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Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on Today at 06:04:59 PM »
A Gamma Delta Primer
When the hour reached eight, Madison cheerfully announced that it was time for the boys to get their first lesson in the history and lore of Gamma Delta. Most of the other Sisters in the room turned their chairs to watch. Madison then produced a neat stack of study packets. The booklet covers were stamped with the sorority crest, and she distributed them with the flourish of someone unveiling treasure. Her voice took on an air of ceremony. “Tonight, you’ll begin to appreciate what it means to be part of the Gamma Delta fold. This isn’t just a sorority—it’s a tradition, a legacy, and a family. And as our Little Sisters, the newest members of the Alexionian Society, you are going to learn all about our history, values, and what makes Gamma Delta special.”
The boys exchanged pained looks as their Big Sisters gathered around, ready to guide where needed. Madison’s tone grew even more serious as she continued: “I want you to understand that starting now, you must apply yourselves with the utmost diligence. Mastering all the material in these packets is not optional. You will be expected to know by heart every aspect of Gamma Delta history, tradition, and lore.”
Madison let that sink in, and then she began the lesson, her tone serious. “Let’s start with our motto: ‘Sisterhood in Service and Strength.’ It’s more than words. It’s a promise that every member supports one another and works toward bettering themselves and the community.” She pointed to a banner overhead, where the Greek letters ?? were displayed in elegant gold script. “Gamma Delta—those letters stand for ‘growth and change,’ the twin pillars upon which all our rituals and goals rest.”
Madison then instructed the boys to open their packets to the first section on Gamma Delta’s core values. She read aloud, “The five core values of Gamma Delta are Service, Integrity, Growth, Unity, and Leadership. Each value guides the actions, traditions and expectations for every Gamma Delta.”
The boys saw that each value was accompanied by a section on its importance and application. Every value also had a corresponding set of reflection questions, which, Madison explained seriously, they would answer in writing and turn in by next Monday. The feminized college boys seemed to deflate as their workload grew, and they looked adorably restless. Before moving on, Madison said firmly, “Take your responses seriously.” She warned. “You’ll need to put real thought into your answers, because points will be at stake.” The boys exchanged more uneasy glances.
Cassidy then spoke, “Our traditions are so very important.” She continued gaily, “In your study guides, you’ll learn all about the symbolism behind our colors—rose pink and silver. You’ll understand why our official flower, the cream-colored rose, embodies the Gamma Delta spirit. You’ll also find in your handouts the lyrics for our official hymn, ‘The Shining Eyes of Gamma Delta.’”
Fumbling in his booklet, Nate found the page detailing the sorority’s song, complete with annotated sheet music and suggested choreography.
“I highly suggest you begin memorizing the words right away,” Cassidy advised them. Then she added with a wink, “But don’t worry, you’ll be singing it by next Thursday.”
Nate practically winced as he scanned the extensive performance notes.
When the hour reached eight, Madison cheerfully announced that it was time for the boys to get their first lesson in the history and lore of Gamma Delta. Most of the other Sisters in the room turned their chairs to watch. Madison then produced a neat stack of study packets. The booklet covers were stamped with the sorority crest, and she distributed them with the flourish of someone unveiling treasure. Her voice took on an air of ceremony. “Tonight, you’ll begin to appreciate what it means to be part of the Gamma Delta fold. This isn’t just a sorority—it’s a tradition, a legacy, and a family. And as our Little Sisters, the newest members of the Alexionian Society, you are going to learn all about our history, values, and what makes Gamma Delta special.”
The boys exchanged pained looks as their Big Sisters gathered around, ready to guide where needed. Madison’s tone grew even more serious as she continued: “I want you to understand that starting now, you must apply yourselves with the utmost diligence. Mastering all the material in these packets is not optional. You will be expected to know by heart every aspect of Gamma Delta history, tradition, and lore.”
Madison let that sink in, and then she began the lesson, her tone serious. “Let’s start with our motto: ‘Sisterhood in Service and Strength.’ It’s more than words. It’s a promise that every member supports one another and works toward bettering themselves and the community.” She pointed to a banner overhead, where the Greek letters ?? were displayed in elegant gold script. “Gamma Delta—those letters stand for ‘growth and change,’ the twin pillars upon which all our rituals and goals rest.”
