New Arrangements for Josh

[sissyboy1212]

Thank you very much BabyJay.  That's supposed to be Josh's sister Kathy. Not exactly how I envision her appearance, but the image turned out cutely I think.

Decided to add another part.

[sissyboy1212]

PART 70

       In that moment, as the room grew quiet, Josh suddenly realized he would need to use the restroom soon. The urge descended on him with surprising speed. The fragrant tea he had been sipping all afternoon was making its presence known. He shifted discreetly in his chair, the frilly layers of his panties and stockings rustling against the crisp, soft velvet of his Fauntleroy suit. Every movement made the lace at his collar and cuffs brush delicately against his skin as a constant reminder of how elaborately he had been dressed. 

       Josh glanced toward his mother, hoping she might understand his predicament without drawing a lot of attention. He tried to mouth his request, “I need to tinkle,” but before he could finish, his mother pressed a finger to her lips to shush him and gave him a gentle but firm look. She clearly wanted him to remain poised, especially as Mrs. Standish stood and began to speak.

       Mrs. Standish announced, “Attention everyone, it’s time to give out some prizes!” As her voice rang through the lively tearoom, the clatter of conversation gradually faded, drawing everyone’s attention to her cheerful presence at the front.

       Josh tried to compose himself and shifted in his seat, hoping to ease his discomfort. His stockings whispered against each other as he nervously crossed and uncrossed his ankles. The urge to go had seemed to emerge from nowhere. He hoped against hope that at least for a moment the attention would shift away from him, and above all that these awards would be handed out quickly. The room brimmed with curiosity. Josh, however, felt a dual sense of dread about the pressure in his bladder and also about what these prizes might entail. He squirmed in his seat again.

       Mrs. Smyth, ever the watchful matron, leaned over and quietly whispered a gentle admonition, “Sit up straight, dear, and remember to be ladylike.” Josh felt his cheeks flush as he quickly adjusted his posture, trying not to fidget as much, though the urge to move was nearly overwhelming. 

       Mrs. Standish continued, “Before we begin our prizes, I want to give a special thanks to all our wonderful sponsors who made today possible. Special thanks go to Mrs. Dolores Smyth for her generosity and creativity, and to Andrea for her tireless help in organizing and decorating. Without you, none of this would have been nearly so delightful!”

       The room responded with a round of applause, warm and genuine, as the two women exchanged smiles and a subtle nod of pride. The applause seemed endless to Josh, who tapped his dainty slipper anxiously under the table, silently willing the proceedings to press on.

       Mrs. Standish then began to read from her list, starting with a prize that brought a ripple of adoring coos: “For our youngest guest in attendance, we have a very special prize!” A mother in a pastel dress gently lifted her toddler daughter, who wore a frilly, rose-colored party dress. The little girl was the very picture of sweetness in her party dress, delicate lace-trimmed socks, and shiny white patent shoes. The little girl blinked shyly as she was guided to the front, and Mrs. Standish knelt to present a small toy—an adorable stuffed bunny with satin ears and a bow. The audience “awwed” as the toddler hugged the bunny tight, her mother beaming with pride and gratitude.

       Mrs. Standish next handed out a series of charming door prizes. It turned out that each seat had a number taped under it, and Mrs. Standish called out the winning numbers one by one. Several ladies were delighted to win floral-patterned decorative teacups. An older gentleman and a college-aged girl both won ribbon-tied boxes of gourmet tea blends. Every prize was presented with a flourish and a kind word from Mrs. Standish.

       Next, Justin was mortified when his number was called to be among the winners for a small bag of chocolates prettily tied up in pink tulle favor bags with darling pink ribbons. His mother smiled and firmly took his hand to lead him up to Mrs. Standish, her eyes sparkling with satisfaction. The voluminous bustle of his confining dress made every step a production as he minced forward in his heels. He took small, dainty steps as the constricting folds of satin and tulle swished with each stride. The ladies in the crowd especially watched with delight, their faces lighting with knowing smiles and suppressed giggles. The handful of titters made Justin’s cheeks flush, and the unmistakably girlish sway of his walk drew everyone’s attention. His mother’s grip was unyielding as she guiding him to the front where Mrs. Standish waited with his prize. Surrounded by admiring glances and playful giggles, Justin meekly accepted the daintily wrapped sachet of chocolates.

