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Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 21, 2026, 08:35:33 AM »
Chapter 321.
The top half of Clara, Maggie, and a ginger-haired boy were seen through the window. The whole class turned to stare. Madeline stood up to get a better view.
“Madeline! Sit down!”
The classroom door opened slowly. The girls grinning faces appeared. They advanced backwards into the room, each of them tugging at a hand belonging to the apparently reluctant trainee maid – whose hands were sheathed in a pair of glossy red latex gloves! The students gaped. Miss Taylor, who had a better view from her position at the teacher’s desk, smiled despite herself and covered her mouth with her hand. With a final concerted heave, they tumbled Tim into the room. Clara quickly let go of his hand, gave him a push, and slammed the door behind him. He stood there, like a rabbit in the headlights, regarding the rows of astonished faces with wide-eyed alarm. The was a brief pause, then the whole class gasped as one. Whatever they were expecting, the reality was beyond their wildest speculation. Clara stepped forward.
“Please welcome Tim. Tim is training to be a lady’s maid. He is multi-talented. He is also a professional boot boy at Pitt’s Wood Equestrian Centre.”
Maggie had taken a little stool from the corner and placed it in front of the blackboard.
“Tim? Come and stand up here, please, so that the class can see you.”
Tim was helpless with fright. Clara led him over and helped him up, amidst whispers, titters, and the occasional snort of suppressed laughter.
“Face the class, please, Tim…”
Miss Taylor walked over and took his hand, determined to make him feel at ease.
“Thank you so much for coming, Tim. It’s wonderful to have you for our show and share. We’re especially grateful since it sounds as though you have a very busy life at the moment. Girls, I think Tim deserves a round of applause.”
The girls responded loudly, not only clapping but cheering and whistling. Tim still looked nervous, but gratified as well.
“Well I’ll hand you over to Clara and Maggie, as you’re their personal project.”
“Thank you, Miss Taylor,” smiled Clara. She turned to face the class.
“Tim left school in the summer, having passed all his exams, and having earned a place at uni. That’s right, Tim?”
He nodded modestly.
“So he could have gone straight up and continued his studies. But instead he decided that he wanted to do some useful work. So together with his friend Bobby he volunteered to work at Pitt’s Wood, keeping all the stable girls’ boots nice and clean and shiny, and servicing customers from the neighbouring area to earn extra income to help run the Centre and feed all the horses. In return the Centre looked after him and Bobby and had lovely uniforms made for them.” She turned to Tim. “Tim? Could you give me that envelope I asked you to put in your bag?”
“Oh…y-yes… Here, Miss Clara…”
She slipped out three photographs of Tim and Bobby in their boot boy outfits, two of them showing them at work, on their knees, and gave them to Madeline.
“Here, Madeline, could you pass them round, please?”
As they circulated there were giggles of delight. Madeline looked straight at Tim.
“Can I and my friends come and get our boots polished by you and your friend?”
“Y-yes, miss…of course…”
“And you’ll have to kneel down like this and do it?”
“Y-yes…”
“Cool!”
“But he enjoyed working for all those girls and ladies so much,” continued Clara, “that…”
Here she stood aside, and let Maggie take up the story.
“…that he thought he would like to dedicate himself to waiting on all a woman’s needs – by becoming a maid! So he went into training. Washing, cleaning, waiting, cooking, serving in every conceivable way, keeping his mistress happy and contented. In a couple of weeks he should have been trained to a satisfactory standard, and then he will be put into full-time domestic service. Clara? Could we have the photos of Tim in his maid’s outfit?”
“I’ll pass them round….”
“Oh my god,” exclaimed Madeline. “All his outfits are latex, right? Wow, that’s super sexy!”
“Madeline!” snapped Miss Taylor.
“No, miss, I didn’t mean anything bad. He looks great. He’s really good looking, he's got great legs, and the uniform's so cute...”
“Thank you, Madeline. We all value your opinions, but that’s enough for now…” said Miss Taylor. But glancing at Tim, she could see he was quite pleased. He did a sort of little static swagger on the stool. She made a mental note to ask Clara if she could keep the photos to put up on the notice-board. And maybe a couple for herself…
The top half of Clara, Maggie, and a ginger-haired boy were seen through the window. The whole class turned to stare. Madeline stood up to get a better view.
“Madeline! Sit down!”
The classroom door opened slowly. The girls grinning faces appeared. They advanced backwards into the room, each of them tugging at a hand belonging to the apparently reluctant trainee maid – whose hands were sheathed in a pair of glossy red latex gloves! The students gaped. Miss Taylor, who had a better view from her position at the teacher’s desk, smiled despite herself and covered her mouth with her hand. With a final concerted heave, they tumbled Tim into the room. Clara quickly let go of his hand, gave him a push, and slammed the door behind him. He stood there, like a rabbit in the headlights, regarding the rows of astonished faces with wide-eyed alarm. The was a brief pause, then the whole class gasped as one. Whatever they were expecting, the reality was beyond their wildest speculation. Clara stepped forward.
“Please welcome Tim. Tim is training to be a lady’s maid. He is multi-talented. He is also a professional boot boy at Pitt’s Wood Equestrian Centre.”
Maggie had taken a little stool from the corner and placed it in front of the blackboard.
“Tim? Come and stand up here, please, so that the class can see you.”
Tim was helpless with fright. Clara led him over and helped him up, amidst whispers, titters, and the occasional snort of suppressed laughter.
“Face the class, please, Tim…”
Miss Taylor walked over and took his hand, determined to make him feel at ease.
“Thank you so much for coming, Tim. It’s wonderful to have you for our show and share. We’re especially grateful since it sounds as though you have a very busy life at the moment. Girls, I think Tim deserves a round of applause.”
The girls responded loudly, not only clapping but cheering and whistling. Tim still looked nervous, but gratified as well.
“Well I’ll hand you over to Clara and Maggie, as you’re their personal project.”
“Thank you, Miss Taylor,” smiled Clara. She turned to face the class.
“Tim left school in the summer, having passed all his exams, and having earned a place at uni. That’s right, Tim?”
He nodded modestly.
“So he could have gone straight up and continued his studies. But instead he decided that he wanted to do some useful work. So together with his friend Bobby he volunteered to work at Pitt’s Wood, keeping all the stable girls’ boots nice and clean and shiny, and servicing customers from the neighbouring area to earn extra income to help run the Centre and feed all the horses. In return the Centre looked after him and Bobby and had lovely uniforms made for them.” She turned to Tim. “Tim? Could you give me that envelope I asked you to put in your bag?”
“Oh…y-yes… Here, Miss Clara…”
She slipped out three photographs of Tim and Bobby in their boot boy outfits, two of them showing them at work, on their knees, and gave them to Madeline.
“Here, Madeline, could you pass them round, please?”
As they circulated there were giggles of delight. Madeline looked straight at Tim.
“Can I and my friends come and get our boots polished by you and your friend?”
“Y-yes, miss…of course…”
“And you’ll have to kneel down like this and do it?”
“Y-yes…”
“Cool!”
“But he enjoyed working for all those girls and ladies so much,” continued Clara, “that…”
Here she stood aside, and let Maggie take up the story.
“…that he thought he would like to dedicate himself to waiting on all a woman’s needs – by becoming a maid! So he went into training. Washing, cleaning, waiting, cooking, serving in every conceivable way, keeping his mistress happy and contented. In a couple of weeks he should have been trained to a satisfactory standard, and then he will be put into full-time domestic service. Clara? Could we have the photos of Tim in his maid’s outfit?”
“I’ll pass them round….”
“Oh my god,” exclaimed Madeline. “All his outfits are latex, right? Wow, that’s super sexy!”
“Madeline!” snapped Miss Taylor.
“No, miss, I didn’t mean anything bad. He looks great. He’s really good looking, he's got great legs, and the uniform's so cute...”