Madison then instructed the boys to open their packets to the first section on Gamma Delta’s core values. She read aloud, “The five core values of Gamma Delta are Service, Integrity, Growth, Unity, and Leadership. Each value guides the actions, traditions and expectations for every Gamma Delta.”
The boys saw that each value was accompanied by a section on its importance and application. Every value also had a corresponding set of reflection questions, which, Madison explained seriously, they would answer in writing and turn in by next Monday. The feminized college boys seemed to deflate as their workload grew, and they looked adorably restless. Before moving on, Madison said firmly, “Take your responses seriously.” She warned. “You’ll need to put real thought into your answers, because points will be at stake.” The boys exchanged more uneasy glances.
Cassidy then spoke, “Our traditions are so very important.” She continued gaily, “In your study guides, you’ll learn all about the symbolism behind our colors—rose pink and silver. You’ll understand why our official flower, the cream-colored rose, embodies the Gamma Delta spirit. You’ll also find in your handouts the lyrics for our official hymn, ‘The Shining Eyes of Gamma Delta.’”
Fumbling in his booklet, Nate found the page detailing the sorority’s song, complete with annotated sheet music and suggested choreography.
“I highly suggest you begin memorizing the words right away,” Cassidy advised them. Then she added with a wink, “But don’t worry, you’ll be singing it by next Thursday.”
Nate practically winced as he scanned the extensive performance notes.
2
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by BabyJay on Yesterday at 09:13:34 AM »
Looks like the 'Little girls' are becoming more resigned to their new roles. At least the 'Big Girls' of Gamma delta have confined themselves to only mild teasing and seem happy to assist them in their studies. Wonder how long it will last?
3
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on Yesterday at 07:11:01 AM »
Study Hall
As they entered the study lounge, they saw some of the Sisters were already there to begin work on their own studies. The air was still charged with excitement following the drama of the ceremony a few minutes before. Madison quietly announced to the room, “Our new Little Sisters will be joining us for their first study hall this evening.” The boys filed in, their movements careful and almost fragile as they clutched the unfamiliar folds of their navy skirts. Their nerves were still raw from the ordeal downstairs and as they entered the boys were enveloped by a scene that practically sparkled with feminine energy.
There was another soft ripple of laughter and some delighted murmurs from the sisters scattered at nearby tables. One girl noted again, “They look so cute, and those skirts are just everything!” Another chimed in, “Absolutely precious! Just look at those fresh faces.” They were all clearly still amused by the spectacle of these new Little Sisters.
Unsettled and embarrassed, the boys blushed under the collective gaze. Their clingy tights and delicate blouses made them feel so feminine and exposed. They cringed in embarrassment. They had so many questions, but they were afraid to speak. They knew it was time to hit the books.
Soon, the Gamma Delta study lounge buzzed with gentle energy as all the sisters resumed their own work. The walls were hung with photographs—groups of sisters posing happily, celebrating victories and offering silent proof of the sorority’s spirit of camaraderie. The boys found their places at a large round table. With their notebooks and textbooks arranged before them, they tried to study. Their darling clothes and the subtle fragrances of powder and lip gloss kept their senses on edge.
Madison told them quietly, “Our study hall isn’t just about homework. It’s about supporting each other, asking questions, and learning together. Gamma Deltas always help their Little Sisters succeed.”
The boys shared a collective grimace but tried to tackle their homework. Dressed as they were and still unsettled by the shock of the ceremony, they found it nearly impossible to concentrate.
Nate found himself tugging discreetly at the edge of his navy skirt, hyper-aware of how his tights hugged his legs. Several times, Tara had to tell Milo to stop fidgeting with the collar of his airy blouse which earned him embarrassing glances from the assembled sisters. Julian restlessly shuffled his ballet flats against the carpet. Owen sat more rigidly. He was acutely aware of his delicate makeup and feminine clothes, and his discomfort was obvious.
As the Big Sisters tackled their own coursework, they occasionally floated from seat to seat and offered help with tricky math problems or essay outlines, perfume swirling in the air. Between whispered hints and sweet giggles, the Big Sisters found countless little excuses to dote on their new charges.
