Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on Today at 04:44:27 PM »
Morgan & Tate’s 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 girls’ 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 “just look,” 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. “No, no, dear,” she said, steering him briskly onward. “Those are not what we are here for. We need proper attire worthy of the occasion.” 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 Patricia’s 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, “Come along, dear, we need not make a production of it!” 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, “We are here to upgrade my nephew’s 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.”
Edward instantly understood with a helpless little twist of dread that there would be no pretense of “just looking” 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.
“Aunty… please…” he almost whimpered.
“What troubles you dear? I am merely being precise,” 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, “Nephew?” But she didn’t voice it and recovered almost instantly. She then appraised Edward with a calm sense of professional cheer, which was somehow worse than curiosity. “We have some nice items on sale today that might interest you,” the clerk began.
Before she could continue, however, Aunt Patricia gently cut her off, as if explaining something that ought to be obvious, “I am less interested in price tags than quality, my dear.” She looked at Edward with an expectant look and added cheerfully, “we are not here to cut corners today. Please bear that in mind.”
“Of course, Ma’am, right away!” 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 Patricia’s 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. “That explains your lovely posture, doesn’t it?” 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, Edward’s 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 wasn’t 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 Patricia’s enthusiasm seemed to grow with each new reveal. “Oh, that color is charming on him,” she said when he emerged in the pale blue dress. “The white sash is perfect… It will be lovely with some lace anklets and perhaps a nice barrette to bring out the color.” Then she directed, “Edward, stand up straight so we can see the line properly. Good. Now be still, hands at your sides.”
Edward blushed but did his best to comply with his aunt’s instructions. She eyed his outfit up and down and tugged gently to arrange his skirt.
“There,” she continued, “Now let’s see you move back and forth a bit so we can see how it follows you, dear.” When he stepped forward, she immediately corrected him, “small steps, sweetie. Move gracefully… you are not a lumberjack! Draw on that same 'feminine stillness' you display for Miss Vale.”
Edward cringed again. Everything seemed to come back to that portrait.
The salesclerk watched this exchange with interest. Then, she added helpfully. “Turn around, sweetheart. Let us see the back.” Edward obeyed with a stiff little pivot, and the skirt whispered around his knees.
The clerk’s 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 wasn’t 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 Patricia’s clear references to “Edward,” “my nephew,” and “him.” 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 Yesterday at 04:12:02 PM »
Thanks for the suggestions and comments.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on Yesterday at 01:27:42 PM »
The following Monday, as Edward started the first full week of summer break, he found himself on the way to a piano lesson. After some discussion between his mother and aunt on Saturday while he had been practicing scales, it was agreed that he should not abandon his lessons because of the demands of the portrait. Instead, his music lessons were simply reshuffled into the new order of things. With his new schedule, his piano teacher, Mrs. Baxter, had agreed to move his lessons to Monday and Thursday mornings for the time being.
Aunt Patricia had of course weighed in. She thought this was another delightful opportunity for Edward to get used to his dresses, and she even offered to take him to the lessons so Marian might have some quiet mornings at home. Aunt Patricia took it upon herself to call Mrs. Baxter and explain the situation in advance. She even relayed how darling Edward had been in his lacy yellow party dress while playing scales on Saturday. When she brought him to his lesson on Monday morning, he was nattily dressed in his pretty pink frock, frilly white anklets and black Mary Janes. His shiny pink hair ribbon was tied neatly in place, and Edward felt the snug embrace of his ever-present corset hugging tightly underneath.
Mrs. Baxter greeted Aunt Patricia quite calmly and set Edwrda’s lesson book on the stand as if nothing about the morning was unusual. Edward sat down very stiffly on the piano bench, very self-conscious of his frilly pink panties and mindful of his confining corset. He was careful to arrange his skirt demurely at his aunt’s prodding.
Only after setting up the sheet music did Mrs. Baxter comment on his attire. She blinked over the rim of her spectacles, first at Aunt Patricia and then at Edward, who wished the piano bench might swallow him whole. “Well,” she said after a small pause, “that is a very lovely dress. Did you pick it out yourself, Edward?”
“Uhh, no Mrs. Baxter,” Edward said quietly, “My Aunt… Aunty Patricia gave it to me.”
Aunt Patricia practically beamed at that.
“It’s… it’s for the portrait,” he explained reluctantly.
“So I understand,” Mrs. Baxter replied, settling herself beside him tactfully, “It is certainly a charming gift, and that pink seems to suit you.”
“Thank you,” Edward muttered meekly. He swallowed hard and felt his cheeks warm.
Aunt Patricia couldn’t resist piping in with a pleased look, “that’s exactly what I thought when I saw it too.” She added, “his Aunty knew he would be adorable in it!”
With that, Mrs. Baxter moved into the lesson, “Now let’s get our wrists level and shoulders relaxed.”
As he placed his fingers on the keys, a glum thought returned to him. This was his summer vacation, the long free stretch he had spent months waiting for. Yet piece by piece it was now being claimed by the portrait. It seemed his whole holiday was turning into one long, suffocating sitting.
Mrs. Baxter adjusted quickly, “Now, middle C.”
