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Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Today at 07:25:55 AM »
Chapter 382.
The ladies snuggled back into the chairs. Connie took a sip of wine. They regarded him smugly. He knew that they had him utterly at their mercy. His erection had settled into a state of aching, expectant hardness. He attempted, not very successfully, to conceal his arousal, keeping his hands in front of him, his balls concealed by his fingers and the tumescent shaft behind his hand. Even so, the gentle vibrations of the plug, which he could feel in his coc-k, made the temptation to play with it almost irresistible. He discovered he could palpate it by the slightest flexing of his wrist, producing subtle ripples of pleasure, and coaxing little flows of juice from the tip. Even as he was doing this, he looked at his audience with as innocent a face as he could command.
Connie put down her wine and smiled.
“Let me explain, Tim. Cressida has asked us to make some friendly enquiries into your sexual status. I understand you were briefly interviewed by the staff at ESDS, but she thinks we could offer a more sympathetic approach. It is important for your employers to understand your needs, so that they’ll be able to provide appropriate support. Now, first of all, may I ask, would you consider yourself heterosexual?”
“Oh… Yes, miss…”
“You do seem to be, I must say… But there was some mention of your relationship with your fellow boot boy… Bobby?”
“W-was there…?”
“You know there was. I believe there was an admission of some…mutual masturbation? Isn’t that correct?”
“W-was there…?” He didn’t like the way the questioning was going. He felt distinctly nervous. He unconsciously expressed his embarrassment by awkwardly crossing his legs.
“Careful, Tim. Don’t trip.”
“Miss…? I c-can’t remember exactly what I said… They were pressuring me, see? Bobby and I, we’ve, like, always been good friends…”
“Very good friends…”
“Yes… He’s a nice guy. We’ve known each other since we were kids. In fact I miss him quite a lot, now I’m with ESDS and he’s still at Pitt’s Wood. We used to have fun…”
“Tim, please answer the question. If you don’t, it’ll be the same as a lie, and I’ll have to turn this thing up to number three. Is that what you want?”
“N-no, miss… Well, I mean, maybe we did once…” Seeing her frown, he added, “I mean, a few times…”
“Interesting. But you’re not gay, right?”
“No!”
“This Bobby guy sounds interesting. I think we should get you two back together. What do you think, girls?”
“Absolutely!”
“Can’t wait!”
“In the meantime, I think you’d better explain just what you two have been getting up to, and how it all started…”
The ladies snuggled back into the chairs. Connie took a sip of wine. They regarded him smugly. He knew that they had him utterly at their mercy. His erection had settled into a state of aching, expectant hardness. He attempted, not very successfully, to conceal his arousal, keeping his hands in front of him, his balls concealed by his fingers and the tumescent shaft behind his hand. Even so, the gentle vibrations of the plug, which he could feel in his coc-k, made the temptation to play with it almost irresistible. He discovered he could palpate it by the slightest flexing of his wrist, producing subtle ripples of pleasure, and coaxing little flows of juice from the tip. Even as he was doing this, he looked at his audience with as innocent a face as he could command.
Connie put down her wine and smiled.
“Let me explain, Tim. Cressida has asked us to make some friendly enquiries into your sexual status. I understand you were briefly interviewed by the staff at ESDS, but she thinks we could offer a more sympathetic approach. It is important for your employers to understand your needs, so that they’ll be able to provide appropriate support. Now, first of all, may I ask, would you consider yourself heterosexual?”
“Oh… Yes, miss…”
“You do seem to be, I must say… But there was some mention of your relationship with your fellow boot boy… Bobby?”
“W-was there…?”
“You know there was. I believe there was an admission of some…mutual masturbation? Isn’t that correct?”
“W-was there…?” He didn’t like the way the questioning was going. He felt distinctly nervous. He unconsciously expressed his embarrassment by awkwardly crossing his legs.
“Careful, Tim. Don’t trip.”
“Miss…? I c-can’t remember exactly what I said… They were pressuring me, see? Bobby and I, we’ve, like, always been good friends…”
“Very good friends…”
“Yes… He’s a nice guy. We’ve known each other since we were kids. In fact I miss him quite a lot, now I’m with ESDS and he’s still at Pitt’s Wood. We used to have fun…”
“Tim, please answer the question. If you don’t, it’ll be the same as a lie, and I’ll have to turn this thing up to number three. Is that what you want?”
“N-no, miss… Well, I mean, maybe we did once…” Seeing her frown, he added, “I mean, a few times…”
“Interesting. But you’re not gay, right?”
“No!”
“This Bobby guy sounds interesting. I think we should get you two back together. What do you think, girls?”
“Absolutely!”
“Can’t wait!”