“Thank you, Madeline. We all value your opinions, but that’s enough for now…” said Miss Taylor. But glancing at Tim, she could see he was quite pleased. He did a sort of little static swagger on the stool. She made a mental note to ask Clara if she could keep the photos to put up on the notice-board. And maybe a couple for herself…
2
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 21, 2026, 08:26:13 AM »
Chapter 320.
It was just as well he had agreed, because they had already decided he was going whether he wanted to or not, and the arrangements had already been made. Clara had called Sasha to get the low down on his history, plus a few piccies, and the girls had spoken to Miss Taylor that morning. She had snorted with laughter when she saw a picture of the boy they wanted to show and share.
“Miss…no. You mustn’t laugh,” said Clara, with mock dismay. “Tim’s quite vain, and you’ll hurt his feelings.”
“That’s right,” added Maggie, with a wink. “He thinks he’s super cute, and we want to keep it that way. Anyway, this costume’s just temporary. He’s training to be a lady’s maid.”
“A what?”
“Yes, miss,” said Clara, “a proper maid. He has a special pink latex uniform and he’s desperate to wear it again and get to work. Isn’t it sweet? My mum’s helping train him. He’s only staying with us till Sunday, then he goes back to training school.”
And she gave Miss Taylor a brief resumé of Tim’s training and what she had understood about the reason he’d been allocated his current outfit.
“Well, well. I must say this is more like it. This will make the class sit up and take notice. I’ll have to warn them not to start screaming with laughter.”
“Yes, please do that,” said Clara. “We’ll aim to arrive about fifteen minutes after the start of afternoon school, so you’ll have time to explain.”
“Perfect! Well, girls. It looks like being a fun afternoon!”
Miss Taylor was as good as her word. Once the class had settled after lunch, she called for quiet.
“Now girls, listen carefully. I have something to tell you. I hope you’ve all had a good chatter and a laugh at lunchtime, because you’re going to have to curb your natural exuberance for a while. Let me explain. Clara and Maggie have booked their show and share for this double lesson.”
“What are they going to show, miss?” asked a dark-haired girl in the front row. (She was in the front row for a reason, and not by choice.)
“If you’ll allow me, Madeline, I’ll tell you. They’re bringing a friend of theirs, a boy called Tim. Now Tim is training to be a maid…”
“A what, miss?”
“Madeline! Silence! Just be quiet and listen. As I said, Tim’s training to be a maid. Yes, boys can be maids too… And yes, I can see you’re all wondering… Yes, eventually, when he qualifies, he’ll wear a proper maid’s uniform, with a little maid’s cap, ands a maid’s dress, and an apron… Everything. Now… Shush, please. Now… Tim’s still in training, and until he passes the basic proficiency tests, he has to wear one of the special, er, trainee outfits…as you will see. Now, listen all of you! Madeline! Behave please.” She sighed. “Now, this is important, so pay attention. Madeline, how old are you?”
“Seventeen, miss.”
“Then stop behaving like a twelve-year-old, would you? As I was saying, please treat Tim with the utmost respect. I understand he’s a sensitive boy – stop smirking, Natalie! - and any negativity could be hurtful. He actually needs a confidence boost, because what he’s trying to do requires a lot of courage. It’s easy nowadays for girls to do jobs that used to be considered as boys’ only. It’s a lot harder for a boy to do what has traditionally been a girl’s job. Good – I’m glad you understand. So I’m relying on you to make him feel relaxed and accepted. Yes? Good girls. I trust you to be welcoming and warm, because I know you’re all mature adults. Then you’ll be able to ask him any questions you want about his training.”
Steps were heard in the corridor.
“Ah, I think this is them now…”
It was just as well he had agreed, because they had already decided he was going whether he wanted to or not, and the arrangements had already been made. Clara had called Sasha to get the low down on his history, plus a few piccies, and the girls had spoken to Miss Taylor that morning. She had snorted with laughter when she saw a picture of the boy they wanted to show and share.
“Miss…no. You mustn’t laugh,” said Clara, with mock dismay. “Tim’s quite vain, and you’ll hurt his feelings.”
“That’s right,” added Maggie, with a wink. “He thinks he’s super cute, and we want to keep it that way. Anyway, this costume’s just temporary. He’s training to be a lady’s maid.”
“A what?”
“Yes, miss,” said Clara, “a proper maid. He has a special pink latex uniform and he’s desperate to wear it again and get to work. Isn’t it sweet? My mum’s helping train him. He’s only staying with us till Sunday, then he goes back to training school.”
And she gave Miss Taylor a brief resumé of Tim’s training and what she had understood about the reason he’d been allocated his current outfit.
“Well, well. I must say this is more like it. This will make the class sit up and take notice. I’ll have to warn them not to start screaming with laughter.”
“Yes, please do that,” said Clara. “We’ll aim to arrive about fifteen minutes after the start of afternoon school, so you’ll have time to explain.”
“Perfect! Well, girls. It looks like being a fun afternoon!”
Miss Taylor was as good as her word. Once the class had settled after lunch, she called for quiet.
“Now girls, listen carefully. I have something to tell you. I hope you’ve all had a good chatter and a laugh at lunchtime, because you’re going to have to curb your natural exuberance for a while. Let me explain. Clara and Maggie have booked their show and share for this double lesson.”
“What are they going to show, miss?” asked a dark-haired girl in the front row. (She was in the front row for a reason, and not by choice.)
“If you’ll allow me, Madeline, I’ll tell you. They’re bringing a friend of theirs, a boy called Tim. Now Tim is training to be a maid…”
“A what, miss?”
“Madeline! Silence! Just be quiet and listen. As I said, Tim’s training to be a maid. Yes, boys can be maids too… And yes, I can see you’re all wondering… Yes, eventually, when he qualifies, he’ll wear a proper maid’s uniform, with a little maid’s cap, ands a maid’s dress, and an apron… Everything. Now… Shush, please. Now… Tim’s still in training, and until he passes the basic proficiency tests, he has to wear one of the special, er, trainee outfits…as you will see. Now, listen all of you! Madeline! Behave please.” She sighed. “Now, this is important, so pay attention. Madeline, how old are you?”
“Seventeen, miss.”
“Then stop behaving like a twelve-year-old, would you? As I was saying, please treat Tim with the utmost respect. I understand he’s a sensitive boy – stop smirking, Natalie! - and any negativity could be hurtful. He actually needs a confidence boost, because what he’s trying to do requires a lot of courage. It’s easy nowadays for girls to do jobs that used to be considered as boys’ only. It’s a lot harder for a boy to do what has traditionally been a girl’s job. Good – I’m glad you understand. So I’m relying on you to make him feel relaxed and accepted. Yes? Good girls. I trust you to be welcoming and warm, because I know you’re all mature adults. Then you’ll be able to ask him any questions you want about his training.”
Steps were heard in the corridor.
“Ah, I think this is them now…”
3
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 21, 2026, 08:22:00 AM »
Chapter 319.
He got on with his chores. It was a good feeling, doing his maid duties all by himself, as Shirley had taught him. He felt responsible and trusted. He forgot all about his new outfit until he heard the front door being unlocked. The girls were home for lunch! Maybe they’d laugh at him…
But to his surprise they had the opposite reaction. They trooped through to the kitchen chattering away, but stopped dead when they caught sight of him. He was already colouring up again, when Maggie gasped.
“Tim! You look amazing! I love the new top! And the bag…”
“Wow! Cool!” cried Clara. “Look at this bag, Maggie. I bet that cost a bit… And the matching gloves and boots! I want them! Tim, lend them to me sometime, would you? Maybe Saturday night? We going clubbing down the village. They would be perfect!”
Tim was taken aback, but gratified.
“W-well, of course, Clara. I’m glad you like them. They are quite swish, ain’t – I mean aren’t – they?”
“Very!”
In his innocence he had no suspicion that the girls might have been forewarned. Nor that they had an ulterior motive for their approbation.
“Oh, and you’ve made our lunch! Look Clara, sandwiches – tuna mayo and egg mayo – a salad – looks as good as your mum’s! Drinks and fruit and chocolate bars. Thanks, Tim!”
