Recent Posts
1
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Today at 05:22:50 AM »
Chapter 394.
It was a very pretty village, and they spent nearly an hour just wandering around the streets looking at the houses and cottages, and standing on the old bridge watching the river flow sluggishly by. Tim attracted quite a bit of attention, and as is customary in these rural communities, a number of people stopped them to say hello and ask if they needed directions, or if they liked the village, or what they thought of the weather – all a pretext for getting a closer look at Tim.
“Oh, that’s such a pretty outfit,” exclaimed one woman. “So nice to see a young man not dressed in a T-shirt and old jeans! I wish I could get my son to wear something like that. He insists on wearing his most worn-out clothes, he lays about all day and then disappears half the night! He barely talks to me. He’s either looking at his phone, or talking to his girlfriend – his “gf” he calls her. He can’t get a job. Then there’s not much here… I swear he’ll be the death of me…”
She rattled on a bit more, until Connie raised a hand. She pulled out an ESDS card and handed it to the woman.
“Give these people a call. If he’s good-looking enough, he may be qualified to be a male model, or even get some regular employment. Send him for an interview and assessment. If he’s lucky he may get a contract.”
“Oh, really? Thank you so much! I can’t wait to tell Paul – that’s his name. He is good looking… Well, that’s a mother’s opinion, of course. He has lovely curly blond hair.”
“Sounds like the perfect material,” smiled Connie. “Mention my name – Connie Brookshaw - and they’ll fast-track him.”
“Connie Brookshaw… I shall. Thank you so much, Ms Brookshaw. May I take a photo of your, er…”
“My nephew. Certainly. But don’t show it to your son, will you? He may not appreciate the finer points of couture.”
“No, right… By the way, he’s nothing to do with Penny of Penny’s Pantry, is he?”
“Oh, yes. Maria sponsored him. We’re going there later this morning.”
“Oh, really? Maybe I’ll see you. My friend and I usually pop in for a coffee…”
“Maybe later, then…”
“Do you think she will? Persuade her son, I mean…” asked Frieda.
“Oh, I hope so. Maybe ESDS should put up a recruitment poster here. Maybe in Penny’s…”
They strolled on along the main street. A woman had stopped to stare and her daughter was pointing at Tim.
“Mummy – look. That boy’s wearing a dress!”
“Yes, darling… I can see…”
“Oh, look!” cried Bridget. “This is the village museum someone mentioned. Let’s go in.” She peered through the door. “It’s quite busy though…”
“All the better,” said Connie. “Come on, Tim…”
He shook his head and made a protesting grunt. But Connie was in no mood for sulks, and gave him a smart slap on his behind.
The museum was full of old things, Roman glass, Roman coins, old farm implements, and so on. Tim attracted more attention than the exhibits, and generated quite a lot a giggles and suppressed laughter. So by the time thy left, and made their way to Penny’s Pantry, he was in quite a bad mood.
Penny’s was a cheerful little place, and quite busy. There arrival was accompanied by gasps and suppressed squeals. Connie introduced Tim to Maria, a cheerful woman in her thirties, who greeted him so warmly that it was impossible for him to remain grumpy.
“You’re even more handsome than in your picture!” Maria exclaimed, in that embarrassing way women have. “Ladies, why don’t you take a seat while I have a word with Tim.”
They sat at the only free table, while Maria took Tim by the arm and drew him behind the counter.
“Tim, would you do me a favour? I have no waitress today. Could you possibly…? All you have to do is take stuff to whichever table I tell you. They’re all numbered. It’s easy. I’ll pay you, of course.”
As Tim couldn’t reply, every request made of him could be taken as answered in the affirmative.
“Thank you so much. I’ll just do the ladies drinks…”
He delivered the drinks without mishap. He could feel every eye in the place focussed on him. There was a murmur of conversation, punctuated by giggles. Several people passing in the street also stopped to stare. He was soon busy delivering drinks and food. As he brought the ladies a plate of pastries, the woman behind him murmured, “that’s such a cute outfit…”
He placed the plate on the table. “Thank you, Popsi!” grinned Frieda. They were enjoying themselves hugely. It wasn’t fair!
It was a very pretty village, and they spent nearly an hour just wandering around the streets looking at the houses and cottages, and standing on the old bridge watching the river flow sluggishly by. Tim attracted quite a bit of attention, and as is customary in these rural communities, a number of people stopped them to say hello and ask if they needed directions, or if they liked the village, or what they thought of the weather – all a pretext for getting a closer look at Tim.
“Oh, that’s such a pretty outfit,” exclaimed one woman. “So nice to see a young man not dressed in a T-shirt and old jeans! I wish I could get my son to wear something like that. He insists on wearing his most worn-out clothes, he lays about all day and then disappears half the night! He barely talks to me. He’s either looking at his phone, or talking to his girlfriend – his “gf” he calls her. He can’t get a job. Then there’s not much here… I swear he’ll be the death of me…”
She rattled on a bit more, until Connie raised a hand. She pulled out an ESDS card and handed it to the woman.
“Give these people a call. If he’s good-looking enough, he may be qualified to be a male model, or even get some regular employment. Send him for an interview and assessment. If he’s lucky he may get a contract.”
“Oh, really? Thank you so much! I can’t wait to tell Paul – that’s his name. He is good looking… Well, that’s a mother’s opinion, of course. He has lovely curly blond hair.”
“Sounds like the perfect material,” smiled Connie. “Mention my name – Connie Brookshaw - and they’ll fast-track him.”
“Connie Brookshaw… I shall. Thank you so much, Ms Brookshaw. May I take a photo of your, er…”
“My nephew. Certainly. But don’t show it to your son, will you? He may not appreciate the finer points of couture.”
“No, right… By the way, he’s nothing to do with Penny of Penny’s Pantry, is he?”
“Oh, yes. Maria sponsored him. We’re going there later this morning.”
“Oh, really? Maybe I’ll see you. My friend and I usually pop in for a coffee…”
“Maybe later, then…”
“Do you think she will? Persuade her son, I mean…” asked Frieda.
“Oh, I hope so. Maybe ESDS should put up a recruitment poster here. Maybe in Penny’s…”
They strolled on along the main street. A woman had stopped to stare and her daughter was pointing at Tim.
“Mummy – look. That boy’s wearing a dress!”
“Yes, darling… I can see…”
“Oh, look!” cried Bridget. “This is the village museum someone mentioned. Let’s go in.” She peered through the door. “It’s quite busy though…”
“All the better,” said Connie. “Come on, Tim…”
He shook his head and made a protesting grunt. But Connie was in no mood for sulks, and gave him a smart slap on his behind.
The museum was full of old things, Roman glass, Roman coins, old farm implements, and so on. Tim attracted more attention than the exhibits, and generated quite a lot a giggles and suppressed laughter. So by the time thy left, and made their way to Penny’s Pantry, he was in quite a bad mood.
Penny’s was a cheerful little place, and quite busy. There arrival was accompanied by gasps and suppressed squeals. Connie introduced Tim to Maria, a cheerful woman in her thirties, who greeted him so warmly that it was impossible for him to remain grumpy.
“You’re even more handsome than in your picture!” Maria exclaimed, in that embarrassing way women have. “Ladies, why don’t you take a seat while I have a word with Tim.”
