Note: This story was dynamically reformatted for online reading convenience. >The Headmaster's Office by RetrospectiveInsomnia Copyright(C) 2023 by RetrospectiveInsomnia Chapter 1 The headmaster -(TM)s office was a small, unassuming room located near the eastern side of the St. Margaret -(TM)s Academy for Wayward Girls. Built with only a single window in mind, the space inside was quite plain, resembling little more than a small squarish rectangle about as long as it was wide. Bookshelves, a few cabinets, and a single desk sat near the fireplace at the end. Aside from the brass nameplate that signaled who it belonged to, there was little else that stood out to the eye. Waiting in front of the office entrance, however, Sarah found herself wishing she was standing anywhere else except where she was now. She swallowed hard as she looked up at the school emblem hanging above the door. A lion stood triumphant over the dead body of a snake, its severed head trapped beneath a paw. Gathering up her courage, she raised her hand to knock. -Come in, - a voice called out from inside. Somehow, despite every single one of her senses telling her to turn around and run, Sarah managed to stand her ground. Opening the door just wide enough to slip through, she stepped inside, squinting her eyes as she did so. The morning sun was just starting to rise, and the light of its rays blinded her as it shone through the window. Slowly, the glare faded as her vision adjusted. -Sarah Whitney, - said the headmaster, -What brings you to my office so early today? - Sitting behind his desk, he looked up from his paperwork, and instantly Sarah dropped her gaze down to the floor. Biting down on her lips, she reached into her skirt pocket to pull out a tiny pink slip with a signature scrawled across the bottom. Sister Halsey -(TM)s handwriting, she had been the one doing the morning inspections today. Her hands trembled as the headmaster took it from her. -Hmmm, I see, - he said. The corner of his eyes wrinkled as he slowly read it over, and amplified by the silence that stretched out in between, Sarah felt every beat of her pulse as it echoed through her head. Still, she continued to stand where she was, her vision glued to the patterns of the carpet on the floor. She wanted to cough, sit down, do anything except stand there and listen to her own heartbeat, but her body no longer seemed to be under her will. What a situation to be in, she thought, and all for the sin of something she couldn -(TM)t even control. Had she been a just little faster at getting changed today, then perhaps Sister Halsey wouldn -(TM)t have even noticed. One glance at the dampness on the inside of her thighs however, and it was enough to send her all the way to headmaster -(TM)s office where she was standing now. The unfairness of it all rose up inside her, itching to burst out of her head. By the time the headmaster finally spoke, it felt like an eternity had passed, and Sarah let out a breath she didn -(TM)t know she had been holding. -And is this the first time that this has occurred? - he asked. The leash broken, the words seemed to rush out all at once. -Yes! - said Sarah, -I mean no- ... but I didn -(TM)t mean to this time! And when I asked Father Alex last week, he said as long as I keep my thoughts pure then it doesn -(TM)t count and-... - She trailed off as the headmaster looked up with a keen eye, and she moved her own to stare back at her feet. -So, this isn -(TM)t the first time, - said the headmaster. -No Sir, - said Sarah, her voice a little quieter. -And have you have been punished for this before? - asked the headmaster. -Yes Sir, - said Sarah. -So you knew what would happen if you did it again, - he said. Now, her voice shrunk down to a whisper, her lips barely even moving. -Yes Sir, - said Sarah. The headmaster hummed to himself and leaned back in his chair, and she clasped her hands together in front of skirt, standing with her feet spread ever so slightly apart the way she had been taught since she first arrived at the school. It must have worked, however, since the questions stopped there. Picking up his pipe from the desk, the headmaster measured out a small wad of tobacco and packed it into the bowl. Striking a match, he puffed at the stem until the fire caught, and the pipe lit up with an orange ember glow. Sarah waited patiently for him to speak, her hands trembling a little as he opened a drawer to put the matchbook away. -So, - he said. So what, she wanted to ask, but she held her tongue. -So, - he said again, -What am I do to with you now that