During the course of study hall, the Big Sisters made sure each boy got to experience a quick “lip gloss refresh.” Periodically, Madison would quietly tap a shoulder and gesture to a Big Sister, and the selected boy would be gently but insistently escorted to a pastel ottoman in the far corner. It was placed in a spot painstakingly chosen to ensure maximum visibility from across the lounge. Each boy was then instructed to sit with his knees pressed together and hands folded daintily in his lap. During these little moments, each boy blushed brightly as his Big Sister smoothed another shimmering layer of gloss onto his lips under the cringing gaze of his peers and all the other Sisters. Sometimes, the Big Sister would tease by pausing dramatically, holding the boy’s chin with gentle fingers and tilting his face so everyone could watch his transformation. The ritual left them squirming in embarrassment, their lips shiny and sweetly scented.
Despite it all, the boys began to relax slightly, and they were somewhat surprised to find that the Big Sisters seemed genuinely interested in their academic progress.
As they entered the study lounge, they saw some of the Sisters were already there to begin work on their own studies. The air was still charged with excitement following the drama of the ceremony a few minutes before. Madison quietly announced to the room, “Our new Little Sisters will be joining us for their first study hall this evening.” The boys filed in, their movements careful and almost fragile as they clutched the unfamiliar folds of their navy skirts. Their nerves were still raw from the ordeal downstairs and as they entered the boys were enveloped by a scene that practically sparkled with feminine energy.
There was another soft ripple of laughter and some delighted murmurs from the sisters scattered at nearby tables. One girl noted again, “They look so cute, and those skirts are just everything!” Another chimed in, “Absolutely precious! Just look at those fresh faces.” They were all clearly still amused by the spectacle of these new Little Sisters.
Unsettled and embarrassed, the boys blushed under the collective gaze. Their clingy tights and delicate blouses made them feel so feminine and exposed. They cringed in embarrassment. They had so many questions, but they were afraid to speak. They knew it was time to hit the books.
Soon, the Gamma Delta study lounge buzzed with gentle energy as all the sisters resumed their own work. The walls were hung with photographs—groups of sisters posing happily, celebrating victories and offering silent proof of the sorority’s spirit of camaraderie. The boys found their places at a large round table. With their notebooks and textbooks arranged before them, they tried to study. Their darling clothes and the subtle fragrances of powder and lip gloss kept their senses on edge.
Madison told them quietly, “Our study hall isn’t just about homework. It’s about supporting each other, asking questions, and learning together. Gamma Deltas always help their Little Sisters succeed.”
The boys shared a collective grimace but tried to tackle their homework. Dressed as they were and still unsettled by the shock of the ceremony, they found it nearly impossible to concentrate.
Nate found himself tugging discreetly at the edge of his navy skirt, hyper-aware of how his tights hugged his legs. Several times, Tara had to tell Milo to stop fidgeting with the collar of his airy blouse which earned him embarrassing glances from the assembled sisters. Julian restlessly shuffled his ballet flats against the carpet. Owen sat more rigidly. He was acutely aware of his delicate makeup and feminine clothes, and his discomfort was obvious.
As the Big Sisters tackled their own coursework, they occasionally floated from seat to seat and offered help with tricky math problems or essay outlines, perfume swirling in the air. Between whispered hints and sweet giggles, the Big Sisters found countless little excuses to dote on their new charges.
During the course of study hall, the Big Sisters made sure each boy got to experience a quick “lip gloss refresh.” Periodically, Madison would quietly tap a shoulder and gesture to a Big Sister, and the selected boy would be gently but insistently escorted to a pastel ottoman in the far corner. It was placed in a spot painstakingly chosen to ensure maximum visibility from across the lounge. Each boy was then instructed to sit with his knees pressed together and hands folded daintily in his lap. During these little moments, each boy blushed brightly as his Big Sister smoothed another shimmering layer of gloss onto his lips under the cringing gaze of his peers and all the other Sisters. Sometimes, the Big Sister would tease by pausing dramatically, holding the boy’s chin with gentle fingers and tilting his face so everyone could watch his transformation. The ritual left them squirming in embarrassment, their lips shiny and sweetly scented.
Despite it all, the boys began to relax slightly, and they were somewhat surprised to find that the Big Sisters seemed genuinely interested in their academic progress.
4
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by BabyJay on November 11, 2025, 04:00:31 PM »
Delightful. Now that the 4 'Little Sisters' have ben inducted into the newly resurrected Alexionian Society will they now be deemed to be the new 'Handmaidens' of the 'Big Sisters' of Gamma Delta and pander to their every wish and command? Will they also have a new dress code?
