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Active Sissy Stories / Re: The Portrait of Edward Gray/ Suttle protest
« Last post by gunrunner on Today at 02:53:45 PM »
Edward is in a sticky situation. He does not want to offend his "Auntie" and posibly effect the money she provides his mother.
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.
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.
2
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on Today at 01:50:12 PM »
Lunch with Aunt Patricia
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.
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.
3
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on Yesterday at 03:09:42 PM »
Another Surprise Encounter
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.
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.
4
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on Yesterday at 02:05:15 PM »
A Delightful Trip to Belladonna
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?
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?
5
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 28, 2026, 08:57:06 PM »
Edward's Last Day of School
For most of Edward’s classmates, the last bell of the school year rang with a jubilant finality. Almost at once the hallways became a river of students and voices chattering excitedly over one another. Lockers slammed open and shut. One of Edward’s classmates bragged that his family was leaving for the lake first thing in the morning. Another boy looked forward to his baseball camp. Even the teachers seemed a little lighter as they stood by their doors saying cheerful goodbyes while the students spilled past them into the warm afternoon.
Each happy exchange among his classmates seemed to strike him in a different place. Summer, to everyone else, sounded wide open and carefree. To Edward it almost felt like a door closing. The rest of his afternoon would be subject to Aunt Patricia’s schedule and the demands of the portrait. Very soon, he would be prettily dressed in one of his dresses and on the way to Miss Vale’s studio for another sitting. Another long afternoon of ringlets, velvet, and stillness was in front of him. Even more days being dressed, curled, powdered and posed awaited him after that. He sighed in resignation. Weeks of his summer had been stolen in advance.
And of course, there was also the matter that the girlish way he was spending his free time was no longer a close secret. That thought kept returning. Lily knew, Hannah knew, Sophie knew, Rachel knew, and those were only the names he knew for sure. There seemed to be another cluster of girls at neighboring lockers, friends at lunch tables and older students who knew what a sissy he was becoming. Edward could not stop imagining Hannah sharing the pictures of him in his darling yellow dress at the ice cream shop. Who else would find out? Who had already found out?
Edward moved through the crowd quietly, trying not to listen.
As soon as he was home, he found himself back in his darling pink Sunday school dress. Then, in what seemed like the blink of an eye, he was back in Miss Vale’s studio. This time, the swiftness of the transition unsettled him more than anything. Less than two hours earlier, the last bell of the school year had released everyone else into summer. He could still hear it in his mind. Edward had been carried in the opposite direction.
He was again dressed with careful efficiency in his corset, tights, silk chemise and fluffy petticoats. He quietly endured the skilled pull of Mrs. Bell’s comb through his hair and the return of his adorably glossy ringlets. The vaguely familiar layer of powder and lipstick made his face soft and demure once more as he was again meticulously fastened into the old lilac gown.
Miss Vale then guided him back onto the chair and made sure his layers of skirts and petticoats were arranged just so. She placed his hands and feet with that same gentle precision. Edward sat very still as the pose closed around him again. All Miss Vale’s little supports, stays and ties were put in place to ensure he held the most delicately girlish pose for his portrait. He knew now what each touch and adjustment meant, and he felt a fresh embarrassment in how quickly his body obeyed the routine. Jarringly, the happy sounds from the playground cascaded through the window as Edward was again enveloped in his elaborate Victorian finery.
The seconds stretched into small eternities as he sat demurely, encased in his intricately feminine wardrobe.
Aunt Patricia leaned toward his mother with a glowing smile. “He really is so lovely like this,” she murmured admiringly, “look how much more natural he looks today!”
Edward silently cringed as his Aunt Patricia practically fawned over his girlish appearance. He was unsettled to feel another disturbing warmth and excitement in his frilly panties!
Almost as if she sensed his reaction, his aunt’s smile widened with unmistakable satisfaction. “His hands rest so daintily, and it’s so sweet how those darling ringlets frame his face.” Aunt Patricia gave a pleased little sigh. “Practice has done wonders for our little darling. It is almost as if the gown remembers him. He looks as though he were born for this!”
His mother nodded softly but did not speak. Miss Vale continued to paint with gentle but confident strokes of her brush.
Later, with his fourth sitting mercifully behind him. Edward again sat with his mother and aunt in the little ice cream shop. Aunt Patricia had decided it would be nice to continue these “outings” after his sittings as a reward. All things considered, Edward would much rather have gone straight home than spend more time dressed like this with all the eyes on him. He had been reticent to say anything, however, and his mother had of course gone along. So here he sat again back in his pink Sunday dress. He worried that Lily or Hannah or one of the other classmates who seemed to know about him would walk in any moment.
It was while they ate that Aunt Patricia spoke again. “Edward, dear, now that school is out for the summer, we can make some more plans.” She continued, “Miss Vale told me that she thinks she will actually need about fifteen more sittings to get your portrait exactly right.”
Edward started involuntarily. “Fifteen more… Aunty?” he managed to spit out.
“Well yes, now that she’s had time to assess the work, I’ve asked her to make sure she captures all the rich details of your hard work, sweetie!”
Edward had been counting the days until summer looking forward to a reprieve. He had desperately wanted to reclaim at least a little free time away from dresses for himself. The last few days had been nerve-wracking. Now the number of sittings he would have to endure seemed to multiply of their own accord.
