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Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 11, 2025, 08:31:28 AM »
Chapter 271.
Tim slept surprisingly well considering the unusual surroundings, and woke early, roused by the discomfort of a thwarted erection. He slipped out of bed, discarded his nightdress, and headed for the shower, which he took cool. Feeling slightly more relaxed, he wrapped himself in a towel and returned to the bedroom. He sat on the bed, speculating on what sort of dress he might be asked to wear today, not without a frisson of anticipation.
There was a gentle tap at the door.
“Come in…”
“Good morning. It’s Tim, isn’t it?”
The speaker was a slim shortish young woman of about twenty, with blue eyes, cropped hair dyed black, black eyeliner, and nose, lip and ear piercings, dressed in a black T-shirt, a short black leather jacket, a black leather miniskirt, black tights and ankle boots. She had a pink Fantastex carrier bag in her hand.
“Er…yes…”
“Hi. I’m Priscilla. I’ve brought your clothes. Would you like a coffee?”
Tim smiled. “Priscilla” seemed the most unlikely name for her. But she was pretty, and despite the outfit, had a soft and reassuring manner.
“Oh, er…nice to meet you… No, that’s all right. I’ll get dressed and come to the kitchen.”
“Okay, Tim. Serena told me to help you dress, if that’s okay.”
“Er…”
“You may need help zipping up. Why don’t you pop into the loo and put on your bloomers, and I’ll take it from there.”
“Bloomers?”
“Oh, don’t worry. They’re pretty. Look.”
She approached the bed, put the carrier bag on it, rummaged inside, and produced a pair of pink latex elasticated bloomers, like a magician producing a rabbit from a hat.
“Taraa! Cute, eh? Here, take them. Off you go. Let’s get you ready before Nicola and Terry get here. Terry’s really looking forward to meeting you…”
As Tim slipped into his new bloomers, he was feeling slightly unnerved. What could possibly go with these? Something other than a pretty satin dress, he thought. Unless they were just to contain his secretions… Of course they fitted perfectly. Cynthia knew her stuff…
Returning to the bedroom, he found Priscilla, with a mischievous expression on her face, holding something behind the carrier bag. With a sudden flourish, she held it up. A glossy pink latex dress, with a round collar, puff sleeves, and a short flared skirt.
“Do you like it?”
“Oh, er…yeah, I guess…”
“Your our maid today, see?”
“Your…maid?”
“Yes! Isn’t that exciting? Come on, let’s get you dressed. Stockings first, young man. Sit on the bed and I’ll put them on for you.”
Tim had no choice but to comply. The white stockings came right to the tops of his thighs. Priscilla chatted away as she tugged and smoothed them into place.
“That Cynthia. So clever! Cassandra specified pink, and gave her a general description.”
Cassandra! So Serena’s mother was behind this!
“So you know what she did? She made three outfits – each one slightly different. You’ll need a couple of changes anyway. So you’re all set up.”
Set up? For what, wondered Tim. But for the time being he held his peace.
Priscilla made him stand up. She produced a little tube of what she called “sock glue”, and proceeded to glue the tops to his thighs.
“Clever, eh? This way they stay put, whatever.”
Next on went his little padded bra, then the dress. As she zipped up the back Tim felt it clasp the contours of his body. Made to measure. Then she went behind him, tied on a little white latex apron, fastened a white satin choker, and stood back to admire him.
“Look at yourself in the mirror. Oh my god, you’re so cute…”
Tim wasn’t so sure. This was one outfit he’d prefer not to show off.
“The headpiece and matching gloves are on order, but you won’t need them today. Here are your shoes, classic maid footwear…”
She pushed him back onto the bed, knelt, and fitted him with a pair of black lace-ups with low heels.
“Now sit down at the dressing-table and I’ll do your makeup and put on your earrings. O my god, this is so fun!”
When she was satisfied, she took Tim by the hand and led him back to the living-room. It was empty, but voices could be heard in the kitchen. She led him in. There was Serena with two other young women. All three gasped with delight when they saw him.
“Wow, Tim! You look amazing!” cried Serena. “Do you like it?”
“I guess… But why…?”
“Why a maid? A latex maid?” She giggled. “Because, dear Tim, today is the first day of your maid’s training!”
Tim looked aghast. “T-training…?”
“Yes! I promised to tell you, didn’t I? You’re going to be a full-trained ladies’ maid. True! Let me explain. Oh, first, these are two of my best friends. This” (she indicated an auburn-haired woman, contemplating Tim with a shrewd smile) “is Margaret, and this” (a slight woman in a little black dress) “is Nicola.”
The women nodded, Tim stammered a greeting.
Serena turned to Nicola.
“Where is Terry? Will he be long?”
“No. He’s upstairs getting ready. He’s dying to meet Tim.”
“Okay, good. Now Tim,” went on Serena, “why don’t you stand over there by the window in the light where we can see you better. Then I’ll explain.
“Okay…”
“Tim… You’re a maid now. “Yes miss” is what you say, not “okay”…”
Tim blushed. “Yes, miss…” He moved to the window and faced his audience, Margaret and Nicola both smirking at his discomfort. He too was eager to meet Terry, hoping he might be an ally…
Tim slept surprisingly well considering the unusual surroundings, and woke early, roused by the discomfort of a thwarted erection. He slipped out of bed, discarded his nightdress, and headed for the shower, which he took cool. Feeling slightly more relaxed, he wrapped himself in a towel and returned to the bedroom. He sat on the bed, speculating on what sort of dress he might be asked to wear today, not without a frisson of anticipation.
There was a gentle tap at the door.
“Come in…”
“Good morning. It’s Tim, isn’t it?”
The speaker was a slim shortish young woman of about twenty, with blue eyes, cropped hair dyed black, black eyeliner, and nose, lip and ear piercings, dressed in a black T-shirt, a short black leather jacket, a black leather miniskirt, black tights and ankle boots. She had a pink Fantastex carrier bag in her hand.
“Er…yes…”
“Hi. I’m Priscilla. I’ve brought your clothes. Would you like a coffee?”
Tim smiled. “Priscilla” seemed the most unlikely name for her. But she was pretty, and despite the outfit, had a soft and reassuring manner.
“Oh, er…nice to meet you… No, that’s all right. I’ll get dressed and come to the kitchen.”
“Okay, Tim. Serena told me to help you dress, if that’s okay.”
“Er…”
“You may need help zipping up. Why don’t you pop into the loo and put on your bloomers, and I’ll take it from there.”
“Bloomers?”
“Oh, don’t worry. They’re pretty. Look.”
She approached the bed, put the carrier bag on it, rummaged inside, and produced a pair of pink latex elasticated bloomers, like a magician producing a rabbit from a hat.
“Taraa! Cute, eh? Here, take them. Off you go. Let’s get you ready before Nicola and Terry get here. Terry’s really looking forward to meeting you…”
As Tim slipped into his new bloomers, he was feeling slightly unnerved. What could possibly go with these? Something other than a pretty satin dress, he thought. Unless they were just to contain his secretions… Of course they fitted perfectly. Cynthia knew her stuff…
Returning to the bedroom, he found Priscilla, with a mischievous expression on her face, holding something behind the carrier bag. With a sudden flourish, she held it up. A glossy pink latex dress, with a round collar, puff sleeves, and a short flared skirt.
“Do you like it?”
“Oh, er…yeah, I guess…”
“Your our maid today, see?”
“Your…maid?”
“Yes! Isn’t that exciting? Come on, let’s get you dressed. Stockings first, young man. Sit on the bed and I’ll put them on for you.”
Tim had no choice but to comply. The white stockings came right to the tops of his thighs. Priscilla chatted away as she tugged and smoothed them into place.
“That Cynthia. So clever! Cassandra specified pink, and gave her a general description.”
Cassandra! So Serena’s mother was behind this!
“So you know what she did? She made three outfits – each one slightly different. You’ll need a couple of changes anyway. So you’re all set up.”
Set up? For what, wondered Tim. But for the time being he held his peace.
Priscilla made him stand up. She produced a little tube of what she called “sock glue”, and proceeded to glue the tops to his thighs.
“Clever, eh? This way they stay put, whatever.”
Next on went his little padded bra, then the dress. As she zipped up the back Tim felt it clasp the contours of his body. Made to measure. Then she went behind him, tied on a little white latex apron, fastened a white satin choker, and stood back to admire him.
“Look at yourself in the mirror. Oh my god, you’re so cute…”
Tim wasn’t so sure. This was one outfit he’d prefer not to show off.
“The headpiece and matching gloves are on order, but you won’t need them today. Here are your shoes, classic maid footwear…”
She pushed him back onto the bed, knelt, and fitted him with a pair of black lace-ups with low heels.
“Now sit down at the dressing-table and I’ll do your makeup and put on your earrings. O my god, this is so fun!”
When she was satisfied, she took Tim by the hand and led him back to the living-room. It was empty, but voices could be heard in the kitchen. She led him in. There was Serena with two other young women. All three gasped with delight when they saw him.