       Then his mother leaned in, her voice unmistakably coaxing. “Now, what do we say, sweetheart?” she prompted, patting his shoulder softly.

       Justin turned beet red, glancing at Mrs. Standish as he spoke in a cowed voice, “Thank you, Mrs. Standish.”

       But his mother wasn’t satisfied with that and continued to nudge him gently, “Oh you can say more than that can’t you dear?” 

       The ladies in the crowd watched with delighted anticipation as Justin squirmed, clutching the pink tulle bag of chocolates. In a slightly louder and nervous voice, he tried again, “Th-thank you very much, Mrs. Standish, for the pretty chocolates.” His voice cracked, and a few guests giggled behind their hands.

       Mrs. Standish smiled warmly and replied, “You’re most welcome, Justin.” Turning to the crowd, she added sweetly “Isn’t he just precious?”

       Justin felt a hundred eyes on him and shuffled his feet nervously while his mother beamed. She gave him a gentle squeeze and began leading him back to his seat.

       Josh watched all this glumly as Justin returned to his table. A wave of secondhand embarrassment washed over him as he knew all too well how mortified Justin must have felt. He felt a sense of resignation as he feared his own moment was inevitably coming to be paraded in front of everyone. His spirits sank further as the prizes dragged on, and the omnipresent pressure under the confining layers of his adorable Fauntleroy suit steadily grew. It was increasingly difficult to focus on anything but his own discomfort and nagging dread. Just then, he also felt a different kind of unwanted tingle in his little cage. Josh let out a soft sigh and fought the impulse to squirm again. His cheeks warmed as he pressed his knees together, praying that the festivities would hurry along. 

[RibbonBound]

I check occasionally to see if there's any new chapters of this amazing story.  Imagine how delighted to not only find a new chapter but some actual pictures of Josh!  Thank you so much for the double gift!

[sissyboy1212]

Thank you RibbonBound! I've enjoyed playing with the AI images. (I have to credit Simonssister's excellent work for making me try some of my own.)

This is one that shows the scene in Mrs. Smyth's dress shop where Josh sees himself fully dressed in his Fauntleroy suit for the first time. He was so lucky to get the boy's outfit he was eager for!  :)

[sissyboy1212]

PART 71

       After all the door prizes were awarded, Mrs. Standish moved to the final prizes: Best Outfits. Josh cringed when he heard the word “outfit” as he had a sinking feeling of where this all was headed. The mere mention of “outfits” reminded him of how trapped he felt in his painfully ornate Fauntleroy suit. The constricting layers of velvet, lace, and ruffles felt heavier with each passing moment, and every button and ribbon seemed to reinforce his plight. His dainty pink velvet Mary Janes, just barely large enough for his prettily stockinged feet, pinched his toes with each anxious flex.

       With all the smothering attention he had gotten during the High Tea, it now seemed almost inevitable that he would get called forward. He was unable to ignore the expectant smiles and looks several of the ladies were casting his way, as if they all knew his turn was coming. By now, he was pressing his legs together tightly and trying to think of anything except the urge to go. With the elaborate way he had been buttoned, buckled, corseted, laced, fastened and tied into his Fauntleroy suit, he knew he would never get out of it without help even if he made it to the bathroom.

       A few moments earlier, Josh had finally whispered to his mother, “Mommy, I need to tinkle,” cringing as he said the childish words.