“Yeah. Come on, Maggie, let’s eat. Tim, come join us. Come on, sit down. You’re not a maid yet.”
“But maybe when you are…” began Maggie.
“Yes. We were talking. When you’re fully qualified and everything, I want mum to employ you. We could have such fun. What do you think?”
“Yeah, great! Would you really do that?”
“Course. And you wouldn’t have to be working all the time. We could be good friends, eh, Maggie?”
“Sure. It’d be great to have a guy around. We spend all our days with a bunch of girls. Imagine… How would you like it if you saw nothing but females all day long…?”
Tim didn’t reply, but looked wistful. Clara suddenly put down her sandwich and sat bolt upright.
“I’ve had a great idea! We have Miss Taylor first two periods, don’t we Maggie? And we’re the only ones who haven’t done show and share this weekend. Why don’t we…?”
“Tim? fuc-k, yeah! He’d be perfect!”
“What? What’s that?” asked Tim, frowning.
“Right, I’ll explain,” said Clara. There are twenty girls in our class, and we’re all paired up – so there’s me and Maggie, fr’instance. Every term each pair gets to do a show and share – you know, they bring in something to show and tell the class about. It’s so boring! The last pair brought in an odd-shaped stone! Can you believe it? But Miss Taylor likes us and as its free periods today she’d definitely let us do it. Would you be our show and share? Please say you would…”
“Yes… Please, Tim…”
Tim was slightly taken aback. It was definitely scary. But the girls were looking at him pleadingly, and the last thing he wanted was to disappoint them, especially as they wanted to be friends, and in any case Shirley had told him to go along with anything they asked. And maybe, just maybe, he’d be as big a hit with the rest of the class… All these thoughts crossed his mind in a couple of seconds. He had to answer quickly, or he’d look churlish…
“Sure,” he blurted. And was immediately pounced on by the delighted girls. Clara even gave him a kiss on the cheek, which reassured him he’d made the right decision…
He got on with his chores. It was a good feeling, doing his maid duties all by himself, as Shirley had taught him. He felt responsible and trusted. He forgot all about his new outfit until he heard the front door being unlocked. The girls were home for lunch! Maybe they’d laugh at him…
But to his surprise they had the opposite reaction. They trooped through to the kitchen chattering away, but stopped dead when they caught sight of him. He was already colouring up again, when Maggie gasped.
“Tim! You look amazing! I love the new top! And the bag…”
“Wow! Cool!” cried Clara. “Look at this bag, Maggie. I bet that cost a bit… And the matching gloves and boots! I want them! Tim, lend them to me sometime, would you? Maybe Saturday night? We going clubbing down the village. They would be perfect!”
Tim was taken aback, but gratified.
“W-well, of course, Clara. I’m glad you like them. They are quite swish, ain’t – I mean aren’t – they?”
“Very!”
In his innocence he had no suspicion that the girls might have been forewarned. Nor that they had an ulterior motive for their approbation.
“Oh, and you’ve made our lunch! Look Clara, sandwiches – tuna mayo and egg mayo – a salad – looks as good as your mum’s! Drinks and fruit and chocolate bars. Thanks, Tim!”
“Yeah. Come on, Maggie, let’s eat. Tim, come join us. Come on, sit down. You’re not a maid yet.”
“But maybe when you are…” began Maggie.
“Yes. We were talking. When you’re fully qualified and everything, I want mum to employ you. We could have such fun. What do you think?”
“Yeah, great! Would you really do that?”
“Course. And you wouldn’t have to be working all the time. We could be good friends, eh, Maggie?”
“Sure. It’d be great to have a guy around. We spend all our days with a bunch of girls. Imagine… How would you like it if you saw nothing but females all day long…?”
Tim didn’t reply, but looked wistful. Clara suddenly put down her sandwich and sat bolt upright.
“I’ve had a great idea! We have Miss Taylor first two periods, don’t we Maggie? And we’re the only ones who haven’t done show and share this weekend. Why don’t we…?”
“Tim? fuc-k, yeah! He’d be perfect!”
“What? What’s that?” asked Tim, frowning.
“Right, I’ll explain,” said Clara. There are twenty girls in our class, and we’re all paired up – so there’s me and Maggie, fr’instance. Every term each pair gets to do a show and share – you know, they bring in something to show and tell the class about. It’s so boring! The last pair brought in an odd-shaped stone! Can you believe it? But Miss Taylor likes us and as its free periods today she’d definitely let us do it. Would you be our show and share? Please say you would…”
“Yes… Please, Tim…”
Tim was slightly taken aback. It was definitely scary. But the girls were looking at him pleadingly, and the last thing he wanted was to disappoint them, especially as they wanted to be friends, and in any case Shirley had told him to go along with anything they asked. And maybe, just maybe, he’d be as big a hit with the rest of the class… All these thoughts crossed his mind in a couple of seconds. He had to answer quickly, or he’d look churlish…
“Sure,” he blurted. And was immediately pounced on by the delighted girls. Clara even gave him a kiss on the cheek, which reassured him he’d made the right decision…
4
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 21, 2026, 08:15:13 AM »
Chapter 318.
ESDS divided their trainees into two streams, junior and senior. The juniors – the likes of Darren and Philip – were selected on the basis of cuteness and willingness. They received a narrow training. Their function would be, principally, to skip around looking pretty, flicking furniture with their little feather dusters, opening doors, taking coats at parties, running simple errands, and so on. They were little decorations, like tinsel on a Christmas tree, intended to do little more than provide a talking point for their mistresses and their friends – talk which often didn’t progress much past “ooh, isn’t he sweet…” or “where did you get him? I want one of those…” They had the gentlest of trainings, were rented out only to the kindest of mistresses, and in general revelled in the pretty outfits and the attention. Some of them enjoyed themselves so much, that as they grew older they wanted to be taught all the appropriate skills, and to progress into the senior stream – which of course they were encouraged to do. The seniors had a much more rigorous training, as Tim was discovering, and there was a significant drop-out rate. The tough ones – Teri was a perfect example – took it in their stride, and became valued and sought-after maids. Teri was professional, but was up for pretty much anything, which made him popular with single women and women who craved male company. In between postings he received “extra training” from Nicola, the nature of which no-one cared to enquire into. The seniors often tended to be fairly streetwise, and knew how to make the most of the perks that came with the job.
So Tim was an exception. A senior based on age, but naïve, ruled by an innocent vanity, a desire to be liked, to elicit attention and praise. From his first entry into The Pitt’s Wood ambit, his mentors had made a point of complimenting him on his appearance, his good looks and his smart uniforms, and fostering his personal pride and exploiting his credulity, making him take people’s attraction, surprise, their smiles and laughter, as compliments, and as a cue to show off all the more. Such flattery also served to tighten their grip on him, so that now it would never even occur to him to question their authority, whether Miss Poole’s or the personnel of ESDS.
So perhaps the transfer to Shirley Foster had been the plan all along. For her, he was ideal material. Her methods could not have been more different from those at headquarters. She didn’t issue orders, but taught him by working with him. She’d do a load of washing, checking the garments with him to see if they needed a separate wash or a particular temperature. She showed him how to iron, letting him take over more and more. They cleaned together and chose cleaning materials, they cooked together, took it in turns to wait on each other or on Clara and Maggie, discussed etiquette, practised curtsies. When Tim did something well, he got a cuddle. Once Shirley would took him on her lap and stroked his hair as if her were a little kid. Another time he got hugs from the girls. She taught him trust, and from trust came confidence. After only a few days, he had lost most of his nervousness, he was relaxed, and he was doing his chores with calm efficiency. On Thursday morning, after he had served breakfast and was clearing the table, and Clara had left for school, he turned to Shirley.
“Miss? Do you think I’m ready to have my maid’s uniform back yet?”
Shirley patted his cheek.
“I’ve already sent in an interim report, Mitzy. Miss Sasha says, providing you complete the week satisfactorily and without incident, she’ll let you have it back at the weekend, and you’ll be allowed to stay till Sunday morning.
