he saw Mrs. Smyth approaching with a happy smile. He shifted his sandal-clad feet uncomfortably, and he felt his little man futilely struggling again inside his new “Total Security Hygienic Chastity Device, Extra Small, Pink.” He let out an almost imperceptible sigh.
“Well hello again Gwendolyn, Kathy and of course Josh!” Mrs. Smyth said genially. “I’ve been so looking forward to this,” she added enthusiastically, “And don’t you children look smart!” She complimented Kathy on the purple polo and “trendy” denim skirt she was wearing before turning to Josh. “And Josh, that is the cutest little embroidered blouse you have on. It just goes swimmingly with that adorable skirt!” she said approvingly. “It’s understated but sweet, and it just suits you so well!” she added.
“Th-Thank you, Mrs. Smyth,” Josh replied sheepishly.
“And I just have to say again your curls are just precious! Andrea did a wonderful job on your hair. So feminine and youthful!” she went on. “And what was the name of your nail polish again? Wasn’t it Sparkly Pink or something like that? she asked.
Reflexively, Josh held out his delicate hand and looked again at his beautiful pink gel nails in a very girlish way. He remembered that he now sported “permanent” nail polish, and he couldn't help but see how it glistened prettily in the light. Reddening slightly, he replied after a moment, “It’s uhh, Baby Pink Sparkle, Mrs. Smyth.” Catching his mother’s expectant eye, he added, “I just love how shiny and sparkly it is!”
Kathy flashed her nails again too excitedly, “See Mrs. Smyth, we match just like real sisters!”
“Baby Pink Sparkle, yes that’s it, very nice,” Mrs. Smyth nodded appreciatively with a smile. “So nice to have things that sisters can share,” she added warmly.
Then, she got down to business. First, she asked to see what Gwendolyn planned to wear. After inspecting the Victorian-inspired blue dress in the garment bag, she nodded approvingly. “Mrs. Meriweather always dressed so elegantly… I think that will be splendid for you my dear.”
Turning to Kathy and Josh, she continued, “And I think I have some lovely options for the children as well!” She whipped out a tape measure and said, “First, though, I’ll need to confirm your measurements. I am usually fairly accurate with my eyeballs, but we need to double check.” With practiced ease, she took Kathy’s measurements and nodded as she finished. “Wonderful, I have a couple of dresses to choose from which will fit you perfectly my dear.”
Next it was Josh’s turn. His nerves were on edge as he held his arms out obediently while Mrs. Smyth measured around his neck and chest (or his "bust" as she called it). She measured the length of his arms, and then looped her tape measure about his narrow waist. As she took his waist measurement, her eyebrow arched slightly and she seemed to pause. Stepping back for a moment, she brought her hand to her chin in thought while she studied him carefully. Josh fidgeted awkwardly under her gaze as he wondered what she was thinking about. “Hmmm…” she said almost to herself, “I wonder…” Then, as if reaching a decision, she said, “let me just check once more.”
Putting her tape measure around him again, she remeasured his waist and this time also measured around his hips. As she took the last measurement, Josh could have sworn she brushed against his chastity cage. His face flushed again. As if in confirmation, Mrs. Smyth’s eyebrow arched in surprise and she gave him a funny look. She didn’t say anything, but she smiled at him curiously. She went on to measure around his underdeveloped thighs which for some reason mortified Josh to no end. This all seemed now very intimate and embarrassing to him. Finally, apparently having reached some sort of conclusion, she nodded silently and again stepped back.
After another moment, she turned to Gwendolyn. “I have several nice things to choose from, but there is one option in particular that I think would be just splendid for tea,” she said cheerily. “I have a beautiful matching set in my vintage collection that belonged to Mrs. Meriweather’s daughters, and no one has worn either outfit since they were donated years ago,” she said expectantly. “She had two girls, Ellen and Cindy, and Ellen was a year older,” she continued. Mrs. Smyth explained further, “They both had lovely figures, but Cindy especially was always on the slender side. Kathy can easily wear Ellen’s old dress, and I believe that young Josh here is just petite enough to fit nicely into Cindy’s outfit.”
Before Gwendolyn could respond, Kathy said excitedly, “Oh that sounds wonderful! We will get to be in matching outfits Josh!”
Josh grinned weakly at his sister and said, “That sounds… great.” The fifteen year old boy had just taken another blow to his rapidly dwindling manhood as he realized that he was more “petite” than his younger sister.
Gwendolyn nodded, “That does sound lovely Mrs. Smyth.”
“Now I must warn you, Josh’s outfit will be a bit more… boyish… but the matching pair together is exquisite,” Mrs. Smyth said. “That’s not going to bother you is it Josh, dear?” she asked hopefully, “to be dressed more like a boy for this afternoon?”
“Boyish?” Josh thought in surprise. He was completely startled. For the first time in days, he detected a faint ray of light… a path out of this mess he had put himself in! Perking up, he said eagerly, “Oh no Mrs. Smyth, that would be… I don’t mind at all something… boyish.” He had no illusions. He was certain he would still be dressed very fancily, but as least it would be in a boy’s outfit! His thoughts raced as he thought about how he might use this opportunity to find a lasting way out of skirts and dresses.
Gwendolyn, on the other hand, felt a shadow of concern. She had thought Mrs. Smyth was her ally in Josh’s journey. This was an unwelcome surprise. She had taken heed of Josh’s reaction. “Boyish?...” she asked hesitantly.
Mrs. Smyth immediately seemed to understand Gwendolyn’s apprehension, and at once she sought to put her at ease. “Oh I think you’ll approve when you see it. It’s very appropriate for High Tea. Your children will be just lovely!” Then she asked almost conspiratorially, “will you trust me?”
The two ladies locked eyes and seemed to communicate silently for a moment. Then, Gwendolyn’s expression softened, and she said, “Oh of course Dolores.” The twinkle returned to her eye and she said, “after all you’re the expert!”
Josh was oblivious to this exchange. At the word “boyish,” his imagination had practically taken flight and he’d scarcely paid attention to anything after that. He had already almost convinced himself that “boyish” meant normal boy’s clothes. Whatever outfit Mrs. Smyth had for him, he would cheerfully go along with it.
He was eagerly looking forward to taking off this skirt and getting back into a pair of pants. He’d get rid of his awful pink hairbow and try to comb his hair back into something approaching a boy’s style. Maybe they could even go back to Miss Andrea’s and take off his nail polish. He could already picture himself in a dapper sport coat and slacks… perhaps with a bow tie or something like that. He would still be dressed up, of course, but at least he’d be dressed as a boy! For the first time since he slipped on that first set of panties, things were looking up. Surely Mrs. Smyth had some boys underwear in her shop too!
“Well come along then,” Mrs. Smyth said cheerily, “Let’s get started on your outfits!” Looking at Josh, she said somewhat forebodingly, “for you especially, my special little boy, we have a lot of work to do!”
Josh, still distracted by his increasingly vivid thoughts of dressing as a boy again, completely missed the subtext in her words. Almost reflexively, he replied “Of course Mrs. Smyth… I can’t wait!” There was real enthusiasm in his voice now.
With every passing second, he envisioned himself in more and more masculine outfits. He would be on his best behavior for the High Tea and show his mother he could change his ways without dressing as a sissy girl. He decided he had to be a perfect gentleman today. Once she saw how nice he looked and how well he could behave, she would realize that he had learned his lesson! By this point, he was already mentally celebrating his return to boyhood.
Mrs. Smyth had a mental picture too. Perhaps unsurprisingly, it was nothing like Josh’s.
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Thank you so so much for two more lovely chapters of this amazing story.
Please don't feel forced or pressured by us silly demanding sissies to write when you don't feel like it. It is only the fact that we adore this story so much, and love your writing, that we sometimes forget that the author has other priorities, and needs to take a break at times.
As you say, your writing should be a pleasure, not a chore. So please only write when you are happy to do so. Thank you.
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Thank you for the new chapters!
I cannot wait to find out what Josh's outfit is!
I love this story and it's one of the few I'm frequently checking the site to see if a new chapter has been added!
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Thank you for the meaningful comments from those who are enjoying the story.
