Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on Yesterday at 07:09:04 PM »
With Edward now fully dressed in the old vintage gown, Miss Vale and Mrs. Bell studied him closely. They had the old photograph of his great-great grandmother handy, and they looked repeatedly back and forth from the photo to Edward. After some quiet discussion between them, Miss Vale led Edward into the studio where he would pose. The real work was about to begin.
She sat him on a carved wooden chair beside a small table covered with fine white lace. She had staged the table with a slender vase of pale roses, a china dish painted with violets, and a tiny silver bell. The chair itself had a high back and curved wooden arms padded with faded rose silk. Behind it, Miss Vale had hung a length of cream damask so the background fell in soft folds, and a gilt oval mirror nearby caught the window light and returned it in a gentle glow. Perched daintily atop the chair, however, Edward discovered that it was somewhat narrow.
Belatedly, he was taken aback when he saw the size of Miss Valeâs blank canvas⌠it was huge! It looked to be nearly four feet tall and at least three wide.
âThatâs really big, isnât it Miss Vale?â he asked questioningly.
She smiled and said, âWell, yes itâs on the generous side I suppose, but your Aunt Patricia wanted me to capture all the fine details, so I suggested we go for a grander scale.â She added, âthatâs why we will need more sittings than normal⌠I expect twelve to fifteen sessions should do it.â
Edwardâs jaw dropped. He hadnât realized that he was signed up for all that. âTwelve to fifteen?â he repeated softly. He was chagrined to hear that he had that much time in dresses before him.
Aunt Patricia merely smiled in satisfaction. The look on her face made it clear that she thought it was wonderful.
Miss Vale and Mrs. Bell continued their preparations. As Mrs. Bell appraised her subject to see if any last touches were needed, she said to herself, âA little tighter on the left side, I think.â She explained, âin the photograph, that curl sits nearer the cheek.â
âNearer, yes, but not on the cheek,â Miss Vale added. âIf it hides the line of his face, I risk losing the resemblance.â
Mrs. Bell nodded, âthen we shall persuade it, not force it.â
Edward sat very still on the chair while they circled him. He found that it was easier not to speak, and he didnât trust his voice now anyway. The constant fussing over his appearance felt stifling.
Finally, Miss Vale began posing her subject. Edward soon learned she had an array of special supports and stays to ensure he held the correct pose. From a cardboard box she began to pull slender lengths of covered wire, padded at the ends with soft cloth, and various pale, smooth supports made of plastic. These invisible tools would help him keep his position. The process of placing them was almost as elaborate as the dressing itself. First Miss Vale made some chalk marks on the floor for the chair legs. Then, she had Edward sit, rise, and sit again until the skirt fell properly around the cushion. Mrs. Bell lifted the gauzy overskirt while Miss Vale referred to the old picture again.
One stiff support slid gently beneath the ruffle of Edwardâs right sleeve, guiding the angle of his elbow. Another lay hidden inside the left cuff so his arm would turn the right way. A narrow padded stay was slipped behind him, invisible against the high back of the chair and fastened discreetly so his shoulders rested just so without slumping or leaning too far forward. Miss Vale tested it with two fingers at his shoulder blade, then adjusted it by the smallest fraction. âThere,â she said. âJust to remind you where the portrait needs you.â
Then came his knees and legs. Miss Vale knelt before the chair with a measuring ribbon while Mrs. Bell lifted the layers of petticoat just enough to see the white tights and the line of his shins. Edwardâs knees were brought together, then eased apart a breath, then brought back until the fall of the skirt matched the photograph. Soft plastic rests were tucked beneath the overskirt at either side to keep the fabric from collapsing. Narrow ribbon stays were fastened from the chair frame to the hidden guides near his knees and ankles, firmly enough to ensure his legs would not wander out of the pose. Miss Vale placed each embroidered shoe on a chalk mark, turned the toes to a demure angle, and slipped tiny fasteners beneath the soles. After a moment, Edward realized she had tacked these down to the wooden floor to keep his feet from wandering.
Edward was keenly aware at this point that he was basically a life-sized doll to be posed, primped, fluffed and positioned. He felt pretty and delicate in the most humiliating way, a fragile and precious keepsake that Miss Vale and Mrs. Bell handled with doting care. The thought made his cheeks warm more.
Miss Vale stepped back, took a photo with her phone, and compared it to the old image of his great-great grandmother. Then, she frowned and returned to adjust his feet again. Every detail was assessed. By the time the velvet, lace, and gauzy overskirts were smoothed properly, no one looking at Edward would suspect all this hidden little engineering. That was almost the worst part. From the outside, he would look serene and willingly delicate while underneath he would feel all the little restraints and reminders that enforced his compliance.
âChin up a tad darling,â Miss Vale instructed, âand think of seeing something far off that interests you.â
Edward obeyed because there was very little else he could do. He thought of a large ship. Then he thought of a speeding car. Then, with a suppressed sigh, he thought of the playground outside, where the other children moved however they wished. Through the open window he heard a burst of laughter, bright and careless, followed by someone shouting happily. The sound struck him with almost physical force. Out there, boys his age were racing through damp grass and yelling to their heartâs content. In here, Edward sat wearing immaculate pink lipstick with his girlish ringlets arranged just so. He was cocooned in layers of lilac velvet, fluffy petticoats and a stiff corset while they played happily. The contrast made something twist painfully in his chest, and his nose began to itch.
With Edward finally arranged, Miss Vale snapped several more photographs with her phone: from the front, from the side, and several more close enough to show the position of his hands and the fall of his ringlets.
Edwardâs eyes widened as he wondered why she needed all those photos of him. âFor comparison,â she spoke as if reading his mind, âNext time, these will tell us whether your pose has wandered.â
âCan I breathe?â Edward asked tentatively.
âOf course you may breathe,â Miss Vale said, laughing softly. âOnly perhaps not as dramatically as you are accustomed to.â
âWell now,â she continued, âwe shall not try to make you look like a statue, but I will help you learn the art of feminine stillness.â The peculiar phrase settled over him like one more layer of lace. âFeminine stillnessâ sounded gentle on the surface, but in practice it meant surrendering the right to fidget, slouch, scratch or sprawl.
Aunt Patricia obviously picked up on the term as well. She gave a satisfied little hum from her chair. âSome âfeminine stillnessâ will do him much good, Marian,â she said, not troubling to lower her voice. âSuch a wonderfully useful idea to learn important lessons: Obedience, deference, restraint. Children his age should learn the value of being seen and not heard, and that is especially true of proper young girls. Demure, well-mannered children ought to present themselves sweetly and agreeably⌠none of this complaining rebelliousness that seems so common today.â
Edwardâs throat tightened. His auntâs words seemed ominous and revealing. They sounded like a verdict which he was helpless to appeal. âSeen and not heard.â The phrase settled coldly in him. Outside, another peal of laughter broke through the window from the playground. It made him feel a sudden, aching envy. While they laughed and played, he sat silently enveloped in velvet and lace, displayed just like his aunt wanted: pretty, fragile, obedient and still.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by ace on Yesterday at 04:22:07 AM »
I don't see any issues with getting inspiration from Vicky's story, in fact I'd say most stories are a result of earlier works of fiction. I think you're doing a wonderful job with your interpretation. Keep up the good work and as always, it's great to see you back here.