They sat at the only free table, while Maria took Tim by the arm and drew him behind the counter.
“Tim, would you do me a favour? I have no waitress today. Could you possibly…? All you have to do is take stuff to whichever table I tell you. They’re all numbered. It’s easy. I’ll pay you, of course.”
As Tim couldn’t reply, every request made of him could be taken as answered in the affirmative.
“Thank you so much. I’ll just do the ladies drinks…”
He delivered the drinks without mishap. He could feel every eye in the place focussed on him. There was a murmur of conversation, punctuated by giggles. Several people passing in the street also stopped to stare. He was soon busy delivering drinks and food. As he brought the ladies a plate of pastries, the woman behind him murmured, “that’s such a cute outfit…”
He placed the plate on the table. “Thank you, Popsi!” grinned Frieda. They were enjoying themselves hugely. It wasn’t fair!
2
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Today at 03:13:35 AM »
Chapter 393.
“Now, are you going to behave? Or do I have to get my whip out? That’s better. What do you think of those pretty gloves? Gorgeous, aren’t they? Hold them up so we can see them. That’s it. There, they really are just the perfect finishing touch, don’t you think? What was that, Tim?”
With his new ball gag, poor Tim could do little more than grunt. Excellent, thought Connie. She’d be able to tease him mercilessly all day. And for punishments she’d think about some special mitts so he wouldn’t be able to pull at anything – or even pleasure himself properly! How amusing. This evening she’d update Cassandra. She’d loved the videos. Everyone at ESDS had. If Tim knew they were going to be available to subscribers… She smiled to herself. Well, it was his fault for being so cute, for being such a show-off, and being such an easy dupe.
“Well, we might as well get going. We’ll be early, but we can have a nice walk round the village first. It’s very pretty. Looks olde-worldy, but there’s plenty of money there, take it from me, girls. Anyway…”
They got there coats and headed for the door. Tim was having to be cajoled along. Finally Connie got him outside. She had to accompany him to the car, and return to shut the door.
“What a fuss!” she murmured as she went down the path for the second time. “But once we’re there, he won’t have any choice…”
“Now, are you going to behave? Or do I have to get my whip out? That’s better. What do you think of those pretty gloves? Gorgeous, aren’t they? Hold them up so we can see them. That’s it. There, they really are just the perfect finishing touch, don’t you think? What was that, Tim?”
With his new ball gag, poor Tim could do little more than grunt. Excellent, thought Connie. She’d be able to tease him mercilessly all day. And for punishments she’d think about some special mitts so he wouldn’t be able to pull at anything – or even pleasure himself properly! How amusing. This evening she’d update Cassandra. She’d loved the videos. Everyone at ESDS had. If Tim knew they were going to be available to subscribers… She smiled to herself. Well, it was his fault for being so cute, for being such a show-off, and being such an easy dupe.
“Well, we might as well get going. We’ll be early, but we can have a nice walk round the village first. It’s very pretty. Looks olde-worldy, but there’s plenty of money there, take it from me, girls. Anyway…”
They got there coats and headed for the door. Tim was having to be cajoled along. Finally Connie got him outside. She had to accompany him to the car, and return to shut the door.
“What a fuss!” she murmured as she went down the path for the second time. “But once we’re there, he won’t have any choice…”
3
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Yesterday at 05:32:38 PM »
Chapter 392.
But the look in Tim’s sad little eyes was too much even for Connie.
“Ah, don’t look so miserable, Tim. Actually there’s been a change of plan. We’ll postpone houseboy duties for a day or two. I was chatting to my friend Maria this morning – she runs a little café in Bowersford village, just up the road. Well, I guess “café” isn’t the right word. She calls it a teashop. Penny’s Pantry – named after her mum, who started it. It’s quite twee. Attracts all the women from the area – somewhere they can sit and drink tea and exchange gossip for hours on end. This may be a small, out-of-the-way place, but gossip seems to proliferate in inverse proportion to the population. Anyway, she’s invited us along. We’ll go in the morning. According to the forecast it’s going to be a nice day. It’s still really mild for the time of year. Afterwards we could go on somewhere else. Make a day of it. What do you think?”
Tim nodded slowly. Anything was better than being treated live a slave. He wondered what he would be wearing. Connie seemed to have read his mind.
“When Maria first saw your picture she immediately offered to sponsor you. So she’s paid for your next outfit. So we agreed we’d visit her tomorrow, as Tuesday’s usually a quietish day in the café.”
He looked at her questioningly.
“It’s nice, don’t worry. You’ll like it. No hotpants, though. Lately it seems as though they just make you horny. In fact…”
She took a step back and regarded him critically. She frowned.
“Are you getting horny now? Girls? Am I imagining things, or is he…?”
“Yes! He’s got a little erection!” cried Frieda, delightedly.
Tim clapped his hands to his shorts.
“Not already…” smiled Connie, shaking her head. “Tim, take your hands away, there’s a dear, and let us check.”
Tim shook his head fearfully.
“No? Well, bed time, then. Let’s get you unlocked and ungagged. If you want to play you can do so in your bedroom. I haven’t printed your poster yet, but you’ll find a nice framed piccy of Kit on your bedside cabinet. Oh, you like that, don’t you? Well make sure you don’t oversleep. Breakfast at eight thirty, all right?”
Tuesday morning. Tim slept through his alarm, but Connie playfully flicked water on him till he got up. He was very grumpy, and his mood didn’t improve when she showed him his outfit, a pretty pink latex dress with the words “Penny’s Popsi” across the chest.
“Popsi? What’s a Popsi?”
“It’s a cute girl, Tim. Just like you’re going to be today. Maria’s a good friend, and you’d better not be rude to her.”
“Why do I have to wear all these stupid outfits? And be photographed and videoed? Suppose ESDS really takes off one day. My pictures will be all over the internet.” He had a sudden panic attack. “What about those ones of me…”
“Masturbating? Well, if they ever came out, they would certainly make you famous. Don’t you want to be a celebrity? You’ve always loved attention…”
“Miss. Please. Promise me…”
“No promises, Tim. Just be a good boy, and I’ll look after you… Now, breakfast…”
But Tim wouldn’t let go of his anxiety, and was complaining all through breakfast.
Connie looked at the others. “Time for his new outfit, I’m thinking.”
“Can’t be too soon,” agreed Bridget.
Connie brought it in, the dress, matching shoes and white tights. And his favourite panties. As they helped him into it, he was still mouthing off. Connie fetched the hood which he had worn the day before.
“I’m not wearing that. Not if we’re going out. What will people think?”
Connie sighed. You know what, Tim? I’ve had enough. The only think that seems to keep you in order is a nice fat butt plug. Well, this outfit doesn’t lend itself to that, but we do have a temporary replacement. Today we proceed to the next stage of gag training, with a medium ball. Yesterday was a small. And it’s pink, to match the rest of your outfit. So stand still while we get it on you.”
The ladies were strong, and there were three of them.
“No! Miss! Stop it! Okay…but not the gag, please… Miss…? Mmph…”
Connie tightened the straps of the ball gag and locked his collar. “There. That’s better. Peace at last! Now, stand back over there So I can get a quick snap… Tim! Stop sulking. Stop sulking or else! Thank you. Now a close-up… Good boy!”
