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Author Topic: New Arrangements for Josh  (Read 119085 times)

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dolly bo peep

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Re: New Arrangements for Josh
« Reply #168 on: December 09, 2021, 07:47:43 AM »
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.


sissyboy1212

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Re: New Arrangements for Josh
« Reply #169 on: December 28, 2021, 06:29:44 PM »
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.

   â€śMommy, 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.

   â€śDon’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---”      

   â€śYour 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.

   â€śAfter 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?”

   â€śThey 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?”

   â€śOh honey, does it hurt you?” she asked with genuine concern, “does it not fit correctly, dear?”

   â€śNo, 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.

   â€śWell 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?”

   â€śWell, 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.

   â€śRemember 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.“

   â€śSo 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.

   â€śOh 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.

   â€śOh… 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.

   â€śThat’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.


Party Dress

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Re: New Arrangements for Josh
« Reply #170 on: December 29, 2021, 03:04:01 PM »
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

sissy marci

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Re: New Arrangements for Josh
« Reply #171 on: December 31, 2021, 11:58:06 AM »
Lovely story, thank You. Love Marci

JanetMarie

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Re: New Arrangements for Josh
« Reply #172 on: December 31, 2021, 06:02:16 PM »
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

poppylongstocking

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Re: New Arrangements for Josh
« Reply #173 on: January 03, 2022, 05:04:32 PM »
Just wanted to thank you for this story. I really appreciate how you're taking your time with it.

dolly bo peep

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Re: New Arrangements for Josh
« Reply #174 on: January 06, 2022, 09:19:59 AM »
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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