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PART 48
A short time later, Josh had already begun his fall back to earth. This was not turning out as he had dared to hope. Mrs. Smyth had told Kathy she was free to browse about the shop while they got started on her brother. “It’s going to take a little longer to get him ready, dear,” Mrs. Smyth had said nonchalantly.
In a dressing area at the rear of the shop, the sissified boy now found himself standing sheepishly in his frilly white rhumba panties and matching training bra. The cool air in the shop just seemed to make his skin tingle uncomfortably. Chagrined, he was very conscious of how much more bulky and full his panties felt now. The reason, of course, was the addition of the extra layer of “protection” underneath.
He thought back to the discussion that had occurred a few minutes earlier. “Before I show you your outfit,” Mrs. Smyth had begun, “I have to ask a somewhat personal question, dear.” She had then delicately asked his mother if he had a “small bladder.” She went on to explain, “the only reason I ask is that once we get him buttoned up in his outfit for tea, it will be quite a chore to take it all off again.” Wide-eyed, Josh listened speechlessly as she continued, “I could provide him some extra ‘protection’ to make sure there’s no risk of an accident.”
Before Josh could formulate a response, his mother spoke to him, “I think that might be a good idea, Joshy,” she began. “Remember the other day after brunch, honey?” she asked sympathetically. “You had to go tinkle and you just barely made it!” she reminded him of the episode on the beach. “You don’t want to have another accident do you honey?” she asked.
Josh opened his mouth and then closed it without speaking. Protection? More protection than the panty liner he was already wearing? What did that even mean? He didn’t know what to say, and his face flushed red at the memory of rushing to the ladies room on the beach. He remembered how he had fidgeted and crossed his legs frantically while waiting for the stall to be available. He recalled with embarrassment how he had struggled to pull his tights down and hold up his chiffon skirt without wetting himself. After several awkward moments, he realized Mrs. Smyth and his mother were still awaiting a response. Finally, he had surrendered and answered softly, “Uhh I guess so, Mommy. I don’t want to have an accident if I need to… go tinkle.” He finished with the incredibly childish term he now used to describe his number ones.
He still couldn’t believe what he had done next. Once again, his own actions and choices had led him here. On his own, he had gone behind the curtain partition. He had removed his sandals, blouse and cute pink skirt. Then, he had pulled down his frilly rhumba panties. He noticed again that they seemed to have some sort of plastic lining. He had momentarily gawked at his little pink cage, and he had tapped it fruitlessly with his prettily polished fingernails. Trembling slightly, he had then pulled on the pink youth-sized pullup diaper Mrs. Smyth had given him. He had been immediately aware of how bulky it felt. Finally he had pulled his white rhumba panties back on again over his new diaper. He was surprised to realize that they were full enough to cover it nicely. He now understood Mrs. Smyth’s last comment.
“I couldn’t help but notice your darling rhumba panties when I took your measurements, Josh,” she told him. “You should just be able to pull those right back on over this,” she had said as she had handed him his diaper. “If I’m not mistaken, those panties have some built in… moisture resistance… so they should work perfectly,” she had concluded.
So now he stood red-faced before his mother and a smiling Mrs. Smyth in his training bra and newly bulky panties. “Very nice, dear,” Mrs. Smyth said cheerily, “you’re all safe and secure now.”
On pins and needles, he watched as she held out another white garment to him. It seemed to be made of white paneled satin with little white dangling straps. “Now,” she continued, “this is an underbust laced corset, or a girdle or waist cincher if you prefer.”
“A corset?” he managed to croak in surprise. “But… uhh… I thought my outfit was going to be more… boyish?” he asked weakly. This feeble attempt at a protest was all he could muster. He had been expecting a boy’s outfit, and it was already apparent that his outfit was going to be nothing like he had envisioned.
“Oh yes, my dear,” she said quickly, “back in Victorian times, fashionable men wouldn’t dream of going without them.” She added, “corsets are historically a very masculine accessory!” She explained further, “I was very careful when I took your measurements because even with your slender figure, you are almost too big for the pants you’ll be wearing.” Then she grinned at him, “but with this, we can draw your waist in a tad and then they’ll fit you just perfectly!”
Josh stood helplessly as she quickly fastened the corset around his tummy and waist. Then, he was startled as she tugged the laces very firmly and the garment tightened significantly. Josh gasped involuntarily as he felt it compress his already petite waist. It was not necessarily an unpleasant or uncomfortable feeling, although he was immediately conscious of how confining it felt. In short order, Mrs. Smyth finished by knotting the laces securely at the small of his back and tucking the loose ends neatly away underneath a little Velcro flap.
She stepped back to check her work as Gwendolyn watched in fascination. “There now, my dear,” Mrs. Smyth observed, “you are fortunate to have such a petite figure!” Before Josh realized it, she had whipped out her measuring tape and wrapped it around his waist again. “We trimmed over three inches!” she said proudly, “that will easily do the trick!”
Josh looked at himself in the adjacent full length mirror and couldn’t help but run his prettily manicured fingers over the stiff boned panels of his corset. He was acutely aware that his waist was visibly slimmer now, and he was already finding that his corset limited his movement in an unfamiliar way. He marveled at how neatly it seemed to fit under his frilly training bra, and it was apparent that he would have trouble removing it without help. Looking down, he noticed that the corset’s little white satin straps were dangling gaily over his panties and lightly brushed against his thighs. He felt so incredibly sissyish and helpless now. Buried deep under his lovely panties and bulky diaper, he felt his little man try to awaken again in his cage. He couldn’t help but also look again at his gleaming pink toenails as he stood barefoot on the crème colored carpet. Looking back in the mirror, he found nothing “boyish” about his reflection. Unconsciously, he brushed his bouncy new curls again.
His heart fluttered a bit when he saw Mrs. Smyth begin to unzip a gray garment bag beside him. “And now, for the big reveal!” she said excitedly. With a flourish, she removed his outfit and presented it triumphantly. “Isn’t it just scrumptious my dear?” she asked rhetorically as she fussily hung it on a wall hook next to the mirror. “I told you it was exquisite,” she remarked with satisfaction, “and your lovely sister’s dress is the same matching pattern!” “Oh the two of you will be simply adorable for High Tea!” Almost to herself, she observed, “Just because it’s a tad boyish doesn’t mean it can’t also be elegant… after all, boys should be able to enjoy pretty things too!” As an afterthought, she added,” and we’ll be sure to get some nice photos for Mrs. Meriweather… I know she’ll be thrilled to see how lovely you look in these wonderful heirloom pieces that belonged to her girls!”
Gwendolyn’s eyes danced as she practically drank in the darling outfit. It was just so fussy and precious! She immediately began to notice any number of thoughtful and charming little design details. Clearly, someone had made this with love and care. Any reservations she had before were gone now. Oh she couldn’t wait to see Josh in it!
For his part, Josh was in near disbelief as he studied the incredibly fancy and sissyish outfit hanging on the wall. True to Mrs. Smyth’s words, the elaborate ensemble came with pants but there was little else about it that one could fairly call boyish. Unless, of course, you were talking about an effeminate sissy boy. Any remaining hopes he had for something more masculine were now thoroughly dashed. Josh gazed in fascination at the frilly monstrosity he knew he would soon be wearing.
“What do you think, honey?” his mother asked him excitedly, “Isn’t it lovely?”
After a pause, Josh replied reluctantly, “Oh yes Mommy… it’s… adorable.” He saw that Mrs. Smyth was already approaching again with another item in hand. Sighing, he then remembered his earlier promise to himself that he would be a “perfect gentleman” today. With halting words, he added, “It’s… it’s just… perfect.” His earlier enthusiasm was clearly gone.
“That it is,” Mrs. Smyth agreed, her eyes sparkling. Then, she asked leadingly, “Tell me, my dear, did you ever see ‘Little Lord Fauntleroy’?”
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That’s what Josh should be wearing - nappies. They are better for him. Nothing like a nappy to make him dependent on his mummy.
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Just a PSA. I'm already working on the next chapters. As I've said before the entire story has been mapped out for well over a year, but it will still be a little break before you see the next part. Life happens.
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Oh, Josh is sure to be the center of attention!
