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Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on Yesterday at 08:49:50 PM »
A Stop at the Coffee Shop
Soon, they were all in Aunt Patricia’s car for the ride to the city. After about twenty minutes, Aunt Patricia decided they should stop along the way for a light breakfast. She parked her sedan in front of a tidy little coffee shop with striped awnings and pots of red geraniums beside the door. When Edward reluctantly followed his mother and aunt inside, a little gust of fragrant air met him. The shop smelled of fresh coffee, toasted bread and the faint cinnamon sweetness of pastries and muffins. Cups clinked against saucers, and a low murmur of adult voices filled the room beneath the soft scrape of chair legs on the tile.
Edward was painfully aware of the way he was dressed, and he was conscious of the neat click of his Mary Janes on the polished floor. His aunt ordered breakfast sandwiches for all of them, and they sat at a cheery table near the window to eat. He perched carefully on the chair, feeling as if everyone was looking at him. He was clearly dressed more fancily than anyone else in the shop this Saturday morning.
They had only taken a few bites when the bell over the door jingled, and a small crowd came in from the sidewalk. Five boys about Edward’s age entered, laughing and talking over one another, all of them wearing baseball uniforms with dark caps, and their names stitched across the back of their jerseys. A few parents followed, herding them along for a quick breakfast. From the lively conversation, it was obvious they were on their way to a baseball game.
“I’m telling you, Coach said I might get to pitch today!” one boy insisted.
“Only if you stop walking people,” another shot back, and the others laughed.
Edward froze with his sandwich halfway to his mouth. The contrast between him and these boys struck him so sharply that he nearly forgot to chew. He was suddenly very aware of his polished nails glinting pink as he held his food. These boys looked so carefree. Their uniforms were clean now but would undoubtably get scuffed and dirty later. Edward, by comparison, sat in a charming yellow frock with his frilly socks ruffling above shiny black shoes. His corset pressed steadily around his middle, and the bright shop made him feel so displayed. “Mother,” he whispered, barely moving his lips, “do we have to stay here?”
His mother glanced toward the other boys, then gave him a gentle look. “Just eat your breakfast, sweetheart,” she said quietly, “no one is going to bother you.” After a pause, she lowered her voice further and added, “Don’t stare at them like that, dear.” She added, “keep your napkin in your lap, and you’ll be fine.”
Aunt Patricia smiled over the rim of her coffee cup, and she spoke in a normal tone of voice, “Oh Edward, you darling little buttercup, there’s nothing to be embarrassed about. You look perfectly sweet!”
Edward’s breakfast sandwich suddenly seemed much harder to eat neatly. He lowered it at once, afraid of dropping crumbs. Why did she have to call his name so loudly like that?!
Soon, the boys noticed him, of course. How could they not? One of them glanced over, his eyes moving from Edward’s yellow bow to the puffed sleeves and down to the polished black Mary Janes beneath the table.
Another boy had evidently heard his aunt say his name. He leaned close to his friend and whispered, “Is that a boy?”
His friend whispered back, “It can’t be!” But he didn’t look convinced, “Did she say ‘Edward’?
The two of them smothered quick grins as they tried not to laugh before one of their mothers quickly scolded them. “Leave her alone,” the mother murmured, then, after a brief uncertain glance at Edward, corrected herself awkwardly, “I mean—leave that child alone and behave yourselves!”
Mrs. Gray’s face tightened slightly, but she forced a polite little smile across the room. “Ignore them, sweetheart… those... 'baseball boys' don’t understand how brave you are being.”
No one said anything directly to Edward, but that almost made it worse. Their silence felt full of questions, and every clink of a cup seemed suddenly louder. He looked down at his lap, cheeks burning, while Aunt Patricia dabbed delicately at the corner of her mouth and seemed not to notice—or perhaps noticed very well and was perfectly fine with it.
“Please, Aunty,” Edward mumbled, “can we go soon?”
Aunt Patricia set down her cup with serene patience. “After you finish, dear. A young lady does not bolt from a room merely because she has been noticed, and you need your breakfast.”
Chastened, Edward listened enviously to the boys’ excited talk of the game ahead while his own day stretched before him. Quiet museum galleries and lace-trimmed exhibits loomed in his future. For some reason, his mother's stilted description of them as "baseball boys" lodged itself in his brain.
When they finally finished eating, Aunt Patricia gathered her handbag, but she seemed to take her time doing it. “There now,” she said at last. “Off we go. We mustn’t waste any more of the morning.”
Edward stood carefully, smoothing the front of his yellow dress and trying not to look toward the "baseball boys." Unfortunately, their crowded table stood directly between him and the door. There was no other way out.
He followed his mother and aunt toward the narrow space between the tables. The boys' table was a bright, disorderly island of baseball caps, crumpled napkins, orange juice cartons and excited voices. One of the "baseball boys" scooted his chair to the side so Edward, his mother and his aunt could get through. As Edward passed, their raucous table went noticeably quiet. Edward could feel their eyes on him and he blushed again.
“Good luck in your sporting match today,” Edward’s mother said politely as they squeezed past. The awkwardness of her wording was obvious, and it only seemed to reinforce how little their worlds had in common. Clearly, she knew little about sports.
Aunt Patricia, realizing Edward was almost shrinking beside her, added in a clear voice directed at him, “Come along, my dear… we have a busy day ahead at the museum!”
Then, one of the fathers smiled a bit clumsily, but still his response was pleasant and kind, “Thanks, and you… ladies have a great day too.” Albeit with some eye-rolling, the boys in the baseball uniforms murmured a series of “Thanks” and “Thank you’s” as well when he gave them a stern look.
Edward kept his gaze lowered meekly, and Aunt Patricia’s hand settled lightly between his shoulders, guiding him forward. Her gentle but resolute touch reminded him that he was unmistakably under her supervision and exactly where he would be for the day. By the time the coffee shop door closed behind them, Edward’s cheeks were hot, his throat felt tight, and the lively voices of the "baseball boys" had already risen again, as though he had passed through their world just long enough to be reminded that it was not his.
The rest of the drive into the city passed in a heavy quiet for Edward. Aunt Patricia chatted cheerfully with his mother about traffic, the portrait and of course the museum. Edward, however, kept seeing the baseball boys’ crowded table in his mind as he recalled how their energetic laughter and chatter had started back up the instant he passed. The scene replayed itself in his mind: the boys in their team caps with elbows and crumbs on the table, the sudden hush as he came near, and then the burst of voices returning behind him as the door swung shut. He relived the way one of the "baseball boys" had quickly averted his eyes and stifled a giggle as Edward passed. The memory made his cheeks warm all over again.
Soon, they were all in Aunt Patricia’s car for the ride to the city. After about twenty minutes, Aunt Patricia decided they should stop along the way for a light breakfast. She parked her sedan in front of a tidy little coffee shop with striped awnings and pots of red geraniums beside the door. When Edward reluctantly followed his mother and aunt inside, a little gust of fragrant air met him. The shop smelled of fresh coffee, toasted bread and the faint cinnamon sweetness of pastries and muffins. Cups clinked against saucers, and a low murmur of adult voices filled the room beneath the soft scrape of chair legs on the tile.
Edward was painfully aware of the way he was dressed, and he was conscious of the neat click of his Mary Janes on the polished floor. His aunt ordered breakfast sandwiches for all of them, and they sat at a cheery table near the window to eat. He perched carefully on the chair, feeling as if everyone was looking at him. He was clearly dressed more fancily than anyone else in the shop this Saturday morning.
They had only taken a few bites when the bell over the door jingled, and a small crowd came in from the sidewalk. Five boys about Edward’s age entered, laughing and talking over one another, all of them wearing baseball uniforms with dark caps, and their names stitched across the back of their jerseys. A few parents followed, herding them along for a quick breakfast. From the lively conversation, it was obvious they were on their way to a baseball game.
“I’m telling you, Coach said I might get to pitch today!” one boy insisted.
“Only if you stop walking people,” another shot back, and the others laughed.
Edward froze with his sandwich halfway to his mouth. The contrast between him and these boys struck him so sharply that he nearly forgot to chew. He was suddenly very aware of his polished nails glinting pink as he held his food. These boys looked so carefree. Their uniforms were clean now but would undoubtably get scuffed and dirty later. Edward, by comparison, sat in a charming yellow frock with his frilly socks ruffling above shiny black shoes. His corset pressed steadily around his middle, and the bright shop made him feel so displayed. “Mother,” he whispered, barely moving his lips, “do we have to stay here?”
His mother glanced toward the other boys, then gave him a gentle look. “Just eat your breakfast, sweetheart,” she said quietly, “no one is going to bother you.” After a pause, she lowered her voice further and added, “Don’t stare at them like that, dear.” She added, “keep your napkin in your lap, and you’ll be fine.”
Aunt Patricia smiled over the rim of her coffee cup, and she spoke in a normal tone of voice, “Oh Edward, you darling little buttercup, there’s nothing to be embarrassed about. You look perfectly sweet!”
Edward’s breakfast sandwich suddenly seemed much harder to eat neatly. He lowered it at once, afraid of dropping crumbs. Why did she have to call his name so loudly like that?!
Soon, the boys noticed him, of course. How could they not? One of them glanced over, his eyes moving from Edward’s yellow bow to the puffed sleeves and down to the polished black Mary Janes beneath the table.
Another boy had evidently heard his aunt say his name. He leaned close to his friend and whispered, “Is that a boy?”
His friend whispered back, “It can’t be!” But he didn’t look convinced, “Did she say ‘Edward’?
The two of them smothered quick grins as they tried not to laugh before one of their mothers quickly scolded them. “Leave her alone,” the mother murmured, then, after a brief uncertain glance at Edward, corrected herself awkwardly, “I mean—leave that child alone and behave yourselves!”
Mrs. Gray’s face tightened slightly, but she forced a polite little smile across the room. “Ignore them, sweetheart… those... 'baseball boys' don’t understand how brave you are being.”
No one said anything directly to Edward, but that almost made it worse. Their silence felt full of questions, and every clink of a cup seemed suddenly louder. He looked down at his lap, cheeks burning, while Aunt Patricia dabbed delicately at the corner of her mouth and seemed not to notice—or perhaps noticed very well and was perfectly fine with it.