you are here, Ms. Whitney. - More silence, broken only by the tick-tock of the grandfather clock outside as it chimed down the hall. Dimly, Sarah could hear the other students walking by as they prepared for their morning classes. Chatter of gossip perhaps, or of assignments long overdue, whichever was most interesting to the present company. She followed the lines in the carpet as the headmaster puffed away, waiting patiently for an answer. A minute passed as they stood there, each waiting for the other to speak. In the case of the headmaster though, it was more like standing before a statue of stone. Her mind spin as she bit down on her lips again, trying to think of something to say. -I -(TM)m going to be punished? - she asked. It was both a question and a statement at the same time, and the headmaster drew on his pipe, slowly blowing the smoke out through the air. -Do you feel like you deserve to be punished? - he asked. Immediately, she closed her mouth and tried not to think too hard about her response. The question was one that every girl at the school knew by heart, and in most every case, the more complicated the answer, the longer the punishment that followed. Fail to give an adequate answer, however, and the results would be even worse. Sarah fidgeted, shifting her weight back and forth on her feet as she tried to think of something in the middle. -I don -(TM)t know, - she said at last. The headmaster took one last draw from his pipe and set it aside, and Sarah watched as a thin trail of smoke drifted upward towards the ceiling. It flickered a little as the headmaster stood up to walk around his desk. He stopped before her, and she swallowed as her throat went dry. -Well then, I suppose we -(TM)ll have to find out the answer to that together, won -(TM)t we? - he said. Looking up into the gentle gaze of his eyes, briefly, Sarah wondered if she had made the right choice. &&&&&& Getting dressed every morning at the St. Margaret -(TM)s Academy for Wayward Girls was an easy task. Everyone wore the same standard uniform, which eliminated the difficulties of having to select an outfit every day. Consisting of a school blazer, a pair of stockings, and a knee length skirt, the design was simple and robust, and even fast to prepare. But while putting on the uniform was easy, taking it off, especially with the someone watching her, was a much more difficult task. Standing before her, the headmaster smiled as he waited for her to start. -Skirts up now, - said the headmaster, -All the way. - Turning her head to the side, Sarah reached down to take hold of the edge of her skirt. The headmaster made no attempt to rush her as she lifted it up above her waist. Then, spreading her legs until they were shoulder width apart, she stood with the soft fabric of her panties on full display. The headmaster reached out his hand, and Sarah bit down on her lips as his touch trailed up the inside of her thighs. Little by little, his fingers moved closer until they hovered at last over the mound of her most intimate place. She shivered as she waited for him to continue. Every instinct told her to close her legs against the intrusion, but she had little choice except to endure. Stuck in her current situation, refusing now would only make the upcoming punishment even worse. -Hnnn-... - Pausing only for the briefest of moments, the headmaster finally touched her, running his fingers down between the cleft of her vulva and rubbing her through the thin fabric of her panties in between. Using his thumb, he pressed down against the tiny protrusion near the top of her lips, and Sarah gasped as a spark of electricity jumped across her skin. Static filled her head as the friction caused something inside her to stir, and slowly, she felt her body starting to tense up, as if there was a spring inside her being stretched tight. All the while, the headmaster continued to rub her, moving his fingers around in circles as he teased her to the edge. -Ahhh- ... please, I-...! - The moment she felt something start to rise however, the headmaster stopped and pulled his hand away. Breathing hard, Sarah watched as he rubbed his fingers together, and a clear strand of fluid stretched out to hang in between. Down below, she could feel the sticky heat of something flowing down the inside of her thighs. -Well? - he said. -I-..., - said Sarah, -I didn -(TM)t-... - I didn -(TM)t mean to, she wanted to say, but standing there with her skirt raised up and the proof of her arousal visible for her to see, no excuse could save her now. She tried to not rub her