The Headmaster's Office

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.

“Now remember,” he said, “The more you move, the longer it’ll take to get it all on.”

“Are you going to apply it inside as well?” she asked.

“Do you need me to?” he said, “I can do that as well if you think it’ll make the process a bit more bearable.”

There was an appropriately sized plastic syringe already set out, and drawing back the plunger he deposited a small squirt of the cream just past the opening of her tunnel. Following that was the strange feeling of artificial warmth, and then a tingling that seemed to spread all the way into her core.

It was hard not to let out another moan. The entire thing felt strangely invasive and unnatural. There wasn’t much time to think about such things though as the brush came back again, and biting down on her lips she watched as it descended upon her folds. First her outer labia and then her inner as it slowly trailed up and down, and then moving inward bit by bit she felt it drawing closer and closer to her hole. Like the soft touch of a painter, and it was only a short stop from there before her clit was already starting to strain against the embarrassingly tight confines of its hood.

The headmaster leaned in closer, and she shifted her hips as she felt everything start to go numb. Just like the way it was supposed to, and by the time he stopped to pull out what looked like a small pink rotor attached to a wire, she could already feel her heart starting to pound.

“How long?” she whispered.

“Fifteen minutes, give or take,” he said, “Not quite the entire hour of training you’re used to, but it should help your body absorb it faster. Anywhere you would like it?”

“I…,” she said. She grit her teeth as she forced herself to choose. When she finally did, her voice barely came out as a whisper, “Just the front, sir.”

Meaning, that there would be no need for a second application of lube. The headmaster reached down with his hand again, and she felt her entire body stiffen up. At least it wasn’t going to go in her rear this time, even if the vibrations would feel less intense. After an entire two weeks of tossing long into the dead of night, she never wanted to experience the frustration of having nothing to clench down against inside her tunnel.

The rotor pressed up against her, and she tried her best to keep still. Already soaked through with her fluids though it had no trouble slipping in, barely even half an inch in diameter, and a simple push from there was all that was needed for it to disappear all the way past her folds. Blinking, she forced herself to look down. The only evidence that remained now was a small and delicate wire that trailed out of her almost as if it was some sort of tail.

“Ready?” he asked.

The headmaster tugged gently against the string before reaching over for the remote. It was now or never. She nodded once, and the toy came to life as he pressed down. Slowly at first, the vibrations barely even noticeable as it started to wiggle about in the tight confines of her hole, and then with a much deeper hum as the pitch rose up. Like a furious and angry tiger trapped inside her, and she bit down on her lips as she felt the stimulation echo through her core.

As much as it made her hips want to move, however, the feeling was dampened ever so slightly by the thick layer of numbing cream spread across her labia. Her clit rose up again, stiffer than it had ever been before, but by now there was no amount of stimulation that was capable of bringing her over. Not unless she could find some way to bypass the blockers attached to her nerves, and so letting out a sigh she forced herself to lay back even as her muscles continued to move.

The only thing left to do now was wait, she thought miserably. There was another clench from inside her, her walls squeezing down against the feeling of something solid for the first time in a while, but it was a fruitless endeavor. Instead, she focused on counting out loud the number of seconds that passed by as if it would somehow make the process go faster.

The headmaster turned the device up another notch, and she felt her hips shift upward a little more in turn.

“Almost a quarter of the way there now,” he said, “Do you want some water?”

He looked over to the puddle of fluid already starting to gather underneath her, and she shook her head with a groan.

“Maybe something for your other place to hold on to as well then?” he asked again, “Some girls prefer it that way, you know.”

There was another shake of her head, much more vigorously this time, and she pushed away the thought. It was true that some of her classmates preferred having their backdoors filled up over the frustration that came with being edged with their fronts, but after an entire two weeks of having to go to bed with a chastity belt wrapped around her waist, she really didn’t want to think about that right now. Least of all when she knew that there would be no relief waiting for her once it was over, and so closing her eyes with another sigh, she tried to keep herself from making any more noise than she already was.

The clock ticked away above her head, and her fingers curled together into a fist as she gripped down hard. Like that, the halfway point crept by not long afterwards, and she let out a silent groan as the headmaster moved over next to attach a pair of clamps onto her nipples. Each complete with their own miniature vibrator as well, and she bit back another cry of frustration at the silent hum.

“Just a little more now,” he said, “You’re doing excellent by the way. Most of the other students would be begging for me to let them finish by now.”

Most of the other students didn’t have the threat of being locked up in chastity if they messed up again though, she thought. Such was the consequences for trying to touch herself. A single strike, and maybe the school might forget about it after a couple months of proving that she really was a good girl. Get caught twice though, and it would be practically over for her. At least an entire year of denial if not more, and anything past that meant that she would be forfeiting her one chance at a ruined orgasm as well that she was due at the end of the semester. And as if that wasn’t already bad enough, aside from the frustration of having to watch as the rest of her classmates stepped up onto the stage for their long-awaited pleasure, the entire thing would only be made worse by the dildo she had to sit on the entire time as well.

