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Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Yesterday at 12:46:20 PM »
Chapter 389.
Once out of the shower, Tim presented himself again in the big living-room, which served as his changing room.
“So… What am I modelling next?”
“You’ll be happy. Another pageboy. But this time more of a fun one.”
“Oh? In what way, miss?”
“Here’s the tunic. This might give you a clue.”
“So what’s the difference? Apart from the fact it’s pink? Oh…” He had noticed the legend on the front and back of the tunic. “Piggy Pageboy? What’s with that, miss?”
“Let’s get it on and I’ll explain.”
“Does it have…a posture trainer?”
“Well, of course. It’s a necessity. But this one’s a little more user-friendly. The user being your mistress, naturally… I’ll show you. On the inside…see?”
Protruding from the seat was what appeared to be a plastic cylinder with a spherical tip, not more than four inches long. But it was sheathed in a translucent pink rubber bulb, presently floppy and deflated. On the outside it manifested itself as a little inflated tail. She helped him on with the shorts and pulled them up.
“What’s great about this is that it pops in so easily.” She suited the action to the word. The plug slipped in effortlessly.
“Now let’s zip you up… buckle the belt…so… Now I’ll show you how easily it is to operate. There’s valves on the air intake for the tail, and the interior bulb. So if I squeeze the tail…so…you can feel the bulb inflating, right?”
“Yes…miss… I can…”
“A few good pumps and it’s nice and firm. Yes?”
“No more, miss… Please…”
“Okay. You see the air is forced along the tube and comes out of those little tiny holes just behind the spherical end. The valve prevents it flowing back, so once it’s inflated, I’m afraid there’s no removing it – unless your know the secret method.” She laughed. “Which you don’t. At the same time the tail is designed to keep its shape. Do not upset your mistress when you’re wearing this, or she may be tempted to give it an extra squeeze! Not comfortable! Of course, the plug itself has all the usual pulse and vibe effects, which I can demonstrate…”
“Not now, please miss!”
“Okay. Maybe later then. Come on. You’re ready. Let’s get you back on the maid-tidy.”
He was soon chained into place again. His audience regarded him with satisfaction.
“I don’t understand. What’s this “piggy” thing?”
“Ah. Frieda… Maybe you’d care to explain…”
“Sure. You see, Tim, when Kit was here we were talking about what a wonderful pet you’d make. ESDS are proposing to advertise some of their boys as pets rather than maids. Some women prefer to have a pet. Pets are lucky. They tend to get spoiled, fed well, played with a lot, and so on. All right, they might have to sleep in a kennel or a basket or be kept in a cage, and they have to wear a locking collar and ring so their mistresses can put them on a leash, but you wouldn’t mind that, would you?”
“So that’s what this collar’s for…?
“Yes. Do you like the idea? I’m sure you must. All your mistress has to do is clip on your lead, and then you have to follow her wherever she goes. She can take you to a party, and everyone will say, “oh, what a pretty piggy! Where did you get him? Can I squeeze his tail?” What fun! Kit thought you’d make a pretty puppy. But I immediately thought of a little piglet. Piglets are cute like you, and they squeak and squeal a lot when they get excited – just like you did earlier – and they can get themselves into such a sticky mess too – just like you also did. And it all ends in tears. So it seems my intuition was correct.”
“Turn round and waggle your tail for us,” said Connie.
Tim did as he was instructed.
“So how do you feel about being a piggy pet?”
The plug felt firm enough inside him for Tim to resolve to be as compliant as possible.
“Yes, it sounds okay…”
“Good boy. I’ll make a note to tell Cassandra she can put you in as a maid, pageboy, or pet, yes?”
“Er, yes, I suppose, miss…”
“Well don’t look so miserable about it – unless you want to be hired out as a houseboy, and be forced to do all the dirty, unpleasant tasks…”
“No, of course not. miss,” he blurted, indignantly. That wouldn’t be fair. I’ve been really good. I’ve done everything you’ve asked of me. I’m a fully-trained pageboy! Houseboy? That the pits! I’m sure Miss Cassandra wouldn’t do such a thing…”
“I beg your pardon?” cried Connie, outraged. “Who do you think you are? Do you think you have any rights here? How dare you express an opinion about what you will or won’t do, or what’s fair or unfair. You need a lesson young man.”