legs together as the wetness of her panties pressed up against her skin. Instead of appearing angry however, the headmaster looked down at her with what appeared to be amusement in his eyes. -It seems that the lust of your previous sins still remains, - he said. Sarah hung her head in shame. -Yes Sir, - she said. -And how do you think we should solve that? - said headmaster. -By- ... by punishing me, Sir, - said Sarah. It was both an admission of guilt, and an acceptance of her failures at the same time. The way forward after that was more than clear, and tears welled up in her eyes as she reached up to undo the buttons of her uniform. The cold temperature of the room blew across her skin as she set her clothes aside, and from the center of her still developing chest, she could feel her nipples growing hard as they swelled up into the air. Standing there with only her underwear left to protect her modesty from sight, she resisted the urge to cover herself up as she stripped free of them as well. Taking in her naked form, the headmaster waved her towards an empty space on his desk, and she walked over to bend over the edge. -Thirty strokes, and we -(TM)ll call it even, - he said, -How does that sound for today? - Sarah clenched her teeth together, forcing herself to respond. -Yes Sir, - she said. There was the sound of a drawer being opened, and then several objects being laid out across the surface of the desk next to her. Sarah tried not to look too hard at the tools as the headmaster pulled them out. A paddle with holes cut through it, a leather crop, several rattan canes, there seemed to be no end to the pile. Selecting a wooden ruler, the headmaster swung it a few times, testing its balance and heft. -Now then, - he said, -Make sure to keep a good count, or we might have to start from the beginning again. - There was no warning for the first strike, and Sarah jumped in surprise as she felt the impact of the blow strike across her rear. For a solid second, she felt nothing, and then there was the fiery burn of pain as the skin of her left cheek slowly turned a pink shade of red. Tapping the end of the ruler against his palm, the headmaster waited for her to settle back down before raising his hand again. -Smack! - -O- ... one! - This time, Sarah remembered to count, and her hips jerked forward as she felt the surface of the ruler strike right across the sensitive strip of skin on the back of her thighs. More pain flared across her flesh, amplified by the heat that was slowly gathering between her legs. She shivered, unable to decide whether to faint or go red as a trickle of arousal seeped out of her to flow down her legs. -Smack! - -T- ... two! - Another blow, and another cry as she held on tight to the other side of the desk with her hands. -Smack! - -T- ... three! - -Smack! - -F- ... four! - -Smack! - -F- ... five! - By now, her vision was starting to swim, and the headmaster paused briefly to allow her to recover. Setting the ruler aside, he reached out to gently caress her bottom, rubbing over the area where the pain had set in the worst. Sarah sniffed, blinking as a tear leaked out from the corner of her eye. -Twenty-five more to go, - said the headmaster. He picked the wooden paddle this time, and giving her bottom a few soft taps with the surface of the device, he raised it up into the air. -WHACK! - -Aaughhh- - All the breath in her body seemed to have left all at once, and Sarah gasped as she tried to brace herself against the desk. -WHACK! - -Aahhh- ... S- ... six! - Compared to the ruler, the paddle hurt almost twice as much in turn, and with its larger surface area, it was able to strike across both her cheeks at the same time. Sarah trembled as the headmaster lined it up across the bottom of her rear, right where the ruler had struck her on the second blow. -WHACK! - -Ohhh- ... S- ... seven! Please Sir, not there-... - The plea was futile however, and the headmaster raised the paddle to strike the exact same spot several times more. Sarah tried to keep herself from crying out loud, but against the constant blows of the punishment, there was just no way. More tears rolled down her face as she sobbed in silence, holding on to the opposite end of the desk so hard her knuckles turned white. -WHACK! - -Ohhh- ... E- ... eight - -WHACK! - -Aaugh- ... N- ... nine! Please Sir, somewhere else! - -WHACK! - -T- ... ten! - At ten, there was another break, and setting the paddle aside, the headmaster reached out with a tissue to wipe away the tears on her face. -Be strong now, - he said, -Only twenty more