Wearing a dress to piano changed the feel of the lesson in ways Edward could not ignore. The bench seemed narrower when he had to arrange a skirt over it. The pedals felt farther away when he was conscious of his frilly anklets and Mary Janes.
Still, once his hands found the familiar pattern of the piece they were working on, he was distracted a bit. For the forty minutes or so, he was not exactly free from the portrait, but he was able to think of something else. Still, seeing his pink-polished nails dance over the black and white piano keys made him feel even more docile and girlish if he pondered it too long. It was better to focus on the music.
When his lesson ended, Aunt Patricia guided her nephew back to her car. Edward had murmured goodbye to Mrs. Baxter as he felt propelled along by his aunt for the short ride home. He didn’t have anything else planned until his next sitting tomorrow, and he was hopeful his aunt would be done with him for the day. It seemed, however, that she already had something else on her mind, and Edward began to fret silently. Her body language was just too… purposeful.
No sooner had they entered the front door than Aunt Patricia turned to her sister with that bright, insistent expression Edward had already learned to dread. “Marian, to continue our conversation from the other day, we really must be practical,” she said, as if the matter had already been decided and only needed to be announced. “Edward simply cannot manage with only these two dresses, not with his sittings and appointments and lessons. He needs some more things, and we ought not put it off any longer.”
Marian opened her mouth as if to suggest that the matter could wait, but Aunt Patricia lifted her hand in a soft refusal. “No, Marian, truly, I insist.” Then, she announced with an eager look, “I’ll take him to Morgan & Tate’s this afternoon at least to look if nothing else.” She looked at Edward with a beaming smile, “and you, my darling, needn’t worry your pretty little head about any of it. Your Aunty has made up her mind.”
Edward knew Morgan & Tate’s was the fanciest department store in town. It was in the same shopping center where they had gone to lunch on Saturday. Any hope Edward had of escaping the for rest of the day vanished, and all his worries about an “expanded wardrobe” now proved well-founded. The first pink dress had been humiliating enough when it was only part of Miss Vale’s recommendations, almost a uniform for entering the world of the portrait. The second yellow dress, Aunt Patricia’s “gift,” had raised the stakes. Standing near the staircase in his pink frock and frilly anklets, Edward now felt trapped.
His mother gave a sympathetic smile, but she soon acceded to her sister’s wishes. “Go with your aunt, Edward. It may be pleasant for you two to spend some more time together away from the studio.” It seemed she was trying to put the best spin on things. The hint of disagreement she had displayed on Saturday was nowhere to be found today.
“You needn’t look so solemn,” Aunt Patricia assured him, “Just follow Aunty’s lead. Aunty knows exactly what to do, and it’s going to be such fun!”
“Fun for who, exactly?” Edward thought glumly. “Isn’t looking… how shopping begins, Aunty?” he asked rather weakly.
“Precisely, sweetie!” Aunt Patricia replied, pleased by his grasp of procedure and easily turning his timid objection into agreement. And off they went. She seemed to be in an almost jovial mood. With Marian staying behind, it would be just the two of them this afternoon, and that seemed to make Aunt Patricia’s manner even more overbearing and insistent, perhaps even unfettered.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by Party Dress on Yesterday at 01:12:21 AM »
I wonder if Edward will ask his Aunt to stop calling him Edward in public and ask for a girl's name instead to stop drawing attention to the fact he is a boy. His Aunt will then stick to it, constantly reminding him he asked for this
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on September 02, 2026, 08:01:38 PM »
By the time the plates were cleared and Aunt Patricia had decided there was no need for dessert, Edward had grown almost hopeful again. Their lunch was nearly over. His mother reached for her handbag, and Edward sat up straighter, eager for a short walk back to the car and then the blessed privacy waiting at home.
Aunt Patricia, however, had other ideas. “While we are out,” she said, rising with an air of pleasant decision, “we ought to look at the shops… Just some window shopping.”
Edward’s spirits deflated. He followed because there was no other choice, keeping close to his mother. Aunt Patricia moved at a leisurely pace down the sidewalk, pausing now and then before the various window displays.
Soon they passed a bridal shop, and she stopped in front. The window was filled with pale satin, lace, and gauzy little clouds of tulle. Bridesmaid dresses in soft pinks and blues stood on slender forms, while petite flower girl dresses were arranged near the front with sashes tied into enormous bows. Aunt Patricia appeared delighted. “Oh, Marian, look at these,” she breathed. “Aren’t they simply precious?”
Edward cringed.
Aunt Patricia leaned nearer the glass, “Such pretty bridesmaid dresses, and look at those precious little flower girl frocks.” She smiled at her befrocked nephew, “Aren’t they adorable, Edward? Do you see anything you’d like to try on?”
“Aunty,” Edward whispered, pleading. His face warmed all over again. He dared not look at the window too directly, afraid that any glance might be taken as interest. “No... thank you.” The suddenly real thought of being taken inside the shop to be fitted in pale satin and tulle made his stomach twist.
Aunt Patricia seemed not to hear his refusal. She pointed through the glass at one dress in particular, a delicately pale pink flower girl dress with tiny sleeves, a satin sash, and a tea-length skirt that fell in soft, careful layers. “That one, I think,” she mused, smiling at the display as if already imagining it. “Something pale and sweet like that would be lovely on you, sweetie. You would make such a charming little flower girl.”