5
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by babycakes on November 11, 2025, 03:16:33 PM »
Talk about "out of the frying pan, into the fire"! Wonder when they'll realize they pledged unending (?) servitude/slavery (with fur lined shackles) to their big sisters? Of course the sisters are excited. They haven't had male maids in four years.
6
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 11, 2025, 11:43:11 AM »
Chapter 272.
They all wanted photos or little videos, demanding smiles, peace signs, and pretty much every sort of humiliating pose they could think of. Serena largely just looked on, encouraging the other three with suggestions or little humorous quips. Margaret was the worst, stepping forward every now and then to adjust his dress, to puff the sleeves more, hitch up the skirt, or check his bra or stockings - any excuse to paw him. His face was burning – this was so different from yesterday. He no longer felt admired, only humiliated. Serena was fully aware of his discomfiture, but quite without sympathy.
“Do you find this difficult, Tim? I’m afraid if you aspire to become a ladies’ maid, you’re going to have to get used to it. Being the centre of attention is not always as pleasant as you might have thought.”
“Well, Ser…I mean, miss… I don’t achally wanna be a maid, see? I didn’t sign up for this…”
“Didn’t sign up for it? Oh, but you did! That’s exactly what you did. Read your contract. It covers any employment at the discretion of the employer – in this case, Miss Poole.”
Tim looked at her in dismay. Yesterday she’d seemed so warm and friendly. Today…
“Okay, let me explain what’s going to happen, and why. My mum is involved in a range of businesses. One of them, in which your employer also has a major interest, is a domestic maid agency specialising in boy maids. They’re good looking, nicely dressed and well-trained, polite and obedient. Obedience and submissiveness is the key, the sine qua non. Well-off ladies will pay a high price such domestics. You’re going to be trained to be one such. No, no…don’t make a face. If Miss Poole were to see that reaction…”
Tim wilted. “Please don’t tell her…”
“So behave yourself! You will be trained, you will become the best, you will serve diligently. Understood?”
Tim nodded meekly.
“You’ll be a boot boy on weekdays, and a maid at weekends. You will be trained until you are of sufficient proficiency to be placed. I wouldn’t be too downcast, Timothy. You will receive a percentage of the hourly rate which will be more than double what you are being paid as a boot boy.”
Tim perked up at this revelation.
“Really, miss?”
“Of course. Maiding is far more skilled work than polishing boots – don’t you agree? You will get paid accordingly. But equally, poor performance, even minor errors of etiquette, will be punished severely, during training and at work. Your mistresses will be empowered to apply any form of punishment or discipline they think fit. Understand?”
“Yes, miss…”
“Good. Serious training will begin next week. Today you may practise serving drinks and learning to be silent and invisible when you’re not needed – which won’t be very often, by the way. I can't pretend it won't be hard work.” There was the sound of steps coming down the stairs “Oh, I think I hear Terry coming downstairs. That’s Teri with and “i” by the way. Boy maids are always given girls’ names, and addressed as females. We’ll decide your later. Yes, here she is. Teri, meet Timothy. You may both come into the living-room. We’ll leave you alone for thirty minutes or so to get to know each other. Okay Nicola?”
“Sure, Serena. Teri, fill Timothy in about what’ll be expected of him, all right?”
“Yes, miss Nicola.” He turned to Tim. “Hi, Timothy…”
“Hi…er, Teri…”
Teri was about his age, shortish blond hair, friendly face. Tim took a liking to him at once.
“I like your outfit,” said Teri. “I wanted a pink one, but my mistress insisted on blue – said it goes with my hair…”
“It suits you… You look great…”
“Thanks. We should have a chat.”
“Yeah, could we? I ‘ad no idea what was gonna ‘appen when I came ‘ere. I’m still, like, in shock…”
“You’ll be okay. You’re good looking. You’ll be in demand. I can see that already.”
“I ain’t sure…”
“It isn’t that bad. The money’s great. I’m full-time. Nicola’s my permanent mistress, though I get placed too, sometimes for days at a time. But Nicola’s very good to me…”
“That’s nice…”
“Yeah. But it’s hit and miss when you’re sent out. Some of those ‘ladies’ so-called…”
“Can we…go outside for a minute?”
“Miss… May we go into the garden for a few minutes?”
“Yes. Be back by ten.”
“Yes miss. Thank you miss.”
