Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Today at 10:44:20 AM »
âOh, let me see⊠Somewhere I have a hard drive with all of them on. But thereâs just a few on my phone⊠Theyâre all together in this one album. Thereâs three you havenât seen â Adrian, Nicholas and Samuel. Theyâre under their femboy names, of course. You can look at it, but donât look at anything else, okay? Iâm just going to see how Gwenâs getting on. Connie and the others will be back inâŠlet me see⊠about an hour or so. Just sit there quietly, all right? Iâll bring you tea and a couple of cakes.â
âThanks, MariaâŠâ
Tim was left alone to goggle at the photos. There were six in all. The ones he hadnât seen were entitled âAdrianaâ, âNikkiâ, and âSammiâ. Adriana was wearing school uniform, Nikki a leather miniskirt, and Sammi a very short yellow creation with a sort of little tutu skirt. She looked as though she was at a party â maybe a wedding! You could even see her panties. Was it her panties? Something⊠Tim went hot and cold. Was thatâŠ? It couldnât beâŠ
He studied all the photos again, carefully. The âboysâ all looked so great. And pretty comfortable in their outfits. Maria returned carrying a tray with a mug of tea and a plate with a selection of cakes. She pulled up a box and set it down, then went and fetched another chair for herself. She sat down.
âWell? Like them?â
âTheyâre allâŠgorgeousâŠâ
âYesâŠthey are. Adriana⊠He went to a boysâ boarding school. He was always jealous of schoolgirls in their pretty uniforms. Thatâs his favourite outfit now. Amazing how popular he is with the guys. And Nicholas⊠Very traditional upbringing. Now as a girl he can dress as cool as he likes. He wears the tiniest of tops, or nothing at all, just a jacket. After all, heâs got nothing to hideâŠâ
âThis oneâŠSammi. Her skirt is so shortâŠâ
âAh. Yes. You noticed. That's rather naughty. We thought weâd get away with it, but when she started moving about her dress rode up and oops, there is was, peeping out. Her chastity device.â
âIs thatâŠ?â
âYes. Her little thing all tucked up neatly in its little cage. Itâs de rigueur for every femboy, of course. If youâre going to present as a girl you accept it gladly.â
âIsnât itâŠuncomfortable?â
âFor some, but only at first. In that interim period when youâre getting loads of attention and you canât help getting over-excited. But you quickly learn to control yourself - it's a matter of necessity - and several of them have told me that the constraint is actually the source of a sort of sexual high, a sustained sexual excitement thatâs almost like being on drugs! Especially in social situations like parties or clubs. It becomes addictive. Thereâs no pressure to perform. The pleasure just fills your whole body.â
Tim shivered. He could almost imagine it. But he wanted desperately to see what it really felt like.
âSo, Tim⊠Do you think itâs something you might want to experience one day?â
âI⊠Maybe⊠I would like to look as attractive as themâŠâ
âHmm. Suppose they were girls and not boysâŠâ
âNo⊠I like the fact theyâre boys⊠Itâs somehow sexierâŠâ
âAhaâŠinterestingâŠâ She patted his cheek. âI think you should try⊠You may surprise yourselfâŠâ
Tim didnât reply, but bit his lower lip again. He was aware he had an erection which wouldnât subside. Maria could see it out of the corner of her eye, stretching the latex panties she had given him. But she said nothing.
âI wonder if⊠These photosâŠâ
âIâll send them to you, Tim. No probs. They may help you to decide. If you do, tell me or Connie or Cassandra. Iâm sure theyâll be able to accommodate you. In my opinion youâd make a perfect femboy.
Tim nodded.
Someone was knocking at the teashop window.
âI bet thatâs them. Theyâre early. Stay here. Iâll go see.â
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Today at 06:49:38 AM »
Maria smiled knowingly. âOkay. This me with Rochelle, aka Rory. That isnât his real hair. God knows how long it would have taken to grow it that long â he always wore it cropped. You can see how happy she is as a femboy. Rory was a bit of a tearaway when he was a boy. You can still see the mischief in her face, right? Tim?â
Tim was staring. His mind was in a ferment. That girl â that guy â was drop-dead gorgeous. Just looking at her picture he felt attracted to her in a weirdly intense way. But she was really a boy! Maybe⊠Could that be the reason? It was very disconcertingâŠ
âAre you all right? You look pale. Here, letâs get that gag off so you can breathe.â
She unbuckled one side of his ball-gag. What a relief! His jaw ached, but he could speak and breathe.