“In the meantime, I think you’d better explain just what you two have been getting up to, and how it all started…”
2
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on July 29, 2026, 05:58:53 AM »
Chapter 381.
When Connie was satisfied, she sent Tim back into the other living room to await instructions.
“I think Cressida will be happy with what we’ve got so far,” she remarked, scrolling through her phone. She changed the video card in the camera. “I’ll grab some vidcaps from here later, too. With all our snaps she’ll have plenty of images to choose from.”
“Why did she want a video as well?” asked Bridget.
“Basically, I think, as training material for the staff. As to what’s coming next, goodness knows what her plans are!”
“He’s had an easy time of it so far,” sneered Frieda.
“He certainly has,” remarked Bridget. “We’ve treated him like a friend – a guest, almost. But now we have to get down to serious business. He’s not going to like it…” She smiled thoughtfully. “Well, I suppose actually he may…”
“It’s going to be intense,” said Connie. “We only have a few days, and in that time we have to step up from mere coercion to conditioning him to accept any instruction and to perform any act, however humiliating, until a positive response is programmed into him, until he obeys without question, even without thinking. It’s a tall order, but if we succeed we get all the perks Cressida promised us. We becoming a branch of the firm, and have free rein with all the trainees.”
“Once he realises there’s no alternative, no escape…”
“Exactly, Frieda. He must lose hope entirely, and accept that his future is only with ESDS.”
They sat silent for a moment, contemplating the task ahead. Then Connie rose.
“Let’s rearrange things a bit. Move the camera so it’s directly in front of him. If we arrange three armchairs in the corner we can get a good view without getting in the way. Let’s make ourselves comfortable and enjoy the show. Maybe open that nice bottle of wine, shall we?”
“I’ll get some snacks organised,” said Bridget.
“I’ll do the chairs,” said Frieda.
“Great, Connie smiled. I’ll get him ready. Back shortly.”
She disappeared into the next room. Tim was waiting patiently, hands clasped in front of him.
“You’re a lucky boy, Tim.” (Despite his recent accession to adulthood, it had been agreed he would always be addressed as “boy”.) “Let’s get you undressed. You’re going to be a pageboy again for the rest of the evening.”
She helped him off with his maid’s uniform. Tim felt relieved. He was still smarting from the ordeal having to show off his panties. When he was naked, Connie started unpacking another Fantastex box.
“Pageboy outfit mark two.”
“Mark two?” queried Tim.
“Modified shorts. Zip fly…I bet you’ll make good use of that,” she smirked. What she was thinking of Tim had no idea. “And a couple of little appendages.”
The “little appendages” turned out to be a rubber butt-plug welded to the inside seam, a short slim stalk terminating in a small, smooth rubber egg, and a rubber retaining loop attached to the crotch. Connie was enjoying herself now. She pulled on a pair of surgical gloves.
“Step in…there we are…now, lean forward a little…hands on the back of the chair…” She picked up a tube of lube, squeezed some out onto the egg, and smeared it over. “Keep still… In it goes… Relax, Tim, for goodness sake! There…one last push…” Tim flinched. “Done. A bit cold, was it? I keep the lube in the fridge these days… Now the loop…excuse my fingers… Pop everything through… There you go? Is that comfortable? No? Never mind, you’ll soon get used to it.”
Alas, he knew he would. That wasn’t the issue. After all the handling, he could feel himself beginning to swell, and the retaining loop behind his balls wasn’t helping.
“Yes, thank you, miss…”
“You don’t sound very sure. Didn’t the girls at ESDS make you wear training pants? Apparently not. They should have done. These are the most basic modifications. A small smooth plug and a single retaining loop. We’ll move onto something more advanced, but all in good time. Deportment comes first, Tim. You can’t do justice to a smart costume if you’re slouching or walking carelessly. The plug will keep your back nice and straight, and ensure you walk with small, pretty steps, whether you’re a pageboy or a maid. So we’ll make it a fixture from now on. The retaining loop? Well, if you’re genuinely proud of your boyhood you should let everyone see it. Your pride, that is. You’re getting more grown up now. You can’t hide your light under a bushel any longer. Do you agree?”
“Yes, miss…”
She glanced down at the growing bulge in the front of his shorts, and gave a faint nod of satisfaction. “That’s better, isn’t it?”
She adjusted his shorts, tugged down the frills, slipped the belt through the loops, and buckled it up.
“Look at you! A proper pageboy! Super. Let’s go show the others.”
She took his hand and led him back into the smaller living room. Bridget and Frieda had already taken their places. There were three glasses of wine on the table, and two bowls of snacks, as if they were about to settle down to watch a film, or their favourite serial. Connie ushered him back onto the steel plate and reattached the ankle chain. Then she took a seat next to her friends. Frieda handed her a remote.