“Please, Aunty,” Edward mumbled, “can we go soon?”
Aunt Patricia set down her cup with serene patience. “After you finish, dear. A young lady does not bolt from a room merely because she has been noticed, and you need your breakfast.”
Chastened, Edward listened enviously to the boys’ excited talk of the game ahead while his own day stretched before him. Quiet museum galleries and lace-trimmed exhibits loomed in his future. For some reason, his mother's stilted description of them as "baseball boys" lodged itself in his brain.
When they finally finished eating, Aunt Patricia gathered her handbag, but she seemed to take her time doing it. “There now,” she said at last. “Off we go. We mustn’t waste any more of the morning.”
Edward stood carefully, smoothing the front of his yellow dress and trying not to look toward the "baseball boys." Unfortunately, their crowded table stood directly between him and the door. There was no other way out.
He followed his mother and aunt toward the narrow space between the tables. The boys' table was a bright, disorderly island of baseball caps, crumpled napkins, orange juice cartons and excited voices. One of the "baseball boys" scooted his chair to the side so Edward, his mother and his aunt could get through. As Edward passed, their raucous table went noticeably quiet. Edward could feel their eyes on him and he blushed again.
“Good luck in your sporting match today,” Edward’s mother said politely as they squeezed past. The awkwardness of her wording was obvious, and it only seemed to reinforce how little their worlds had in common. Clearly, she knew little about sports.
Aunt Patricia, realizing Edward was almost shrinking beside her, added in a clear voice directed at him, “Come along, my dear… we have a busy day ahead at the museum!”
Then, one of the fathers smiled a bit clumsily, but still his response was pleasant and kind, “Thanks, and you… ladies have a great day too.” Albeit with some eye-rolling, the boys in the baseball uniforms murmured a series of “Thanks” and “Thank you’s” as well when he gave them a stern look.
Edward kept his gaze lowered meekly, and Aunt Patricia’s hand settled lightly between his shoulders, guiding him forward. Her gentle but resolute touch reminded him that he was unmistakably under her supervision and exactly where he would be for the day. By the time the coffee shop door closed behind them, Edward’s cheeks were hot, his throat felt tight, and the lively voices of the "baseball boys" had already risen again, as though he had passed through their world just long enough to be reminded that it was not his.
The rest of the drive into the city passed in a heavy quiet for Edward. Aunt Patricia chatted cheerfully with his mother about traffic, the portrait and of course the museum. Edward, however, kept seeing the baseball boys’ crowded table in his mind as he recalled how their energetic laughter and chatter had started back up the instant he passed. The scene replayed itself in his mind: the boys in their team caps with elbows and crumbs on the table, the sudden hush as he came near, and then the burst of voices returning behind him as the door swung shut. He relived the way one of the "baseball boys" had quickly averted his eyes and stifled a giggle as Edward passed. The memory made his cheeks warm all over again.
2
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Yesterday at 10:14:21 AM »
Chapter 386.
“Thank you, Violet. No problems, I hope?”
“Not at all, not at all. I just wanted to run something past you, that’s all. You probably won’t be interested. I know how busy you are with coaching these days…”
“Oh, it’s not bad. Just whipping them into shape, that’s all…”
Violet allowed herself a wry smile, and glanced at Charlotte’s long dressage whip.
“Really? Well, that leads me neatly to my subject. I’ll be frank. We don’t have any secrets from each other, after all. Thomasina Middiford.”
“Oh! The talk of the stables! Have you heard the rumours?”
“I probably started some of them, dear…”
They giggled like schoolgirls.
“So, what about her. She’s out there now, in the field, giving a group of newbies a tour. Today it’s yellow latex. You should see their faces!”
“I bet. Well, I’ll tell you. Coco – you know Coco – suggested I use her to help out Bobby in the boot parlour.”
Charlotte’s eyes widened. “What a good idea! The poor boy’s worked off his feet. I was there a couple of days ago and the waiting room was so busy! So… Would you have her working alongside him, or…”
“I was thinking of a trial period first, just giving her one day a week by herself. But I’m rather afraid of leaving her alone with the boys. You understand?”
“Absolutely. They could eat her alive!”
“Well, I was rather hoping it would be the opposite…”
“Violet! Really!”
Another outburst of giggles.
“It would just be a trial period. But I have no-one I could ask to supervise…”
“Which day were you thinking…?”
“Maybe Wednesday. Give Bobby a mid-week break.”
“Would you like me…?”
“Would you? If only till I found someone else…”
“Oh, I might be in for the long haul. Depends how…entertaining it proves to be…”
“I’m so grateful…”
“No need, Violet.” She licked her lips. “I like a bit of live action. If you’re content to put me totally in charge…”
“Of course!”
“Then let’s give it a go. It could be fun. I’ll be like a mistress of ceremonies… Maybe I should bring my bullwhip…”
“I’m sure your dressage whip will be more than enough to keep everyone under control…”
“You’ll keep her in latex catsuits?”
“For the time being. I should ask Cynthia to come up with some new designs… And perhaps a cap. What can I call her? Coco suggested “boot slut”.”
“I like it. Or boot bitch. Let’s have a think. So we’re starting this Wednesday?”
“If you’re free.”
“I can’t wait. I’ll think about this further. I have to get going, but we’ll speak again tomorrow, yeah?”
“Yes. Okay, Charlotte. Thanks again. Oh, and if you see her on your way out, could you ask her to call in? I’ll give her the good news…”
Ten minutes later there was a nervous knock at the door, and in came Thomasina, resplendent in yellow latex and red riding gloves.
“Y-you wanted to see me, miss?”
“Thomasina! Sit down. Good girl. Yes, I have a new opening for you.”
“R-really, miss?”
“Yes, dear. I’d like you to assist Bobby in the boot parlour. You start on Wednesday. Initially there will be a trial period when you’ll be working alone. Don’t look so worried, dear. Charlotte Macilveney has generously offered to supervise. Isn’t that good of her?”
“Charlotte M-Macilveney? The dressage specialist?”
“Indeed.”
“B-but… I don’t have any experience… Nanny always used to clean my shoes when I was a little girl…”
Violet leant back in her chair and regarded Thomasina with smug satisfaction.
“But now you’re a grown-up girl, Thomasina, and you’ll be cleaning others’ boots. You’re the ideal candidate. If things work out I’ll get you some, er, appropriate uniforms. For the time being just wear one of your catsuits. This one is nice, actually. I haven’t seen you in yellow before. You should find it very rewarding work. We can discuss your contract and remuneration after the trial period. Any questions?”
She knew there was no point in arguing. Between the collections of Miss Poole and her erstwhile friend Emily Laidlaw there was enough material to ruin her life. She adopted a submissive tone.
“D-do I get any training, miss?”
“You can go and watch Bobby tomorrow. While you’re there you can also supervise the waiting room. I gather it’s very busy at present. Make sure everyone has their turn.”
She said this with a mischievous smile, envisaging her in her latex catsuit trying to control a roomful of unruly teenage girls. She sat silently looking at Thomasina for a whole minute, enjoying the way the latex clung to her figure, and imagining the reaction of the stable lads when they found out she was the new boot assistant.
“Yes, perfect…” she murmured.
“S-sorry, miss?”
“You can go now, Thomasina. Are you going home like that, by the way?”
“N-no… Mummy’s picking me up today.”
“Ah. Pity…”
“Thank you, Violet. No problems, I hope?”
“Not at all, not at all. I just wanted to run something past you, that’s all. You probably won’t be interested. I know how busy you are with coaching these days…”
“Oh, it’s not bad. Just whipping them into shape, that’s all…”
Violet allowed herself a wry smile, and glanced at Charlotte’s long dressage whip.
“Really? Well, that leads me neatly to my subject. I’ll be frank. We don’t have any secrets from each other, after all. Thomasina Middiford.”
“Oh! The talk of the stables! Have you heard the rumours?”
“I probably started some of them, dear…”
They giggled like schoolgirls.
“So, what about her. She’s out there now, in the field, giving a group of newbies a tour. Today it’s yellow latex. You should see their faces!”
“I bet. Well, I’ll tell you. Coco – you know Coco – suggested I use her to help out Bobby in the boot parlour.”
Charlotte’s eyes widened. “What a good idea! The poor boy’s worked off his feet. I was there a couple of days ago and the waiting room was so busy! So… Would you have her working alongside him, or…”
“I was thinking of a trial period first, just giving her one day a week by herself. But I’m rather afraid of leaving her alone with the boys. You understand?”
“Absolutely. They could eat her alive!”
“Well, I was rather hoping it would be the opposite…”
“Violet! Really!”
Another outburst of giggles.
“It would just be a trial period. But I have no-one I could ask to supervise…”
“Which day were you thinking…?”
“Maybe Wednesday. Give Bobby a mid-week break.”
“Would you like me…?”
“Would you? If only till I found someone else…”
“Oh, I might be in for the long haul. Depends how…entertaining it proves to be…”
“I’m so grateful…”
“No need, Violet.” She licked her lips. “I like a bit of live action. If you’re content to put me totally in charge…”
“Of course!”
“Then let’s give it a go. It could be fun. I’ll be like a mistress of ceremonies… Maybe I should bring my bullwhip…”
“I’m sure your dressage whip will be more than enough to keep everyone under control…”
“You’ll keep her in latex catsuits?”
“For the time being. I should ask Cynthia to come up with some new designs… And perhaps a cap. What can I call her? Coco suggested “boot slut”.”
“I like it. Or boot bitch. Let’s have a think. So we’re starting this Wednesday?”
“If you’re free.”
“I can’t wait. I’ll think about this further. I have to get going, but we’ll speak again tomorrow, yeah?”
“Yes. Okay, Charlotte. Thanks again. Oh, and if you see her on your way out, could you ask her to call in? I’ll give her the good news…”
Ten minutes later there was a nervous knock at the door, and in came Thomasina, resplendent in yellow latex and red riding gloves.
“Y-you wanted to see me, miss?”
