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21
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 03, 2025, 09:07:10 AM »
Chapter 263.
Later that evening Bobby and Tim and May and Jessica went out to eat at a local restaurant. Bobby in his new persona. It was to be the first of many such forays. On that first outing Bobby attracted attention, all right – all from young guys. Whenever this happened Tim, who spent most of the evening staring at his friend adoringly, became ridiculously jealous, and found himself holding Bobby’s hand, or putting his arm around him protectively, much to the amusement of the girls. As for Bobby, he exploited Tim’s feelings continually, driving him to distraction by flirting with every other male he encountered. He had finally realised the overwhelming power of being a pretty girl, and practised his sly glances and mascaraed flutterings at every opportunity…
The boys were fully booked the following week, and slightly downcast at the news the wedding had had to be delayed. Tim’s lunchtime appearances in his emasculated state engendered general mirth, several memes, and for Tim himself, severe embarrassment. Ellie told him he had a weekend booking, perhaps trying to cheer him up, but pretended ignorance of the booker, whilst Bobby found out his fate from Mélisande by text first thing Monday morning. Her text began with emojis of a pony and a heart, followed by the news that “on Saturday me and mummy will meet you in stable 13 at 6am”, and promising him a proportion of the take from the pony rides on Sunday at the rate of “20p a ride!! The rest will go to charity – but maybe you’d like to donate your 20ps as well???” Bobby sighed.
“Ellie? Is this true? Do I really have to do pony rides on Sunday?”
“Oh yes. Miss Poole wants to make it a regular thing. There’s a lot of interest, especially since she announced the idea in the monthly newsletter. Ever since the show people are speculating on the identity of the boy dressage pony. Now they have the opportunity to come and actually ride him!”
“But…suppose they find out it’s me…”
“Don’t worry. You’ll be masked up, so no-one will know.”
“Mélisande’s gonna be riding me all Saturday, then I’ve got to give rides to a bunch of kids Sunday… It’s too much…”
“Oh, not only kids, Bobby. Miss Poole set the maximum weight at fifty-five kilos. Why, I’m on about fifty… Maybe I’ll come an have my fifty pence worth too…”
“What? Fifty-five kilos? That means most of the girls here…”
“Quite. You’ll have a busy day…”
With full bookings the week sped by. The boys were in pessimistic mood Friday evening, and went to bed early in anticipation of a difficult weekend…
Saturday morning. Bobby was up with the lark, and had left before Tim was awake. Ellie roused him at eight. He blinked at her with sleepy eyes.
“So…who is it?”
“Who is it?”
“You know what I mean! Whose booked me out for the whole weekend?”
“Oh, well… Actually it’s, er…Serena.”
“What?” He leapt out of bed. “Why didn’t you tell me? What does she want wiv me?”
“Tim…calm down. I have no idea.” She stifled a laugh. “Well, actually, I think she wants to introduce you to her mother…”
“Tim stared. “’Er muvver?”
“Yes. Don’t ask me why… Oh, that’s the door. That maybe her now. Early…”
“I’ll get dressed…”
“Don’t bother. She said she’s bringing your clothes with her.”
“What?”
It was indeed Serena, in jeans, ankle boots and a tweed jacket, and accompanied by two other women in their twenties.
“Hi Ellie. We’ve come for the boy. I’ve brought reinforcements just in case he tries to resist. These are my mum’s work colleagues, Carly and Doreen. Ladies, this is Ellie, the boys’ manager.”
Greetings having been exchanged, Serena looked around.
“So where is he?”
“You’re early. He’s only just woken up, and it sounds like he’s in the shower.”
“Perfect. Here’s his outfit. Will he put it on without any argument, do you think?” She handed Ellie a big pink carrier bag.
“He’ll do what I tell him. Take a seat, ladies. Make yourself coffee. I’ll be back in a few minutes.”
She went back into Tim’s bed room and unpacked the bag onto his bed. A little pink skirt, a Hello Kitty T-shirt, white socks, pink trainers, and a girl’s bomber jacket. And a couple of pairs of stretchy satin panties, one pink and one yellow, with little bows on the waist. She chose the pink ones, to match his skirt, and zipped the other pair into his jacket pocket. She smiled, and waited for him to emerge.
He wasn’t happy, but he knew he had no choice. Ten minutes later he was standing in front of the three visitors, being inspected.
“You’re a cute one,” remarked Doreen, surveying him with an experienced eye.
“You better watch ‘er,” laughed Doreen, pinching his cheek. “Bit of a cradle-snatcher, ‘er.”
“Thanks a million, Ellie,” said Serena. “We’d better get going. Tim’s got an appointment at nine-thirty, and I need to get home and make the food for lunch. “See you in a couple of days.”
The three woman marched him up to the car park. Tim kept his eyes fixed firmly on the ground, but he could hear the gasps and giggles as he passed by the stables. Would he ever live it down? His worst nightmare – dressed as a girl. For Bobby, fair enough. For an alpha male like him… Disaster!
Serena drove an orange Porsche. Doreen sat in the front, Tim and Carly in the back.
“So Tim – do you like your outfit? How does it feel?”
He knew better than to object. If he wanted to survive the weekend, he’d have to pretend compliance.
“Okay…”
“You look really nice…”
She drove into town, and stopped just off the high street.
“Okay, off you go,” she said.
“Where are we goin’?” whimpered Tim, as her friends got out and pulled him from his seat.
“Your nails are a disgrace. Before I introduce you to my mum, you’re going to have them sorted out. Girls – see you back at the house, yeah?”
For Tim, it was a walk of shame, through the middle of town, busy with shoppers. The women walked side by side and made him walk ahead of them.
“Good boy. It’s only a few minutes’ walk,” said Carly, in a motherly tone. “Sahana’s is the best nail salon in town. Serena said you can choose the colour too – so long as it’s bright and glittery!” Of course few people actually noticed the boy neatly dressed as a girl. But for Tim, it was a big ordeal – so much so, that when they finally arrived at Sahana’s, he was actually relieved…
Later that evening Bobby and Tim and May and Jessica went out to eat at a local restaurant. Bobby in his new persona. It was to be the first of many such forays. On that first outing Bobby attracted attention, all right – all from young guys. Whenever this happened Tim, who spent most of the evening staring at his friend adoringly, became ridiculously jealous, and found himself holding Bobby’s hand, or putting his arm around him protectively, much to the amusement of the girls. As for Bobby, he exploited Tim’s feelings continually, driving him to distraction by flirting with every other male he encountered. He had finally realised the overwhelming power of being a pretty girl, and practised his sly glances and mascaraed flutterings at every opportunity…
The boys were fully booked the following week, and slightly downcast at the news the wedding had had to be delayed. Tim’s lunchtime appearances in his emasculated state engendered general mirth, several memes, and for Tim himself, severe embarrassment. Ellie told him he had a weekend booking, perhaps trying to cheer him up, but pretended ignorance of the booker, whilst Bobby found out his fate from Mélisande by text first thing Monday morning. Her text began with emojis of a pony and a heart, followed by the news that “on Saturday me and mummy will meet you in stable 13 at 6am”, and promising him a proportion of the take from the pony rides on Sunday at the rate of “20p a ride!! The rest will go to charity – but maybe you’d like to donate your 20ps as well???” Bobby sighed.