She frowned. “Right. Tomorrow you can be our houseboy for the day, so you understand exactly what it means. Yes, it would be good experience for you. You’ll realise just how tolerant we’ve been, and how lucky you were to be sent here. Houseboys are virtually slaves. They even sleep chained up. They wear chastity devices permanently – no relief. And they’re forbidden to speak, let alone answer back. One word and out comes the ball gag. Oh, you know what? I have one piece of houseboy training equipment right to hand. Want to see it? No? Well you’re going to. Don’t move – oh, you can’t, can you? I’ll be right back.”
Once out of the shower, Tim presented himself again in the big living-room, which served as his changing room.
“So… What am I modelling next?”
“You’ll be happy. Another pageboy. But this time more of a fun one.”
“Oh? In what way, miss?”
“Here’s the tunic. This might give you a clue.”
“So what’s the difference? Apart from the fact it’s pink? Oh…” He had noticed the legend on the front and back of the tunic. “Piggy Pageboy? What’s with that, miss?”
“Let’s get it on and I’ll explain.”
“Does it have…a posture trainer?”
“Well, of course. It’s a necessity. But this one’s a little more user-friendly. The user being your mistress, naturally… I’ll show you. On the inside…see?”
Protruding from the seat was what appeared to be a plastic cylinder with a spherical tip, not more than four inches long. But it was sheathed in a translucent pink rubber bulb, presently floppy and deflated. On the outside it manifested itself as a little inflated tail. She helped him on with the shorts and pulled them up.
“What’s great about this is that it pops in so easily.” She suited the action to the word. The plug slipped in effortlessly.
“Now let’s zip you up… buckle the belt…so… Now I’ll show you how easily it is to operate. There’s valves on the air intake for the tail, and the interior bulb. So if I squeeze the tail…so…you can feel the bulb inflating, right?”
“Yes…miss… I can…”
“A few good pumps and it’s nice and firm. Yes?”
“No more, miss… Please…”
“Okay. You see the air is forced along the tube and comes out of those little tiny holes just behind the spherical end. The valve prevents it flowing back, so once it’s inflated, I’m afraid there’s no removing it – unless your know the secret method.” She laughed. “Which you don’t. At the same time the tail is designed to keep its shape. Do not upset your mistress when you’re wearing this, or she may be tempted to give it an extra squeeze! Not comfortable! Of course, the plug itself has all the usual pulse and vibe effects, which I can demonstrate…”
“Not now, please miss!”
“Okay. Maybe later then. Come on. You’re ready. Let’s get you back on the maid-tidy.”
He was soon chained into place again. His audience regarded him with satisfaction.
“I don’t understand. What’s this “piggy” thing?”
“Ah. Frieda… Maybe you’d care to explain…”
“Sure. You see, Tim, when Kit was here we were talking about what a wonderful pet you’d make. ESDS are proposing to advertise some of their boys as pets rather than maids. Some women prefer to have a pet. Pets are lucky. They tend to get spoiled, fed well, played with a lot, and so on. All right, they might have to sleep in a kennel or a basket or be kept in a cage, and they have to wear a locking collar and ring so their mistresses can put them on a leash, but you wouldn’t mind that, would you?”
“So that’s what this collar’s for…?
“Yes. Do you like the idea? I’m sure you must. All your mistress has to do is clip on your lead, and then you have to follow her wherever she goes. She can take you to a party, and everyone will say, “oh, what a pretty piggy! Where did you get him? Can I squeeze his tail?” What fun! Kit thought you’d make a pretty puppy. But I immediately thought of a little piglet. Piglets are cute like you, and they squeak and squeal a lot when they get excited – just like you did earlier – and they can get themselves into such a sticky mess too – just like you also did. And it all ends in tears. So it seems my intuition was correct.”
“Turn round and waggle your tail for us,” said Connie.