But the look in Tim’s sad little eyes was too much even for Connie.
“Ah, don’t look so miserable, Tim. Actually there’s been a change of plan. We’ll postpone houseboy duties for a day or two. I was chatting to my friend Maria this morning – she runs a little café in Bowersford village, just up the road. Well, I guess “café” isn’t the right word. She calls it a teashop. Penny’s Pantry – named after her mum, who started it. It’s quite twee. Attracts all the women from the area – somewhere they can sit and drink tea and exchange gossip for hours on end. This may be a small, out-of-the-way place, but gossip seems to proliferate in inverse proportion to the population. Anyway, she’s invited us along. We’ll go in the morning. According to the forecast it’s going to be a nice day. It’s still really mild for the time of year. Afterwards we could go on somewhere else. Make a day of it. What do you think?”
Tim nodded slowly. Anything was better than being treated live a slave. He wondered what he would be wearing. Connie seemed to have read his mind.
“When Maria first saw your picture she immediately offered to sponsor you. So she’s paid for your next outfit. So we agreed we’d visit her tomorrow, as Tuesday’s usually a quietish day in the café.”
He looked at her questioningly.
“It’s nice, don’t worry. You’ll like it. No hotpants, though. Lately it seems as though they just make you horny. In fact…”
She took a step back and regarded him critically. She frowned.
“Are you getting horny now? Girls? Am I imagining things, or is he…?”
“Yes! He’s got a little erection!” cried Frieda, delightedly.
Tim clapped his hands to his shorts.
“Not already…” smiled Connie, shaking her head. “Tim, take your hands away, there’s a dear, and let us check.”
Tim shook his head fearfully.
“No? Well, bed time, then. Let’s get you unlocked and ungagged. If you want to play you can do so in your bedroom. I haven’t printed your poster yet, but you’ll find a nice framed piccy of Kit on your bedside cabinet. Oh, you like that, don’t you? Well make sure you don’t oversleep. Breakfast at eight thirty, all right?”
Tuesday morning. Tim slept through his alarm, but Connie playfully flicked water on him till he got up. He was very grumpy, and his mood didn’t improve when she showed him his outfit, a pretty pink latex dress with the words “Penny’s Popsi” across the chest.
“Popsi? What’s a Popsi?”
“It’s a cute girl, Tim. Just like you’re going to be today. Maria’s a good friend, and you’d better not be rude to her.”
“Why do I have to wear all these stupid outfits? And be photographed and videoed? Suppose ESDS really takes off one day. My pictures will be all over the internet.” He had a sudden panic attack. “What about those ones of me…”
“Masturbating? Well, if they ever came out, they would certainly make you famous. Don’t you want to be a celebrity? You’ve always loved attention…”
“Miss. Please. Promise me…”
“No promises, Tim. Just be a good boy, and I’ll look after you… Now, breakfast…”
But Tim wouldn’t let go of his anxiety, and was complaining all through breakfast.
Connie looked at the others. “Time for his new outfit, I’m thinking.”
“Can’t be too soon,” agreed Bridget.
Connie brought it in, the dress, matching shoes and white tights. And his favourite panties. As they helped him into it, he was still mouthing off. Connie fetched the hood which he had worn the day before.
“I’m not wearing that. Not if we’re going out. What will people think?”
Connie sighed. You know what, Tim? I’ve had enough. The only think that seems to keep you in order is a nice fat butt plug. Well, this outfit doesn’t lend itself to that, but we do have a temporary replacement. Today we proceed to the next stage of gag training, with a medium ball. Yesterday was a small. And it’s pink, to match the rest of your outfit. So stand still while we get it on you.”
The ladies were strong, and there were three of them.
“No! Miss! Stop it! Okay…but not the gag, please… Miss…? Mmph…”
Connie tightened the straps of the ball gag and locked his collar. “There. That’s better. Peace at last! Now, stand back over there So I can get a quick snap… Tim! Stop sulking. Stop sulking or else! Thank you. Now a close-up… Good boy!”
4
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 14, 2026, 04:21:22 AM »
Tim may not be feeling quite so impatient, RibbonBound...
5
Active Sissy Stories / Re: His Aunt Nicole
« Last post by RibbonBound on August 13, 2026, 06:39:46 PM »
Oh my! This is getting so good!!! The manipulation and gaslighting is top notch. And Timmy in his little 'Piggy Pageboy' outfit! Perfection! You are just so delightfully creative! Can't wait for the next chapter!
6
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 12, 2026, 06:35:05 PM »
Chapter 391.
For a moment there was no reply – only a faint sniffling sound. Then,
“Oh… Miss Brookshaw… Yes, thank you. I…” But she collapsed in giggles.
“What do you think?”
“He… Haha, he looks so cute… Tim, you look… It suits you perfectly. Now I have a new pet name for you… My little piggy…. Hahaha…”
Jenny had been slightly suspicious her so-called boyfriend might have been flirting with members of the staff. These pictures had totally reassured her. Tim himself, however, was not so amused.
“It’s just one outfit, Jenny. It’s supposed to be a joke, see?”
“Is that why you’re chained up?”
“No… That’s just…”
“Because he has trouble staying in one place,” laughed Connie. “I could send pics of some of the other outfits if you’re interested…”
“No!”
“Miss Brookshaw? I’d love any pictures you can spare… That aren’t secret, you know…”
“I’ll see what I can do, Jenny. We’ve rather overrun for now. Do you need another minute or two with Tim?”
“No, that’s all right. I need to transfer these onto my laptop so I can see them in their full glory…”
“Of course. Goodbye for now, Jenny. Sorry about tonight. I’ll make sure he isn’t late tomorrow. Maybe you should have a video call to make up…”
Tim was furious, but also afraid too afraid of Connie to express his anger, so he resorted to whining.
“Miss… Why did you do that… What will Jenny think…? I look like an idiot…”
“You look like what you are… Pageboy Piggy. I’m sure she’ll love you all the more for being so sweet. If she does think you’re a fool, it’s your own fault.”
“How is it my fault?”
“You really don’t get it, do you. If you’d smiled and made a joke of it, she would have thought you were being a good sport. But no, you had to get all embarrassed, blushing and wriggling like a little kid caught getting up to mischief.”
Tim realised she was quite right, but still couldn’t bring himself to admit it.
“You had no right… You shouldn’t mess with my relationship like that. You shouldn’t even have been listening in to my private phone conversation…”
“Mess with your relationship?” Connie gave a cynical laugh. “After you’ve spent the last couple of days smooching with Kit? Are you for real? I’m fed up with this. I’m fed up with your whining. Fortunately I’ve got the perfect thing to put a stop to it.”
She pulled the latex hood out of the bag, strode over to him, and, ignoring his protests, and thrust it over his head. She had to unlock and remove his collar temporarily to roll down the neck. It fitted him perfectly. Once neatly in place, she thrust the rubber ball unceremoniously into his mouth, and buckled up the mouth strap. She stood back. He was trying to speak, but could only make an inarticulate moaning sound. She took out her phone and took a snap.
You look so funny with that indignant look on your face. Is diddums cross? Is piggy disgruntled? Disgruntled – get it? Oh, I love it.”
“All he needs is a little snout…” added Bridget.
“Yes! Piggy’s first ball-gag!” taunted Connie. “Don’t worry – there’ll be plenty more!”