“Since it appears we have all this extra time,” Aunt Patricia announced happily, “I spoke to Mrs. Bell today and she agrees we should arrange some maintenance appointments for your hair while you are doing your sittings.” She continued, “consistency is everything!” She explained, “Miss Vale cannot be expected to paint the same ringlets if they change from one session to the next.”
With a sinking feeling, Edward sat silently as Aunt Patricia informed him and his mother that she had already set up a series of “maintenance” appointments at Mrs. Bell’s salon, “Belladonna,” on Saturday mornings until the portrait was done. “Your first one is this Saturday,” she announced.
Edward looked powerlessly at his mother, helplessly hoping she might object. Mrs. Gray only nodded uncertainly. “If Miss Vale thinks it will help the sittings, perhaps it is sensible.” Edward understood then that this portrait project had grown even more tentacles outside the studio.
“And since we have such an open schedule before your sittings now, Mrs. Bell offered as well that we could bring you to Belladonna for a brief appointment before each sitting to put your ringlets in.” Aunt Patricia smiled, “It’s right down the street, and she just thinks it will be faster and easier to do it in her salon instead of the studio. Of course, I agreed at once!”
“Patricia, won’t that be expensive?” Edward’s mother asked hesitantly.
“Don’t give it a second thought, Marian,” Aunt Patricia replied nonchalantly, “It was my idea, so of course I will see to it.”
Edward’s spirits plummeted. Now his Saturday mornings would be stolen too, and the added prospect of a hair salon visit before every sitting promised to draw things out even more. Adding this new regimen of hair care did not feel like dressing up for a single afternoon. A dress could be taken off. A little makeup could be washed away. But his hair was his hair, growing every day. Aunt Patricia now spoke of it as something to be preserved, trained and closely managed. The continuity of it all began to weigh on him, the idea that he was always being kept ready for this portrait’s increasing demands.
For most of Edward’s classmates, the last bell of the school year rang with a jubilant finality. Almost at once the hallways became a river of students and voices chattering excitedly over one another. Lockers slammed open and shut. One of Edward’s classmates bragged that his family was leaving for the lake first thing in the morning. Another boy looked forward to his baseball camp. Even the teachers seemed a little lighter as they stood by their doors saying cheerful goodbyes while the students spilled past them into the warm afternoon.
Each happy exchange among his classmates seemed to strike him in a different place. Summer, to everyone else, sounded wide open and carefree. To Edward it almost felt like a door closing. The rest of his afternoon would be subject to Aunt Patricia’s schedule and the demands of the portrait. Very soon, he would be prettily dressed in one of his dresses and on the way to Miss Vale’s studio for another sitting. Another long afternoon of ringlets, velvet, and stillness was in front of him. Even more days being dressed, curled, powdered and posed awaited him after that. He sighed in resignation. Weeks of his summer had been stolen in advance.
And of course, there was also the matter that the girlish way he was spending his free time was no longer a close secret. That thought kept returning. Lily knew, Hannah knew, Sophie knew, Rachel knew, and those were only the names he knew for sure. There seemed to be another cluster of girls at neighboring lockers, friends at lunch tables and older students who knew what a sissy he was becoming. Edward could not stop imagining Hannah sharing the pictures of him in his darling yellow dress at the ice cream shop. Who else would find out? Who had already found out?
Edward moved through the crowd quietly, trying not to listen.
As soon as he was home, he found himself back in his darling pink Sunday school dress. Then, in what seemed like the blink of an eye, he was back in Miss Vale’s studio. This time, the swiftness of the transition unsettled him more than anything. Less than two hours earlier, the last bell of the school year had released everyone else into summer. He could still hear it in his mind. Edward had been carried in the opposite direction.
He was again dressed with careful efficiency in his corset, tights, silk chemise and fluffy petticoats. He quietly endured the skilled pull of Mrs. Bell’s comb through his hair and the return of his adorably glossy ringlets. The vaguely familiar layer of powder and lipstick made his face soft and demure once more as he was again meticulously fastened into the old lilac gown.
Miss Vale then guided him back onto the chair and made sure his layers of skirts and petticoats were arranged just so. She placed his hands and feet with that same gentle precision. Edward sat very still as the pose closed around him again. All Miss Vale’s little supports, stays and ties were put in place to ensure he held the most delicately girlish pose for his portrait. He knew now what each touch and adjustment meant, and he felt a fresh embarrassment in how quickly his body obeyed the routine. Jarringly, the happy sounds from the playground cascaded through the window as Edward was again enveloped in his elaborate Victorian finery.
The seconds stretched into small eternities as he sat demurely, encased in his intricately feminine wardrobe.
Aunt Patricia leaned toward his mother with a glowing smile. “He really is so lovely like this,” she murmured admiringly, “look how much more natural he looks today!”
Edward silently cringed as his Aunt Patricia practically fawned over his girlish appearance. He was unsettled to feel another disturbing warmth and excitement in his frilly panties!
Almost as if she sensed his reaction, his aunt’s smile widened with unmistakable satisfaction. “His hands rest so daintily, and it’s so sweet how those darling ringlets frame his face.” Aunt Patricia gave a pleased little sigh. “Practice has done wonders for our little darling. It is almost as if the gown remembers him. He looks as though he were born for this!”
His mother nodded softly but did not speak. Miss Vale continued to paint with gentle but confident strokes of her brush.