Tim did as he was instructed.
“So how do you feel about being a piggy pet?”
The plug felt firm enough inside him for Tim to resolve to be as compliant as possible.
“Yes, it sounds okay…”
“Good boy. I’ll make a note to tell Cassandra she can put you in as a maid, pageboy, or pet, yes?”
“Er, yes, I suppose, miss…”
“Well don’t look so miserable about it – unless you want to be hired out as a houseboy, and be forced to do all the dirty, unpleasant tasks…”
“No, of course not. miss,” he blurted, indignantly. That wouldn’t be fair. I’ve been really good. I’ve done everything you’ve asked of me. I’m a fully-trained pageboy! Houseboy? That the pits! I’m sure Miss Cassandra wouldn’t do such a thing…”
“I beg your pardon?” cried Connie, outraged. “Who do you think you are? Do you think you have any rights here? How dare you express an opinion about what you will or won’t do, or what’s fair or unfair. You need a lesson young man.”
She frowned. “Right. Tomorrow you can be our houseboy for the day, so you understand exactly what it means. Yes, it would be good experience for you. You’ll realise just how tolerant we’ve been, and how lucky you were to be sent here. Houseboys are virtually slaves. They even sleep chained up. They wear chastity devices permanently – no relief. And they’re forbidden to speak, let alone answer back. One word and out comes the ball gag. Oh, you know what? I have one piece of houseboy training equipment right to hand. Want to see it? No? Well you’re going to. Don’t move – oh, you can’t, can you? I’ll be right back.”
2
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Yesterday at 12:42:08 PM »
Chapter 388.
Connie retreated quietly to her seat, and picked up her glass. Tim dropped all pretence. Staring at the phone, he began to finger the shaft of his erection through the taut latex. The ladies watched, fascinated.
“Interesting technique,” murmured Frieda. He was rolling it back and forth, as if he were kneading a cylinder of plasticine. He slid it about – it must have been lubricating freely for some time - until it was in a comfortable masturbating position, at about forty-five degrees to his zip. He began to massage it with his finger tips, latex squeaking against latex. His breathing was punctuated with little moans of pleasure. The ladies looked at each other and fidgeted in their chairs. Now he was alternating between squeezing it and using a finger against the underside of the glans. His eyes, though half closed, were glued to the phone screen. He began to mumble.
“Kit…I want you so much… My coc-k is so hard, just looking at you…”
At this point Bridget almost choked trying to suppress a fit of giggles. Tim didn’t even notice.
“In a moment…you’ll see…I’m going to do such a big c-um…” He shuddered, and momentarily took his hand off his coc-k… A deep breath…and then he was off again.
“That’s an amazing outfit… What sort of boots are you wearing? I’ll clean them for you every day…twice a day…I’ll do anything you want…please…”
“Ah, now we get to the truth,” whispered Connie. “That is what he really wants. Don’t you think?”
“Yes,” agreed Bridget. “Not only that, but to be her little pet. And from what I’ve seen of Kit, that would really appeal to her…”
And they all sniggered.
“Yes,” grinned Frieda. “I can just see him on a leash…”
Tim was getting perilously near a climax. His fingers worked in a slow cadence, as if he were milking an udder, accompanied by faint juicy ploppings emanating from inside the taut latex. His eyes were half closed now, the hand holding the phone had dropped, and his commentary had subsided into a series of hardly audible groans and squeaks. The right leg band of his shorts slid up and down in time with his movements, and a glistening bead of sticky juice was trickling down his thigh. The ladies were no longer talking, but leaning forward on tenterhooks, waiting for the climax. Tim was right on the edge. He barely dared to touch it now – it was nearly at his hip, like a firm sausage, the latex taut, moulded to its length, twitching of its own accord.
“Go on, Tim,” breathed Bridget, “just let go, silly…”
Let’s give him a hand,” whispered Connie, turning the remote up a couple of notches. That did it. The first sign they had that he had capitulated was when Connie’s phone slipped out of his hand. There was a momentary pause, and then he gasped, shuddered, crossed his thighs, and grabbed the leg frills.