âTh-thanks, MariaâŠâ
âConnie made me promise not to, but in any case I need to know what you think. Does that feel better?â
âYeah⊠Much. Thanks.â He exercised his jaw. âCan I⊠Can I see, er, Rochelle again?â
âHereâŠâ
He couldnât get over it. He swallowed, and bit his lip. He pretended to be unaffected.
âYeah, heâs really very good-looking. I âspect he was already pretty cute. Itâs not something I could ever achieveâŠâ
Maria had a knowing smile on her face. She knew he was really gobsmacked â turned upside-down in fact.
âNo, he was very ordinary. He had some minor facial surgery, purely to slim out his nose a little. But you have a lovely cute nose, Tim. All youâd need is a really good makeover by someone who really knows their stuff. The figure we shaped using a very fine light corset, and then enhanced it with these pretty cinched dresses. Here. let me show you another Iâm particularly proud of. Paul. He was such a sulky boy. He took loads of persuading. But in the end he went for it. He even had some minor breast enhancement, at his own request. But he definitely preferred boys, and once he was finished he really came into his element. From that moment on he was happy and carefree. Yes. Pauline. Here he is.â
She held up the phone. Tim did a double-take.
âThatâs a⊠ThatâsâŠPaul? Pauline, I mean?â
âYes. So cute, donât you think?â
Tim was speechless. âPaulâ looked like the sort of girl he turn somersaults for. His mouth was dry and his heart fluttering. This was crazy⊠Why did these boys affect him so much? And why did heâŠif he couldnât have themâŠthen, want to be like them? He felt slightly faint. Maria perceived this, stood up, and helped him into the chair. She had no idea he was going to be so deeply affected. But she was delighted he was.
âS-sorry, Maria⊠Iâve been standing for so longâŠâ
âOf course, dear. I apologise. I should have realised. Just rest there as long as you like.â
âThank you.â He paused. âAre there, erâŠany moreâŠ?â
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Yesterday at 06:53:17 PM »
Maria closed an hour early that day. It meant she missed the after school trade, but she had a reason.
âGwen? Can you tidy up for me? I need to have a chat with Tim here. Tim, follow me.â
She led him into what appeared to be the stockroom. She sat down in a chair and beckoned him to stand before her.
âI want to talk to you about something Tim. Something you may not think about enough yourself. Your future.â Tim looked puzzled. He made a questioning âmm?â
âIt wasnât a whim that Connie brought you here today. I asked her to. We go back a long way. I used to work for ESDS, and then the teashop became available, and I had to make a decision. In the end I plumped for the teashop. Iâd always fancied running a place like this â I started off in catering â and much as I regretted leaving Cassandra and the others, I think it was the right thing to do. When I first saw your photos I knew I had to get to meet you. You see, I had a particular role at ESDS. I was the femboy trainer. Do you know what that is? I mean, do you know what a femboy is? A real femboy, not just a pretty guy in a dress?â
Tim shook his head.
âIâll explain. A real femboy is a boy who most people would immediately take to be a girl â not just any girl, but an eye-catchingly, head-turningly pretty girl. When I saw you, I wished I could be back at ESDS, helping you, training you, to be a femboy. Because believe me, you would make a great one. And Iâm pretty sure you would love it.â
Tim frowned, and shook his head doubtfully.