“Thank you, miss,” added Tim, politely. He was already learning…
They all wanted photos or little videos, demanding smiles, peace signs, and pretty much every sort of humiliating pose they could think of. Serena largely just looked on, encouraging the other three with suggestions or little humorous quips. Margaret was the worst, stepping forward every now and then to adjust his dress, to puff the sleeves more, hitch up the skirt, or check his bra or stockings - any excuse to paw him. His face was burning – this was so different from yesterday. He no longer felt admired, only humiliated. Serena was fully aware of his discomfiture, but quite without sympathy.
“Do you find this difficult, Tim? I’m afraid if you aspire to become a ladies’ maid, you’re going to have to get used to it. Being the centre of attention is not always as pleasant as you might have thought.”
“Well, Ser…I mean, miss… I don’t achally wanna be a maid, see? I didn’t sign up for this…”
“Didn’t sign up for it? Oh, but you did! That’s exactly what you did. Read your contract. It covers any employment at the discretion of the employer – in this case, Miss Poole.”
Tim looked at her in dismay. Yesterday she’d seemed so warm and friendly. Today…
“Okay, let me explain what’s going to happen, and why. My mum is involved in a range of businesses. One of them, in which your employer also has a major interest, is a domestic maid agency specialising in boy maids. They’re good looking, nicely dressed and well-trained, polite and obedient. Obedience and submissiveness is the key, the sine qua non. Well-off ladies will pay a high price such domestics. You’re going to be trained to be one such. No, no…don’t make a face. If Miss Poole were to see that reaction…”
Tim wilted. “Please don’t tell her…”
“So behave yourself! You will be trained, you will become the best, you will serve diligently. Understood?”
Tim nodded meekly.
“You’ll be a boot boy on weekdays, and a maid at weekends. You will be trained until you are of sufficient proficiency to be placed. I wouldn’t be too downcast, Timothy. You will receive a percentage of the hourly rate which will be more than double what you are being paid as a boot boy.”
Tim perked up at this revelation.
“Really, miss?”
“Of course. Maiding is far more skilled work than polishing boots – don’t you agree? You will get paid accordingly. But equally, poor performance, even minor errors of etiquette, will be punished severely, during training and at work. Your mistresses will be empowered to apply any form of punishment or discipline they think fit. Understand?”
“Yes, miss…”
“Good. Serious training will begin next week. Today you may practise serving drinks and learning to be silent and invisible when you’re not needed – which won’t be very often, by the way. I can't pretend it won't be hard work.” There was the sound of steps coming down the stairs “Oh, I think I hear Terry coming downstairs. That’s Teri with and “i” by the way. Boy maids are always given girls’ names, and addressed as females. We’ll decide your later. Yes, here she is. Teri, meet Timothy. You may both come into the living-room. We’ll leave you alone for thirty minutes or so to get to know each other. Okay Nicola?”
“Sure, Serena. Teri, fill Timothy in about what’ll be expected of him, all right?”
“Yes, miss Nicola.” He turned to Tim. “Hi, Timothy…”
“Hi…er, Teri…”
Teri was about his age, shortish blond hair, friendly face. Tim took a liking to him at once.
“I like your outfit,” said Teri. “I wanted a pink one, but my mistress insisted on blue – said it goes with my hair…”
“It suits you… You look great…”
“Thanks. We should have a chat.”
“Yeah, could we? I ‘ad no idea what was gonna ‘appen when I came ‘ere. I’m still, like, in shock…”
“You’ll be okay. You’re good looking. You’ll be in demand. I can see that already.”
“I ain’t sure…”
“It isn’t that bad. The money’s great. I’m full-time. Nicola’s my permanent mistress, though I get placed too, sometimes for days at a time. But Nicola’s very good to me…”
“That’s nice…”
“Yeah. But it’s hit and miss when you’re sent out. Some of those ‘ladies’ so-called…”
“Can we…go outside for a minute?”
“Miss… May we go into the garden for a few minutes?”
“Yes. Be back by ten.”
“Yes miss. Thank you miss.”
“Thank you, miss,” added Tim, politely. He was already learning…
7
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, ands 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, ands 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…
8
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 midday Mélisande stopped for lunch. 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. She turned him back the way they had come, gave him a kick and two good firm smacks with her whip, and 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! Did you change 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 midday Mélisande stopped for lunch. 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. She turned him back the way they had come, gave him a kick and two good firm smacks with her whip, and 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! Did you change 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.”
9
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.”
10
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.
The more you give, the more I can give back.
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