“Ellie? Is this true? Do I really have to do pony rides on Sunday?”
“Oh yes. Miss Poole wants to make it a regular thing. There’s a lot of interest, especially since she announced the idea in the monthly newsletter. Ever since the show people are speculating on the identity of the boy dressage pony. Now they have the opportunity to come and actually ride him!”
“But…suppose they find out it’s me…”
“Don’t worry. You’ll be masked up, so no-one will know.”
“Mélisande’s gonna be riding me all Saturday, then I’ve got to give rides to a bunch of kids Sunday… It’s too much…”
“Oh, not only kids, Bobby. Miss Poole set the maximum weight at fifty-five kilos. Why, I’m on about fifty… Maybe I’ll come an have my fifty pence worth too…”
“What? Fifty-five kilos? That means most of the girls here…”
“Quite. You’ll have a busy day…”
With full bookings the week sped by. The boys were in pessimistic mood Friday evening, and went to bed early in anticipation of a difficult weekend…
Saturday morning. Bobby was up with the lark, and had left before Tim was awake. Ellie roused him at eight. He blinked at her with sleepy eyes.
“So…who is it?”
“Who is it?”
“You know what I mean! Whose booked me out for the whole weekend?”
“Oh, well… Actually it’s, er…Serena.”
“What?” He leapt out of bed. “Why didn’t you tell me? What does she want wiv me?”
“Tim…calm down. I have no idea.” She stifled a laugh. “Well, actually, I think she wants to introduce you to her mother…”
“Tim stared. “’Er muvver?”
“Yes. Don’t ask me why… Oh, that’s the door. That maybe her now. Early…”
“I’ll get dressed…”
“Don’t bother. She said she’s bringing your clothes with her.”
“What?”
It was indeed Serena, in jeans, ankle boots and a tweed jacket, and accompanied by two other women in their twenties.
“Hi Ellie. We’ve come for the boy. I’ve brought reinforcements just in case he tries to resist. These are my mum’s work colleagues, Carly and Doreen. Ladies, this is Ellie, the boys’ manager.”
Greetings having been exchanged, Serena looked around.
“So where is he?”
“You’re early. He’s only just woken up, and it sounds like he’s in the shower.”
“Perfect. Here’s his outfit. Will he put it on without any argument, do you think?” She handed Ellie a big pink carrier bag.
“He’ll do what I tell him. Take a seat, ladies. Make yourself coffee. I’ll be back in a few minutes.”
She went back into Tim’s bed room and unpacked the bag onto his bed. A little pink skirt, a Hello Kitty T-shirt, white socks, pink trainers, and a girl’s bomber jacket. And a couple of pairs of stretchy satin panties, one pink and one yellow, with little bows on the waist. She chose the pink ones, to match his skirt, and zipped the other pair into his jacket pocket. She smiled, and waited for him to emerge.
He wasn’t happy, but he knew he had no choice. Ten minutes later he was standing in front of the three visitors, being inspected.
“You’re a cute one,” remarked Doreen, surveying him with an experienced eye.
“You better watch ‘er,” laughed Doreen, pinching his cheek. “Bit of a cradle-snatcher, ‘er.”
“Thanks a million, Ellie,” said Serena. “We’d better get going. Tim’s got an appointment at nine-thirty, and I need to get home and make the food for lunch. “See you in a couple of days.”
The three woman marched him up to the car park. Tim kept his eyes fixed firmly on the ground, but he could hear the gasps and giggles as he passed by the stables. Would he ever live it down? His worst nightmare – dressed as a girl. For Bobby, fair enough. For an alpha male like him… Disaster!
Serena drove an orange Porsche. Doreen sat in the front, Tim and Carly in the back.
“So Tim – do you like your outfit? How does it feel?”
He knew better than to object. If he wanted to survive the weekend, he’d have to pretend compliance.
“Okay…”
“You look really nice…”
She drove into town, and stopped just off the high street.
“Okay, off you go,” she said.
“Where are we goin’?” whimpered Tim, as her friends got out and pulled him from his seat.
“Your nails are a disgrace. Before I introduce you to my mum, you’re going to have them sorted out. Girls – see you back at the house, yeah?”
For Tim, it was a walk of shame, through the middle of town, busy with shoppers. The women walked side by side and made him walk ahead of them.
“Good boy. It’s only a few minutes’ walk,” said Carly, in a motherly tone. “Sahana’s is the best nail salon in town. Serena said you can choose the colour too – so long as it’s bright and glittery!” Of course few people actually noticed the boy neatly dressed as a girl. But for Tim, it was a big ordeal – so much so, that when they finally arrived at Sahana’s, he was actually relieved…
22
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 03, 2025, 08:59:47 AM »
Chapter 262.
“Keep your head still, Tim! Let me see… Good boy! Finished up your yummy c-ummy treat! Okay. Let’s get you out of there… Goodness! Is that the strap-on? Did you really take all that so easily? Was it nice?”
She unbuckled his gag and prised it gently out of his mouth.
“There… Does that feel better? It’s quite big…”
“My jaw flippin’ aches…”
“Oh, it’ll soon wear off.”
She released him from the cross and helped him to his feet. He groaned and stretched. Ellie glanced at the front of his shorts. The usual eye-catching vertical bulge had been replaced by a cute little curled protuberance no thicker than a breakfast sausage, with a neat, slightly pointed, tip. She couldn’t suppress a giggle. Tim glared at her.
“It ain’t funny! Do you ‘ave the key?”
“Sorry, Tim. Candy kept it. It wasn’t for me to…”
His eyes filled with tears. “Please, Ellie… Can you ask her for it? I can’t walk around like this…”
“Oh, let’s leave it till tomorrow. Then I’ll see what I can do.”
“Ask Miss Poole! Please!”
“Well she’ll have left now. Tomorrow, okay?”
“All right…” He sniffed. “Why did they do all them fings to me…?”
“Oh, don’t make such a fuss! Don’t tell me you didn’t enjoy it. I won’t believe you. Now come on, let’s get you showered and changed. It’s out of hours now so you can wear civvies. And there’s a big surprise waiting for you, as I said.”
Thirty minutes later they were heading up the hill towards the offices, and the canteen. Tim was wearing jeans and a T-shirt. As they approached the top of the path Ellie caught sight of May waving from the canteen window, and she waved back.
“Is that Bobby?” asked Tim, peering.
“Bobby and May.”
“Where’s ‘e bin all afternoon. Does ‘e know what I’ve bin frough?”
