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Author Topic: New Arrangements for Josh  (Read 180962 times)

rayd4107, Norm43, sissybaby34, scollymore08, derry, Andlat (+ 1 Hidden) and 59 Guests are viewing this topic.

Dancer4Fun

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Re: New Arrangements for Josh
« Reply #238 on: September 10, 2025, 07:39:30 PM »
Hi sissyboy,

I have just finished re reading Josh for the umteenth time.

I hope there is some way you can find a suitable conclusion to this wonderful story.

I'm hoping Josh is so traumatized by his High Tea experience he willingly becomes another daughter and little sister as a more modern but younger girly even asking mummy if he can take the tablets she suggested, so he grows little boobies to fill his training bras so he never again has to experience the humiliation of the Fauntleroy Suit again.


sissyboy1212

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Re: New Arrangements for Josh
« Reply #239 on: October 05, 2025, 01:20:28 PM »
Life has been very busy, but I'm going to try and continue Josh's story a bit more. Thanks for the nice comments.


sissyboy1212

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Re: New Arrangements for Josh
« Reply #240 on: October 05, 2025, 01:30:00 PM »
PART 59

   Nervously, Josh followed his mother and sister into the dining area which was buzzing with conversation. It appeared that most of the guests were already here, and many heads turned to see the new arrivals. Glancing around skittishly, Josh could see that most of the guests were dressed in some approximation of old-timey clothing. The crowd seemed to be mostly women and girls, although there were a few bored looking older men who looked to be with their wives. There were two young couples who appeared to be in their twenties sharing a table in the corner. There were also a decent number of younger boys and girls ranging from toddlers to about grade school age, but Josh didn’t see any boys around his age.

   As Josh felt their eyes on him, there was a noticeable quieting of the buzz. His cheeks were practically on fire as he felt the attention of the room shift to his over-the-top sissyish appearance.

   â€œOh there you are,” Josh heard a familiar voice break the silence as Mrs. Smyth greeted them, “I’m so glad you made it!” Then, turning to another older lady in a Victorian dress she added, “Gladys, let me introduce you to the Hartleys. These are the ones I was telling you about.”

   Turning to Gwendolyn, Mrs. Smyth made introductions as the murmur of conversation slowly resumed, “Mrs. Standish runs the place and she is our host for Tea today.”

   Josh’s mother smiled and offered her hand, “I’m Gwendolyn. Turning to her children, she continued, “This is Kathy.”

   Of course Kathy piped right up and said, “Hi Mrs. Standish
 everyone looks great!”

   Mrs. Standish graciously replied, “Thank you dear, I’m so pleased to have you. That’s a beautiful dress.” It was obvious that Mrs. Standish was keenly interested in the elaborate outfits Kathy and Josh were wearing, but it was also clear that Josh’s ultra-sissyish appearance was now the focus of her attention. Without waiting for Gwendolyn to continue, Mrs. Standish turned her gaze to Josh and said, “and this handsome little fellow must be Josh!”

   Josh cringed even more. He knew he should say something, and stammered, “Ni
 nice to meet you Mrs. Standish.”

   Gwendolyn cheerfully piped in and said, “Yes he’s my oldest.”

   â€œYour oldest, you say?” Mrs. Standish said in surprise, “I never would have guessed that.” She continued gaily, “but Mrs. Smyth has told me all about you, dear, and you make an absolutely adorable Little Lord Fauntleroy!  I must say Andrea did a marvelous job on your ringlets
 just lovely!”

   Turning back to Gwendolyn, she added, “He looks so fetching in Cindy Meriweather’s old outfit
 It fits him like a glove!” She concluded, “I’m so glad to have you with us today.  We’re all going to have a splendid time!”

   Mrs. Smyth beamed and said, “Well I know you are busy so we’ll find our seats. Thank you for seating us right up front.”

   â€œBusy is not the word for it!” Mrs. Standish exclaimed, “High Tea today and the wedding on Saturday! I never should have tried to do all this in the same week!” She giggled a little, “but I always love a little busy chaos!” she added as she walked away from them energetically.

   â€œOh that’s right,” Mrs. Smyth remembered, “Gladys’ daughter is getting married on Saturday.  That’s her over in the corner with her fiancĂ©.”  Mrs. Smyth waved to the young couples at the table in the corner, and one of the young women waved back at her. “Gladys has been working nonstop to make sure it’s a picture perfect ceremony!” 

   Next, Mrs. Smyth led them to their table. As Mrs. Smyth practically ushered the emasculated teen to his seat, Josh realized they would be seated with Mrs. Smyth and Miss Andrea right in the center of the room. He sighed with resignation as he realized he would be on full display. He felt his little man fruitlessly straining in its pink plastic prison, but Josh knew there was no escaping the confining layers of his foppish Fauntleroy outfit. 