She warmed to the vision at once. “Can’t you just picture it, Marian?” she said. “Our little Edward all daintily dolled in that satin confection, with that sash tied beautifully at his back and a lovely spray of flowers tucked into those curls. He would be absolutely darling!” She looked at him with open delight.
Edward felt a new wave of embarrassment wash over him as she spoke. “A flower girl?” he thought with a wince. He imagined having to walk solemnly down an aisle decked out in pale pink satin while everyone turned to gawk at him. Aunt Patricia’s earlier remarks about expanding his wardrobe flooded back into his brain with dreadful clarity. She had spoken as if more dresses were not a temporary excursion, but rather a sensible next step for him. The pink flower girl dress was not an idle fancy, he realized. She had not let the idea go at all. He was certain his face must be as pink as the dress in the window. Dressed as he was, it was not hard to imagine how the tiny sleeves of the flower girl dress might gather at his shoulders and how the skirt would flutter merrily as he walked. “Please don’t… Aunty,” he whispered, so softly it was almost not a voice.
What unsettled him most was the way Aunt Patricia kept returning to this idea with such calm certainty. Edward got the distinct sense that she was merely biding her time.
Marian, who had been studying the window display with a measured expression, gave a small shake of her head. “But, Patricia, it really wouldn’t be practical, would it?” she questioned gently. “Edward isn’t scheduled to be in any weddings, so it would just hang in the closet.”
Aunt Patricia turned from the window with a soft, indulgent smile. Edward’s consternation did not seem to trouble her at all. “Well, perhaps you are right,” she said. “Still, I can’t imagine it would be difficult at all to find occasions for him to enjoy it. Sometimes it is a joy to dress up for no reason at all beyond wanting to feel precious and pretty! Maybe...” She let that thought hover uncertainly for a moment, neither withdrawing the idea nor pressing it further.
“It’s a shame he hasn’t had an opportunity to be a flower girl… at least not yet,” she mused mischievously. She giggled and added, “he would look lovely in it I’m sure, but there might always be another time.” Her words landed with a gracious little pause, as if generously allowing her sister to believe she had prevailed for once. But from Edward’s perspective, it felt like Aunt Patricia was merely playing a game.
His mother’s objection had sounded sensible, even protective, and for one foolish heartbeat Edward had wanted to be grateful for it. But Aunt Patricia’s smile spoiled that comfort. Marian’s momentary firmness seemed like something Aunt Patricia had permitted for her own amusement, a small rebellion allowed because it cost her nothing. In the end, it seemed, the final decisions would still belong to Aunt Patricia.
At that moment, movement across the street caught Edward’s eye. He was immediately distracted. Tommy and Ben were passing by again on the opposite side. Both boys slowed, and once more their attention lingered on him a little longer than it should have.
Edward went beet-red. He turned back toward the bridal-shop window as if the reflection might hide him, but the move only gave him a reflection of himself in the glass. He could see a translucent image of his prettily curled hair, his frilly yellow party dress and a mortified expression.
Aunt Patricia noticed at once. She followed his gaze and smiled brightly. “Why, Edward, there are your friends again,” she said, using his name with dreadful clarity.
Edward winced before he could stop himself. Had they heard his aunt? Surely other noises must have drowned out his name. He saw in the reflection that Tommy’s head tilted a fraction, and Ben glanced in their direction. Edward’s stomach tightened with a fresh twist of uncertainty. Thankfully, they kept moving in the opposite direction and turned a corner out of sight.
Again, he told himself they might not have known. But seeing them this second time made that hope thinner than before. If they had wondered at lunch, surely now they would wonder even more. And if they had heard Aunt Patricia say his name, even from across the street, then perhaps there was no wondering left at all.
The drive home passed in an uncomfortable silence. As they pulled into the driveway, Edward longed to just go straight upstairs, close his bedroom door, and change out of these clothes. He could almost feel the relief. The thought carried him through the front door.
But it turned out Aunt Patricia was in no hurry. She seemed to settle in for a pleasant visit and drifted into the sitting room with the serene expectation that everyone else would follow. Edward hovered near the staircase for one hopeful second, but Patricia’s voice reached him before he could take a step. “Come along, dear. Don’t disappear just yet.”
The afternoon settled into a quiet, painfully long visit. Soon, Aunt Patricia and his mother brought out a stack of old family albums from the lower shelf of the bookcase, and Edward sat demurely nearby while they turned the stiff black pages and murmured over photographs of weddings, summer holidays and little children from years past in carefully arranged clothes.
More than once Aunt Patricia paused over a faded photograph and tilted it toward Edward. “See how much trouble people once took to make children look proper?” she would say, as though the picture proved something. Edward nodded when he was expected to nod, keeping his hands folded and his knees together, while every beribboned child and lace-collared cousin in the album seemed to offer Aunt Patricia another quiet argument in favor of her ideas. With a feeling of resignation, Edward began to sense that his aunt was purposefully lingering to make sure he had no chance to get changed out of his pretty dress.