       She had whispered back that they couldn’t just get up and leave in the middle of the awards, and he would need to hold it a bit longer. “Besides, that’s why we took those… precautions, sweetheart,” she said quietly, alluding to the girls diaper he now wore under his rhumba panties, “we don’t want to miss it if you win something!” Her tone was sympathetic but firm. There would be no ducking out during the awarding of prizes. It began to sink in that he actually might have to resort to his diaper. At the time, the idea had seemed ridiculous to him. He was fifteen years old!  But now… it seemed like a real possibility. The thought made him shudder slightly.

       Meanwhile, the next prize went to an older lady at the next table who won the prize for “Most Festive Accessory.” Mrs. Standish presented her a pretty crystal brooch for her vintage hat with faux roses that had been admired by several in the crowd. The hat itself was a charming spectacle; it was wide-brimmed and trimmed with a spray of pastel silk blossoms. While the rest of the room smiled and clapped, Josh glumly watched her accept her prize. He was unable to stop his mind from drifting back to his own increasingly urgent predicament.

       Mrs. Standish’s eyes twinkled mischievously again. “Now, for Best Outfit Runner-Up, let’s welcome Justin back up!”

       Josh watched in sympathetic misery as once again, Justin was escorted back up by his mother to receive his prize. Samantha, ever the cheerful companion, tagged along gaily this time, her lively demeanor contrasting sharply with Justin’s hesitant steps. Mrs. Standish’s eyes gleamed with playful delight as everyone again turned their full attention to the sissified boy as he stepped awkwardly to the front of the tearoom and stood meekly next to her. His cheeks flamed as she spoke. Mrs. Standish said sweetly, “let’s take a moment to admire Justin’s gorgeous outfit! Such exceptional vintage style truly deserves this recognition.” She turned to Mrs. Smyth and said, “Dolores, would you mind telling us about his dress?”

       Justin shifted uncomfortably as Mrs. Smyth eagerly got up. She began in a somewhat teasing yet affectionate tone, “First of all, let’s congratulate Justin for being so daring to embrace such a pretty outfit as a boy.” Of course, she knew full well that this was not Justin’s choice at all, but it seemed more gentle in her mind to let everyone think he chose to dress this way. She led the crowd in another short round of applause. Samantha snickered at the idea that Justin wanted to wear a dress, and Justin looked like he just wanted to sink into the floor. The blush crept up his neck as Mrs. Smyth began describing his outfit. 

       â€śAs you can see, it’s a truly delightful Victorian party dress. Look how shimmery it is with those layers of organza!” she added. “And isn’t that pinafore just the sweetest thing you’ve ever seen?” she asked rhetorically. The crowd murmured their approval, some stifling giggles, others smiling in amusement at the fanciful details. Justin’s hands twisted nervously in front of him, his whole body radiating discomfort. The moment stretched on, with Justin forced to stand as the details of his elaborate, feminine attire were discussed at length.

       By now, Josh was increasingly restless in his chair. He spread his legs apart and wiggled them anxiously. He pressed his palms down flat on his thighs, and he was very aware of the sensation of his velvet pants rubbing against his stockings underneath. Thoroughly encased in his sissified suit, he felt his corset pressing unrelentingly into his waist and forcing him to maintain an upright posture. Most of all, Josh felt the constant dull ache in his abdomen. He tried to focus on the spectacle before him to distract himself, but it was almost as uncomfortable having to watch Justin’s sissified humiliation as it was to think about his aching bladder. As if that weren’t enough stress, his little man was starting to become nervous and excited again in his confining pink plastic prison.

       His mother took note of all of Josh’s anxious fretting and put her hand deliberately on his shoulder, silently reminding to be still with a disapproving look. He froze in place under the weight of her unspoken expectations. She then whispered one now-familiar word: “Knees!” That word had rapidly become a trigger for the discomfited sissy. That single syllable was a recurring reminder of the restriction imposed by his new reality. Reflexively, Josh rapidly pressed his knees back together as his cheeks reddened even more. He was chagrined to be reminded how each movement he made was so closely monitored, and he was acutely aware that even the slightest slip would be met with a corrective glance or gesture from his mother or the other ladies at the table.