   As the sissified boy sat down on the padded seat cushion at the overly fussy little table, he felt the added fullness of his pullup diaper under his gorgeously juvenile velvet knickers. His delicate nylon stockings felt so silky on his slender legs, and his lacy collar fluttered ever so gaily as he placed his embroidered napkin on his lap.

   Gwendolyn smiled with satisfaction to see her thoroughly feminized son in his “boyish” outfit sitting so daintily as they prepared for tea. She now understood how those domineering mothers of old must have felt as they competed to see which of their sons would have the most elaborately decked out Fauntleroy suit! She admired again how girlishly his springy “princess curls” cascaded prettily down above his ornate Fauntleroy collar. His floppy pink hairbow just made the sight all the more darling! “No half measures!” she thought again to herself.

   As the same waitress who took care of them at brunch a few days ago approached to serve their tea, Gwendolyn sniffed slightly and chided her son in a stern whisper, “Knees, Joshy
 I have my compact in my purse if we need it!”

   The mortified teen immediately jerked his knees together, and that just made him even more aware of the bulky diaper he wore under his rhumba panties. His little man tingled helplessly again. Josh gave his mother a weak smile and croaked, “Yes Mommy.”

   Kathy giggled softly, and the pretty young waitress arched her eyebrow as she served their tea. It was obvious she had noticed this exchange.

   Already on pins and needles, Josh sat glumly while his tummy fluttered furiously yet again.

sissyboy1212

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Re: New Arrangements for Josh
« Reply #241 on: October 07, 2025, 08:03:19 PM »
PART 60

      Josh glanced again at his mother, and she nodded approvingly. Clearly, she was pleased with how things were unfolding. The realization made Josh's cheeks grow even warmer. The delicate clinking of china and soft chatter of conversation from nearby tables just reminded him how out of place he felt. It was obvious that his Fauntleroy outfit was much more elaborate than what anyone else was wearing. That just amplified his discomfort. Every time he dared to look around, he saw curious eyes turning to him. 

      Some people were discreet about it, but many of the ladies and girls were openly staring at his overly frilly outfit. Every detail of his attire screamed “Sissy!” He tried to focus on the fancy table setting, examining the delicate patterns of the teacups to distract himself as he wondered how he would ever get through this.

      Their waitress began filling their teacups with a cheery attitude. The nametag pinned on her blouse said “Jenna,” and she smiled at Josh in recognition. “I remember you!” she exclaimed as she poured Josh a steaming cup. She continued, “You were in here on Sunday for brunch, but I would never have guessed you were a boy when I first saw you!” With a knowing grin, she added, “But boys should be able to enjoy pretty things too, right?” Her gaze lingered on him. “And what an absolutely precious outfit
 I bet you feel like a little doll in that! You sure look like one!”

      Josh blushed deeply, feeling flustered by the new attention. Her words struck a chord, highlighting feelings he had struggled with all week. He did feel like a helpless doll, swept up in a whirlwind of girlish and sissified outfits. Dresses, panties, ribbons, and lace had rapidly become his everyday reality, plunging him into an inescapably feminine new world. Josh managed to stammer out a response, “Uh thank you
 umm
 I just LOVE my Fauntleroy suit!” Frustration swept over him—he couldn’t believe how he had gushed that way. He still was unable to contain his nerves. Without thinking, he fiddled again with his daintily embroidered napkin which only drew focus back to his hands. His glossy pink nails sparkled prettily, perfectly complemented by the fussy lace cuffs and cute ribbon ties encircling his wrists.

      “Oh, and sweetie I just love your nails,” Jenna continued admiringly, “so cute!” She leaned in with a mischievous smile and lowered her voice just a bit, “it's not every day we see such a darling little doll like you in here!” Seeing Josh’s discomfort grow, she softened and said kindly, “Just so you know, you’re definitely one of the cutest guests I’ve ever waited on.” Then, as if to change the subject, she continued “that polish suits you
 what color is it?”

      Cringing, Josh replied softly, “oh thank you, it’s uh
 ‘Baby Pink Sparkle.’” Once again, he felt the full weight of his completely sissified and emasculated state. Despite himself, he added, “Kathy helped me pick it out
 we got the same color.” Josh flushed more deeply as his mind drifted back to the manicure and pedicure in Miss Andrea’s salon. He recalled how unsettled he had felt as Denise, the cheerful nail technician, had worked on him with practiced ease. Every brushstroke of polish had seemed to strip away another layer of his boyishness. That had been such an intense day! After his first perm, manicure and pedicure, his descent into girlishness had begun to feel inescapable. Now, sitting at this table in his fussy velvet suit, all those feelings rushed back.

      Kathy grinned and flashed her pretty pink nails as well and added, “That’s right! Josh and I wanted to match!”