âHear me out. I know all about your pageboy antics. You wouldnât have to abandon that project. But if you had the training to be a femboy I believe you could find true satisfaction. A good femboy â and you would be a good one â appeals to everyone. Not only do women find them fascinating, but men as well. For women, especially the young generation, who find the traditional macho types simply boring, the idea of a young man confident enough to present as a girl, sensitive enough to understand the allure of female clothing, and sensual enough to enjoy the amalgam of male and female sexuality, is exciting and incredibly sexy. For men, physical attractiveness is the immediate turn-on. But when they realise that the object of their desire is actually male, well⊠There may be a moment or two of confusion, but once aroused, a manâs sexual attraction cannot easily be suppressed. Moreover most men have in their psyches an element of homosexuality. Most will deny this, but it remains true, whether from the love of male comradeship or the underlying fear of women. So chuck that into the mix and theyâre hooked! The very reason a femboy is so devastatingly attractive is that element of maleness in his looks which adds a spice to the female allure. For a male it is incredibly powerful. The femboyâs looks allow them the perfect excuse to flirt, the male element, when subtly present, breaks down all psychological and social barriers. But it also acts as a protection, since the man is still slightly hesitant, still daunted, still embarrassed. That why the femboy is the most powerful of all sexual beings.â
Tim was staring at Maria now, though his eyes were unfocussed, as the possibilities began to take shape in his imagination. To be the fantasy of both sexes! Women and men⊠Would Bobby like him as a femboy? He liked him as a boy, but⊠But how could he be more feminine than, say, he was at the present?
Maria must have been reading his mind.
âJust wearing a pretty latex dress doesnât make you a femboy. Here, let me show you.â
She picked up her phone, scrolled through the gallery, and finally found what she was looking for.
âFor example, this boy, Carl, was one of my first projects. This is what he looked like after Iâd finished with him. We named him Caroline. I was so excited. So was heâŠâ
She held up her phone for him to see. His eyes widened. If he hadnât been firmly ball-gagged, he would have gaped as well.
âThatâs a boy?â he thought. He experienced an involuntary thrill of excitement. Really? Heâs so fuc-king beautifulâŠ
âLike to see some others?â
He nodded â a little too eagerly â and immediately blushed.
Active Sissy Stories / Re: His Aunt Nicole
« Last post by RibbonBound on Yesterday at 12:20:11 PM »
Thanks again for such a lovely story!
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Yesterday at 07:35:38 AM »
Unfortunately for Tim, very few were that kind. He very soon discovered that almost no-one who received a voucher â and that was everyone â could resist demanding, or often helping themselves to, a peep at his panties. Worse, they would then give the voucher away to some curious passer-by! Of the passers-by who stopped to gawp and snigger, the teenage girls were the worst. They arrived in pairs or threes, and would stand there whispering and pointing and giggling, taking pictures, reading the notice-board out loud, and hanging around to see the fun.
âPopsi the pervert!â said one to her friend in a loud whisper, pointing at him. And the friend collapsed in laughter.
He tried to protest, but the muffled noises that emanated from behind his ball-gag only generated more hilarity. In any case, it didnât make any difference at all. Soon a little knot of females had gathered, chattering and giggling amongst themselves, and waiting for the next customer to leave and demand her bonus. At lunchtime the cafĂ© became really busy, and his skirt was up and down like a yoyo. Worse, there was an influx of sixth-formers from the local school, St. Catherineâs, who were surprised and delighted to find such an unexpected source of entertainment, and many of whom wanted to be photographed alongside him or take selfies. One group of four took it in turns to have their photos taken by their friends. The last, a blonde, hung onto him arm while the others snapped away.
âWait till we show these to the others!â cried one, delightedly.
The blonde had a better idea.
âWait till I show Dave a picture of me with my new girlfriend. Heâs gonna be so jealous!â
And she burst out laughing.
âSeriously, though, he must be a real pervert to do this,â returned another. âI mean, all in rubber with a ball-gag and everything⊠Are you, boy? Am I right? Do you enjoy doing this?â
Blonde rejoined her friends. âJust nod if you do. We wonât judge you. I think itâs coolâŠâ
But all Tim could do was to frown, and hope they went away. He was saved from further humiliation by the appearance of Maria, who had noticed the four girls hanging around and had come out to check on him.â
âYou all right, Tim?â
He nodded.
âTim? Is that his name?â asked the cheeky blonde.
âThatâs right.â
âWhyâs heâŠyou knowâŠ?â
Maria smiled indulgently. âTimâs in training as a professional domestic. He also models. Heâs held in very high regard by his employers. Here, take a leaflet. Theyâre called ESDS. Your mothers may be interested in using their services. Tim is already a fully-trained maid, and a top-class pageboy. Right, Tim?â
Tim nodded, still blushing.