“Thomasina! Sit down. Good girl. Yes, I have a new opening for you.”
“R-really, miss?”
“Yes, dear. I’d like you to assist Bobby in the boot parlour. You start on Wednesday. Initially there will be a trial period when you’ll be working alone. Don’t look so worried, dear. Charlotte Macilveney has generously offered to supervise. Isn’t that good of her?”
“Charlotte M-Macilveney? The dressage specialist?”
“Indeed.”
“B-but… I don’t have any experience… Nanny always used to clean my shoes when I was a little girl…”
Violet leant back in her chair and regarded Thomasina with smug satisfaction.
“But now you’re a grown-up girl, Thomasina, and you’ll be cleaning others’ boots. You’re the ideal candidate. If things work out I’ll get you some, er, appropriate uniforms. For the time being just wear one of your catsuits. This one is nice, actually. I haven’t seen you in yellow before. You should find it very rewarding work. We can discuss your contract and remuneration after the trial period. Any questions?”
She knew there was no point in arguing. Between the collections of Miss Poole and her erstwhile friend Emily Laidlaw there was enough material to ruin her life. She adopted a submissive tone.
“D-do I get any training, miss?”
“You can go and watch Bobby tomorrow. While you’re there you can also supervise the waiting room. I gather it’s very busy at present. Make sure everyone has their turn.”
She said this with a mischievous smile, envisaging her in her latex catsuit trying to control a roomful of unruly teenage girls. She sat silently looking at Thomasina for a whole minute, enjoying the way the latex clung to her figure, and imagining the reaction of the stable lads when they found out she was the new boot assistant.
“Yes, perfect…” she murmured.
“S-sorry, miss?”
“You can go now, Thomasina. Are you going home like that, by the way?”
“N-no… Mummy’s picking me up today.”
“Ah. Pity…”
3
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Yesterday at 10:00:03 AM »
Chapter 385.
Miss Poole’s eyes were sparkling as she dismissed Coco.
“Coco, you may have solved my problem. But I’ll have to sort out the details before I can be sure it’s viable. Thank you so much for your input. I’ll let you get back, now, but I promise to keep you in the loop.”
“Thank you, Miss Poole. My pleasure, I assure you.”
And she withdrew with an even smugger than usual expression on her face.
Miss Poole turned to Emily.
“Emily, what do you think? I feel stupid that it never occurred to me. I was thinking just in terms of boys.”
“Well there’s absolutely no reason why not.” She laughed. “Equal opportunities and all that. The lads will be delighted, and I bet a lot of the women will choose her too.”
“Do you think so?”
“Oh, I’m certain. It will add another dimension to the whole experience.”
“How do you think she’ll react to the suggestion?”
“She’ll do whatever we tell her to, Violet. Ever since she saw the video of that first party… She was terrified mummy might find out what a naughty girl she was. Look, we’ve already got her parading around everywhere in latex. I’ve watched her. She’s often deeply humiliated. But I honestly believe she gets a kick out of it. Those burning cheeks are partly embarrassment, partly arousal. Whatever her outward reaction, I’d be willing to bet that inwardly she’d be in a ferment of excitement and fear.”
“That’s so interesting. I hadn’t thought of her in quite those terms, but it makes perfect sense. She’s had a very sheltered upbringing, always had to be well-behaved and deferential to her elders, but harbours a powerful sex drive. It’s a perilous combination – for her, I mean...”
Emily Laidlaw smiled. “But it’s great for us…”
“Yes… But we have to be very careful here. There must be no possibility or even hint of abuse. You know what some of those lads are like… No. she must be willing and ready.” She looked thoughtful. “Initially, perhaps we should allocate her one weekday. Bobby can have a day off. He’d be so happy. Say Wednesday. But I would want to appoint a supervisor, to make sure the rules are strictly observed. Someone everyone respects… Someone with authority…”
“Don’t look at me, Violet…”
“No. Don’t worry… I know how busy you are.”
“Not that it wouldn’t be fun…”
“I’m sure. Just like one of your parties.”
“Shh…”
“You know who would be great? Though I’m not sure she would agree, or even be available.”
“Who?”
“Charlotte Macilveney.”
“The dressage queen? Wow. She’s very young.”
“She’s twenty-four.”
“Right. She’s incredibly popular. Would she even consider such a menial position?”
“I know Charlotte a little better than you, Emily. Don’t ever tell anyone, but she’s a client of ESDS. She’s quite…how can I put it? Broad-minded.”
“The county dressage champion. I had no idea…”
“I’ll give her a call. She’s coaching here today. She’d be perfect, of course. But I doubt she’d agree.”
“You never know… She’s a formidable young woman… And a dressage whip is a great persuader…”
Violet Poole got on the phone as soon as Emily had left.
“Charlotte… It’s Violet. Yes, well, thank you. You? Excellent. Would you have ten minutes to spare after work? About fourish? Great. See you then.”
Charlotte knocked at Miss Poole’s door just after four.
“Come in! Charlotte… Thank you for coming at such short notice. Now have a seat. I won’t keep you a few minutes.”
Miss Poole’s eyes were sparkling as she dismissed Coco.
“Coco, you may have solved my problem. But I’ll have to sort out the details before I can be sure it’s viable. Thank you so much for your input. I’ll let you get back, now, but I promise to keep you in the loop.”
“Thank you, Miss Poole. My pleasure, I assure you.”
And she withdrew with an even smugger than usual expression on her face.
Miss Poole turned to Emily.
“Emily, what do you think? I feel stupid that it never occurred to me. I was thinking just in terms of boys.”
“Well there’s absolutely no reason why not.” She laughed. “Equal opportunities and all that. The lads will be delighted, and I bet a lot of the women will choose her too.”
“Do you think so?”
“Oh, I’m certain. It will add another dimension to the whole experience.”
“How do you think she’ll react to the suggestion?”
“She’ll do whatever we tell her to, Violet. Ever since she saw the video of that first party… She was terrified mummy might find out what a naughty girl she was. Look, we’ve already got her parading around everywhere in latex. I’ve watched her. She’s often deeply humiliated. But I honestly believe she gets a kick out of it. Those burning cheeks are partly embarrassment, partly arousal. Whatever her outward reaction, I’d be willing to bet that inwardly she’d be in a ferment of excitement and fear.”
“That’s so interesting. I hadn’t thought of her in quite those terms, but it makes perfect sense. She’s had a very sheltered upbringing, always had to be well-behaved and deferential to her elders, but harbours a powerful sex drive. It’s a perilous combination – for her, I mean...”
Emily Laidlaw smiled. “But it’s great for us…”
“Yes… But we have to be very careful here. There must be no possibility or even hint of abuse. You know what some of those lads are like… No. she must be willing and ready.” She looked thoughtful. “Initially, perhaps we should allocate her one weekday. Bobby can have a day off. He’d be so happy. Say Wednesday. But I would want to appoint a supervisor, to make sure the rules are strictly observed. Someone everyone respects… Someone with authority…”
“Don’t look at me, Violet…”
“No. Don’t worry… I know how busy you are.”
“Not that it wouldn’t be fun…”
“I’m sure. Just like one of your parties.”
“Shh…”
“You know who would be great? Though I’m not sure she would agree, or even be available.”
“Who?”
“Charlotte Macilveney.”
“The dressage queen? Wow. She’s very young.”
“She’s twenty-four.”
“Right. She’s incredibly popular. Would she even consider such a menial position?”
“I know Charlotte a little better than you, Emily. Don’t ever tell anyone, but she’s a client of ESDS. She’s quite…how can I put it? Broad-minded.”
“The county dressage champion. I had no idea…”
“I’ll give her a call. She’s coaching here today. She’d be perfect, of course. But I doubt she’d agree.”
“You never know… She’s a formidable young woman… And a dressage whip is a great persuader…”
Violet Poole got on the phone as soon as Emily had left.
“Charlotte… It’s Violet. Yes, well, thank you. You? Excellent. Would you have ten minutes to spare after work? About fourish? Great. See you then.”
Charlotte knocked at Miss Poole’s door just after four.
“Come in! Charlotte… Thank you for coming at such short notice. Now have a seat. I won’t keep you a few minutes.”
4
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by bonzodoug on Yesterday at 12:26:06 AM »
Loving the story.
Will they notice he is getting excited?
What will they do about it?
Will they notice he is getting excited?
What will they do about it?
5
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by ace on August 09, 2026, 08:45:08 PM »
Yay, pictures ... isn't he pretty. Now all he needs is a little girlfriend to keep him company ;-) and to co-ordinate frocks!
Keep up the good work Sis.
Ace
Keep up the good work Sis.
Ace
6
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 09, 2026, 02:59:23 PM »
Getting Ready for Saturday
On the car ride home, Edward tried one last objection. “Aunty Patricia,” he began from the back seat, choosing each word carefully, “Do I have to wear… my dress on Saturday? Couldn’t I just wear something more… ordinary to the museum?”
Aunt Patricia glanced at him in the rearview mirror, clearly amused. “Ordinary?” she repeated. “My dear,” she said with a chuckle, “we are going into the city to attend a cultural exhibition, not running errands at the corner shop. And the goal is to help you develop that sense of ‘feminine stillness’ and appreciation for the fashion so important to your portrait!” She warmed to the subject almost immediately. “A well-mannered child must learn how to conduct himself properly in public places, and that of course means dressing appropriately for the occasion.”
Edward sank back against the seat, feeling the weekend closing around him. The museum had already seemed endless in his imagination, but now it seemed to stretch even longer. Edward stewed for the rest of Thursday and all day Friday at school. Normally, he would be eager for the freedom of the weekend, but instead he only dreaded Saturday morning and the looming trip to the city.
After school on Friday, his mother scrubbed him clean at home as if he were headed to a portrait sitting right then! She explained it was so they wouldn’t have to do so much to get ready when Aunt Patricia arrived on Saturday morning. His aunt had insisted they get an early start, and she would come to collect them first thing. His mother even washed and conditioned his hair, and then as he sat with a towel wrapping his damp hair, she took extra time to clip and file his nails for a pretty manicure.