“Yippee! Er, I mean, Thank you so much, Miss Shirley…”
“Tim – we should call you Tim until you’re officially a maid again - I’m really enjoying having you here. You’re a pleasure to work with. But this afternoon, I have to go to a meeting, so I’m handing you over to Clara and Maggie for obedience training. You know what that is. You follow their instructions willingly and promptly. You mustn’t question or demur, or you will fail this vital element of the course, which means I’ll have to report it, and you’ll be sent straight back to ESDS as you are. Do you understand what I’m saying?”
“Absolutely, madam,” said Tim, confidently.
“Good. They’ll be back for lunch around twelve, so prepare some sandwiches – you know what they like – and wait on them in the kitchen. When you’ve done the washing up and wiped the table, I’d like you to give their shoes a quick polish. I noticed Clara’s were a bit scruffy when she left this morning. Let me see, anything else… I don’t think so. Okay. I’m going to get ready. You should change as well – put on the outfit Sasha brought. And let me see what you look like with your new shoulder bag and your outside boots. Go on. I’ll be down to check in ten minutes.”
“Yes, miss… Of course…”
When she returned, Shirley threw up her hands in delight.
“My goodness, how smart you look! You’d turn a few heads in the village, and no mistake.”
Tim blushed, and touched his cheeks, which had been burning ever since he’d changed. He wanted to believe she meant that in the best possible way, but he suspected that this outfit, enhanced with accessories Sasha had brought, might possibly attract the wrong sort of attention…
“Surely you’re not shy! From what I’ve heard from Sasha, you love showing off. Aren’t you going to be principal pageboy at a big wedding in a few days?”
“Yes, madam… I’ll have a really cool outfit, too… I’m sorry, I can’t tell you about it…”
“Well, you look pretty cool now, I can tell you.”
“Do I, madam…?” He looked at her doubtfully.
“Yes, you do. Now I have to leave. Have a good day. The girls will have a surprise. They’re going to love your new top. I’ll see you this evening.”
ESDS divided their trainees into two streams, junior and senior. The juniors – the likes of Darren and Philip – were selected on the basis of cuteness and willingness. They received a narrow training. Their function would be, principally, to skip around looking pretty, flicking furniture with their little feather dusters, opening doors, taking coats at parties, running simple errands, and so on. They were little decorations, like tinsel on a Christmas tree, intended to do little more than provide a talking point for their mistresses and their friends – talk which often didn’t progress much past “ooh, isn’t he sweet…” or “where did you get him? I want one of those…” They had the gentlest of trainings, were rented out only to the kindest of mistresses, and in general revelled in the pretty outfits and the attention. Some of them enjoyed themselves so much, that as they grew older they wanted to be taught all the appropriate skills, and to progress into the senior stream – which of course they were encouraged to do. The seniors had a much more rigorous training, as Tim was discovering, and there was a significant drop-out rate. The tough ones – Teri was a perfect example – took it in their stride, and became valued and sought-after maids. Teri was professional, but was up for pretty much anything, which made him popular with single women and women who craved male company. In between postings he received “extra training” from Nicola, the nature of which no-one cared to enquire into. The seniors often tended to be fairly streetwise, and knew how to make the most of the perks that came with the job.
So Tim was an exception. A senior based on age, but naïve, ruled by an innocent vanity, a desire to be liked, to elicit attention and praise. From his first entry into The Pitt’s Wood ambit, his mentors had made a point of complimenting him on his appearance, his good looks and his smart uniforms, and fostering his personal pride and exploiting his credulity, making him take people’s attraction, surprise, their smiles and laughter, as compliments, and as a cue to show off all the more. Such flattery also served to tighten their grip on him, so that now it would never even occur to him to question their authority, whether Miss Poole’s or the personnel of ESDS.
So perhaps the transfer to Shirley Foster had been the plan all along. For her, he was ideal material. Her methods could not have been more different from those at headquarters. She didn’t issue orders, but taught him by working with him. She’d do a load of washing, checking the garments with him to see if they needed a separate wash or a particular temperature. She showed him how to iron, letting him take over more and more. They cleaned together and chose cleaning materials, they cooked together, took it in turns to wait on each other or on Clara and Maggie, discussed etiquette, practised curtsies. When Tim did something well, he got a cuddle. Once Shirley would took him on her lap and stroked his hair as if her were a little kid. Another time he got hugs from the girls. She taught him trust, and from trust came confidence. After only a few days, he had lost most of his nervousness, he was relaxed, and he was doing his chores with calm efficiency. On Thursday morning, after he had served breakfast and was clearing the table, and Clara had left for school, he turned to Shirley.
“Miss? Do you think I’m ready to have my maid’s uniform back yet?”
Shirley patted his cheek.
“I’ve already sent in an interim report, Mitzy. Miss Sasha says, providing you complete the week satisfactorily and without incident, she’ll let you have it back at the weekend, and you’ll be allowed to stay till Sunday morning.
“Yippee! Er, I mean, Thank you so much, Miss Shirley…”
“Tim – we should call you Tim until you’re officially a maid again - I’m really enjoying having you here. You’re a pleasure to work with. But this afternoon, I have to go to a meeting, so I’m handing you over to Clara and Maggie for obedience training. You know what that is. You follow their instructions willingly and promptly. You mustn’t question or demur, or you will fail this vital element of the course, which means I’ll have to report it, and you’ll be sent straight back to ESDS as you are. Do you understand what I’m saying?”
“Absolutely, madam,” said Tim, confidently.
“Good. They’ll be back for lunch around twelve, so prepare some sandwiches – you know what they like – and wait on them in the kitchen. When you’ve done the washing up and wiped the table, I’d like you to give their shoes a quick polish. I noticed Clara’s were a bit scruffy when she left this morning. Let me see, anything else… I don’t think so. Okay. I’m going to get ready. You should change as well – put on the outfit Sasha brought. And let me see what you look like with your new shoulder bag and your outside boots. Go on. I’ll be down to check in ten minutes.”
“Yes, miss… Of course…”
When she returned, Shirley threw up her hands in delight.
“My goodness, how smart you look! You’d turn a few heads in the village, and no mistake.”
Tim blushed, and touched his cheeks, which had been burning ever since he’d changed. He wanted to believe she meant that in the best possible way, but he suspected that this outfit, enhanced with accessories Sasha had brought, might possibly attract the wrong sort of attention…
“Surely you’re not shy! From what I’ve heard from Sasha, you love showing off. Aren’t you going to be principal pageboy at a big wedding in a few days?”
“Yes, madam… I’ll have a really cool outfit, too… I’m sorry, I can’t tell you about it…”
“Well, you look pretty cool now, I can tell you.”
“Do I, madam…?” He looked at her doubtfully.
“Yes, you do. Now I have to leave. Have a good day. The girls will have a surprise. They’re going to love your new top. I’ll see you this evening.”
5
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by BabyJay on January 20, 2026, 09:51:35 AM »
Oh dear! sounds like the 'Little Darlings' are slacking in their homework. Perhaps deducting points is not enough punishment to make them knuckle down. Maybe a more visible sign of punishment is needed.
6
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on January 17, 2026, 11:12:53 AM »
Blunders and Mistakes
Nate was first up and nervously began his presentation. He quickly got a couple of dates confused and omitted key details on his chosen alumna’s roles in the sorority’s traditions. Brianna interrupted him with a sigh, “That’s not accurate, Nate. Did you check your sources?” Then, she added sharply, “You lose two points for lack of accuracy.”
As he continued, he was stopped again. Elise, sounding genuinely disappointed, posed the question, “Did you read anything outside the study booklet, Nate? These women are legends. You owe it to them to get the facts right!” Nate felt so exposed and vulnerable in his pretty tights and delicate blouse as his face turned red. He usually was prepared for his assignments, but they had been flooded with so many things so quickly that he hadn’t put in his normal effort… he hadn’t had time. To his dismay, he became strangely agitated under his confining dancer’s belt and tights as he got more flustered. He muttered a humiliated apology, but the damage was done; another point left the scoreboard. After another couple of minutes and more lost points, Nate’s presentation mercifully ended.