The girls each took a leaflet, more delighted than ever.
âThatâs so cool!â cried one, scanning the leaflet. âOh my god, mumâs gonna flip out when she sees this!â
âYeah,â remarked her friend. âYour mum loves her toy boys, doesnât sheâŠ?â
âShut up, Fiona! None of your beeswax what my mum doesâŠâ
âAre you coming in girls? Timâs going to have a break from leafletting now. He can wait on you if you likeâŠâ
âYes, Maria, pleaseâŠ!â
So while the girls trooped in, Maria unlocked Tim. He went to the toilet, washed, and grabbed a sandwich before helping Gwen with waitressing. The girls were dying to ask him questions, but Maria loyally refused to remove his gag. But they pestered her so much that to shut them up she eventually showed them photos which Connie had sent her of some of his other outfits.
âYou can see how versatile he isâŠâ
âI love the pageboy outfit he wore to the weddingâŠâ sighed blonde, whose name was Hanna. âCan you send me that one?â
âWellâŠâ
âPleaseâŠâ
âI suppose it wonât do any harm. Most of these are fairly public already. And if itâll help persuade your mothers to use ESDSâŠâ
âDefinitely, Maria!â
âOkay, thenâŠâ
Tim, busy serving the other tables, couldnât see what Maria was sharing, but the prospect of his private photos being circulated around the local girlsâ school was not reassuring. But there was no way of protesting. So he swallowed his anxiety and got on with his work.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by Party Dress on Yesterday at 07:01:59 AM »
Please include AI photos of each! I really enjoy your use of AI to paint the picture
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on September 07, 2026, 12:59:21 PM »
At this point, Aunt Patricia's version of âonly lookingâ had transformed into intense shopping. Edward glumly realized the collection of dresses and accessories set aside for purchase seemed to multiply every time he looked! Aunt Patriciaâs decisions had come quickly and often. Of course, the dainty blue dress was the first to be chosen. It was a delicate, vintage-inspired powder-blue party dress with a rounded Peter Pan collar made of white eyelet lace. The fitted bodice was gaily decorated with tiny white embroidered flowers scattered across the fabric, and the short, sleeves puffed demurely at the shoulders. The white satin sash had a prissy little bow in front, and the hem was an intricate scalloped lace trim.
Edward soon learned the first clerk was named Sabrina, and she suggested a lovely mint-green lawn dress made of crisp taffeta. It was light and airy with a tea-length skirt, and the fabric had a faint sheen. It had charming pearl buttons which contrasted sweetly with the green material. A narrow band of white embroidery traced the rounded collar and continued neatly around the cuffs. It looked ready-made for a formal garden party.
When Edward was buttoned into it, Sabrina gave an approving look. âOh, that shade is beautiful on him,â she said, âIt makes his eyes look softer, and the cut gives him such a graceful line.â
Edward was hyper-aware of how the taffeta made a rustling little sound whenever he moved.
Aunt Patricia gave a pleased little nod. âExactly what I hoped,â she replied, âdemure and wonderfully becoming.â
Aunt Patricia became enthralled with the soft lavender frock as soon as she saw him in it. It had an almost fairy-tale delicacy. The pale lavender fabric shimmered over a satin lining, with a Peter Pan collar and a wide, darker lavender sash that gathered in back into a large butterfly bow. Sheer organza softened the bodice and skirt in floating overlays, with airy ruffles at the sleeves and a translucent flounce that caught the light whenever Edward moved. The skirt was embroidered near the hem with adorable lavender violets that seemed to dance with every step. Sabrina found a lovely pair of pale blush, peep-toe sandals that went perfectly with it. They had a low heel, dainty toe and ankle straps, and delicate lavender floral applique flowers on top.
âNow that one,â Aunt Patricia commented with approval, âis exquisite. Turn slowly, darling.â
Edward made a small, reluctant turn, and the organza floated around him. The unfamiliar heels tipped his weight forward, making him wobble slightly and forcing him into short, careful steps. He was not used to shoes that demanded so much attention. Meanwhile, with every tiny movement, the sheer organza layers brushed and tickled across his shoulders, almost like cobwebs. He fought the urge to shrug them away, gave an involuntary shudder, and then lifted a hand to brush at the delicate fabric.
