New Arrangements for Josh

[Andlat]

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.

[babycakes]

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.

[sissyboy1212]

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.   

[sissyboy1212]

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.

[Sissy Little Girl]

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.

[nappy1]

I can’t wait until the pull-ups are introduced, perfect with a romper.

[sissyboy1212]

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.