Ace
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 02, 2026, 06:56:24 PM »
This âdressingâ took nearly half an hour, and by the end of it Edward felt less like a boy being femininely dressed than a small monument being assembled piece by piece. Miss Vale had a well-appointed dressing area in her studio space complete with a large tri-fold mirror, a padded chair and a side table. Miss Vale led him over, and the ladies helped him out of his pink dress and shoes so he stood again just in his white tights before the large mirror. Edward felt very nervous and self-conscious. The ladies, meanwhile, seemed wholly unperturbed and began getting him into the ornate Victorian outfit.
First, he was surprised when Mrs. Vale laced a firm little corset snugly around his waist. She explained it would keep his shoulders open and his spine tall. The first quick tug of the laces stole a little of his breath, and the second made him feel as though someone had drawn a careful line all the way around the middle of him and cinched it closed. The stiff fabric was cool at first, then quickly warm where it pressed against his skin. He immediately felt confined in a totally unfamiliar way as she tied the laces securely behind his back. It was not painful, but it was intimate and inescapable.
Miss Vale then slipped a white silk chemise over his corset, soft but unfamiliar beneath his arms. Its lace-trimmed edge danced over his skin, impossible to ignore. Edward shivered despite himself. Everything felt strange and new. His nerves were electric, and every new sensation only heightened his embarrassment.
With his chemise in place, Miss Vale carefully tugged and straightened his white tights so the seams were properly aligned. Then she had him step into a crisp white petticoat! When she pulled it up around his waist, it stood out with a noisy whisper. She had him hold up his slender arms, and a second fancier petticoat followed right over his head. He had never even worn one petticoat, and now he had on two! The second one was trimmed in rows of ruffles that brushed together whenever he turned. He was immediately conscious of electric sensations in his panties as his petticoats rustled gaily over his pretty white tights.
Edwardâs thoughts kept darting between obedience and alarm. Each elaborate layer made the process feel less theoretical. The chemise slithered against his skin, and the tights made his legs feel so girlish. The petticoats erased the straight lines he was used to and swished against his legs. He felt his breath quicken, but it was shallow due to the corset. The feeling of being inexorably encased in elaborate layers of vintage femininity was overwhelming. A part of him kept helplessly asking what sort of thirteen-year-old boy found himself being transformed into a prissy Victorian girl for a portrait on a Tuesday afternoon?
Next came the gorgeous gown itself. The velvet was a pale lilac color, silvered in shadow and almost pearly where the light touched it. It had panels of satin that caught the light in glossy folds like the inside of a seashell. Edward felt the fabric before he felt its weight. The velvet brushed his skin with a cool, dense softness that seemed gentle until it settled over him and became heavy. The scent of lavender assailed his nostrils. The satin panels slipped and whispered against his petticoats incessantly. The fancy Victorian frock boasted gauzy overskirts that were edged with scalloped lace, tiny faux pearls, and delicate beads that shimmered at the slightest movement. Once the high collar was fastened around his neck, it was impossible to ignore. Cream lace climbed the stiff collar all the way up his throat so that it brushed his chin. It then spilled in delicate frills down the front of the bodice and around the cuffs. Pearl buttons on the bodice formed a shiny line, while silver threads and tiny embroidered blossoms had been sewn into sprays like enchanted vines along the waist and hem. The skirt widened in graceful layers, so that when Edward looked in the mirror, he realized he looked almost like a fairy-tale princess from an illustrated book. Mrs. Vale fastened all the hooks and buttons on the old dress with care, smoothing the fabric as though greeting an old friend.
More accessories were added. A cameo brooch was pinned at Edwardâs throat, and a narrow pale lilac velvet sash was tied at his waist in a bow with long trailing ends. His feet were fitted into the ornately embroidered saddle shoes, stitched with tiny lilac vines, pearl-colored thread, and little loops of silver that looked like gifts from a fairy godmother!
At this point, his Aunt Patricia could no longer contain herself. She stood up and walked over for a closer look with a broad grin of satisfaction on her face. âOh, itâs just perfect⌠just as if it were made for him!â
The other ladies smiled in amused agreement. She was the one bankrolling this entire endeavor after all, so no one had any incentive to contradict her.
She addressed her nephew directly, âDoesnât it feel wonderful to know how lovely you look my dear? You look like a perfect little Victorian miss!â
Edward flushed again. Meekly, he answered, âYes Aunt Patricia⌠thank you.â At this point, he knew it was much better just to agree. He really had no words to describe how awkward and self-conscious he felt.
Miss Vale gently touched his shoulder and had him slowly turn so his aunt could see the full effect. Edward felt the heavy velvet and billowing petticoats rustle ceaselessly as he slowly twirled under the unfamiliar weight.
Aunt Patricia practically squealed with delight, âSimply wonderful!â
His mother looked on shyly but remained silent as her sister momentarily seemed to take up all the space in the room. After another moment, Aunt Patricia returned to her chair.
Miss Bell then took the lead. She had a case full of combs, pins, little covered jars, and a narrow curling iron that looked very imposing to Edward. She had him sit carefully on the dressing chair and quickly snapped a white nylon cape around his neck to protect the lovely dress. Mrs. Bell deftly divided his hair into small, exact sections and wound each one into golden brown Victorian ringlets, matching the old photograph curl for curl as closely as she could. Edward was keenly aware of the sensations as she gently tugged and combed his long hair back and forth. He very much felt like a doll on display as his Aunt Patricia, his mother and Miss Vale watched cheerfully.
Mrs. Bell took pains to tease each ringlet into place exactly where she wanted it. She misted it all with enough hairspray that Edward could smell the sharp sweetness of it whenever he turned his head. He was amazed how quickly and carefully his new ringlets were arranged and then fixed with even more spray. Finally, when she was satisfied with his curls, she meticulously fastened an extravagant Victorian bow of pale lilac velvet and cream ribbon into his new ringlets. Its loops were arranged almost like a soft crown and its long tails fell behind his ears like royal streamers.
She stepped back with a little flourish said, âTa da!â
Aunt Patricia and even his mother seemed thrilled with the adorable results.
Edward gasped as he looked at himself in the mirror. The sight of his carefully arranged ringlets made him feel so exposed and sissified.
âHold still just one more moment, darling,â Mrs. Bell murmured as she adjusted the hairbow.
âIâm doing my best,â Edward said helplessly.
âI mean inwardly as well,â Mrs. Bell replied, smiling. Edward had no idea what that meant.