At the canteen door Ellie stood aside to let Tim go first. He was half way to their table when he stopped dead, and his mouth fell open.
“What’s up, Tim?” asked Ellie, innocently.
“B-Bobby…?”
“Hi Tim!”
“Is that…you?”
“Yes, idiot. Who do you think…”
“You look…fuc-king incredible…”
Ellie took him by the shoulders, marched him over to the table, and sat him down opposite his friend. For some time he could do nothing but stare.
“See? I got the dress. And a makeover. Do you like it?”
“It’s like my dream… I mean, I can’t believe… You look so… Your ‘air…”
“It’s extensions. I can’t stay like this. But now I know I can really look like…almost be…a girl. It’s an amazing feeling, Tim.”
“For me, too…”
Ellie and May exchanged glances. Seemed like they were both happy now…
“Keep your head still, Tim! Let me see… Good boy! Finished up your yummy c-ummy treat! Okay. Let’s get you out of there… Goodness! Is that the strap-on? Did you really take all that so easily? Was it nice?”
She unbuckled his gag and prised it gently out of his mouth.
“There… Does that feel better? It’s quite big…”
“My jaw flippin’ aches…”
“Oh, it’ll soon wear off.”
She released him from the cross and helped him to his feet. He groaned and stretched. Ellie glanced at the front of his shorts. The usual eye-catching vertical bulge had been replaced by a cute little curled protuberance no thicker than a breakfast sausage, with a neat, slightly pointed, tip. She couldn’t suppress a giggle. Tim glared at her.
“It ain’t funny! Do you ‘ave the key?”
“Sorry, Tim. Candy kept it. It wasn’t for me to…”
His eyes filled with tears. “Please, Ellie… Can you ask her for it? I can’t walk around like this…”
“Oh, let’s leave it till tomorrow. Then I’ll see what I can do.”
“Ask Miss Poole! Please!”
“Well she’ll have left now. Tomorrow, okay?”
“All right…” He sniffed. “Why did they do all them fings to me…?”
“Oh, don’t make such a fuss! Don’t tell me you didn’t enjoy it. I won’t believe you. Now come on, let’s get you showered and changed. It’s out of hours now so you can wear civvies. And there’s a big surprise waiting for you, as I said.”
Thirty minutes later they were heading up the hill towards the offices, and the canteen. Tim was wearing jeans and a T-shirt. As they approached the top of the path Ellie caught sight of May waving from the canteen window, and she waved back.
“Is that Bobby?” asked Tim, peering.
“Bobby and May.”
“Where’s ‘e bin all afternoon. Does ‘e know what I’ve bin frough?”
At the canteen door Ellie stood aside to let Tim go first. He was half way to their table when he stopped dead, and his mouth fell open.
“What’s up, Tim?” asked Ellie, innocently.
“B-Bobby…?”
“Hi Tim!”
“Is that…you?”
“Yes, idiot. Who do you think…”
“You look…fuc-king incredible…”
Ellie took him by the shoulders, marched him over to the table, and sat him down opposite his friend. For some time he could do nothing but stare.
“See? I got the dress. And a makeover. Do you like it?”
“It’s like my dream… I mean, I can’t believe… You look so… Your ‘air…”
“It’s extensions. I can’t stay like this. But now I know I can really look like…almost be…a girl. It’s an amazing feeling, Tim.”
“For me, too…”
Ellie and May exchanged glances. Seemed like they were both happy now…
23
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 03, 2025, 08:48:33 AM »
Chapter 261.
As Ellie made her way between the stable blocks, she could see Bobby in his new dress posing outside the parlour while May snapped away with her phone. As she got closer she realised just how amazing he looked. She caught up with them.
“Hi guys… Bobby, you look incredible!”
“Thank you, Ellie…”
“I mean it. You’re really a girl! Tim going to wet his pants when he sees you.”
“Is he in?” asked May.
“Well, sort of… He’s recovering from a long hard session. I’m going to go and sort him out, so keep out of the parlour for the time being. In fact, why don’t you go up to the canteen and have a drink or something to eat, so I can get him cleaned up? Then I’ll bring him up to meet you – and give him the shock of his life!”
“Okay. I could do with a coffee at least. Come on Bobby.”
Ellie let herself in, walked through the waiting-room and opened the parlour door. She had to giggle, seeing Tim down on all fours, the rubber ball in front of his mouth, his eyes pathetic with that “it’s not fair” expression he sometimes adopted.
“Have a nice time, darling?”
She squatted down and pulled out the plug of his gag.
“Dear, dear. Still half full? Finish that up like a good boy and I’ll come and release you.”
Tim frowned and shook his head.
“Up to you, sweetie.” She noticed the jar of condensed milk and the syringe, and thoughtfully topped up the reservoir. “There, that’ll be more tasty. I have to make a phone call. I’ll come back and check in fifteen minutes. If it’s empty I’ll let you out. Oh, and there’s a nice surprise – no, a really nice surprise waiting for you. So if I were you…”
She patted his head, stood up and left, closing the door behind her. She threw herself down on the sofa in the living-room, and dialled Serena’s number.
“Serena? Hi, it’s Ellie.”
“Hi, Ellie…”
“Miss Poole tells me you’ve booked Tim for the whole of next weekend. I just wanted to confirm so I can put it in the book.”
“That’s right! I was lucky that wedding thing got put off.”
“Yes… Okay, that’s done. Can you pick him up at nine Saturday morning?”
“Will do.”
“Any special requirements?”
“I don’t think so… You have some masks and gags, right?”
“I’ll put them in. How do you want him dressed?”
“Naked? Is that possible?”
Ellie laughed.
“No, I’m joking. Actually I’ve already got him a little everyday outfit. I’ll bring it with me.
“Okay…
“I’ll come about quarter-to then. Maybe you can help me get him dressed.”
“Okay… What is it? Is it going to fit him?”
“Oh, a simple outfit. Nothing special. Yes, I’m sure it’ll fit. I got his size from that nice lady at Fantastex.”
“Cynthia?”
“That’s right. Miss Poole recommended her. She’s making him a couple of things for the rest of the weekend.”
“Is she…?”
“Yes. My mum’s having a little bash on Saturday. She’s changing jobs.”
“Your mum?”
“Yes. I told her all about the boys. She’s going to book a session some time. She’s dying to meet Tim.”
“Right…”
“So as I say, she and her work friends are having a little get-together Saturday, then Saturday evening they’re going off for a few days on the coast – Norfolk, I think. That means I’ll have the house to myself, and I’ll have a few of my mates round when the coast’s clear.”
“So Tim…”
“It’ll be a working weekend.”
“He’ll need his equipment then…”
“Oh, no. Not that sort of work. Just general domestic duties.”
