Despite the fearsome reputation that the St. Margaret’s Academy for Wayward Girls had gained for itself over the years, life at the school wasn’t always as bad as it seemed. Punishments were quite rare actually, and it was far from every day that a girl would be required to lower her panties to her knees. Out of the roughly one thousand students that attended, perhaps only about a dozen would end up being sent to the headmaster’s office per week. For the rest of the class, most of the days were spent quite carefree.

But as lenient as the academy was, there still came a time when the rules could no longer be ignored. Every now and then, something big would occur, and the school would be forced to play its hand. Or the paddle, in the case of Reena Patel as she stood before the headmaster with tears running down her face. One look at the situation, and it was quite clear that there was a punishment waiting for her at the end of the day.

“Please sir,” she cried, “It was a mistake, it won’t happen again!”

An international student and eighteen years old, her accent was lighter than most, through her New Delhi background and her family wealth was the most likely cause. Sinking down onto her knees with her hands clasped in front of her however, there was not a single trace of her traditional upper-caste mannerisms to be found. For a straight-A student who played the flute and was on the marching band, it was quite a sight to see.

“It was just once, and I didn’t even mean it!” she begged.

Sitting behind his desk, the headmaster sighed in response.

“Do you realize the magnitude of what you’ve done?” he said.

“Sir, I…,” said Reena.

“The issue here isn’t about just you now,” he said softly, “It’s become a matter of integrity for the entire school.”

The words stuck in like a barb, and Reena lowered her gaze to the floor. It was one thing for her to fail a test, or heavens forbid, try to touch herself between her legs. It was an entirely different matter, however, for her to be caught in an intimate relationship with a stranger from a nearby town. An older, postgrad lecturer as well, if that made things any worse.

It had started off rather innocently, a chance meeting between the two of them as they bumped into each other during one of her trips out. There was a café that she liked to visit, and sitting down together at the same table, he had been quite surprised to discover that she was reading the same book as well. Les Fleurs du mal, or The Flowers of Evil, as it was less elegantly put. Following that, the more they talked, the more it seemed natural for her to accept when he invited her out for a drink at the local bar.

She shouldn’t have, she really shouldn’t have, but separated from the controlled supervision of her parents and living halfway across the world, it hadn’t even occurred to her that she should have said no. And by the time the first round of drinks were ordered, it was as if her thoughts were no longer her own. Bourbon and shots of tequila, the first time she had dared to drink alcohol. And during the drive back, with things going the way they were, she soon found a hand pressing down on the back of her head as her mouth was filled with the taste of something else. A brief spurt of bitterness against the back of her throat, and the rest was a blur, the memories of what happened afterwards forgotten in the haze of youth.

Needless to say, even without her absence at the morning inspection the day afterwards, it hadn’t taken long for the school to find out.

“I’m really sorry, sir,” sobbed Reena.

“I’m sure you are,” said the headmaster.

“Am I… am I going to be expelled?” asked Reena.

It was as much of a confession of guilt as it was a plea for mercy, and staring down at the floor in front of her, her voice sounded almost broken as the words came out. The very thought of being kicked out was unthinkable. What would her parents say to her if they found out? They would disown her for sure, especially after they found out what she had done.

The headmaster looked across at her, and she swallowed hard as she tried to hold back her tears. His usual smile was missing, and a solemn expression stretched across his face where it would have been. Even in the past when she was being punished, he had always been nice to her so long as she was willing to repent. Now though, it was as if the very air of the room was pressing down against her like a stone around her neck.

Sitting behind his desk, the headmaster let out a sign as he set his pipe to the side. For once it was unlit, and the packed tobacco inside slowly curled upward as it dried against the air. When he spoke again, his voice sounded ever so slightly bitter as if he was more disappointed in her rather than upset.

“I have half a mind to,” he said at last.

“Please, I…,” said Reena.

“But,” he said again, cutting her off, “Considering your previous record, and the fact that this was your first offense, I’m willing to offer you a choice. Provided, of course, that your purity is still intact. If you own up to your mistakes and submit to three months of detention, then I’ll allow you to stay at the school.”