She took a close-up of his surprised, helpless face.
“I bet Jenny would love this one…”
He shook his head vigorously, and made muffled pleading noises.
“That’s it – beg for mercy. You’ve had it too easy, master Timothy. It’s going to get harder from now on, though… Right girls?”
“Right!” They chorused.
For a moment there was no reply – only a faint sniffling sound. Then,
“Oh… Miss Brookshaw… Yes, thank you. I…” But she collapsed in giggles.
“What do you think?”
“He… Haha, he looks so cute… Tim, you look… It suits you perfectly. Now I have a new pet name for you… My little piggy…. Hahaha…”
Jenny had been slightly suspicious her so-called boyfriend might have been flirting with members of the staff. These pictures had totally reassured her. Tim himself, however, was not so amused.
“It’s just one outfit, Jenny. It’s supposed to be a joke, see?”
“Is that why you’re chained up?”
“No… That’s just…”
“Because he has trouble staying in one place,” laughed Connie. “I could send pics of some of the other outfits if you’re interested…”
“No!”
“Miss Brookshaw? I’d love any pictures you can spare… That aren’t secret, you know…”
“I’ll see what I can do, Jenny. We’ve rather overrun for now. Do you need another minute or two with Tim?”
“No, that’s all right. I need to transfer these onto my laptop so I can see them in their full glory…”
“Of course. Goodbye for now, Jenny. Sorry about tonight. I’ll make sure he isn’t late tomorrow. Maybe you should have a video call to make up…”
Tim was furious, but also afraid too afraid of Connie to express his anger, so he resorted to whining.
“Miss… Why did you do that… What will Jenny think…? I look like an idiot…”
“You look like what you are… Pageboy Piggy. I’m sure she’ll love you all the more for being so sweet. If she does think you’re a fool, it’s your own fault.”
“How is it my fault?”
“You really don’t get it, do you. If you’d smiled and made a joke of it, she would have thought you were being a good sport. But no, you had to get all embarrassed, blushing and wriggling like a little kid caught getting up to mischief.”
Tim realised she was quite right, but still couldn’t bring himself to admit it.
“You had no right… You shouldn’t mess with my relationship like that. You shouldn’t even have been listening in to my private phone conversation…”
“Mess with your relationship?” Connie gave a cynical laugh. “After you’ve spent the last couple of days smooching with Kit? Are you for real? I’m fed up with this. I’m fed up with your whining. Fortunately I’ve got the perfect thing to put a stop to it.”
She pulled the latex hood out of the bag, strode over to him, and, ignoring his protests, and thrust it over his head. She had to unlock and remove his collar temporarily to roll down the neck. It fitted him perfectly. Once neatly in place, she thrust the rubber ball unceremoniously into his mouth, and buckled up the mouth strap. She stood back. He was trying to speak, but could only make an inarticulate moaning sound. She took out her phone and took a snap.
You look so funny with that indignant look on your face. Is diddums cross? Is piggy disgruntled? Disgruntled – get it? Oh, I love it.”
“All he needs is a little snout…” added Bridget.
“Yes! Piggy’s first ball-gag!” taunted Connie. “Don’t worry – there’ll be plenty more!”
She took a close-up of his surprised, helpless face.
“I bet Jenny would love this one…”
He shook his head vigorously, and made muffled pleading noises.
“That’s it – beg for mercy. You’ve had it too easy, master Timothy. It’s going to get harder from now on, though… Right girls?”
“Right!” They chorused.
7
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 12, 2026, 07:13:21 AM »
Chapter 390.
The particular item Connie had in mind was the first resort when dealing with a complainer. It was true that Tim had hardly ever complained, but Connie had become impatient with indulging him, and had been looking for an excuse to apply some punishment. After all there was only a few days left in the session, and she’d hardly made him squirm so far. This was not her usual practice. The arrival of Kit had rather changed the dynamics in Tim’s favour. But she was determined to reverse the trend.
She was rummaging through one of the drawers in one of the cabinets in one of the spare rooms. There was a lot of interesting equipment stored in that farmhouse, and in its cold, gloomy cellars.
“Ah. Here we are.”
She pulled out a small sealed black plastic bag, opened it, and drew forth a piece of folded pink latex. She unfolded it and held it up.
“It should fit. I’ll make it fit if necessary.”
The object in question was a smooth whole-head rubber helmet, open-faced, with a black leather strap at the level of the mouth, and a black ball-gag. She also fingered a pink leather head-harness and ball-gag lying in the drawer.
“That would be nice too, but all in good time. He’ll look pretty in this today.”
She replaced the hood in its bag, closed the drawer, and went to leave. As she did so, she heard a phone ringing in an adjacent room.
“That’s not mine… Goodness!”
She looked at her watch. Almost a quarter to ten!
“I completely forgot about Jenny! We were so carried away…”
She hurried to the spare room where she had hidden Tim’s phone. It was on charge. She picked it up.
“Jenny? I’m so sorry! Tim was a bit tied up, and the photo session overran… I’ll get him right away. Are you well? Good…that’s nice…oh, really? Tim? He’s fine, yes. Working hard. Today? Oh, a long session, yes. But great fun. He really makes an excellent model. He is, yes. A fine figure of a boy… Well, not a boy any more. To us oldies he seems just a boy…”
She had made it back to the living room.
“Ah, Tim. There you are!” (As if he could be anywhere else.) “It’s Jenny. I’m sorry, we were so busy I completely forgot.”
Tim, alarmed, stated shaking his head vigorously. But Connie had seen the humour of the situation. She went to give him the phone, but changed her mind. Instead she put it on speaker and placed it on the coffee table out of his reach.
“Say hi, Tim. We’ll leave you to chat. Fifteen minutes, don’t forget…”
She gave the others a warning glance, finger to lips, and quietly took her seat. Tim was furious, but couldn’t say anything.
“Tim? Are you there?”
“Oh… Yeah. H-hi, Jenny… H-how are you?”
“You couldn’t ring me on time… You must have been busy.”
“Oh…yeah…sorry. We were right in the middle of a project…”
“What project was that? What about?”
“Oh, you know…”
“No, I don’t. That’s why I’m asking.” Jenny sounded slightly irritated.
“Er… oh, just a new outfit…” Tim was a useless liar. He reverted to diluted truth. “Just, you know, pageboy stuff…”
“A new pageboy outfit? What’s it like?”
“I’m, er, not supposed to say…” He glared at his tormentors, struggling to smother their mirth.
“What, you can’t even tell me that? Surely it can’t be that big a trade secret.”
Tim was struggling now. “You know how it is… I’m not allowed… Miss is very strict…”
“Have you finished?”
Tim was desperate to get off the phone. “No. Nearly, though. Just a few more shots. So I can’t talk for long…”
“Ooh. Can I have a little peep? We could have a video call – or just send me a photo? Promise I won’t tell…”
“No, I said I can’t…”
“Ask Ms Brookshaw. Maybe she wouldn’t mind…”
Connie seized the opportunity. “Tim? Did someone mention my name?” she called, as if from a distance.
“No, it’s all right…” he replied, in a panic.
“It was me,” said Jenny as loud as she could. “Are you there, Ms Brookshaw?”
“Oh, hi Jenny. Yes, I’m right here. What was it you wanted?”