“Oh, gosh! Miss! I’m…ooh….”
The ladies couldn’t suppress their laughter. He was so cute when he came. But he didn’t even notice. His eyes were tight shut. Spasm after spasm ran through him, and c-um streamed down his right leg. Somehow he remained standing. The ladies watched with amusement until the last tremor had died away, and he reopened his eyes. He looked somewhat disoriented. They gave him a little round of applause.
“I-I’m sorry, miss… I didn’t actually mean to…do that…”
“Nonsense, Tim,” said Connie, suppressing her desire to laugh out loud, “that was very impressive. It looked very intense. Was it?”
“Yes… I quite forgot where I was… I was just thinking of…”
“Kit?”
“Y-yes…”
“Well, I think you’ve totally proved yourself.”
“You were amazing,” added Frieda. “You should be proud of yourself.”
Tim smiled faintly. He let go of the slimy leg band and stretched his arms.
“Did I do it well? I really tried. And I didn’t collapse at the end there, though I could have done. Do you think Kit…”
“She’ll be so happy,” said Bridget. “When she sees the video I bet she won’t be able to wait to return.”
They let him preen himself for a few minutes. Connie brought him a drink, put on her rubber gloves – the maid-tidy was a mess - and knelt down to unlock his ankle cuffs.
“We’ll get you cleaned up, then we have time for one more outfit this evening. No more orgasms for you tonight, young man. At least, not before bedtime,” she added, with a wink.
Connie retreated quietly to her seat, and picked up her glass. Tim dropped all pretence. Staring at the phone, he began to finger the shaft of his erection through the taut latex. The ladies watched, fascinated.
“Interesting technique,” murmured Frieda. He was rolling it back and forth, as if he were kneading a cylinder of plasticine. He slid it about – it must have been lubricating freely for some time - until it was in a comfortable masturbating position, at about forty-five degrees to his zip. He began to massage it with his finger tips, latex squeaking against latex. His breathing was punctuated with little moans of pleasure. The ladies looked at each other and fidgeted in their chairs. Now he was alternating between squeezing it and using a finger against the underside of the glans. His eyes, though half closed, were glued to the phone screen. He began to mumble.
“Kit…I want you so much… My coc-k is so hard, just looking at you…”
At this point Bridget almost choked trying to suppress a fit of giggles. Tim didn’t even notice.
“In a moment…you’ll see…I’m going to do such a big c-um…” He shuddered, and momentarily took his hand off his coc-k… A deep breath…and then he was off again.
“That’s an amazing outfit… What sort of boots are you wearing? I’ll clean them for you every day…twice a day…I’ll do anything you want…please…”
“Ah, now we get to the truth,” whispered Connie. “That is what he really wants. Don’t you think?”
“Yes,” agreed Bridget. “Not only that, but to be her little pet. And from what I’ve seen of Kit, that would really appeal to her…”
And they all sniggered.
“Yes,” grinned Frieda. “I can just see him on a leash…”
Tim was getting perilously near a climax. His fingers worked in a slow cadence, as if he were milking an udder, accompanied by faint juicy ploppings emanating from inside the taut latex. His eyes were half closed now, the hand holding the phone had dropped, and his commentary had subsided into a series of hardly audible groans and squeaks. The right leg band of his shorts slid up and down in time with his movements, and a glistening bead of sticky juice was trickling down his thigh. The ladies were no longer talking, but leaning forward on tenterhooks, waiting for the climax. Tim was right on the edge. He barely dared to touch it now – it was nearly at his hip, like a firm sausage, the latex taut, moulded to its length, twitching of its own accord.
“Go on, Tim,” breathed Bridget, “just let go, silly…”
Let’s give him a hand,” whispered Connie, turning the remote up a couple of notches. That did it. The first sign they had that he had capitulated was when Connie’s phone slipped out of his hand. There was a momentary pause, and then he gasped, shuddered, crossed his thighs, and grabbed the leg frills.
“Oh, gosh! Miss! I’m…ooh….”