Ellie laughed. “Oh, he’ll like that… Make a nice change from being on his knees all day…”
“I hope so. Though I can’t guarantee he won’t be on his knees some of the time,” she added, archly. “Miss Poole is very keen the boys should learn new skills… Widen their remit. All that untapped potential…”
“Quite, Serena. But I must tell you one thing. He had a long session today with a couple of the girls, and ended up with a chastity device! I’ll make sure to have that taken off before Saturday.”
“Chastity device? Really? No, don’t take it off – leave it on, please…”
“Okay, if you say so… I’ll let you have the key.”
“Okay.”
“That’s all done, then. See you Saturday.”
Ellie put down the phone and sat back. “Fantastex, eh?” she murmured. “Wonder what she’s getting for him from there. I could ask Cynthia… But, no. That would be unprofessional. It’ll all come out in the wash, anyway…” She smiled. “Well better go sort him out, I suppose…”
As Ellie made her way between the stable blocks, she could see Bobby in his new dress posing outside the parlour while May snapped away with her phone. As she got closer she realised just how amazing he looked. She caught up with them.
“Hi guys… Bobby, you look incredible!”
“Thank you, Ellie…”
“I mean it. You’re really a girl! Tim going to wet his pants when he sees you.”
“Is he in?” asked May.
“Well, sort of… He’s recovering from a long hard session. I’m going to go and sort him out, so keep out of the parlour for the time being. In fact, why don’t you go up to the canteen and have a drink or something to eat, so I can get him cleaned up? Then I’ll bring him up to meet you – and give him the shock of his life!”
“Okay. I could do with a coffee at least. Come on Bobby.”
Ellie let herself in, walked through the waiting-room and opened the parlour door. She had to giggle, seeing Tim down on all fours, the rubber ball in front of his mouth, his eyes pathetic with that “it’s not fair” expression he sometimes adopted.
“Have a nice time, darling?”
She squatted down and pulled out the plug of his gag.
“Dear, dear. Still half full? Finish that up like a good boy and I’ll come and release you.”
Tim frowned and shook his head.
“Up to you, sweetie.” She noticed the jar of condensed milk and the syringe, and thoughtfully topped up the reservoir. “There, that’ll be more tasty. I have to make a phone call. I’ll come back and check in fifteen minutes. If it’s empty I’ll let you out. Oh, and there’s a nice surprise – no, a really nice surprise waiting for you. So if I were you…”
She patted his head, stood up and left, closing the door behind her. She threw herself down on the sofa in the living-room, and dialled Serena’s number.
“Serena? Hi, it’s Ellie.”
“Hi, Ellie…”
“Miss Poole tells me you’ve booked Tim for the whole of next weekend. I just wanted to confirm so I can put it in the book.”
“That’s right! I was lucky that wedding thing got put off.”
“Yes… Okay, that’s done. Can you pick him up at nine Saturday morning?”
“Will do.”
“Any special requirements?”
“I don’t think so… You have some masks and gags, right?”
“I’ll put them in. How do you want him dressed?”
“Naked? Is that possible?”
Ellie laughed.
“No, I’m joking. Actually I’ve already got him a little everyday outfit. I’ll bring it with me.
“Okay…
“I’ll come about quarter-to then. Maybe you can help me get him dressed.”
“Okay… What is it? Is it going to fit him?”
“Oh, a simple outfit. Nothing special. Yes, I’m sure it’ll fit. I got his size from that nice lady at Fantastex.”
“Cynthia?”
“That’s right. Miss Poole recommended her. She’s making him a couple of things for the rest of the weekend.”
“Is she…?”
“Yes. My mum’s having a little bash on Saturday. She’s changing jobs.”
“Your mum?”
“Yes. I told her all about the boys. She’s going to book a session some time. She’s dying to meet Tim.”
“Right…”
“So as I say, she and her work friends are having a little get-together Saturday, then Saturday evening they’re going off for a few days on the coast – Norfolk, I think. That means I’ll have the house to myself, and I’ll have a few of my mates round when the coast’s clear.”
“So Tim…”
“It’ll be a working weekend.”
“He’ll need his equipment then…”
“Oh, no. Not that sort of work. Just general domestic duties.”
Ellie laughed. “Oh, he’ll like that… Make a nice change from being on his knees all day…”
“I hope so. Though I can’t guarantee he won’t be on his knees some of the time,” she added, archly. “Miss Poole is very keen the boys should learn new skills… Widen their remit. All that untapped potential…”
“Quite, Serena. But I must tell you one thing. He had a long session today with a couple of the girls, and ended up with a chastity device! I’ll make sure to have that taken off before Saturday.”
“Chastity device? Really? No, don’t take it off – leave it on, please…”
“Okay, if you say so… I’ll let you have the key.”
“Okay.”
“That’s all done, then. See you Saturday.”
Ellie put down the phone and sat back. “Fantastex, eh?” she murmured. “Wonder what she’s getting for him from there. I could ask Cynthia… But, no. That would be unprofessional. It’ll all come out in the wash, anyway…” She smiled. “Well better go sort him out, I suppose…”
24
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 03, 2025, 08:38:29 AM »
Chapter 260.
Ellie was in no hurry to get back and rescue Tim. She waited in the canteen for the girls to show up as arranged. She listened attentively as they related the events of the afternoon, a quiet smile on her face.
“Sounds like you did a great job, girls. Miss Poole will be very happy. He’s going to be rather miffed when I get back, I suspect.”
“He’ll be furious, I imagine,” laughed Phillipa.
“No, I don’t think so…” mused Ellie. “Don’t underestimate the effect that device will have. I know from experience there’s no better way of subduing a bloke. Tim will know he has to be ultra-polite and nice to us if he wants it taken off. He’ll be a pussy until then.”
“Yeah,” said Candy. “But when it comes off on Saturday morning, imagine the reaction!”
“Ah… I haven’t told you…”
“Told us…?” began Phillipa.
“The wedding’s postponed.”
“What?” the girls chorused.
“Yes. Family illness.”
“But…?
“Miss Poole told me but asked me not to tell you. She wanted you to go ahead as planned.”
“But we thought it was all about saving him for the wedding…” said Candy.
“Maybe that was part of it. But maybe Miss Poole just wanted to see him punished. She thought he was getting too full of himself, and needed to be put in his place.”
“Would she really think like that?”
“Oh, yes, Phillipa. Don’t you ever repeat anything I tell you, okay? Understood?”
“Yes, Ellie. Understood.”
“Okay. Miss Poole. You must understand what drives her. She created the boot parlour to make money, of course. But she also likes the idea of two big boys having to grovel for the female staff. She loves the idea of their humiliation and submission. It’s her thing. She gets all the videos from the boot parlour sent to her by Evelina. She thought the pageboy outfits would be really embarrassing for the boys, but then Tim used his to show off. She wanted to remind him of his place.”
“Wow… I didn’t realise…”
“So…what about the chastity device?” asked Candy. “Will you take it off now?”