Aunt Patricia noticed both the wobble and his reaction to the organza at once. Her expression softened into amusement. âOh, donât fuss with it, darling,â she said, reaching out to smooth one translucent ruffle with the back of her fingers. âThose fluttery sleeves are part of the charm.â
Edward swallowed. âIt tickles, Aunty,â he admitted in a small voice, âmaybe I could try something a little less⊠floaty?â
Aunt Patricia gave a fond little laugh. âLess floaty? My dear, the âfloatinessâ is precisely the point.â Then, she couldnât help but add, âand as for the sandals, Iâm sure youâll get used to them in no time⊠Practice makes perfect!â
Edwardâs mouth pinched into a helpless grimace at that, the corners drawing tight. The promise of "practice" in girls heels was not comforting. Aunt Patricia caught the look immediately and chuckled lightly. To her, his discomfort only proved that the dress and shoes were doing exactly what she wanted: making her nephew aware of every soft, girlish detail.
âI adore this one too,â Sabrina interjected approvingly. âIt makes him look so delicate, and the sash keeps it polished.â
By now, Edward had found out the second clerk was named Skye. Skye added, âAnd I love those sandals!â Edward looked down at the little floral appliques on the sandals and blushed.
Patriciaâs face warmed with triumph. âYes,â she said simply as she patted Edwardâs arm with fond authority, âof course, weâll take the dress and the shoes.â
Then, Skye brought out a charming pink and white floral print sundress that was, she said with a warm smile, âa perfect summertime frock for someone who looks this darling in pink.â It was made of lined cotton, and the white background was scattered with pink roses and pale green leaves. Narrow shoulder straps tied into dainty bows, and the bodice was gently smocked across the front with tiny rows of pink stitching that gave it an especially youthful look. A large flounce circled the hem so that the skirt bounced and swayed around Edwardâs knees as he moved.
Skye held the skirt out so Aunt Patricia could see the shape better, âthis one has a sweet, old-fashioned charm.â
Sabrina nodded from beside the mirror, âVery pretty, very light.â
Aunt Patricia looked delighted.
Sabrina then had an inspiration and showed Aunt Patricia a sage green chiffon dress from the storeroom that had not even been put on the rack yet. Aunt Patricia eagerly snapped it up as soon as she saw him in it. It was a sleeveless, halter top, A-line dress made of delicately layered chiffon with a subtle floral print, and it rustled delightfully with Edwardâs every movement.
âOh, that one makes him look like a little summer postcard,â Sabrina said kindly, though the sparkle in her eyes made it feel faintly teasing.
Next, Aunt Patricia fell in love with a âtwirl-worthyâ satin formal dress that came in several colors. The A-line creation had a sweetly pleated bodice and wide, gently gathered shoulder straps that sat gracefully across the upper arms. The ruching across the bust and torso added subtle texture while keeping an elegant look. A cleanly defined waistband separated the fitted bodice from the skirt.
âThat looks precious on him,â Skye added helpfully, âitâs such a classic, princess-inspired look!â
"Princess-inspired?" Edward asked hesitantly. He winced as he realized how sissyish the words sounded.
"Oh yes, sweetie," Skye said cheerfully, "just like something out of a storybook!"
After having Edward stand in front of the mirror wearing the same dress in several colors, Aunt Patricia just couldnât decide which she liked best. In the end, she decided to get one each in candy pink and orchid purple.
âWhy choose,â she said brightly, âwhen Aunty can get her princess both?â
Edward reddened cutely again at being called a princess, but he went still as he thought about the word âboth.â It was such a small word, tossed out with Aunt Patriciaâs bright little smile, but it landed with a weight. âBothâ meant plenty of options for his auntâs future plans. It meant pretty dresses waiting for many future occasions and events. He felt the figurative ground shift under his feet, suddenly tilting toward a future of drawers and closets full of satin and lace.