Silence, and then an eternity as her heart leapt up in her chest. And with a start, she realized, the reason why she was still here in his office now instead packing her bags. Whatever protests she had been about to say remained stuck in her throat as faint glimmer of hope rose up instead. He was giving her one last chance, she realized. A small one, but a chance nonetheless.

Reena felt a sense of relief. She had been fortunate that sitting side by side in the car that night, she hadn’t had the time to do much else aside from fumble around a bit in the dark. She had taken him in her mouth, and he had stuck a finger up between her legs, but with the limited room they had to move in, there was still a good chance that her virginity was still intact. At least she hoped so. There had been a bit of pain when he stuck his finger in, but it hadn’t gone in very far at all.

“Do you accept?” asked the headmaster.

Taking in a deep breath, Reena slowly dried her tears and nodded her head.

“Yes sir,” she said.

&&&&&&

Despite the newfound hope, there was still the matter of the actual inspection ahead of her, and Reena felt her face grow red at the prospect of even having to check. It made sense though why the headmaster would ask. The only students that were allowed to enroll at the academy were those who could keep themselves pure. He was willing to help her, but only on the grounds that her virginity was still intact.

The next steps after that were more than clear, and reaching up to take off the top half of her school uniform, Reena blushed in embarrassment as she lowered her skirt. Her panties followed a moment later, and she shivered as the cold air blew across the warm tones of her mahogany skin. Standing there in the nude, she resisted the urge to cover up as her nipples perked up from the center of her breasts. The small, pert mounds were hardly large enough to even be considered B-cup in size.

“Sir, I…,” said Reena.

“Don’t thank me” said the headmaster, “Thank yourself for not letting him go any further.”

It was the only opportunity she was going to get, and she wasn’t going to squander it by delaying any further.

“Yes sir,” she said.

Deep breaths now. It was just a standard purity inspection. She had gone through the procedure more than a dozen times now since she joined in her first year. But with her future resting on the results now, this time the anticipation felt so much worse. Moving her feet apart as she had been taught, she reached up to place her arms on top of her head.

“No, not like that,” said the headmaster, “On your back.”

“You mean like…,” said Reena.

“Of course,” said the headmaster.

So it was going to be a full-depth inspection instead then. Reena blushed as she realized what that meant. The only time she had been required to take one was in the nurse’s office the day she had arrived at the school. It had been one of the most embarrassing moments of her life, and she wasn’t really looking forward to repeating the process again. Most of the other times after that, the only thing she had to do was bend over and cough as someone looked up between her legs from behind.

Of course, the only other option was expulsion, and her parents would be far from happy if she suddenly arrived home without warning only halfway through the semester. Swallowing hard, she walked over to the desk and slowly laid down on her back. Lifting her legs up into the air, she wrapped her arms underneath them as she held them up against her chest. The headmaster stepped forward, and turning her head to the side, she waited patiently for him to begin.

“Comfortable?” he asked.

“Yes, sir,” lied Reena.

She flinched in surprise at the sudden touch as the headmaster trailed his hand up the inside of her thighs. Lying flat on her back however with her legs lifted out of the way, there was nothing she could to do stop him as he moved closer towards her most intimate place. Tracing softly over the sensitive surface of her skin, he gently ran his finger over the outer curve of her lips.

“Spread,” he said.

This was the part she hated the most. It felt embarrassing, but gritting her teeth together, Reena forced herself to obey. Reaching down with her hands, she slowly spread her labia apart for the headmaster to see. Then, lifting her legs up even higher into the air, she shifted her bottom forward again so that it hung out even further beyond the edge.

It was beyond awkward to have to expose herself in such a way, but there was no helping it as she did her best to hold still. A quick check was all that was needed. Five minutes, and then she would be allowed to climb back down. Framed by the soft contours of her inner folds, the entrance of her tunnel twitched ever so slightly as the headmaster gently placed the tip of his finger against her hole.