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Poor Josh. He would feel far more comfortable wearing real cloth or dispoble diaper which would do a much better job supporting his cage so it stays still unlike his thin panties. He should stay is real diapers 24/7 I have lots of little lord fauntleroy oufits online and most are kind of uglyish which is sad because I enjoyed the book and the movie :)
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thank you so much, Sissy Boy, for continuing this wonderful journey. I am eager to see if Josh wholly gives in to the sweetness of girly dressing.
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I would dearly love to see the next chapter in Josh's life. I can't wait to see what the next feminizing thing is he unwillingly agrees to.
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I just came back on the site under a different name than originally used. Just finished reading start to where this ends presently with him now in pull ups.
I was wondering how long it would take after choosing the panties over the military school. The name of the nail polish goes perfect with Josh now in pull ups. Also a sissy should never be without a chastity device and pink at that.
Please keep up the excellent writing.
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I would love to know what Josh sees in the Lord Fauntleroy suit that is so upsetting.
Is it the colour, material or the blouse that goes with it?
I had two Lord Fauntleroy suits growing up, one was black velvet with a white lacy blouse under the jacket the other light blue satin that I had to wear as a page boy when I was eleven. I wore matching white satin panties and camisole that were very lacy, white suspender belt and patterned stockings, light blue ballet flats, light pink lipstick and nail polish, my hair was done in Shirley Temple sausage curls, the blouse was translucent white nylon with a high stiff collar so I couldn't hang my head, I had to keep my head up and look straight ahead, the sleeves were very full sheer nylon with big lacy cuffs. The pants ended just below the knees and closed at the back, the jacket closed at the back and was sleeveless.
I felt like the biggest sissy, but I suppose that's what I was.
On one occasion when I was being naughty mother threatened to send me to school in the page boy outfit but fortunately never did. I did however wear it to the birthday party of one of the girls from my dance class. I was the only boy so fitted in well with all the girls in their pretty party dresses.
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Perhaps the re-emergence of the story board motivated me, but I finally began working on a long overdue continuation of this story. Sorry for the extended gap, but real life happens. I hope to post a new chapter in the next day or so.
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Thank you sissyboy for the heads up.
I have started my own continuation of the story, for my own reading.
I never intended to post it without permission but I am very keen to see how your story compares with mine.
Dancer4Fun
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Dancer4Fun I will take it as a compliment that you thought that much of the story. Thank you for not posting your adaptation, although I'd be interested to read it. Perhaps one of these days you might post it with slightly altered details/names as a stand alone story, or maybe it could be a multiverse alternate universe :)
I would respectfully ask you to let me finish off this version first before you do that though.
In any event, I initially had grand visions for the whole outline of this "short" story, but it just grew way too big. My intention now is to find a way to gracefully conclude it so that readers are not "left hanging." I figure I can always come back and write the sequel if I feel like it.
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PART 49
Pressing ahead without waiting for a response, Mrs. Smyth explained, “When Mrs. Meriweather’s youngest daughter Cindy saw the movie ‘Little Lord Fauntleroy’ she became absolutely enamored with those gorgeous Fauntleroy outfits. So much so, in fact, that her mother got a matching set of outfits made for the girls in the Fauntleroy style for a High Tea years ago. Ellen wanted to wear a dress, so that’s the one that your sister will wear today.”
With a twinkle she continued, “and luckily you are just slim enough to fit into little Cindy’s Fauntleroy suit! Isn’t it exquisite Josh?” She added admiringly, “this one really has all the ‘bells and whistles’ to make it stand out!” Smiling, she went on, “And you can see it comes with these adorable pants so as I said earlier it’s a much more boyish outfit… very dapper!”
Josh’s heart sank as the full realization that all his hopes for the “boyish” outfit he had been getting excited about were completely dashed now. If anything, this was going to be worse than wearing a dress, because everyone would know he was a boy… a complete sissy boy!
In a shaky voice, he replied, “Oh… yes Mrs. Smyth. It’s… lovely.”
Mrs. Smyth then said gaily, “I can’t wait to see it on you!” Gwendolyn watched this exchange with a very pleased look on her face. Mrs. Smyth then explained, “Of course, it’s quite the process to put you into it properly since it has so many wonderful extra details and accessories!”
“Let’s get started, shall we?” she began, “and I’ll tell you a bit of the history of Fauntleroy suits as we go along which I’m sure you’ll find interesting.” Mrs. Smyth continued, “first, here are your stockings.” She guided him to sit on the little stool in the dressing area and handed him a pair of long white stockings. “Put these on, Josh. Elegant stockings are the foundation of a proper Fauntleroy look, usually white or cream-colored.” She offered, “I prefer the white because they make a much more striking contrast in my opinion.”
Under her close supervision, Josh rolled the heavy, ribbed stockings over his manicured toes and up his legs, first his right and then his left. He shivered as he felt the clinging sensation of the thick stockings encase his slim legs. He could just barely reach his toes with the confining corset restricting his movements, so Mrs. Smyth helped him get the stocking toes straight. He felt so emasculated seeing his pretty pink nails shimmer as he slid into the elaborately patterned stockings. Next Mrs. Smyth had him stand back up so she could straighten his stockings. Then, she fastidiously clipped his stocking tops to the little satin straps attached to his corset. She nodded approvingly as she stepped back to inspect her blushing, bestockinged charge.
The confining feel of the stretchy white stockings tickling his thighs caused his “little man” to tingle mercilessly, but it was safely secured in its pink plastic prison down under his diaper and frilly white rhumba panties. Standing in his stockinged feet, Josh saw in the mirror just how delicate he looked. His confining hosiery was now smartly clipped to his white satin corset with the delicate straps running prettily over his frilly panties. He grimaced again at how much bulkier his panties seemed with the added diaper underneath. His ruffled training bra sweetly caressed his narrow torso in such a delicate way, leaving just a tiny gap of skin above his tightly fastened corset.
“Now the pants,” Mrs. Smyth said next. Josh sighed.
“These darling little knee pants and the matching coat are made from velvet which is the traditional style. Luckily for you the air conditioning in the restaurant works quite well. Otherwise, you might get too hot wearing it. Now most Fauntleroy suits were made in darker colors like black or navy blue, but Cindy’s favorite color was pink, so here we are. Velvet is such a wonderfully luxurious fabric… here feel it Josh” she directed.
Josh reached out with his prettily manicured hand to touch the pants. As he felt the texture of the rich material, he shuddered a bit knowing he would be wearing these incredibly juvenile pants momentarily. The short knee pants were a dusty rose-pink color, and he realized that his Baby Pink Sparkle nails were a very similar shade of pink. “Great…” he thought.
“These pants are just precious, and based on your measurements they will be a perfect fit on you!” Mrs. Smyth said with satisfaction. “See all the lovely details… the whole outfit is truly exquisite!” she added. Then, she directed, “Let’s try them on.”
In short order, Josh found himself wearing the darling knee pants, and he could already feel the warmth of the rich velvet. He saw immediately that there was no fly. When he mentioned this minor detail, Mrs. Smyth had responded, “that’s one of the reasons I think you’ll be grateful for the added protection of your… diaper… dear. Just as a precaution, of course.”
Josh winced slightly. Now that word he had tried to ignore had been said out loud: "Diaper!" Somehow it had been avoided up til now. He glumly had to accept that he was in fact now a diapered sissy. Once again, he looked at his reflection in the full-length mirror.
The pants had an elasticated waist, and he had noticed several buttons sewn inside the waistband when he put them on. The sissyish pants billowed out a bit over his thighs and reached down to just above his knees. They were much more like shorts than pants in his opinion. They were sweetly tapered and gathered at his knees with more elastic. Fussy white lace frills adorned the hems and encircled his slender legs. Motionless, he watched in the mirror as Mrs. Smyth snugly buttoned the knee pants just above each knee and then knotted off the dangling ribbon ties at the bottoms of the hems, leaving adorable little pink bows nestled in the white lace that cascaded from each pants leg.
“Oh, that corset did the trick dear,” Mrs. Smyth exclaimed happily, “they fit you beautifully... with even a bit of room to spare!”