After they looked at the albums, Marian suggested that Edward might practice his piano for a little while. He seized on the suggestion at first, grateful for anything that gave him a clear task and spared him from sitting beneath Aunt Patricia’s inspection. But even the piano failed to feel ordinary. The hem of his yellow dress spread over the bench when he sat, and he had to arrange it before placing his feet near the pedals. Aunt Patricia took a chair nearby and listened with folded hands as Edward began to play a few scales. Then, he played a simple piece Marian liked, keeping his eyes on the keys.
After he was done at the piano, Edward remained downstairs in his yellow dress. He perched on the edge of a chair while the two sisters talked about the salon, the portrait and how nice the museum visit was.
Aunt Patricia alluded to his wardrobe again only once more in passing, as if discussing curtains. “We must think practically, of course,” she said, stirring her tea. “But if Edward is to do this properly, it may be wise to have a few more suitable things on hand.”
His mother made no promise, yet she did not dismiss the idea either.
When Aunt Patricia finally rose to go, the afternoon light had already begun to soften at the windows. Edward stood with his mother in the hall while Patricia kissed his mother’s cheek and then turned to him with one last approving look. “What a lovely day, my darling,” she said. “With more practice, you will be much more comfortable in your frocks and dresses.” Then, she rested her hand on his dainty shoulders to pull him closer, “Let Aunty give you a kiss, sweetie,” and then she pecked him on his cheek.
Edward stiffened. He could feel the faint, waxy print of her lipstick on his skin even before Marian’s eyes flicked toward it. Aunt Patricia gave a soft little tut, opened her handbag, and drew out a folded tissue with unhurried precision. “Oh, but look what I’ve done,” she murmured, as if the mark were a sweet little accident.
She touched the corner of the tissue lightly to her tongue, then held Edward still with the gentlest pressure beneath his chin and dabbed at his cheek. The gesture was delicate but smothering in its delicacy. Edward stood motionless while she wiped away the lipstick, feeling smaller with every soft pat of the damp tissue.
At long last, she left. Edward watched from the doorway until her car disappeared down the street. Only then did he climb the stairs, each step lifting the prissy yellow skirt against his knees. Relief should have come then, but it was uneasy. Even as he opened his bedroom door, he could still hear Aunt Patricia’s voice in his head.
Active Sissy Stories / Re: Baby Cindy III: Lovey Dovey Diaper Butt
« Last post by babyian on September 01, 2026, 12:29:03 PM »
Active Sissy Stories / Re: The Portrait of Edward Gray/ Suttle protest
« Last post by gunrunner on August 30, 2026, 02:53:45 PM »
But being an intellegent young man; he can surly create a suttle protest of sorts. sissyboy1212, you have mentioned several times that it is a task to always pose in the same postion, even with the support equipment. So, if they have to break the pose several times each session for a bathroom break, Edward would be protesting in a suttle way. Curtainly, the need to quinch a thirst woiuld be denied. When Edward would have privite time to potty and wash his hands, he could drink a little more. It may not seem like much, but it would give him some satifaction to know his "Auntie" would be frustrated.
Then heaven forbid, he should leak a little, and scare them that the old dress would be stained.
He is a young boy and he surely can come up with some form of protest. Maybe this would lead to not having to wear that horrid old dress for each session.
Thank you for your efforts, and my you continue to have the muse to write.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 30, 2026, 01:50:12 PM »
Edward was relieved when they finally got back home. Hopefully, his aunt would leave, he could change and then he’d be done with dresses and curls at least for a while. Aunt Patricia paused beside the car, however, wearing a thoughtful look that had followed them out of Belladonna. The morning had grown bright and warm.
“You know, Marian,” she said, looking Edward over with immense satisfaction, “it would be a shame to just stay home after all that effort this morning. He looks so nice and presentable, and it is such a lovely day.”
Edward’s heart sank a little, because he sensed at once where this was going. He would be thrilled to just stay at home right now. His mother glanced toward him, perhaps ready to say that they’d already had a busy morning, but Aunt Patricia continued before any objection could materialize. “Why don’t we go out for a light lunch?” she suggested brightly. Then, with a pleased little smile, she added, “I’m in the mood for a nice fresh salad or a small sandwich. Besides, the fresh air would do us all good.”
It seemed to be decided. They spent a few minutes at home first to freshen up. Aunt Patricia couldn’t resist making some small adjustments to Edward’s appearance. Apparently, he had managed to get his hair bow crooked between the salon and the house, so she set it right. She also insisted on smoothing his skirt where a slight wrinkle seemed to have appeared, as if he had put it in there on purpose. Edward stood before the hall mirror and endured these little attentions with a weary resignation.
Within the hour, Aunt Patricia drove them to a bistro-style café tucked along a pedestrian lane in the new shopping center of town. The place had a European air with colorful awnings and a pleasant terrace outside. Inside, the walls were hung with small framed prints of Paris streets and seaside villages, but Aunt Patricia wanted to sit on the terrace.
The hostess smiled and led them to a table next to a row of planters with boxwoods and flowering plants. From there, they overlooked the busy pedestrian area. It was a wide brick walkway where shoppers drifted past with paper bags and people were window shopping. From where they sat, pedestrians were only a few feet away on the other side of the planters.
Edward sat carefully, aware of the faint rustle of his skirt as he lowered onto the chair. Edward would have preferred to eat inside. Here, on the terrace, he felt as if he were on constant display to everyone walking by. The waitress brought glasses of water beaded with condensation, and Aunt Patricia took her time reading through the menu.