“Wow, Tim! You look amazing!” cried Serena. “Do you like it?”
“I guess… But why…?”
“Why a maid? A latex maid?” She giggled. “Because, dear Tim, today is the first day of your maid’s training!”
Tim looked aghast. “T-training…?”
“Yes! I promised to tell you, didn’t I? You’re going to be a full-trained ladies’ maid. True! Let me explain. Oh, first, these are two of my best friends. This” (she indicated an auburn-haired woman, contemplating Tim with a shrewd smile) “is Margaret, and this” (a slight woman in a little black dress) “is Nicola.”
The women nodded, Tim stammered a greeting.
Serena turned to Nicola.
“Where is Terry? Will he be long?”
“No. He’s upstairs getting ready. He’s dying to meet Tim.”
“Okay, good. Now Tim,” went on Serena, “why don’t you stand over there by the window in the light where we can see you better. Then I’ll explain.
“Okay…”
“Tim… You’re a maid now. “Yes miss” is what you say, not “okay”…”
Tim blushed. “Yes, miss…” He moved to the window and faced his audience, Margaret and Nicola both smirking at his discomfort. He too was eager to meet Terry, hoping he might be an ally…
22
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 11, 2025, 08:24:51 AM »
Chapter 270.
As Bobby walked or trotted along the sandy track, listening to the singing of the birds and the occasional crack of a twig echoing in the trees, his mood lightened. He was enjoying being a pony again, an anonymous animal, and the reassuring feeling of Mélisande on his back. For a while he’d be free of responsibility, totally dependent on and obedient to her wishes. He snorted with pleasure. And when they emerged from the forest into open countryside, and he saw in the distance two riders heading their way, he no longer felt nervous, but eager to impress them with his glossy grey coat and his spirited demeanour.
Slowly they closed on each other. Two girls on horseback. He could see them staring and pointing from some way away. As they got nearer they waved and called “good morning!” They came up and stopped.
“Is that…Ponyboy?” gasped one. “The pony from the show?”
“That’s right,” said Mélisande.
“And it was you who rode him, right?” said the other.
“Yes. He’s my pony. I trained him up from just being a boy. For a long time I kept him in my stable at home, but now he stays at Pitt’s Wood.”
“Can we pat him?”
“Go ahead.”
They jumped down and started making a fuss of Bobby, patting and stroking him, feeling his mane and ears.
“He’s gorgeous! You’re so lucky…”
Bobby found himself enjoying the attention. He even nodded his head like a pony to indicate pleasure! It only occurred to him later on that day that there may have been something ludicrous about that sort of behaviour. But even then his doubts were quickly swept aside by the sheer delight, physical and psychological, he felt in being for a while someone’s cherished pony, belonging to her wholly, under her sole control. That day marked his acknowledgement of a guiltless addiction that would last many years…
About eleven Mélisande stopped for lunch. She was supposed to have him back by half past twelve, so that he could have a break before the pony rides, so she couldn’t turn back too late. She spotted a sunny pasture surrounded by hedgerows, swung herself out of the saddle, and led Bobby to a fallen tree. Tethering him to a root, she took off her rucksack and seated herself. She took off his bit and shared out the lunch her mother had packed for them, feeding him by hand, holding the drink carton while he suc-ked up the juice, and wiping his mouth. After lunch she discreetly unzipped and refastened his pouch so he could relieve himself. Then she began to unbuckle his bridle.
“What are you doing?”
“I’m changing your mask, Bobby. You should have a new one for the afternoon.”
“Why?”
She held up the blank mask, and showed him the inside..
“No, please not that one…”
She smiled. “Yes, Bobby, this one.”
“Why, Mellie?”
“I want you to learn to trust me unconditionally.” She smiled, and whispered. “and I rather like the idea of you being plugged both ends…”
“That’s not fair! How do you know that… Anyway, I won’t wear it…”
She sighed. “I know everything now. No need to be shy.” She took out the pump and held it in front of his nose. The threat was enough.
“No…you wouldn’t!”
She sighed and stood up.
“Okay, okay… Whatever you say.”
“That’s better.”
She took off his bridle, pony hood and mask, and slipped on the new one. He resisted the plug for a moment, but she held his nose till he capitulated. Then she refitted the pony hood, and before putting on the bridle, she attached the special retaining strap, consisting on a broad leather mouth-cover, wider under the nose and tapering at the sides where it was attached to the side-rings. She re-threaded the neck strap and buckled it tightly and the back of his neck. Now the gag was held immovably in his mouth. Then she replaced the bridle, firmly attaching all the straps to the side-rings. A quick fluff up of his mane and a tug on the ears and he was ready to go.
She mounted and guided him back onto the track.
“Don’t hesitate. Keep the pace going. I’ll look after you.”
She guided him with hands, heels, gentle taps of her whip, and occasional spoken commands.
“Puddle ahead. Careful not to slip.”
“Tree branch on left. Just brush through it.”
As he grew used to responding only to his rider’s instructions his confidence grew, and after half an hour he was trotting at full speed, weaving in and out of obstacles in response to the aids. Mélisande smiled. Over the coming weeks she would aim to establish absolute trust, and thus to build total obedience, from which she hoped would flow unqualified loyalty. She was confident that in the end her power over him would be unmatched by any rival, and that ultimately he would be hers alone…
After about fifteen minutes he heard the sound of water, and Mélisande leant forward.
“We’re going to cross a little stream. It’s stony, so pick up your hooves.”
He splashed through the water and climbed up a gentle, springy bank. They had never come this far before, and he knew they were now in unknown territory. A little further and he could tell from the echoes and the smell of pine that they had entered another forest. In the distance he could hear the sound of a circular saw. But that soon faded, and then he was on a winding stony path. After a few more minutes, Mélisande guided him onto a patch of grass and dismounted.
“Wait here.”
He stood there in the silence. Five minutes passed. Ten. He began to get anxious. Was she going to abandon him? Of course not. Why would she do that? Fifteen… He began to swivel around, listening for the slightest sound. Then he started making muffled interrogatory noises. Still no response. Then, after about twenty minutes, he started to panic. He couldn’t hear anything, he could see nothing, he was apparently alone in a strange place, helpless in his pony gear, plugged both ends, tightly strapped and bridled up. Suppose some kids found him. They could do whatever they liked, and he would be powerless to resist. Suppose…
He started trotting backwards and forwards, until he bumped straight into a tree stump, and fell on his side. He lay there kicking wildly, unable to get to his hooves, rotating slowly as his struggles increased. Then all of a sudden he heard a snort nearby, and froze. Mélisande, who had been sitting on a log watching the whole performance, had finally been unable to contain her mirth any longer. She quickly assumed a serious tone.
“Bobby! Found you at last! Thank goodness! We were lost, so I just went to see if I could find any landmarks, and then I couldn’t find my way back. But here you are, my gorgeous little ponyboy,” she added, hauling him back onto his feet. “Oh, you’re trembling… I hope you weren’t frightened….”
Bobby grunted and shook his head vigorously. Mélisande mounted up, biting her lip to prevent bursting out laughing. Reluctantly she turned him back the way they had come. It was twelve. They were going to be late. Well, so what? She gave him a kick and two good firm smacks with her whip to urge him on, and they retraced their route..
When they arrived back at Pitt’s Wood, Bobby tired and aching, she did think of changing his mask back. But then she thought, “why should I? He’s mine, isn’t he? I’m old enough now that I can do as I like with him.” So she rode him back to the stable, past all the inquisitive faces, and tethered him outside while she texted Ellie to say they were back.
After ten minutes or so, after everyone had had a chance to come and goggle at him and pat him and take photos of the smooth blank latex moulded to his features, Ellie and Clarissa, who had been drinking tea in the canteen, arrived at the little knot of girls surrounding him. Clarissa stared.
“Mélisande! You’re late! Where have you been? Wait… Have you…changed his mask?”
“Yes, mummy. I was training him to obey the aids and nothing else.”
“But isn’t that one… I mean, it doesn’t have a, er, thing…does it?”
“Yes, mummy, it does. And he loves it!”
Ellie covered her mouth and sniggered.
“Darling, you can’t just, you know, do whatever you want…”
“Why not, mummy? You do…”
“I…?”
“Yes. Once I came to the loose box early, and I saw you…”
Clarissa turned white. “Mélisande! Not another word! I’ll deal with this later. Let’s get him inside, Ellie, and get him out of this. Mellie, please stay here, or…here – take this and go buy yourself something in the canteen. And stay there please, till I come and collect you.”
“Yes mummy. Thank you mummy.”
As Bobby walked or trotted along the sandy track, listening to the singing of the birds and the occasional crack of a twig echoing in the trees, his mood lightened. He was enjoying being a pony again, an anonymous animal, and the reassuring feeling of Mélisande on his back. For a while he’d be free of responsibility, totally dependent on and obedient to her wishes. He snorted with pleasure. And when they emerged from the forest into open countryside, and he saw in the distance two riders heading their way, he no longer felt nervous, but eager to impress them with his glossy grey coat and his spirited demeanour.