to go. - Twenty! Already she felt like she was at her limit, and they weren -(TM)t even at the halfway point yet. Sarah wailed as she lay across the top of the desk and cried. A moment later however, dread shot through her as the headmaster reached next for the cane. -No, please, not that! The paddle, use the paddle! - she begged. The headmaster paused, and hope rose up inside her as he considered the offer. A moment later, however, he shook his head in pity. -If I used only the paddle, would you have learned your lesson? - he asked. Sarah opened her mouth to respond, but just before she could, she stopped as the meaning of the words became clear. Everything in her screamed for her to say yes, but standing over her, the headmaster looked down at her with a careful, calculating eye. Slowly, she lowered her head in despair. For just a moment, she had been just a hair -(TM)s breath away from falling into a trap of her own making. Had she tried to lie, then there was no telling how the rest of her punishment would go. -Please Sir, use the cane to punish me, - she whispered. The headmaster nodded in acknowledgement of her choice. Before he started up again, however, he stopped and reached once more into the drawer. -It is good that you were able recognize the nature of your sin, - he said, -Regardless, since you seemed so hesitant, I feel that further motivation is needed for your penance. - Rummaging around inside, he took out a large knob of ginger about four inches long and just over an inch wide, and began to peel away the skin with a knife. Near the bottom, he cut a shallow channel all the way around the outside, and Sarah watched as he formed the root into the shape of an oblong cylinder with a tapered base. All of a sudden, the cane didn -(TM)t seem so bad. Moving to stand behind her, the headmaster reached out to spread her cheeks, and she winced as he tapped his finger against the tight ring of her backdoor. -Many girls think that they can circumvent their desires by playing with themselves back here, - he said, -Of course, in their foolishness, such an act only causes their condition to grow worse. With the use of some ginger, however, they can be taught to keep their hands away from both their front and their rear. - He pressed the knob of ginger down against the entrance of her backdoor, and instantly Sarah cried out as she felt the sensation of burning against her ring. Struggling to breathe, she tried to rise up from the desk, but the headmaster held her down. He pushed harder against her backdoor again, and she wailed as the entire length of the root slid inside. It settled down inside her, the base end sticking out an inch or so as she clamped down on the tapered channel the headmaster had cut. -Ooohhh- ... it hurts! Take it out, take it out! - The cheeks of her rear pushed outward as her muscles tried to expel the burning sensation thrust up her rectum. Every time she tried however, the burning just became worse as the walls of her insides squeezed down around the root. Keeping his hand pressed against the small of her back, the headmaster lifted the rattan cane high up into the air. -Swish! - -Aaaiiihh-... - The moment the cane hit, Sarah made the mistake of clenching down and paid the price. Instantly, the pain was made a magnitude worse by the chemical heat of the ginger as she squeezed down. Kicking her legs out behind her, she sobbed in despair at the foreign object shoved up her rear. -Count, - said the headmaster. He raised the cane up, and Sarah desperately tried to escape. She twisted her body to the side, but it was no use. -Swish! - -Aaaiiihh-... - -If you don -(TM)t count the strokes, I will be forced to start the punishment over at thirty again, - he said. Dimly, his voice seemed to be coming through to her as if he was standing a long distance away. Despite the pain she felt however, Sarah forced herself to listen to the words. As the third stroke came down, she forced herself to relax her muscles as much as possible, raising her bottom up directly into the path of the cane to prevent herself from clenching when it hit. -Swish! - -Oohhhhh- ... E- ... eleven! - Reaching down with his hand, the headmaster tapped his finger gently against the fig of ginger as it stuck out of her backdoor, and she groaned in turn. -There we go, - he said, -Now just nineteen more. - He raised the cane for the twelfth stroke, and Sarah felt her head starting to grow light as she once again presented her bottom for the cane, relaxing herself as much as she possible to prevent herself from suffering the