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Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Today at 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.
“Everything ready? Right. Let’s begin. We’ll start gently.”
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 were sitting on the sofa, looking smug. There were three glasses of wine on the table, and two bowls of snacks, as if they were getting ready to watch 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 thighs 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.
“Everything ready? Right. Let’s begin. We’ll start gently.”
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 were sitting on the sofa, looking smug. There were three glasses of wine on the table, and two bowls of snacks, as if they were getting ready to watch 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 thighs 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…”
2
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on Yesterday at 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.”
3
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
4
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.
5
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?
6
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
7
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
8
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
9
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.
10
Active Sissy Stories / A Trip to the Principal's Office
« Last post by Baby Bobby on July 17, 2026, 04:59:56 PM »
Brian sat nervously on the single, lonely chair situated outside the school Principal's office.
His mouth was dry and he kept wiping his sweaty palms on the legs of his shorts. Just inside the next room, he could hear one side of a conversation; the strict, firm voice of Mrs. Sterne, who's name adorned the opaque glass window on the door next to him. Brian couldn't hear the other student's voice, but it was obvious he was being scolded just before his imminent spanking. Brian could imagine all too well what he must be thinking—soon the boy would have his pants pulled down and taken over her lap. Sure enough, there was a pause in her scolding and Brian's eyes widened as he heard the first resounding swat of the paddle on the student's defenseless bottom. Almost immediately, the boy's wails could be heard as the school's disciplinarian meted out his well-deserved punishment.
Brian squirmed in his seat, knowing all too well that he was going to be next.
He tried frantically to come up with some excuse that would allow him to get off with a mere scolding but it was hard to concentrate as the harsh swats continued to rain down on the poor boy's bare bottom. He was really crying now, and Brian could imagine him kicking and futilely struggling to escape.
Brian tried to think about what had brought about his recent misfortune. In fact, it was Melissa, the hottest cheerleader at his school that had chosen to bully him again. He had had a number of run ins with her, which often resulted in her humiliating him in some way. She was much taller than Brian and she liked to tease him incessantly whenever they crossed paths. 'Sissy' was her most common epithet for him and he studiously avoided the busty teen when at all possible.
Today it was not to be. Melissa had cornered him in the hallway, along with a few of her stunning cheerleader friends. They had pushed and teased Brian until Melissa pulled the fire alarm, which, minutes later, resulted in the school doing an unnecessary evacuation. Later, when the school authorities had investigated it, she had blamed it on Brian and her friends had backed up her claim.
So now, the poor sissy was sitting on a hard wooden chair outside Mrs. Sterne's office, about to get the spanking of his lifetime.
And his troubles didn't end there, either. Somehow, in all the day's excitement, he'd managed to wet the pull-up his mom insisted he wear under his clothes to protect against accidents. The soggy cloth clung stubbornly to his cheeks and squished warmly between his legs. And while he'd been able to keep his humiliating underwear a secret so far, all that was about to change.
At last, the spanking inside ended, and Brian gulped in fear. Suddenly, the office door opened abruptly and Mrs. Sterne led the crying boy out by his arm. He was rubbing the seat of his pants with one hand and wiping away the tears on his wet face with the other.
“Let that be a lesson to you, the next time you think about pulling a girl's skirt up,” she told him.
He scampered off down the hall, deeply ashamed and wanting badly just to get away.
Turning to face Brian, who was cowering in his seat, she wagged her finger at him accusatorily.
“And what is your name, young man?” she demanded, in a stern tone of voice that could cut through hardened steel.
“B-Brian, M-Ma'am,” he stammered nervously.
“Brian what?” she snapped.
The poor frightened boy felt a warm stream of pee escape into his wet pull-up as he swallowed hard.
“B-B-Brian K-Kimble,” he bleated out.
“Well, Brian Kimble--today, you're going to be taking a trip over my lap,” she told him as she reached down and snatched his wrist, hauling him to his feet and leading him inside her office.
“Wha-wait!” he cried, “I-I didn't do it!”
“Brian,” she stated, completely ignoring his remark, “you're going to get a good, hard spanking and that will teach you not to play with fire alarms at this school,” she said tersely as she led him over to an armless chair.
Brian quaked with fear as he laid eyes on the long wooden paddle with air holes, laying on her desk. It had obviously seen a lot of use, and the varnish was mostly worn off from its surface.
“But I didn't do it!!” he squealed desperately as she took a seat and began unsnapping the catch on his shorts, “M-Melissa did it!”
He hoped frantically that she would believe him but it was not to be.
Tugging his shorts down his legs, Mrs. Sterne stopped in shock as she discovered Brian's embarrassing pull-ups. The ones he was wearing today were a cute pastel baby-blue, with playful designs of bunnies and kittens across the front. His face went beet red as he tried to look away, tears of shame brimming in his eyes.
Momentarily at a loss for words, Mrs. Sterne shook her head as she looked up into his blushing face.
“Well, well, well,” she said slowly, “I'll bet you weren't expecting anyone to see your pretty pull-ups when your mommy dressed you this morning.”