Later, with his fourth sitting mercifully behind him. Edward again sat with his mother and aunt in the little ice cream shop. Aunt Patricia had decided it would be nice to continue these “outings” after his sittings as a reward. All things considered, Edward would much rather have gone straight home than spend more time dressed like this with all the eyes on him. He had been reticent to say anything, however, and his mother had of course gone along. So here he sat again back in his pink Sunday dress. He worried that Lily or Hannah or one of the other classmates who seemed to know about him would walk in any moment.
It was while they ate that Aunt Patricia spoke again. “Edward, dear, now that school is out for the summer, we can make some more plans.” She continued, “Miss Vale told me that she thinks she will actually need about fifteen more sittings to get your portrait exactly right.”
Edward started involuntarily. “Fifteen more… Aunty?” he managed to spit out.
“Well yes, now that she’s had time to assess the work, I’ve asked her to make sure she captures all the rich details of your hard work, sweetie!”
Edward had been counting the days until summer looking forward to a reprieve. He had desperately wanted to reclaim at least a little free time away from dresses for himself. The last few days had been nerve-wracking. Now the number of sittings he would have to endure seemed to multiply of their own accord.
“Since it appears we have all this extra time,” Aunt Patricia announced happily, “I spoke to Mrs. Bell today and she agrees we should arrange some maintenance appointments for your hair while you are doing your sittings.” She continued, “consistency is everything!” She explained, “Miss Vale cannot be expected to paint the same ringlets if they change from one session to the next.”
With a sinking feeling, Edward sat silently as Aunt Patricia informed him and his mother that she had already set up a series of “maintenance” appointments at Mrs. Bell’s salon, “Belladonna,” on Saturday mornings until the portrait was done. “Your first one is this Saturday,” she announced.
Edward looked powerlessly at his mother, helplessly hoping she might object. Mrs. Gray only nodded uncertainly. “If Miss Vale thinks it will help the sittings, perhaps it is sensible.” Edward understood then that this portrait project had grown even more tentacles outside the studio.
“And since we have such an open schedule before your sittings now, Mrs. Bell offered as well that we could bring you to Belladonna for a brief appointment before each sitting to put your ringlets in.” Aunt Patricia smiled, “It’s right down the street, and she just thinks it will be faster and easier to do it in her salon instead of the studio. Of course, I agreed at once!”
“Patricia, won’t that be expensive?” Edward’s mother asked hesitantly.
“Don’t give it a second thought, Marian,” Aunt Patricia replied nonchalantly, “It was my idea, so of course I will see to it.”
Edward’s spirits plummeted. Now his Saturday mornings would be stolen too, and the added prospect of a hair salon visit before every sitting promised to draw things out even more. Adding this new regimen of hair care did not feel like dressing up for a single afternoon. A dress could be taken off. A little makeup could be washed away. But his hair was his hair, growing every day. Aunt Patricia now spoke of it as something to be preserved, trained and closely managed. The continuity of it all began to weigh on him, the idea that he was always being kept ready for this portrait’s increasing demands.
6
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by Dancer4Fun on August 23, 2026, 08:27:10 PM »
I would have thought that Aunty Patricia would have included a pretty lemon coloured slightly padded training bra with his new dress.
If her goal is to eventually have him dressing fulltime a training bra would be the one thing that would be the most feminizing addition to his wardrobe.
Nearly all girls by the age of thirteen are wearing training bras weather they need them or not.
The first time he put on his training bra is when he would realise this is no short-term thing.
"But Aunty I don't need a bra."
"You silly boy, a training bra will help you feel more feminine and help you find your feminine stillness."
If her goal is to eventually have him dressing fulltime a training bra would be the one thing that would be the most feminizing addition to his wardrobe.
Nearly all girls by the age of thirteen are wearing training bras weather they need them or not.
The first time he put on his training bra is when he would realise this is no short-term thing.
"But Aunty I don't need a bra."
"You silly boy, a training bra will help you feel more feminine and help you find your feminine stillness."
7
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 23, 2026, 06:01:35 PM »
The Ice Cream Shop
After the third sitting, Aunt Patricia took it upon herself to take them all out to an ice cream shop afterward as a reward for getting through what had seemed a difficult day. She wanted to end things on a more positive note. Aunt Patricia called it “restoration after artistic exertion,” which made Edward roll his eyes, though subtly, because he was again reluctant to object properly.
He bashfully followed his aunt into the little shop in his yellow party dress, tights and patent Mary Janes. The smell of vanilla and sugar cones floated in the air. He was acutely aware, however, of the stares of the customers as they wondered why a little girl was so fancily dressed on a Tuesday afternoon. His cheeks, still rosy from the studio makeup, turned a deeper shade of red. The ice cream shop made him self-conscious in a different way from the studio. In Miss Vale’s studio, everyone knew the reason for the dress, the ribbons, and the careful posture. In the shop, strangers saw only what was in front of them. Edward wondered whether the woman behind the counter knew he was a boy and whether the two children at the next table were whispering about him. If anyone looked twice, his face grew warm.
Aunt Patricia, noticing nothing or pretending not to, beamed, “Doesn’t he look darling after all that hard work? So neat and dainty, and still with those precious little curls dangling just so.”
Edward’s shoulders tightened. “Aunty,” he muttered, “please…”
“But you look so natural like this,” she replied cutting him off mid-sentence. She lowered her voice only slightly. “Anyone would think you had been dressing this way all your life.”