“Seems tight enough,” he said, “Have you ever stuck anything inside before?”

“No sir,” said Reena.

“Good,” said the headmaster.

He pushed down a little harder, and she closed her eyes in turn. Her pulse felt like a drumbeat inside her head as it pounded in response to the intrusion down below.

It was hard to think about anything else though as the headmaster held up a small flashlight and shined it down into the darkness of her hole. There was a slight tug as he adjusted his grip, and she held her breath as she waited for him to finish. An eternity seemed to pass as time stretched out in between. Then, the headmaster nodded once, and she let out a sigh of relief. Set a little less than an inch or so inside her, the soft barrier of her hymen was still very much in one piece.

“What were you going to do if your friend had insisted on using you here instead of your mouth?” asked the headmaster.

“I was planning on letting him use my… my…,” said Reena.

She trailed off, the words too much for her to say, and the headmaster stared down at her with a disappointed look on his face.

“Your ass,” he said.

Wordlessly she nodded, too embarrassed to speak. The fact that she had even thought of such a thing was proof enough of her sin. There was nothing more that needed to be said after that as the headmaster moved his finger down to tap against the puckered entrance of her backdoor. In hindsight, the idea of having something shoved up her rear didn’t seem as good of an idea as it had once been.

The feeling didn’t get any better when the headmaster reached over to take the paddle out along with a fig of ginger from the drawer.

&&&&&&

The first step of course was to take in a deep breath, and laying across the top of the desk, Reena tried to mentally prepare herself for the punishment that would no doubt came next. With her knees pulled up against her chest however, she couldn’t help but shiver as the headmaster stared down at the full length of her privates still spread open between her legs.

“Well?” he said.

“Sir?” asked Reena.

“Over the edge,” he said, “Unless you want to take your punishment over here instead.”

He reached out to flick her clit, and jumping up as fast as she could, Reena stood up and turned back around. Bending forward over the edge again, she reached out to grab onto the opposite end. Her bottom naturally rose up into the air as she arched her back, and she tried not to think about how much of a target it presented.

The only saving grace was that with her legs pressed together like this, her privates were no longer on display. Only the outer lips of her labia could be seen as they peered out from the place where her thighs parted to form a gap.

A hand reached out to spread her cheeks, and there was the cold touch of lubrication as it flowed over her backdoor. Then, a steady increase in pressure as the headmaster pushed the tapered end of the root against the tight ring of her hole.

“Ohhh…”

Reena found herself holding her breath as the tip of the ginger slid in. There was nothing she could do to stop it however as the headmaster pushed it in all the way inside. Secured by the handle carved around the base, only the last inch was visible as it protruded upward from between her cheeks. A tiny bud of beige against the darker chestnut of her skin.

For a moment, nothing seemed to happen as she tried to force herself relax. It was only when her bottom started to grow accustomed to the intrusion however, that the burning began.

“Oh,” she said.

And then a moment later as the heat rose even more.

“Oh! It hurts!” she cried.

“Do you want me to take it out?” asked the headmaster.

It was a trick question, and Reena desperately shook her head.

“No, just hurry, please,” she begged.

The longer it stayed in her, the more it started to burn, and with every twitch of her insides, the pain only grew worse. The thought was thrown aside however as the headmaster raised the paddle up and brought it down across her rear. Only at the last minute did Reena remember to count out loud, and bracing herself against the edge of the desk, she did her best not to clench.

Smack!

“One!” she gasped.

Smack!

“Two!” she gasped.

Smack!

“Three!” she gasped.

It was almost an impossible task though as each swing of the paddle landed across her cheeks. Desperately, Reena tried to move her hips out of the way, but no matter how hard she twisted her body, nothing seemed to work.

“Please sir,” she sobbed, “It hurts!”

Smack!

“Eight!”

Smack!

“Nine!”

Smack!

“Ten!”