Miss Vale looked over the old photograph. âHe is doing very well. The first sitting is always the hardest because we are all learning the shape of the work together.â
Again, Edward had little idea what the âshape of the workâ meant, but by now he was well aware of the unwanted tingling in his panties. It was all confusing, but deep under his dress, petticoats, tights and panties, his body was reacting in an unexpected way to all these sensations. He tried to take shallow breaths, but he was full of restless, uncomfortable awareness. The corset held him so upright that every breath felt measured. The petticoats shifted whenever he moved, whispering around his legs, and the weight of the gown made his shoulders feel smaller beneath it.
He was dismayed to learn there would also be makeup. Mrs. Bell began by smoothing on the thinnest veil of foundation, blending it carefully around Edwardâs nose, chin, and brow so that even the slightest blemish seemed to vanish. Then, she brushed the faintest pink blush onto Edwardâs cheeks and stepped back again to judge it. Too pale, she said, and the painting would look chilly. Too bright, and Edward would look as if he had run up the studio stairs instead of arriving from a fairy-tale carriage. After a few minutes, they found the exact rosy shade Miss Vale wanted: light enough to seem natural, but warm enough to echo the glow of the pale lilac velvet around his face.
Edward recoiled slightly as a trace of pale pink lipstick was next applied to his lips, soft as the inside of a rose petal. Acutely aware of the slick feeling of the lipstick, Edward sat stiffly. It felt so emasculating and feminine to be made up this way as Miss Vale studied his face closely. It only added to the tension under his skirts. He felt a small bead of cold sweat dribble down his back under all the layers.
âJust a touch more pink I think Mrs. Bell,â she decided after a few moments.
âOf course,â Mrs. Bell replied. Then she traced over Edwardâs delicate lips with another coat of slightly brighter pink lipstick.
âThatâs perfect,â Miss Vale said approvingly.
Edward sat helplessly while Mrs. Bell then touched a little mascara to his lashes so his eyes would stand out demurely. Satisfied with his hair and makeup, Mrs. Bell removed the nylon cape, and Edward gazed at his unfamiliar reflection in the mirror. The makeup unsettled him in a different way from the gown. The foundation and powder changed his own face by degrees into something softer. He looked smoother and much more fragile. The blush gave him a doll-like complexion. He was keenly aware of his slippery lipstick, and he tried not to press his lips together too much after Mrs. Bell cautioned him not to smear it. The mascara made his lashes look strangely accentuated and doe-like.
Edward flushed as he studied himself in the mirror. The boy looking back had not disappeared completely, but he was overtaken by softness. His stiff ringlets cascaded girlishly, and his delicate features were much more prominent. His pale pink lips gave him a demure and feminine air. It was as if someone had taken the daintiest parts of his face and arranged the light around them. He had to look away.
During these preparations, he was continually aware of the way he just sat so passively while others made decisions about how he would look. Edward felt a fleeting urge to interrupt, to demand they understand he was not their doll. A fragile and precious doll, however, is exactly what he felt like now. His cheeks burned as he sat there being studied and adjusted relentlessly, but he managed to swallow his protest.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 02, 2026, 01:22:58 PM »
When he was finally dressed, his mother guided him to the full-length mirror, and he looked uneasily at the girlish figure staring back. Blushing, Edward gaped at his adorable pink dress and shiny shoes, unsettled by the feeling that the outfit had been waiting for him before he knew it existed. He stood motionless while his mother fluffed the sleeves and smoothed his skirt. Being buttoned into a delicate girlsâ Sunday dress as a prelude to being put into an older, grander dress felt totally surreal.
For several seconds, Edward could only stare. It was not merely that he was wearing s pink dress... it was the way his feminine outfit seemed to look so natural on him. The flutter sleeves made his shoulders look narrow and soft, the ribbon at his waist gave him a dainty shape, and the flared skirt stood out prettily over the white tights as if it belonged there. He looked shockingly girlish. An embarrassed heat crept up his neck as he shifted one shiny Mary Jane awkwardly behind the other.
Aunt Patricia, in contrast, was thrilled. She seemed unable to contain herself, smiling at him as though some cherished hope had suddenly stepped out of the mirror. âOh, Marian, just look at him,â she breathed, delighted. âIsnât he darling? That dress suits him even better than I imagined.â Edwardâs blush deepened. He wanted to deny it, but the mirror made denial feel useless.
The whole ritual seemed to serve its purpose, however. He felt as if had entered a girlish daydream completely separate from his ordinary life. Still a little in shock, he couldnât deny how feminine he looked⌠and felt. Most unsettling was Aunt Patriciaâs confidence. She seemed so delighted to see her plans for him finally coming to fruition.
âYou look like a pretty little princess!â Aunt Patricia exclaimed, âIâve said it more than once to your mother. You are much too pretty to have been born a boy!â
Studying his sissified reflection in the mirror, Edward found it hard to argue. Now, it was time to depart. They all stepped outside and got into Aunt Patriciaâs large, fancy sedan. It had rained earlier, but the rain had stopped. The car engine purred to life, and she drove them straight to Miss Valeâs studio through the wet streets.
Edward sat quietly in the back with his skirt smoothed carefully over his knees and his patent Mary Janes placed together on the floor mat. His thoughts and emotions tumbled restlessly. His mother sat in the passenger seat in front, and Aunt Patricia glanced back at him from time to time in the mirror with a look of satisfaction.
Edward watched the streets pass and felt oddly displayed even inside the car, as if the sedan were a polished carriage carrying him toward something magical. They parked near a small square, and the studio was only a short walk away. The square contained a little park and playground, and on that first Tuesday the playground was damp and nearly empty. Still, a few children chased one another between puddles, shrieking whenever mud splashed their shoes.
From the safety of the concrete sidewalk, Edward slowed without meaning to, his eyes following the flash of their shoes through the wet grass. For a second he imagined stepping off the pavement, running after them, letting the darling black patent Mary Janes darken with mud and the demure pink skirt get splashed with rainwater. The very thought made him glance down in dismay. His pretty dress felt much too visible in the gray afternoon, its pinkness practically announcing his dainty appearance. His unfamiliar white tights showed every careful step, and his Mary Janes clicked on the sidewalk with a tidy sound that seemed impossible to hide. The satin ribbon in his hair was a reminder that he was already becoming someone else. He felt a flash of humiliation and wondered whether the other children would notice him.
âNot too close, Edward,â his mother reminded him gently, laying a hand on his shoulder before he could drift toward the gate of the playground. âYou are dressed far too nicely to get near that dirt and mud.â
Aunt Patricia added with a tone of warning in her voice, âThatâs right, darling, we simply wonât have you ruining your pretty new dress.â Edward looked down glumly at his pristine skirt, smooth white tights, shining shoes, and pink-polished nails. He felt a sharp unfairness of being kept spotless and dainty for something he wished he could escape. In a few minutes, he knew he would not be running or shouting or even standing like himself. He felt a pang of jealousy before his sitting had even begun, and his aunt purposefully guided him toward the studio door.