Tim was madly shaking his head, pleading with his eyes. Connie ignored him.
“I was just asking Tim if I could have a sneak peek at the uniform he’s modelling…”
“Oh, is that all? Of course, dear. Here, I’ll send you a snap…”
She picked up the phone and prepared to take his picture.
“No! Miss, please…” whined Tim. But to no avail.
“Done. Now turn round and show Jenny your cute little tail…”
“Miss…”
“Or else…”
He obeyed.
“There. Did you get those, Jenny?”
The particular item Connie had in mind was the first resort when dealing with a complainer. It was true that Tim had hardly ever complained, but Connie had become impatient with indulging him, and had been looking for an excuse to apply some punishment. After all there was only a few days left in the session, and she’d hardly made him squirm so far. This was not her usual practice. The arrival of Kit had rather changed the dynamics in Tim’s favour. But she was determined to reverse the trend.
She was rummaging through one of the drawers in one of the cabinets in one of the spare rooms. There was a lot of interesting equipment stored in that farmhouse, and in its cold, gloomy cellars.
“Ah. Here we are.”
She pulled out a small sealed black plastic bag, opened it, and drew forth a piece of folded pink latex. She unfolded it and held it up.
“It should fit. I’ll make it fit if necessary.”
The object in question was a smooth whole-head rubber helmet, open-faced, with a black leather strap at the level of the mouth, and a black ball-gag. She also fingered a pink leather head-harness and ball-gag lying in the drawer.
“That would be nice too, but all in good time. He’ll look pretty in this today.”
She replaced the hood in its bag, closed the drawer, and went to leave. As she did so, she heard a phone ringing in an adjacent room.
“That’s not mine… Goodness!”
She looked at her watch. Almost a quarter to ten!
“I completely forgot about Jenny! We were so carried away…”
She hurried to the spare room where she had hidden Tim’s phone. It was on charge. She picked it up.
“Jenny? I’m so sorry! Tim was a bit tied up, and the photo session overran… I’ll get him right away. Are you well? Good…that’s nice…oh, really? Tim? He’s fine, yes. Working hard. Today? Oh, a long session, yes. But great fun. He really makes an excellent model. He is, yes. A fine figure of a boy… Well, not a boy any more. To us oldies he seems just a boy…”
She had made it back to the living room.
“Ah, Tim. There you are!” (As if he could be anywhere else.) “It’s Jenny. I’m sorry, we were so busy I completely forgot.”
Tim, alarmed, stated shaking his head vigorously. But Connie had seen the humour of the situation. She went to give him the phone, but changed her mind. Instead she put it on speaker and placed it on the coffee table out of his reach.
“Say hi, Tim. We’ll leave you to chat. Fifteen minutes, don’t forget…”
She gave the others a warning glance, finger to lips, and quietly took her seat. Tim was furious, but couldn’t say anything.
“Tim? Are you there?”
“Oh… Yeah. H-hi, Jenny… H-how are you?”
“You couldn’t ring me on time… You must have been busy.”
“Oh…yeah…sorry. We were right in the middle of a project…”
“What project was that? What about?”
“Oh, you know…”
“No, I don’t. That’s why I’m asking.” Jenny sounded slightly irritated.
“Er… oh, just a new outfit…” Tim was a useless liar. He reverted to diluted truth. “Just, you know, pageboy stuff…”
“A new pageboy outfit? What’s it like?”
“I’m, er, not supposed to say…” He glared at his tormentors, struggling to smother their mirth.
“What, you can’t even tell me that? Surely it can’t be that big a trade secret.”
Tim was struggling now. “You know how it is… I’m not allowed… Miss is very strict…”
“Have you finished?”
Tim was desperate to get off the phone. “No. Nearly, though. Just a few more shots. So I can’t talk for long…”
“Ooh. Can I have a little peep? We could have a video call – or just send me a photo? Promise I won’t tell…”
“No, I said I can’t…”
“Ask Ms Brookshaw. Maybe she wouldn’t mind…”
Connie seized the opportunity. “Tim? Did someone mention my name?” she called, as if from a distance.
“No, it’s all right…” he replied, in a panic.
“It was me,” said Jenny as loud as she could. “Are you there, Ms Brookshaw?”
“Oh, hi Jenny. Yes, I’m right here. What was it you wanted?”
Tim was madly shaking his head, pleading with his eyes. Connie ignored him.
“I was just asking Tim if I could have a sneak peek at the uniform he’s modelling…”
“Oh, is that all? Of course, dear. Here, I’ll send you a snap…”
She picked up the phone and prepared to take his picture.
“No! Miss, please…” whined Tim. But to no avail.
“Done. Now turn round and show Jenny your cute little tail…”
“Miss…”
“Or else…”
He obeyed.
“There. Did you get those, Jenny?”
8
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 11, 2026, 12:46:20 PM »
Chapter 389.
Once out of the shower, Tim presented himself again in the big living-room, which served as his changing room.
“So… What am I modelling next?”
“You’ll be happy. Another pageboy. But this time more of a fun one.”
“Oh? In what way, miss?”
“Here’s the tunic. This might give you a clue.”
“So what’s the difference? Apart from the fact it’s pink? Oh…” He had noticed the legend on the front and back of the tunic. “Piggy Pageboy? What’s with that, miss?”
“Let’s get it on and I’ll explain.”
“Does it have…a posture trainer?”
“Well, of course. It’s a necessity. But this one’s a little more user-friendly. The user being your mistress, naturally… I’ll show you. On the inside…see?”
Protruding from the seat was what appeared to be a plastic cylinder with a spherical tip, not more than four inches long. But it was sheathed in a translucent pink rubber bulb, presently floppy and deflated. On the outside it manifested itself as a little inflated tail. She helped him on with the shorts and pulled them up.
“What’s great about this is that it pops in so easily.” She suited the action to the word. The plug slipped in effortlessly.
“Now let’s zip you up… buckle the belt…so… Now I’ll show you how easily it is to operate. There’s valves on the air intake for the tail, and the interior bulb. So if I squeeze the tail…so…you can feel the bulb inflating, right?”
“Yes…miss… I can…”
“A few good pumps and it’s nice and firm. Yes?”
“No more, miss… Please…”
“Okay. You see the air is forced along the tube and comes out of those little tiny holes just behind the spherical end. The valve prevents it flowing back, so once it’s inflated, I’m afraid there’s no removing it – unless your know the secret method.” She laughed. “Which you don’t. At the same time the tail is designed to keep its shape. Do not upset your mistress when you’re wearing this, or she may be tempted to give it an extra squeeze! Not comfortable! Of course, the plug itself has all the usual pulse and vibe effects, which I can demonstrate…”
“Not now, please miss!”
“Okay. Maybe later then. Come on. You’re ready. Let’s get you back on the maid-tidy.”
He was soon chained into place again. His audience regarded him with satisfaction.
“I don’t understand. What’s this “piggy” thing?”
“Ah. Frieda… Maybe you’d care to explain…”
“Sure. You see, Tim, when Kit was here we were talking about what a wonderful pet you’d make. ESDS are proposing to advertise some of their boys as pets rather than maids. Some women prefer to have a pet. Pets are lucky. They tend to get spoiled, fed well, played with a lot, and so on. All right, they might have to sleep in a kennel or a basket or be kept in a cage, and they have to wear a locking collar and ring so their mistresses can put them on a leash, but you wouldn’t mind that, would you?”