When Edward awoke Saturday morning, he immediately noticed the fresh coat of pale pink polish and shiny clear topcoat his dainty nails now sported. He sighed deeply and pulled the cover back over his head. He didn’t want to get up. He of course was gloomily resigned to wearing his pretty pink dress again today to the museum for all the world to see. He was surprised when he heard Aunt Patricia arrive even earlier downstairs than he had expected. He hadn't even brushed his teeth!
Before he knew it, Aunt Patricia and his mother entered his room to help him get ready. He was still in his pajamas, and he couldn't help but notice that his aunt seemed to cast a disapproving look at them, as if she could barely resist tossing them out. Edward silently winced as he saw she was carrying a gray garment bag, and his mother was holding a white box tied with a yellow bow.
“You made such a fuss the other day about wearing your lovely pink dress, so I decided we could switch things up today!” She smiled as she said, "you won't have to wear it after all!"
Edward's eyes were now locked on the garment bag, and his stomach tightened as his aunt unzipped it.
“A small improvement,” she announced as she held up the garment. Edward was chagrined to see a lovely yellow party dress, softer and much more elaborate than the pink one, with a lacy collar, puffed sleeves, a satin sash, and tiny embroidered flowers scattered near the hem. His mother took the lid off the box as well to reveal a very lacy pair of yellow satin panties, some very frilly white ankle socks and a fancy yellow hairbow trimmed in lace scalloping. “For variety,” Aunt Patricia explained, “now you won’t have to wear the same outfit every time!”
Edward stared at it forlornly. “Wasn’t one dress enough, Aunt Patricia?” he asked softly.
Even this mild hint of protest seemed to perturb his Aunt Patricia, and her nose crinkled slightly. “Once I started looking, this one was simply too darling to pass up, sweetie,” she replied simply, “and you were the one who didn’t want to wear your pink one today.” Then, with an aura of authority she said brightly, “Let’s get it on you.”
So he wore it all: the yellow dress, the lacy white anklets, and the yellow panties along with his black patent Mary Janes. It was all meant to put him in the right mindset, and it was all making him feel more visible than ever. Once buttoned into his dress, he sat meekly while his mother brushed his soft, conditioned hair and then clamped his new satin yellow hairbow sweetly in place. She protected the hairbow with her hand and spritzed him with some sweet-smelling hairspray. Again, his corset hugged his torso snugly beneath the charming yellow frock, and he couldn’t help but notice that these panties tickled even more than his other pair. Aunt Patricia supervised these final touches with obvious approval.
Aunt Patricia gushed as Edward looked at himself in the mirror, and for a moment he could hardly look away. The yellow dress was brighter than the pink one had been, softer in color but somehow more visible. Its lacy collar framed his neck with a delicate whiteness, while the puffed sleeves rounded sweetly over his narrow shoulders and made his arms look smaller. The satin sash drew in at his waist before tying behind him in a fussy bow against his back. The skirt stood out prettily, brushing his knees in a light, swishing circle whenever he shifted his weight. The tiny flowers near the hem seemed almost childish. Edward blushed as he saw how incredibly girlish the lacy anklets, polished black Mary Janes, pink nail polish and dainty hairbow all looked together. From head to toe, he looked and felt so delicate and precious.
Aunt Patricia seemed practically delighted. She looked him over with open satisfaction, her eyes lingering on all his outfit’s charming details. “So lovely, dear!” she exclaimed. “Oh, Marian, just look at him. That color is perfect against his hair, and those sleeves are darling. I knew yellow would suit him, but this is even better than I expected.” Then she asked her nephew, with a smile that expected gratitude, “How do you like your new dress, sweetie?”
Edward paused for a second, and he felt his cheeks begin to warm. The dress felt light but inescapable, as if every ruffle had to find the most girlish way to settle. He could feel the lace trim of his satin panties against his thighs and the snug Mary Janes on his feet. Wearing the socks instead of his tights made him very conscious of the air against his legs. The scent of the hairspray lingered.
His mother, seeing him flounder, said softly, “What do we say, honey?”
Edward gulped, his cheeks growing pink as he lowered his eyes to the glossy toes of his shoes. “Thank you, Aunty,” he said shyly. “My… my new dress is very pretty.” Saying it aloud made the truth of it more humiliating: “MY new dress.” The worst part was how naturally the mirror seemed to agree with him. The white socks made his exposed legs look slender, and the puffed sleeves gave him a delicate, almost doll-like silhouette.
Aunt Patricia beamed as she heard the answer she wanted. “You’re quite welcome, my dear,” she said, resting her hand gently on his shoulder, “I’m so pleased that we have you appropriately attired now for our excursion.” She stepped back again and tilted her head to admire the sight of him. “Honestly, Marian, he looks like a little springtime flower, doesn’t he? So fresh and polished.”
Her glee made Edward feel even more sissyish, because it was not merely the dress she appreciated. He knew he was rapidly becoming the sort of child Aunt Patricia wanted to display.
“Turn once for Aunty, darling,” she said in a sweet but firm tone, and Edward obeyed with a miserable little pivot, the skirt flaring around his knees. Aunt Patricia gave a pleased sigh. “Absolutely adorable.”
On the car ride home, Edward tried one last objection. “Aunty Patricia,” he began from the back seat, choosing each word carefully, “Do I have to wear… my dress on Saturday? Couldn’t I just wear something more… ordinary to the museum?”
Aunt Patricia glanced at him in the rearview mirror, clearly amused. “Ordinary?” she repeated. “My dear,” she said with a chuckle, “we are going into the city to attend a cultural exhibition, not running errands at the corner shop. And the goal is to help you develop that sense of ‘feminine stillness’ and appreciation for the fashion so important to your portrait!” She warmed to the subject almost immediately. “A well-mannered child must learn how to conduct himself properly in public places, and that of course means dressing appropriately for the occasion.”
Edward sank back against the seat, feeling the weekend closing around him. The museum had already seemed endless in his imagination, but now it seemed to stretch even longer. Edward stewed for the rest of Thursday and all day Friday at school. Normally, he would be eager for the freedom of the weekend, but instead he only dreaded Saturday morning and the looming trip to the city.
After school on Friday, his mother scrubbed him clean at home as if he were headed to a portrait sitting right then! She explained it was so they wouldn’t have to do so much to get ready when Aunt Patricia arrived on Saturday morning. His aunt had insisted they get an early start, and she would come to collect them first thing. His mother even washed and conditioned his hair, and then as he sat with a towel wrapping his damp hair, she took extra time to clip and file his nails for a pretty manicure.
When Edward awoke Saturday morning, he immediately noticed the fresh coat of pale pink polish and shiny clear topcoat his dainty nails now sported. He sighed deeply and pulled the cover back over his head. He didn’t want to get up. He of course was gloomily resigned to wearing his pretty pink dress again today to the museum for all the world to see. He was surprised when he heard Aunt Patricia arrive even earlier downstairs than he had expected. He hadn't even brushed his teeth!
Before he knew it, Aunt Patricia and his mother entered his room to help him get ready. He was still in his pajamas, and he couldn't help but notice that his aunt seemed to cast a disapproving look at them, as if she could barely resist tossing them out. Edward silently winced as he saw she was carrying a gray garment bag, and his mother was holding a white box tied with a yellow bow.
“You made such a fuss the other day about wearing your lovely pink dress, so I decided we could switch things up today!” She smiled as she said, "you won't have to wear it after all!"
Edward's eyes were now locked on the garment bag, and his stomach tightened as his aunt unzipped it.
“A small improvement,” she announced as she held up the garment. Edward was chagrined to see a lovely yellow party dress, softer and much more elaborate than the pink one, with a lacy collar, puffed sleeves, a satin sash, and tiny embroidered flowers scattered near the hem. His mother took the lid off the box as well to reveal a very lacy pair of yellow satin panties, some very frilly white ankle socks and a fancy yellow hairbow trimmed in lace scalloping. “For variety,” Aunt Patricia explained, “now you won’t have to wear the same outfit every time!”
Edward stared at it forlornly. “Wasn’t one dress enough, Aunt Patricia?” he asked softly.
Even this mild hint of protest seemed to perturb his Aunt Patricia, and her nose crinkled slightly. “Once I started looking, this one was simply too darling to pass up, sweetie,” she replied simply, “and you were the one who didn’t want to wear your pink one today.” Then, with an aura of authority she said brightly, “Let’s get it on you.”
So he wore it all: the yellow dress, the lacy white anklets, and the yellow panties along with his black patent Mary Janes. It was all meant to put him in the right mindset, and it was all making him feel more visible than ever. Once buttoned into his dress, he sat meekly while his mother brushed his soft, conditioned hair and then clamped his new satin yellow hairbow sweetly in place. She protected the hairbow with her hand and spritzed him with some sweet-smelling hairspray. Again, his corset hugged his torso snugly beneath the charming yellow frock, and he couldn’t help but notice that these panties tickled even more than his other pair. Aunt Patricia supervised these final touches with obvious approval.
Aunt Patricia gushed as Edward looked at himself in the mirror, and for a moment he could hardly look away. The yellow dress was brighter than the pink one had been, softer in color but somehow more visible. Its lacy collar framed his neck with a delicate whiteness, while the puffed sleeves rounded sweetly over his narrow shoulders and made his arms look smaller. The satin sash drew in at his waist before tying behind him in a fussy bow against his back. The skirt stood out prettily, brushing his knees in a light, swishing circle whenever he shifted his weight. The tiny flowers near the hem seemed almost childish. Edward blushed as he saw how incredibly girlish the lacy anklets, polished black Mary Janes, pink nail polish and dainty hairbow all looked together. From head to toe, he looked and felt so delicate and precious.
Aunt Patricia seemed practically delighted. She looked him over with open satisfaction, her eyes lingering on all his outfit’s charming details. “So lovely, dear!” she exclaimed. “Oh, Marian, just look at him. That color is perfect against his hair, and those sleeves are darling. I knew yellow would suit him, but this is even better than I expected.” Then she asked her nephew, with a smile that expected gratitude, “How do you like your new dress, sweetie?”