He looked at himself in the mirror dejectedly and tried to remind himself he was a boy. The candy pink dress shone softly under the store lights, and its wide straps rested delicately along his upper arms, making his shoulders look small and narrow. The pink color softened his face sweetly. He felt so fragile, polished and painfully pretty as he stared at his reflection.
He knew he was a boy, But Aunt Patricia seemed to treat that fact as a minor inconvenience to be hidden, managed and eventually⊠forgotten. Sabrina and Skye smiled, Aunt Patricia glowed and the mirror told the harsh truth. He looked nothing like a boy now. He felt more uncomfortable stirring in his panties.
Finally, there was an apricot and cream party dress scattered with small satin rosettes, which Aunt Patricia declared âtoo adorable to leave behind.â She insisted on seeing it on him paired with some accessories, already speaking as if the decision had been made. To Edward, it seemed as though having him put it on was merely a formality.
âIt should be worn with a petticoat, I think,â Aunt Patricia said, eyes bright, âand perhaps if you have some ivory shoes to match?â
Sabrina brightened at once. âOf course, maâam. I think I know just the thing!â
âYes, please see to it, my dear,â Aunt Patricia agreed. With a pleased smile, she took a seat on a cushioned armchair.
As Sabrina ushered Edward back to the fitting room for what felt like the hundredth time, she carried the apricot and cream dress on a padded hanger. Edward glanced back at Aunt Patricia, and the satisfied look on her face made him worry what else she had already imagined for him. How many more little decisions had already been made? Her calm, triumphant smile seemed to say it all.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by BabyJay on September 07, 2026, 10:18:28 AM »
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on September 05, 2026, 04:44:27 PM »
Morgan & Tateâs was a vast department store full of polished counters, brass rails, mirrored columns and ladies in stylish attire. Edward felt completely self-conscious as Aunt Patricia shepherded him directly to the girlsâ department, then swept past the first displays of casual fashions without so much as slowing. He tried to console himself that Aunt Patricia had earlier left open the slim possibility that they might âjust look,â but that seemed less likely with each step.
Racks of casual skirts and fashion tee shirts stood near the aisle, but Aunt Patricia gave them only a dismissive glance. âNo, no, dear,â she said, steering him briskly onward. âThose are not what we are here for. We need proper attire worthy of the occasion.â She bypassed the everyday clothing entirely and headed straight toward the section with the more formal and fancy selections, where shoes, hair ribbons and racks of elaborate dresses were arranged by color like precious flowers.
Edward felt his stomach jump as he realized Aunt Patricia had not even considered lingering among the somewhat plainer clothes. Each step made him feel more conspicuous, as if everyone had turned to watch him be led deeper into Aunt Patriciaâs idea of what he ought to become. He kept his eyes lowered, cheeks hot.
Aunt Patricia took note of his uneasy demeanor and chided him with a trace of amusement, âCome along, dear, we need not make a production of it!â Then, she got the attention of a nearby saleswoman and immediately began to make a production of it. She jumped right in and announced to the clerk, âWe are here to upgrade my nephewâs wardrobe. He is engaged in a very special and unique project which I am thrilled to support. Please show us some classic and refined dresses and accessories to complement his unusually fine features.â
Edward instantly understood with a helpless little twist of dread that there would be no pretense of âjust lookingâ today. Edward blushed brightly as the clerk learned he was in fact a sissified boy in a pink dress. He wanted to crawl into a hole, but there was no escape.
âAunty⊠pleaseâŠâ he almost whimpered.
âWhat troubles you dear? I am merely being precise,â she replied. As she spoke, she flashed a subtle warning look at him for his mild impertinence. She was in no mood to be denied.
Edward gulped helplessly but remained silent. His aunt had no intentions of holding back today.
The salesclerk gawked at them for a split second. Edward could see the wordless question on her lips, âNephew?â But she didnât voice it and recovered almost instantly. She then appraised Edward with a calm sense of professional cheer, which was somehow worse than curiosity. âWe have some nice items on sale today that might interest you,â the clerk began.