Slowly they closed on each other. Two girls on horseback. He could see them staring and pointing from some way away. As they got nearer they waved and called “good morning!” They came up and stopped.
“Is that…Ponyboy?” gasped one. “The pony from the show?”
“That’s right,” said Mélisande.
“And it was you who rode him, right?” said the other.
“Yes. He’s my pony. I trained him up from just being a boy. For a long time I kept him in my stable at home, but now he stays at Pitt’s Wood.”
“Can we pat him?”
“Go ahead.”
They jumped down and started making a fuss of Bobby, patting and stroking him, feeling his mane and ears.
“He’s gorgeous! You’re so lucky…”
Bobby found himself enjoying the attention. He even nodded his head like a pony to indicate pleasure! It only occurred to him later on that day that there may have been something ludicrous about that sort of behaviour. But even then his doubts were quickly swept aside by the sheer delight, physical and psychological, he felt in being for a while someone’s cherished pony, belonging to her wholly, under her sole control. That day marked his acknowledgement of a guiltless addiction that would last many years…
About eleven Mélisande stopped for lunch. She was supposed to have him back by half past twelve, so that he could have a break before the pony rides, so she couldn’t turn back too late. She spotted a sunny pasture surrounded by hedgerows, swung herself out of the saddle, and led Bobby to a fallen tree. Tethering him to a root, she took off her rucksack and seated herself. She took off his bit and shared out the lunch her mother had packed for them, feeding him by hand, holding the drink carton while he suc-ked up the juice, and wiping his mouth. After lunch she discreetly unzipped and refastened his pouch so he could relieve himself. Then she began to unbuckle his bridle.
“What are you doing?”
“I’m changing your mask, Bobby. You should have a new one for the afternoon.”
“Why?”
She held up the blank mask, and showed him the inside..
“No, please not that one…”
She smiled. “Yes, Bobby, this one.”
“Why, Mellie?”
“I want you to learn to trust me unconditionally.” She smiled, and whispered. “and I rather like the idea of you being plugged both ends…”
“That’s not fair! How do you know that… Anyway, I won’t wear it…”
She sighed. “I know everything now. No need to be shy.” She took out the pump and held it in front of his nose. The threat was enough.
“No…you wouldn’t!”
She sighed and stood up.
“Okay, okay… Whatever you say.”
“That’s better.”
She took off his bridle, pony hood and mask, and slipped on the new one. He resisted the plug for a moment, but she held his nose till he capitulated. Then she refitted the pony hood, and before putting on the bridle, she attached the special retaining strap, consisting on a broad leather mouth-cover, wider under the nose and tapering at the sides where it was attached to the side-rings. She re-threaded the neck strap and buckled it tightly and the back of his neck. Now the gag was held immovably in his mouth. Then she replaced the bridle, firmly attaching all the straps to the side-rings. A quick fluff up of his mane and a tug on the ears and he was ready to go.
She mounted and guided him back onto the track.
“Don’t hesitate. Keep the pace going. I’ll look after you.”
She guided him with hands, heels, gentle taps of her whip, and occasional spoken commands.
“Puddle ahead. Careful not to slip.”
“Tree branch on left. Just brush through it.”
As he grew used to responding only to his rider’s instructions his confidence grew, and after half an hour he was trotting at full speed, weaving in and out of obstacles in response to the aids. Mélisande smiled. Over the coming weeks she would aim to establish absolute trust, and thus to build total obedience, from which she hoped would flow unqualified loyalty. She was confident that in the end her power over him would be unmatched by any rival, and that ultimately he would be hers alone…
After about fifteen minutes he heard the sound of water, and Mélisande leant forward.
“We’re going to cross a little stream. It’s stony, so pick up your hooves.”
He splashed through the water and climbed up a gentle, springy bank. They had never come this far before, and he knew they were now in unknown territory. A little further and he could tell from the echoes and the smell of pine that they had entered another forest. In the distance he could hear the sound of a circular saw. But that soon faded, and then he was on a winding stony path. After a few more minutes, Mélisande guided him onto a patch of grass and dismounted.
“Wait here.”
He stood there in the silence. Five minutes passed. Ten. He began to get anxious. Was she going to abandon him? Of course not. Why would she do that? Fifteen… He began to swivel around, listening for the slightest sound. Then he started making muffled interrogatory noises. Still no response. Then, after about twenty minutes, he started to panic. He couldn’t hear anything, he could see nothing, he was apparently alone in a strange place, helpless in his pony gear, plugged both ends, tightly strapped and bridled up. Suppose some kids found him. They could do whatever they liked, and he would be powerless to resist. Suppose…
He started trotting backwards and forwards, until he bumped straight into a tree stump, and fell on his side. He lay there kicking wildly, unable to get to his hooves, rotating slowly as his struggles increased. Then all of a sudden he heard a snort nearby, and froze. Mélisande, who had been sitting on a log watching the whole performance, had finally been unable to contain her mirth any longer. She quickly assumed a serious tone.
“Bobby! Found you at last! Thank goodness! We were lost, so I just went to see if I could find any landmarks, and then I couldn’t find my way back. But here you are, my gorgeous little ponyboy,” she added, hauling him back onto his feet. “Oh, you’re trembling… I hope you weren’t frightened….”
Bobby grunted and shook his head vigorously. Mélisande mounted up, biting her lip to prevent bursting out laughing. Reluctantly she turned him back the way they had come. It was twelve. They were going to be late. Well, so what? She gave him a kick and two good firm smacks with her whip to urge him on, and they retraced their route..
When they arrived back at Pitt’s Wood, Bobby tired and aching, she did think of changing his mask back. But then she thought, “why should I? He’s mine, isn’t he? I’m old enough now that I can do as I like with him.” So she rode him back to the stable, past all the inquisitive faces, and tethered him outside while she texted Ellie to say they were back.
After ten minutes or so, after everyone had had a chance to come and goggle at him and pat him and take photos of the smooth blank latex moulded to his features, Ellie and Clarissa, who had been drinking tea in the canteen, arrived at the little knot of girls surrounding him. Clarissa stared.
“Mélisande! You’re late! Where have you been? Wait… Have you…changed his mask?”
“Yes, mummy. I was training him to obey the aids and nothing else.”
“But isn’t that one… I mean, it doesn’t have a, er, thing…does it?”
“Yes, mummy, it does. And he loves it!”
Ellie covered her mouth and sniggered.
“Darling, you can’t just, you know, do whatever you want…”
“Why not, mummy? You do…”
“I…?”
“Yes. Once I came to the loose box early, and I saw you…”
Clarissa turned white. “Mélisande! Not another word! I’ll deal with this later. Let’s get him inside, Ellie, and get him out of this. Mellie, please stay here, or…here – take this and go buy yourself something in the canteen. And stay there please, till I come and collect you.”
“Yes mummy. Thank you mummy.”
23
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 11, 2025, 08:13:12 AM »
Chapter 269.
While Ellie and Clarissa got him into his suit behind the closed door of stable thirteen, Mélisande stood outside. She tossed her whip onto the ground whilst she strapped on her helmet and pulled on her leather gloves. She reminisced about her first ride on Bobby, at the top of that very field. She smiled. What a sulky little brat she’d been then! At first she had even refused to mount him! Thank goodness she’d had a change of heart - though it was only out of vanity, to show off her riding skills in front of an audience. But it’d been so much fun riding a boy-pony instead of a real pony she’d been hooked from that moment.
After ten minutes or so, the door opened and Clarissa stuck her head out.
“Darling? He’s virtually ready. Would you like to put on his hoods and tack him up?”
She went inside. There he was, transformed into a little grey pony, just how she liked him. She began with the moulded whole-head cream latex hood – the one Clarissa had packed. It slipped on quite easily. It had a neckpiece that helped to keep it firmly in position. She adjusted the fit so all the holes were in the right places and the nostril flanges were holding the nostrils open. Then the pony hood itself, with its little mane and furry ears. Then the bridle with its head-straps, which she attached to the side-rings of the rubber bit. Then the neck strap, a single strap threaded through both rings and buckled at the back of the neck, which she tightened so as to pull the bit firmly into Bobby’s mouth. Finally she clipped the reins to the rings. Then it only remained to put the saddle in place, tighten the girths, and let down the stirrups. While she was in the process of doing this, Ellie turned to Clarissa.
“Want to share a ciggie?”
Clarissa nodded, and they both moved outside. Mélisande was about to lead him out, when she glimpsed something lying in the big pony suit bag which Clarissa had left on a shelf behind Bobby. It was the pump used to inflate his butt-plug – simply a squeezable rubber bulb and tube. She hesitated, but only for a moment. It could be useful. She grabbed it and stuffed it in her rucksack. No-one would miss it, and she could put it back that evening. Assuming a demure expression, she took Bobby’s bridle.
“Come on, Bobby…”
She led him out into the sunshine.
She couldn’t wait to get going. She got mounted – the stirrups needed minor lengthening. May be her legs had got a bit longer even in a few weeks. It was a lovely crisp, bright autumn day. Perfect weather for a long country hack.