“Now, Tim, let me explain. That little egg contains a vibrator and a rechargeable cell. I can make it vibrate fast or slow, and gently or not so gently. Let me give you a demonstration.”
She pressed a button. Tim gasped, and squirmed like a hooked fish. The women burst out laughing.
“Oops, sorry… I accidentally put it on the highest setting. Let’s try number one…no, two. How does that feel?”
The gentle but relentless purring of the plug transmitted itself to the whole of his lower abdomen. He felt his erection growing, slowly but surely. He clasped his hands in front of him, pressed against his hardening boyhood. He looked at Connie pleadingly, but he could see from the satisfied expression on her face there was to be no respite. He tried to move his feet but the chains held him fast. He tried to breathe slowly, and pressed his feet and legs together in a vain attempt at resistance.
Connie smiled. “Just relax… Enjoy it. Now we have you where we want you, we need to ask a few questions. You must answer truthfully, though. Every time you lie I shall turn your vibrator up one notch. Understand?”
“Yes, miss… I won’t lie… Honestly…”
When Connie was satisfied, she sent Tim back into the other living room to await instructions.
“I think Cressida will be happy with what we’ve got so far,” she remarked, scrolling through her phone. She changed the video card in the camera. “I’ll grab some vidcaps from here later, too. With all our snaps she’ll have plenty of images to choose from.”
“Why did she want a video as well?” asked Bridget.
“Basically, I think, as training material for the staff. As to what’s coming next, goodness knows what her plans are!”
“He’s had an easy time of it so far,” sneered Frieda.
“He certainly has,” remarked Bridget. “We’ve treated him like a friend – a guest, almost. But now we have to get down to serious business. He’s not going to like it…” She smiled thoughtfully. “Well, I suppose actually he may…”
“It’s going to be intense,” said Connie. “We only have a few days, and in that time we have to step up from mere coercion to conditioning him to accept any instruction and to perform any act, however humiliating, until a positive response is programmed into him, until he obeys without question, even without thinking. It’s a tall order, but if we succeed we get all the perks Cressida promised us. We becoming a branch of the firm, and have free rein with all the trainees.”
“Once he realises there’s no alternative, no escape…”
“Exactly, Frieda. He must lose hope entirely, and accept that his future is only with ESDS.”
They sat silent for a moment, contemplating the task ahead. Then Connie rose.
“Let’s rearrange things a bit. Move the camera so it’s directly in front of him. If we arrange three armchairs in the corner we can get a good view without getting in the way. Let’s make ourselves comfortable and enjoy the show. Maybe open that nice bottle of wine, shall we?”
“I’ll get some snacks organised,” said Bridget.
“I’ll do the chairs,” said Frieda.
“Great, Connie smiled. I’ll get him ready. Back shortly.”
She disappeared into the next room. Tim was waiting patiently, hands clasped in front of him.
“You’re a lucky boy, Tim.” (Despite his recent accession to adulthood, it had been agreed he would always be addressed as “boy”.) “Let’s get you undressed. You’re going to be a pageboy again for the rest of the evening.”
She helped him off with his maid’s uniform. Tim felt relieved. He was still smarting from the ordeal having to show off his panties. When he was naked, Connie started unpacking another Fantastex box.
“Pageboy outfit mark two.”
“Mark two?” queried Tim.
“Modified shorts. Zip fly…I bet you’ll make good use of that,” she smirked. What she was thinking of Tim had no idea. “And a couple of little appendages.”
The “little appendages” turned out to be a rubber butt-plug welded to the inside seam, a short slim stalk terminating in a small, smooth rubber egg, and a rubber retaining loop attached to the crotch. Connie was enjoying herself now. She pulled on a pair of surgical gloves.
“Step in…there we are…now, lean forward a little…hands on the back of the chair…” She picked up a tube of lube, squeezed some out onto the egg, and smeared it over. “Keep still… In it goes… Relax, Tim, for goodness sake! There…one last push…” Tim flinched. “Done. A bit cold, was it? I keep the lube in the fridge these days… Now the loop…excuse my fingers… Pop everything through… There you go? Is that comfortable? No? Never mind, you’ll soon get used to it.”
Alas, he knew he would. That wasn’t the issue. After all the handling, he could feel himself beginning to swell, and the retaining loop behind his balls wasn’t helping.