“So that’s what this collar’s for…?
“Yes. Do you like the idea? I’m sure you must. All your mistress has to do is clip on your lead, and then you have to follow her wherever she goes. She can take you to a party, and everyone will say, “oh, what a pretty piggy! Where did you get him? Can I squeeze his tail?” What fun! Kit thought you’d make a pretty puppy. But I immediately thought of a little piglet. Piglets are cute like you, and they squeak and squeal a lot when they get excited – just like you did earlier – and they can get themselves into such a sticky mess too – just like you also did. And it all ends in tears. So it seems my intuition was correct.”
“Turn round and waggle your tail for us,” said Connie.
Tim did as he was instructed.
“So how do you feel about being a piggy pet?”
The plug felt firm enough inside him for Tim to resolve to be as compliant as possible.
“Yes, it sounds okay…”
“Good boy. I’ll make a note to tell Cassandra she can put you in as a maid, pageboy, or pet, yes?”
“Er, yes, I suppose, miss…”
“Well don’t look so miserable about it – unless you want to be hired out as a houseboy, and be forced to do all the dirty, unpleasant tasks…”
“No, of course not. miss,” he blurted, indignantly. That wouldn’t be fair. I’ve been really good. I’ve done everything you’ve asked of me. I’m a fully-trained pageboy! Houseboy? That the pits! I’m sure Miss Cassandra wouldn’t do such a thing…”
“I beg your pardon?” cried Connie, outraged. “Who do you think you are? Do you think you have any rights here? How dare you express an opinion about what you will or won’t do, or what’s fair or unfair. You need a lesson young man.”
She frowned. “Right. Tomorrow you can be our houseboy for the day, so you understand exactly what it means. Yes, it would be good experience for you. You’ll realise just how tolerant we’ve been, and how lucky you were to be sent here. Houseboys are virtually slaves. They even sleep chained up. They wear chastity devices permanently – no relief. And they’re forbidden to speak, let alone answer back. One word and out comes the ball gag. Oh, you know what? I have one piece of houseboy training equipment right to hand. Want to see it? No? Well you’re going to. Don’t move – oh, you can’t, can you? I’ll be right back.”
Once out of the shower, Tim presented himself again in the big living-room, which served as his changing room.
“So… What am I modelling next?”
“You’ll be happy. Another pageboy. But this time more of a fun one.”
“Oh? In what way, miss?”
“Here’s the tunic. This might give you a clue.”
“So what’s the difference? Apart from the fact it’s pink? Oh…” He had noticed the legend on the front and back of the tunic. “Piggy Pageboy? What’s with that, miss?”
“Let’s get it on and I’ll explain.”
“Does it have…a posture trainer?”
“Well, of course. It’s a necessity. But this one’s a little more user-friendly. The user being your mistress, naturally… I’ll show you. On the inside…see?”
Protruding from the seat was what appeared to be a plastic cylinder with a spherical tip, not more than four inches long. But it was sheathed in a translucent pink rubber bulb, presently floppy and deflated. On the outside it manifested itself as a little inflated tail. She helped him on with the shorts and pulled them up.
“What’s great about this is that it pops in so easily.” She suited the action to the word. The plug slipped in effortlessly.
“Now let’s zip you up… buckle the belt…so… Now I’ll show you how easily it is to operate. There’s valves on the air intake for the tail, and the interior bulb. So if I squeeze the tail…so…you can feel the bulb inflating, right?”
“Yes…miss… I can…”
“A few good pumps and it’s nice and firm. Yes?”
“No more, miss… Please…”
“Okay. You see the air is forced along the tube and comes out of those little tiny holes just behind the spherical end. The valve prevents it flowing back, so once it’s inflated, I’m afraid there’s no removing it – unless your know the secret method.” She laughed. “Which you don’t. At the same time the tail is designed to keep its shape. Do not upset your mistress when you’re wearing this, or she may be tempted to give it an extra squeeze! Not comfortable! Of course, the plug itself has all the usual pulse and vibe effects, which I can demonstrate…”
“Not now, please miss!”
“Okay. Maybe later then. Come on. You’re ready. Let’s get you back on the maid-tidy.”
He was soon chained into place again. His audience regarded him with satisfaction.
“I don’t understand. What’s this “piggy” thing?”
“Ah. Frieda… Maybe you’d care to explain…”
“Sure. You see, Tim, when Kit was here we were talking about what a wonderful pet you’d make. ESDS are proposing to advertise some of their boys as pets rather than maids. Some women prefer to have a pet. Pets are lucky. They tend to get spoiled, fed well, played with a lot, and so on. All right, they might have to sleep in a kennel or a basket or be kept in a cage, and they have to wear a locking collar and ring so their mistresses can put them on a leash, but you wouldn’t mind that, would you?”
“So that’s what this collar’s for…?
“Yes. Do you like the idea? I’m sure you must. All your mistress has to do is clip on your lead, and then you have to follow her wherever she goes. She can take you to a party, and everyone will say, “oh, what a pretty piggy! Where did you get him? Can I squeeze his tail?” What fun! Kit thought you’d make a pretty puppy. But I immediately thought of a little piglet. Piglets are cute like you, and they squeak and squeal a lot when they get excited – just like you did earlier – and they can get themselves into such a sticky mess too – just like you also did. And it all ends in tears. So it seems my intuition was correct.”
“Turn round and waggle your tail for us,” said Connie.
Tim did as he was instructed.
“So how do you feel about being a piggy pet?”
The plug felt firm enough inside him for Tim to resolve to be as compliant as possible.
“Yes, it sounds okay…”
“Good boy. I’ll make a note to tell Cassandra she can put you in as a maid, pageboy, or pet, yes?”
“Er, yes, I suppose, miss…”
“Well don’t look so miserable about it – unless you want to be hired out as a houseboy, and be forced to do all the dirty, unpleasant tasks…”
“No, of course not. miss,” he blurted, indignantly. That wouldn’t be fair. I’ve been really good. I’ve done everything you’ve asked of me. I’m a fully-trained pageboy! Houseboy? That the pits! I’m sure Miss Cassandra wouldn’t do such a thing…”
“I beg your pardon?” cried Connie, outraged. “Who do you think you are? Do you think you have any rights here? How dare you express an opinion about what you will or won’t do, or what’s fair or unfair. You need a lesson young man.”
She frowned. “Right. Tomorrow you can be our houseboy for the day, so you understand exactly what it means. Yes, it would be good experience for you. You’ll realise just how tolerant we’ve been, and how lucky you were to be sent here. Houseboys are virtually slaves. They even sleep chained up. They wear chastity devices permanently – no relief. And they’re forbidden to speak, let alone answer back. One word and out comes the ball gag. Oh, you know what? I have one piece of houseboy training equipment right to hand. Want to see it? No? Well you’re going to. Don’t move – oh, you can’t, can you? I’ll be right back.”
9
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 11, 2026, 12:42:08 PM »
Chapter 388.
Connie retreated quietly to her seat, and picked up her glass. Tim dropped all pretence. Staring at the phone, he began to finger the shaft of his erection through the taut latex. The ladies watched, fascinated.