“My, my... they are absolutely gorgeous Joshy,” his mother gushed. Then she added with a slight twinkle of irony, “you’re going to such a handsome little prince today!”
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I would love to know what Josh sees in the Lord Fauntleroy suit that is so upsetting.
Is it the colour, material or the blouse that goes with it?
I had two Lord Fauntleroy suits growing up, one was black velvet with a white lacy blouse under the jacket the other light blue satin that I had to wear as a page boy when I was eleven. I wore matching white satin panties and camisole that were very lacy, white suspender belt and patterned stockings, light blue ballet flats, light pink lipstick and nail polish, my hair was done in Shirley Temple sausage curls, the blouse was translucent white nylon with a high stiff collar so I couldn't hang my head, I had to keep my head up and look straight ahead, the sleeves were very full sheer nylon with big lacy cuffs. The pants ended just below the knees and closed at the back, the jacket closed at the back and was sleeveless.
I felt like the biggest sissy, but I suppose that's what I was.
On one occasion when I was being naughty mother threatened to send me to school in the page boy outfit but fortunately never did. I did however wear it to the birthday party of one of the girls from my dance class. I was the only boy so fitted in well with all the girls in their pretty party dresses.
I should have responded to this much earlier, but I am so jealous! I would love to have been put into your blue satin page boy outfit as a boy. So lucky!
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PART 50
Next it was time for the extraordinarily fancified blouse that had mesmerized him ever since Mrs. Smyth had hung it up in front of him.
He watched with rapt attention as Mrs. Smyth took the pleated white silk blouse off its padded hanger. Seeing the thin fabric up close now, Josh wondered nervously if his training bra and corset would be visible underneath it. As if reading his mind, she told him, “No need to remove your bra, honey. All this pretty detailing up front will keep it from showing through.” Reluctantly, Josh slowly reached to take the ornate monstrosity and put it on, but Mrs. Smyth chuckled and said, “Oh no dear, just stick your arms out in from of you… this one buttons in the back!” She continued, “there are no buttons in front to distract from all this gorgeous ruffling, but don’t worry, I’ll have you sorted out in a jiffy!” Josh held his arms out nervously as she instructed, and then he felt the cool silk gliding up his arms as she pulled it up on him and wrapped it around his chest. As she buttoned him up from behind, he could feel the billowy silk being gathered more and more closely around his torso. It gave him little tingles as it slid against his sensitive skin. His heart was beating more rapidly at all these new sensations. After fastening what seemed like an inordinate number of buttons, she finished the last one to bring the collar close around his neck.
He was a bit startled when she next gripped the waist of his pants. At first, he thought she was just tucking his blouse in, but he quickly realized what the buttons inside his waistband were for.
Speaking again, Mrs. Smyth explained again, “true to the style, the blouse buttons neatly to your knee pants so you’re guaranteed to keep a lovely, polished look… no sloppy untucked blouse for you today!”
When she had his blouse fully attached to his pants, Josh could see in the mirror that his pants gathered very snugly at the waist with the help of the elastic and the corset underneath. The bottom of his blouse, now securely buttoned to the pants, was also now gathered petitely at the waist. It then billowed out a bit more as it rose up his chest. Multiple darling layers of lace puffs and ruffles dangled breezily down the pleated front of the shirt and nearly reached his belly button. More elastic clung around his wrists at the ends of the pleated sleeves, and additional lace frills just like those at the hems of his pants danced merrily around each wrist. Another prominent feature of his new blouse was a large floppy white silk bow fastened close at the front of his throat. The ostentatious bow rested adorably above all the other frills and ruffles beneath it. But it also seemed to Josh that the sleeves were much too long, as there were stiffly starched lace cuffs with elaborate patterns extending down well past his fingertips.
“Mrs. Smyth,” he said with some confusion, “I think this shirt… er, blouse… is too big.” He held out his hands which were now completely hidden by the large, drooping cuffs.
“Oh no, my dear,” she corrected him, “that’s a perfect fit… you’ll see shortly!”
Continuing to work, Mrs. Smyth took a shiny satin sash matching the color of the pink velvet and ran it through belt loops on either side of his pants. She cinched it tightly around his waist with a very secure knot and then tied a flouncy sash bow on top. The bow was offset close to his right hip with the free ends hanging sweetly down the front of his leg. “I think that pink satin sash makes such a lovely contrast with the velvet. The sheens of the different materials work well together and create such a charming aesthetic,” she pointed out. “And the sash adds a bit of sassy flair to your ensemble!” she added with an impish grin.
“Oh Josh,” Gwendolyn nearly squealed, “you look so devil-may-care and cheeky with that sash… such a dashing little rascal!” Of course, she was thrilled with how childish and effeminate the whole outfit was. She couldn’t help but talk to him in much the way one might teasingly encourage a toddler getting dressed up as a “scary” pirate for Halloween.
Josh’s cheeks reddened to be spoken to this way. He had no enthusiasm for any “sassy flair” and “devil-may-care” in no way described the way he felt. Instead, he was being progressively trapped in ever more effeminate finery. And unlike the previous days when he could just pretend to be a normal little girl, everyone today would know he was a boy. But all he could say was “Oh thank you Mommy.”
“Before we do the coat, let’s get your shoes on shall we dear?” Mrs. Smyth jumped back in. “I want to save the best part for last!” Once again, she seated her sissified charge on the little stool.
Josh groaned inwardly as he picked up her last remark about saving the “best part for last.” With each new added embellishment to this nightmare of an outfit, the sensations of being helplessly trapped only grew. It was plainly apparent at this point that there was no way he would escape his Fauntleroy suit until Mrs. Smyth and his mother decided it was time. Depressingly, he also realized what an ordeal it would be even to use the bathroom… and now he fully understood why he was wearing a girls pullup diaper underneath all his other layers of sissified clothing. The way his sash was tied so firmly around his waist and covering the waist buttons meant that removing his blouse would be quite a challenge… and there was more to come! For some strange reason, this realization made his little man twitch again in a futile attempt for attention.
Mrs. Smyth pulled up a shoe fitting stool in front of him and sat down. In short order, she pulled a pair of very sheer nylon anklets onto his already stockinged feet. He sighed softly to see that they were trimmed with several rows of dainty white lace ruffles. “This is such a cute extra touch my dear… all these details matter to pull the whole look together!” she said cheerfully. Once the stretchy anklet socks were in place with all their extra frills, she began strapping him into his shoes.
“You are fortunate to have such small feet for a boy,” she spoke again. “Back in the day, most boys in Fauntleroy suits would wear leather shoes, but Mrs. Meriweather was able to find these for little Cindy to wear with her outfit, and they seem to fit you nicely.”
Josh gawked as she buckled the pink velvet Mary Janes onto his petite stockinged feet. They were a pale dusty pink color which almost perfectly matched his knee pants. Darling little straps with delicate gold buckles secured them on his feet, and they had the cutest tiny velvet bows on the rounded toes. They were ballet flats with no heel, and they paired cutely with his frilly white anklets. Clearly, there was nothing “boyish” about these shoes at all.
“Oh, my goodness Joshy” his mother chimed in, “your Mary Janes are just to die for!”
Josh sighed heavily.
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Hello Sissyboy,
If you would like to read the 30plus pages I have written I could send them to you via the email link on your profile page if you like.
I would not be inclined to post them even after you finish the story of Josh as my style is nowhere near as descriptive as your own.
It would be nice to get your opinion of my story line and style.
Thanking you in anticipation,
Dancer4Fun.
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( " at " ) Dancer4Fun,
Thank you for that offer, and I am flattered that you would be interested in my feedback on your writing. Still, I would not want to read your version until I am finished writing mine. I definitely appreciate the kind gesture and hope to take you up on it when I put the pen down on Josh. I am just worried my story would be overly influenced by yours if I read it, and I don't want to start plagiarizing. But I am confident your version is interesting and lovely. 😘
And you are absolutely correct that I am very guilty of going into great (sometimes excessive) detail on the sissy experiences in my stories. That's my favorite part of this very specific genre, and I often find myself wanting more when I read some of the other stories. To each their own, but I personally enjoy the stories that really describe what the sissy is experiencing. If a young hero is just made to wear a dress and get embarrassed, I often feel like there is so much more that could have been said. Again that's me.