Miss Valeâs studio occupied the top floor of a narrow brick house near the square, and soon they were welcomed inside. Miss Clara Vale herself was a lively lady with inquisitive eyes. She had silver-streaked brown hair pinned simply at the back of her head, dark eyes that missed very little, and hands stained faintly with paint. Her studio felt less like an ordinary workroom than a private retreat. The tall windows were draped in sheer white curtains tied back with rose-colored ribbons, so the rainy light entered softened and pearly. The pale walls were touched with a faint blush tint and hung with small gilt-framed sketches of flowers, swans, and serious young ladies in lace. Shelves on the walls held jars, brushes, rolled canvases, plaster hands, and little bowls of pigment. The air smelled of linseed oil, lavender soap, turpentine, rain, and the powdery sweetness of roses.
âWelcome, please come in!â she said warmly. Looking intently at Edward for the first time, she added, âand of course this must be our little Edward!â Admiring his dress, she added, âwhat an adorable frock!â She continued, âwhen your aunt suggested it, I thought it seemed a little odd. But now seeing you in it, I can honestly say it becomes you.â With an approving look, she said. âAnd what a brave young man for taking this project on!â
Edward cringed, but he managed to put on a weak smile.
She looked at him seriously, âI assure you, this will be an experience you will never forget!â
Edward gulped, and said shyly, âThank you Miss Vale.â He didnât really know what to say. Dressed as he was and knowing why he was here, his emotions were all over the map.
She gestured to a second lady standing in the studio, âAnd of course let me introduce Mrs. Bell. She is a stylist who often helps me with achieving just the right look for my subjects.â
The slightly younger woman with a sturdy build and friendly eyes spoke up, âSo nice to meet you all!â Appraising Edward for the first time, she added, âItâs uncanny how much he looks like his ancestor. She gently touched Edwardâs hair and said approvingly, âI think this gorgeous honey-brown hair will work just beautifully!â
Edward shifted his feet skittishly and blushed pink. He didnât know how to feel about that.
âLadies,â Miss Vale turned to Edwardâs mother and aunt, âYou are welcome to have a seat over there.â She gestured to a pair of comfortable-looking nearby chairs. Turning her attention back to Edward, she said eagerly, âLetâs jump right in, shall we, and get our young Victorian lady properly dressed.â
In no time, Edward found himself immersed in the afternoonâs second intense flurry of preparation.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 01, 2026, 11:39:20 PM »
Edwardâs first portrait sitting was arranged for the following Tuesday after school. He was excused from his usual piano lesson, which made the portrait seem slightly more agreeable. By four oâclock, however, with the school day behind him and the whole afternoon somehow already claimed, he had begun to realize that his music lesson might have been easier.
Soon after he got home from school, Aunt Patricia arrived with a large white box tied in pink ribbon and announced that she had brought âa little gift to begin properly.â Edward didnât know exactly what to expect, but he hesitantly opened the large box. He lifted the cardboard lid and gasped involuntarily at what he saw. Inside, folded in tissue paper, lay a summery pink girlsâ dress with a rounded collar and flouncy flutter sleeves! The adorable dress had a ribbon tie at the waist and a flared skirt. There was also a pair of pristine white tights, a delicate pair of satin panties trimmed in lace and a shiny pair of black patent Mary Janes shoes.
Edward stared at the clothes in shocked surprise. âWho are these for?â he asked futilely, though there was no one else in the room they could possibly fit. âYou meanâŚ?â
Aunt Patricia interrupted with a smile. âOf course. Miss Vale and I had a long chat. Sitting for a proper portrait means getting you into the proper frame of mind. If you are truly to echo your great-great grandmother as a young girl, Miss Vale and I think that achieving that right girlish mindset is crucially important.â Her lips curled in a slight grin as she continued, âI suggested to Miss Vale that getting you a dress of your own to wear might be an elegant way to accomplish that. She giggled a bit, but then she agreed that it would probably do the trick.â
Edward looked disbelievingly at his mother as he tried to process what was expected of him now. Aunt Patricia had gone too far! Unfortunately, he was deflated when he saw his motherâs reaction. His mother gave him an almost apologetic look as she gently lifted the dress from the box. âMiss Vale says proper preparation for a true portrait begins well before you are in front of the artist, dear,â she began softly.
Aunt Patricia piped in, âyour mother is right, sweetie, and youâll need to get into a more feminine frame of mind to do your great-great grandmother justice.â Then she beamed and practically licked her lips, âYouâre going to make an adorable little girl!â
Edward opened his mouth in protest, but no words escaped. Over the past couple of days, he had tried to come to grips with the idea of posing for a portrait dressed as a girl. He hadnât dared mention it to anyone at school, and he was already worried that somehow they would find out. As he had wrapped his brain around the prospect, he had at least taken solace in the fact that it would just be something he did in the privacy of the artistâs studio.
Now, his Aunt Patricia had breezily tossed aside those expectations. With a sinking feeling, he realized he would be wearing this adorably girlish dress when he left his house today. His cheeks flushed red. What if someone saw him? He grimaced as he realized that preparing for his portrait sitting would be its own process.
Then, things begin to happen fast. In short order, Edward was swept helplessly along as his aunt and mother set to work on him. He was ushered into his motherâs large bathroom to get ready. Soon, he was getting scrubbed clean as if he were going to church. His mother pulled off his tee shirt and went to work on him with a damp washcloth and some sweet-smelling soap. Then, his face, hands and ears were washed, and his fingernails were brushed free of dirt.
Once he was deemed suitably clean, his mother held out the lacy pink satin panties from the box and said, âPut on your panties, dear, while your aunt and I wait for you in the bedroom.â
In a tiny voice, Edward asked, âcanât I at least wear my normal underwear?â He added helplessly as he grasped at straws, âno one will knowâŚâ
âYOU will know, sugar,â Aunt Patricia chimed in with a chuckle, âHow could you possibly feel girlish wearing your boring boysâ briefs?â
Wordlessly, he took the lacy garment with a look of disbelief. He stood almost frozen holding âhisâ panties as his mother and aunt walked into the bedroom and closed the door behind them. Alone in the bathroom, he stood there several seconds just looking at the satiny underwear he held gingerly between his thumb and index finger.
âDonât dawdle now, Edward!â his aunt called loudly from outside the door, âwe donât have time to waste!â
âYes⌠Aunty,â he replied meekly. Cringing, he slipped off the khaki shorts he had been wearing. Then, with a feeling of helplessness, he pulled on the panties. He shivered as the silky, lace-trimmed fabric slid over his skin. He saw there was a precious little pink bow on the waistband in front as he pulled them into place. After several more moments, he reluctantly emerged red-faced from the bathroom, holding his hands uselessly in front of him.
âOh my goodness, how darling!â Aunt Patricia exclaimed when she saw her pantied nephew for the first time.