“Yes, thank you, miss…”
“You don’t sound very sure. Didn’t the girls at ESDS make you wear training pants? Apparently not. They should have done. These are the most basic modifications. A small smooth plug and a single retaining loop. We’ll move onto something more advanced, but all in good time. Deportment comes first, Tim. You can’t do justice to a smart costume if you’re slouching or walking carelessly. The plug will keep your back nice and straight, and ensure you walk with small, pretty steps, whether you’re a pageboy or a maid. So we’ll make it a fixture from now on. The retaining loop? Well, if you’re genuinely proud of your boyhood you should let everyone see it. Your pride, that is. You’re getting more grown up now. You can’t hide your light under a bushel any longer. Do you agree?”
“Yes, miss…”
She glanced down at the growing bulge in the front of his shorts, and gave a faint nod of satisfaction. “That’s better, isn’t it?”
She adjusted his shorts, tugged down the frills, slipped the belt through the loops, and buckled it up.
“Look at you! A proper pageboy! Super. Let’s go show the others.”
She took his hand and led him back into the smaller living room. Bridget and Frieda had already taken their places. There were three glasses of wine on the table, and two bowls of snacks, as if they were about to settle down to watch a film, or their favourite serial. Connie ushered him back onto the steel plate and reattached the ankle chain. Then she took a seat next to her friends. Frieda handed her a remote.
“Now, Tim, let me explain. That little egg contains a vibrator and a rechargeable cell. I can make it vibrate fast or slow, and gently or not so gently. Let me give you a demonstration.”
She pressed a button. Tim gasped, and squirmed like a hooked fish. The women burst out laughing.
“Oops, sorry… I accidentally put it on the highest setting. Let’s try number one…no, two. How does that feel?”
The gentle but relentless purring of the plug transmitted itself to the whole of his lower abdomen. He felt his erection growing, slowly but surely. He clasped his hands in front of him, pressed against his hardening boyhood. He looked at Connie pleadingly, but he could see from the satisfied expression on her face there was to be no respite. He tried to move his feet but the chains held him fast. He tried to breathe slowly, and pressed his feet and legs together in a vain attempt at resistance.
Connie smiled. “Just relax… Enjoy it. Now we have you where we want you, we need to ask a few questions. You must answer truthfully, though. Every time you lie I shall turn your vibrator up one notch. Understand?”
“Yes, miss… I won’t lie… Honestly…”
3
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on July 28, 2026, 05:14:04 AM »
Chapter 380.
“Be a good boy, Tim,” added Frieda, “Do what your told, and tomorrow…we might give you a very special present. Right, Connie?”
“Well, yes… But he would have to be very, very good…” She gave Tim a mischievous smile. “It’s something any boy of your age would be delighted to have, Tim. Hardly any actually possess one. It’ll be yours to keep. However, whether or not we decide to give it to you is dependent on your being polite and obedient today. Do you think you’re up to it?”
Tim was curious, but suspicious. In any case, he had realised he had no choice. There was always an underlying threat of punishment. He wasn’t afraid of the whip, but if they decided to release a picture or a video...or even showed him off in public… His cheeks burned at the thought. Above all, he must keep his work for ESDS completely secret, and quite separate from his outside life. So he made a decision; to be totally compliant and obsequious from now on. He assumed a cheerful demeanour.
“Yes, miss Connie. I think I am. I’ll be good from now on. I won’t complain or sulk, I promise. So please don’t get your whip out again…”
He wanted to make her think he was terrified of the whip, so that this would seem her best deterrent.
“Good boy! I think you really mean it this time.”
He laid it on thick. “Yes, miss. I really do. I understand it’s all part of my training, and I should be thankful.”
“Excellent. Well, we have a few other outfits for you to try on. I’ll need to release you to change, and you will return to your maid-tidy without demur. Right?”
“Yes, miss. Of course, miss.”
“So while you’re in girl mode, let’s see what you look like in a maid’s uniform. Cressida especially asked for some pictures. Cynthia’s come up with a cute one and a more formal one, both in cotton and pink latex. I’m sure you’ll like them. You can wear one later this week, actually, and we’ll put you through your paces.”
“Can I take him?” asked Bridget.
“Help yourself…”
Bridget helped him change. The uniform wasn’t too bad. The panties, though… Pale pink latex, so fine it was translucent… He had to turn his back to Bridget to put them on.
“This is so pretty… Do you like it?”
“Yes, miss Bridget… And it fits perfectly.”
“Come on then. Let’s show the others.”
As he skipped into the room there was a chorus of approval. For a moment, in the sudden warmth of adulation, he forgot himself, and did a little twirl.
“Gorgeous!” simpered Connie. “Now let’s get you back on your disc.” She led him over and chained his ankles again.
“Why do I have to be chained up, miss?”
“We need to keep you in one place for the photos. Besides, Cressida particularly asked for it. I gather they’ll be going on the website brochure, and she wants to make sure her clients fully understand the subjugated status of her boys.”