Thank you again for the offer, and I hope to take you up on it soon... just not today.
Hugs and kisses! 😘
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Thank you so very much for the continuation of this delightful story after the long time gap between chapters 48 and 49. It is beautifully written and creative in its content - one of the best stories I've encountered here. Hoping you will be sufficiently motivated to carry on. Again, my thanks.
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Hello Sissyboy.
Thank you for your reply. I appreciate your not wanting to be influenced by my writing, I would be delighted to wait until the conclusion of Josh.
My comment about your description of every item of Joshy's wardrobe and his feelings about it is definitely not a criticism but a compliment. I feel it makes the story so much more enjoyable.
I just wish I had the ability to write in the same manner.
Hugs Dancer4Fun
ps. I can't wait for the next exciting chapter.
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Thank you Dancer4Fun and jenniesissy for your kind comments. I'm glad you are enjoying the continued saga.
Expect the next part in the next few days :)
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PART 51
“NOW it’s time for the jacket,” Mrs. Smyth said a little more energetically. She was beyond pleased at her handiwork so far and getting excited about the finished product. “I’m so happy that I finally got my hands on you, and I’m certain you will be thrilled with the end result! Such a refined and fetching look for a very special boy!” she added.
She carefully put the teenager into his short velvet cutaway jacket. As Mrs. Smyth helped him pull the long silk sleeves of his blouse through the jacket, it seemed to him that the jacket sleeves were on the short side as well. Then Mrs. Smyth meticulously set about straightening his sleeves just so. As she worked, he saw the petite jacket barely reached to his waist, and it was clearly intended to be worn open. The bottom of it only grazed the top portion of his pink sash, ensuring the shiny satin and fussy sash bow remained on full display. The fitted jacket felt childishly small on him. Like the pants, the velvet jacket had a rich texture and a distinctive soft sheen. It was also beautifully adorned with shiny brass buttons, and Josh noticed now that they were monogrammed with someone’s initials in fancy script. He read the letters “SSY” and was somewhat confused. A moment later, an unpleasant thought made his heart sink. He asked timidly, “Mrs. Smyth, are these buttons supposed to say ‘SISSY’”?
Mrs. Smyth gave him a funny look, and then she broke out in a short laugh, “I hadn’t thought of that dear, but I guess they could stand for ‘SISSY’ if you like! Of course, it is true that the Fauntleroy suit became strongly associated with things that were cultured and refined, and less sophisticated people often attached the term ‘sissy’ to the boys who wore them. As an unfortunate result, most boys grew extremely reluctant to be seen in them, although the suits remained quite popular with their status-conscious mothers. It usually took a very insistent and determined mother to get an older boy dressed in a Fauntleroy suit, but the style remained common with younger boys. Wearing one at your age would have made you something of an outlier even at the time. I personally think that instead of being thought of as something ‘sissy,’ however, the look is better viewed as a callback to a more genteel and cultured time. Still, that ‘sissy’ idea has persisted."
"In any event," she continued, "I believe Mrs. Meriweather took the monogrammed buttons off an old blazer she owned as a child and repurposed them for this suit. It had nothing to do with the so-called ‘sissy’ history of these suits. You see, her maiden name was Young, so Sylvia S. Young was her name before she married.” Chuckling slightly again, she added “So that’s how you arrive at ‘SSY’ for her initials… ’SISSY’ indeed!”
Josh gaped in near disbelief at this convoluted explanation and meekly replied, “Oh… OK, Mrs. Smyth. Thank you for explaining all that.”
“Well Joshy, I think Mrs. Meriweather’s SISSY buttons add a wonderful personal touch to your Fauntleroy jacket, don’t you?” his mother teased him gently. She thought to herself that she would have fit right in with those very determined mothers of the past!
“Uh, yes I guess so, Mommy,” the embarrassed teen agreed.
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You really are an amazing storyteller.
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We ALL love this story
Thank You sissyboy for continuing
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Thank you both for your kind comments.
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PART 52
As Mrs. Smyth finished straightening his jacket and blouse to her satisfaction, she spoke again, “Fauntleroy jackets were designed to fit snugly and remain unbuttoned to showcase all the wonderful embroidery and lacework of the blouse underneath… it would be such a shame to hide all those delicate frills, wouldn’t it my dear?”
Indeed, the multiple layers of elaborate ruffles on his blouse stuck out prominently from the open jacket and practically spilled down his front. “Now let me show you why your darling blouse fits perfectly,” she added.
Again standing before the large mirror, Josh watched in fascination as she folded the blouse’s long lace wrist cuffs back up around his jacket sleeves. He realized that the cuffs of his blouse had little fasteners that secured the cuffs to the jacket sleeves. He stood meekly as Mrs. Smyth arranged them properly around his slender forearms. Worn this way, the jacket’s lustrous velvet contrasted beautifully with the intricate patterns and openings in the elaborate white lace on top of it. He was shocked to see that his oversized cuffs reached nearly back to his elbows, and with the buttons holding them they would obviously stay right in place. The remaining frilly fringes at his wrists now danced cheerily around his hands, and once again he could see his pretty pink manicured nails sparkling in contrast to the white frills.
With the cuffs of his blouse now daintily flipped back, Mrs. Smyth neatly knotted the little pink ribbon ties around his wrists into pink bows that matched the ones at his knees. The bows created such a charming contrast with his flouncy white wrist puffs. And of course, with the cuffs of his blouse attached like this around his forearms, he understood the jacket would not come off anytime soon.
“I must say again that the ladies at Andrea’s salon did a marvelous job on your nails… so pretty! And they look so lovely with the rest of your outfit,” Mrs. Smyth said admiringly. “What was the name of that color dear? It was something like ‘Sparkly Pink,’ wasn’t it?” she asked.
Reddening again to be reminded of how complete his descent into sissyhood was becoming, he replied, “It’s, uh… ‘Baby Pink Sparkle’ Mrs. Smyth.”
“Yes that’s it! ‘Baby Pink Sparkle!’” she beamed. To drive home her point, she added, “That’s such a fitting color for a special boy finding his softer side I would think,” she went on, “I’ll bet it makes you feel very feminine!” She asked, “Did you pick it out yourself?”
Grimacing slightly, the teenager replied, “Uhh… Kathy helped me pick it out, Mrs. Smyth” Catching his mother’s eye, he added, “I just love how girly it makes me feel!” A moment later, Josh couldn’t believe the words that had just spilled out of his mouth almost automatically. His little man twitched again futilely in its plastic cage.
His ordeal continued.
“Now for the crowning touch,” Mrs. Smyth announced triumphantly. The sissified boy involuntarily held his breath as she removed a large piece of heavily embroidered lace from another padded hanger. The pattern matched the lace cuffs now running up his arms. As she carefully unfolded the beautiful fabric, Josh felt his pulse quicken slightly. Then, she lifted it up under his chin and he caught the distinctive scent of freshly starched laundry. As she wrapped it around his neck, he had a sudden, overpowering sensation of being enveloped in feminine lace. He twitched like a nervous rabbit when her fingers grazed his throat as she gently but purposefully took hold of his blouse collar.
Mrs. Smyth began meticulously fastening the piece of delicate fabric to the collar of his blouse. “You’re going to just adore this, I’m sure!” she said with genuine enthusiasm. He could see now there were several tiny pearl buttons on his blouse collar he hadn’t noticed earlier, and she was using them to secure the new item in place. It was immediately obvious that this was a very fussy and oversized lace collar. It was open in front so that it didn’t hide his floppy silk bowtie, but otherwise it completely encircled his neck.
“Large lace collars were an integral part of a proper Fauntleroy suit, my dear, and yours is no exception!” Mrs. Smyth explained. “This one, like many historical ones, is large enough that it needs to be attached as a separate piece instead of being sewn to the blouse itself.” Josh watched as Mrs. Smyth expertly arranged his lace collar so that it draped daintily across his shoulders and down from his neck in back. It was so large that it extended nearly off the ends of his narrow shoulders and hung sweetly down the top of his jacket front. Next, she used some tiny safety pins to attach the collar directly to the velvet jacket at his shoulders. When she was done, the pins were completely hidden underneath the lavish lace. “We want your gorgeous collar to have a slight bounce to it, dear, but those pins will ensure it stays tidily in place,” she added, “and you can see that while it reaches down generously in the front, it is cut at an angle so that it doesn’t hide that elegant silk blouse!” Stepping back to admire her work, she concluded, “the whole effect is just exquisite!”