“Interesting technique,” murmured Frieda. He was rolling it back and forth, as if he were kneading a cylinder of plasticine. He slid it about – it must have been lubricating freely for some time - until it was in a comfortable masturbating position, at about forty-five degrees to his zip. He began to massage it with his finger tips, latex squeaking against latex. His breathing was punctuated with little moans of pleasure. The ladies looked at each other and fidgeted in their chairs. Now he was alternating between squeezing it and using a finger against the underside of the glans. His eyes, though half closed, were glued to the phone screen. He began to mumble.
“Kit…I want you so much… My coc-k is so hard, just looking at you…”
At this point Bridget almost choked trying to suppress a fit of giggles. Tim didn’t even notice.
“In a moment…you’ll see…I’m going to do such a big c-um…” He shuddered, and momentarily took his hand off his coc-k… A deep breath…and then he was off again.
“That’s an amazing outfit… What sort of boots are you wearing? I’ll clean them for you every day…twice a day…I’ll do anything you want…please…”
“Ah, now we get to the truth,” whispered Connie. “That is what he really wants. Don’t you think?”
“Yes,” agreed Bridget. “Not only that, but to be her little pet. And from what I’ve seen of Kit, that would really appeal to her…”
And they all sniggered.
“Yes,” grinned Frieda. “I can just see him on a leash…”
Tim was getting perilously near a climax. His fingers worked in a slow cadence, as if he were milking an udder, accompanied by faint juicy ploppings emanating from inside the taut latex. His eyes were half closed now, the hand holding the phone had dropped, and his commentary had subsided into a series of hardly audible groans and squeaks. The right leg band of his shorts slid up and down in time with his movements, and a glistening bead of sticky juice was trickling down his thigh. The ladies were no longer talking, but leaning forward on tenterhooks, waiting for the climax. Tim was right on the edge. He barely dared to touch it now – it was nearly at his hip, like a firm sausage, the latex taut, moulded to its length, twitching of its own accord.
“Go on, Tim,” breathed Bridget, “just let go, silly…”
Let’s give him a hand,” whispered Connie, turning the remote up a couple of notches. That did it. The first sign they had that he had capitulated was when Connie’s phone slipped out of his hand. There was a momentary pause, and then he gasped, shuddered, crossed his thighs, and grabbed the leg frills.
“Oh, gosh! Miss! I’m…ooh….”
The ladies couldn’t suppress their laughter. He was so cute when he came. But he didn’t even notice. His eyes were tight shut. Spasm after spasm ran through him, and c-um streamed down his right leg. Somehow he remained standing. The ladies watched with amusement until the last tremor had died away, and he reopened his eyes. He looked somewhat disoriented. They gave him a little round of applause.
“I-I’m sorry, miss… I didn’t actually mean to…do that…”
“Nonsense, Tim,” said Connie, suppressing her desire to laugh out loud, “that was very impressive. It looked very intense. Was it?”
“Yes… I quite forgot where I was… I was just thinking of…”
“Kit?”
“Y-yes…”
“Well, I think you’ve totally proved yourself.”
“You were amazing,” added Frieda. “You should be proud of yourself.”
Tim smiled faintly. He let go of the slimy leg band and stretched his arms.
“Did I do it well? I really tried. And I didn’t collapse at the end there, though I could have done. Do you think Kit…”
“She’ll be so happy,” said Bridget. “When she sees the video I bet she won’t be able to wait to return.”
They let him preen himself for a few minutes. Connie brought him a drink, put on her rubber gloves – the maid-tidy was a mess - and knelt down to unlock his ankle cuffs.
“We’ll get you cleaned up, then we have time for one more outfit this evening. No more orgasms for you tonight, young man. At least, not before bedtime,” she added, with a wink.
Connie retreated quietly to her seat, and picked up her glass. Tim dropped all pretence. Staring at the phone, he began to finger the shaft of his erection through the taut latex. The ladies watched, fascinated.
“Interesting technique,” murmured Frieda. He was rolling it back and forth, as if he were kneading a cylinder of plasticine. He slid it about – it must have been lubricating freely for some time - until it was in a comfortable masturbating position, at about forty-five degrees to his zip. He began to massage it with his finger tips, latex squeaking against latex. His breathing was punctuated with little moans of pleasure. The ladies looked at each other and fidgeted in their chairs. Now he was alternating between squeezing it and using a finger against the underside of the glans. His eyes, though half closed, were glued to the phone screen. He began to mumble.
“Kit…I want you so much… My coc-k is so hard, just looking at you…”
At this point Bridget almost choked trying to suppress a fit of giggles. Tim didn’t even notice.
“In a moment…you’ll see…I’m going to do such a big c-um…” He shuddered, and momentarily took his hand off his coc-k… A deep breath…and then he was off again.
“That’s an amazing outfit… What sort of boots are you wearing? I’ll clean them for you every day…twice a day…I’ll do anything you want…please…”
“Ah, now we get to the truth,” whispered Connie. “That is what he really wants. Don’t you think?”
“Yes,” agreed Bridget. “Not only that, but to be her little pet. And from what I’ve seen of Kit, that would really appeal to her…”
And they all sniggered.
“Yes,” grinned Frieda. “I can just see him on a leash…”
Tim was getting perilously near a climax. His fingers worked in a slow cadence, as if he were milking an udder, accompanied by faint juicy ploppings emanating from inside the taut latex. His eyes were half closed now, the hand holding the phone had dropped, and his commentary had subsided into a series of hardly audible groans and squeaks. The right leg band of his shorts slid up and down in time with his movements, and a glistening bead of sticky juice was trickling down his thigh. The ladies were no longer talking, but leaning forward on tenterhooks, waiting for the climax. Tim was right on the edge. He barely dared to touch it now – it was nearly at his hip, like a firm sausage, the latex taut, moulded to its length, twitching of its own accord.
“Go on, Tim,” breathed Bridget, “just let go, silly…”
Let’s give him a hand,” whispered Connie, turning the remote up a couple of notches. That did it. The first sign they had that he had capitulated was when Connie’s phone slipped out of his hand. There was a momentary pause, and then he gasped, shuddered, crossed his thighs, and grabbed the leg frills.
“Oh, gosh! Miss! I’m…ooh….”
The ladies couldn’t suppress their laughter. He was so cute when he came. But he didn’t even notice. His eyes were tight shut. Spasm after spasm ran through him, and c-um streamed down his right leg. Somehow he remained standing. The ladies watched with amusement until the last tremor had died away, and he reopened his eyes. He looked somewhat disoriented. They gave him a little round of applause.
“I-I’m sorry, miss… I didn’t actually mean to…do that…”
“Nonsense, Tim,” said Connie, suppressing her desire to laugh out loud, “that was very impressive. It looked very intense. Was it?”
“Yes… I quite forgot where I was… I was just thinking of…”
“Kit?”
“Y-yes…”
“Well, I think you’ve totally proved yourself.”
“You were amazing,” added Frieda. “You should be proud of yourself.”
Tim smiled faintly. He let go of the slimy leg band and stretched his arms.
“Did I do it well? I really tried. And I didn’t collapse at the end there, though I could have done. Do you think Kit…”
“She’ll be so happy,” said Bridget. “When she sees the video I bet she won’t be able to wait to return.”
