The Headmaster's Office - Cover

The Headmaster's Office

Copyright© 2023 by RetrospectiveInsomnia

Chapter 6

Erotica Sex Story: Chapter 6 - Sarah is punished by the headmaster for masturbating

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft   Coercion   NonConsensual   Reluctant   Heterosexual   Fiction   School   BDSM   DomSub   MaleDom   Humiliation   Sadistic   Spanking   Exhibitionism   Masturbation   Sex Toys   Voyeurism   Small Breasts   Teacher/Student  

Two weeks later, Sarah found herself staring once again at her shoes. And not because she was in trouble again or anything like that, though the feeling was close. Like every other time she found herself standing in front of the headmaster’s office with her fingers picking at the edges of her skirt, and if the familiar metal presence of her chastity belt had anything to say about that, then it certainly didn’t help. Nor did the weight of the plug she was still wearing stuffed up her rear, and she shifted in place against the awkwardness of it. The fullness had become a little more bearable after the first couple days of course, but she still hadn’t gotten used to the way it kept shifting about. Or the way it seemed to move from side to side every time she tried to run.

That was something for her to think about later once they were finished though, and so biting down on her lips she raised her hand to knock.

“Come in,” a voice called out from inside.

As always, it came through like the sound of the ocean mixed with the distant rumbling of a storm. Carefully, she opened the door. The headmaster glanced up at her, his eyes peering out from behind his glasses, and he smiled as he waved for her to sit down.

Oh right, of course. Sarah eyed the hard wooden surface of the chair in front of her with a somewhat doubtful look. She had been naive not to expect at least an interview or two after what she had done.

“Don’t worry, I don’t bite,” he said, “At least not for now. You’re not here for another punishment, are you?”

“No sir,” she mumbled.

“And I don’t seem to have anything marked on my schedule either, so I assume you’re here for something else,” he said, “Not another instance of sticky fingers, I suppose?”

“Ah no. I was just...,” she said again, “Well you see...”

It was only through a last-minute sense of self-preservation that she stopped herself from pressing her legs together as he looked on. That would not have turned out well at all. Instead, she forced herself to take in a deep breath as she slowly sat down. The chair made contact with her bottom, the shallow wooden curve of the non-existent padding rising up to form a ridge, and she winced as she felt the entire weight of her body resting against the base of the plug. Like an anvil balanced upon its point, and if she felt her walls let out another twitch from behind the thickness of her chastity belt, then who could really say that it was her fault. No, of course it wasn’t. Besides, it wasn’t like she hadn’t gone through something like this before. And against the silence that surrounded the two of them, she had more than enough things to worry about for now.

“No, sir,” she said quietly, “The matron ties my hands together to the bedframe every time I go to sleep now.”

It took some effort to keep a straight face. The punishment was something that only happened to the lesser-performing students who didn’t command as much trust. Looking across at her though, the headmaster simply paused for a moment as if thinking something over.

“You were that girl from two weeks ago, weren’t you?” he said slowly.

“I, umm...,” said Sarah.

“The one I had to lock up in a belt?” he said.

He looked over at her again, and it was like a lifeline thrown out to her across the waters. She clung to it hard.

“Yes sir,” she stammered, “You told me to come back when the time was up so I could have it taken off, but because I had to wear the plug the entire time it was hard for me to concentrate so they made me stand in the corner. And then since Mr. Simons said that I was a poor excuse for a student he made me bend over for a maintenance spanking in front of everyone else, and then every day after that he made me walk over to the front of the class for the paddle and...”

Wait, why was she telling him all of this again? Her voice trailed off as she dropped her gaze back down. Wasn’t she here just to have the chastity belt removed? That was supposed to be all, wasn’t it? Instead of the quick couple of seconds she had expected it to take though, her stupid mouth just had to go and betray her as if it had a life of its own.

The plug pressed up against her rear again, reminding her of its presence, and she bit down on her lips as she felt her opening let out another throb. It had been just over two weeks now since she tried to touch herself without permission, and at least ten times that amount since her last permitted orgasm standing up on the stage in front of the entire school. The pleasure of which had naturally been ruined as well, and as she watched the frustrating touch of the vibrator press down against her clit for a brief sixty seconds of torment before it was inevitably pulled away, it was almost as if the feeling was made even worse. Like an emptiness deep inside her that burned, and compared to the experience of having her walls clamp down over and over again on nothing but air, even another year of denial was starting to sound better.

But that was the past, she thought, shaking her head, and there was nothing she could do about what was already done. The clock ticked away beside them, and sitting there against the hard wooden surface of the chair, she clasped her hands together in an attempt to calm herself down. If the headmaster ever noticed though, he said nothing as he continued to stare at her from across the room.

“Anyhow,” she finally said, still looking away, “I learned my lesson so if you could just take it off...”

Her voice sounded fake even to her own ears, and she blinked in turn. A moment passed, and then another as she felt herself start to shake, and it was a bit like having to bend over at the front of the class again by the time the headmaster finally opened his mouth.

“I see,” he said, his voice slow and thoughtful, “I suppose then that two weeks is long enough.”

He reached over into the drawer of his desk, and she blinked at how easily he had moved.

“You mean just like that?” she said, before she could stop herself.

“Not unless you have another reason for me to keep you locked up,” he smiled.

He looked over at her again, his gaze much friendlier this time even as it made her feel exposed, and there was another twitch from somewhere inside her as she shifted against the tight metal prison of her chastity belt. Whatever thoughts came after that didn’t seem to matter all that much though as he took out a small silver key that glinted against the surface of his palm, and she stiffened as her entire body went numb. Like a girl who had just been offered a bottle of water after an entire year spent walking through the desert, though in reality it was hardly even close to half a month. Discounting, of course, the frustration of having to go to sleep every night with a medium-sized plug shoved up her rear hole.