“Oh…”
“And of course we don’t mind, do we, ladies?” Shaking of heads. “Personally I love all sorts of restraints. Especially on big strapping boys like you, Tim. It gives me a little thrill to know you’re completely in my power. What, are you shocked?” She emitted a short and not very pleasant laugh. “Later on I’m taking a few snaps of you for my own collection, and the best one’s going in a frame by the side of my bed. Does the thought embarrass you? Oh, it does! Look girls, he’s blushing again!”
Tim bit his lip. If this was the sort of humiliation he had to endure, well, so be it. He smiled and pretended he didn’t mind.
“Show us your panties, Tim,” called Frieda, rudely.
He smiled, treating the remark as a joke, which he hoped it was. It wasn’t.
“Go on,” said Connie, impatiently.
He turned bright red. This was too much. He tried to smile, but he just looked as if he was about to burst into tears. Reluctantly he lifted his tiny skirt. Apart from the fact his pride and joy was squashed flat against his stomach by the tight see-through latex, he might as well not have been wearing panties at all. He could feel them leering at him. Connie was seized with a fit of the giggles. For a moment he frowned and glared at her – then, remembering himself, quickly adopted an expression of pathetic, forced acquiescence.
The ordeal finally came to an end, and he was allowed to leave them room, accompanied by Frieda, to put on the formal maid’s uniform. This one was received with genuine admiration, enhanced by Frieda's idea of adding a fully-padded bra to his ensemble. Connie put him back on the disc, and all three of them snapped away while Tim forced a smile.
“You can wear this tomorrow and wait on us. Would you like that?”
“Ooh, yes please, miss…”
“I think Cressida will approve. It will be a good uniform for the posher clients. Yes. One more pose… Maybe with a tray… And then we’ll move on to something else.”
“Be a good boy, Tim,” added Frieda, “Do what your told, and tomorrow…we might give you a very special present. Right, Connie?”
“Well, yes… But he would have to be very, very good…” She gave Tim a mischievous smile. “It’s something any boy of your age would be delighted to have, Tim. Hardly any actually possess one. It’ll be yours to keep. However, whether or not we decide to give it to you is dependent on your being polite and obedient today. Do you think you’re up to it?”
Tim was curious, but suspicious. In any case, he had realised he had no choice. There was always an underlying threat of punishment. He wasn’t afraid of the whip, but if they decided to release a picture or a video...or even showed him off in public… His cheeks burned at the thought. Above all, he must keep his work for ESDS completely secret, and quite separate from his outside life. So he made a decision; to be totally compliant and obsequious from now on. He assumed a cheerful demeanour.
“Yes, miss Connie. I think I am. I’ll be good from now on. I won’t complain or sulk, I promise. So please don’t get your whip out again…”
He wanted to make her think he was terrified of the whip, so that this would seem her best deterrent.
“Good boy! I think you really mean it this time.”
He laid it on thick. “Yes, miss. I really do. I understand it’s all part of my training, and I should be thankful.”
“Excellent. Well, we have a few other outfits for you to try on. I’ll need to release you to change, and you will return to your maid-tidy without demur. Right?”
“Yes, miss. Of course, miss.”
“So while you’re in girl mode, let’s see what you look like in a maid’s uniform. Cressida especially asked for some pictures. Cynthia’s come up with a cute one and a more formal one, both in cotton and pink latex. I’m sure you’ll like them. You can wear one later this week, actually, and we’ll put you through your paces.”
“Can I take him?” asked Bridget.
“Help yourself…”
Bridget helped him change. The uniform wasn’t too bad. The panties, though… Pale pink latex, so fine it was translucent… He had to turn his back to Bridget to put them on.
“This is so pretty… Do you like it?”
“Yes, miss Bridget… And it fits perfectly.”
“Come on then. Let’s show the others.”
As he skipped into the room there was a chorus of approval. For a moment, in the sudden warmth of adulation, he forgot himself, and did a little twirl.
“Gorgeous!” simpered Connie. “Now let’s get you back on your disc.” She led him over and chained his ankles again.
“Why do I have to be chained up, miss?”
“We need to keep you in one place for the photos. Besides, Cressida particularly asked for it. I gather they’ll be going on the website brochure, and she wants to make sure her clients fully understand the subjugated status of her boys.”
“Oh…”
“And of course we don’t mind, do we, ladies?” Shaking of heads. “Personally I love all sorts of restraints. Especially on big strapping boys like you, Tim. It gives me a little thrill to know you’re completely in my power. What, are you shocked?” She emitted a short and not very pleasant laugh. “Later on I’m taking a few snaps of you for my own collection, and the best one’s going in a frame by the side of my bed. Does the thought embarrass you? Oh, it does! Look girls, he’s blushing again!”