Edward just stood there speechless while his mother smiled nervously. Everything seemed to happen in a blur as he was quickly cocooned into the precious new outfit his aunt had bought for him. His mother helped him pull on the clingy white tights, and his pulse quickened as they slid up his slender legs. Next, it was time for the dress⌠his dress. His aunt held it out and gestured for him to step into it. She pulled the darling sleeves over his arms and then cheerfully buttoned him into it. As he felt its delicate contrast mesh top wrap snugly around his chest, Edward was dismayed how well everything seemed to fit. The generously ruffled short sleeves settled cutely over his shoulders, the ribbon circled his waist daintily, and the bouncy skirt fell to precisely the right length just at his knees. His mother buckled the perfectly sized Mary Janes neatly onto his feet while Edward stood helplessly at the rapid turn of events.
Aunt Patricia watched with open approval. âThere,â she said. âI see I got the sizes just right. Just look how naturally his dress drapes him, Marian.â
His mother nodded quietly. Edward got his next unpleasant surprise when she sat him down at her vanity and reached for a bottle of nail polish.
âNail polish, too?â he managed to squeak.
âIt was your auntâs suggestion, sweetheart,â she explained a bit sheepishly.
As she brushed pale pink polish onto the first nail, Aunt Patricia explained, âIt will make your nails look much neater, and it will complement the rest of your adorable outfit, dear.â
âItâs just a hint of color, dear,â his mother added almost apologetically. He watched in glum disbelief as she painted all his fingernails with the pale pink polish.
Edward held his fingers apart while the polish dried to a glossy shine. He felt so sissyish and absurdly aware of his own hands. While his nails dried, he watched in the mirror as his mother tied his golden-brown hair back in a loose ponytail with a pink satin hair ribbon âto keep things tidy.â
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 01, 2026, 10:47:04 PM »
Edwardâs thoughts bounced abruptly back to the present. At his motherâs insistence, he had been put back into the horribly childish blue knee suit for his auntâs visit. âThat suit was not cheap, Edward, and she loves seeing you in it,â his mother had said as she had tied the floppy bow before his auntâs arrival.
Now in the family dining room, he looked to his mother and aunt with hesitant curiosity. He felt like such a sissy in his little knee pants and loafers. Already nervous, Edward heard his aunt speak first, and she was so bluntly direct it befuddled him.
âMiss Clara Vale has agreed to paint you in it, dearâ his Aunt Patricia announced with a smile.
âWhat?â Edward asked, very confused. As she often did, his aunt had seemed to skip over any explanation and just assume everyone would go along with her wishes. He had absolutely no idea what she was talking about.
His mother continued, glancing almost involuntarily at her sister. âA proper portrait, dear. Not merely a photograph. Something we can keep in the family.â
Aunt Patricia piled on before she could stop herself. âMy idea, really,â she said. âAnd my treat. Iâm going to pay for the whole thing. Marian only needed convincing that you might be brave enough to do it.â
Mrs. Gray gave her sister the mildest possible look of warning, but then she turned back to Edward. âSweetheart,â she began, âyou look so uncannily like your great-great grandmother at your age that Patricia thoughtâand I have come to agreeâthat we should not let the moment pass without capturing it properly.â
Still befuddled, Edward gulped nervously, âWait⌠what⌠a portrait?â It was starting to dawn on him what they were getting at. âMe?â he asked incredulously, his cheeks reddening with embarrassment.
His mother smiled, but there was something nervous and almost shy in the expression, as though she were still borrowing courage from her sister. âYes, you. I know it is an unusual thing to ask. There would be several sittings, perhaps over a few weeks. You would just pose as your great-great grandmother did, in this gown, and let the artist capture a unique moment of our family history.â
Aunt Patricia nodded vigorously. âMiss Vale is absolutely perfect for it. I have spoken with her already. She understands likeness, delicacy, family feelingâeverything.â
His motherâs smile tightened now at the edges, but she did not contradict her sister. âBy all accounts, this Miss Vale is very talented,â she said. âAnd Iâm sure she would capture you beautifully.â
Edward realized, with a sinking clarity, that this request had been arranged long before it reached him. Aunt Patricia had already found a painter, offered a fee, convinced his mother, and now stood beside the cedar chest as if waiting for the curtain to rise on an idea she had already decided on. His mother seemed carried along by Patriciaâs certainty, acquiescing to each bright suggestion with a soft nod or a quiet âperhaps.â That made Edward feel trapped. The unusual request had been presented gently, but it had gathered momentum before he had even been asked.
Edwardâs first feeling was not refusal exactly, but a quick, hot flush of embarrassment so complete that his lip quivered. To be painted wearing a girlâs dress seemed absurd. The more he thought about it the less he knew how to respond. Boys his age climbed trees, scuffed their shoes, forgot to comb their hair and pretended not to care how they looked. They certainly were not asked to sit in a Victorian dress for a painting. His heart wanted to say no immediately. He didnât want to hurt his mother, but the idea of wearing this dress made his ears burn with discomfort. Still, there was a very small part of him, quieter and harder to name, that was a bit curious. Unfortunately, it made him hesitate. The way his mother touched the gown made it seem less like a costume than a keepsake with a heartbeat.
Aunt Patricia obviously detected this barest hint of uncertainty on his blushing face, because then she handed him the old photograph they had pulled from the cedar chest. Edward stared at it. It was like looking in a forgotten mirror. The face was not his, and yet it was. This girl had his same narrow chin, his same watchful eyes, and the same slight crease between the brows he displayed when thinking.
Aunt Patricia watched him with barely contained triumph, while his mother watched more anxiously. Seeing the photograph made the request feel different. He was not being asked merely to dress up. He was being asked to stand in a place where memory and likeness met. He had to admit he really did look like the girl in the old photo⌠or she looked like him.
That was what troubled him most. If the likeness had been only slight or passing, Edward might have been able to summon some strength to refuse. But the photo made him feel suddenly divided: one part of him was the boy in the den playing video games, certain he wanted no part of old Victorian gowns; another small but insistent part was curious about the old image, wanting to understand something he couldnât quite put his finger on.
Still, when he tried to imagine actually doing it, he cringed. It was one thing to say, in the abstract, that he resembled his ancestor. It was another to picture himself buttoned into her ornate old dress for his portrait to be painted. It all seemed a little absurd. He tried to think of a way out of this.
The room was silent for several long moments. Edward nervously wondered what âseveral sittingsâ actually meant. Who was this Miss Vale? Where even would this portrait be hung? He had too many questions to make sense of them. Meanwhile, his mother and overbearing aunt waited expectantly. He looked from the photograph to his motherâs timid face, then to Aunt Patriciaâs enthusiastic one, and finally to his great-great grandmother as a young girl in the pale lilac gown. The flush of embarrassment had not vanished, but it had changed shape. Despite himself, he now felt a weight of expectation on his narrow shoulders. This was accompanied by the uneasy knowledge that Aunt Patricia had already presumed his agreement.