They got their ice cream and moved to a little table where Edward tried to disappear into the wallpaper. He sat carefully, keeping his knees together and holding the cone daintily away from his dress lest he drip on himself. His ever-present corset kept him in a demure and upright posture. He was very aware that he was the picture of effeminate sugar and spice.
He had just managed another careful lick of his vanilla when the bell over the shop door jingled again, and two teenage girls stepped inside laughing together. Edward recognized them at once from school, which made his stomach drop straight into his shiny Mary Janes. They were not in his grade but one year ahead. Lily and Hannah were popular eighth graders who already seemed older and more certain of themselves than anyone in his own class. His instinct was immediate and desperate. He lowered his head quickly and tried to turn his face toward the window, hoping against hope that they would not look at him too closely. He felt a sudden, unwelcome stirring in his panties.
Unfortunately, Aunt Patricia noticed him ducking and misunderstood the movement entirely. “Edward, darling,” she said in her clear, carrying voice, “sit up properly. You will drip ice cream on your pretty dress if you crouch like that.”
Both girls turned immediately. Lily’s eyes widened first, moving from the pink gloss still faintly bright on Edward’s mouth to the puffed sleeves of his yellow dress and down to the patent shoes visible beneath the table. Hannah stared for half a second longer, then clasped a hand over her mouth. “Wait a second… I know you! You’re Edward right?” she said, barely keeping her voice from squeaking, “you go to our school!”
The fact that they were a grade ahead only made it worse. Older girls had a way of knowing everyone’s business before anyone else did, and their opinions seemed to float through school faster than ordinary gossip. Edward had seen Lily and Hannah standing by the lockers with their friends, laughing in little clusters that made younger students give them room. Now those same girls were looking at him as if he had just become the most astonishing thing in the shop.
Edward turned scarlet “Uh… yeah,” he squeaked. Then, he murmured, “Hi,” so quietly it was almost not a word at all. He wished he could slide beneath the little marble table and vanish among the chair legs.
Aunt Patricia, however, brightened like a lamp being turned up. “Oh, do you girls know our Edward?” she asked with delighted interest. “How lovely! He is in the middle of a very important family portrait project. He resembles his great-great grandmother so closely that we are having him painted in her Victorian gown.”
Lily and Hannah looked at each other in bewilderment. Then, they began to giggle in the breathless, helpless way girls did when they were trying not to be rude and failing. “Oh... my... gosh,” Lily said, drawing out every word. “Edward, you look so cuuute!”
Hannah nodded vigorously, pitching her voice into a high, sugary trill. “Too adorable! Look at your little pretty little dress!” She pressed both hands to her cheeks as if overcome, “I can’t even handle it.” Hannah leaned closer admiring the details of his dress and hair. “Oh my gosh Lily his curls are perfect.” She widened her eyes theatrically and clasped her hands under her chin. “Edward, you are giving serious Victorian doll energy.”
Edward could not tell whether they meant to be cruel. Their voices were bright and teasing, but their giggles were not mean enough for him to protest. Every word made him feel more helpless. Eight graders loved to gossip. If they thought he looked adorable, then soon other people would know they thought so.
“Please,” he said in a low voice, cheeks bright red, “can you… not tell everyone at school about… all this?” The last two words came out very quietly.
Lily glanced at Hannah, and Hannah pressed her lips together as if trying not to smile. “But you look so pretty, Edward,” Lily said. Still, she seemed to take sympathy on him, “I suppose… we can keep it between us ‘girls’ if you want!” Her voice had that older-girl brightness that made the reassurance less reassuring.
Hannah gave a tiny giggle, “it’s not every day that a boy from school turns up looking like a Victorian cupcake.” Lily gave her a look, and Hannah added, “OK we won’t tell… everyone.” Something about the way she said “everyone” made Edward cringe.
Lily chimed in. “Okay? But you have to stand up and show us your outfit.” Lily said, still half laughing, as if Edward were something on display in a shop window. “I want to see the whole look.”
Edward stiffened so hard that his corset seemed to tighten around him, but he reluctantly stood up. “Thank you,” he said softly. He was beside himself. Every giggle seemed to flutter straight under his skin, and every exaggerated compliment made his yellow dress feel brighter, puffier, and more impossible to ignore. Still, he did as they asked and slowly turned around for them. He started growing a little lightheaded. The embarrassment of the moment was causing an excited heat under his tights and panties. He tried to take shallow breaths.
“Oh look, Lily, he’s even wearing nail polish!” Hannah exclaimed.
Then, before he could protest, Hannah had whipped out her phone and taken some pictures of him! The pressure in his panties only increased.
“Edward, you are just the cutest thing in your darling little tights and Mary Janes! I love it!” Lily agreed.
“What do we say, dear?” his aunt prodded sweetly.
Blushing even more, Edward stammered softly in an uneven voice, “Thank you.”
Aunt Patricia only smiled proudly, as if Lily and Hannah’s reaction were exactly the sort of public admiration she intended. “Thank you, girls,” she said. “He is precious, isn’t he?”
Edward stared down at his melting ice cream, cheeks blazing, while his classmates giggled again. Finally, they let him sit back down and moved to the counter to place their orders.
“See you at school!” Hannah said cheerily as they walked away.
This was his last week of school before the summer break, but there were still two days left. Mercifully, Thursday was the last day, but there was no way this would be forgotten. With a sinking feeling, Edward watched Lily and Hannah whispering together at the counter, with sudden little bursts of laughter that made him flinch. His cheeks heated again, and his stomach turned cold as he realized the portrait was no longer something hidden away in the studio. Now it had escaped into the world where his classmates lived, and he could not call it back.