After a while, the waitress returned. Before taking their orders, he paused as she took in Edward’s attire and said, “My goodness… what an adorable outfit!”
Edward’s face went hot at once. He knew exactly what she was seeing. He drew his ankles together under the chair and pressed his hands together as if it would make his dress and tights less obvious.
Marian gave the waitress a careful smile, polite and grateful at the edges, but it did not quite reach her eyes.
Aunt Patricia, by contrast, looked pleased enough to glow. “Thank you,” she said pleasantly. “He is precious, isn’t he?” she continued, “My nephew Edward here is working on a special family project involving a portrait, and he has been such a doll today!”
The waitress blinked in surprise. “Edward… is it?” she asked, clearly off balance. Before Edward could answer, she recovered, “Well… Edward,” she said, making the correction with some awkwardness, “you do look very nicely put together today.”
Edward turned crimson. He managed a tiny, feminine nod. “Thank you, miss,” he whispered, though the words seemed to catch in his throat. Edward lowered his eyes to the white plate in front of him and wished the bushes next to the table were taller.
In contrast, Aunt Patricia looked serene and satisfied, as if the matter had been clarified for everyone in the bistro. Then, she ordered for the table. She got chicken salads on croissants for herself and her sister. For Edward, she ordered a Croque Madame. Edward had no idea what that was until he looked at the menu again. It appeared to be a fancified ham and cheese sandwich. She also ordered a delicate cuc-umber sandwich plate to be shared by the table.
“Nothing too heavy,” Aunt Patricia said approvingly, folding her napkin across her lap.
Soon the food arrived on fussy little plates. As they ate, people walked down the pedestrian lane in a steady stream. A few smiled at the three of them occasionally or even spoke. Edward felt that all the passersby must have looked at them and thought they were just two ladies enjoying lunch in the fresh air with their prissy daughter or niece. The thought made his cheeks warm.
Then, to Edward’s horror, two boys from Edward’s school, Tommy and Ben, wandered lazily into view along the sidewalk. They were laughing and looked completely at ease. Edward recognized them at once. They weren’t his friends, exactly, but he knew them.
“Please don’t look over here,” he thought, “Please keep walking!”
He drew his elbows close to his sides, as if making himself narrower might make him invisible. The pair of boys slowly passed the café, still grinning. Then, Tommy looked toward the table and his laughter quieted. Ben followed his gaze. For a moment they stared at Edward with uncertain recognition, their faces narrowing as if they had seen something familiar that they couldn’t quite place.
As Tommy and Ben stood there, just on the other side of the planters, it seemed their attention was caught but not settled. Edward went rigid in his chair. He lowered his chin by the smallest degree. Then, mercifully, something farther down the sidewalk caught Ben’s attention. Tommy seemed to follow his look. Tommy made the slightest shrug. After a brief pause, the boys exchanged a look Edward could not read and drifted on down the sidewalk. Their conversation seemed to resume, but Edward could not hear what was said. Perhaps, he hoped, it had nothing to do with him at all.
Edward scarcely breathed until their backs were several yards away. For one blessed second, he let himself believe he had escaped. But the certainty did not last. A small uneasiness remained. Tommy had stared a beat too long. Ben had looked twice. Perhaps they had only failed to place him in the moment. Perhaps the connection would come later. Edward tried to convince himself that if they had recognized him, they would have said something. Still, doubt stayed with him, quiet and persistent.
Aunt Patricia noticed the change in Edward’s demeanor at once. Her gaze moved from the boys walking away to Edward’s hunched shoulders, and one eyebrow lifted by the smallest degree. Instead, she asked in a voice that seemed meant for the table but carried farther than it needed to, “Edward, dear, did you know those boys?”
“Yes, Aunty… from school,” he murmured.
Aunt Patricia brightened at once. “Well, then, you should have said hello, dear,” she said cheerfully. “There is no reason to sit there looking as if you have been caught at something. It would be the simplest matter in the world to explain about your portrait.” She smiled as though the situation were perfectly ordinary, “They would probably have found it fascinating, really!”
Edward stared at her, flabbergasted. For a moment he couldn’t decide whether she truly failed to understand or whether she understood perfectly and was just choosing to pretend otherwise. Did she honestly imagine Tommy and Ben would nod thoughtfully at the story and immediately understand why he was dressed as a dainty little girl?
“Aunty… please,” he started helplessly, but the words would not come. He looked from her to his mother and back again, searching for some sign that the obvious had landed.
With a thin smile, his mother simply said, “Just eat your lunch sweetheart.”
Aunt Patricia gave a light little laugh, as if his distress were a charming misunderstanding. “Oh, Edward, you mustn’t be so dramatic,” she said cheerfully. “Truly, you look very distinguished, and one must expect a certain amount of attention when one is dressed properly. There is nothing wrong with being noticed for appearing neat, polished, and well presented.” She tilted her head, studying him with satisfied approval.
Edward stared at her, too stunned to interrupt.