On and on it went, and by the time she reached ten, Reena was past the point of trying to hold back her tears. Grabbing on tight with her hands, she sobbed as the headmaster set the paddle to the side. Pressing down against the base of the root, he pushed it ever so slightly deeper inside.

“You’re starting to get wet,” he said.

There was no way she should have gotten wet from just a spanking, but it was impossible to deny the truth as her nipples stood up again from the center of her breasts. Hanging down to drag against the surface of the desk, they sent shivers down her spine every time she moved.

Reena turned her head away in shame. A trail of clear fluids dripped down from between her thighs and gathering it up with his finger, the headmaster held it up to the light.

“What do you think?” he said.

Reena never felt more embarrassed in her life.

“I’m sorry sir,” she mumbled.

“Do I have to discipline you down here as well?” said the headmaster.

“Yes, sir,” mumbled Reena.

Snapping on a pair of latex gloves, the headmaster spread her apart again between her legs. At the same time, he reached into the desk again and took out a small bottle of oil. Dipping the end of a cotton swap into the slippery substance, he dabbed away the excess remains before inserting one end into the still-twitching entrance of her hole. He pushed it further inside until it made contact with the barrier of her hymen before finally taking it back out.

Reena felt the adrenaline in her body spike as the substance coated her insides. The oil was infused with capsaicin powder, and the moment the substance touched her, a second fire erupted across the walls of her tunnel.

“Water!” she cried, “Please, I need water!”

Instinctively, she tried to rise up from the desk, but the headmaster grabbed her and held her down. Swapping out the paddle with the cane, he raised it high up into the air. There was a swish, and Reena cried out as the thin wooden rod fell across the back of her legs. A sharp line of agony raced out across the crease of her bottom where the skin was the most sensitive, and jumping up and down, she cried out in despair.

Crack!

“Ah!”, she cried.

“Count, or we’ll start all over again,” said the headmaster.

Crack!

“E… eleven!” cried Reena.

Crack!

“T… twelve!” cried Reena.

Crack!

“T… thirteen!” cried Reena.

Each hit caused her to clench, and the walls of her tunnel screamed out for something cold as the oil spread around inside her even more. Between her legs, the folds of her labia convulsed as her inner muscles tried to push the burning substance back out. The more she tried however, the more her misery seemed to increase. To anyone watching from behind, the view of her open privates and anus swaying from side to side was quite a sight to see.

The only comfort Reena had was that the headmaster had chosen to ignore her clit for now. Despite her best efforts, the sensitive nub started to swell up between her legs even as she sobbed. The strange mixture of pleasure and pain felt both arousing and humiliating at the same time, and as the came continued to fall between her legs, she couldn’t help but shiver from the sensation once more.

Crack! Crack! Crack! Crack! Crack!

By the time it ended, Reena couldn’t even remember how long she had been laying across the surface of the desk, her privates burning with the shame of her punishment and the ginger root poking out from between her cheeks. A maze of angry welts ran across the length of her bottom from the firm flesh of her buttocks to the soft crease at the top of her legs. Even her thighs weren’t spared as the headmaster moved the cane down every now and then, and Reena whimpered as it took her by surprise.

Sobbing hard, Reena slumped down feeling more exhausted than she ever had. Her body felt almost numb now as tears ran down from her eyes. Using a soft and wet towel, the headmaster carefully reached down between her legs, and she winced as the cloth brushed up against her overstimulated flesh.

“Hush now,” said the headmaster, “We’re almost done.”

Reena took in a deep breath as she lifted herself up from the desk. Not much further to go now. Just one more step, and then she would be free to go. Of course, there was no way the headmaster would let her go with just that. As he walked over to the closet to pull out the punishment chair, Reena couldn’t help but whimper as her knees gave out underneath her once more.

&&&&&&

The punishment chair was just an ordinary chair. Made from smooth and plain wood, it had four legs, two armrests, and a back just like any other in the world. That wasn’t what Reena was afraid of, though. What gave her pause was the large phallus attached by its base to the seat of the chair.

Standing a little way besides her, the headmaster looked over with an understanding expression on his face.