The next morning, Edward was on pins and needles as he walked into school. He saw Lily and Hannah in the hallway right away, as if they had been waiting for him. Edward was thankfully in ordinary clothes now, with no dress, no hairbow, and no nail polish. Still, he blushed as soon as he saw them. They came right over to him.
“Aww you look so plain and ordinary today, sweetie,” Hannah teased quietly, “But don’t worry, we’re not going to tell… everybody.”
Lily said somewhat guiltily, “I thought you should know, however, that I did let it slip to Sophie. I didn’t mean to but she saw me looking at the picture on my phone. I made her promise not to tell anyone else.”
This latest revelation lodged in Edward’s stomach like a stone. He stood awkwardly in front of the girls with his hands nervously half tucked into his pockets. Sophie was in his own grade and usually sat three tables away from him at lunch. He stifled a groan.
Over the next two days, Edward tried to tell himself that nothing had changed. School was nearly over, and everyone was distracted by yearbooks, summer plans and their final restless classes. But once he was watching for it, he could not stop noticing the signs.
Later in the afternoon, Sophie caught him by his locker with a knowing smile. Sophie stepped just close enough that he could hear her without anyone else catching every word. “Lily showed me your pictures,” she said with a smile, and Edward’s face went hot at once.
Before he could retreat into embarrassment, Sophie lifted one hand in a small, calming gesture. “I’m not going to make fun of you, Edward.” Her voice was soft and interested, “I only told Rachel, because she saw me react and asked what was going on, but I made her promise not to say anything either.”
Edward stared at the locker vent, too flustered to answer.
Sophie gave him a small, encouraging smile. “For what it’s worth, you looked darling,” she added, then seemed to realize how easily that might sound like teasing. “This whole thing must feel strange.” She glanced down the hallway to be sure no one was listening too closely.
“Please don’t tell anyone else,” he pleaded. Sophie nodded, “I won’t,” she said. “Rachel won’t either. Your secret is safe with us.” Then, with a gentle grin, “But I’d love to see you dressed up in person sometime.”
Despite all the assurances, on Thursday morning two other eight grade girls suddenly went quiet when he walked near them. They dissolved into giggles as soon as he passed. He realized that Hannah’s promise not to tell “everyone” was obviously not the same as telling “no one.”
No one other than Sophie said anything to him directly, however. That was almost worse. If someone had teased him plainly, perhaps he could have denied it or pretended not to care. Edward wished desperately that Lily and Hannah had never walked into that ice cream shop.
After the third sitting, Aunt Patricia took it upon herself to take them all out to an ice cream shop afterward as a reward for getting through what had seemed a difficult day. She wanted to end things on a more positive note. Aunt Patricia called it “restoration after artistic exertion,” which made Edward roll his eyes, though subtly, because he was again reluctant to object properly.
He bashfully followed his aunt into the little shop in his yellow party dress, tights and patent Mary Janes. The smell of vanilla and sugar cones floated in the air. He was acutely aware, however, of the stares of the customers as they wondered why a little girl was so fancily dressed on a Tuesday afternoon. His cheeks, still rosy from the studio makeup, turned a deeper shade of red. The ice cream shop made him self-conscious in a different way from the studio. In Miss Vale’s studio, everyone knew the reason for the dress, the ribbons, and the careful posture. In the shop, strangers saw only what was in front of them. Edward wondered whether the woman behind the counter knew he was a boy and whether the two children at the next table were whispering about him. If anyone looked twice, his face grew warm.
Aunt Patricia, noticing nothing or pretending not to, beamed, “Doesn’t he look darling after all that hard work? So neat and dainty, and still with those precious little curls dangling just so.”
Edward’s shoulders tightened. “Aunty,” he muttered, “please…”
“But you look so natural like this,” she replied cutting him off mid-sentence. She lowered her voice only slightly. “Anyone would think you had been dressing this way all your life.”
They got their ice cream and moved to a little table where Edward tried to disappear into the wallpaper. He sat carefully, keeping his knees together and holding the cone daintily away from his dress lest he drip on himself. His ever-present corset kept him in a demure and upright posture. He was very aware that he was the picture of effeminate sugar and spice.
He had just managed another careful lick of his vanilla when the bell over the shop door jingled again, and two teenage girls stepped inside laughing together. Edward recognized them at once from school, which made his stomach drop straight into his shiny Mary Janes. They were not in his grade but one year ahead. Lily and Hannah were popular eighth graders who already seemed older and more certain of themselves than anyone in his own class. His instinct was immediate and desperate. He lowered his head quickly and tried to turn his face toward the window, hoping against hope that they would not look at him too closely. He felt a sudden, unwelcome stirring in his panties.
Unfortunately, Aunt Patricia noticed him ducking and misunderstood the movement entirely. “Edward, darling,” she said in her clear, carrying voice, “sit up properly. You will drip ice cream on your pretty dress if you crouch like that.”
Both girls turned immediately. Lily’s eyes widened first, moving from the pink gloss still faintly bright on Edward’s mouth to the puffed sleeves of his yellow dress and down to the patent shoes visible beneath the table. Hannah stared for half a second longer, then clasped a hand over her mouth. “Wait a second… I know you! You’re Edward right?” she said, barely keeping her voice from squeaking, “you go to our school!”