“Certainly not! In fact, she wants me to make sure he goes to lunch in the canteen every day this week, so everyone can see his non-existent boyhood! It’ll be obvious to everyone he’s been seriously emasculated.”
“So how long will he have to…?”
“Probably for a few days. Miss Poole tells me that Serena’s snapped him up for the whole weekend!”
“Serena? Oh my god…” gasped Phillipa.
“Quite. I have to ring her tonight to confirm the booking. Maybe I’ll find out more. I’ll tell you if I do. Imagine being at her beck and call for a whole weekend! I’d love to be a fly on the wall.” She checked her watch. “But I’d better go – it’s late. Poor Tim will be getting lonely.” She glanced out of the window. “Oh, and I think that’s Bobby and May! Looks like he got his dress! Must rush…”
Ellie was in no hurry to get back and rescue Tim. She waited in the canteen for the girls to show up as arranged. She listened attentively as they related the events of the afternoon, a quiet smile on her face.
“Sounds like you did a great job, girls. Miss Poole will be very happy. He’s going to be rather miffed when I get back, I suspect.”
“He’ll be furious, I imagine,” laughed Phillipa.
“No, I don’t think so…” mused Ellie. “Don’t underestimate the effect that device will have. I know from experience there’s no better way of subduing a bloke. Tim will know he has to be ultra-polite and nice to us if he wants it taken off. He’ll be a pussy until then.”
“Yeah,” said Candy. “But when it comes off on Saturday morning, imagine the reaction!”
“Ah… I haven’t told you…”
“Told us…?” began Phillipa.
“The wedding’s postponed.”
“What?” the girls chorused.
“Yes. Family illness.”
“But…?
“Miss Poole told me but asked me not to tell you. She wanted you to go ahead as planned.”
“But we thought it was all about saving him for the wedding…” said Candy.
“Maybe that was part of it. But maybe Miss Poole just wanted to see him punished. She thought he was getting too full of himself, and needed to be put in his place.”
“Would she really think like that?”
“Oh, yes, Phillipa. Don’t you ever repeat anything I tell you, okay? Understood?”
“Yes, Ellie. Understood.”
“Okay. Miss Poole. You must understand what drives her. She created the boot parlour to make money, of course. But she also likes the idea of two big boys having to grovel for the female staff. She loves the idea of their humiliation and submission. It’s her thing. She gets all the videos from the boot parlour sent to her by Evelina. She thought the pageboy outfits would be really embarrassing for the boys, but then Tim used his to show off. She wanted to remind him of his place.”
“Wow… I didn’t realise…”
“So…what about the chastity device?” asked Candy. “Will you take it off now?”
“Certainly not! In fact, she wants me to make sure he goes to lunch in the canteen every day this week, so everyone can see his non-existent boyhood! It’ll be obvious to everyone he’s been seriously emasculated.”
“So how long will he have to…?”
“Probably for a few days. Miss Poole tells me that Serena’s snapped him up for the whole weekend!”
“Serena? Oh my god…” gasped Phillipa.
“Quite. I have to ring her tonight to confirm the booking. Maybe I’ll find out more. I’ll tell you if I do. Imagine being at her beck and call for a whole weekend! I’d love to be a fly on the wall.” She checked her watch. “But I’d better go – it’s late. Poor Tim will be getting lonely.” She glanced out of the window. “Oh, and I think that’s Bobby and May! Looks like he got his dress! Must rush…”
25
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 03, 2025, 08:33:07 AM »
Chapter 259.
The girls had a plan, but in any case, it was fun having such complete control over such a big guy, and showing him what real sex was like. So they continued their work with diligence and discipline, until Tim had experienced three more shuddering climaxes, and the teat on the sheath was as large as a ping-pong ball, and hanging down almost to the floor. Then Candy finally carefully withdrew, and closed the rear flap. Tim slumped – as much as he could in his shackles, and sighed faintly. They were almost finished with him. But not quite. The plan, cooked up with Ellie and sanctioned by a higher disciplinary authority, had a pre-arranged endgame.
Candy divested herself of the strap-on, and retrieved a little plastic box from the cupboard. Simultaneously Phillipa was removing the long sheath from Tim’s dangling and much shrunken member, carefully so as not to spill any of its precious contents. She clipped the neck and laid it aside, then cleaned Tim meticulously with baby wipes.
“I’m sorry, Tim,” Candy was saying, holding a shiny steel chastity device, slightly curved, with a pen-is-shaped head, in front of his nose, “but this was the only way we were ever going to get this on you.”
Tim was trying to speak but the only sounds he was making were inarticulate whines of protest. Ignoring them, Candy knelt next to Phillipa and prepared to fit the device.
“Think yourself lucky. We did consider a flat one, which would have totally feminised you, but decided for you it would have been impractical. This one isn’t very long, but at least it’s the right shape, so in your latex shorts you’ll look as though you have a pen-is, though rather a little one. Now…base ring…good…let’s get you in…lucky it’s shrunk so well…tight squeeze… There! Done. Lock it… I have the only key, Tim, so you won’t be getting out till I decide… When, did you say? Well, just before the wedding next Saturday. Your little coc-k will be so happy to get released it’ll go wild – especially at the reception, with all those girls chatting you up. Can’t wait to see the wedding photos!”
She pushed the device into his shorts and closed the front. Tim was struggling now, but there was no way the girls were going to release him.
“Ellie will let you out in an hour or so,” said Phillipa.
She moved round to his head and unplugged the reservoir of his gag.
“Good boy! You must have been suc-king hard – it’s nearly empty. Don’t fret. I’ve got something even more delicious for you!”
And she began to syringe his c-um out of the condom and into the reservoir. When it was full she re-plugged it and gave it a squeeze, filling his mouth. His eyes widened.
“Nice? There’s just enough left to top it up… She syringed up the rest, and injected it into the gag. There! Full again. Happy suc-king. See you around, then…”
And the girls simply walked out, discussing the club they were off to that evening…
The girls had a plan, but in any case, it was fun having such complete control over such a big guy, and showing him what real sex was like. So they continued their work with diligence and discipline, until Tim had experienced three more shuddering climaxes, and the teat on the sheath was as large as a ping-pong ball, and hanging down almost to the floor. Then Candy finally carefully withdrew, and closed the rear flap. Tim slumped – as much as he could in his shackles, and sighed faintly. They were almost finished with him. But not quite. The plan, cooked up with Ellie and sanctioned by a higher disciplinary authority, had a pre-arranged endgame.
Candy divested herself of the strap-on, and retrieved a little plastic box from the cupboard. Simultaneously Phillipa was removing the long sheath from Tim’s dangling and much shrunken member, carefully so as not to spill any of its precious contents. She clipped the neck and laid it aside, then cleaned Tim meticulously with baby wipes.
“I’m sorry, Tim,” Candy was saying, holding a shiny steel chastity device, slightly curved, with a pen-is-shaped head, in front of his nose, “but this was the only way we were ever going to get this on you.”
