New Arrangements for Josh

[babycakes]

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?

[sissyboy1212]

Guilty!  Those are the inspiration.  I saw them online and knew they would be perfect for Joshy!   :P

[sissyboy1212]

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.

[Sissy Little Girl]

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

[sissyboy1212]

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.

[Sissy Little Girl]

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

[sissyboy1212]

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.