“Oh Dolores,” his mother piped up, “it looks so darling on him!”
For some reason, this extraordinarily large and fancy collar had an outsized effect on Josh as he looked at himself in the mirror. Despite all the feminine indignities he had suffered so far, his dainty Fauntleroy collar seemed to hit him with an unexpected intensity. He had never worn anything like this even as a young boy, and it all just seemed inescapably stifling. He felt a sudden welling of tears and fought very hard the urge to cry.
Sensing the boy’s whirling emotions, Mrs. Smyth said gently, “I know how you must feel, dear.” She patted him lightly on his shoulder and added, “I think it’s beautiful too.”
Mrs. Smyth paused and let the moment pass. Then, she regained her energy. She beamed triumphantly as she hovered over her helpless charge and addressed him again, “we’re almost there, my dear!” With satisfaction evident in her voice, she added, “we have just one last little flourish to take care of!”
“What else could there possibly be?” the feminized teenager thought dejectedly as he stared at his incredibly childish and prissy image in the mirror. He quickly realized that even the slightest movements made the oversized lace collar and the frills on his blouse rustle adorably… a constant reminder of his sissified state. As any remaining traces of his masculinity were relentlessly smothered by Mrs. Smyth’s unyielding attention, the feminized teenager could only wait to find out what she had planned for him next.
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Wonderful to have you back. I very much appreciate that you present in such detail (and I believe with accuracy) Josh’s thoughts and sensations, with each lovely girly development.
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The next part will be a bit of a transition, so it's somewhat shorter than most of mine. It's probably (mostly) gratuitous fan service, but that stuff definitely has a place in our genre 😜
I plan on posting it sometime later tonight as I continue to figure out how Josh's saga comes to a logical stopping point (at least for now.)
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PART 53
Mrs. Smyth retrieved a cardboard box and removed a large pink velvet hairbow which matched his Fauntleroy suit. “Of course, that’s a nice hairbow you’re wearing today, but it doesn’t really match the rest of your adorable outfit,” she offered smilingly. Of course, Josh expected she would immediately pin it into his curly hair, but instead she set the hairbow down on a side table. “Have a seat please dear,” she directed as she guided him back onto the little stool.
“Gwendolyn, would you mind assisting me and taking out the hairbow he’s got on now?” Mrs. Smyth asked his mother.
“Of course, Dolores, I’ll hold onto this one for safekeeping,” his mother answered. She removed the smaller pink bow Josh had been wearing all morning, and the helpless boy could see his mother’s eyes were still twinkling.
Meanwhile, Mrs. Smyth opened a small cabinet and removed a pink nylon salon cape. “We just need to do a little touch up on your hair dear, and we want to make sure and protect your lovely suit,” she said as she snapped the nylon cape around his neck. Then she retrieved a small spray bottle from the cabinet and instructed, “Close your eyes dear.” Josh complied meekly, and he could feel her spraying his hair with whatever was in the little bottle. The spray had a clean and slightly sweet fragrance, and he could feel the cool mist on his neck as she liberally coated his girlish curls with it.
“This is a heat protectant for those wonderful curls dear,” Mrs. Smyth explained, “with your perm and highlights, we must be very careful to not damage your hair.” Once she was finished, she set the spray bottle down, and as Josh opened his eyes, he saw that she had picked up her cellphone to make a call.
A moment later, whoever she was calling picked up. “Oh, hello Andrea!” he heard Mrs. Smyth say cheerily. After a pause, she continued, “Yes, he’s all ready for you! I just sprayed him with the protectant, so it should be dry by the time you get here!” After another moment, she concluded, “Wonderful, we’ll see you in a few!”
Turning back to Josh, Mrs. Smyth explained gaily, “Miss Andrea is going to step over here and just touch up your hair for the Tea.” She continued, “after all the wonderful work she did on you yesterday, I thought it would be best to have an expert finish everything off!”
Long minutes passed, and Josh fidgeted nervously under his pink salon cape while Mrs. Smyth and his mother gaily talked about how gorgeous his outfit was and how lovely the tea would be. It was obvious at this point that his sissification would be on full display for all to see. It was excruciating to think about. As he fretted on the little stool, his senses were continuously bombarded with reminders of all the lavish feminine details of his new wardrobe. In one moment, he could feel his little man straining in its extra small pink cage. In the next, his frilly collar would teasingly tickle his throat. At times, the warmth of his lush pink velvet Fauntleroy suit seemed as if it would suffocate him. Then he would suddenly become conscious of how his white ribbed stockings clung so tightly to his slender legs. And if he tried to take a deep breath, he would instantly feel the confining tightness of his stiff corset. It was all very dizzying, and the seconds seemed to drag.
And yet, he was still startled when the bell at the front of the store rang, indicating that someone had entered the dress shop.
“Oh excellent!” Mrs. Smyth exclaimed, “there’s Andrea now!”
“Hello,” he heard Andrea call out cheerily, “where is our Little Lord Fauntleroy?”
“We’re in the back,” Mrs. Smyth answered immediately. “I have him all ready for you!” she added eagerly.
Increasingly resigned now to his inevitable fate, Josh sighed heavily. When he saw Miss Andrea enter the dressing area and grin happily at him, he somehow managed to muster a weak smile in return.
“There you are!” Miss Andrea said energetically, “let’s get you ready for the Tea!”
“Thank you, Miss Andrea,” Josh said softly, “I can’t wait…”
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I am oh so eager to see just what's going to happen with Josh's hair. He's already so sissy and pretty! How could it possibly get better?
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Just caught up on this story and wow... This is really an amazing story. You are so gifted with the detail of your descriptions. So many times my toes curled in sympathy at how humiliating this whole ordeal is... Right before I squealed in delight!
Thank you so much for sharing this with us!
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I just wanted to concur with RibbonBound there. This might be the best story on the forum. Really appreciate the slow pace and the detail of the descriptions. Wonderful!
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Thank you for those lovely comments. In truth, I am just trying to write the story I want to read. I am very pleased to know that others enjoy it too. Thank you again. <Curtsy> :)
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PART 54
Miss Andrea quickly took charge. “I see Mrs. Smyth has gotten you all ready for me,” she said with a smile. “I’m so pleased with the way your very first perm and highlights turned out,” she said as she ran her skilled fingers through the effeminate teen’s curly locks. “It’s such a cute and trendy style for a pretty little girl today, but it’s a tad modern for Little Lord Fauntleroy,” she explained.
Josh cringed to be reminded so plainly in no uncertain terms that his new permanent hairstyle was unmistakably intended for a girl. The words “very first perm” lingered unpleasantly in his brain. They implied that there would be a second, third and perhaps many more other perms awaiting him in his increasingly girlish future. His thoughts raced as Miss Andrea spoke again.
Miss Andrea continued, “So Mrs. Smyth asked me if I could style your lovely curls into something a bit more period appropriate for the Tea.” Josh watched in awful anticipation as she plugged in a curling iron and placed it on the little table next to the hairbow. With a twinkle she added, “It’ll take us just a few minutes, but I think you’ll be thrilled with the result.” She spun the little stool around so now his back was to the mirror. As she lovingly caressed his beautiful curls, she asked him, “do you remember how I explained to you yesterday what a versatile hairstyle you have now?”
Stammering slightly, Josh answered, “Ye-Yes Miss Andrea, I remember that.” He was beginning to redden again. All the sensations and memories from his “day of beauty” under Miss Andrea’s care were now indelibly etched in his brain. From his “first perm” to his Baby Pink Sparkle nail polish, he vividly remembered every detail of the tidal wave of femininity that washed over him yesterday. He doubted he would ever forget how girlish it made him feel.