The fact that they were a grade ahead only made it worse. Older girls had a way of knowing everyone’s business before anyone else did, and their opinions seemed to float through school faster than ordinary gossip. Edward had seen Lily and Hannah standing by the lockers with their friends, laughing in little clusters that made younger students give them room. Now those same girls were looking at him as if he had just become the most astonishing thing in the shop.
Edward turned scarlet “Uh… yeah,” he squeaked. Then, he murmured, “Hi,” so quietly it was almost not a word at all. He wished he could slide beneath the little marble table and vanish among the chair legs.
Aunt Patricia, however, brightened like a lamp being turned up. “Oh, do you girls know our Edward?” she asked with delighted interest. “How lovely! He is in the middle of a very important family portrait project. He resembles his great-great grandmother so closely that we are having him painted in her Victorian gown.”
Lily and Hannah looked at each other in bewilderment. Then, they began to giggle in the breathless, helpless way girls did when they were trying not to be rude and failing. “Oh... my... gosh,” Lily said, drawing out every word. “Edward, you look so cuuute!”
Hannah nodded vigorously, pitching her voice into a high, sugary trill. “Too adorable! Look at your little pretty little dress!” She pressed both hands to her cheeks as if overcome, “I can’t even handle it.” Hannah leaned closer admiring the details of his dress and hair. “Oh my gosh Lily his curls are perfect.” She widened her eyes theatrically and clasped her hands under her chin. “Edward, you are giving serious Victorian doll energy.”
Edward could not tell whether they meant to be cruel. Their voices were bright and teasing, but their giggles were not mean enough for him to protest. Every word made him feel more helpless. Eight graders loved to gossip. If they thought he looked adorable, then soon other people would know they thought so.
“Please,” he said in a low voice, cheeks bright red, “can you… not tell everyone at school about… all this?” The last two words came out very quietly.
Lily glanced at Hannah, and Hannah pressed her lips together as if trying not to smile. “But you look so pretty, Edward,” Lily said. Still, she seemed to take sympathy on him, “I suppose… we can keep it between us ‘girls’ if you want!” Her voice had that older-girl brightness that made the reassurance less reassuring.
Hannah gave a tiny giggle, “it’s not every day that a boy from school turns up looking like a Victorian cupcake.” Lily gave her a look, and Hannah added, “OK we won’t tell… everyone.” Something about the way she said “everyone” made Edward cringe.
Lily chimed in. “Okay? But you have to stand up and show us your outfit.” Lily said, still half laughing, as if Edward were something on display in a shop window. “I want to see the whole look.”
Edward stiffened so hard that his corset seemed to tighten around him, but he reluctantly stood up. “Thank you,” he said softly. He was beside himself. Every giggle seemed to flutter straight under his skin, and every exaggerated compliment made his yellow dress feel brighter, puffier, and more impossible to ignore. Still, he did as they asked and slowly turned around for them. He started growing a little lightheaded. The embarrassment of the moment was causing an excited heat under his tights and panties. He tried to take shallow breaths.
“Oh look, Lily, he’s even wearing nail polish!” Hannah exclaimed.
Then, before he could protest, Hannah had whipped out her phone and taken some pictures of him! The pressure in his panties only increased.
“Edward, you are just the cutest thing in your darling little tights and Mary Janes! I love it!” Lily agreed.
“What do we say, dear?” his aunt prodded sweetly.
Blushing even more, Edward stammered softly in an uneven voice, “Thank you.”
Aunt Patricia only smiled proudly, as if Lily and Hannah’s reaction were exactly the sort of public admiration she intended. “Thank you, girls,” she said. “He is precious, isn’t he?”
Edward stared down at his melting ice cream, cheeks blazing, while his classmates giggled again. Finally, they let him sit back down and moved to the counter to place their orders.
“See you at school!” Hannah said cheerily as they walked away.
This was his last week of school before the summer break, but there were still two days left. Mercifully, Thursday was the last day, but there was no way this would be forgotten. With a sinking feeling, Edward watched Lily and Hannah whispering together at the counter, with sudden little bursts of laughter that made him flinch. His cheeks heated again, and his stomach turned cold as he realized the portrait was no longer something hidden away in the studio. Now it had escaped into the world where his classmates lived, and he could not call it back.
The next morning, Edward was on pins and needles as he walked into school. He saw Lily and Hannah in the hallway right away, as if they had been waiting for him. Edward was thankfully in ordinary clothes now, with no dress, no hairbow, and no nail polish. Still, he blushed as soon as he saw them. They came right over to him.
“Aww you look so plain and ordinary today, sweetie,” Hannah teased quietly, “But don’t worry, we’re not going to tell… everybody.”
Lily said somewhat guiltily, “I thought you should know, however, that I did let it slip to Sophie. I didn’t mean to but she saw me looking at the picture on my phone. I made her promise not to tell anyone else.”
This latest revelation lodged in Edward’s stomach like a stone. He stood awkwardly in front of the girls with his hands nervously half tucked into his pockets. Sophie was in his own grade and usually sat three tables away from him at lunch. He stifled a groan.
Over the next two days, Edward tried to tell himself that nothing had changed. School was nearly over, and everyone was distracted by yearbooks, summer plans and their final restless classes. But once he was watching for it, he could not stop noticing the signs.
Later in the afternoon, Sophie caught him by his locker with a knowing smile. Sophie stepped just close enough that he could hear her without anyone else catching every word. “Lily showed me your pictures,” she said with a smile, and Edward’s face went hot at once.