After a few long moments, he surrendered to the pressure without really meaning to. He didnât agree, exactly, but he simply stammered, âI⌠I guessâŚâ The words slipped out hesitantly and quietly almost of their own accord.
Aunt Patricia immediately took that as a âyesâ and squeezed his shoulder with open delight. âI knew you would understand,â she said. âMarian, you see? I told you he has the temperament for it.â
Mrs. Gray took his hand tenderly and spoke softly, âThank you, Edward.â She seemed relieved that Edward was not going to protest her sisterâs plan. Although she looked as if she might correct the word âtemperament,â instead she only nodded and smoothed the tissue paper around the gown.
Edward noticed the nod. It was the way his mother often yielded to Patriciaâs confident intentions, especially when Patricia wrapped them in generosity. At Aunt Patriciaâs urging, his mother carefully held the old dress in front of him while he stood meekly. Still wondering how this had happened so rapidly, he felt the weight of the lush fabric brushing against him.
Aunt Patricia exclaimed, âit looks to be nearly a perfect fit!â Then, she added, this is going to be wonderful!â
From that moment forward, Edward would find himself unable to separate the portrait from Aunt Patriciaâs will. His motherâs tenderness mattered to him, but Aunt Patriciaâs certainty was the engine beneath it all. She had imagined the portrait before Edward knew there was anything to imagine, arranged the painter, offered the money, and spoken as if his agreement was merely window dressing on a course that was already laid out. That made him wary of her affection. It was real, but it also seemed to arrive with other intentions sewn into the lining.
Edward now thought uneasily about what might lie ahead. Belatedly, he began to fret about what he had really agreed to. He hadnât even really agreed as much as he had just surrendered. Sighing nervously, he realized it was too late now. Things seemed to already be in motion.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 01, 2026, 09:22:40 PM »
In the late spring, when school afternoons began to feel brighter, and summer was just around the corner, thirteen-year-old Edward Gray sat down awkwardly in the family den to play a video game. It was a rainy Saturday afternoon, the sort of afternoon when the windows blurred silver and the cozy house smelled faintly of potpourri. As he logged in, he absentmindedly wondered what his mother and Aunt Patricia were up to in the dining room.
He sighed slightly as he rejoined his game. He quickly realized that he couldnât really concentrate on his game with his aunt here, especially with the way he was dressed at the moment. He had always felt a little self-conscious around his Aunt Patricia. She had been a constant figure in his life in particular after his father passed away several years ago. She was very well-off from a long-ago divorce settlement, and he vaguely knew she helped his mother out financially. He didnât know much about the specifics. She had always been kind and generous to him and his mother, but often it all felt⌠smothering. With a subconscious shrug, he tried to shift his attention to the game.
Meanwhile, his mother and Aunt Patricia were going through some old family items in the dining room. Earlier, they had opened a long cedar chest that had sat untouched in the corner of the dining room for years. They now had a small collection of family odds and ends spread out on the large dining room table and were sorting through them.
âI told you Marian!â Patricia exclaimed, âlook at that old photo⌠the resemblance is uncanny!â
Marian Gray looked at the old, sepia-toned photograph in her hand with a new appreciation. She hadnât seen this photo in years. The oval photograph in a tarnished silver frame depicted a demure young girl who sat very straight up in a pale Victorian gown on a carved wooden chair. Her eyes were lifted as if she had just heard someone call from another room. âIt is striking, Patricia,â she had to admit. She looked from the photograph in her hand to the partially unwrapped package on the table before her. The old tissue paper crinkled at the touch, and it smelled of lavender sachets and the deep, secret scent of old cloth.
âLetâs just see what he thinks,â Patricia urged. After a brief pause, Marian nodded silently.
In the very next instant, Edward heard his Aunt Patricia calling him. âEdward, dear,â Aunt Patriciaâs voice rang out, âwould you come join your mother and me in the dining room, please?â Although it was phrased as a question, her tone was insistent.
Edward was annoyed at the interruption. He grimaced slightly. Although he had learned over time it was usually best to see what his aunt wanted, he was tempted to just keep playing. After another few seconds, however, he thought better of it. He reluctantly paused the game. It was nearly impossible to ignore her, and stalling usually just made it more uncomfortable.
As he stood up from the couch, he heard her voice again, this time louder, âOh Edward sweetie, did you hear me? Your mother and I are waiting for you!â
âIâm coming⌠Aunt Patricia!â he called back. She always looked a little peeved if he didnât address her as âAunt Patriciaâ or âAunty Patriciaâ or sometimes just âAunty.â He always tried to remember to add that and forestall any additional drama. It all kind of seemed silly to him, but he had no interest in rocking the boat when it came to his aunt.
Rounding the corner into the dining room, Edward saw his mother and aunt standing next to the open chest. His mother was holding what looked like an old dress that Edward had never seen. His Aunt Patricia hovered beside her sister with an eagerness she did not bother to conceal. The dress, Edward would soon learn, had belonged to his great-great grandmother. As Edward looked at it curiously, it seemed to him less like clothing than a preserved piece of another century.
âMy goodness it took you so long I thought we might have to send out a search party!â his aunt chided him with a cheerful smile.
Although it had been no more than twenty seconds since she first called him, Edward replied meekly, âSorry⌠Aunty.â
âOh you little rascal,â she said with a barely stifled giggle, âalways up to some shenanigans!â Then, for the umpteenth time it seemed, she beamed, âI still canât get over how handsome you look in that darling suit!â
Edward cringed to be reminded of his attire, but he kept silent. If anything, he was a meek and obedient child most of the time compared to his peers. He was naturally shy, and now in his adolescence he tried to avoid the spotlight even more. For a moment, his thoughts drifted.
He was well aware of certain things about his appearance, mostly because other people often mentioned them. For example, his mother had always kept his light brown hair a little long for a boy. It was not deliberately fashionable but difficult to keep trimmed because it curled at the ends and never seemed to lie as short as he wished. His face, too, had a delicacy he could not deny: a narrow chin, fine-boned cheeks, dark watchful eyes, and a mouth that looked more thoughtful than bold. He did not dislike these things exactly, but he knew by now that they projected a certain softness to others.
His Aunt Patricia had always noticed these things too. She had no children of her own, and so, from the time Edward was small, she had poured a great deal of her unused attention onto him. She was loving in her way, lavish and admiring, but her admiration often made him uncomfortable because it seemed to pass over everything boyish about him and settle instead on what she called his prettiness. âSuch a pretty child,â she would say, smoothing his hair or turning his chin toward the light. âThose eyes, Marian. And that mouth. Quite refined.â
Over time, Edward had learned to endure the remarks by pretending not to hear them. Her gifts to him had always followed the same pattern. Other boys received baseball gloves, toy race cars, model trains or video games. Aunt Patricia brought Edward things like fine stationery and monogrammed handkerchiefs. She once presented him a porcelain keepsake box for small photos and trinkets, and another time he received a little velvet case containing pearl shirt studs for occasions Edward could not even imagine. She seemed to have no conception of what a typical boy might want. Everything she chose was polished, scented, folded in tissue, or tied with ribbon, as if refinement itself were a present. It seemed to Edward that she meant every gift kindly, but her generosity always leaned in a very particular direction.