Aunt Patricia seemed to enjoy the effect. As they continued eating, she gaily discussed the portrait, the salon, and the importance of presenting oneself properly in the same voice she might have used to comment on the weather. Then, she seemed to take more interest in Edward’s table manners. “Careful with your napkin, dear,” she said, smoothing the linen over her knees to demonstrate. “It saves one from all sorts of little disasters.”
Edward obediently smoothed his own napkin over his lap, very conscious of his skirt brushing against his tights.
“And take smaller bites,” she added lightly, “one should never treat a luncheon like a race.”
As she watched, Edward took a tiny nibble of his sandwich, moving more slowly. She admonished him to keep his hands in his lap when he was not eating, to keep his knees demurely together beneath the table and to use his napkin to dab at his mouth before drinking. Soon Edward was painfully conscious of his every motion as he picked at his lunch like a nervous bird.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 29, 2026, 03:09:42 PM »
Mrs. Bell pursed her lips for a moment as she appraised her work, and Edward felt the small pause lengthen. “Hold still for me, dear. Your hair is lovely, but it I think we need to add a finishing touch.” Edward blinked, unsure whether that was a criticism or not. Mrs. Bell reached onto the counter before he could ask. “Chin up,” she directed. Then she began dusting the lightest touch of powder across his face. After that, she brushed a faint bloom of blush onto his cheeks until they held a soft rosy tint. It was less makeup than she used in the portrait studio, but it felt significant because it was happening here in the public brightness of Belladonna. It seemed the portrait continued to follow him out of the studio. Finally, she touched his lips with the same pale pink shade she favored for the sittings, leaving only a delicate suggestion of color.
Edward sat very still, afraid that any objection would only draw more attention. Mrs. Bell stepped back, studied him once more, and smiled with satisfaction. “There,” she announced. “That looks perfect with a touch of color… It just didn’t look quite right before.”
Finally, Mrs. Bell was done. “There you are, sweetie,” she said with a bright smile, “all polished and pretty!”
“Thank you, Mrs. Bell,” Edward replied softly. As the teen rose from the chair, he felt a little lightheaded from the overwhelming feeling that he was being being transformed. He shyly followed his aunt and mother back into the lobby of Belladonna. Aunt Patricia settled the bill, and Mrs. Bell expressed her thanks at what must have been a generous tip. As they prepared to depart, Edward was acutely aware of the new bounce of his softly falling hair. The lavender scent of the shampoo and conditioner lingered, and he felt as if even a slight breeze would make it flutter in a newly girlish way. At that moment, the salon door chimed and more customers entered the salon. Edward turned just in time to see Lily arriving with her mother. Apparently, they were here for their own appointments!
Lily stopped short in shock, recognition brightening her face as her eyes went at once to Edward’s smooth, shining hair. “Oh Edward!” she said, sounding delighted, “What a surprise to see you here… and in your adorable dress again!” Then she giggled and said, “Wow, your hair looks really nice. I had no idea you were… going so all out for your new look!” She added, “that is a really cute hair bow!”
The mention of his hair bow made Edward’s ears burn even more for some reason. He had almost managed not to think about it, but now he could feel it there again, lacy and secure among the curls, a dainty little finish that made his whole hairstyle seem even more openly pretty. Edward felt Lily’s compliments land strangely as he was exposed as this way in front of his schoolmate. And now Lily’s mother was there too. Edward turned beet-red and became painfully aware of everything at once. He shifted his feet nervously in his glossy Mary Janes, overly conscious of his dress’s careful fit and the little shift of its skirt against his knees. His stomach tightened. A hot, prickling flush crept up his neck, and his hands gave a small, helpless twitch at his sides. He wanted to hide, but there was nowhere to go.
Lily inspected him with open curiosity, taking in the yellow dress with its charming bubble sleeves and little flowers near the hem, the hair bow, the curled and shining hair, and the careful little details that made the whole outfit seem complete. “Oh,” she said with a gentle tease, brightening again, “you have your nail polish on again too… I was a little disappointed you took it off for school!”
Edward’s fingers jerked almost before he could think. He curled them inward, tucking his polished nails against his palms, then shifted his hands behind the folds of his yellow skirt as if the fabric might somehow hide them. But the quick movement only made him feel more exposed. Lily smiled as if his bashfulness only made the look more charming. “It really does all go together,” she said sweetly. “The dress and tights, your hair, the hairbow, your nails, those darling shoes. Oh my gosh you're even wearing makeup! You look… very sweet, Edward.”
Edward’s cheeks warmed more, and he lowered his gaze toward his Mary Janes. “Thank you, Lily,” he managed softly. He felt keenly aware of the slick pink lipstick coating his lips.
“Mrs. Bell just finished up on him,” Aunt Patricia couldn’t help but add, “she did a wonderful job!”
Edward blushed more deeply, and Lily tugged lightly at her mother’s sleeve. With a quick little smile, she said, “Mom, this is the boy I told you about… the whole portrait thing?” Then with a grin, she added, “although he doesn’t look much like a boy today! That’s the same dress he was wearing in the ice cream shop!”
Lily’s mother looked from Edward’s flushed face to his neatly arranged curls and demure outfit, then smiled kindly although with some surprise she could not quite conceal. “Oh yes. Well,” she said pleasantly, “it’s very nice to meet you, Edward. Lily told me all about your interesting project, and I will say you look very carefully put together today. Your curls are lovely.”