They let him preen himself for a few minutes. Connie brought him a drink, put on her rubber gloves – the maid-tidy was a mess - and knelt down to unlock his ankle cuffs.
“We’ll get you cleaned up, then we have time for one more outfit this evening. No more orgasms for you tonight, young man. At least, not before bedtime,” she added, with a wink.
10
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 11, 2026, 12:36:54 PM »
Chapter 387.
Not only had Miss Poole been the instigator of Thomasina’s latex outfits, but she had also been instrumental in engineering her mother’s acceptance of them. Lady Middiford had been ambiguous about that first shocking pink catsuit, but by the time Thomasina had graduated to the more provocative cream one, created for Emily Laidlaw’s party by Cynthia, Violet had convinced her that her daughter was merely dressing cool and fashionable, and exploiting her natural beauty. Since then she had taken a motherly interest in her clothes, and frequently took her to Fantastex to review the new lines. And believing that her daughter was dressing in the height of fashion, and all the attention she accrued was born merely of admiration, insisted she travel to and from Pitt’s Wood in her work clothes. And much as Thomasina found stimulation in the scrutiny of others, nevertheless she was eager to find a reliable form of private transport, a little car, or even a motorbike…
Tim had been wondering how Bobby was coping without him. He would have been relieved to know that help was on the way. But at present he had other things on his mind, specifically the photograph on the screen of Connie’s phone. He swallowed.
“Well?”
“W-well?”
“What do you think?”
“Oh…ah, well… She, er, has very good, er, dress sense…”
Connie and the others burst out laughing.
“Shall I tell her that?” asked Connie. “Tim thinks you have very good dress sense? I can text her now…”
“No! No, miss, don’t do that…”
He was trembling slightly as he stared at her phone, and he was blinking nervously. He was still holding his right arm protectively over the right side of his shorts, his fingers gripping the leg frills.
“She sent you a message, too…”
“Sh-she did…?”
“Yes. Would you like to read it?”
“Y-yes please, miss…”
Connie scrolled down. “Here, take the phone.” She pushed it into his free hand. He looked, wide-eyed.
“Hi to Tim! Do you like my party wear? This pic is for you no one els. I want you use it til we meet again. If it make you c-um it mean we shood have sex. Miss Connie will tell me. I hope I see video. xxx”
Tim could hardly believe what he was reading.
“Th-this is really from…Kit?”
“Of course. You know she seriously fancies you, don’t you?”
“So she’s saying…”
“She’s wants you to use her picture until she gets to see you again. To masturbate, silly! She wants you to show her how much you’re missing her.”
Tim stared at her. “She does?”
Connie nodded. It was true. Kit had told her. She had never had sex with a man. She loved her girlfriend. All the men she had met had been too pushy, too dominating, too eager to “invade my body” as she had put it. Her technique was to let them think she was up for it, then abandon them, leaving them no satisfaction except that they could supply themselves. But for her Tim was the sole exception, the polar opposite of all those predators. And it was obvious to her he was a sexy guy. And she wanted a demonstration of his feelings for her.
He stood there staring at the phone in his hand. He looked almost scared of it.
“Well you could wait for the poster, I suppose, but that wouldn’t be very gallant, now would it?”
“Shall I…?”
“Do it, Tim!” cried Frieda.
“Go on! Show Kit how you feel about her!” added Bridget.
He glanced at them, but his gaze quickly returned to the phone. Connie knew they had him. He was technically an adult, but in terms of his sexual predilections he was still a young teenager, for whom a photo of a beautiful woman, especially the very woman he was fixated on, was the perfect substitute for the real thing.
“Okay… I shall…”
Not only had Miss Poole been the instigator of Thomasina’s latex outfits, but she had also been instrumental in engineering her mother’s acceptance of them. Lady Middiford had been ambiguous about that first shocking pink catsuit, but by the time Thomasina had graduated to the more provocative cream one, created for Emily Laidlaw’s party by Cynthia, Violet had convinced her that her daughter was merely dressing cool and fashionable, and exploiting her natural beauty. Since then she had taken a motherly interest in her clothes, and frequently took her to Fantastex to review the new lines. And believing that her daughter was dressing in the height of fashion, and all the attention she accrued was born merely of admiration, insisted she travel to and from Pitt’s Wood in her work clothes. And much as Thomasina found stimulation in the scrutiny of others, nevertheless she was eager to find a reliable form of private transport, a little car, or even a motorbike…
Tim had been wondering how Bobby was coping without him. He would have been relieved to know that help was on the way. But at present he had other things on his mind, specifically the photograph on the screen of Connie’s phone. He swallowed.
“Well?”
“W-well?”
“What do you think?”
“Oh…ah, well… She, er, has very good, er, dress sense…”
Connie and the others burst out laughing.
“Shall I tell her that?” asked Connie. “Tim thinks you have very good dress sense? I can text her now…”
“No! No, miss, don’t do that…”
He was trembling slightly as he stared at her phone, and he was blinking nervously. He was still holding his right arm protectively over the right side of his shorts, his fingers gripping the leg frills.
“She sent you a message, too…”
“Sh-she did…?”
“Yes. Would you like to read it?”
“Y-yes please, miss…”
Connie scrolled down. “Here, take the phone.” She pushed it into his free hand. He looked, wide-eyed.
“Hi to Tim! Do you like my party wear? This pic is for you no one els. I want you use it til we meet again. If it make you c-um it mean we shood have sex. Miss Connie will tell me. I hope I see video. xxx”
Tim could hardly believe what he was reading.
“Th-this is really from…Kit?”
“Of course. You know she seriously fancies you, don’t you?”
“So she’s saying…”
“She’s wants you to use her picture until she gets to see you again. To masturbate, silly! She wants you to show her how much you’re missing her.”
Tim stared at her. “She does?”
Connie nodded. It was true. Kit had told her. She had never had sex with a man. She loved her girlfriend. All the men she had met had been too pushy, too dominating, too eager to “invade my body” as she had put it. Her technique was to let them think she was up for it, then abandon them, leaving them no satisfaction except that they could supply themselves. But for her Tim was the sole exception, the polar opposite of all those predators. And it was obvious to her he was a sexy guy. And she wanted a demonstration of his feelings for her.
He stood there staring at the phone in his hand. He looked almost scared of it.
“Well you could wait for the poster, I suppose, but that wouldn’t be very gallant, now would it?”
“Shall I…?”
“Do it, Tim!” cried Frieda.
“Go on! Show Kit how you feel about her!” added Bridget.
He glanced at them, but his gaze quickly returned to the phone. Connie knew they had him. He was technically an adult, but in terms of his sexual predilections he was still a young teenager, for whom a photo of a beautiful woman, especially the very woman he was fixated on, was the perfect substitute for the real thing.
“Okay… I shall…”
The more you give, the more I can give back.
Website, forum design, software, & security on this site is copyrighted. It was made personally by Betty Pearl, of Betty Pearl's Pubs, Sissy Stories, buffalobetties, pearlcorona. Betty's Pub is a non-profit organization & support group for the transgendered, & Fetware community. We don't sell anything, & we don't data mine your personal information & habits to sell like MOST other sites do. We respect your privacy & won't sell it out for a few bucks.
Site for: Sissy Stories, ABDL Stories, Sissy Art, Crossdressing, Transgender