The ladies couldn’t suppress their laughter. He was so cute when he came. But he didn’t even notice. His eyes were tight shut. Spasm after spasm ran through him, and c-um streamed down his right leg. Somehow he remained standing. The ladies watched with amusement until the last tremor had died away, and he reopened his eyes. He looked somewhat disoriented. They gave him a little round of applause.
“I-I’m sorry, miss… I didn’t actually mean to…do that…”
“Nonsense, Tim,” said Connie, suppressing her desire to laugh out loud, “that was very impressive. It looked very intense. Was it?”
“Yes… I quite forgot where I was… I was just thinking of…”
“Kit?”
“Y-yes…”
“Well, I think you’ve totally proved yourself.”
“You were amazing,” added Frieda. “You should be proud of yourself.”
Tim smiled faintly. He let go of the slimy leg band and stretched his arms.
“Did I do it well? I really tried. And I didn’t collapse at the end there, though I could have done. Do you think Kit…”
“She’ll be so happy,” said Bridget. “When she sees the video I bet she won’t be able to wait to return.”
They let him preen himself for a few minutes. Connie brought him a drink, put on her rubber gloves – the maid-tidy was a mess - and knelt down to unlock his ankle cuffs.
“We’ll get you cleaned up, then we have time for one more outfit this evening. No more orgasms for you tonight, young man. At least, not before bedtime,” she added, with a wink.
3
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Yesterday at 12:36:54 PM »
Chapter 387.
Not only had Miss Poole been the instigator of Thomasina’s latex outfits, but she had also been instrumental in engineering her mother’s acceptance of them. Lady Middiford had been ambiguous about that first shocking pink catsuit, but by the time Thomasina had graduated to the more provocative cream one, created for Emily Laidlaw’s party by Cynthia, Violet had convinced her that her daughter was merely dressing cool and fashionable, and exploiting her natural beauty. Since then she had taken a motherly interest in her clothes, and frequently took her to Fantastex to review the new lines. And believing that her daughter was dressing in the height of fashion, and all the attention she accrued was born merely of admiration, insisted she travel to and from Pitt’s Wood in her work clothes. And much as Thomasina found stimulation in the scrutiny of others, nevertheless she was eager to find a reliable form of private transport, a little car, or even a motorbike…
Tim had been wondering how Bobby was coping without him. He would have been relieved to know that help was on the way. But at present he had other things on his mind, specifically the photograph on the screen of Connie’s phone. He swallowed.
“Well?”
“W-well?”
“What do you think?”
“Oh…ah, well… She, er, has very good, er, dress sense…”
Connie and the others burst out laughing.
“Shall I tell her that?” asked Connie. “Tim thinks you have very good dress sense? I can text her now…”
“No! No, miss, don’t do that…”
He was trembling slightly as he stared at her phone, and he was blinking nervously. He was still holding his right arm protectively over the right side of his shorts, his fingers gripping the leg frills.
“She sent you a message, too…”
“Sh-she did…?”
“Yes. Would you like to read it?”
“Y-yes please, miss…”
Connie scrolled down. “Here, take the phone.” She pushed it into his free hand. He looked, wide-eyed.
“Hi to Tim! Do you like my party wear? This pic is for you no one els. I want you use it til we meet again. If it make you c-um it mean we shood have sex. Miss Connie will tell me. I hope I see video. xxx”
Tim could hardly believe what he was reading.
“Th-this is really from…Kit?”
“Of course. You know she seriously fancies you, don’t you?”
“So she’s saying…”
“She’s wants you to use her picture until she gets to see you again. To masturbate, silly! She wants you to show her how much you’re missing her.”
Tim stared at her. “She does?”
Connie nodded. It was true. Kit had told her. She had never had sex with a man. She loved her girlfriend. All the men she had met had been too pushy, too dominating, too eager to “invade my body” as she had put it. Her technique was to let them think she was up for it, then abandon them, leaving them no satisfaction except that they could supply themselves. But for her Tim was the sole exception, the polar opposite of all those predators. And it was obvious to her he was a sexy guy. And she wanted a demonstration of his feelings for her.