Edward’s mother gave him a gentle verbal nudge. “Edward,” she said softly, smiling politely at Lily’s mother, “what do we say, honey?”
Edward swallowed, aware of Aunt Patricia standing just behind him. “Thank you, ma’am,” he replied in a small but careful voice.
Lily’s mother softened her smile, and she gave Edward an encouraging nod. “You’re very welcome,” she said. “I must say you seem very… dedicated to this unusual pursuit.”
Lily looked him over again, and her curiosity softened into a teasing smile. “So I have to ask… is this your only dress?” she asked. “Or do you have others too?”
Edward’s blush deepened, and he glanced down at the glossy toes of his Mary Janes before answering. “I… I have a pink one too,” he admitted reluctantly.
Lily’s eyes lit up instantly. “Oh? I bet it’s adorable too,” she said gently, “I’d love to see that one sometime!”
Edward’s stomach fluttered at that. Somehow Lily’s interest felt even more dangerous than her teasing. He felt a hot blush spread up from his collar. The thought made him lower his gaze again. He gave a small, nervous shrug as if that might make the whole subject go away.
Aunt Patricia, on the other hand, practically beamed, her face shining with satisfaction as she stood just behind Edward and looked him over with unmistakable pride. She seemed almost unable to keep quiet, her smile growing each time Lily or her mother noticed another detail. “I’m sure that could be arranged couldn’t it, Edward?”
There was an uncomfortable silence, and Edward realized that they were all waiting for him to speak. “Uh yes… Aunty… sometime, maybe,” he stammered weakly.
“His look is coming along beautifully” she said, lightly resting a fond hand on his shoulder. “For the portrait… of course,” she added as a hasty, amused afterthought.
Edward stood between Lily’s delighted smile and Aunt Patricia’s glowing pride feeling thoroughly flustered, as if both of them were seeing right through him. Every compliment tilted him further off-balance. He was embarrassed by his dress, his dainty curls and his shiny nail polish, but he could not quite deny the uncomfortable truth that all of it suited him more than he wished it did. He knew how pretty he looked. That was what made the moment so confusing.
In the moment, he cringed to think that despite everything that had happened so far, this felt like only the beginning. The thought struck him with a sinking weight that seemed to pull the air out of his chest. There were still many portrait sittings ahead of him. There were more careful afternoons where he would have to sit perfectly while Miss Vale smoothed his dress, adjusted his curls and positioned his hands. There would be more visits to Belladonna with more trimming, curling, brushing and styling.
He sighed softly.
A few minutes later, having said an awkward goodbye to Lily and her mother, they were walking back to Aunt Patricia’s car. “You know,” Aunt Patricia said with thoughtfully, “your little friend Lily made me think that it’s a pity you only have the two dresses to choose from.” She continued, “they need to be cleaned on a regular basis, and you should have more options. I think your wardrobe ought to rise to the occasion.”
Edward nearly froze as she spoke. “My wardrobe, Aunt… Aunty Patricia?” Over the last week, his aunt had begun encouraging him to use the more childish term “Aunty” as opposed to the slightly more grown up “Aunt” when he spoke to her. If he called her “Aunt Patricia,” there was always a flash of disappointment in her eyes. He kept trying not to rock the boat.
“Just a few items, sweetheart,” Aunt Patricia said brightly. “Another pretty dress or two, perhaps. An extra pair of shoes for variety. Some nice things suitable for your sitting days and the salon. Perhaps some different things for some more outings like the museum now that school is out. We could go shopping together.”
“Aunty Patricia,” Edward began, “I don’t think I really...”
She interrupted him again, “oh don’t be silly, darling,” she said brightly, “your Aunty will be more than happy to get you some more delightful things.”
Edward grimaced, and Mrs. Gray gave her sister a pleading look. By his mother’s standards, this was an almost shocking display of disagreement.
Aunt Patricia clearly noticed, but she only smiled as if this resistance were merely a charming preliminary stage. She replied with an amused grin to her sister, “you certainly can’t argue that he should have some extra changes of undergarments at the very least… for hygiene if nothing else!”
Edward’s mother was silent.
Aunt Patricia continued almost imperiously, “well, we shall see.”
Edward hoped very much that they would not. All the way home, and for hours afterward, the word “wardrobe” would come to trouble him more than he wanted.
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 29, 2026, 02:05:15 PM »
Saturday morning arrived in a flash. The first visit to Belladonna was more taxing, in some ways, than the first portrait sitting. On Saturday morning, Aunt Patricia had arrived earlier than expected to drive them to the salon. To his chagrin, Edward learned that his hair appointments would require the same preparation as the sittings themselves. He had been wearing a normal pair of shorts and a striped polo shirt when she made her entrance.
“Why Marian, why isn’t Edward dressed yet?” she asked with a trace of disappointment.
His mother’s face tightened a bit, but she only said, “We didn’t expect you so early Patricia.” It came out rather feebly.
For a moment, Edward was confused. He was dressed. “What do you mean… Aunty?” he began to ask. But even as the words left his lips, he instinctively knew the answer. He realized that it had been useless to pretend otherwise.