Edward paused for a second, and he felt his cheeks begin to warm. The dress felt light but inescapable, as if every ruffle had to find the most girlish way to settle. He could feel the lace trim of his satin panties against his thighs and the snug Mary Janes on his feet. Wearing the socks instead of his tights made him very conscious of the air against his legs. The scent of the hairspray lingered.
His mother, seeing him flounder, said softly, “What do we say, honey?”
Edward gulped, his cheeks growing pink as he lowered his eyes to the glossy toes of his shoes. “Thank you, Aunty,” he said shyly. “My… my new dress is very pretty.” Saying it aloud made the truth of it more humiliating: “MY new dress.” The worst part was how naturally the mirror seemed to agree with him. The white socks made his exposed legs look slender, and the puffed sleeves gave him a delicate, almost doll-like silhouette.
Aunt Patricia beamed as she heard the answer she wanted. “You’re quite welcome, my dear,” she said, resting her hand gently on his shoulder, “I’m so pleased that we have you appropriately attired now for our excursion.” She stepped back again and tilted her head to admire the sight of him. “Honestly, Marian, he looks like a little springtime flower, doesn’t he? So fresh and polished.”
Her glee made Edward feel even more sissyish, because it was not merely the dress she appreciated. He knew he was rapidly becoming the sort of child Aunt Patricia wanted to display.
“Turn once for Aunty, darling,” she said in a sweet but firm tone, and Edward obeyed with a miserable little pivot, the skirt flaring around his knees. Aunt Patricia gave a pleased sigh. “Absolutely adorable.”
7
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 08, 2026, 05:45:27 PM »
To ace and RibbonBound,
Thank you for your nice comments. I appreciate the encouragement and I hope you are enjoying the additions to the story.
FYI I added an image of Edward in his darling blue knee suit and his doting aunt to the first chapter of his story :)
Thank you for your nice comments. I appreciate the encouragement and I hope you are enjoying the additions to the story.
FYI I added an image of Edward in his darling blue knee suit and his doting aunt to the first chapter of his story :)
8
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 08, 2026, 04:58:06 PM »
Edward's Second Sitting Ends in Surprise
“Let’s get you settled back in, my dear,” Miss Vale interjected, “we still have work ahead of us today.”
Once again, Edward was meekly placed and fastened back in his serenely girlish pose. As Miss Vale continued capturing the scene on canvas, Aunt Patricia seemed ever more animated. While she remained mostly quiet out of deference to Miss Vale, it was difficult for her to contain her satisfaction. She could not refrain from the occasional comment about his “feminine stillness.”
Edward did his best to ignore everything around him and sink into himself. Miss Vale painted on, but eventually, gratefully, he reached the end of the session. Thankfully, he had the weekend ahead of him. He wouldn’t have to pose for his next sitting until next week, and he was desperately looking forward to a break from dresses and ringlets. Although he was soon back in his darling pink frock and Mary Janes, he was relieved at least to be free of the heavy lilac velvet and all those petticoats.
As they prepared to leave the studio, Miss Vale spoke, almost as an afterthought, “I meant to mention this earlier, but there is a museum exhibit in the city that you all might find interesting in light of our current undertaking.”
“Oh really?” Aunt Patricia asked curiously, “what is it about?”
Something inside Edward twitched with suspicion.
“Well,” Miss Vale explained, “it’s actually an exhibition on period Victorian fashion, and it’s very well done. It’s called ‘Victorian Elegance: Women’s Fashion of the 19th Century’ and it’s quite stunning.” She went on, speaking to Edward, “Mrs. Bell and I drove over to see it last weekend in preparation for your portrait dear.”
Mrs. Bell added, “Oh yes, you really should take it in if you have the chance. I’m sure it would give you a greater understanding of the era’s style.” She added admiringly, “it showcases so many interesting fabrics and dressmaking styles that I confess I lost track of time.” She giggled, “I think they practically had to kick us out at closing time!”
Edward made a little face before he could stop himself. He could think of almost nothing less appealing. After a week of seemingly endless sittings inside Miss Vale’s studio, the last thing he wanted was to spend even more time staring at old dresses. In his mind, the exhibition would be a long, hushed hallway full of mannequins in stiff bodices and gloomy gowns, with tiny placards explaining bonnets, corsets, petticoats, and lace cuffs in exhausting detail. He already felt unsettled after being so carefully buttoned, pinned, curled and arranged like a museum piece himself.
The idea of being dragged through some stuffy museum just to look at Victorian gowns and frocks made him cringe, but the look on his aunt’s face gave him a sinking feeling. It sounded like such a sissy thing to do, but of course, as he was already dressed so daintily, that argument would carry no weight at all.
Aunt Patricia, however, seemed instantly enthralled by the notion and her eyes brightened. “Why, I think that would be lovely!” she exclaimed, already sounding as though the matter had progressed from possibility to plan. “Victorian women’s fashion! How perfectly appropriate. Imagine, Marian—all those gowns, all those delicate fabrics, the hats, the gloves, the crinolines and proper silhouettes. It would give Edward such a marvelous sense of the world he is helping us remember.” Turning eagerly to her sister she said, “we really should take Edward to see it! Wouldn’t you like to see it as well, Marian?”
Edward’s mother looked noncommittal and said, “Well I suppose… if we can find the right time.”
Aunt Patricia then turned an admiring look on Edward. Edward’s blush deepened as she continued, undeterred. “This would be a wonderful chance for you to see how young ladies of that era carried all those layers with dignity and charm. It might make you understand your own frocks and petticoats much better.” She smiled at him as though this were encouragement. With a patronizing smile, she asked, “what about it, sweetie?” She prodded him, “wouldn’t it be a nice way to really appreciate your great-great grandmother’s time while you’re working on your portrait?”
Edward turned beet-red. He wanted to protest that he had no interest in it, not the slightest, not even for a minute. He wanted to say that he had already seen enough satin, velvet, lace, and petticoats to last the rest of his life. But the way Aunt Patricia couched it made refusal hard. He stumbled over his words. “But… Aunty… I mean… I don’t think… I mean…” His voice thinned as soon as he saw Aunt Patricia’s determined expression. She had latched onto the idea. He looked helplessly at his mother, but she was already beginning to nod meekly in agreement.
Aunt Patricia continued brightly, “Oh come on, honey, it will be educational, and it’s only for a few hours. I’m sure it will help you in getting into the right state of mind for your sittings.” She leaned closer, her expression glowing with the sort of fond insistence Edward had learned to fear. “Besides, sweetie, you have already made such an encouraging start. Miss Vale sees it, Mrs. Bell sees it and I certainly see it. Then she fixed him with one of her smothering looks, and when she spoke again her tone was more insistent. “Don’t be such a ‘pouty Patty,’ sweetheart. Think of it as part of your project. A few hours among lovely Victorian dresses will do wonders for that feminine spirit you are cultivating.”
Edward felt her domineering gaze linger on his flushed face, his smoothed skirt, and the timid way he averted his eyes. Edward felt as if everyone in the room could see how nervous he was. His mouth was dry, and his fingers curled helplessly against the fabric of his darling dress.
Aunt Patricia’s voice softened with a patronizing sweetness, “What do you say, dear?”
Edward looked to his mother again, hoping for even the smallest sign that she might rescue him, but that hope faded instantly. Unfortunately, his mother’s look said everything he needed to know. He winced as he imagined Aunt Patricia reading every exhibit label aloud while he stood beside her in his dainty pink frock, trying not to attract stares from museum visitors. “Oh no!” he realized belatedly, his stomach dropping. “She’s going to put me in my dress for the museum too!” It made his cheeks burn even hotter, and he swallowed hard. Understanding this was not a fight he could win, he lowered his eyes and said softly, “OK… Aunty.”
“Wonderful!” she said, “I knew you’d see it my way!” Then, she gripped his chin firmly for a moment with surprising force to ensure she had his full attention, and he froze under her touch, too embarrassed to pull away and too nervous to meet her eyes. Edward’s face was already hot, but it seemed to grow hotter as she touched him. She slowly lifted her thumb and ran it ever so delicately over his quivering lips with a teasing comment, “you are so adorably precious!” Finally, she playfully patted his cheek with her fingers and said, “Good girl!” These last words landed with a humiliating little jolt.
Immediately, Edward grew lightheaded and felt a confusing rush of shame and nervousness. He immediately sensed an unwelcome tingling deep underneath his panties and tights. He drew several shallow breaths, still constricted by his corset, and tried desperately to compose himself before anyone noticed how rattled he was. His hands trembled faintly at his sides, and he pressed them against his pretty pink skirt to hide it.
Next, Aunt Patricia turned to Edward’s mother, “now we just have to decide on a time to visit.”
Miss Vale spoke again, “Oh, unfortunately I’m afraid you will have no choice but to go this weekend if you want to catch it.” She explained, “the exhibition ends Sunday.”
Aunt Patricia’s face lit up at once, as though the deadline made the whole thing even more exciting. “Then Saturday it shall be,” she declared. “We really can’t miss it, Marian. It would be a shame for Edward to never see more of the gowns that inspired our great-grandmother’s age.” She turned to Edward with bright, affectionate authority. “we’ll make a day of it!”
"Saturday," Edward repeated in his mind. Deflated, he understood his weekend would bring no break from his darling dresses.
“Let’s get you settled back in, my dear,” Miss Vale interjected, “we still have work ahead of us today.”
Once again, Edward was meekly placed and fastened back in his serenely girlish pose. As Miss Vale continued capturing the scene on canvas, Aunt Patricia seemed ever more animated. While she remained mostly quiet out of deference to Miss Vale, it was difficult for her to contain her satisfaction. She could not refrain from the occasional comment about his “feminine stillness.”
Edward did his best to ignore everything around him and sink into himself. Miss Vale painted on, but eventually, gratefully, he reached the end of the session. Thankfully, he had the weekend ahead of him. He wouldn’t have to pose for his next sitting until next week, and he was desperately looking forward to a break from dresses and ringlets. Although he was soon back in his darling pink frock and Mary Janes, he was relieved at least to be free of the heavy lilac velvet and all those petticoats.