      “Well, it looks just precious on you both,” the waitress complimented them again as Josh wanted to sink out of sight.

      Josh’s nerves were truly on edge now. Each flutter of lace and whisper of silk against his skin only heightened his skittishness. Sitting daintily on display, he fruitlessly longed for the life he had lived just a week ago
 before he had been so thoroughly sissified. It pained him to remember that this was the path he had chosen! He could have gone to Sterncourt, but instead he was enveloped in these suffocating layers of frills and lace. Last week felt like a distant memory now, and he realized how he had taken for granted the freedom to move unnoticed and dress however he pleased. Now, that all felt impossibly distant.

      As Josh tried in vain to settle his emotions, Mrs. Smyth suddenly leaned to him with a nostalgic smile. “You know, dear,” she said with twinkling eyes, “seeing you in that darling Fauntleroy suit brings back memories of Cindy Meriweather years ago.” Josh grimaced, but Mrs. Smyth went on, “Cindy was the picture of sweetness—her curls, her bows, even those dainty velvet ballet flats you are wearing right now. I swear, Josh, you could be her twin. I have the cutest photos of Cindy all dolled up in that very suit. We simply must get some pictures of you today to share with her!” 

      “That’s a wonderful idea, Dolores!” Josh’s mother exclaimed in agreement.

      As Josh continued to stew, Mrs. Smyth patted his shoulder reassuringly. “Don’t be shy, my dear. You look absolutely exquisite!” She said it loudly enough that even some of the guests at the next table seemed to hear.

      Josh sighed softly again.

Andlat

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Re: New Arrangements for Josh
« Reply #242 on: October 08, 2025, 01:09:37 AM »
Yes, Josh did choose this, but he clearly didn't comprehend the full gravity of his choice. Oh, well. Too late now!

sissyboy1212

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Re: New Arrangements for Josh
« Reply #243 on: October 08, 2025, 06:43:32 PM »
PART 61

       Everyone was soon enjoying their tea and an array of fussy snacks, teacakes and finger sandwiches. Josh had to admit the tea was good as long as he added sugar to it. He picked daintily at all the little sandwiches which his mother insisted he eat with his utensils. It was slow going, and his gleaming nails flashed ostentatiously every time he used his fork and knife or delicately picked up his teacup. Jenna was very attentive and made sure all their teacups stayed refilled. Josh was also constantly mindful of the elaborate ruffles on his silk blouse that cascaded so elegantly down his chest. His entire outfit was practically smothered in billowy ruffles, darling ribbons, and of course plenty of gorgeously embroidered lace!

       Every time Josh turned his head, his glossy ringlets danced gaily around his face and neck. The springy curls seemed to have a life of their own and reacted with each slight movement, framing his features with playful motion. His huge lace Fauntleroy collar seemed to draw stares like a beacon. As he sat, he also couldn’t ignore the tickling sensation of his clingy stockings as they continuously rubbed against the fabric seat cushion. Every time he shifted in his seat, little friction tingles shot up his thighs. Constantly on display, Josh glumly continued to sip at his tea. He longed to escape the attention and the fuss. It all made him feel so exposed. Even lifting his teacup felt like a theatrical display! Josh couldn’t help but reflect again on his predicament
 the one he had chosen! He knew he looked nothing like a fifteen-year-old boy at this point. Instead, he had become a dainty little sissy. His flouncy frills, pristine lace, and adorably curled hair left no hint of the teenage boy buried underneath.

       There were brief moments when Josh almost managed to forget his surroundings, but he would then be pulled right back to reality. Several other guests found excuses to swing by their table for a closer look at his elaborate outfit. Ladies he didn’t know leaned over to gush about his extravagant collar and charming corkscrew curls. Young girls half his age giggled at his sissified appearance. One younger boy asked him in bewilderment why he wanted to dress that way. Even a few of the men glanced his way with pained amusement. Josh felt his masculinity evaporating with every polite nod and weak smile.

       The fussing over the persnickety details of his appearance seemed endless. Every aspect of his Fauntleroy look—from the velvet hairbow perched atop his stiff princess curls to the beautifully embroidered collar framing his face—seemed designed to draw maximum attention. The more guests commented on how “darling” and “precious” he looked, the more acute his embarrassment grew.

       On the other hand, Mrs. Smyth relished the opportunity to lovingly describe his Fauntleroy suit to anyone who would listen, which only reinforced the sense that he was a precious little doll on display.  Several times, she coaxed him into standing up to show off his “sassy” satin sash so his admirers could appreciate the entire ensemble. Underneath his panties and diaper, his little man continually writhed in its pink prison.