Before he could retreat into embarrassment, Sophie lifted one hand in a small, calming gesture. “I’m not going to make fun of you, Edward.” Her voice was soft and interested, “I only told Rachel, because she saw me react and asked what was going on, but I made her promise not to say anything either.”
Edward stared at the locker vent, too flustered to answer.
Sophie gave him a small, encouraging smile. “For what it’s worth, you looked darling,” she added, then seemed to realize how easily that might sound like teasing. “This whole thing must feel strange.” She glanced down the hallway to be sure no one was listening too closely.
“Please don’t tell anyone else,” he pleaded. Sophie nodded, “I won’t,” she said. “Rachel won’t either. Your secret is safe with us.” Then, with a gentle grin, “But I’d love to see you dressed up in person sometime.”
Despite all the assurances, on Thursday morning two other eight grade girls suddenly went quiet when he walked near them. They dissolved into giggles as soon as he passed. He realized that Hannah’s promise not to tell “everyone” was obviously not the same as telling “no one.”
No one other than Sophie said anything to him directly, however. That was almost worse. If someone had teased him plainly, perhaps he could have denied it or pretended not to care. Edward wished desperately that Lily and Hannah had never walked into that ice cream shop.
8
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 23, 2026, 11:27:37 AM »
The Next Sitting
Edward’s third sitting came the following Tuesday, and Edward entered the studio with a bit of a worried frown. Aunt Patricia had insisted he wear his new yellow frock to show Miss Vale and Mrs. Bell. Today, however, he was back in his pristine white tights instead of his adorably frilly lace anklet socks. The cool, clingy fabric of his tights slid electrically over his legs as he walked.
As they again had passed the playground, several young boys were organizing a game of tag near the low wall. He paused at the sound of their voices, wanting to watch but fearing they would notice him. One of the boys kicked up a puff of dust as he ran, and Edward felt an almost physical longing for that dust. In his mind, dust meant motion and carelessness. He sighed as he realized how far away that kind of thing seemed to him now.
His new dress seemed to make the walk even worse. Even with the pink dress’s ruffled sleeves, it was still a bit simpler and more demure. In contrast, this yellow one was undeniably frilly and girlish. Its adorable puffed sleeves gathered sweetly around his slender arms, and its lace ruffles practically floated as he moved. The bright satin sash caught the light, and the little embroidered flowers near the hem seemed designed to attract attention from the people Edward most wished would not look.
Aunt Patricia walked on his other side, openly pleased. “That sunshine color suits you so nicely, dear,” she said. “It brings out the softness in your face and draws the eye nicely.”
Edward stared down at the path dejectedly. “I was hoping not to… not to draw a lot of attention… Aunt Patricia,” he stammered weakly. It was as close as he dared come to a complaint.
“No?” she asked, untroubled. “How charming! That’s even more reason to put you in it, darling… a delicate and shy flower should be admired.”
His mother’s guiding hand rested on his shoulder, and Edward kept walking, feeling as if the playground was calling him. Again, he imagined darting over just for a few moments to try the swings or the monkey bars.
“This way honey,” his mother said softly, as if she had heard the thought. She turned him a fraction toward the studio. “Your adorable dress shouldn’t be anywhere near that dusty field.” Edward hated how dainty that sounded.
Upstairs in the studio, Miss Vale noticed at once that Edward seemed quieter than usual. His yellow dress immediately drew everyone’s eye. Its bright color made him feel visible even before anyone spoke, and every rustle of his skirt seemed to announce that he had once again arrived.
“What a cheerful dress,” Miss Vale said gently, though her voice stayed professional.
Mrs. Bell gave his outfit a quick, practical appraisal. “Oh, how darling, my dear. Don’t you feel so lovely?”
Edward hesitated. The question seemed so awkward. Then, he gave a small nod and said shyly, “I suppose.”
Aunt Patricia smiled as if that settled everything. “He does look sweet, doesn’t he?”
Edward looked down at his shoes.
“Well, let’s get started, shall we?” Miss Vale said. “The sooner we prepare, the sooner you can settle into your pose.”
Edward followed Mrs. Bell toward the dressing area, trying to steady himself. He knew the routine now—the careful hair, the old gown, the still chair, the long minutes of being studied. But knowing it did not make it easier. The yellow dress was only the beginning of the afternoon, and already he felt tired of being looked at.
Once again, Edward went through the elaborate dressing ritual. He felt defeated as Mrs. Bell did his delicate makeup and made sure his curls were perfect. Soon, Miss Vale began to mix paint on her palette and seemed to pick up on his subdued demeanor.
Once he was securely encased in his great-great grandmother’s old Victorian dress and properly made up, Miss Vale spoke again. “Some days are more challenging than others, Master Edward,” she offered, “but we will press on together.”
For twenty minutes, Edward stared past Miss Vale’s shoulder at a crack in the plaster and felt every unfairness in the world gather inside him like steam. Why did portraits require the person in them to do so much work? Why did he have to look so delicate and girlish? Most importantly, why had his aunt pushed him so deliberately onto this feminine path? And why was he just accepting it? The shrieks of laughter and play from outside seemed particularly boisterous today.