Julian went after Nate. As he was speaking, it was clear from their body language that the Sisters were still unhappy. Julian glanced at Owen helplessly, feeling the pressure mounting as Tara interrupted, “Julian, you’re just reading straight from the booklet. Didn’t you dig up anything new? We expect more than just the basics.” Her tone was sharper now, and several sisters exchanged knowing glances. Julian shuffled his feet nervously, feeling his skirt rustle against his tights.
As the flustered teen continued to stumble through his account of a famous alumna’s leadership, he next was interrupted by Brianna, who raised an eyebrow and asked, “Where did you even get that? That’s not in the notes.” Frustrated, she docked him a point. It would not be his last. He felt his face heat up.
The boys quickly understood their efforts were missing the mark. Each presentation seemed thinner than the last, and the sisters’ polite smiles began to fade, replaced with looks of mild irritation.
Owen was next, and he fared no better. His report was met with stony silence, until Tara finally broke it: “You know, a quick search would have told you so much more. This isn’t what Gamma Delta stands for.” The boys exchanged mortified glances.
Standing red-faced and slightly rattled in his adorable study outfit, he got his notes jumbled up. Elise tapped the table impatiently, “Owen, this is Gamma Delta’s legacy. Where’s the passion? Where are the stories that set our alumnae apart?” The other sissified boys all shifted in their seats as the room grew quieter and more tense.
The sisters grew more demanding, their voices firm and their expressions stern. Madison stood up, folding her arms. “We expect you to care about this. To be part of Gamma Delta, you need to show respect for those who came before.” The boys’ unease grew as the authority in the sisters’ voices made their own shortcomings painfully obvious.
Elise sighed, “Did any of you even try to dig a little deeper? This is your chance to show us you care about Gamma Delta’s legacy. Where are the stories, the interesting facts?” The feminized boys all flushed with embarrassment.
Tara, arms folded, chimed in with a disappointed shake of her head. “You’re supposed to go beyond what’s in your booklets. Did you even look anything up on your own?”
The sisters began docking points with increasing frequency. Milo’s segment on a celebrated Gamma Delta alumna contained only the most basic information, and Cassidy didn’t hesitate to announce, “Minus two for omitting any mention of her extensive scholarship work.”
As their presentations limped to a close, the boys exchanged worried glances, realizing they’d woefully underestimated the task. Tara finally spoke with a disappointed shake of her head, “Next time, we want effort. We want depth. You owe it to the women who built Gamma Delta.”
By the time the Alumna Spotlights were over, the damage was done. The Big Sisters made it clear that next time, they expected research, thoughtful preparation and a genuine appreciation for the traditions and stories that shaped Gamma Delta. The boys’ sorry record of points lost reflected the Sisters’ dissatisfaction. For the first time, they truly understood how easily their hard-earned points could fall away. It was becoming painfully clear that getting to 1000 would be daunting. The Little Darlings all sat meekly in their adorable study outfits and felt a sense of dread at whatever might come next.
Nate was first up and nervously began his presentation. He quickly got a couple of dates confused and omitted key details on his chosen alumna’s roles in the sorority’s traditions. Brianna interrupted him with a sigh, “That’s not accurate, Nate. Did you check your sources?” Then, she added sharply, “You lose two points for lack of accuracy.”
As he continued, he was stopped again. Elise, sounding genuinely disappointed, posed the question, “Did you read anything outside the study booklet, Nate? These women are legends. You owe it to them to get the facts right!” Nate felt so exposed and vulnerable in his pretty tights and delicate blouse as his face turned red. He usually was prepared for his assignments, but they had been flooded with so many things so quickly that he hadn’t put in his normal effort… he hadn’t had time. To his dismay, he became strangely agitated under his confining dancer’s belt and tights as he got more flustered. He muttered a humiliated apology, but the damage was done; another point left the scoreboard. After another couple of minutes and more lost points, Nate’s presentation mercifully ended.
Julian went after Nate. As he was speaking, it was clear from their body language that the Sisters were still unhappy. Julian glanced at Owen helplessly, feeling the pressure mounting as Tara interrupted, “Julian, you’re just reading straight from the booklet. Didn’t you dig up anything new? We expect more than just the basics.” Her tone was sharper now, and several sisters exchanged knowing glances. Julian shuffled his feet nervously, feeling his skirt rustle against his tights.
As the flustered teen continued to stumble through his account of a famous alumna’s leadership, he next was interrupted by Brianna, who raised an eyebrow and asked, “Where did you even get that? That’s not in the notes.” Frustrated, she docked him a point. It would not be his last. He felt his face heat up.
The boys quickly understood their efforts were missing the mark. Each presentation seemed thinner than the last, and the sisters’ polite smiles began to fade, replaced with looks of mild irritation.
Owen was next, and he fared no better. His report was met with stony silence, until Tara finally broke it: “You know, a quick search would have told you so much more. This isn’t what Gamma Delta stands for.” The boys exchanged mortified glances.
Standing red-faced and slightly rattled in his adorable study outfit, he got his notes jumbled up. Elise tapped the table impatiently, “Owen, this is Gamma Delta’s legacy. Where’s the passion? Where are the stories that set our alumnae apart?” The other sissified boys all shifted in their seats as the room grew quieter and more tense.
The sisters grew more demanding, their voices firm and their expressions stern. Madison stood up, folding her arms. “We expect you to care about this. To be part of Gamma Delta, you need to show respect for those who came before.” The boys’ unease grew as the authority in the sisters’ voices made their own shortcomings painfully obvious.
Elise sighed, “Did any of you even try to dig a little deeper? This is your chance to show us you care about Gamma Delta’s legacy. Where are the stories, the interesting facts?” The feminized boys all flushed with embarrassment.
Tara, arms folded, chimed in with a disappointed shake of her head. “You’re supposed to go beyond what’s in your booklets. Did you even look anything up on your own?”
The sisters began docking points with increasing frequency. Milo’s segment on a celebrated Gamma Delta alumna contained only the most basic information, and Cassidy didn’t hesitate to announce, “Minus two for omitting any mention of her extensive scholarship work.”
As their presentations limped to a close, the boys exchanged worried glances, realizing they’d woefully underestimated the task. Tara finally spoke with a disappointed shake of her head, “Next time, we want effort. We want depth. You owe it to the women who built Gamma Delta.”
By the time the Alumna Spotlights were over, the damage was done. The Big Sisters made it clear that next time, they expected research, thoughtful preparation and a genuine appreciation for the traditions and stories that shaped Gamma Delta. The boys’ sorry record of points lost reflected the Sisters’ dissatisfaction. For the first time, they truly understood how easily their hard-earned points could fall away. It was becoming painfully clear that getting to 1000 would be daunting. The Little Darlings all sat meekly in their adorable study outfits and felt a sense of dread at whatever might come next.
7
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 14, 2026, 04:50:52 PM »
Chapter 317.
Mrs Foster took Tim by the hand and led him into the kitchen.
“So you’re training to be a maid. You’ll be spending a lot of time in kitchens, then.”
“If I pass training, Mrs Foster…”
“Oh, don’t worry. You will. I’m going to give you a crash course. Me and the girls.”
“The girls…?”
“Don’t look surprised. They know all about maid training. They’ll look after you when I’m not here. You can trust them implicitly. Just follow their instructions in everything. They’re very good teachers. I trained them, after all…”
“I see…”
“Now, what would you like to eat? Relax and warm up, then we’ll go into the lounge and discuss the programme for the next few days.”
“Oh… I didn’t realise I was staying…”
“Yes, till the end of the week. The idea is to get you back on course. Now what do you like to drink? Milkshake? Chocolate, vanilla or strawberry?”
By the time he’d eaten, and they had repaired to the lounge, Tim was feeling a lot happier. Mrs Foster seemed really caring – so much nicer than some of the trainers at ESDS. But they had only been chatting for a few minutes when there was a ring at the bell. A few seconds later, Clara showed Sasha into the room. For a moment he thought she’d come to take him back. But his fears were quickly allayed.