“You can't wear that, sweetheart," she said with a dismissive wave of her hand. "Of course, we'll get you into one of your pretty dresses for your hair appointments, darling,” Aunt Patricia almost giggled as she removed any doubt. Then her expression changed to amusement if he had said something humorous. “The salon is part of the process now, dear. We can’t separate the maintenance from the portrait.” With a more insistent tone she added, “it would be silly to show up for a girl’s hair appointment dressed as a boy, now wouldn’t it dear?”
Edward gulped. Then he caved almost immediately with a monotone voice, “of course Aunty… that would be… silly.”
“Never fear, Aunty is here!” she said cheerily. “I think that your adorable yellow frock would be perfect today. Let’s pair it with those precious tights again!” She added, “That outfit looked so charming in the ice cream shop the other day with your little friends!”
Once Edward was dressed, they were off in Aunt Patricia’s fancy car. Belladonna was an elegant salon with gilt mirrors, glass shelves and soft salon chairs that turned gently beneath bright lights. At least in Miss Vale’s studio, everyone knew the purpose of his curls. At Belladonna, he was an object of new curiosity. Soon, Mrs. Bell led him to the back. He was sat down meekly in a salon chair amongst all the ladies getting their hair done in his frilly yellow dress, pristine white tights and shiny Mary Janes.
Once he was perched on the chair, Mrs. Bell lifted Edward’s hair between two fingers and let it fall against his cheek. Propped on the counter, Edward saw the photograph of his great-great grandmother was displayed for reference.
“We just need to ensure your ringlets will continue to match the photograph,” Mrs. Bell observed, “and young hair grows fast.” She added, “Miss Vale depends on consistency.” She went on, “We are just going to refine and shape the ends and maintain the overall length.” Edward stared at his reflection in the mirror, where his hair fell around his face in soft, betraying waves.
Mrs. Bell began with a towel tucked carefully around his collar to protect his dress. A bright pink salon cape was snapped around his neck so that only his white tights and Mary Janes were visible beneath it. Then Mrs. Bell leaned the chair back and began washing his hair with lavender shampoo, working the suds through the longer strands near his temples with small circular motions. Next, she rinsed it until it fell smooth and heavy into the sink. Then she patiently worked in conditioner and rinsed again. She blotted his hair gently with a towel rather than rubbing. Finally, she sat him back up to face the mirror. She trimmed away the tiniest uneven tips and sectioned his still damp hair into neat rows with the point of a comb. She then wound it in soft rollers before drying it all gently with slightly warm air. She set several “practice” ringlets just to make sure they would behave correctly for the sittings.
As his hair was lovingly washed, conditioned and then carefully trimmed, Edward felt completely self-conscious and also a bit suffocated. The salon was unmistakably feminine in a way the studio was not. Belladonna was softer, brighter, and much more public. All around him, women discussed shades of nail polish, elegant hairstyles and fancy hair products. The sweet chemical smell of setting lotion and other scents filled the air. Sitting there in his yellow party dress under the pink cape made Edward feel as if he had crossed into a new reality. He wondered enviously how the other boys in his class were spending the first Saturday of their summer vacation. He was sure none of them were doing anything like this!
And of course, many of the ladies made admiring comments about the precious little girl getting her hair done. They doted over his dress, and they were charmed when he blushed sweetly at the attention.
Aunt Patricia and his mother watched it all from a comfortable sofa on the opposite wall. Embarrassingly, Aunt Patricia seemed to have no qualms in occasionally referring to him as “Edward” or “my nephew” a bit too loudly. More than one lady was surprised to find they were complimenting a sweetly attired boy! Of course, this only led to looks of bemusement and more conversation which just made Edward want to crawl into a hole.
As Mrs. Bell finished up with him, Edward noticed a difference in his hair. It seemed to lay smoother and shine more brightly with a polished hint of curl at the ends. She unsnapped and removed his salon cape, and he watched glumly in the large mirror as she took pains to delicately arrange his pretty yellow hairbow in his freshly styled hair.
Still watching himself in the mirror, Edward lifted one tentative hand to tentatively brush his curls with his fingers. They caught the salon light in glossy little curves, softer and brighter than he remembered his hair ever looking. “It looks so much softer,” he murmured before he could stop himself, his cheeks warming at the admission. After another uneasy glance at his image, he added in a smaller voice, “And… shinier too.” The words seemed to embarrass him as soon as they left his mouth.
Aunt Patricia, meanwhile, practically cooed over his shiny locks. “Oh, Edward, look at you!” she exclaimed. “How darling, sweetheart. See how your curls catch the light now? It is so much more refined and polished.” She gushed, “it brings out the sweet delicacy in your features.” With a smile, she added, “This can only help in making your portrait come alive.”
Edward had never given a lot of thought to his hair, but now it looked deliberately pretty and unmistakably girlish. It was glossy, curled, and fussed over in a way that seemed to invite attention. Embarrassment prickled at him as he realized just how much like a sweet little girl he now looked. He felt a pulse under his pretty dress as a small, traitorous flicker of admiration ran through his thoughts. His curls were indeed pretty. He was… pretty. He hated to admit it even to himself. If his hair could be trained so easily with a little shampoo, conditioner, trimming and curling to look this different and girlish, what else about him would be trained and shaped in this process?
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