Tim bit his lip. If this was the sort of humiliation he had to endure, well, so be it. He smiled and pretended he didn’t mind.
“Show us your panties, Tim,” called Frieda, rudely.
He smiled, treating the remark as a joke, which he hoped it was. It wasn’t.
“Go on,” said Connie, impatiently.
He turned bright red. This was too much. He tried to smile, but he just looked as if he was about to burst into tears. Reluctantly he lifted his tiny skirt. Apart from the fact his pride and joy was squashed flat against his stomach by the tight see-through latex, he might as well not have been wearing panties at all. He could feel them leering at him. Connie was seized with a fit of the giggles. For a moment he frowned and glared at her – then, remembering himself, quickly adopted an expression of pathetic, forced acquiescence.
The ordeal finally came to an end, and he was allowed to leave them room, accompanied by Frieda, to put on the formal maid’s uniform. This one was received with genuine admiration, enhanced by Frieda's idea of adding a fully-padded bra to his ensemble. Connie put him back on the disc, and all three of them snapped away while Tim forced a smile.
“You can wear this tomorrow and wait on us. Would you like that?”
“Ooh, yes please, miss…”
“I think Cressida will approve. It will be a good uniform for the posher clients. Yes. One more pose… Maybe with a tray… And then we’ll move on to something else.”
4
Active Sissy Stories / Re: A Trip to the Principal's Office
« Last post by sissy servant 737-820-633 on July 27, 2026, 12:17:14 PM »
Great read, easy to visualize or put myself into character
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Active Sissy Stories / Re: A Trip to the Principal's Office
« Last post by Baby Bobby on July 22, 2026, 02:46:26 PM »
Lol, this story was loosely based on one of my childhood experiences. In writing it, I wanted to try and put the reader into the emotional anguish of a boy about to get spanked by his intimidating, authoritarian Principal.
6
Active Sissy Stories / Re: A Trip to the Principal's Office
« Last post by BabyJay on July 20, 2026, 12:13:44 PM »
Hey!! Bobby, come on stop teasing us. You can't leave the story like this. We all want to know how His mother reacts to His arriving home in thick cloth nappies that are almost certainly soaking wet. Will She keep him nappies too?
7
Active Sissy Stories / Re: A Trip to the Principal's Office
« Last post by Babytinkles on July 20, 2026, 08:04:26 AM »
Oh please please keep this story going
8
Active Sissy Stories / Re: A Trip to the Principal's Office
« Last post by Baby Bobby on July 19, 2026, 11:41:31 AM »
Unfortunately for Brian, this now left his tiny little pen-is exposed, and the one inch appendage protruded from his crotch like a small, smooth cap. Having grown up with what is known in the medical profession as a micro pen-is, Brian was mortified to have it suddenly revealed to someone other than his mother.
Mrs. Sterne took one look at it and then up to Brian's blushing red face, her look saying everything about how pathetic she saw him as a budding adult.
With deliberation, she pulled him over her firm lap, even as Brian continued desperately to deny his guilt.
Unfortunately in her haste, Mrs. Sterne had quite forgotten to close the door and now, anyone walking down the hallway was free to stop and watch as Brian got his sissy bottom paddled. Belatedly realizing it himself, he pointed at the open door and stammered a string of incoherent words just as Mrs. Sterne raised her paddle and brought it down with a loud, terrific impact. Brian's soft, lily-white cheeks flattened under the ferocity of her harsh swat and his mouth opened in shock and pain. By the second swat, he'd found his voice and he howled in agony with each succeeding slap of of the paddle. It bit his tender flesh cruelly, and Brian kicked his feet wildly, unable to escape his humiliating and painful punishment.
Outside, two students heard the commotion and they stopped outside the doorway to watch the spectacle.
Needless to say, Brian was helpless to do anything about it, and Mrs. Sterne continued to smack his bottom soundly, even as he wailed at the top of his lungs. Hot, salty tears tumbled down his face as he cried like a baby.
It was true, his mom spanked him at home, but this was on a whole different level.
As the hard oak left painful, dark red marks and welts on his bottom, Brian's frantic kicking was inhibited by the wet pull-up tangled around his ankles.
As the spanking continued, the two students outside were soon joined by another pair, and then another. To be sure, word of this humiliating punishment would soon be spread to every student throughout the school.
Just when Brian was hoping she was finally finished, Mrs. Sterne would give him a flurry of rapid fire smacks that had him shrieking in agony. Although she had done a very thorough job of peppering the face of his bottom and turning it to a glowing red, she now gave her vengeful attention to the pink sides of his buns, smacking and swatting the area until it matched the hot, angry color of his seat.
At long last, the terrible spanking was over and his Principal set the paddle down on her desk with a clatter.