“Now have you got everything darling?”
“Yes mummy, thank you.” (“Absolutely everything,” she thought.)
“Thank you, Ellie.”
“No problem, Mellie. Have a nice day. It’ll do Bobby good too to get out of that boot parlour and get some fresh air.”
Mélisande gave him a gentle kick in the sides, and he trotted forward, down the hill, past the end of the stable block, and onto the track leading through the forest into open country…
Clarissa and Ellie watched them pass through the gate and disappear. Clarissa wore a slightly sentimental smile.
“She’s been missing Bobby the Pony these past weeks. It was kind of Miss Poole to allow him some time off from work. I hope he enjoys tomorrow as well.”
“Whether he does or not, he doesn’t have a choice,” replied Ellie. “I believe Miss Poole wants to make these pony weekends a regular thing. That’ll be nice for Mellie. Just between you and me, I believe it’s all part of a plan to separate the boys some of the time. She was unhappy that together they seemed to be getting too close and too respected by the other staff. She doesn’t like that. Also I think she’s got plans for Tim as well.”
“Really?”
“Oh yes, Clarissa. I can’t go into details, but from what I overheard she’s cooking up something with Serena’s mother, who’s an old friend of hers, and runs some sort of recruitment business. I believe this weekend is the start of Tim’s “training” – though as what I have no idea yet.”
While Ellie and Clarissa got him into his suit behind the closed door of stable thirteen, Mélisande stood outside. She tossed her whip onto the ground whilst she strapped on her helmet and pulled on her leather gloves. She reminisced about her first ride on Bobby, at the top of that very field. She smiled. What a sulky little brat she’d been then! At first she had even refused to mount him! Thank goodness she’d had a change of heart - though it was only out of vanity, to show off her riding skills in front of an audience. But it’d been so much fun riding a boy-pony instead of a real pony she’d been hooked from that moment.
After ten minutes or so, the door opened and Clarissa stuck her head out.
“Darling? He’s virtually ready. Would you like to put on his hoods and tack him up?”
She went inside. There he was, transformed into a little grey pony, just how she liked him. She began with the moulded whole-head cream latex hood – the one Clarissa had packed. It slipped on quite easily. It had a neckpiece that helped to keep it firmly in position. She adjusted the fit so all the holes were in the right places and the nostril flanges were holding the nostrils open. Then the pony hood itself, with its little mane and furry ears. Then the bridle with its head-straps, which she attached to the side-rings of the rubber bit. Then the neck strap, a single strap threaded through both rings and buckled at the back of the neck, which she tightened so as to pull the bit firmly into Bobby’s mouth. Finally she clipped the reins to the rings. Then it only remained to put the saddle in place, tighten the girths, and let down the stirrups. While she was in the process of doing this, Ellie turned to Clarissa.
“Want to share a ciggie?”
Clarissa nodded, and they both moved outside. Mélisande was about to lead him out, when she glimpsed something lying in the big pony suit bag which Clarissa had left on a shelf behind Bobby. It was the pump used to inflate his butt-plug – simply a squeezable rubber bulb and tube. She hesitated, but only for a moment. It could be useful. She grabbed it and stuffed it in her rucksack. No-one would miss it, and she could put it back that evening. Assuming a demure expression, she took Bobby’s bridle.
“Come on, Bobby…”
She led him out into the sunshine.
She couldn’t wait to get going. She got mounted – the stirrups needed minor lengthening. May be her legs had got a bit longer even in a few weeks. It was a lovely crisp, bright autumn day. Perfect weather for a long country hack.
“Now have you got everything darling?”
“Yes mummy, thank you.” (“Absolutely everything,” she thought.)
“Thank you, Ellie.”
“No problem, Mellie. Have a nice day. It’ll do Bobby good too to get out of that boot parlour and get some fresh air.”
Mélisande gave him a gentle kick in the sides, and he trotted forward, down the hill, past the end of the stable block, and onto the track leading through the forest into open country…
Clarissa and Ellie watched them pass through the gate and disappear. Clarissa wore a slightly sentimental smile.
“She’s been missing Bobby the Pony these past weeks. It was kind of Miss Poole to allow him some time off from work. I hope he enjoys tomorrow as well.”
“Whether he does or not, he doesn’t have a choice,” replied Ellie. “I believe Miss Poole wants to make these pony weekends a regular thing. That’ll be nice for Mellie. Just between you and me, I believe it’s all part of a plan to separate the boys some of the time. She was unhappy that together they seemed to be getting too close and too respected by the other staff. She doesn’t like that. Also I think she’s got plans for Tim as well.”
“Really?”
“Oh yes, Clarissa. I can’t go into details, but from what I overheard she’s cooking up something with Serena’s mother, who’s an old friend of hers, and runs some sort of recruitment business. I believe this weekend is the start of Tim’s “training” – though as what I have no idea yet.”
24
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 11, 2025, 08:08:39 AM »
Chapter 268.
Mélisande was frustrated. She had been to Pitt’s Wood several times since the show, but Bobby had always been busy with work, or off somewhere with May. Riding ordinary ponies and horses was of course her favourite occupation, but the hacks at the Centre were, as riding-school mounts usually are, animals of habit and routine, happy to amble around their wonted routes with total compliance to their riders’ wishes. Riding Bobby was different. There was always that element of resistance, even rebellion, under the surface; and this had become more marked as he got older and became more conscious of the humiliation of his position. But this tension between her and her mount was what made it such fun. More – since she had confirmed her suspicions about his tail, and discovered the conformation of at least one of his “special” bits, the idea of getting on his back again had become all the more exciting. When on Friday afternoon her mother was in the loose box packing the big bag with his pony suit and accessories, she had affected indifference, but as soon as Clarissa was busy in the house she sneaked out and went through the contents. Oh, that tail! Just as she had suspected. She experimented with the pump, her eyes widening with disbelief as the rubber bladder inflated into a taut, firm oval. So that was what kept it in place! She laughed. How clever! She delved further. Ah, yes. His rubber pony bit, the flattened ends that fitted between his teeth attached to the bridle side-rings, which would then be held in place by the neck-strap, and be attached to the bridle and reins. All correct there. His whole-head anonymity hood, in fine cream moulded latex, with eye and mouth apertures and nostril holes and flanges. His little saddle and the attached stirrups were in a separate bag. She smiled. He would be hers to ride where she wanted for a whole day! She rose, and was about to leave, when she noticed the tack cupboard door was slightly open.
“Oh. Mummy forgot to lock it. She’s even left the key in.”
She went to close it, but something inside caught her attention, and reminded her of an earlier discovery. A pile of clear plastic bags, each containing other whole-head masks.
“I wonder if there’s that one I found before, when I was with Charlotte and Amelia at the arena…”
She leafed through them. At the bottom of the pile were several bulky ones. She pulled one out, and knew at once it was a “special” – she could feel the lump inside. She carefully took it out of its bag, and opened the neck. Sure enough, there was the gag inside. She felt it. This one was solid rubber. “How rude! Imagine having to suc-k on that…” She giggled. She held the hood up. The only apertures were at the nostrils – two little round holes with internal flanges to keep the nostrils wide open. She contemplated it for a moment. “I wonder if…” She searched around, and found what she was looking for. A pair of side-rings joined by a short broad leather strap, clearly designed for use with such a hood to brace the rings and keep the gag firmly in place. In conjunction with the closed eyes, the perfect bridle for training a pony into total unquestioning obedience to its rider. Being blind and unable to pull on its bit, it would have no choice but to respond to the aids and instructions. It only took a second for her to make a decision. She stuffed the hood and modified rings into her pocket, left the cupboard as she had found it, and returned to the house, whistling innocently.
She was up at five, hurriedly put on her riding gear – her standard outfit of cream breeches and black rubber boots with a T-shirt and warm puffy jacket. She gobbled down breakfast, hassling Clarissa to hurry up so they could arrive early at Pitt’s Wood. She had packed her rucksack the previous night, and secreted her acquisitions in a side-pocket. She held her breath as her mother packed her and Bobby’s lunchboxes and drinks into the main compartment. She grabbed her riding helmet and they were soon on the road.
“Mummy? Will I be able to help tack up Bobby?”
“Of course. Tacking him up is your job.”
“And help getting him into his pony suit?”
“Mellie, darling, you know that’s not a suitable job for you. Ellie and I are responsible for all that.”
“Ooh, but mummy…when will I be allowed to get him ready…?” she whined, but with a faint smile on her face.
“I’ve told you. When you’re older.”
“How much older?”
“A lot older. Now stop asking questions which you already know the answer to.”
“Okay… But why….?”
“Mélisande!”
“Sorry, mummy…”
The car park was virtually empty at this early hour. They strolled down the path towards stable 13. A few of the stable staff were mucking out, horses cropping the grass in the field. Bobby and Ellie were already there, waiting outside. Mélisande ran on ahead and jumped bodily into Bobby’s arms. He caught her, laughing.
“Whoa, Mellie! You’ve put on weight!”
