New Arrangements for Josh

[sissyboy1212]

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.

[Andlat]

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.

[sissyboy1212]

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.

 

[dolly bo peep]

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.

[sissyboy1212]

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.

[sissyboy1212]

PART 44
   
   Josh leapt out of bed just as his mother opened the bedroom door.

   â€śWe 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.

   â€śUhhh…” the red-faced boy stammered. “I… uhhh…” he began again.

   Comprehending now, Gwendolyn asked gently, “Did you have another little accident, sweetheart?”

   â€śYes 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.”

   â€śI 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.

   â€śJosh,” 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.

   â€śOh 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.

   â€śOK 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.

[Andlat]

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.