Brian was too weak to get up on his own, and Mrs. Sterne was surprisingly gentle about lifting him to his feet. Dancing in place, his hand shot down to his crotch, to try and cover the embarrassing stub of his pen-is from the leering teens out in the hallway. Tears streamed down his face, and Mrs. Sterne rose to her intimidating height of six feet, towering over the bawling student.
“Have you learned your lesson, Mr. Kimble?” she snapped without a trace of sympathy.
Brian nodded his head vigorously.
“Y-yes, Ma'am,” he blubbered between sobs.
Taking a moment to go over and close the door in the faces of the gathered students, she cleared off her tidy desk and opened a cupboard nearby. Brian bent over and was about to bring his pull-up back in place when Mrs. Sterne stopped him.
“Nope. You're not wearing wet pull-ups in my school the rest of the day. I've got something here that's better suited for you that will work just fine.”
Brian watched aghast as she arranged three thick cloth diapers, one on top of each other. He could see that their combined thickness would more than double what he was used to wearing but with his bottom on fire, he was terrified to stand up to Mrs. Sterne or oppose her.
Turning back to him, she pulled his shorts and wet underwear off from around his ankles and set them aside. Taking his hand, she led him over to the desk where she situated him on the stack of soft, fluffy cotton. Brian couldn't help but notice the thicker center of the diapers that looked like it contained a soaker section sewn down its length.
After powdering him generously, she pulled the bulky layers of cloth up and pinned the sides securely around his narrow hips. Brian whimpered and sniffled, feeling sorry for himself but otherwise doing nothing to stop her.
“I'm going to tell your mommy that she should be putting you in diapers and rubber panties for school. It's obvious that you failed Potty Training 101 and those pull-ups simply aren't going to cut it,” she told him in her firm, no-nonsense tone.
Returning to the cupboard, Mrs. Sterne brought back a yellow pair of nursery print-themed plastic panties. Brian sobbed as she pulled them over his feet and then up his legs, tugging and working with them to fit it over his big, embarrassing diapers.
“There, these will keep your wetting where it belongs,” she said as she ran her fingers around the elastic waistband, ensuring all of the soft cotton was contained inside the waterproof baby panties.
Dumping his wet pull-ups in the waste basket, she handed his shorts to him before taking a seat at her desk.
With practiced movements, she wrote a quick note and instructed him in no uncertain terms to give it to his mother when he got home. Brian began crying again as he imagined the reaction his mother would have when she found out what had happened at school today. He was sure he'd be taking a trip over her lap as well!
Pulling his shorts on, he quickly discovered they just barely fit over his new diapers and while he could just get the snap at the waist closed, the zipper was quite impossible to bring up, even a fraction of an inch.
With a sob of defeat, he realized that for the rest of the day, everyone would be getting a grand view of his babyish diapers, proving just how big a sissy he really was.
THE END
Mrs. Sterne took one look at it and then up to Brian's blushing red face, her look saying everything about how pathetic she saw him as a budding adult.
With deliberation, she pulled him over her firm lap, even as Brian continued desperately to deny his guilt.
Unfortunately in her haste, Mrs. Sterne had quite forgotten to close the door and now, anyone walking down the hallway was free to stop and watch as Brian got his sissy bottom paddled. Belatedly realizing it himself, he pointed at the open door and stammered a string of incoherent words just as Mrs. Sterne raised her paddle and brought it down with a loud, terrific impact. Brian's soft, lily-white cheeks flattened under the ferocity of her harsh swat and his mouth opened in shock and pain. By the second swat, he'd found his voice and he howled in agony with each succeeding slap of of the paddle. It bit his tender flesh cruelly, and Brian kicked his feet wildly, unable to escape his humiliating and painful punishment.
Outside, two students heard the commotion and they stopped outside the doorway to watch the spectacle.
Needless to say, Brian was helpless to do anything about it, and Mrs. Sterne continued to smack his bottom soundly, even as he wailed at the top of his lungs. Hot, salty tears tumbled down his face as he cried like a baby.
It was true, his mom spanked him at home, but this was on a whole different level.
As the hard oak left painful, dark red marks and welts on his bottom, Brian's frantic kicking was inhibited by the wet pull-up tangled around his ankles.
As the spanking continued, the two students outside were soon joined by another pair, and then another. To be sure, word of this humiliating punishment would soon be spread to every student throughout the school.
Just when Brian was hoping she was finally finished, Mrs. Sterne would give him a flurry of rapid fire smacks that had him shrieking in agony. Although she had done a very thorough job of peppering the face of his bottom and turning it to a glowing red, she now gave her vengeful attention to the pink sides of his buns, smacking and swatting the area until it matched the hot, angry color of his seat.