“I’m growing, idiot!”
“Bad news for me.”
“No – good exercise for you. Ponies need to be ridden regularly. It’s been too long.”
“Well, you got me at last.”
Mélisande smiled. Yes, she’d got him – and she was going to make the most of it.
Mélisande was frustrated. She had been to Pitt’s Wood several times since the show, but Bobby had always been busy with work, or off somewhere with May. Riding ordinary ponies and horses was of course her favourite occupation, but the hacks at the Centre were, as riding-school mounts usually are, animals of habit and routine, happy to amble around their wonted routes with total compliance to their riders’ wishes. Riding Bobby was different. There was always that element of resistance, even rebellion, under the surface; and this had become more marked as he got older and became more conscious of the humiliation of his position. But this tension between her and her mount was what made it such fun. More – since she had confirmed her suspicions about his tail, and discovered the conformation of at least one of his “special” bits, the idea of getting on his back again had become all the more exciting. When on Friday afternoon her mother was in the loose box packing the big bag with his pony suit and accessories, she had affected indifference, but as soon as Clarissa was busy in the house she sneaked out and went through the contents. Oh, that tail! Just as she had suspected. She experimented with the pump, her eyes widening with disbelief as the rubber bladder inflated into a taut, firm oval. So that was what kept it in place! She laughed. How clever! She delved further. Ah, yes. His rubber pony bit, the flattened ends that fitted between his teeth attached to the bridle side-rings, which would then be held in place by the neck-strap, and be attached to the bridle and reins. All correct there. His whole-head anonymity hood, in fine cream moulded latex, with eye and mouth apertures and nostril holes and flanges. His little saddle and the attached stirrups were in a separate bag. She smiled. He would be hers to ride where she wanted for a whole day! She rose, and was about to leave, when she noticed the tack cupboard door was slightly open.
“Oh. Mummy forgot to lock it. She’s even left the key in.”
She went to close it, but something inside caught her attention, and reminded her of an earlier discovery. A pile of clear plastic bags, each containing other whole-head masks.
“I wonder if there’s that one I found before, when I was with Charlotte and Amelia at the arena…”
She leafed through them. At the bottom of the pile were several bulky ones. She pulled one out, and knew at once it was a “special” – she could feel the lump inside. She carefully took it out of its bag, and opened the neck. Sure enough, there was the gag inside. She felt it. This one was solid rubber. “How rude! Imagine having to suc-k on that…” She giggled. She held the hood up. The only apertures were at the nostrils – two little round holes with internal flanges to keep the nostrils wide open. She contemplated it for a moment. “I wonder if…” She searched around, and found what she was looking for. A pair of side-rings joined by a short broad leather strap, clearly designed for use with such a hood to brace the rings and keep the gag firmly in place. In conjunction with the closed eyes, the perfect bridle for training a pony into total unquestioning obedience to its rider. Being blind and unable to pull on its bit, it would have no choice but to respond to the aids and instructions. It only took a second for her to make a decision. She stuffed the hood and modified rings into her pocket, left the cupboard as she had found it, and returned to the house, whistling innocently.
She was up at five, hurriedly put on her riding gear – her standard outfit of cream breeches and black rubber boots with a T-shirt and warm puffy jacket. She gobbled down breakfast, hassling Clarissa to hurry up so they could arrive early at Pitt’s Wood. She had packed her rucksack the previous night, and secreted her acquisitions in a side-pocket. She held her breath as her mother packed her and Bobby’s lunchboxes and drinks into the main compartment. She grabbed her riding helmet and they were soon on the road.
“Mummy? Will I be able to help tack up Bobby?”
“Of course. Tacking him up is your job.”
“And help getting him into his pony suit?”
“Mellie, darling, you know that’s not a suitable job for you. Ellie and I are responsible for all that.”
“Ooh, but mummy…when will I be allowed to get him ready…?” she whined, but with a faint smile on her face.
“I’ve told you. When you’re older.”
“How much older?”
“A lot older. Now stop asking questions which you already know the answer to.”
“Okay… But why….?”
“Mélisande!”
“Sorry, mummy…”
The car park was virtually empty at this early hour. They strolled down the path towards stable 13. A few of the stable staff were mucking out, horses cropping the grass in the field. Bobby and Ellie were already there, waiting outside. Mélisande ran on ahead and jumped bodily into Bobby’s arms. He caught her, laughing.
“Whoa, Mellie! You’ve put on weight!”
“I’m growing, idiot!”
“Bad news for me.”
“No – good exercise for you. Ponies need to be ridden regularly. It’s been too long.”
“Well, you got me at last.”
Mélisande smiled. Yes, she’d got him – and she was going to make the most of it.
25
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 11, 2025, 08:02:42 AM »
Chapter 267.
The day proceeded satisfactorily. All the women were so attentive to him, asking him about his work, his friends, and life at Pitt’s Wood generally, all promising to book a session as soon as they had time. After lunch, which Tim helped to serve, Cassandra seated herself in an armchair with a glass of wine on a table by her side, and beckoned to Tim. She patted her lap.
“Sit with me for a bit, Timothy…”
“I’m too ‘eavy, Mrs Egerton…”
“Not at all. Come on, sit down.”
He lowered himself gingerly onto her lap.
“See? Comfy? You’re as light as a feather.”
She was a biggish woman, and her legs did seem very robust…
“Now, tell me all about your boot-cleaning exploits, and your friend Bobby. Is it true he too looks good in a dress?”
“Oh, er, yes, er miss… ‘E looks fantastic. There’s a pitcher on my phone…”
“It’s in the bedroom. I’ll bring it,” said Doreen, jumping up.
“And you both wear little pageboy uniforms, I hear…”
“Er, yeah…”
“With little tight latex shorts…”
“…yeah…”
“Actually I’m teasing. Serena showed me the photos. Darling, you both look so cute. The girls at the Centre must be falling over themselves…”
Tim gave a nervous laugh. Doreen returned with the phone. Tim scrolled to a picture of Tim in his dress. He showed it to Cassandra. The effect was quite startling. He felt her stiffen.
“Oh my god!” She stared at Tim’s phone. “Is that actually…a boy?”
“Yeah… That’s Bobby aw right…”
“Doreen. Show the others. We need him…” She stopped suddenly. “I mean, we should really invite both of you, sometime… You’re such good friends, after all… We could find lots of new dresses for you…”
“’E’d like that,” laughed Tim. “’E loves ’is girlie fings…”
“Yes…” she said, apparently more to herself than to the company. “Yes… I should speak to Violet about it…”
“Miss Poole?” said Tim, innocently.
“Oh…”
“Miss Poole one of mum’s oldest friends,” put in Serena, by way of explanation. “How do you think I got that session, and was able to book this weekend so quickly?”
“Oh, yeah, I see…”
Cassandra’s free hand rested itself on Tim’s thigh, rather too high up for comfort. In response he instinctively placed his hands on his skirt, just as if he was a demure girl. She appeared not to notice.
“Now Timothy, my friends and I are all going away for a little hol this evening, so unfortunately we won’t be here tomorrow. But Serena and her friends will take good care of you. Do you promise to be a good boy – or a good girl – and do everything they ask?” Tim nodded. “I know you will. Because I would like to renew our acquaintance as soon as possible. We all do. Don’t be intimidated, will you? I know it must feel odd being surrounded by women without your best friend at your side…”
“It’s okay, miss…really…”
“You’ll have a friend tomorrow, I’m hoping,” said Serena. “Nicola’s coming, and she said she’ll bring Terry.”
“Oh, good! Excellent!” cried Cassandra. “He can show Timothy the ropes…”
“Yes, mum,” said Serena, with a slight frown. “He can show him how to repel unwanted attention…”
Tim felt slightly puzzled. But he was feeling slightly outnumbered, and the prospect of a male friend appealed.
“Can you curtsey?” asked Cassandra, suddenly.
Tim smiled uneasily. “Never really tried…”
“Lucille, you’re the deportment expert. Would you like to…?”
“Delighted, Cassandra. Here, young man. Stand up over by the bookcase. That’s it. Now… First of all take the hem of your dress each side between finger and thumb, as delicately as you can. Yes…just hold it lightly, no stress. Smile and keep smiling. Not that much, silly! Yes, that’s better. Now, I want you to bend your knees…slowly…just a little…while all the time holding you skirt at the same distance from the ground. It’s not easy. Your body will descend slightly, but your hands keep their level, so the skirt rises slightly relative to you. Try it…”
The entire afternoon, until the early supper which predicated the ladies’ departure, was occupied with Tim’s education in things female. There was curtseying, deportment – with a book on his head! – correct movement in walking, greeting, picking things up from the floor, correct speech – polite, measured, light in tone and substance, accompanied by “appropriate” facial expressions - and even some basic advice on dress and makeup, though Cassandra mentioned these topics were so important that other days would be set aside for their pursuit. Tim was quite exhausted at the end of it, and puzzled as to the point of the whole exercise. It was as if he was being trained for something! But what that could be, he had no idea.