Edward’s thoughts kept circling back to Aunt Patricia’s overbearing certainty. At first, he had tried to believe that all of this was for the portrait. It was strange and embarrassing, but it had a clear purpose and, he hoped, an end. Yet lately that hope had begun to feel less steady. Aunt Patricia treated his dresses as though they should be his normal wardrobe. She seemed to relish his curls and polished nails as though they were improvements rather than preparations. Edward tried to imagine where this all might lead, and the picture unsettled him. This portrait seemed to be spreading outward until it touched every part of his life. The excuse of the portrait had seemingly given her permission to stop hinting and go after an outcome she really intended.
Edward’s third sitting came the following Tuesday, and Edward entered the studio with a bit of a worried frown. Aunt Patricia had insisted he wear his new yellow frock to show Miss Vale and Mrs. Bell. Today, however, he was back in his pristine white tights instead of his adorably frilly lace anklet socks. The cool, clingy fabric of his tights slid electrically over his legs as he walked.
As they again had passed the playground, several young boys were organizing a game of tag near the low wall. He paused at the sound of their voices, wanting to watch but fearing they would notice him. One of the boys kicked up a puff of dust as he ran, and Edward felt an almost physical longing for that dust. In his mind, dust meant motion and carelessness. He sighed as he realized how far away that kind of thing seemed to him now.
His new dress seemed to make the walk even worse. Even with the pink dress’s ruffled sleeves, it was still a bit simpler and more demure. In contrast, this yellow one was undeniably frilly and girlish. Its adorable puffed sleeves gathered sweetly around his slender arms, and its lace ruffles practically floated as he moved. The bright satin sash caught the light, and the little embroidered flowers near the hem seemed designed to attract attention from the people Edward most wished would not look.
Aunt Patricia walked on his other side, openly pleased. “That sunshine color suits you so nicely, dear,” she said. “It brings out the softness in your face and draws the eye nicely.”
Edward stared down at the path dejectedly. “I was hoping not to… not to draw a lot of attention… Aunt Patricia,” he stammered weakly. It was as close as he dared come to a complaint.
“No?” she asked, untroubled. “How charming! That’s even more reason to put you in it, darling… a delicate and shy flower should be admired.”
His mother’s guiding hand rested on his shoulder, and Edward kept walking, feeling as if the playground was calling him. Again, he imagined darting over just for a few moments to try the swings or the monkey bars.
“This way honey,” his mother said softly, as if she had heard the thought. She turned him a fraction toward the studio. “Your adorable dress shouldn’t be anywhere near that dusty field.” Edward hated how dainty that sounded.
Upstairs in the studio, Miss Vale noticed at once that Edward seemed quieter than usual. His yellow dress immediately drew everyone’s eye. Its bright color made him feel visible even before anyone spoke, and every rustle of his skirt seemed to announce that he had once again arrived.
“What a cheerful dress,” Miss Vale said gently, though her voice stayed professional.
Mrs. Bell gave his outfit a quick, practical appraisal. “Oh, how darling, my dear. Don’t you feel so lovely?”
Edward hesitated. The question seemed so awkward. Then, he gave a small nod and said shyly, “I suppose.”
Aunt Patricia smiled as if that settled everything. “He does look sweet, doesn’t he?”
Edward looked down at his shoes.
“Well, let’s get started, shall we?” Miss Vale said. “The sooner we prepare, the sooner you can settle into your pose.”
Edward followed Mrs. Bell toward the dressing area, trying to steady himself. He knew the routine now—the careful hair, the old gown, the still chair, the long minutes of being studied. But knowing it did not make it easier. The yellow dress was only the beginning of the afternoon, and already he felt tired of being looked at.
Once again, Edward went through the elaborate dressing ritual. He felt defeated as Mrs. Bell did his delicate makeup and made sure his curls were perfect. Soon, Miss Vale began to mix paint on her palette and seemed to pick up on his subdued demeanor.
Once he was securely encased in his great-great grandmother’s old Victorian dress and properly made up, Miss Vale spoke again. “Some days are more challenging than others, Master Edward,” she offered, “but we will press on together.”
For twenty minutes, Edward stared past Miss Vale’s shoulder at a crack in the plaster and felt every unfairness in the world gather inside him like steam. Why did portraits require the person in them to do so much work? Why did he have to look so delicate and girlish? Most importantly, why had his aunt pushed him so deliberately onto this feminine path? And why was he just accepting it? The shrieks of laughter and play from outside seemed particularly boisterous today.
Edward’s thoughts kept circling back to Aunt Patricia’s overbearing certainty. At first, he had tried to believe that all of this was for the portrait. It was strange and embarrassing, but it had a clear purpose and, he hoped, an end. Yet lately that hope had begun to feel less steady. Aunt Patricia treated his dresses as though they should be his normal wardrobe. She seemed to relish his curls and polished nails as though they were improvements rather than preparations. Edward tried to imagine where this all might lead, and the picture unsettled him. This portrait seemed to be spreading outward until it touched every part of his life. The excuse of the portrait had seemingly given her permission to stop hinting and go after an outcome she really intended.
9
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sweet baby katie on August 23, 2026, 09:49:38 AM »
masterfully told. A slow unfolding inexorably driven by the immersion into the pleasures of feminine dressing. A delight to read. Thank you.
10
Active Sissy Stories / Re: Baby Cindy III: Lovey Dovey Diaper Butt
« Last post by sweet baby katie on August 23, 2026, 09:16:20 AM »
Please continue. Does Baby Cindy have any pretty baby dresses? What panties does her Mommy dress her in? Is she ever put in cloth nappies? What occassioned Baby Cindy’s regression and feminization?
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