Her teachers had even made it a habit of having her lift up her skirt for them every time she passed by in the hall. To see if it was still there, they had told her, though if she had to guess, it was probably just another lesson to help keep her fingers away from where they didn’t belong. Such was the punishment for the unfortunate souls of the academy who couldn’t stay clear of the rules after all. But that was a thought for later once she was back in her dorm. For now, she was just happy to finally be free of the belt.

The headmaster waved her forward, and pushing herself up from her seat she walked over to take off her uniform. First her top and then her blouse, the whiteness of the material pooling together onto the floor, and the rest of her clothes joined the pile a moment later as she stripped free of them as well. Including the delicate pieces of fabric that were her panties and her bra, and she blushed even harder as she felt the soft points of her breasts start to perk up. Like two miniature cherries that stuck out, and as if the shame of being seen like that wasn’t already bad enough, the humiliation only seemed to get even worse as she reached over to place her arms on top of her head with her legs spread apart.

Like that she stood there, and taking in as shallow of a breath as she dared, she closed her eyes as she waited for the headmaster to begin. There was another short pause as he made his way around his desk, and circling around her like a hawk he reached over to pinch her arm.

“You’re in your second year now, aren’t you?” he said.

“Yes sir,” she replied.

“And how have you been taking to your classes so far?” he asked, “Not too many detention slips from your teachers I hope?”

The question seemed to come out of nowhere, and she blinked as she tried to think of an answer.

“I...,” she said, “I don’t think so?”

“Then I don’t imagine that you’ll have too many issues moving forward from now on”, he smiled.

“No,” she said, blushing a little, “It was just the one from the, well ... you know.”

There was no need to complete the thought. The evidence itself was more than clear enough. Two metal bands of unbreakable steel, one that went around her waist with the other running down between her legs to cover her up, and locked away underneath the thickness of the belt was the reason for this entire farce. Or in other words, she had been caught red-handed with her panties pushed to the side and her fingers fumbling about a place where they really didn’t belong.

Her mind drifted back to the memory of the night she had been caught. If only she had a couple of extra minutes to finish, then she might have even gotten away with it as well. She hadn’t though, and so even though she had been right on the edge of a mind-shattering orgasm after so many months of denial, the only thing that had come out of it was the painful frustration of having her hand pulled away at the last second before she was made to bend over the edge of her bed for the paddle. And then a second time later on in the bathrooms for an enema along with a couple extra drops of chili oil. Better luck next time though, she supposed. That is if she ever thought she was smart enough not to be caught the second time around.

Behind her, the headmaster stopped to reach down. His fingers brushed up against the plug buried between her cheeks, and it was all she could do not to let out a moan. Perhaps her future husband might have a use for her bits down there, but until she found herself someone to marry, it was just another part of her body that she wasn’t supposed to touch.

“Bend over for me,” he said.

She did so instantly as if she had just been shocked.

“Very good,” he said, eyeing the way her back arched up, “Now stay still and try not to move.”

It was a phrase she had heard more than enough times before. The hand returned to spread her apart again, and she felt another tug against the base of the device as he drew it halfway out. Then, stopping at the last moment, he let go to watch as the natural clench of her muscles drew it back into her hole. Like her body didn’t ever want it to leave, and he repeated the process a couple more times before pulling it all the way out.

“Oh,” said Sarah softly.

On the fourth attempt there was a small pop as it left her, and she winced at the sudden emptiness left over inside her hole. Like a part of her was now missing, and she grit her teeth as she felt her walls let out another throb. Both from her g-spot and her anus, and despite how long it had spent stretched apart, the dark ring between her cheeks seemed to tighten up again like the flower of a chrysanthemum. Or perhaps it was just another one of those built-in reflexes that came from the frustration rising up from behind the belt. At least it wouldn’t be long before it was due to come off as well.

The headmaster held up the key, and she turned around to stand back up. There was another pause as he took in the state of her nipples, pointing straight out from the shallow curve of her chest as if begging to be touched, and she forced herself to look away as he knelt down. This was it, she thought. This was what she had been dreaming about for so long. There was a small turn of his hand and she closed her eyes. Following that was a soft click, and then with the weight of an entire two weeks of torment falling away, she let out a breath she didn’t know she had been holding as the metal bands of the chastity belt hit the floor.

“There,” said the headmaster, “How does that feel.”

It was all she could do not to reach down and see for herself. She resisted the temptation, if only just.

“Thank you, sir,” she whispered.

There was still the rest of the procedure to get through though, and so instead of reaching for her clothes she watched as the headmaster reached over into the drawer. Numbing cream first, she thought, since after having spent so long locked up it was almost a guarantee that her sensitivity was practically shot. Which was why they needed to go through this step as well if she didn’t want to be punished again just because her panties were rubbing up against her crotch. Being caught with her hands between her legs was one thing, but it was an entirely different matter to have an accidental orgasm from the simple act of sitting down.

There was a bench set to the side, and lying down on her back she spread her legs apart. The headmaster pulled up a chair as he sat down, and after taking out an innocent-looking jar, he gathered up a generous amount of the substance inside with a brush. He looked down, and for not the first time so far she was thankful that there was only a trace amount of wetness to be found. She had made sure of that in the dormitory showers beforehand, holding the pulsing water jet between her legs until her knees threatened to give out. It did nothing for the throbbing inside of her of course, but at the very least it was enough to wash away any evidence of her prolonged denial.

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