After Cassandra and her friends had left for their vacation, and he was alone with Serena, he plucked up the courage to ask.
“Serena… Why did I ‘ave to do all that stuff for yer mum?
“Oh, I’ll explain everything tomorrow. Now come and sit with me. Let’s have a drink. I want you to tell me all about what you and Bobby get up to in the boot parlour. It’s been a while now. Are you enjoying it?”
“Oh… Well, yeah, I guess… See, I ain’t never ‘ad my own place before… I don’t wanna go ‘ome again… It feels like we’ve suddenly grown up…”
“And you have such cool outfits…”
“Yeah…”
“But dresses aren’t so bad, are they?”
“No… It feels so light… An’ all the little fings girls can wear, earrings and bangles…and the makeup an’ stuff… An’ perfume…”
“You like that?”
Serena seemed genuinely interested. She was much nicer that he had thought originally. She had her arm round his shoulders and was smiling at him. He felt he could tell her anything, more than anyone else he knew. He began to open up.
“Yeah…guess so. Before I fought it was sissy. But then I saw Bobby in ‘is dress… He looks so pretty! An’ now I can see why ‘e likes it. It makes yer feel so sor’ of…perfec… I was surprised ‘ow amazin’ I look…like I almost wanna go out and show it off to everyone…”
“That’s so cool! Well, Tim, tomorrow you’ll have a new outfit. I can’t wait to see you in it. No, no… It’s a secret. But I know you’re going to love it…”
Serena helped him get ready for bed. She had a pretty pale pink nightie for him. He was a little embarrassed because his coc-k, rebelling against its confinement, had been leaking prec-um all the afternoon, making his pretty satin panties all slimy. So to protect his nightie and the sheets, Serena put a condom over the whole lot.
As he lay in bed that night, in the fussy room, on perfumed sheets, wearing his frilly nightie, he wondered what Serena’s friends would be like. He felt that they couldn’t be as demanding as her mother’s crowd. And he was looking forward to meeting this Terry…
The day proceeded satisfactorily. All the women were so attentive to him, asking him about his work, his friends, and life at Pitt’s Wood generally, all promising to book a session as soon as they had time. After lunch, which Tim helped to serve, Cassandra seated herself in an armchair with a glass of wine on a table by her side, and beckoned to Tim. She patted her lap.
“Sit with me for a bit, Timothy…”
“I’m too ‘eavy, Mrs Egerton…”
“Not at all. Come on, sit down.”
He lowered himself gingerly onto her lap.
“See? Comfy? You’re as light as a feather.”
She was a biggish woman, and her legs did seem very robust…
“Now, tell me all about your boot-cleaning exploits, and your friend Bobby. Is it true he too looks good in a dress?”
“Oh, er, yes, er miss… ‘E looks fantastic. There’s a pitcher on my phone…”
“It’s in the bedroom. I’ll bring it,” said Doreen, jumping up.
“And you both wear little pageboy uniforms, I hear…”
“Er, yeah…”
“With little tight latex shorts…”
“…yeah…”
“Actually I’m teasing. Serena showed me the photos. Darling, you both look so cute. The girls at the Centre must be falling over themselves…”
Tim gave a nervous laugh. Doreen returned with the phone. Tim scrolled to a picture of Tim in his dress. He showed it to Cassandra. The effect was quite startling. He felt her stiffen.
“Oh my god!” She stared at Tim’s phone. “Is that actually…a boy?”
“Yeah… That’s Bobby aw right…”
“Doreen. Show the others. We need him…” She stopped suddenly. “I mean, we should really invite both of you, sometime… You’re such good friends, after all… We could find lots of new dresses for you…”
“’E’d like that,” laughed Tim. “’E loves ’is girlie fings…”
“Yes…” she said, apparently more to herself than to the company. “Yes… I should speak to Violet about it…”
“Miss Poole?” said Tim, innocently.
“Oh…”
“Miss Poole one of mum’s oldest friends,” put in Serena, by way of explanation. “How do you think I got that session, and was able to book this weekend so quickly?”
“Oh, yeah, I see…”
Cassandra’s free hand rested itself on Tim’s thigh, rather too high up for comfort. In response he instinctively placed his hands on his skirt, just as if he was a demure girl. She appeared not to notice.
“Now Timothy, my friends and I are all going away for a little hol this evening, so unfortunately we won’t be here tomorrow. But Serena and her friends will take good care of you. Do you promise to be a good boy – or a good girl – and do everything they ask?” Tim nodded. “I know you will. Because I would like to renew our acquaintance as soon as possible. We all do. Don’t be intimidated, will you? I know it must feel odd being surrounded by women without your best friend at your side…”
“It’s okay, miss…really…”
“You’ll have a friend tomorrow, I’m hoping,” said Serena. “Nicola’s coming, and she said she’ll bring Terry.”
“Oh, good! Excellent!” cried Cassandra. “He can show Timothy the ropes…”
“Yes, mum,” said Serena, with a slight frown. “He can show him how to repel unwanted attention…”
Tim felt slightly puzzled. But he was feeling slightly outnumbered, and the prospect of a male friend appealed.
“Can you curtsey?” asked Cassandra, suddenly.
Tim smiled uneasily. “Never really tried…”
“Lucille, you’re the deportment expert. Would you like to…?”
“Delighted, Cassandra. Here, young man. Stand up over by the bookcase. That’s it. Now… First of all take the hem of your dress each side between finger and thumb, as delicately as you can. Yes…just hold it lightly, no stress. Smile and keep smiling. Not that much, silly! Yes, that’s better. Now, I want you to bend your knees…slowly…just a little…while all the time holding you skirt at the same distance from the ground. It’s not easy. Your body will descend slightly, but your hands keep their level, so the skirt rises slightly relative to you. Try it…”
The entire afternoon, until the early supper which predicated the ladies’ departure, was occupied with Tim’s education in things female. There was curtseying, deportment – with a book on his head! – correct movement in walking, greeting, picking things up from the floor, correct speech – polite, measured, light in tone and substance, accompanied by “appropriate” facial expressions - and even some basic advice on dress and makeup, though Cassandra mentioned these topics were so important that other days would be set aside for their pursuit. Tim was quite exhausted at the end of it, and puzzled as to the point of the whole exercise. It was as if he was being trained for something! But what that could be, he had no idea.
After Cassandra and her friends had left for their vacation, and he was alone with Serena, he plucked up the courage to ask.
“Serena… Why did I ‘ave to do all that stuff for yer mum?
“Oh, I’ll explain everything tomorrow. Now come and sit with me. Let’s have a drink. I want you to tell me all about what you and Bobby get up to in the boot parlour. It’s been a while now. Are you enjoying it?”
“Oh… Well, yeah, I guess… See, I ain’t never ‘ad my own place before… I don’t wanna go ‘ome again… It feels like we’ve suddenly grown up…”
“And you have such cool outfits…”
“Yeah…”
“But dresses aren’t so bad, are they?”
“No… It feels so light… An’ all the little fings girls can wear, earrings and bangles…and the makeup an’ stuff… An’ perfume…”
“You like that?”
Serena seemed genuinely interested. She was much nicer that he had thought originally. She had her arm round his shoulders and was smiling at him. He felt he could tell her anything, more than anyone else he knew. He began to open up.
“Yeah…guess so. Before I fought it was sissy. But then I saw Bobby in ‘is dress… He looks so pretty! An’ now I can see why ‘e likes it. It makes yer feel so sor’ of…perfec… I was surprised ‘ow amazin’ I look…like I almost wanna go out and show it off to everyone…”
“That’s so cool! Well, Tim, tomorrow you’ll have a new outfit. I can’t wait to see you in it. No, no… It’s a secret. But I know you’re going to love it…”
Serena helped him get ready for bed. She had a pretty pale pink nightie for him. He was a little embarrassed because his coc-k, rebelling against its confinement, had been leaking prec-um all the afternoon, making his pretty satin panties all slimy. So to protect his nightie and the sheets, Serena put a condom over the whole lot.
As he lay in bed that night, in the fussy room, on perfumed sheets, wearing his frilly nightie, he wondered what Serena’s friends would be like. He felt that they couldn’t be as demanding as her mother’s crowd. And he was looking forward to meeting this Terry…
26
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 11, 2025, 07:53:44 AM »
Chapter 266.
Serena appeared in the doorway. She took one look at Tim and her face lit up.
“Tim! You look gorgeous! Carly, open the wardrobe door so he can see himself in the full-length mirror.”
Carly opened the door and Tim turned to face it. He looked at himself with quiet satisfaction, a little smile of pleasure on his face. He could feel the three women staring, and it gave him a strange physical thrill. He turned his body slightly one way, then the other, making his light, bouncy skirt swirl. For the first time he felt pressure in his device; it was lifting, pushing against his panties, as though he was becoming aroused by his own reflection. He ran his hands down the bodice of the dress, enjoying the feel of the smooth, silky satin. He felt slightly breathless.
“Come and show my mum and the others. Would you do that?”