Before she could continue, however, Aunt Patricia gently cut her off, as if explaining something that ought to be obvious, âI am less interested in price tags than quality, my dear.â She looked at Edward with an expectant look and added cheerfully, âwe are not here to cut corners today. Please bear that in mind.â
âOf course, Maâam, right away!â the clerk responded eagerly. Realizing this was actually a boy standing before her in an adorably sweet dress, she sized the situation up rapidly. She broke into a knowing smile as she began selecting dresses from the racks. Whatever questions she may have had were more than offset by the generous commission she sensed was there for the taking. One look at Aunt Patriciaâs expensive clothing and a quick assessment of her feminized charge made it an obvious decision to put her curiosity aside.
Blanching, Edward understood Aunt Patricia had not dragged him here merely to browse or even just pick up only an item or two. She had come armed with money, determination and a vision that she meant to make real before the afternoon was over.
The afternoon soon proved exhausting in a way Edward had not known shopping could be. The clerk was surprised and then amused to discover he was laced into a snug little corset. âThat explains your lovely posture, doesnât it?â she teased kindly.
Again and again, Edward was ushered into the elegantly feminine fitting room with cream accents, plush carpet and a large three-way mirror. It seemed to Edward that as soon as he stepped out of one frock he was guided immediately into the next. Delicate and girlish fabrics slid repeatedly over his arms, legs and chest⊠slippery satins, tickling lace, and scratchy organza. Button after button, the fabrics gathered quietly around him. First, a pale blue dress drew neatly around his waist. Next, a lavender one settled with a hushed, powdery rustle. Later, a floral sundress brushed his knees in a breezy circle.
With each dress, Edwardâs feelings grew more on edge. He was embarrassed at the attention, and he was dejected to realize that this is how much of his summer vacation would undoubtably go. His aunt wasnât buying all these clothes to hang unworn in his closet. He was a teenage boy, but he was aware that there was vanishingly little visible evidence of that now. His cheeks stayed hot almost constantly, and his stomach fluttered whenever he had to step out of the dressing room to show the next dress. More than once, he felt an excited tingling and tension in his frilly panties as the salesclerk zipped or buttoned him into yet another frock for his aunt's inspection.
Aunt Patriciaâs enthusiasm seemed to grow with each new reveal. âOh, that color is charming on him,â she said when he emerged in the pale blue dress. âThe white sash is perfect⊠It will be lovely with some lace anklets and perhaps a nice barrette to bring out the color.â Then she directed, âEdward, stand up straight so we can see the line properly. Good. Now be still, hands at your sides.â
Edward blushed but did his best to comply with his auntâs instructions. She eyed his outfit up and down and tugged gently to arrange his skirt.
âThere,â she continued, âNow letâs see you move back and forth a bit so we can see how it follows you, dear.â When he stepped forward, she immediately corrected him, âsmall steps, sweetie. Move gracefully⊠you are not a lumberjack! Draw on that same 'feminine stillness' you display for Miss Vale.â
Edward cringed again. Everything seemed to come back to that portrait.
The salesclerk watched this exchange with interest. Then, she added helpfully. âTurn around, sweetheart. Let us see the back.â Edward obeyed with a stiff little pivot, and the skirt whispered around his knees.
The clerkâs professional smile grew warmer with every new item she brought out, partly because she saw her commission growing by the moment. She also quickly realized that Aunt Patricia was completely uninterested in casual attire for her nephew. When she brought out a cute everyday top and skirt, for example, they were immediately rejected out of hand. It wasnât long before she enlisted a second clerk to help with this very particular pair of customers, and they began bringing out the frilliest and most adorably girlish items in the store.
Outside the fitting room, Aunt Patricia appraised each new dress with discerning satisfaction. She continued to dismiss anything that looked too plain or ordinary. The clerks remained professional, yet curiosity glimmered behind their smiles. Other customers could not help overhearing Aunt Patriciaâs clear references to âEdward,â âmy nephew,â and âhim.â Each time, Edward felt newly exposed. He stood in dress after dress while glances flickered toward him, paused, and politely moved away. As the afternoon dragged on, the fitting-room carpet seemed endless beneath his Mary Janes.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on September 04, 2026, 04:12:02 PM »
Thanks for the suggestions and comments.
The more you give, the more I can give back.
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