“Hi Shirley… All right? Just come to drop off Mitzy’s clothes.”
She held up a large pink paper carrier bag.
Tim looked up expectantly. “My uniform?”
“No, Mitzy! We told you. Not till you improve.” She rolled her eyes. “If Mrs Foster gives us good reports, maybe in a week or so.” She put down the bag. “This is a just a change of your present outfit. It’s similar, but it has a nice halter top so you won’t be embarrassed to wear it out, and a change of collar. I’ve put in a shoulder bag and some boots and gloves, too. And a towel, your toothbrush, some toiletries, and a couple of nighties.”
Tim looked alarmed.
“I don’t think I’ll be going out, miss…”
“You never know.”
Mrs Foster smiled. “Say thank you to Sasha, Mitzy. How thoughtful of her.”
“Thank you, Miss Sasha…” he said, sulkily.
“Oh, and Shirley, there’s an envelope in there for Clara. She asked me to print out a few photos from ESDS and from the Centre. She’ll tell you what it’s all about. Well, I’ll be off then. Be a good girl, Mitzy.”
“I’ll be in touch,” grinned Mrs Foster.
After Sasha had left, and Tim was busy, Shirley slipped out the envelope. A4 size. She peeped inside. Photos of Tim as a boot boy and as a maid.
“Ah,” she murmured, “I think I can guess what this is about. I wondered why the girls were whispering about show and share…”
Mrs Foster took Tim by the hand and led him into the kitchen.
“So you’re training to be a maid. You’ll be spending a lot of time in kitchens, then.”
“If I pass training, Mrs Foster…”
“Oh, don’t worry. You will. I’m going to give you a crash course. Me and the girls.”
“The girls…?”
“Don’t look surprised. They know all about maid training. They’ll look after you when I’m not here. You can trust them implicitly. Just follow their instructions in everything. They’re very good teachers. I trained them, after all…”
“I see…”
“Now, what would you like to eat? Relax and warm up, then we’ll go into the lounge and discuss the programme for the next few days.”
“Oh… I didn’t realise I was staying…”
“Yes, till the end of the week. The idea is to get you back on course. Now what do you like to drink? Milkshake? Chocolate, vanilla or strawberry?”
By the time he’d eaten, and they had repaired to the lounge, Tim was feeling a lot happier. Mrs Foster seemed really caring – so much nicer than some of the trainers at ESDS. But they had only been chatting for a few minutes when there was a ring at the bell. A few seconds later, Clara showed Sasha into the room. For a moment he thought she’d come to take him back. But his fears were quickly allayed.
“Hi Shirley… All right? Just come to drop off Mitzy’s clothes.”
She held up a large pink paper carrier bag.
Tim looked up expectantly. “My uniform?”
“No, Mitzy! We told you. Not till you improve.” She rolled her eyes. “If Mrs Foster gives us good reports, maybe in a week or so.” She put down the bag. “This is a just a change of your present outfit. It’s similar, but it has a nice halter top so you won’t be embarrassed to wear it out, and a change of collar. I’ve put in a shoulder bag and some boots and gloves, too. And a towel, your toothbrush, some toiletries, and a couple of nighties.”
Tim looked alarmed.
“I don’t think I’ll be going out, miss…”
“You never know.”
Mrs Foster smiled. “Say thank you to Sasha, Mitzy. How thoughtful of her.”
“Thank you, Miss Sasha…” he said, sulkily.
“Oh, and Shirley, there’s an envelope in there for Clara. She asked me to print out a few photos from ESDS and from the Centre. She’ll tell you what it’s all about. Well, I’ll be off then. Be a good girl, Mitzy.”
“I’ll be in touch,” grinned Mrs Foster.
After Sasha had left, and Tim was busy, Shirley slipped out the envelope. A4 size. She peeped inside. Photos of Tim as a boot boy and as a maid.
“Ah,” she murmured, “I think I can guess what this is about. I wondered why the girls were whispering about show and share…”
8
Active Sissy Stories / Re: Tiffany's Date
« Last post by sissy servant 737-820-633 on January 13, 2026, 03:29:15 PM »
thanks for sending this story back to the top.. turns me on remembering a scene i had with my Mistress..
9
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 13, 2026, 02:21:46 PM »
Chapter 316.
ESDS and Mrs Foster had a long-term understanding. It had all started two years before, when a particularly difficult trainee had been sent off in his maid’s uniform to buy some coffee from the “corner shop”. There was no corner shop, so the poor boy had walked miles, and endured all sorts of humiliations, before he dared to turn round and come back. For some reason he had turned up the drive of the next house; perhaps he was confused, perhaps he wanted a drink of water. Whatever the case, Mrs Foster took him in, fed him, and listened to his story. As he related his experiences, his recruitment, training and disciplining, she grew more and more interested. He too was wearing a dog tag, so she rang ESDS and asked permission to let him stay with her till the next day. True to his training, she found him the most helpful and obliging servant, and he spent a day waiting on her and her daughter, who attended the nearby girls’ school. Long story short, she took over the remainder of his training, which lasted two weeks, and sent him back a proficient and finished maid. She did this using a mixture of kindness (when he worked well) and discipline (when he was careless or lazy). The kindness often involved she or her daughter Clara – or both together – administering physical gratification. The discipline was either applied with the aid of a whip or cane, or some ingenious form of humiliation.
Since then ESDS had been sending her recalcitrant trainees to knock into shape, in return for supplying her with a domestic whenever she needed one. It was a good arrangement for both. In house Shirley Foster was referred to in code as “the annexe”. She worked in the education department of the county council, and in view of her connections to ESDS it was safer not to refer to her by name. Clara and her friend Maggie also assisted, and kept their involvement a secret from their friends. They referred to their activities only as CMMT – Clara and Maggie’s Maid Training, and often attached this acronym to their personal belongings, much to the mystification of their friends. They were as, if not more, inventive than Clara’s mother, and consequently she gave them free rein in dealing with the subjects sent to her for correction. Moreover Clara drove and had her own little car, which was invaluable when mother was busy and one of the maids needed to be transported somewhere, usually for humiliation training – which the girls excelled at.
Poor Tim had no idea what awaited him. At first the lane was deserted. It curved away to the right, and every minute he expected to see the next-door neighbour’s house appear in view, but then the road straightened out and passed through open fields. Fearful of what might await him if he returned, he kept on walking. He could see that in about a quarter of a mile the fields gave way. On the right he could see a red brick house behind the trees. On the left… What was that? His heart froze. It looked like… Yes, a school! And he could see kids in blue uniforms issuing from its gate! No, please, he prayed, let me get to the house before…
There was only one pavement so he couldn’t cross over. Nearer the school was a bus shelter, and he could see girls heading towards it. He speeded up, but he was still a hundred yards or so short when the first little group arrived and took up residence. They’d already seen him – he could see them pointing and fiddling with their phones. He had no choice but to brazen it out. He pretended not to be fazed, even when they greeted him with a chorus of jibes and wolf whistles. He actually said “good afternoon, girls” to them as he passed, which he immediately regretted as all it produced was a howl of laughter and allowed them to photograph his face. Damn! He turned red and hurried on. But soon he was dodging through a tide of giggling schoolgirls who were flooding from the main gates of the Margaret Sanger School – he saw the name-board - onto the narrow pavement. He ignored the gasps and whispers and rude cries – and the clicking of shutters – as well as he could. But several of them deliberately bumped into him, and one of them accused him of touching her, called him a pervert, and tried to make a scene. He fled across the road, ran along the verge, and dashed into the driveway of the first house. This must be it. He made his way up to the house. He was about to ring the bell, when he heard a voice behind him. He turned. Shit! Two of them had followed him in!
“Leave me alone! I’m…er, visitin’ friends, ain’t I?”