Tim was trying to speak but the only sounds he was making were inarticulate whines of protest. Ignoring them, Candy knelt next to Phillipa and prepared to fit the device.
“Think yourself lucky. We did consider a flat one, which would have totally feminised you, but decided for you it would have been impractical. This one isn’t very long, but at least it’s the right shape, so in your latex shorts you’ll look as though you have a pen-is, though rather a little one. Now…base ring…good…let’s get you in…lucky it’s shrunk so well…tight squeeze… There! Done. Lock it… I have the only key, Tim, so you won’t be getting out till I decide… When, did you say? Well, just before the wedding next Saturday. Your little coc-k will be so happy to get released it’ll go wild – especially at the reception, with all those girls chatting you up. Can’t wait to see the wedding photos!”
She pushed the device into his shorts and closed the front. Tim was struggling now, but there was no way the girls were going to release him.
“Ellie will let you out in an hour or so,” said Phillipa.
She moved round to his head and unplugged the reservoir of his gag.
“Good boy! You must have been suc-king hard – it’s nearly empty. Don’t fret. I’ve got something even more delicious for you!”
And she began to syringe his c-um out of the condom and into the reservoir. When it was full she re-plugged it and gave it a squeeze, filling his mouth. His eyes widened.
“Nice? There’s just enough left to top it up… She syringed up the rest, and injected it into the gag. There! Full again. Happy suc-king. See you around, then…”
And the girls simply walked out, discussing the club they were off to that evening…
26
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by cindydolly on November 03, 2025, 08:30:09 AM »
This already is a wonderful story developing
Thank you so much for your great writing
Thank you so much for your great writing
27
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 03, 2025, 08:28:55 AM »
Chapter 258.
While Phillipa pulled on a pair of fine transparent latex gloves and knelt down at Tim’s side, Candy popped open the rear flap of his modified shorts. He moaned, squirmed and tried to pull away, but his bonds held him fast. He could only rotate his bottom, trying to make her task more difficult, but it only emphasized his helplessness.
“How cute! Are you impatient for your little dil-do, darling? Don’t worry – I’m just lubricating it for entry.” The grey shaft was gleaming with lube. She put down the bottle and pushed the head gently but firmly between his buttocks. His attempt to repel it by squeezing them together was quite ineffectual. The head slipped through easily - there was a moment’s pause as it encountered its goal - Candy pushed a little harder, the head penetrated slowly, and the, with a sudden rush, it was in, eliciting a shocked squeak from its unwilling recipient.
Candy sighed with satisfaction.
“I’m in, Phillipa. We should go slowly at first.”
“I am,” said Phillipa, who had already begun massaging Tim’s coc-k, pointing at the floor at forty-five degrees to his belly, as fat and red in its latex skin as a large bratwurst, and twitching with arousal.
“Squeeze, pull, relax…squeeze, pull relax… Is that about right, Candy?”
“Perfect, Phillipa. You have such a good sense of rhythm. I’ll keep time with my thrusts… He’s really taking this well… It’s sliding back and forth so easily…and look - it’s going right in up to the hilt!”
At first, Tim was emitting a faint, continuous whine. But after a couple of minutes it faded away, and was replaced by a grunt at every thrust.
“I think he’s getting the idea,” she murmured. “He’s definitely working with me now… Pushing back as I thrust…” She raised her voice. “Good boy! There, don’t tell me this isn’t the best thing you’ve ever felt…”
“Candy, he’s making so much juice. The teat’s already quite full. It’s swinging backwards and forwards as I milk him!”
“Soon perhaps we’ll get some cream to go with it… Just carry on at the same pace, and let’s see what…”
But she didn’t get to finish her sentence. Tim gave a sort of choking sob, and then his helpless torso was racked with climactic spasms.
“Don’t stop!” cried Candy, maintaining the steady back and forth rhythm. “Keep milking!”
Phillipa gasped – she could feel the violence of Tim’s orgasm under her fingers, the sperm being pumped out in great spurts.
“Gosh! It’s so powerful!”
Her eyes widened as she watched the spherical teat inflating, filling with c-um, in front of her face.
“There’s so much…”
Slowly Tim subsided, amidst little satisfied moans.
“Sounds like he enjoyed that,” smirked Candy.
“Look how much c-um he made!”
Candy peered round. The teat was hanging down, heavy with Tim’s first ejaculation. Phillipa squeezed it.
“It’s all squidgy and warm!” she giggled.
“Give him a minute or two, yeah, and we’ll see what he’s got left… Do you want a go with the strap-on?”
“Maybe one go… But I like doing this. It feels so cool when he pops…”
While Phillipa pulled on a pair of fine transparent latex gloves and knelt down at Tim’s side, Candy popped open the rear flap of his modified shorts. He moaned, squirmed and tried to pull away, but his bonds held him fast. He could only rotate his bottom, trying to make her task more difficult, but it only emphasized his helplessness.
“How cute! Are you impatient for your little dil-do, darling? Don’t worry – I’m just lubricating it for entry.” The grey shaft was gleaming with lube. She put down the bottle and pushed the head gently but firmly between his buttocks. His attempt to repel it by squeezing them together was quite ineffectual. The head slipped through easily - there was a moment’s pause as it encountered its goal - Candy pushed a little harder, the head penetrated slowly, and the, with a sudden rush, it was in, eliciting a shocked squeak from its unwilling recipient.
Candy sighed with satisfaction.
“I’m in, Phillipa. We should go slowly at first.”
“I am,” said Phillipa, who had already begun massaging Tim’s coc-k, pointing at the floor at forty-five degrees to his belly, as fat and red in its latex skin as a large bratwurst, and twitching with arousal.
“Squeeze, pull, relax…squeeze, pull relax… Is that about right, Candy?”
“Perfect, Phillipa. You have such a good sense of rhythm. I’ll keep time with my thrusts… He’s really taking this well… It’s sliding back and forth so easily…and look - it’s going right in up to the hilt!”
At first, Tim was emitting a faint, continuous whine. But after a couple of minutes it faded away, and was replaced by a grunt at every thrust.
“I think he’s getting the idea,” she murmured. “He’s definitely working with me now… Pushing back as I thrust…” She raised her voice. “Good boy! There, don’t tell me this isn’t the best thing you’ve ever felt…”
“Candy, he’s making so much juice. The teat’s already quite full. It’s swinging backwards and forwards as I milk him!”
“Soon perhaps we’ll get some cream to go with it… Just carry on at the same pace, and let’s see what…”
But she didn’t get to finish her sentence. Tim gave a sort of choking sob, and then his helpless torso was racked with climactic spasms.
“Don’t stop!” cried Candy, maintaining the steady back and forth rhythm. “Keep milking!”
Phillipa gasped – she could feel the violence of Tim’s orgasm under her fingers, the sperm being pumped out in great spurts.