As they prepared to leave the studio, Miss Vale spoke, almost as an afterthought, “I meant to mention this earlier, but there is a museum exhibit in the city that you all might find interesting in light of our current undertaking.”
“Oh really?” Aunt Patricia asked curiously, “what is it about?”
Something inside Edward twitched with suspicion.
“Well,” Miss Vale explained, “it’s actually an exhibition on period Victorian fashion, and it’s very well done. It’s called ‘Victorian Elegance: Women’s Fashion of the 19th Century’ and it’s quite stunning.” She went on, speaking to Edward, “Mrs. Bell and I drove over to see it last weekend in preparation for your portrait dear.”
Mrs. Bell added, “Oh yes, you really should take it in if you have the chance. I’m sure it would give you a greater understanding of the era’s style.” She added admiringly, “it showcases so many interesting fabrics and dressmaking styles that I confess I lost track of time.” She giggled, “I think they practically had to kick us out at closing time!”
Edward made a little face before he could stop himself. He could think of almost nothing less appealing. After a week of seemingly endless sittings inside Miss Vale’s studio, the last thing he wanted was to spend even more time staring at old dresses. In his mind, the exhibition would be a long, hushed hallway full of mannequins in stiff bodices and gloomy gowns, with tiny placards explaining bonnets, corsets, petticoats, and lace cuffs in exhausting detail. He already felt unsettled after being so carefully buttoned, pinned, curled and arranged like a museum piece himself.
The idea of being dragged through some stuffy museum just to look at Victorian gowns and frocks made him cringe, but the look on his aunt’s face gave him a sinking feeling. It sounded like such a sissy thing to do, but of course, as he was already dressed so daintily, that argument would carry no weight at all.
Aunt Patricia, however, seemed instantly enthralled by the notion and her eyes brightened. “Why, I think that would be lovely!” she exclaimed, already sounding as though the matter had progressed from possibility to plan. “Victorian women’s fashion! How perfectly appropriate. Imagine, Marian—all those gowns, all those delicate fabrics, the hats, the gloves, the crinolines and proper silhouettes. It would give Edward such a marvelous sense of the world he is helping us remember.” Turning eagerly to her sister she said, “we really should take Edward to see it! Wouldn’t you like to see it as well, Marian?”
Edward’s mother looked noncommittal and said, “Well I suppose… if we can find the right time.”
Aunt Patricia then turned an admiring look on Edward. Edward’s blush deepened as she continued, undeterred. “This would be a wonderful chance for you to see how young ladies of that era carried all those layers with dignity and charm. It might make you understand your own frocks and petticoats much better.” She smiled at him as though this were encouragement. With a patronizing smile, she asked, “what about it, sweetie?” She prodded him, “wouldn’t it be a nice way to really appreciate your great-great grandmother’s time while you’re working on your portrait?”
Edward turned beet-red. He wanted to protest that he had no interest in it, not the slightest, not even for a minute. He wanted to say that he had already seen enough satin, velvet, lace, and petticoats to last the rest of his life. But the way Aunt Patricia couched it made refusal hard. He stumbled over his words. “But… Aunty… I mean… I don’t think… I mean…” His voice thinned as soon as he saw Aunt Patricia’s determined expression. She had latched onto the idea. He looked helplessly at his mother, but she was already beginning to nod meekly in agreement.
Aunt Patricia continued brightly, “Oh come on, honey, it will be educational, and it’s only for a few hours. I’m sure it will help you in getting into the right state of mind for your sittings.” She leaned closer, her expression glowing with the sort of fond insistence Edward had learned to fear. “Besides, sweetie, you have already made such an encouraging start. Miss Vale sees it, Mrs. Bell sees it and I certainly see it. Then she fixed him with one of her smothering looks, and when she spoke again her tone was more insistent. “Don’t be such a ‘pouty Patty,’ sweetheart. Think of it as part of your project. A few hours among lovely Victorian dresses will do wonders for that feminine spirit you are cultivating.”
Edward felt her domineering gaze linger on his flushed face, his smoothed skirt, and the timid way he averted his eyes. Edward felt as if everyone in the room could see how nervous he was. His mouth was dry, and his fingers curled helplessly against the fabric of his darling dress.
Aunt Patricia’s voice softened with a patronizing sweetness, “What do you say, dear?”
Edward looked to his mother again, hoping for even the smallest sign that she might rescue him, but that hope faded instantly. Unfortunately, his mother’s look said everything he needed to know. He winced as he imagined Aunt Patricia reading every exhibit label aloud while he stood beside her in his dainty pink frock, trying not to attract stares from museum visitors. “Oh no!” he realized belatedly, his stomach dropping. “She’s going to put me in my dress for the museum too!” It made his cheeks burn even hotter, and he swallowed hard. Understanding this was not a fight he could win, he lowered his eyes and said softly, “OK… Aunty.”
“Wonderful!” she said, “I knew you’d see it my way!” Then, she gripped his chin firmly for a moment with surprising force to ensure she had his full attention, and he froze under her touch, too embarrassed to pull away and too nervous to meet her eyes. Edward’s face was already hot, but it seemed to grow hotter as she touched him. She slowly lifted her thumb and ran it ever so delicately over his quivering lips with a teasing comment, “you are so adorably precious!” Finally, she playfully patted his cheek with her fingers and said, “Good girl!” These last words landed with a humiliating little jolt.
Immediately, Edward grew lightheaded and felt a confusing rush of shame and nervousness. He immediately sensed an unwelcome tingling deep underneath his panties and tights. He drew several shallow breaths, still constricted by his corset, and tried desperately to compose himself before anyone noticed how rattled he was. His hands trembled faintly at his sides, and he pressed them against his pretty pink skirt to hide it.
Next, Aunt Patricia turned to Edward’s mother, “now we just have to decide on a time to visit.”
Miss Vale spoke again, “Oh, unfortunately I’m afraid you will have no choice but to go this weekend if you want to catch it.” She explained, “the exhibition ends Sunday.”
Aunt Patricia’s face lit up at once, as though the deadline made the whole thing even more exciting. “Then Saturday it shall be,” she declared. “We really can’t miss it, Marian. It would be a shame for Edward to never see more of the gowns that inspired our great-grandmother’s age.” She turned to Edward with bright, affectionate authority. “we’ll make a day of it!”
"Saturday," Edward repeated in his mind. Deflated, he understood his weekend would bring no break from his darling dresses.
9
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 07, 2026, 10:58:46 AM »
Chapter 384.
Given that the atmosphere at Connie’s is becoming rather claustrophobic and overheated, and safe in the knowledge that Tim himself is unlikely to be going anywhere in the immediate future, this may be a good time briefly to catch up on the activities of his best friend, who had figured so much in his thoughts recently. But as well as missing Bobby, Tim was also harbouring a faint jealousy, based on the misconception that Bobby, relative to he, was having an easy time of it. The truth was quite the opposite. While Tim was chained to his maid-tidy, he had just finished work, and was lying face-down on his bed, exhausted. Ellie was making supper for him. She was the only one who really cared for and looked after him.
“It’s not fair, Bobby. Why is it taking so long to find you an assistant? You can’t go on like this…”
He had been working overtime every day in a vain effort to reduce the backlog of bookings. It was the eighth of December, Christmas was looming, and everything was getting busier. The previous day, Sunday, there had been more kids than ever at the pony rides – and they had felt heavier than ever. But, though he didn’t yet know it, help was just around the corner.
Miss Poole knew she had to find someone to share the burden. ESDS had no-one suitable – or they didn’t want to release anyone – applicants to an online ad were largely (predictably) ageing perverts – so a week before she had posted a notice on the main notice board asking for volunteers.
It was pure chance that the Posh Triplets – Coco, Roxanne and Octavia, so-called not because they were related, but merely because at Pitt’s Wood they were rarely seen out of each other’s company, (see Chapter 293 et seq.) – were at a loose end the Thursday of that week, and had elected to have a morning’s trail-riding in the forest. On their return to the stables they passed through reception, and Octavia caught sight of the notice.
“See this, darling?” she laughed to Roxanne. “You should apply. You’d be perfect, cleaning boots for all the oiks!”
“Shut your face, sweaty pants,” came the pleasant retort. “Perfect for you…”
But Coco had had a thought. “Quiet, you two. You know who’d be perfect? No? That girl…what’s her name…yeah, Thomasina!”
They stared.
“That little sissy bitch? Just cos her mummy has a title…” sneered Roxanne, who hated Thomasina just because she had greater pretensions to “breeding” than she.
“Wouldn’t she just…” gasped Octavia, immediately grasping the possibilities. “And we owe her one… Do you still have that video of her in the forest?”
“I do,” said Coco. “But I’ll tell you what. Miss Laidlaw…I’ve heard she has something even better…something totally…”
“What?”
Coco lowered her voice. “Something pornographic! From her party… I heard it from a friend of my mum’s. Either way, we’ll get her. Just leave it to me, right?”
Coco was on the phone to Emily Laidlaw that very afternoon.
“Emily? Hi! How are you? It’s Coco… Yes, that’s right. I wondered if you’d be free for a quick coffee tomorrow. You normally ride on Fridays, right? What’s it about? Well, I may have an idea to help Miss Poole find someone for the boot parlour… Yes, it would be, wouldn’t it? Well I’d rather not say over the phone. Someone you know? Er, yes… Thomasina, actually… Great! See you about two, then.”
The mention of Thomasina’s name seemed to have done the trick. True, Emily Laidlaw had been quite friendly towards her. But she also had a well-developed sense of mischief, which everyone knew well. And if the rumours about those parties were true…
They met in the members’ canteen. They bought coffee and croissants and settled down in a side table.
“So, Coco… You have an idea involving Thomasina…”
“I just thought…imagine if Bobby had a female assistant. And somehow, straight away, I thought of Thomasina. I mean, they’re already acquainted…”
“Oh, yes. The Sunday pony rides…”
“Right. And you know how she loves to show off in those latex catsuits… These days hardly see her in anything else. Even though she must be so embarrassed…”
Miss Laidlaw smiled an enigmatic smile. “Yes… Well, I guess you can thank me for that…”
“You, Miss Laidlaw?”