“Really? I suppose you’re from ESDS,” said one, a girl with long brown hair and a rather grown-up manner. Does my mum know you’re coming?”
Her friend was looking at him with suppressed glee.
“Omg! What’s your name, sweetie?”
“I-I…was t-told to see Mrs Foster…” stammered Tim, flustered.
“That’s my mum,” said the girl with brown hair, with a smirk.
The blonde clapped her hands in delight. “Clara! We’ve got a new trainee! Yay!” She looked Tim up and down. “But why are you dressed like that… And how did you get here, cutie pie?”
“I w-walked…”
Blonde squealed. “You walked? Like that? Didn’t some of the girls see you?”
Tim’s eyes filled with tears.
“They did! Haha. Who sent you?”
“Miss Nicola…”
“Miss Nicola,” she mimicked. “And what did you do to upset Miss Nicola so much she sent you here like that?”
“I… I dropped a tray, and…”
But at that moment, the door opened and a woman stepped out, dressed in a smart grey suit.
“Hi, girls. And you must be Mitzy… I had a call to expect you.”
“Mitzy?” Blonde was almost speechless with delight.
“I’m Shirley Foster. Welcome, Mitzy. This is my daughter Clara, and her friend Maggie. Mitzy, I believe you have a message for me?”
“Y-yes, Mrs Foster. I have a p-problem… Thank you for agreeing to help…”
“My pleasure. Come in and let’s have a little chat, shall we…?”
ESDS and Mrs Foster had a long-term understanding. It had all started two years before, when a particularly difficult trainee had been sent off in his maid’s uniform to buy some coffee from the “corner shop”. There was no corner shop, so the poor boy had walked miles, and endured all sorts of humiliations, before he dared to turn round and come back. For some reason he had turned up the drive of the next house; perhaps he was confused, perhaps he wanted a drink of water. Whatever the case, Mrs Foster took him in, fed him, and listened to his story. As he related his experiences, his recruitment, training and disciplining, she grew more and more interested. He too was wearing a dog tag, so she rang ESDS and asked permission to let him stay with her till the next day. True to his training, she found him the most helpful and obliging servant, and he spent a day waiting on her and her daughter, who attended the nearby girls’ school. Long story short, she took over the remainder of his training, which lasted two weeks, and sent him back a proficient and finished maid. She did this using a mixture of kindness (when he worked well) and discipline (when he was careless or lazy). The kindness often involved she or her daughter Clara – or both together – administering physical gratification. The discipline was either applied with the aid of a whip or cane, or some ingenious form of humiliation.
Since then ESDS had been sending her recalcitrant trainees to knock into shape, in return for supplying her with a domestic whenever she needed one. It was a good arrangement for both. In house Shirley Foster was referred to in code as “the annexe”. She worked in the education department of the county council, and in view of her connections to ESDS it was safer not to refer to her by name. Clara and her friend Maggie also assisted, and kept their involvement a secret from their friends. They referred to their activities only as CMMT – Clara and Maggie’s Maid Training, and often attached this acronym to their personal belongings, much to the mystification of their friends. They were as, if not more, inventive than Clara’s mother, and consequently she gave them free rein in dealing with the subjects sent to her for correction. Moreover Clara drove and had her own little car, which was invaluable when mother was busy and one of the maids needed to be transported somewhere, usually for humiliation training – which the girls excelled at.
Poor Tim had no idea what awaited him. At first the lane was deserted. It curved away to the right, and every minute he expected to see the next-door neighbour’s house appear in view, but then the road straightened out and passed through open fields. Fearful of what might await him if he returned, he kept on walking. He could see that in about a quarter of a mile the fields gave way. On the right he could see a red brick house behind the trees. On the left… What was that? His heart froze. It looked like… Yes, a school! And he could see kids in blue uniforms issuing from its gate! No, please, he prayed, let me get to the house before…
There was only one pavement so he couldn’t cross over. Nearer the school was a bus shelter, and he could see girls heading towards it. He speeded up, but he was still a hundred yards or so short when the first little group arrived and took up residence. They’d already seen him – he could see them pointing and fiddling with their phones. He had no choice but to brazen it out. He pretended not to be fazed, even when they greeted him with a chorus of jibes and wolf whistles. He actually said “good afternoon, girls” to them as he passed, which he immediately regretted as all it produced was a howl of laughter and allowed them to photograph his face. Damn! He turned red and hurried on. But soon he was dodging through a tide of giggling schoolgirls who were flooding from the main gates of the Margaret Sanger School – he saw the name-board - onto the narrow pavement. He ignored the gasps and whispers and rude cries – and the clicking of shutters – as well as he could. But several of them deliberately bumped into him, and one of them accused him of touching her, called him a pervert, and tried to make a scene. He fled across the road, ran along the verge, and dashed into the driveway of the first house. This must be it. He made his way up to the house. He was about to ring the bell, when he heard a voice behind him. He turned. Shit! Two of them had followed him in!
“Leave me alone! I’m…er, visitin’ friends, ain’t I?”
“Really? I suppose you’re from ESDS,” said one, a girl with long brown hair and a rather grown-up manner. Does my mum know you’re coming?”
Her friend was looking at him with suppressed glee.
“Omg! What’s your name, sweetie?”
“I-I…was t-told to see Mrs Foster…” stammered Tim, flustered.
“That’s my mum,” said the girl with brown hair, with a smirk.
The blonde clapped her hands in delight. “Clara! We’ve got a new trainee! Yay!” She looked Tim up and down. “But why are you dressed like that… And how did you get here, cutie pie?”
“I w-walked…”
Blonde squealed. “You walked? Like that? Didn’t some of the girls see you?”
Tim’s eyes filled with tears.
“They did! Haha. Who sent you?”
“Miss Nicola…”
“Miss Nicola,” she mimicked. “And what did you do to upset Miss Nicola so much she sent you here like that?”
“I… I dropped a tray, and…”
But at that moment, the door opened and a woman stepped out, dressed in a smart grey suit.
“Hi, girls. And you must be Mitzy… I had a call to expect you.”
“Mitzy?” Blonde was almost speechless with delight.
“I’m Shirley Foster. Welcome, Mitzy. This is my daughter Clara, and her friend Maggie. Mitzy, I believe you have a message for me?”
“Y-yes, Mrs Foster. I have a p-problem… Thank you for agreeing to help…”
“My pleasure. Come in and let’s have a little chat, shall we…?”
10
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 13, 2026, 02:07:21 PM »
Chapter 316.
Monday morning. It had been a torrid night, the first for many days that Tim’s coc-k had been released from its confinement, and it had been celebrating its freedom. His alarm went at seven. He climbed out of bed and headed straight for the shower, which he took as cold as he could bear it. Even so, he had to struggle to pack himself away into his little panties. On went the tart costume, and he applied a little lip gloss and blusher as he had been taught. His eyes looked tired, so he put a some eye drops to make them sparkle and applied a touch of mascara. Doreen had unlocked his collar the night before, and now she arrived to lock it on again.
“There. All done. It really suits you, somehow.”
He gave her a look.
“Well, it does. Don’t make a face. It’s true. You look like a little subbie girl, and that’s just perfect for you.”
“I don’t!”
“Don’t you dare speak to me like that, Mitzy!”
“Sorry, miss…”
“You’d better not mess up today, you know that…”
“Yes, miss, I know…”
“Mrs Egerton isn’t the most patient of women… You’re in danger of becoming employed by ESDSS instead of ESDS.”
“ESDSS?”
“Egerton’s Special Domestic Slut Services. Look at yourself. Dressed like that you could end up one of the top earners…”
Tim looked alarmed, then laughed nervously.