“Sure…”
Yes, now he wanted to show off to as many people as possible, to feel their gazes and see the admiration in their eyes. In some ways this felt even better than showing off in his pageboy outfit - more subtle somehow. He felt in a state of heightened excitement, his tightly-constricted boyhood generating a barely tolerable level of tension, making him feel light and tingly, and forcing him to move with a sort of controlled delicacy, so adding to the sense of girlishness. As Serena led him down the corridor towards the sounds of conversation and laughter, the combination of these internal feelings, and the sensations of the soft, light fabrics against his skin, and the earrings nipping his earlobes, produced a feeling of taut sustained exhilaration. His eyes sparkled and his cheeks were slightly flushed as he entered the living room. As he appeared, three faces turned, and conversation abruptly ceased.
The three women, two middle-aged, one slightly younger, stared, mouths still open in mid-speech. There was a split second of surprise, but each one quickly suppressed it in favour of as natural a welcome as they could muster, in the form of a smile in which the eyes did not partake.
“Mum…ladies…this is Tim. Tim, my mother, …and her friends…”
One of the older women advanced and took Tim’s hand. She held it firmly and looked searchingly into his face with a rather hard and calculating blue eye.
“Timothy…such a pleasure to meet you at last… I’m Cassandra Egerton.” She indicated the other woman of a similar age. “This is my oldest friend, Lucille, and my friend and work colleague Sasha.” She took a breath, and looked him up and down. “You really are a beauty,” she remarked, (somewhat dispassionately, as if she were talking about a horse), “but of course my daughter shares my exquisite taste. She was right when she said you were something rather special.”
Tim, deaf to the tone of these remarks, heard only the praise, and flushed with pride.
“Carly…Doreen. You’ve excelled yourselves! Not only is this a beautiful outfit, but it suits Timothy to perfection. All the trimmings, too…”
She caught her daughter’s eye.
“Excuse me, Timothy…”
She grabbed Serena’s arm and pulled her aside. Tim heard sounds of approval. He also thought he heard the phrase “ideal material”. But he may have been wrong…
Serena appeared in the doorway. She took one look at Tim and her face lit up.
“Tim! You look gorgeous! Carly, open the wardrobe door so he can see himself in the full-length mirror.”
Carly opened the door and Tim turned to face it. He looked at himself with quiet satisfaction, a little smile of pleasure on his face. He could feel the three women staring, and it gave him a strange physical thrill. He turned his body slightly one way, then the other, making his light, bouncy skirt swirl. For the first time he felt pressure in his device; it was lifting, pushing against his panties, as though he was becoming aroused by his own reflection. He ran his hands down the bodice of the dress, enjoying the feel of the smooth, silky satin. He felt slightly breathless.
“Come and show my mum and the others. Would you do that?”
“Sure…”
Yes, now he wanted to show off to as many people as possible, to feel their gazes and see the admiration in their eyes. In some ways this felt even better than showing off in his pageboy outfit - more subtle somehow. He felt in a state of heightened excitement, his tightly-constricted boyhood generating a barely tolerable level of tension, making him feel light and tingly, and forcing him to move with a sort of controlled delicacy, so adding to the sense of girlishness. As Serena led him down the corridor towards the sounds of conversation and laughter, the combination of these internal feelings, and the sensations of the soft, light fabrics against his skin, and the earrings nipping his earlobes, produced a feeling of taut sustained exhilaration. His eyes sparkled and his cheeks were slightly flushed as he entered the living room. As he appeared, three faces turned, and conversation abruptly ceased.
The three women, two middle-aged, one slightly younger, stared, mouths still open in mid-speech. There was a split second of surprise, but each one quickly suppressed it in favour of as natural a welcome as they could muster, in the form of a smile in which the eyes did not partake.
“Mum…ladies…this is Tim. Tim, my mother, …and her friends…”
One of the older women advanced and took Tim’s hand. She held it firmly and looked searchingly into his face with a rather hard and calculating blue eye.
“Timothy…such a pleasure to meet you at last… I’m Cassandra Egerton.” She indicated the other woman of a similar age. “This is my oldest friend, Lucille, and my friend and work colleague Sasha.” She took a breath, and looked him up and down. “You really are a beauty,” she remarked, (somewhat dispassionately, as if she were talking about a horse), “but of course my daughter shares my exquisite taste. She was right when she said you were something rather special.”
Tim, deaf to the tone of these remarks, heard only the praise, and flushed with pride.
“Carly…Doreen. You’ve excelled yourselves! Not only is this a beautiful outfit, but it suits Timothy to perfection. All the trimmings, too…”
She caught her daughter’s eye.
“Excuse me, Timothy…”
She grabbed Serena’s arm and pulled her aside. Tim heard sounds of approval. He also thought he heard the phrase “ideal material”. But he may have been wrong…
27
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on November 10, 2025, 05:16:52 PM »
The Pledge
Madison began to speak in a dramatic tone, “Tonight, we are all privileged to witness a rare ceremony. The candidates before you will make their solemn promise to Gamma Delta... in the Alexionian Society.”
At the mention of the Alexionian Society, an audible wave of excitement and anticipation seemed to sweep through the gathered Sisters. The air was suddenly electric. Members exchanged excited, knowing glances. Several clasped their hands in eager energy, and they all appeared to be fully aware of something significant about to unfold.
Watching this reaction, the four emasculated boys stood frozen at the front of the room, their faces pale with apprehension. They were incredibly confused and mortified. Still wildly uncomfortable in their new feminine skins, each boy felt the weight of curious, excited eyes upon them. They felt incredibly self-conscious of their lacy undergarments and confining dancers’ belts. Their glossy pink lips shone so daintily in the candlelight and seemed to only highlight their embarrassment. The delicate fabrics of their clothing rustled sweetly. Their crisply pleated navy skirts contrasted demurely with the creamy sheen of the tights that clung snugly to their legs. Their patent Mary Janes gleamed brightly with every nervous fidget. Their hands fidgeted with the hems of their skirts or the edges of their silky cuffs, seeking some comfort in the unfamiliar attire, but finding none.
Their hearts continued to pound, and every whispered giggle from the crowd only intensified the boys’ sense of vulnerability.
Madison, sensing she had the room in the palm of her hand, savored the moment. She continued theatrically, “This pledge marks their formal commitment to our sorority and everything we stand for.” With added seriousness, she explained, “Although we refer to them informally as our ‘Little Sisters,’ they are in actuality joining the ‘Alexionian Society.’ The Society holds a beloved place in the traditions and history of Gamma Delta. Its name calls back to the ancient Greek ‘alexis,’ meaning ‘helper.’ The Alexiones play a gentle, supportive role in our Sisterhood as our devoted and faithful helpers. The Alexionian Society is incredibly exclusive. In our history, Gamma Delta has often had years where no new members of the Society were inducted. Even in our chapter here, it has been over three years since our last.”
She let that sink in. Then she announced, “Tonight, we welcome these four… yes, I said four… new members of our cherished Alexionian Society.”
The excitement in the crowd was electric.
With a commanding presence, Madison turned toward the four flustered college freshmen. Like deer caught in the headlights, they froze. The unspoken question was obvious in their panicky eyes, “The Alexionian Society…?”
“Raise your right hands and repeat after me,” Madison instructed, her tone serious and dramatic.
The boys hesitated under the scrutiny of the entire sorority, hopelessly searching one last time for an escape. Instead of a way out, however, they saw several Sisters with their phones out taking pictures and videos! The room was silent, and the tension for the four boys was excruciating. The psychological pressure on them to comply was intense, and they felt like an invisible net had suddenly tightened over them. This net had been crafted throughout the evening: Their rapid feminine transformations, the insistent guidance of their Big Sisters, the overwhelming attention to their appearance, the parade through the house, the suspenseful build-up. Each act of compliance whether it was meekly getting dressed, sitting still for makeup, or allowing themselves to be led like children had put them more off-balance. All of it had landed them here. Now, under the glare of the spotlight, there only seemed to be one path forward.
Then, each of them received a firm, purposeful squeeze of the shoulder from his new Big Sister. Once the first hand began to move, the rest followed. One by one, Nate, Milo, Julian and Owen slowly raised their nervous hands as directed.
Madison read the words aloud, clear and steady. She paused after every line for the boys to repeat:
“I solemnly swear to the Sisterhood of Gamma Delta my steadfast devotion as a member of the Alexionian Society. Grateful to be given the privilege of service, I vow to respect and follow Gamma Delta’s values. I will embrace chastity, modesty and grace in all things. I will ever seek to embody kindness, obedience and loyalty. These things I pledge with all my heart, and all my soul, to the Sisterhood of Gamma Delta.”
Each boy repeated the pledge, voices quiet and uncertain, as phone cameras flashed around them. Milo’s cheeks burned as he stumbled over the words, and Owen’s voice wavered. Nate spoke so softly he could barely be heard, and Julian’s eyes darted to the ceiling, wishing he could disappear. Their embarrassment was palpable. They’d never felt so exposed. In particular, they all seemed to choke a bit as they promised to “embrace chastity!” They felt so helpless as the walls closed in. It was only made worse knowing that every stammer and blush was being recorded for posterity. But as their last words faded, a wave of applause mixed with some laughter began sweeping through the room.