“She pretty much does what I tell her these days. I have a certain amount of, ah, influence, shall we say?”
“Oh. I mean, I did hear some rumours…about the parties, and so on…”
“Did you now? What exactly did you hear? Are you blushing, darling?” She looked amused. “Dear me, I didn’t imagine you were so innocent…”
“I’m not, miss.” She leaned forward. “Is it true? Does she…?”
“Like a professional, darling. But she’s been well-trained.”
“Oh, gosh! It is true then!”
“If you’re a good girl I might show you a video…but not now. It’s a brilliant idea, Coco. I don’t know why I hadn’t thought of it. She’d be perfect! She’s a hopeless submissive… By the way, did you know those cute catsuits are usually equipped with an internal dil-do...or two?”
“I thought so! The way she rides…”
“We should go see Miss Poole together. Today! She’ll love it. She was the one who got Thomasina into latex originally. Imagine… I’ll be able to have her polish my boots anytime I want… Remind her what a slut she is… Show her a video of herself while she’s working!” She laughed out loud. “Oh, and I’ll tell you what!”
“What?”
“She can provide extra services… For the stable lads! That’ll be a new twist. The boot parlour will double its clientele overnight!”
“Miss…! You mean… That’s so gross…”
“It’s ideal! It’s what she does best. Let’s see if Violet’s in now.”
They finished their coffees and made their way to her office.
“Emily! Oh, and Coco. What can I do for you two?”
“I’ll let Coco explain. It was her idea.”
Miss Poole was delighted. “Wonderful! That’s a weight off my mind. The staff will be so happy. And not only the boys. There’s many here who’d love to take her down another peg or two. Having her down on her knees at their behest…”
“It’s her favourite position, Violet…”
“Miss Poole laughed. “Quite so, quite so… And we’ll have to get her a uniform or two… Cynthia will have some ideas… And a title… She could be a boot girl, I suppose…”
“How about boot slut,” suggested Coco, spitefully.
“Oh, perfect. Yes… Book now with our new boot slut, Thomasina Middiford…” She clapped her hands with delight. “And won’t Lady Middiford be proud…”
Given that the atmosphere at Connie’s is becoming rather claustrophobic and overheated, and safe in the knowledge that Tim himself is unlikely to be going anywhere in the immediate future, this may be a good time briefly to catch up on the activities of his best friend, who had figured so much in his thoughts recently. But as well as missing Bobby, Tim was also harbouring a faint jealousy, based on the misconception that Bobby, relative to he, was having an easy time of it. The truth was quite the opposite. While Tim was chained to his maid-tidy, he had just finished work, and was lying face-down on his bed, exhausted. Ellie was making supper for him. She was the only one who really cared for and looked after him.
“It’s not fair, Bobby. Why is it taking so long to find you an assistant? You can’t go on like this…”
He had been working overtime every day in a vain effort to reduce the backlog of bookings. It was the eighth of December, Christmas was looming, and everything was getting busier. The previous day, Sunday, there had been more kids than ever at the pony rides – and they had felt heavier than ever. But, though he didn’t yet know it, help was just around the corner.
Miss Poole knew she had to find someone to share the burden. ESDS had no-one suitable – or they didn’t want to release anyone – applicants to an online ad were largely (predictably) ageing perverts – so a week before she had posted a notice on the main notice board asking for volunteers.
It was pure chance that the Posh Triplets – Coco, Roxanne and Octavia, so-called not because they were related, but merely because at Pitt’s Wood they were rarely seen out of each other’s company, (see Chapter 293 et seq.) – were at a loose end the Thursday of that week, and had elected to have a morning’s trail-riding in the forest. On their return to the stables they passed through reception, and Octavia caught sight of the notice.
“See this, darling?” she laughed to Roxanne. “You should apply. You’d be perfect, cleaning boots for all the oiks!”
“Shut your face, sweaty pants,” came the pleasant retort. “Perfect for you…”
But Coco had had a thought. “Quiet, you two. You know who’d be perfect? No? That girl…what’s her name…yeah, Thomasina!”
They stared.
“That little sissy bitch? Just cos her mummy has a title…” sneered Roxanne, who hated Thomasina just because she had greater pretensions to “breeding” than she.
“Wouldn’t she just…” gasped Octavia, immediately grasping the possibilities. “And we owe her one… Do you still have that video of her in the forest?”
“I do,” said Coco. “But I’ll tell you what. Miss Laidlaw…I’ve heard she has something even better…something totally…”
“What?”
Coco lowered her voice. “Something pornographic! From her party… I heard it from a friend of my mum’s. Either way, we’ll get her. Just leave it to me, right?”
Coco was on the phone to Emily Laidlaw that very afternoon.
“Emily? Hi! How are you? It’s Coco… Yes, that’s right. I wondered if you’d be free for a quick coffee tomorrow. You normally ride on Fridays, right? What’s it about? Well, I may have an idea to help Miss Poole find someone for the boot parlour… Yes, it would be, wouldn’t it? Well I’d rather not say over the phone. Someone you know? Er, yes… Thomasina, actually… Great! See you about two, then.”
The mention of Thomasina’s name seemed to have done the trick. True, Emily Laidlaw had been quite friendly towards her. But she also had a well-developed sense of mischief, which everyone knew well. And if the rumours about those parties were true…
They met in the members’ canteen. They bought coffee and croissants and settled down in a side table.
“So, Coco… You have an idea involving Thomasina…”
“I just thought…imagine if Bobby had a female assistant. And somehow, straight away, I thought of Thomasina. I mean, they’re already acquainted…”
“Oh, yes. The Sunday pony rides…”
“Right. And you know how she loves to show off in those latex catsuits… These days hardly see her in anything else. Even though she must be so embarrassed…”
Miss Laidlaw smiled an enigmatic smile. “Yes… Well, I guess you can thank me for that…”
“You, Miss Laidlaw?”
“She pretty much does what I tell her these days. I have a certain amount of, ah, influence, shall we say?”
“Oh. I mean, I did hear some rumours…about the parties, and so on…”
“Did you now? What exactly did you hear? Are you blushing, darling?” She looked amused. “Dear me, I didn’t imagine you were so innocent…”
“I’m not, miss.” She leaned forward. “Is it true? Does she…?”
“Like a professional, darling. But she’s been well-trained.”
“Oh, gosh! It is true then!”
“If you’re a good girl I might show you a video…but not now. It’s a brilliant idea, Coco. I don’t know why I hadn’t thought of it. She’d be perfect! She’s a hopeless submissive… By the way, did you know those cute catsuits are usually equipped with an internal dil-do...or two?”
“I thought so! The way she rides…”
“We should go see Miss Poole together. Today! She’ll love it. She was the one who got Thomasina into latex originally. Imagine… I’ll be able to have her polish my boots anytime I want… Remind her what a slut she is… Show her a video of herself while she’s working!” She laughed out loud. “Oh, and I’ll tell you what!”
“What?”
“She can provide extra services… For the stable lads! That’ll be a new twist. The boot parlour will double its clientele overnight!”
“Miss…! You mean… That’s so gross…”
“It’s ideal! It’s what she does best. Let’s see if Violet’s in now.”
They finished their coffees and made their way to her office.
“Emily! Oh, and Coco. What can I do for you two?”
“I’ll let Coco explain. It was her idea.”
Miss Poole was delighted. “Wonderful! That’s a weight off my mind. The staff will be so happy. And not only the boys. There’s many here who’d love to take her down another peg or two. Having her down on her knees at their behest…”
“It’s her favourite position, Violet…”
“Miss Poole laughed. “Quite so, quite so… And we’ll have to get her a uniform or two… Cynthia will have some ideas… And a title… She could be a boot girl, I suppose…”
“How about boot slut,” suggested Coco, spitefully.
“Oh, perfect. Yes… Book now with our new boot slut, Thomasina Middiford…” She clapped her hands with delight. “And won’t Lady Middiford be proud…”
10
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 05, 2026, 08:04:27 PM »
Another Sitting
Edward’s second portrait sitting took place only two days later. The intervening time flew by at a depressingly rapid rate. Now that he fully understood what these sessions would entail, he felt increasingly antsy as the hours quickly dwindled away. Before he knew it, his mother was picking him up after school on Thursday. An hour later, he was fully dressed again as an adorable little girl. Once more, he stood awkwardly cringing in front of the mirror daintily attired in his darling new pink dress and all his girlish accessories. This time, he was painfully aware that that his summery frock, white tights, black patent Mary Janes, and now his confining corset were merely a gateway to Miss Vale’s studio. His mother had meticulously buttoned his dress, tied his sash, and brushed lint from his flouncy sleeve with a thin smile as the red-faced thirteen-year-old boy felt his boyishness summarily wiped away.
“There,” she said when she was finished, “you look so lovely, dear.” He was sure she was trying to make him feel better, but the adjective seemed to deflate him further.
“Lovely,” he had learned, would include cramped toes, heavy velvet, and an inability to bend properly at the waist for long stretches of time while he was helplessly transformed into a doll-like vision of Victorian girlhood.
“We’d best get downstairs, sweetheart,” his mother said tentatively, “Your Aunt Patricia will be here soon, and we mustn’t keep her waiting.”
Edward exhaled as he tried to steady himself for the onslaught of feminine smothering his aunt would soon lavish on him. Catching another look at himself in the downstairs hall mirror, Edward felt the oddest contradiction: he looked every bit like a carefully dressed little girl, and yet this dress was only a steppingstone to the even more elaborate petticoats, ruffles and lace waiting for him in the studio. His patent Mary Janes caught the light when he shifted his feet, and he wished they were less shiny.
Right on time, Aunt Patricia’s sedan appeared at the curb, moving with the same stately confidence as its owner. She tapped the horn at once, and Edward and his mother stepped out to the driveway. Aunt Patricia opened the driver’s door, and stepped out gaily, “Is our little princess ready for our next sitting?”
Edward felt an inward drop, but he gulped and said meekly, “Yes Aunty.”