A moment later the curling iron was ready. Josh sat meekly as Miss Andrea took it and set to work on his hair. “Your new style just opens up so many adorable possibilities for you!” she said admiringly.
Now Mrs. Smyth spoke again as she watched Miss Andrea work her magic on the feminized teenager. “In Victorian times, many doting mothers also insisted on putting their sons in ringlet curls to go along with their Fauntleroy suits, and it became a hallmark of a proper Fauntleroy look.” She added a little mischievously, “of course the boys balked at getting their hair curled just as they did wearing the suits for those same ‘sissy’ connotations I mentioned earlier.” She continued, “fortunately for us, there’s no need for the discussion since you’ve already got the curls.” She concluded, “Miss Andrea is just going to tease them into some nice ringlets for you!” She smiled in satisfaction.
“Ringlets?” Josh asked hesitantly. “Isn’t that what I already have?” he asked hesitantly. The word “ringlet” just sounded so sissyish to him as he said it.
“Oh no honey,” Miss Andrea corrected him, “ringlet curls are a specific type of curls with a very particular look.” She continued, “your new perm will naturally fall into a very modern loose curl, but with this curling iron and some hairspray we will get you into some proper ringlets.” She explained further, “you might have also heard them called princess curls or corkscrew curls or even sausage curls, but they are a very distinctive and bouncy style that was popular back in the day.”
“Princess curls?” Josh asked dejectedly as his dwindling boyishness took another shot. His “boyish” look for today would obviously be nothing of the sort.
Miss Andrea giggled slightly and said teasingly, “well that’s one of the terms for them anyway, and you’re certainly as pretty as a princess!” Then Miss Andrea explained further. “Since we’ve already put your hair through some processes yesterday, I’m just using a lower heat setting to protect it.”
Josh’s thoughts continued to whirl. As Miss Andrea worked on him, he couldn’t get the term “princess curls” out of his head.
Gwendolyn was very pleased as she saw her son’s ringlets begin to appear. “Josh, I think you’re just going to adore your ‘princess curls,’” she couldn’t help but add. Almost without thinking, she put a little extra emphasis on the word “princess” to drive the point home.
The feminized teen cringed again as he felt his new “princess curls” taking shape. He dreaded seeing the final product, but he knew it would be over-the-top effeminate. Along with his continued emasculation, he was being forced to learn an entirely new vocabulary of things that other teenage boys never bothered with. Everything from petticoats, to gel manicures, to corsets... and now ringlets.
“Princess curls… Ringlets… Sausage curls…” he repeated the new terms silently to himself, “I’m getting princess curls.”
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Josh is in such good hands. Princess curls will surely complete that outfit and make him the center of attention
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PART 55
Miss Andrea skillfully twisted and pulled his hair as she methodically wrapped sections of it around her curling iron. Already warm with embarrassment, Josh could feel the additional heat from the curling iron near his scalp. With his back to the mirror, he could only imagine what he would look like when she finished. He nervously shifted a bit in his seat and felt his diaper crinkle unpleasantly in his velvet pants. He was not used to its extra bulk. He twisted again slightly and felt the tightness of his tightly laced corset. He was growing very restless and uncomfortable now while Miss Andrea curled his hair.
“Please sit still while I work, Josh,” Miss Andrea gently chided him, “this won’t take us long.” Then she recalled how she had buckled him in yesterday and said with a twinkle, “maybe I need to strap you back into my salon chair!”
Josh cringed to be reminded of that experience.
“You’re so fortunate you already have your darling perm!” Mrs. Smyth interjected. “Back in the day, boys had to sit still for long stretches of time while their mothers got their ringlets just right, but yours will be done in a jiffy thanks to Miss Andrea!” she continued.
She went on, “I find it fascinating that mothers commonly saw the Fauntleroy look as a reflection of their own social status… the fancier the better! In fact, it often became a competition among some of the most zealous mothers to outdo each other with their sons’ elaborate outfits. Thus, many boys were put into increasingly fancy ringlets and ever more adorable suits no matter how much they squirmed and protested!” She observed, “in many respects, the boys were often just swept along for the ride as their mothers tried to one-up each other.” She concluded with a stifled snort, “so, I suppose the idea of Fauntleroy suits being the sign of a ‘mama’s boy’ was more or less accurate.”
“How interesting!” Gwendolyn replied with a hint of a smile. Turning to her son, she said “now stop YOUR squirming, Joshy, so Miss Andrea can finish your ringlets.” Looking down, she frowned slightly and said, “do you need another reminder about your knees, dear?”
Josh immediately clasped his knees back together. Josh couldn’t help but think that he had sat still quite long enough yesterday in Miss Andrea’s salon to get his perm and highlights. He knew exactly how humiliated those “mama’s boys” of the past must have felt. Then, he reddened again as he recalled the shame of having a “little squirtie” in his panties while he got his hair permed yesterday.
Meanwhile, Gwendolyn reflected on Mrs. Smyth’s comments as well. She felt a warm surge of satisfaction, and she felt a kinship with those strong-willed mothers of days gone by. Smiling, she said to Josh, “I will be very proud to show off my ‘mama’s boy’ today, honey!” Beaming, she said, “We’re so lucky that Mrs. Smyth and Miss Andrea have pulled out all the stops for you!”
At this, Mrs. Smyth smiled broadly, and Miss Andrea chuckled. Josh, on the other hand, sighed softly and tried to sit very still with his knees together.
After a few more excruciating minutes, Miss Andrea announced, “I think that should do it.” Then she instructed him, “Close your eyes, honey.” Josh complied and immediately felt a blast of cool hairspray hitting his hair as she shielded his forehead with her other hand. She sprayed his hair very liberally, and Josh could smell the distinct odor of the hairspray as the can hissed. “This product I’m using has an extra-strong hold so we can really lock your ringlets in nicely, dear.” After it seemed that she emptied nearly the entire can on his curls, she told him he could open his eyes. She then used a hair dryer with a diffuser to dry his hair with gentle cool air. The overpowering smell of the hairspray lingered in his nostrils.
Then, she picked up another can and had him shut his eyes again. “This is a high shine finishing spray which I absolutely love,” she explained further. As she coated his hair again, she said, “this product is nice because it has some wax in it to produce a lustrous high shine and texture… it will really make your curls pop!”
Finally, she was done with the finishing wax spray. Lastly, she picked up the oversized pink velvet hairbow that had been awaiting him on the side table this whole time. “I suppose all we have left to do is your hairbow,” she announced with a grin. “Let’s get it on you, shall we?” she asked rhetorically.
Josh mustered a weak smile.
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I know Josh is just nervous, but I hope he'll be suitably grateful and show it once he sees the final result. They're putting so much time and effort into his outfit and hair!
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LOL. I think he's happy... he just doesn't realize it yet :)
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LOL. I think he's happy... he just doesn't realize it yet :)
They mean well! It's just a complicated transformation and it's all for the best. I'm certain he'll realize how much better off he is
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PART 56
As Miss Andrea carefully pinned the big floppy velvet bow into his bouncy curls, Mrs. Smyth spoke up again with a slight chuckle, “it was quite common for boys to wear large hairbows with their Fauntleroy suits back in the day, so this would have been considered a typical boy’s accessory.” She added, “sometimes the mothers would also put their sons in adorable boater hats with their suits, but I wouldn’t dream of covering up your gorgeous sausage ringlets!”
“Oh my goodness Joshy, your ringlets are just darling!” His mother exclaimed.
Finished now, Miss Andrea spun him back around to face the mirror, and Josh saw his shiny new ringlets for the first time. He was shocked at how his hair looked even more girlish now, if that was even possible. His head was covered in the most childish sausage curls he could imagine. The springy curls bounced gaily with even the slightest movement of his head, and his large velvet hairbow was perched so effeminately on top. He was momentarily entranced by his incredibly sissyish ringlet curls as he watched them dangle. The darling corkscrew locks felt noticeably heavier on his head with all the hairspray Miss Andrea had used on them.
“What do you think, sweetheart?” Miss Andrea asked him, breaking the spell.
By now Josh knew well the type of response that was required as he saw his mother’s expectant look. “I just love my… princess curls!” he said with as much cheer as he could. “Thank you Miss Andrea… they are so… bouncy!” he added softly.