“Gosh! It’s so powerful!”
Her eyes widened as she watched the spherical teat inflating, filling with c-um, in front of her face.
“There’s so much…”
Slowly Tim subsided, amidst little satisfied moans.
“Sounds like he enjoyed that,” smirked Candy.
“Look how much c-um he made!”
Candy peered round. The teat was hanging down, heavy with Tim’s first ejaculation. Phillipa squeezed it.
“It’s all squidgy and warm!” she giggled.
“Give him a minute or two, yeah, and we’ll see what he’s got left… Do you want a go with the strap-on?”
“Maybe one go… But I like doing this. It feels so cool when he pops…”
28
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 03, 2025, 08:22:30 AM »
Chapter 257.
Tim never had a chance. Phillipa maintained her grip on his boyhood, knowing that the welfare of that appendage was Tim’s greatest concern, and that he would do nothing to prejudice it. He noticed the addition to the floor at once.
“W-what’s this fing?”
“Think of it as your quiet place, Tim,” said Candy, “a place for little boys who’ve got a bit over-excited and need some time out. Now, before we introduce you to it, let me get you ready.”
She opened the tall cupboard. The appropriate accessories were ready to hand.
“We’ll put your knee-protectors on first, so you’ll be comfortable… There we go. Now thigh straps…so… Wrist cuffs… Good. Now if you like to go down on all fours…”
A gentle tug from Phillipa was all that was required and Tim went down as obediently as a trained dog. The girls attached his wrists and knees to the four ends of the cross, and stood up to survey their work.
“Comfortable?”
“Why am I ‘ere…?”
Candy looked at Phillipa. “Shall I explain it to him? Okay. First reason, you can’t go on living in such frustration, Tim. Look how you are today, just through being close to us. It’s not fair on you. I don’t know what satisfaction you get from Bobby or Jessica, but it’s clearly not enough. Second, we’re tired of you swaggering about outside showing off that erection of yours. Yes, it’s impressive, but it’s sowing dissatisfaction and jealousy amongst the staff. Moreover you have a wedding next weekend, and you need to save all your potency for then. So we’ve decided to help you.”
She reached into the cupboard and pulled out a strap-on - black straps and grey rubber dil-do - and held it in front of his face.
“It’s my turn first with this. You’ll find it much more pleasurable if you go with it instead of trying to resist. Either way it’ll be a new experience, I’m sure.”
Phillipa buckled it on for her. Broad straps around the hips, a slightly narrower one through the crotch. The dil-do, the smooth shaft tapering slightly towards the slightly thicker, blunt head, quivered as Phillipa tightened the buckles.
“Tight as you like, Phillipa… That’s it…”
She showed Tim. He whimpered.
“Please…”
“Oh, you’re begging for it…”
“No… Please don’t…”
“Phillipa? Got that gag?”
“Right here Candy.”
The gag was made of cream latex, a pen-is head one side complete with a tiny central hole, a ball, about the size of a squash ball, the other. At the junction a soft plastic ring with straps attached. Phillipa pushed the pen-is head unceremoniously between his lips, and buckled it up tight at the back of his neck. The ball had a small rubber plug at the top. She pulled it out and used a syringe to fill the ball with condensed milk from a jar. She replaced the plug.
“There. I know you like very sweet things. Enjoy. You may have to suc-k hard to get what you want, but it’ll be good practice, don’t you think?” She giggled.
With Tim effectively silenced, the girls could proceed. They also put on knee-protectors, and while Phillipa knelt down at Tim’s side, Candy rolled a condom over the dil-do, picked up a squeezy bottle of lubricant, and took her place behind him. Phillipa activated the cameras, and they were ready to begin.
Tim never had a chance. Phillipa maintained her grip on his boyhood, knowing that the welfare of that appendage was Tim’s greatest concern, and that he would do nothing to prejudice it. He noticed the addition to the floor at once.
“W-what’s this fing?”
“Think of it as your quiet place, Tim,” said Candy, “a place for little boys who’ve got a bit over-excited and need some time out. Now, before we introduce you to it, let me get you ready.”
She opened the tall cupboard. The appropriate accessories were ready to hand.
“We’ll put your knee-protectors on first, so you’ll be comfortable… There we go. Now thigh straps…so… Wrist cuffs… Good. Now if you like to go down on all fours…”
A gentle tug from Phillipa was all that was required and Tim went down as obediently as a trained dog. The girls attached his wrists and knees to the four ends of the cross, and stood up to survey their work.
“Comfortable?”
“Why am I ‘ere…?”
Candy looked at Phillipa. “Shall I explain it to him? Okay. First reason, you can’t go on living in such frustration, Tim. Look how you are today, just through being close to us. It’s not fair on you. I don’t know what satisfaction you get from Bobby or Jessica, but it’s clearly not enough. Second, we’re tired of you swaggering about outside showing off that erection of yours. Yes, it’s impressive, but it’s sowing dissatisfaction and jealousy amongst the staff. Moreover you have a wedding next weekend, and you need to save all your potency for then. So we’ve decided to help you.”
She reached into the cupboard and pulled out a strap-on - black straps and grey rubber dil-do - and held it in front of his face.
“It’s my turn first with this. You’ll find it much more pleasurable if you go with it instead of trying to resist. Either way it’ll be a new experience, I’m sure.”
Phillipa buckled it on for her. Broad straps around the hips, a slightly narrower one through the crotch. The dil-do, the smooth shaft tapering slightly towards the slightly thicker, blunt head, quivered as Phillipa tightened the buckles.
“Tight as you like, Phillipa… That’s it…”
She showed Tim. He whimpered.
“Please…”
“Oh, you’re begging for it…”
“No… Please don’t…”
“Phillipa? Got that gag?”
“Right here Candy.”
The gag was made of cream latex, a pen-is head one side complete with a tiny central hole, a ball, about the size of a squash ball, the other. At the junction a soft plastic ring with straps attached. Phillipa pushed the pen-is head unceremoniously between his lips, and buckled it up tight at the back of his neck. The ball had a small rubber plug at the top. She pulled it out and used a syringe to fill the ball with condensed milk from a jar. She replaced the plug.
“There. I know you like very sweet things. Enjoy. You may have to suc-k hard to get what you want, but it’ll be good practice, don’t you think?” She giggled.
With Tim effectively silenced, the girls could proceed. They also put on knee-protectors, and while Phillipa knelt down at Tim’s side, Candy rolled a condom over the dil-do, picked up a squeezy bottle of lubricant, and took her place behind him. Phillipa activated the cameras, and they were ready to begin.
29
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by BabyJay on November 03, 2025, 04:40:56 AM »
Delightful. Sounds like the 4 'Little Sisters' are going to be taught how to bring out their feminine sides with pretty dresses and cute frilly knickers or regulation school knickers as well as make up and manicures. Looking forward to continuation.