At long last, the terrible spanking was over and his Principal set the paddle down on her desk with a clatter.
Brian was too weak to get up on his own, and Mrs. Sterne was surprisingly gentle about lifting him to his feet. Dancing in place, his hand shot down to his crotch, to try and cover the embarrassing stub of his pen-is from the leering teens out in the hallway. Tears streamed down his face, and Mrs. Sterne rose to her intimidating height of six feet, towering over the bawling student.
“Have you learned your lesson, Mr. Kimble?” she snapped without a trace of sympathy.
Brian nodded his head vigorously.
“Y-yes, Ma'am,” he blubbered between sobs.
Taking a moment to go over and close the door in the faces of the gathered students, she cleared off her tidy desk and opened a cupboard nearby. Brian bent over and was about to bring his pull-up back in place when Mrs. Sterne stopped him.
“Nope. You're not wearing wet pull-ups in my school the rest of the day. I've got something here that's better suited for you that will work just fine.”
Brian watched aghast as she arranged three thick cloth diapers, one on top of each other. He could see that their combined thickness would more than double what he was used to wearing but with his bottom on fire, he was terrified to stand up to Mrs. Sterne or oppose her.
Turning back to him, she pulled his shorts and wet underwear off from around his ankles and set them aside. Taking his hand, she led him over to the desk where she situated him on the stack of soft, fluffy cotton. Brian couldn't help but notice the thicker center of the diapers that looked like it contained a soaker section sewn down its length.
After powdering him generously, she pulled the bulky layers of cloth up and pinned the sides securely around his narrow hips. Brian whimpered and sniffled, feeling sorry for himself but otherwise doing nothing to stop her.
“I'm going to tell your mommy that she should be putting you in diapers and rubber panties for school. It's obvious that you failed Potty Training 101 and those pull-ups simply aren't going to cut it,” she told him in her firm, no-nonsense tone.
Returning to the cupboard, Mrs. Sterne brought back a yellow pair of nursery print-themed plastic panties. Brian sobbed as she pulled them over his feet and then up his legs, tugging and working with them to fit it over his big, embarrassing diapers.
“There, these will keep your wetting where it belongs,” she said as she ran her fingers around the elastic waistband, ensuring all of the soft cotton was contained inside the waterproof baby panties.
Dumping his wet pull-ups in the waste basket, she handed his shorts to him before taking a seat at her desk.
With practiced movements, she wrote a quick note and instructed him in no uncertain terms to give it to his mother when he got home. Brian began crying again as he imagined the reaction his mother would have when she found out what had happened at school today. He was sure he'd be taking a trip over her lap as well!
Pulling his shorts on, he quickly discovered they just barely fit over his new diapers and while he could just get the snap at the waist closed, the zipper was quite impossible to bring up, even a fraction of an inch.
With a sob of defeat, he realized that for the rest of the day, everyone would be getting a grand view of his babyish diapers, proving just how big a sissy he really was.
THE END
9
Active Sissy Stories / Re: A Trip to the Principal's Office
« Last post by sissy servant 737-820-633 on July 18, 2026, 09:29:42 PM »
Good work as I can envision the story as if it was televised onto my screen
10
Active Sissy Stories / Re: Doll Factory
« Last post by dolly bo peep on July 18, 2026, 05:26:21 PM »
This was my first visit to this website in a very long time, and lo and behold! A new story by DaraJaney!
As soon as I started reading, I wanted to really savor the reading, so I stopped and got properly dressed:
A fresh diaper (tie-dye MegaMax with a booster), pink Leanne dress with black ribbons and trim, 4 layers of petticoats, pettipants with multicolor lace trim on view, short red wig with my white lace trim bonnet, black MaryJane shoes and white lace trim socks.
For the first time in a long time, I got out and washed my pacifier, hung it to a cord around my neck, also got out my Princess Pink bottle for the first time in also a long time and filled it with water, which I drank from while reading, alternating the bottle with the pacifier.
I read it all the way through, really enjoying it with my stuffed lamb Pinky by my side.
As soon as I started reading, I wanted to really savor the reading, so I stopped and got properly dressed:
A fresh diaper (tie-dye MegaMax with a booster), pink Leanne dress with black ribbons and trim, 4 layers of petticoats, pettipants with multicolor lace trim on view, short red wig with my white lace trim bonnet, black MaryJane shoes and white lace trim socks.
For the first time in a long time, I got out and washed my pacifier, hung it to a cord around my neck, also got out my Princess Pink bottle for the first time in also a long time and filled it with water, which I drank from while reading, alternating the bottle with the pacifier.
I read it all the way through, really enjoying it with my stuffed lamb Pinky by my side.
The more you give, the more I can give back.
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