The first sitting had been strange enough to seem almost unreal afterward, but the way his aunt was now taking charge of the journey to the studio and all the arrangements this way made his descent into girlhood feel more… complete. Even as she referred to it as “our” sitting, there was little doubt who was steering this ship.
Aunt Patricia beamed condescendingly as she opened the rear door a bit impatiently, and Edward climbed in hesitantly, again smoothing the pink skirt over his knees. His dainty shoes seemed to line themselves up on the floormat as if they too were learning the routine. It bothered him to no end that all these new feminine sensations were causing an excited, trembling stiffness buried in his lacy panties! What was wrong with him?
After the short drive, Aunt Patricia parked near the square. They passed the playground again, and this time it was full. Children and older boys chased a ball across the packed earth, cheeks bright with effort. A pair of girls balanced atop the low wall, arms spread like tightrope walkers. Two boys about Edward’s age were arguing over who should have gotten the ball first, and Edward felt another twist of envy mixed with humiliation. His lip began to quiver as he steeled himself to pass by them.
Unlike him, those boys were spending their afternoon in a totally normal and boisterous way. He was being led like a child to a room where his every curl, button, and breath would soon be assessed, shaped and monitored. He was painfully aware of the bouncy skirt dancing around his knees and the gloss of his dainty shoes below it. If anyone were to recognize him, how could he even begin to explain the whole portrait situation? They would see only a completely sissified Edward Gray, being carefully led down the sidewalk in a darling pink dress by his mother and aunt. He found himself watching the dust rise around the players’ ankles and imagining how ordinary it would feel to come home today with dirt on his shirt instead of blush on his cheeks. Suddenly afraid of being noticed, he blushed and averted his eyes skittishly.
“Keep to the sidewalk, darling,” Aunt Patricia insisted, her hand resting on his shoulder lest he wander too near the gate.
Her hand remained there as they passed, gentle but firm. Edward kept his eyes forward, because looking too long at the playground made him feel as if he were leaving himself behind among the shouts and dust. He felt his cheeks flush and tried to hide behind his aunt. He was actually relieved to get past the playground and through the studio door without drawing more attention.
In the studio, the always mysterious Miss Vale had marked the floor with chalk where the chair stood. “Painters are great friends of memory,” she explained. “But we also appreciate reminders.”
Edward was soon again plunged into the complicated dressing process to become his great-great grandmother’s twin from another time. Once more, he was engulfed in his great-great grandmother's elaborately heavy dress. In no time, Mrs. Bell magically restored his precious ringlets and applied his porcelain doll makeup. Then, Miss Vale recreated the careful hidden architecture of supports and stays beneath his dress. Everything went more efficiently this time. At some point, it began to feel like he had never left the studio at all, and the time in between was just something he had imagined. The delicate wires were slid back up his sleeves, and his knees and legs were again arranged just so. His skirt was lifted and fluffed until the lilac folds fell in the desired bell shape. Then Miss Vale knelt to check his fancily ornate shoes and refasten them to the floor. It seemed to him that his new reality was here on this chair and in this studio.
Soon, Miss Vale began laying in the pale sweep of the dress on her canvas. Edward breathed carefully and tried to ignore the sounds of laughter from the playground that carried through the open window.
During a short break when he was permitted to stretch his legs and move around a bit, he glimpsed the canvas. He saw it was now filling with lilac-gray shadows and soft pearly highlights, but it was not yet obvious what they would become. “It looks like a cloud,” he observed quietly.
“Indeed, but soon we will teach the cloud to behave like velvet,” Miss Vale replied with an enigmatic smile. Then she added, “it looks to me that are inhabiting your role more thoroughly today, dear. You seem to have a more delicate and feminine air.” It was obvious she meant it kindly.
Edward’s heart sank as she confirmed what he had already felt.
His Aunt Patricia, overhearing the exchange, smiled brightly. “You really are becoming more and more an adorably prissy miss, my dear,” she gushed cheerily. “Doesn’t it feel wonderful to honor your family so well?” she asked leadingly.
“Yes, Aunty,” the feminized teen replied flatly after a moment. He cringed as he felt another unexpected jump in his panties.
Edward’s second portrait sitting took place only two days later. The intervening time flew by at a depressingly rapid rate. Now that he fully understood what these sessions would entail, he felt increasingly antsy as the hours quickly dwindled away. Before he knew it, his mother was picking him up after school on Thursday. An hour later, he was fully dressed again as an adorable little girl. Once more, he stood awkwardly cringing in front of the mirror daintily attired in his darling new pink dress and all his girlish accessories. This time, he was painfully aware that that his summery frock, white tights, black patent Mary Janes, and now his confining corset were merely a gateway to Miss Vale’s studio. His mother had meticulously buttoned his dress, tied his sash, and brushed lint from his flouncy sleeve with a thin smile as the red-faced thirteen-year-old boy felt his boyishness summarily wiped away.
“There,” she said when she was finished, “you look so lovely, dear.” He was sure she was trying to make him feel better, but the adjective seemed to deflate him further.
“Lovely,” he had learned, would include cramped toes, heavy velvet, and an inability to bend properly at the waist for long stretches of time while he was helplessly transformed into a doll-like vision of Victorian girlhood.
“We’d best get downstairs, sweetheart,” his mother said tentatively, “Your Aunt Patricia will be here soon, and we mustn’t keep her waiting.”
Edward exhaled as he tried to steady himself for the onslaught of feminine smothering his aunt would soon lavish on him. Catching another look at himself in the downstairs hall mirror, Edward felt the oddest contradiction: he looked every bit like a carefully dressed little girl, and yet this dress was only a steppingstone to the even more elaborate petticoats, ruffles and lace waiting for him in the studio. His patent Mary Janes caught the light when he shifted his feet, and he wished they were less shiny.
Right on time, Aunt Patricia’s sedan appeared at the curb, moving with the same stately confidence as its owner. She tapped the horn at once, and Edward and his mother stepped out to the driveway. Aunt Patricia opened the driver’s door, and stepped out gaily, “Is our little princess ready for our next sitting?”
Edward felt an inward drop, but he gulped and said meekly, “Yes Aunty.”
The first sitting had been strange enough to seem almost unreal afterward, but the way his aunt was now taking charge of the journey to the studio and all the arrangements this way made his descent into girlhood feel more… complete. Even as she referred to it as “our” sitting, there was little doubt who was steering this ship.
Aunt Patricia beamed condescendingly as she opened the rear door a bit impatiently, and Edward climbed in hesitantly, again smoothing the pink skirt over his knees. His dainty shoes seemed to line themselves up on the floormat as if they too were learning the routine. It bothered him to no end that all these new feminine sensations were causing an excited, trembling stiffness buried in his lacy panties! What was wrong with him?
After the short drive, Aunt Patricia parked near the square. They passed the playground again, and this time it was full. Children and older boys chased a ball across the packed earth, cheeks bright with effort. A pair of girls balanced atop the low wall, arms spread like tightrope walkers. Two boys about Edward’s age were arguing over who should have gotten the ball first, and Edward felt another twist of envy mixed with humiliation. His lip began to quiver as he steeled himself to pass by them.
Unlike him, those boys were spending their afternoon in a totally normal and boisterous way. He was being led like a child to a room where his every curl, button, and breath would soon be assessed, shaped and monitored. He was painfully aware of the bouncy skirt dancing around his knees and the gloss of his dainty shoes below it. If anyone were to recognize him, how could he even begin to explain the whole portrait situation? They would see only a completely sissified Edward Gray, being carefully led down the sidewalk in a darling pink dress by his mother and aunt. He found himself watching the dust rise around the players’ ankles and imagining how ordinary it would feel to come home today with dirt on his shirt instead of blush on his cheeks. Suddenly afraid of being noticed, he blushed and averted his eyes skittishly.
“Keep to the sidewalk, darling,” Aunt Patricia insisted, her hand resting on his shoulder lest he wander too near the gate.
Her hand remained there as they passed, gentle but firm. Edward kept his eyes forward, because looking too long at the playground made him feel as if he were leaving himself behind among the shouts and dust. He felt his cheeks flush and tried to hide behind his aunt. He was actually relieved to get past the playground and through the studio door without drawing more attention.
In the studio, the always mysterious Miss Vale had marked the floor with chalk where the chair stood. “Painters are great friends of memory,” she explained. “But we also appreciate reminders.”
Edward was soon again plunged into the complicated dressing process to become his great-great grandmother’s twin from another time. Once more, he was engulfed in his great-great grandmother's elaborately heavy dress. In no time, Mrs. Bell magically restored his precious ringlets and applied his porcelain doll makeup. Then, Miss Vale recreated the careful hidden architecture of supports and stays beneath his dress. Everything went more efficiently this time. At some point, it began to feel like he had never left the studio at all, and the time in between was just something he had imagined. The delicate wires were slid back up his sleeves, and his knees and legs were again arranged just so. His skirt was lifted and fluffed until the lilac folds fell in the desired bell shape. Then Miss Vale knelt to check his fancily ornate shoes and refasten them to the floor. It seemed to him that his new reality was here on this chair and in this studio.
Soon, Miss Vale began laying in the pale sweep of the dress on her canvas. Edward breathed carefully and tried to ignore the sounds of laughter from the playground that carried through the open window.
During a short break when he was permitted to stretch his legs and move around a bit, he glimpsed the canvas. He saw it was now filling with lilac-gray shadows and soft pearly highlights, but it was not yet obvious what they would become. “It looks like a cloud,” he observed quietly.
“Indeed, but soon we will teach the cloud to behave like velvet,” Miss Vale replied with an enigmatic smile. Then she added, “it looks to me that are inhabiting your role more thoroughly today, dear. You seem to have a more delicate and feminine air.” It was obvious she meant it kindly.
Edward’s heart sank as she confirmed what he had already felt.
His Aunt Patricia, overhearing the exchange, smiled brightly. “You really are becoming more and more an adorably prissy miss, my dear,” she gushed cheerily. “Doesn’t it feel wonderful to honor your family so well?” she asked leadingly.
“Yes, Aunty,” the feminized teen replied flatly after a moment. He cringed as he felt another unexpected jump in his panties.
The more you give, the more I can give back.
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