       His mother also seemed positively delighted by the extra attention. At several points, she reminded him with gentle insistence, “Remember, Joshy—Knees!  Keep them together nicely. That’s what proper little Fauntleroys do!” If he failed to show the right appreciation after a compliment, she would quietly remind him of his manners. “Say thank you, dear,” she chided him, “Be a good little gentleman.”

       â€œYes, Mommy,” he replied meekly again and again. For Josh, the High Tea dragged along at a snail’s pace.

sissyboy1212

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Re: New Arrangements for Josh
« Reply #244 on: Yesterday at 07:24:33 PM »
PART 62

      Shortly after the Tea had begun, one visitor to their table stood out memorably. Off to the side, Josh heard a small commotion as a woman led her young daughter over to their table. They appeared to be late arrivals for the Tea. Josh turned in his seat, and his eyes widened in disbelief when he realized that the “daughter” was, in fact, Justin—the bratty boy they had encountered at Sunday brunch!

      The blushing boy was now fancily dressed in a lavish Victorian party dress, and he was obviously unhappy about it. His eyes were rimmed red, hinting at tears that had recently been shed. His sumptuous frock was crafted from shimmery navy-blue satin, with cloudlike layers of sheer organza floating over the full skirt, each edge trimmed with intricate ivory lace and dainty pearl beading. The high, rounded neckline was adorned with a prominent Peter Pan collar, trimmed in delicate lace and embroidery. Short, puffed sleeves ballooned over the boy’s shoulders before ending in tight ruffled cuffs tied with oversized bows.

      Over his prissy dress, Justin wore a starched white pinafore with scalloped hems and layers of gathered lace, adding an extra touch of delightful sweetness. His skirt flared out dramatically from the layers of a stiff crinoline petticoat, which created a classic bell silhouette.

      Snow-white tights adorned with subtle floral embroidery encased his legs. A pair of shiny black Mary Janes—each topped with a fussy bow—were buckled snugly on his feet. Justin’s childishly girlish shoes would have made any Victorian girl feel like a fairy princess. A charming vintage hairbow, made of the same navy satin and dainty lace, was perfectly arranged in his still boyishly short hair. Aside from his unmistakably boyish face and haircut, however, the petticoated adolescent looked every bit like a dainty little girl attending a fancy party in an older time.

      Justin’s posture was stiff, and he looked miserable. His cheeks were flushed a deep red as he was clearly mortified. What caught Josh’s attention even more was the unmistakable aura of control exerted by Justin’s mother. She guided him smartly to the table with a gentle but firm grip on his shoulder. His mother exchanged a knowing glance with Gwendolyn before speaking, “We are running a little late
 Justin here pitched quite the little tantrum as I was getting him dressed, but he eventually came around!” She shot a stern look at her petticoated son as she spoke, and Justin looked utterly cowed. He just stood there uneasily under the scrutinizing eye of his mother.

      Then, Justin's mother turned to Gwendolyn. “Forgive me, but I didn’t introduce myself properly on Sunday
 I’m Margaret. I just wanted to stop by your table when I saw you and thank you so much for your recommendations on improving Justin’s behavior,” she began warmly. She continued gratefully, “I think you gave me just the right words at just the right time!” Looking back at Justin, she continued, “He has been such a handful, but I think we’re finally making some real progress.” She went on, a little more confidently, “I assure you, he understands what’s expected of him now.” As she spoke, she gave Justin another determined look that made it clear she would tolerate no further outbursts.

      For a moment, Josh struggled to process his feelings. He was very embarrassed for Justin on the one hand, but he couldn’t deny he also felt a small sense of vindication as he watched Justin fidget fretfully in his ultra-girlish party dress. He knew exactly the humiliation Justin was feeling, but still, a tiny part of him appreciated the irony. Only days before, Justin had been the one making fun of Josh. Now, here he was, getting his own healthy dose of karma.

      Josh stared as Justin’s mother had him spin around so everyone could get a good look at his old-fashioned outfit. In doing so, she delicately smoothed his poofy skirt and slightly adjusted the enormous bow at Justin’s back, making sure every detail was perfect. Justin stood helplessly, his cheeks burning as he tried to avoid everyone’s eyes, especially Josh’s.

      Inevitably, the two boys locked gazes for a moment—two misbehaving boys now sharing a common plight: one buttoned securely into a gorgeously sissyish Fauntleroy suit, and the other trapped in an extravagant party dress from another time. The awkwardness between them was palpable.

      For her part, Gwendolyn was taken somewhat aback by the changes her little suggestions had inspired. It seemed she had awakened a sleeping giant. On Sunday, she had only seen a frazzled mother near the end of her rope—a sister traveler, perhaps. But today, it seemed that a light bulb had come on. She recovered quickly and said, “Well, congratulations on helping young Justin here as he turns over a new leaf!” Next, she flashed her new friend Margaret a beaming smile of solidarity and encouragement.


 

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