30
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on November 02, 2025, 09:19:56 PM »
Meet the Big Sisters
The next afternoon, Madison gathered the boys in one of the smaller rooms of the house and introduced them to their new mentors—sorority “Big Sisters” charged with guiding their journeys. The power dynamics were established right off the bat, and it was clear the Big Sisters were in charge. Nate was paired with Cassidy, a fashionista with a dazzling smile and a penchant for pep talks. Milo met Tara, Gamma Delta’s resident prankster, who appeared to see through his false bravado immediately. She looked as though she’d take nothing at face value and would not hesitate to keep him in line. Julian was assigned to Elise, a patient artist with an eye for style. She looked him over with appraising eyes, already seeming to envision changes. Owen, still bristling, found himself under Brianna’s supervision. As he would soon learn, her no-nonsense attitude rivaled his own. Her piercing stare seemed to dare him to defy her.
The Big Sisters quickly set aside the vague euphemisms Madison had used the day before. They made it clear that dresses, panties and many feminine things would become their new reality. Embarrassment bloomed as the sisters began to explain some of the month’s schedule. Lessons in clothing, makeup and deportment loomed. The confident sorority girls began detailing a list of mandatory requirements and activities the new “Little Sisters” would complete. Any illusions the freshmen boys held about how easy this would be were instantly shattered. The boys shifted uncomfortably as reality sank in.
Madison, acting as though this was exactly what she’d described the day before, advised them condescendingly, “I think you’ll find the best thing to do is just follow instructions, but I’m sure some of you may have to learn the hard way.”
Tara explained further, “Now on weekdays, you’ll keep up with your classes and studies, but don’t think you’ll be slacking off. You’ll need to manage your time wisely, and you’ll be checking in with us all the time.” She went on, “Of course, as your Big Sisters, we are here to help, so on Tuesdays and Thursdays you’ll have mandatory study halls here with us at the house so we can keep you on track… starting tonight." She continued, “and that’s also when you’ll get to learn all about Gamma Delta… you know… our history, our founding members, dates, names and other important facts.” She chuckled, “We’ll have little impromptu quizzes all the time to give you chances to earn more points. You’ll be at 1000 before you know it!” Her cheerful delivery only made the boys feel more out of their element, like schoolchildren sent to the principal’s office.
Cassidy interjected, “Rest assured, we’ll keep close tabs on you even when you’re not at the house.” she continued, her voice tinged with humor and authority, “But be sure to clear your weekend calendars, boys, because Saturdays and Sundays are reserved for us—and trust me, you’re going to be busy!”
Elise chimed in, her words soft but firm, “Every Sunday, we’ll have an exciting contest to cap off the week. I promise it’ll be wonderful fun! You’ll get more details as we go along—but you’ll want to bring your A-games.” Her description of “wonderful fun” felt ominous. None of the boys thought they would enjoy her idea of “wonderful fun.”
Then Madison warned, “But slipups and lack of effort will cost you points. We’re strict, but fair. And we do want you to succeed.” Then she pointed out a whiteboard hanging in the parlor with all their names on it, “But you’ll need to catch on quickly, or the scoreboard won’t be kind.” The boys each stared at their own names posted in glittery pink letters, dread settling in their stomachs.
The implications were obvious—their progress and missteps would be on public display. An uneasy silence settled over the boys. Everything suddenly felt more real, and their nervous faces showed it. As the increasingly worried boys listened, their Big Sisters continued to lay out expectations that seemed to multiply by the minute.
The next afternoon, Madison gathered the boys in one of the smaller rooms of the house and introduced them to their new mentors—sorority “Big Sisters” charged with guiding their journeys. The power dynamics were established right off the bat, and it was clear the Big Sisters were in charge. Nate was paired with Cassidy, a fashionista with a dazzling smile and a penchant for pep talks. Milo met Tara, Gamma Delta’s resident prankster, who appeared to see through his false bravado immediately. She looked as though she’d take nothing at face value and would not hesitate to keep him in line. Julian was assigned to Elise, a patient artist with an eye for style. She looked him over with appraising eyes, already seeming to envision changes. Owen, still bristling, found himself under Brianna’s supervision. As he would soon learn, her no-nonsense attitude rivaled his own. Her piercing stare seemed to dare him to defy her.
The Big Sisters quickly set aside the vague euphemisms Madison had used the day before. They made it clear that dresses, panties and many feminine things would become their new reality. Embarrassment bloomed as the sisters began to explain some of the month’s schedule. Lessons in clothing, makeup and deportment loomed. The confident sorority girls began detailing a list of mandatory requirements and activities the new “Little Sisters” would complete. Any illusions the freshmen boys held about how easy this would be were instantly shattered. The boys shifted uncomfortably as reality sank in.
Madison, acting as though this was exactly what she’d described the day before, advised them condescendingly, “I think you’ll find the best thing to do is just follow instructions, but I’m sure some of you may have to learn the hard way.”
Tara explained further, “Now on weekdays, you’ll keep up with your classes and studies, but don’t think you’ll be slacking off. You’ll need to manage your time wisely, and you’ll be checking in with us all the time.” She went on, “Of course, as your Big Sisters, we are here to help, so on Tuesdays and Thursdays you’ll have mandatory study halls here with us at the house so we can keep you on track… starting tonight." She continued, “and that’s also when you’ll get to learn all about Gamma Delta… you know… our history, our founding members, dates, names and other important facts.” She chuckled, “We’ll have little impromptu quizzes all the time to give you chances to earn more points. You’ll be at 1000 before you know it!” Her cheerful delivery only made the boys feel more out of their element, like schoolchildren sent to the principal’s office.
Cassidy interjected, “Rest assured, we’ll keep close tabs on you even when you’re not at the house.” she continued, her voice tinged with humor and authority, “But be sure to clear your weekend calendars, boys, because Saturdays and Sundays are reserved for us—and trust me, you’re going to be busy!”
Elise chimed in, her words soft but firm, “Every Sunday, we’ll have an exciting contest to cap off the week. I promise it’ll be wonderful fun! You’ll get more details as we go along—but you’ll want to bring your A-games.” Her description of “wonderful fun” felt ominous. None of the boys thought they would enjoy her idea of “wonderful fun.”
Then Madison warned, “But slipups and lack of effort will cost you points. We’re strict, but fair. And we do want you to succeed.” Then she pointed out a whiteboard hanging in the parlor with all their names on it, “But you’ll need to catch on quickly, or the scoreboard won’t be kind.” The boys each stared at their own names posted in glittery pink letters, dread settling in their stomachs.
The implications were obvious—their progress and missteps would be on public display. An uneasy silence settled over the boys. Everything suddenly felt more real, and their nervous faces showed it. As the increasingly worried boys listened, their Big Sisters continued to lay out expectations that seemed to multiply by the minute.
The more you give, the more I can give back.
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Site for: Sissy Stories, ABDL Stories, Sissy Art, Crossdressing, Transgender