She closed her eyes as she tried not to think about it too hard. It was a punishment from both sides. An emptiness in her front along with a fullness in her rear that did nothing but leave her wanting for more, and the entire thing was made even worse by the fact that it was a place that nature never intended to be used. Thus why so many of her trainings involved the use of her bottom, and she groaned as she felt herself slowly inching closer.

“How much more?” she gasped.

The headmaster simply smiled again though, as if they were in no particular rush. His voice came back gentle and cool.

“A little under a third,” he said, “Though judging by the way you’re starting to twitch down here, maybe you need a couple minutes more.”

“But I…,” she said.

“Then you better try your best to hold yourself back now,” he cut her off, before she could say any more, “Unless of course, you want for us to start all over.”

The vibrator buzzed a little louder, and she pushed back another whimper. He was right though. Now was not the time to lose her head, not when she was already so close. Both to the end of the time limit and to the edge of an orgasm, and despite the effects of the cream it was already as if her entire body was on fire. Like a furnace left on for too long, she spread her legs apart as wide as she could.

Deep breaths now, she thought to herself. Like that, a moment passed, and then another. How many more minutes did he say was left now? A little less than a third? Which meant another three hundred seconds of torment as the device continued to buzz away inside her sheath, and she grit her teeth as her insides let out another throb. No more, she thought, there was no way she could take any more of this. But it wasn’t as if she had a choice in the matter regardless of how awful it felt, and so closing her eyes again she forced herself to endure.

One second… two seconds… three…

The count went on. Then at last, halfway through another frustrating clench of despair, the crux of the climax finally came as the headmaster reached over again for the jar. The device inside her turned up to its maximum setting as he applied one last smear across her clit again with the tip of the brush, and her hips jerked forward against the emptiness making its way through her hole. Just as she felt the bristles making contact with her clit again though, it was as if an entire bucket of cold water was dumped on her all at once as he reached over to pull the toy back out.

“Oh!” she cried.

It was like nothing she had experienced before. Or maybe she had, but by now her brain was well past the point of understanding when it was. Or anything else at all besides how awful it felt. Like there was an ache deep inside of her that she wasn’t allowed to touch, and as her labia fluttered open once, twice, three times in rapid succession, the only thing that happened was a single painful twitch from her clit and then nothing at all. Not even the slightest hint of relief after having spent so long locked up, and by the time it was over, it was all she could do not to cry as her hands hovered just out of range with her fingers straining inward just to the side of her crotch.

“Are you alright?” said the headmaster.

The cool surface of the bench pressed up against her rear, and she tried very hard not to focus on the slickness of her labia. Or how much her nipples hurt.

“I’m fine,” she mumbled.

“It didn’t sting too much now, did it?” he said again.

“No sir,” she said, “It was just…”

She paused in thought. What was it like again? Like an irritating stab of frustration buried deep inside her clit as she felt her entire body let out another throb? It wasn’t as if she could just tell him that though, and so she did her best to dry her tears away as he handed over her clothes. Slowly she put them back on, and as the roughness of her panties pressed up against her slit, it was only through the familiar touch of emptiness inside of her that she realized the chastity belt was gone. Slowly, she swallowed down her previous words.

“It’s nothing,” she said again, “Thank you for taking it off.”

Then, with nothing else left to say, the rest of the process passed by in a blur. The sign out sheet made an appearance, and standing by the door her skirt went up one last time for the headmaster to examine the softness of her vulva. He smiled, his fingers tracing up the very center of her privates to give her a farewell tap just short of the top, and then with her clit made fully stiff again, it was finally time for her to go.

Mrs. Parker greeted her as she left. The middle-aged woman looked over from her desk, and the scrutinizing gaze left no trace of sympathy at all.

“Next time don’t make so much noise,” she scolded.

Sarah nodded quietly in turn. It was hard to tell whether the secretary was talking about the time she had just spent in the headmaster’s office or how she had been caught. Either way though, it was going to be quite a while before she would ever try and put her fingers where they didn’t belong. Or maybe not so long, she thought bitterly, since between the heat still trapped behind her clit and the stiffness of her nipples, it was all she could do to remind herself that it was all for her own good.

Right, for her own good…

She blinked as she made her way out into the hall. Who knows. Maybe this time when she gets her next ruined orgasm, it won’t even feel that terrible. Like a hard-earned victory after having to wait so long, and if she tried extra hard to focus on the feeling, maybe it might even feel good. One could only hope so given the circumstances after all. Like, wasn’t that how life was supposed to work?

After another moment of thinking about it though, against the memory of her walls clamping down on nothing but empty air, somehow she didn’t have the courage to think so. And for not the first time since she had been enrolled, she found herself wondering exactly how painful it would be to go through her entire next year after choosing to skip out. That was a decision for later though, for when she had to cross that bridge in a couple of months. For now, it was back to the usual routine of trying to focus as the fabric of her panties rubbed up against her crotch.