“You’re quite welcome, honey,” she replied kindly. Removing his pink nylon cape, she said, “now I want to see how they pair with your pretty suit.”
“Stand up dear, so we can see the whole look,” Mrs. Smyth instructed her charge. Josh stood back up, and Mrs. Smyth guided him back to face the full-length mirror. “I’d say we’ve found our own Little Lord Fauntleroy! Look!” she said cheerfully. Almost to herself, she added, “Gorgeous… simply gorgeous!”
“Joshy, aren’t you just the cutest Little Lord Fauntleroy… very fetching!” his mother exclaimed happily, “I’m so eager to take you and Kathy to the High Tea!” She added, “Your outfit is just perfect, and your princess ringlets are to die for!”
“Oh Josh,” Miss Andrea exclaimed as felt his jacket sleeve, “your velvet suit is simply delightful!” She added, “I just love your lace collar!” She marveled, “I can’t believe how well it fits you!”
Mrs. Smyth couldn’t resist adding with a knowing smile, “he got a little help from his corset.”
Josh cringed as he confronted his completed “boyish” outfit. For the first time, he saw the whole thing. Reluctantly, he studied the completely sissified boy staring back at him from the mirror. His heart sped up again as the full impact of the humiliating and confining outfit hit him. He was already growing warm from the fancy velvet suit, and he felt sweat forming in the small of his back underneath his satin corset. He was very conscious of the way his movements were now restricted by the multiple layers of prissy clothing which were extravagantly fastened, buttoned, laced, pinned, tied and buckled all over him. His cheeks warmed more as he blushed furiously.
He couldn’t resist the urge to reach up and touch his dainty new ringlets. He immediately noticed how stiff and “locked in” they were from all the hairspray. He gave one a little tug, and he watched as it sprang immediately back into place. “My princess curls,” he thought again as he saw how they practically gleamed in the light underneath his big pink hairbow.
His little man also began to press in its cage, but he knew it was hopelessly buried under his diaper, rhumba panties and shiny pink velvet knee pants. He looked nothing like a fifteen-year-old teenager… all he could see was an effeminate and delicate little sissy. Any traces of his dwindling masculinity had been shredded right before his eyes. The gleaming “SISSY” buttons on his finicky cutaway jacket twinkled gaily. The fussy pink ribbons and white lace frills around his wrists and knees were so cute and feminine. From his pink Mary Janes and ribbed stockings up to his flouncy silk blouse, he was totally trapped in the most sissyish outfit imaginable. And, of course, his enormous lace Fauntleroy collar seemed to taunt him mercilessly. Soon, he knew he would be on full display for all the people at the High Tea. It crushed him to know that this had all started with his own choices.
“Don’t you just adore your beautiful Fauntleroy outfit, honey?” His mother prodded him, “I’m sure you must be excited to show it off!”
With yet another a sigh of defeat, he answered, “Yes Mommy… it’s... it’s darling.” Then he added almost automatically, “I can’t wait to wear it for the Tea.”
“Excellent!” Mrs. Smyth added, “I’m sure your sister is dressed by now, let’s get her back here so we can see your outfits together!”
“And then,” his mother said with growing enthusiasm, “it will be time to leave!” Quickly she added, “And we’ll be sure to get plenty of photos for Mrs. Meriweather and your aunt!” In her mind, she repeated her mantra, “No half measures!”
The exquisitely attired teenager in the mirror let out another small sigh.
“Such an elegant little gentleman!” Mrs. Smyth said proudly.
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Hi Sissiboy,
I haven't commented on Joshy's story since you have started writing after your break. The reason being is that I like to read larger parts so waiting for quite a few to be posted then read in one go I find more thrilling. It makes Joshy's humiliation all the more exciting.
Just because I haven't commented doesn't mean I'm not interested as that is far from the truth.
Please continue.
Hugs
Dancer4Fun
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PART 57
In short order, they left the dressing area and returned to the main area of the dress store where Kathy was waiting. She immediately squealed with delight when she saw her brother, “Oooh Josh you are so cute! They’ve turned you into Little Lord Fauntleroy for sure… OMG your curls are ridiculously adorable… I love them!”
“Uhh thank you Kathy,” he said shyly, “They’re called ringlets, and Miss Andrea did them for me.” Instantly, he wondered why he had said all that, but he saw all the ladies beaming when he did.
“And look, we’re twins!” she went on. Kathy did a happy little twirl to show off her matching dress. It was true that her dress was made of the same rose-pink velvet with similar satin and lace trim, but it seemed to Josh that her outfit was much more understated than his. It was closer to something a modern teenage girl might wear to a fancy party. The lace accents of her dress were less intricate. Her shoes were made of similar velvet material as his Mary Janes, but they had no bows on them and had pointed toes. He was also somewhat surprised to see her shoes had heels. She was already slightly taller than her brother, but how she practically towered over him in his little pink ballet flats.
“Your outfit is so beautiful too, Sis,” he said as cheerfully as possible.
Seeing the two of them together, Mrs. Smyth commented, “you must remember that Ellen Meriweather was three years older than Cindy, so that’s why Kathy’s dress is slightly more ‘grown up’ if you will.” She explained further, “you can clearly see it has the same Victorian influences, but it’s a more mature take and was meant for a teenager as opposed to a younger girl.”
Gwendolyn insisted on snapping some photos of the two of them in their coordinated outfits, and it was clear to Josh that he looked every bit like the younger sibling next to his sister. It pained him as Mrs. Smyth reminded him again that he was wearing the outfit made for the younger girl. With a start, he realized he was actually jealous of Kathy’s dress! What was happening to him? While they were taking photos, Kathy grabbed his hand and coaxed him into doing a couple of curtsies in tandem with her. At first, he had suggested that he should bow instead of curtsy since he was in a “boy’s” outfit, but Kathy had immediately rejected that idea.
“Oh no, Joshy,” she said assertively, “you need to keep working on your curtsies, don’t you think?”
Josh had sheepishly given in immediately and said, “I guess you’re right, sis.”
Gwendolyn’s heart swelled as she watched her sissified son in his lovely pink Fauntleroy suit doing curtsies with his sister. He was certainly improving with practice.
A few moments later, Gwendolyn thanked Mrs. Smyth, “Well thank you so much for everything Dolores! I’m incredibly appreciative of all your help.”
Unprompted, Kathy piped in enthusiastically as well, “Oh yes thank you Mrs. Smyth! I feel so pretty and I love my dress!” and she dropped into another pleasing curtsy. Clearly enthralled, she added, “and Josh’s outfit is just darling!”
There was a slight pause as everyone turned to Josh expectantly. After a brief hesitation, the sissified boy spoke up as well, “Oh yes thank you for everything Mrs. Smyth!” he said with as much enthusiasm as he could muster. His mother then subtly cleared her throat, obviously wanting him to say more.
His cheeks warming again, Josh added, “I just adore my Little Lord Fauntleroy suit, Mrs. Smyth! I feel so… dapper wearing it! It’s perfect!” Next, he turned to Miss Andrea, and said, “And my curls are wonderful, Miss Andrea! Thank you so much!” Then, with an inward grimace, the teenaged sissy curtsied adorably for the ladies.
Mrs. Smyth beamed with satisfaction and replied, “You are all quite welcome! The two of you are just precious and I’m sure you’ll be a hit at High Tea!” Then she said, “I hope you enjoyed learning all about your Fauntleroy suit, dear… now you can truly appreciate that you’re wearing a wonderful bit of history!” Lastly, she added, “I know Mrs. Meriweather will be so pleased when she sees the photos of you in those darling outfits!”
“We’ll see you at the Tea, ladies,” Gwendolyn said, “Let’s go kids!”
As the three of them stepped out of the shop, Josh was immediately aware that they had attracted the attention of a few passersby checking out their extravagant outfits—especially his! The sissified teen tried his best to ignore the gawking stares as he steeled himself for a long afternoon. His pink velvet suit shimmered delightfully in the bright afternoon sunshine as he followed his mother and sister to the car.
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I can tell Josh feels so pretty. He might not even want to take his outfit off