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Author Topic: New Arrangements for Josh  (Read 119117 times)

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sissyboy1212

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Re: New Arrangements for Josh
« Reply #140 on: April 07, 2021, 07:04:30 PM »
I decided to go ahead and work on the next part.

-----

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.

   â€śThanks 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.

   â€śCareful 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 cafĂ© 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.

   â€śI especially love your curls, sweetie,” she said nicely to Josh. “They’re just adorable!”

   â€śThank 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.

   â€śKnees, 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.

   â€śGoodness 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.

   â€śNo 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.


Andlat

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Re: New Arrangements for Josh
« Reply #141 on: April 10, 2021, 01:26:13 PM »
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.


sissyboy1212

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Re: New Arrangements for Josh
« Reply #142 on: April 10, 2021, 09:20:16 PM »
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.

sissyboy1212

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Re: New Arrangements for Josh
« Reply #143 on: April 11, 2021, 10:57:29 AM »
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.

     â€śRemember 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.

     â€śI 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.

     â€śHow 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.

   â€śWhy 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!”

   â€śThat’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.

   â€śTh.. Th… thank you Mommy,” he said glumly as his little man tingled unexpectedly, adding to his feeling of unease. It just made everything worse.
   
   â€śTruthfully, 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.

   â€śTime 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.

dolly bo peep

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Re: New Arrangements for Josh
« Reply #144 on: April 23, 2021, 02:36:02 PM »
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.

sweet baby katie

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Re: New Arrangements for Josh
« Reply #145 on: April 30, 2021, 02:41:57 AM »
Wonderful!  Thank you for your sweet writing.

sissyboy1212

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Re: New Arrangements for Josh
« Reply #146 on: April 30, 2021, 08:30:09 PM »
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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