For his birthday when Edward was ten, for instance, Aunt Patricia had arrived with a parcel about the size of a book, wrapped in ivory paper and tied with a satin ribbon so pale it was nearly white. Edward had accepted it with a slight sense of trepidation.
âOpen it carefully,â Aunt Patricia had said, settling beside Edward as if the ribbon itself deserved respect. Inside was a small leather case lined with blue silk. Nestled in it lay a silver-backed hand mirror and a matching comb, both engraved with a delicate spray of lilies.
Edward stared, unsure what expression would be safest. âFor me⌠Aunt Patricia?â he had asked with a squeaky little voice.
âOf course, sugar,â Aunt Patricia had gushed, delighted. âFor that lovely honey brown hair of yours! A young person with such refined features ought to have refined things.â
The mirror was beautiful; that was the trouble. It was cool and heavy in his hand, made with a care he could not dismiss, and yet it seemed meant for someone quieter, prettier, and more willing to be admired.
âThank you, Aunty,â he had croaked, because Aunt Patricia had been watching him with such hopeful pleasure. She had kissed his forehead and smoothed the hair the comb was meant to tame.
âThere,â she said cheerily. âI knew you would appreciate it.â Edward did not know whether appreciation was the name for what he felt, but he kept the case closed in his drawer for months, taking it out only when no one could see.
And just last year, when he was twelve, she had announced her intention to buy him a proper new suit for Easter. This had all sounded innocent enough until he saw it on Easter Sunday morning. When his mother brought a pink garment bag into his bedroom and unzipped it, Edward recoiled and cringed at how childish and fancy it was! With a looming sense of dread, he had pleaded with his mother not to make him wear it, but she insisted. Aunt Patricia was coming over soon, and they were all going to a fancy Easter dinner at his auntâs country club. His mother had told him almost sympathetically, âSweetheart we canât disappoint your aunt after she made all this effort for you.â
When Aunt Patricia had swooped in to pick them up, she had gushed over how handsome and refined her nephew looked dressed in the monstrosity. âAbsolutely gorgeous,â she had proclaimed. âIt fits you beautifully, sweetie! It makes you look so cultured and dapper!â
Edwardâs exquisitely tailored âproper new suitâ was a baby blue wool blend, and the coat was actually a little waistcoat paired with matching blue knee pants that gathered with elastic at the knees! Underneath the coat, he had been buttoned into a billowy white silk shirt with French cuffs and subtle ruffles down the front. A baby blue ribbon tie was daintily knotted at the rounded collar, and the floppy silk bow looked much more prissy than handsome in Edwardâs opinion. Crisp white knee socks and a pair of matching baby blue loafers had completed the juvenile look. He had felt like such a sissy!
âThank you, Aunt Patricia,â he had managed to spit out. After a reproving glance from his mother he had reluctantly added, âItâs very nice.â
Then, as if that werenât enough, she had presented him with another daintily wrapped Easter gift. The wrapping paper was patterned with vintage Easter bunnies and tied with a fancy pink bow. When he had tentatively opened the second box, he discovered a large vintage doll. The doll was a young boy with lifelike features and honey-brown hair dressed in a darling blue suit that exactly matched the one he had been wearing!
His aunt had beamed as he held it up gingerly, âNow you have a little twin! Isnât he precious?â
Flabbergasted, Edward had been at a loss for words.
His mother had piped in, clearly taken aback but trying to be polite, âItâs... quite charming, Patricia!â then with a pointed look at her son, she added, âand what do we say Edward?â
âTh.. thank you... Aunty,â Edward had stammered, âItâs⌠great.â
The elaborate doll now sat prominently displayed on a shelf in the den. He shuddered as he recalled the memory of all the people at the country club gawking at him and the muffled giggles he occasionally heard from other children at nearby tables. No one else had been dressed in anything remotely like the outfit he had worn. He had felt so sissified wearing it, especially with the way his aunt had continually adjusted his floppy bow and brushed invisible lint off his coat throughout the dinner. Ever since, his pretty doll on the shelf had been a constant reminder of the experience, and the horrible suit still hung menacingly in his closet.
To his chagrin, Edward was now fastidiously dressed in that same fancified and juvenile suit today.
Active Sissy Stories / The Portrait of Edward Gray
« Last post by sissyboy1212 on August 01, 2026, 09:02:06 PM »
This story is an unabashed homage to the (I think) unfinished 2002 story "Under Aunty's Control" by Vicky. It can be found in Betty's archives here: https://buffalobetties.net/storytime/index.php?topic=611.0
This version is certainly not a direct replay, but anyone who reads it will immediately see many important borrowed elements from Vicky's story. I want to be very clear that my reinterpretation is a loving reboot that keeps many of her same themes. I enjoyed Vicky's original and want to give credit where credit is due. There are a small handful of key lines, usually spoken by a character, that are copied directly from Vicky's original. These are intended as intentional callbacks to her wonderful story.
I also used some AI, but I've heavily edited most of those sections. Thankfully, AI still has a very hard time striking the right tone for this audience (or any others who are paying attention.) Humans still matter.
Lastly, although the title echoes the title of the Oscar Wilde classic, there are no true similarities to that great work.
Wherever Vicky is, I thank her and hope she is well.
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on July 31, 2026, 07:25:55 AM »
The ladies snuggled back into the chairs. Connie took a sip of wine. They regarded him smugly. He knew that they had him utterly at their mercy. His erection had settled into a state of aching, expectant hardness. He attempted, not very successfully, to conceal his arousal, keeping his hands in front of him, his balls concealed by his fingers and the tumescent shaft behind his hand. Even so, the gentle vibrations of the plug, which he could feel in his coc-k, made the temptation to play with it almost irresistible. He discovered he could palpate it by the slightest flexing of his wrist, producing subtle ripples of pleasure, and coaxing little flows of juice from the tip. Even as he was doing this, he looked at his audience with as innocent a face as he could command.
Connie put down her wine and smiled.
âLet me explain, Tim. Cressida has asked us to make some friendly enquiries into your sexual status. I understand you were briefly interviewed by the staff at ESDS, but she thinks we could offer a more sympathetic approach. It is important for your employers to understand your needs, so that theyâll be able to provide appropriate support. Now, first of all, may I ask, would you consider yourself heterosexual?â
âOh⌠Yes, missâŚâ
âYou do seem to be, I must say⌠But there was some mention of your relationship with your fellow boot boy⌠Bobby?â
âW-was thereâŚ?â
âYou know there was. I believe there was an admission of someâŚmutual masturbation? Isnât that correct?â
âW-was thereâŚ?â He didnât like the way the questioning was going. He felt distinctly nervous. He unconsciously expressed his embarrassment by awkwardly crossing his legs.