Some sisters cheered, clapping loudly and calling out praise. “Well done, Little Sisters!” someone shouted. There was teasing too. Elise winked, “Congratulations! Now you’re really in it!” Cassidy giggled, “That’s just the beginning, boys!”
Overwhelmed, the boys stood meekly as a cheerful wave of girlish affection swept over them. They received hugs, gentle pats on the back, and many ultra-feminine air kisses so as not to smudge their makeup. More than one gentle hand glided across the boys’ backs during a hug to intentionally trace the slender lines of their bra straps underneath as if doing an inspection. The air was thick with perfume and laughter. Their faces were still flushed with embarrassment, and they were disoriented by this sudden outpouring of congratulations. Their cheeks grew even rosier at each dainty “mwah!” of another sister’s air kiss wafting by their cheeks.
The boys began catching snippets of conversation that hinted of worrisome things to come. They heard more than one Sister refer to them as “Darlings,” and a couple of Sisters said they “couldn’t wait until Sunday!” The atmosphere turned almost playful, but with an edge.
It also unnerved them that more than one Sister commented on their feminized looks. Nate overheard a pair of Sisters whisper about, "those adorable cheekbones!" Milo caught a comment about "that gorgeous hair.” Julian tried not to react when one Sister said he was "too pretty to be a boy." Owen blushed to hear "His lashes are unreal. Jealous!" Each remark only amplified their discomfort, and they felt like ornaments on display. Surrounded by all these confident Sisters while dressed in their delicate skirts and blouses left them feeling outnumbered and exposed.
As the ceremony mercifully drew to a close and the room slowly emptied, their Big Sisters gathered them together and led them upstairs with gentle, guiding hands. “Now,” Tara announced with a sparkling smile, “It’s finally time for Study Hall!”
Madison began to speak in a dramatic tone, “Tonight, we are all privileged to witness a rare ceremony. The candidates before you will make their solemn promise to Gamma Delta... in the Alexionian Society.”
At the mention of the Alexionian Society, an audible wave of excitement and anticipation seemed to sweep through the gathered Sisters. The air was suddenly electric. Members exchanged excited, knowing glances. Several clasped their hands in eager energy, and they all appeared to be fully aware of something significant about to unfold.
Watching this reaction, the four emasculated boys stood frozen at the front of the room, their faces pale with apprehension. They were incredibly confused and mortified. Still wildly uncomfortable in their new feminine skins, each boy felt the weight of curious, excited eyes upon them. They felt incredibly self-conscious of their lacy undergarments and confining dancers’ belts. Their glossy pink lips shone so daintily in the candlelight and seemed to only highlight their embarrassment. The delicate fabrics of their clothing rustled sweetly. Their crisply pleated navy skirts contrasted demurely with the creamy sheen of the tights that clung snugly to their legs. Their patent Mary Janes gleamed brightly with every nervous fidget. Their hands fidgeted with the hems of their skirts or the edges of their silky cuffs, seeking some comfort in the unfamiliar attire, but finding none.
Their hearts continued to pound, and every whispered giggle from the crowd only intensified the boys’ sense of vulnerability.
Madison, sensing she had the room in the palm of her hand, savored the moment. She continued theatrically, “This pledge marks their formal commitment to our sorority and everything we stand for.” With added seriousness, she explained, “Although we refer to them informally as our ‘Little Sisters,’ they are in actuality joining the ‘Alexionian Society.’ The Society holds a beloved place in the traditions and history of Gamma Delta. Its name calls back to the ancient Greek ‘alexis,’ meaning ‘helper.’ The Alexiones play a gentle, supportive role in our Sisterhood as our devoted and faithful helpers. The Alexionian Society is incredibly exclusive. In our history, Gamma Delta has often had years where no new members of the Society were inducted. Even in our chapter here, it has been over three years since our last.”
She let that sink in. Then she announced, “Tonight, we welcome these four… yes, I said four… new members of our cherished Alexionian Society.”
The excitement in the crowd was electric.
With a commanding presence, Madison turned toward the four flustered college freshmen. Like deer caught in the headlights, they froze. The unspoken question was obvious in their panicky eyes, “The Alexionian Society…?”
“Raise your right hands and repeat after me,” Madison instructed, her tone serious and dramatic.
The boys hesitated under the scrutiny of the entire sorority, hopelessly searching one last time for an escape. Instead of a way out, however, they saw several Sisters with their phones out taking pictures and videos! The room was silent, and the tension for the four boys was excruciating. The psychological pressure on them to comply was intense, and they felt like an invisible net had suddenly tightened over them. This net had been crafted throughout the evening: Their rapid feminine transformations, the insistent guidance of their Big Sisters, the overwhelming attention to their appearance, the parade through the house, the suspenseful build-up. Each act of compliance whether it was meekly getting dressed, sitting still for makeup, or allowing themselves to be led like children had put them more off-balance. All of it had landed them here. Now, under the glare of the spotlight, there only seemed to be one path forward.
Then, each of them received a firm, purposeful squeeze of the shoulder from his new Big Sister. Once the first hand began to move, the rest followed. One by one, Nate, Milo, Julian and Owen slowly raised their nervous hands as directed.
Madison read the words aloud, clear and steady. She paused after every line for the boys to repeat:
“I solemnly swear to the Sisterhood of Gamma Delta my steadfast devotion as a member of the Alexionian Society. Grateful to be given the privilege of service, I vow to respect and follow Gamma Delta’s values. I will embrace chastity, modesty and grace in all things. I will ever seek to embody kindness, obedience and loyalty. These things I pledge with all my heart, and all my soul, to the Sisterhood of Gamma Delta.”
Each boy repeated the pledge, voices quiet and uncertain, as phone cameras flashed around them. Milo’s cheeks burned as he stumbled over the words, and Owen’s voice wavered. Nate spoke so softly he could barely be heard, and Julian’s eyes darted to the ceiling, wishing he could disappear. Their embarrassment was palpable. They’d never felt so exposed. In particular, they all seemed to choke a bit as they promised to “embrace chastity!” They felt so helpless as the walls closed in. It was only made worse knowing that every stammer and blush was being recorded for posterity. But as their last words faded, a wave of applause mixed with some laughter began sweeping through the room.
Some sisters cheered, clapping loudly and calling out praise. “Well done, Little Sisters!” someone shouted. There was teasing too. Elise winked, “Congratulations! Now you’re really in it!” Cassidy giggled, “That’s just the beginning, boys!”
Overwhelmed, the boys stood meekly as a cheerful wave of girlish affection swept over them. They received hugs, gentle pats on the back, and many ultra-feminine air kisses so as not to smudge their makeup. More than one gentle hand glided across the boys’ backs during a hug to intentionally trace the slender lines of their bra straps underneath as if doing an inspection. The air was thick with perfume and laughter. Their faces were still flushed with embarrassment, and they were disoriented by this sudden outpouring of congratulations. Their cheeks grew even rosier at each dainty “mwah!” of another sister’s air kiss wafting by their cheeks.
The boys began catching snippets of conversation that hinted of worrisome things to come. They heard more than one Sister refer to them as “Darlings,” and a couple of Sisters said they “couldn’t wait until Sunday!” The atmosphere turned almost playful, but with an edge.
It also unnerved them that more than one Sister commented on their feminized looks. Nate overheard a pair of Sisters whisper about, "those adorable cheekbones!" Milo caught a comment about "that gorgeous hair.” Julian tried not to react when one Sister said he was "too pretty to be a boy." Owen blushed to hear "His lashes are unreal. Jealous!" Each remark only amplified their discomfort, and they felt like ornaments on display. Surrounded by all these confident Sisters while dressed in their delicate skirts and blouses left them feeling outnumbered and exposed.
As the ceremony mercifully drew to a close and the room slowly emptied, their Big Sisters gathered them together and led them upstairs with gentle, guiding hands. “Now,” Tara announced with a sparkling smile, “It’s finally time for Study Hall!”
28
Active Sissy Stories / Re: The Village
« Last post by BabyJay on November 07, 2025, 12:10:02 PM »
WOW!!!!!. The mind boggles, all those slutty nymphomaniacs and those sex mad toddlers. sounds like the park will soon be a tangled mass of humping bodies. Looking forward to next chapters
29
Active Sissy Stories / Re: Peter was a petty criminal
« Last post by BabyJay on November 07, 2025, 04:52:03 AM »
Oh dear!! Caught in the act. I dread to think what punishment is in store for them. something very unpleasant and humiliating I imagine. Looking forward to continuation.
30
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by BabyJay on November 07, 2025, 04:41:02 AM »
Delightful. Loved the photo of the 'Little Sisters' so cute and demure in their school uniforms. Now that they are being introduced to the rest of the Big girls I think their humiliation and embarrassment is just beginning. Wonder how they will be dressed when they go shopping for their pretty frilly and lacey lingerie?
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