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Author Topic: New Arrangements for Josh  (Read 186544 times)

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sissyboy1212

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Re: New Arrangements for Josh
« Reply #252 on: October 16, 2025, 11:00:14 AM »
Thank you babycakes for your sweet encouragement.

In Josh's story, the High Tea was always planned to be a major event. It's part of why there was such a long break in my writing... I could never quite decide how I wanted it to unfold. But I've had some more ideas lately.

I'm working on the next part :)


sissyboy1212

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Re: New Arrangements for Josh
« Reply #253 on: October 20, 2025, 06:30:09 PM »
PART 65

   When Justin stumbled, Josh’s gaze was again drawn downward to Justin’s glossy, patent-leather Mary Janes. Somewhat regaining his composure, Josh belatedly realized that Justin’s shoes sported cute angular heels that were about an inch tall. He hadn’t noticed that at first. Unlike the ballet style flats Josh was wearing, Justin’s unfamiliar heels clearly required more grace and practice than Justin possessed. No wonder he looked so wobbly on his feet! Between Justin’s confining corset, the bulky bustle protruding from his backside and those fussy heels it must have taken great concentration just to keep his balance. He watched as Justin nervously fiddled with the delicately scalloped fringe of his dainty pinafore. Clearly, Justin was now worried about what Mrs. Smyth might have planned for him.

   As Miss Andrea, Mrs. Smyth and even Kathy chimed in with so many helpful suggestions, Margaret surveyed her son with a thoughtful gaze, almost as if she were seeing him clearly for the first time. She was plainly excited by all these new possibilities, and she had especially noted Justin’s pained expression when Mrs. Smyth had described Josh’s pretty underthings. She began to muse aloud to her son with growing energy and determination, “Oh sweetheart you have so many delightful changes to look forward to—pretty dresses, darling shoes, dainty nightgowns!”

   She turned to Kathy warmly, “and thank you for thoughtfully suggesting a manicure, that’s a great idea!”

   Kathy giggled, “Of course! Justin, I bet you’ll have the cutest nails of any of us! Won’t that be fun?”

   Justin’s mother nodded cheerfully and spoke to him again, “Honey, I’m sure you’ll feel so pampered and pretty with some pretty polished nails.” With a slightly firmer tone, she added, “Oh I promise you won’t have a single moment to get bored or misbehave anymore—we’ll plan all sorts of exciting things to occupy your time and energy!” Her words left no doubt about her intentions.

   Then, Margaret turned back to Gwendolyn and said, “Well we’ve taken enough of your time, but I just wanted to thank you again for your wonderful advice!” Then, in a lower voice, she again admonished her befrocked son. “Listen carefully, darling,” she began. She continued, “Don’t embarrass me today—no fidgeting, no sulking, and no complaining!” She flashed a final grateful smile at Gwendolyn. Without bothering to wait for a response, she began firmly guiding Justin to their own table to enjoy the High Tea.

   Helplessly swept along, Justin clutched in vain at the edges of his poofy skirt with each hesitating step. He looked absolutely stricken. The snug embrace of his overwrought dress—the corset’s firm squeeze, the flouncy petticoats, the cloud of ruffles and ribbons—forced him to scurry meekly with an effeminate, mincing gait. Every slight movement made his bouncy skirt swish dramatically. The confining layers of his precious outfit shortened his steps in a conspicuous way and drew extra attention to his predicament. He was cutely unsteady in his dainty but treacherous heels… teetering along like a bashful little girl playing dressup in her mother’s shoes! He cast a longing look back at Josh and the others as if silently pleading for rescue, but there was nothing to be done. The anxiety on his face—bordering on an adorable panic at this point—was impossible to miss. It was the unmistakable look of a boy newly plunged into a world of frills, ribbons and lace. As Samantha trailed merrily along behind her brother, her cheerful mood was a total contrast to Justin’s obvious chagrin.