He stood there staring at the phone in his hand. He looked almost scared of it.
“Well you could wait for the poster, I suppose, but that wouldn’t be very gallant, now would it?”
“Shall I…?”
“Do it, Tim!” cried Frieda.
“Go on! Show Kit how you feel about her!” added Bridget.
He glanced at them, but his gaze quickly returned to the phone. Connie knew they had him. He was technically an adult, but in terms of his sexual predilections he was still a young teenager, for whom a photo of a beautiful woman, especially the very woman he was fixated on, was the perfect substitute for the real thing.
“Okay… I shall…”
Not only had Miss Poole been the instigator of Thomasina’s latex outfits, but she had also been instrumental in engineering her mother’s acceptance of them. Lady Middiford had been ambiguous about that first shocking pink catsuit, but by the time Thomasina had graduated to the more provocative cream one, created for Emily Laidlaw’s party by Cynthia, Violet had convinced her that her daughter was merely dressing cool and fashionable, and exploiting her natural beauty. Since then she had taken a motherly interest in her clothes, and frequently took her to Fantastex to review the new lines. And believing that her daughter was dressing in the height of fashion, and all the attention she accrued was born merely of admiration, insisted she travel to and from Pitt’s Wood in her work clothes. And much as Thomasina found stimulation in the scrutiny of others, nevertheless she was eager to find a reliable form of private transport, a little car, or even a motorbike…
Tim had been wondering how Bobby was coping without him. He would have been relieved to know that help was on the way. But at present he had other things on his mind, specifically the photograph on the screen of Connie’s phone. He swallowed.
“Well?”
“W-well?”
“What do you think?”
“Oh…ah, well… She, er, has very good, er, dress sense…”
Connie and the others burst out laughing.
“Shall I tell her that?” asked Connie. “Tim thinks you have very good dress sense? I can text her now…”
“No! No, miss, don’t do that…”
He was trembling slightly as he stared at her phone, and he was blinking nervously. He was still holding his right arm protectively over the right side of his shorts, his fingers gripping the leg frills.
“She sent you a message, too…”
“Sh-she did…?”
“Yes. Would you like to read it?”
“Y-yes please, miss…”
Connie scrolled down. “Here, take the phone.” She pushed it into his free hand. He looked, wide-eyed.
“Hi to Tim! Do you like my party wear? This pic is for you no one els. I want you use it til we meet again. If it make you c-um it mean we shood have sex. Miss Connie will tell me. I hope I see video. xxx”
Tim could hardly believe what he was reading.
“Th-this is really from…Kit?”
“Of course. You know she seriously fancies you, don’t you?”
“So she’s saying…”
“She’s wants you to use her picture until she gets to see you again. To masturbate, silly! She wants you to show her how much you’re missing her.”
Tim stared at her. “She does?”
Connie nodded. It was true. Kit had told her. She had never had sex with a man. She loved her girlfriend. All the men she had met had been too pushy, too dominating, too eager to “invade my body” as she had put it. Her technique was to let them think she was up for it, then abandon them, leaving them no satisfaction except that they could supply themselves. But for her Tim was the sole exception, the polar opposite of all those predators. And it was obvious to her he was a sexy guy. And she wanted a demonstration of his feelings for her.
He stood there staring at the phone in his hand. He looked almost scared of it.
“Well you could wait for the poster, I suppose, but that wouldn’t be very gallant, now would it?”
“Shall I…?”
“Do it, Tim!” cried Frieda.
“Go on! Show Kit how you feel about her!” added Bridget.
He glanced at them, but his gaze quickly returned to the phone. Connie knew they had him. He was technically an adult, but in terms of his sexual predilections he was still a young teenager, for whom a photo of a beautiful woman, especially the very woman he was fixated on, was the perfect substitute for the real thing.
“Okay… I shall…”
4
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on August 10, 2026, 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.
5
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 10, 2026, 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…”
6
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 10, 2026, 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.”
7
Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by bonzodoug on August 10, 2026, 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?
8
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
9
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.”
10
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 :)
The more you give, the more I can give back.
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