“The sooner you get it over with, the sooner you can leave,” he said softly.

Taking out a small plastic bottle from his desk, he squired a generous amount of lubrication across the tip of the toy, and Reena felt the world slowly tilting away from her as the slippery substance slowly flowed down the sides.

“How long,” she whispered.

“One hour each day, or until you’ve copied the student handbook two times over from front to back,” said the headmaster.

Lines then, the most boring task in the world. With the entire phallus measuring out to about five inches in length however, there was no way the punishment would be as easy as it seemed. Still, it wasn’t as if she had much of a choice though. She had already been paddled and then caned more times than she could count in a single day, and her bottom never hurt as much as it did now. If she didn’t follow with it now, it would have all been for nothing.

Taking one last moment to compose herself, Reena stepped forward to straddle the phallus as it stuck up into the air. Clenching her teeth together, she slowly lowered herself until she felt the very tip of the device press up against the tight entrance of her rear. Having been subject to the presence of the ginger root for so long, she felt especially sensitive now, and it took her nearly everything she had to keep from moaning as she sank all the way down. The headmaster placed his hands on her bare shoulders from behind, and she whimpered as the pressure pushed her further down.

“Ready?” asked the headmaster.

Her clit twitched again in response to the fullness of the foreign object stuffed deep inside her rear. With nothing to hold onto, the walls of her empty tunnel clenched down uselessly in turn.

“Yes, sir,” said Reena.

“Good, then you may start,” said the headmaster.

Reaching out to pick up the pen, Reena turned to the first page of the student handbook in front of her and began. On the consequence of breaking curfew, and the punishments it entailed. Great, her most favorite topic in the world. It was especially ironic given that she had snuck out of the academy more than once during the course of her adventures out into the town. Apparently, all of her debts were now coming to collect.

A minute passed, and then a dozen more as she made her way down the full length of the first page. Over a thousand words in total spanning across six paragraphs of impossibly small font. Almost like a dictionary, if a dictionary was as thick as her hand. Turning to the second page, Reena reached for another sheet of paper and began to write: The most important value at the St. Margaret’s Academy for Wayward Girls is discipline. Thus, it is with much insistence that we ask the students of the academy to take notice and adhere to the rules set out…

The headmaster stood next to her, watching her intently as she continued to write. Every time she made a mistake, he would point it out for her to correct. The third time she did so however, he pressed a button, and the phallus inside her began to vibrate.

“Ooohhhh!”

Her entire body stiffened up as Reena dropped the pen onto the desk. Gasping for breath, she scrambled to pick it up before it fell to the floor.

“Focus,” said the headmaster, “Unless, of course, you want to start over from the beginning. The end result should be a perfect copy word for word.”

Taking the sheet of paper from her, the headmaster rolled it up into a ball, and Reena felt tears gathering in her eyes as he dropped it in the trash bin. She had been nearly three-quarters of the way through, and now she was going to have to start all over again. Another blank piece of paper, and her hands trembled as she moved the pen back into position at the top of the page.

The headmaster had yet to turn the vibrations off though, and with the entire length of the phallus still buried deep in her rear, it was only a matter of time before Reena felt the first drops of arousal seep out of her slit and onto the seat of the chair. She tried her best to ignore the feeling as she focused instead on not making a mistake. There was no doubt that the device was designed to keep her right on the edge of a climax, and there was no way the headmaster would let her cum even if she begged. She was fighting against time now. There was only so long she could concentrate before her mind was no longer able to think.

Ten minutes, twenty minutes, thirty minutes, and then it was onto the third page. Just another four hundred more to go now before she was done with her task. Or three hundred and ninety-eight if she counted the two she had already completed. Between her legs, she could feel her clit screaming out for her attention as it swelled up underneath the tight confines of its hood. With the amount of trouble she was already in though, she would simply have to put up with the frustration until she was finished.

Shifting in her seat again as she bit down on her lips, Reena had a feeling it would be a long time before she would be able to sit normally again in a chair.