Brian's knees went weak and he felt somewhat faint. The crimson color of his cheeks went to his neck, and all the way down to his chest.
“Maybe you should have thought of that when you were causing your mischief in B hall,” she scolded him as she hooked her fingers inside the elastic waistband of his pull-up. That's when she discovered he'd soaked his 'protection', but she just shook her head again in disapproval as she snaked them down his trembling legs.
His mouth was dry and he kept wiping his sweaty palms on the legs of his shorts. Just inside the next room, he could hear one side of a conversation; the strict, firm voice of Mrs. Sterne, who's name adorned the opaque glass window on the door next to him. Brian couldn't hear the other student's voice, but it was obvious he was being scolded just before his imminent spanking. Brian could imagine all too well what he must be thinking—soon the boy would have his pants pulled down and taken over her lap. Sure enough, there was a pause in her scolding and Brian's eyes widened as he heard the first resounding swat of the paddle on the student's defenseless bottom. Almost immediately, the boy's wails could be heard as the school's disciplinarian meted out his well-deserved punishment.
Brian squirmed in his seat, knowing all too well that he was going to be next.
He tried frantically to come up with some excuse that would allow him to get off with a mere scolding but it was hard to concentrate as the harsh swats continued to rain down on the poor boy's bare bottom. He was really crying now, and Brian could imagine him kicking and futilely struggling to escape.
Brian tried to think about what had brought about his recent misfortune. In fact, it was Melissa, the hottest cheerleader at his school that had chosen to bully him again. He had had a number of run ins with her, which often resulted in her humiliating him in some way. She was much taller than Brian and she liked to tease him incessantly whenever they crossed paths. 'Sissy' was her most common epithet for him and he studiously avoided the busty teen when at all possible.
Today it was not to be. Melissa had cornered him in the hallway, along with a few of her stunning cheerleader friends. They had pushed and teased Brian until Melissa pulled the fire alarm, which, minutes later, resulted in the school doing an unnecessary evacuation. Later, when the school authorities had investigated it, she had blamed it on Brian and her friends had backed up her claim.
So now, the poor sissy was sitting on a hard wooden chair outside Mrs. Sterne's office, about to get the spanking of his lifetime.
And his troubles didn't end there, either. Somehow, in all the day's excitement, he'd managed to wet the pull-up his mom insisted he wear under his clothes to protect against accidents. The soggy cloth clung stubbornly to his cheeks and squished warmly between his legs. And while he'd been able to keep his humiliating underwear a secret so far, all that was about to change.
At last, the spanking inside ended, and Brian gulped in fear. Suddenly, the office door opened abruptly and Mrs. Sterne led the crying boy out by his arm. He was rubbing the seat of his pants with one hand and wiping away the tears on his wet face with the other.
“Let that be a lesson to you, the next time you think about pulling a girl's skirt up,” she told him.
He scampered off down the hall, deeply ashamed and wanting badly just to get away.
Turning to face Brian, who was cowering in his seat, she wagged her finger at him accusatorily.
“And what is your name, young man?” she demanded, in a stern tone of voice that could cut through hardened steel.
“B-Brian, M-Ma'am,” he stammered nervously.
“Brian what?” she snapped.
The poor frightened boy felt a warm stream of pee escape into his wet pull-up as he swallowed hard.
“B-B-Brian K-Kimble,” he bleated out.
“Well, Brian Kimble--today, you're going to be taking a trip over my lap,” she told him as she reached down and snatched his wrist, hauling him to his feet and leading him inside her office.
“Wha-wait!” he cried, “I-I didn't do it!”
“Brian,” she stated, completely ignoring his remark, “you're going to get a good, hard spanking and that will teach you not to play with fire alarms at this school,” she said tersely as she led him over to an armless chair.
Brian quaked with fear as he laid eyes on the long wooden paddle with air holes, laying on her desk. It had obviously seen a lot of use, and the varnish was mostly worn off from its surface.
“But I didn't do it!!” he squealed desperately as she took a seat and began unsnapping the catch on his shorts, “M-Melissa did it!”
He hoped frantically that she would believe him but it was not to be.
Tugging his shorts down his legs, Mrs. Sterne stopped in shock as she discovered Brian's embarrassing pull-ups. The ones he was wearing today were a cute pastel baby-blue, with playful designs of bunnies and kittens across the front. His face went beet red as he tried to look away, tears of shame brimming in his eyes.
Momentarily at a loss for words, Mrs. Sterne shook her head as she looked up into his blushing face.
“Well, well, well,” she said slowly, “I'll bet you weren't expecting anyone to see your pretty pull-ups when your mommy dressed you this morning.”
Brian's knees went weak and he felt somewhat faint. The crimson color of his cheeks went to his neck, and all the way down to his chest.
“Maybe you should have thought of that when you were causing your mischief in B hall,” she scolded him as she hooked her fingers inside the elastic waistband of his pull-up. That's when she discovered he'd soaked his 'protection', but she just shook her head again in disapproval as she snaked them down his trembling legs.
The more you give, the more I can give back.
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