   â€śWell,” Gwendolyn observed dryly, “that was quite interesting!” She had a trace of satisfaction in her voice as she exchanged a knowing look with Mrs. Smyth. Both ladies giggled slightly.


BabyJay

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Re: New Arrangements for Josh
« Reply #254 on: Yesterday at 04:57:12 AM »
Delightful. Josh must be horrified at Justin's treatment, but, even more worried about what His mother has in store for Him. Look forward to next chapters.

sissyboy1212

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Re: New Arrangements for Josh
« Reply #255 on: Yesterday at 07:49:43 PM »
PART 66

        Incredulous at this turn of events, Josh just gawked as he watched Justin’s mother shepherd him away. Worry crept into his own thoughts. His own mother seemed to be enjoying all this petticoating very much—perhaps even more than he’d realized up until now. Not for the first time this week, Josh suspected that his new journey in dresses was no longer just about him alone—it was, in some important ways, becoming a shared experience. The choice to start his journey into girlishness had certainly been his, but there was no question that his mother seemed delighted with his decision!

        The sissified teenager felt the unwelcome tingling in his rhumba panties again as they all sat back down to continue with High Tea. As if they had read Josh’s mind, Gwendolyn and the other ladies began to discuss the differences between Justin’s predicament and Josh’s situation. Sheepishly seated between his mother and Miss Andrea, Josh looked like the very picture of a storybook sissy boy in his immaculate Little Lord Fauntleroy suit, his curls bouncing gaily and his cheeks still sweetly tinged pink.

        Mrs. Smyth, ever observant, commented, “You know, you can put a child in the prettiest frock, but it’s clear Justin is still just a boy in a dress.” She added, “He’s like a grumpy baby with all that pouting and fidgeting. Unlike Josh here, the gentle spirit just isn’t in him yet.” Her words were a recognition that Justin’s transformation was something done to him, not something he had chosen. She then turned to Josh and addressed him in a sweet tone, “On the other hand, Josh dear, it does my heart good to see you sitting so nicely in your beautiful Fauntleroy outfit and behaving just as you should!” The other ladies offered murmurs of agreement, their smiles tinged with understanding.

        Miss Andrea concurred, “It’s true. It’s charming to see Josh here so adorably dolled up in his little suit for tea time, so polite and sweet!” As she spoke, she softly patted Josh’s hand with reassuring fondness as if he were a toddler. This only made the sissified teen’s cheeks flush pinker.  She continued, “As darling as he is, Justin’s just not ready to embrace his situation.”  Something seemed to catch her eye, and she giggled, “at least not yet anyway!” Then, pointing discreetly across the room, she said “Look at him over there.”

        All their eyes turned to a table on the other side of the room where Justin was perched primly upright on the absolute edge of his chair like a delicate caged canary. His fastidiously arranged bustle and petticoats occupied most of the chair seat behind him, and his lap was buried under a buoyant mass of rustling skirts, frills and satin. They all watched as he took a timid sip of tea under his mother’s watchful eye. While Samantha wore a huge grin, the look of misery on Justin’s face was obvious even from across the room. After another moment, Josh felt everyone’s attention return to him.

        Even Kathy giggled and got into the act. She spoke lovingly to him as though he were her little sister, “I’m so happy to have my sweet brother back again, Joshy!  And you are so cute in your suit with those springy curls and rosy cheeks!”
 
        Taking all this in, Gwendolyn settled her focus back on Josh. She spoke in a loving but resolute tone, “That’s right. My sweet Josh here is on a different path.” Then, with gentle encouragement, she continued, “Josh, what makes your journey so special is that you had the courage to choose the pretty things, the frills and the lace all by yourself.” Addressing her son directly, she added, “Once you were honest with yourself, you realized you were meant to be Mommy’s little angel! Isn’t that right sweetheart?” She paused for a moment, her eyes warm and tender as she waited for Josh’s response.

 

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