âCareful, Tim. Donât trip.â
âMissâŚ? I c-canât remember exactly what I said⌠They were pressuring me, see? Bobby and I, weâve, like, always been good friendsâŚâ
âVery good friendsâŚâ
âYes⌠Heâs a nice guy. Weâve known each other since we were kids. In fact I miss him quite a lot, now Iâm with ESDS and heâs still at Pittâs Wood. We used to have funâŚâ
âTim, please answer the question. If you donât, itâll be the same as a lie, and Iâll have to turn this thing up to number three. Is that what you want?â
âN-no, miss⌠Well, I mean, maybe we did onceâŚâ Seeing her frown, he added, âI mean, a few timesâŚâ
âInteresting. But youâre not gay, right?â
âNo!â
âThis Bobby guy sounds interesting. I think we should get you two back together. What do you think, girls?â
âAbsolutely!â
âCanât wait!â
âIn the meantime, I think youâd better explain just what you two have been getting up to, and how it all startedâŚâ
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on July 29, 2026, 05:58:53 AM »
When Connie was satisfied, she sent Tim back into the other living room to await instructions.
âI think Cressida will be happy with what weâve got so far,â she remarked, scrolling through her phone. She changed the video card in the camera. âIâll grab some vidcaps from here later, too. With all our snaps sheâll have plenty of images to choose from.â
âWhy did she want a video as well?â asked Bridget.
âBasically, I think, as training material for the staff. As to whatâs coming next, goodness knows what her plans are!â
âHeâs had an easy time of it so far,â sneered Frieda.
âHe certainly has,â remarked Bridget. âWeâve treated him like a friend â a guest, almost. But now we have to get down to serious business. Heâs not going to like itâŚâ She smiled thoughtfully. âWell, I suppose actually he mayâŚâ
âItâs going to be intense,â said Connie. âWe only have a few days, and in that time we have to step up from mere coercion to conditioning him to accept any instruction and to perform any act, however humiliating, until a positive response is programmed into him, until he obeys without question, even without thinking. Itâs a tall order, but if we succeed we get all the perks Cressida promised us. We becoming a branch of the firm, and have free rein with all the trainees.â
âOnce he realises thereâs no alternative, no escapeâŚâ
âExactly, Frieda. He must lose hope entirely, and accept that his future is only with ESDS.â
They sat silent for a moment, contemplating the task ahead. Then Connie rose.
âLetâs rearrange things a bit. Move the camera so itâs directly in front of him. If we arrange three armchairs in the corner we can get a good view without getting in the way. Letâs make ourselves comfortable and enjoy the show. Maybe open that nice bottle of wine, shall we?â
âIâll get some snacks organised,â said Bridget.
âIâll do the chairs,â said Frieda.
âGreat, Connie smiled. Iâll get him ready. Back shortly.â
She disappeared into the next room. Tim was waiting patiently, hands clasped in front of him.
âYouâre a lucky boy, Tim.â (Despite his recent accession to adulthood, it had been agreed he would always be addressed as âboyâ.) âLetâs get you undressed. Youâre going to be a pageboy again for the rest of the evening.â
She helped him off with his maidâs uniform. Tim felt relieved. He was still smarting from the ordeal having to show off his panties. When he was naked, Connie started unpacking another Fantastex box.
âPageboy outfit mark two.â
âMark two?â queried Tim.
âModified shorts. Zip flyâŚI bet youâll make good use of that,â she smirked. What she was thinking of Tim had no idea. âAnd a couple of little appendages.â
The âlittle appendagesâ turned out to be a rubber butt-plug welded to the inside seam, a short slim stalk terminating in a small, smooth rubber egg, and a rubber retaining loop attached to the crotch. Connie was enjoying herself now. She pulled on a pair of surgical gloves.
âStep inâŚthere we areâŚnow, lean forward a littleâŚhands on the back of the chairâŚâ She picked up a tube of lube, squeezed some out onto the egg, and smeared it over. âKeep still⌠In it goes⌠Relax, Tim, for goodness sake! ThereâŚone last pushâŚâ Tim flinched. âDone. A bit cold, was it? I keep the lube in the fridge these days⌠Now the loopâŚexcuse my fingers⌠Pop everything through⌠There you go? Is that comfortable? No? Never mind, youâll soon get used to it.â
Alas, he knew he would. That wasnât the issue. After all the handling, he could feel himself beginning to swell, and the retaining loop behind his balls wasnât helping.
âYes, thank you, missâŚâ
âYou donât sound very sure. Didnât the girls at ESDS make you wear training pants? Apparently not. They should have done. These are the most basic modifications. A small smooth plug and a single retaining loop. Weâll move onto something more advanced, but all in good time. Deportment comes first, Tim. You canât do justice to a smart costume if youâre slouching or walking carelessly. The plug will keep your back nice and straight, and ensure you walk with small, pretty steps, whether youâre a pageboy or a maid. So weâll make it a fixture from now on. The retaining loop? Well, if youâre genuinely proud of your boyhood you should let everyone see it. Your pride, that is. Youâre getting more grown up now. You canât hide your light under a bushel any longer. Do you agree?â
âYes, missâŚâ
She glanced down at the growing bulge in the front of his shorts, and gave a faint nod of satisfaction. âThatâs better, isnât it?â
She adjusted his shorts, tugged down the frills, slipped the belt through the loops, and buckled it up.
âLook at you! A proper pageboy! Super. Letâs go show the others.â
She took his hand and led him back into the smaller living room. Bridget and Frieda had already taken their places. There were three glasses of wine on the table, and two bowls of snacks, as if they were about to settle down to watch a film, or their favourite serial. Connie ushered him back onto the steel plate and reattached the ankle chain. Then she took a seat next to her friends. Frieda handed her a remote.
âNow, Tim, let me explain. That little egg contains a vibrator and a rechargeable cell. I can make it vibrate fast or slow, and gently or not so gently. Let me give you a demonstration.â
She pressed a button. Tim gasped, and squirmed like a hooked fish. The women burst out laughing.
âOops, sorry⌠I accidentally put it on the highest setting. Letâs try number oneâŚno, two. How does that feel?â
The gentle but relentless purring of the plug transmitted itself to the whole of his lower abdomen. He felt his erection growing, slowly but surely. He clasped his hands in front of him, pressed against his hardening boyhood. He looked at Connie pleadingly, but he could see from the satisfied expression on her face there was to be no respite. He tried to move his feet but the chains held him fast. He tried to breathe slowly, and pressed his feet and legs together in a vain attempt at resistance.
Connie smiled. âJust relax⌠Enjoy it. Now we have you where we want you, we need to ask a few questions. You must answer truthfully, though. Every time you lie I shall turn your vibrator up one notch. Understand?â
âYes, miss⌠I wonât lie⌠HonestlyâŚâ
The more you give, the more I can give back.
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