“There’s no such thing…”
“No? I wouldn’t be too sure. I’ve heard them talking – her and Lucille. It’s kept very confidential. Small circle. I think Nicola’s part of it, too. Just warning you, Mitzy…”
The idea was hardly reassuring. Even so, Tim couldn’t bring himself to believe it. They wouldn’t stoop that low, he said to himself. I mean, a maid service is one thing… It’s fine for boys to wear nice latex uniforms and be maids, isn’t it? I didn’t realise how cool I could look… Not as cool as I’ll look when I’m a pageboy – a real pageboy – at the wedding. But cool enough. All I want is to be really good at it, and work for ladies that really appreciate me. I wouldn’t have to be down on my knees all the time, either… Well, sometimes, obviously, but… It makes me feel so good when they tell me how promising I am… Priscilla said that, didn’t she? She meant it too… So they wouldn’t keep me dressed like this, would they? Of course not…
Nevertheless he felt nervous for the rest of the morning. And it was this that made him drop the elevenses tray. Just when “mistress” had guests. Not real guests, but Margaret and Nicola acting as guests. He was mortified.
“Ladies… I’m really, really sorry… I’ll get it cleaned up at once.”
He dashed into the kitchen to fetch a bucket and cloths. As he was wetting the cloths he heard murmuring from the living room. He strained his ears.
“…send him to the annexe…”
“…depends what Cassandra decides….”
“….pretty cute in that outfit…put him in the special brochure…”
His hands were shaking as he placed the crockery carefully in the bucket and scrubbed away at the rug. Nicola rose from the sofa and stood watching him.
“Mitzy…” she said, “after lunch you’ll have a couple of hours extra practice waiting on us. Show us you can do it without dropping everything. Lucille will come in and observe, so you need to be aware of your deportment as well. Then I have an errand for you.”
“E-errand, miss?”
“Yes. I want you to give someone a message. Our next-door neighbour, Mrs Foster.”
“Mrs Foster… Yes, miss. Er…what is the message?”
“I want you to tell her you have a problem, and to thank her for agreeing to help.”
Tim looked up, not immediately understanding.
“Say it. I have a problem…”
“I-I h-have a problem…”
“Good. You remember the aitches. Well done. I have a problem. Thank you for agreeing to help.”
“I have a problem… Thank you for agreeing to help…”
“Excellent! She’ll understand. I spoke to her a few minutes ago.”
Tim finished cleaning the rug, had lunch, and returned at one. His waiting training went off without a hitch, and Lucille complimented him on his deportment. At just before three, Sasha called him over.
“You understand your errand?” asked Sasha.
“Y-yes…”
“Good there’s no more to be said. Shirley Foster lives in the next house along. Off you go, then. Turn right out of the drive.”
“B-but… Like this?”
“Of course, I told you,” said Priscilla. “You’ll be able to wear your maid’s outfit as soon as we consider you have attained a suitable standard.”
After he had left the house, Sasha thought of something.
“That’s a point,” she said. “He’ll need a change of clothes if he’s going to be there for a few days. I’ll drop them off tonight on my way out. We’ve got another slutty pink set in his size, I believe.”
“Oh, yes. That one’s got a high-necked cropped top. Actually it’ll be better. More appropriate for wearing outside.”
And they giggled like schoolgirls.
They watched him make his way nervously to the end of the drive. The road was a country lane with a narrow pavement running along the other side. Tim didn’t know it, but Mrs Foster’s house, “The Birches”, was a good half mile away. Priscilla looked at her watch.
“Three o’clock. The girls will be coming out of the Margaret Sanger School any time now.” She winked. “That should be an interesting encounter…”
Monday morning. It had been a torrid night, the first for many days that Tim’s coc-k had been released from its confinement, and it had been celebrating its freedom. His alarm went at seven. He climbed out of bed and headed straight for the shower, which he took as cold as he could bear it. Even so, he had to struggle to pack himself away into his little panties. On went the tart costume, and he applied a little lip gloss and blusher as he had been taught. His eyes looked tired, so he put a some eye drops to make them sparkle and applied a touch of mascara. Doreen had unlocked his collar the night before, and now she arrived to lock it on again.
“There. All done. It really suits you, somehow.”
He gave her a look.
“Well, it does. Don’t make a face. It’s true. You look like a little subbie girl, and that’s just perfect for you.”
“I don’t!”
“Don’t you dare speak to me like that, Mitzy!”
“Sorry, miss…”
“You’d better not mess up today, you know that…”
“Yes, miss, I know…”
“Mrs Egerton isn’t the most patient of women… You’re in danger of becoming employed by ESDSS instead of ESDS.”
“ESDSS?”
“Egerton’s Special Domestic Slut Services. Look at yourself. Dressed like that you could end up one of the top earners…”
Tim looked alarmed, then laughed nervously.
“There’s no such thing…”
“No? I wouldn’t be too sure. I’ve heard them talking – her and Lucille. It’s kept very confidential. Small circle. I think Nicola’s part of it, too. Just warning you, Mitzy…”
The idea was hardly reassuring. Even so, Tim couldn’t bring himself to believe it. They wouldn’t stoop that low, he said to himself. I mean, a maid service is one thing… It’s fine for boys to wear nice latex uniforms and be maids, isn’t it? I didn’t realise how cool I could look… Not as cool as I’ll look when I’m a pageboy – a real pageboy – at the wedding. But cool enough. All I want is to be really good at it, and work for ladies that really appreciate me. I wouldn’t have to be down on my knees all the time, either… Well, sometimes, obviously, but… It makes me feel so good when they tell me how promising I am… Priscilla said that, didn’t she? She meant it too… So they wouldn’t keep me dressed like this, would they? Of course not…
Nevertheless he felt nervous for the rest of the morning. And it was this that made him drop the elevenses tray. Just when “mistress” had guests. Not real guests, but Margaret and Nicola acting as guests. He was mortified.
“Ladies… I’m really, really sorry… I’ll get it cleaned up at once.”
He dashed into the kitchen to fetch a bucket and cloths. As he was wetting the cloths he heard murmuring from the living room. He strained his ears.
“…send him to the annexe…”
“…depends what Cassandra decides….”
“….pretty cute in that outfit…put him in the special brochure…”
His hands were shaking as he placed the crockery carefully in the bucket and scrubbed away at the rug. Nicola rose from the sofa and stood watching him.
“Mitzy…” she said, “after lunch you’ll have a couple of hours extra practice waiting on us. Show us you can do it without dropping everything. Lucille will come in and observe, so you need to be aware of your deportment as well. Then I have an errand for you.”
“E-errand, miss?”
“Yes. I want you to give someone a message. Our next-door neighbour, Mrs Foster.”
“Mrs Foster… Yes, miss. Er…what is the message?”
“I want you to tell her you have a problem, and to thank her for agreeing to help.”
Tim looked up, not immediately understanding.
“Say it. I have a problem…”
“I-I h-have a problem…”
“Good. You remember the aitches. Well done. I have a problem. Thank you for agreeing to help.”
“I have a problem… Thank you for agreeing to help…”
“Excellent! She’ll understand. I spoke to her a few minutes ago.”
Tim finished cleaning the rug, had lunch, and returned at one. His waiting training went off without a hitch, and Lucille complimented him on his deportment. At just before three, Sasha called him over.
“You understand your errand?” asked Sasha.
“Y-yes…”
“Good there’s no more to be said. Shirley Foster lives in the next house along. Off you go, then. Turn right out of the drive.”
“B-but… Like this?”
“Of course, I told you,” said Priscilla. “You’ll be able to wear your maid’s outfit as soon as we consider you have attained a suitable standard.”
After he had left the house, Sasha thought of something.
“That’s a point,” she said. “He’ll need a change of clothes if he’s going to be there for a few days. I’ll drop them off tonight on my way out. We’ve got another slutty pink set in his size, I believe.”
“Oh, yes. That one’s got a high-necked cropped top. Actually it’ll be better. More appropriate for wearing outside.”
And they giggled like schoolgirls.
They watched him make his way nervously to the end of the drive. The road was a country lane with a narrow pavement running along the other side. Tim didn’t know it, but Mrs Foster’s house, “The Birches”, was a good half mile away. Priscilla looked at her watch.
“Three o’clock. The girls will be coming out of the Margaret Sanger School any time now.” She winked. “That should be an interesting encounter…”
The more you give, the more I can give back.
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