burn. -Swish! - -T- ... twelve! - -Swish! - -T- ... thirteen! - -Swish! - -F- ... fourteen! - On and on it went until each blow sent stars dancing before her eyes, and she felt as if she was going to faint. By the time they reached the twenties, her vision had begun to blur from her tears again, and the skin of her bottom was now an angry welt of red. Still, the headmaster continued onward, switching to a newer cane for more variety as he made his way through the set. -Swish! - -Twenty-one! Thank you Sir! - -Swish! - -Twenty-two! Thank you Sir! - -Swish! - -Twenty-two! Thank you Sir! - Halfway through, and for reasons that even she couldn -(TM)t quite understand, she had started to thank the headmaster for each stroke she received. As embarrassing as it was to hear herself say such a thing, however, it made the pain of the punishment a little easier to bear. Every now and then, the headmaster would stop and adjust the position of the ginger root, and she would groan as he pushed it deeper inside her backdoor. Then, with her bottom raised up as high as it would go, she would force herself to relax and wait for him to use the cane once more. -Swish! - -Twenty-seven! Thank you Sir! - -Swish! - -Twenty-eight! Thank you Sir! - -Swish! - -Twenty-nine! Thank you Sir! - This was it, one more stroke, and then she would be free. As the headmaster set the cane aside to pick up the leather crop however, Sarah trembled with fright. Unlike the first stroke which was the easiest, the last stroke was always the hardest, and for reasons that would soon become clear. Pushing herself up from the desk, she turned around to lay on her back and drew her knees up against her chest. With her legs spread to the side in an M position, she waited with the full length of both her privates and anus on display. -Which one, front or back? - asked the headmaster. An eternity seemed to pass on by as Sarah thought about the question inside her head. If she chose her front, then she would only receive a single stroke between her legs. If she chose her back however, she would have to receive two instead. Normally, that was still the better option, but with the ginger root inside her now, she didn -(TM)t even want to think of how it would feel to be punished back there. -M- ... my front, - said Sarah. The headmaster nodded, and with trembling hands, Sarah reached down to spread apart the lips of her most intimate place, opening herself up so that the entirety of her folds was on display. Between the pink contours of her flesh, the entrance of her hole could be seen, along with the virginal barrier of her hymen inside. It was here that the headmaster placed the tip of the leather crop, and she winced as he tapped down against her sensitive folds a few times. -Your hole, or your-... - he started to say, but she interrupted him before he could finish. -Please, my hole! - she cried, -Not the other place! - The headmaster smiled a little, amused by her sudden desperation, and her heart skipped a few beats as he moved the leather crop up to hover over the hidden nub at the top of her spread open lips. -Are you sure you don -(TM)t want it here instead? - he asked. -Please, punish my hole, - begged Sarah. -Even if it means two strokes instead of one? - said the headmaster. Sarah trembled as she watched him rub the tip of the leather crop against the covering of her hood, slowly peeling away the flap of skin that protected the sensitive nub underneath. Two strokes, could she take two full strokes between her legs? But looking down as the headmaster drew back her hood, there was just no way she could take the punishment, even if it was only a single one, up there. She swallowed hard, her voice shaking as she forced herself to answer. -Please, I beg you, punish my hole, - she said. -Very well then, - said the headmaster, -And why are we punishing your hole? - Her legs shook with the effort of keeping herself spread open for so long. -B- ... because I tried to masturbate, - she whispered. Here she was, lying naked on her back with her legs spread open and a knob of ginger shoved up her backdoor. Between her thighs, her privates glistened with the fluids of her own arousal despite the pain from the earlier strokes of the cane. Even now, she struggled to push aside the feeling of emptiness and frustration that her body sought so desperately to fulfill. The leather crop came up, and she watched in slow motion as it came down, landing right between her legs and on top of her aching virginal hole. -AAAIIIIEEEE-...! - Her voice cut off halfway through the scream as she gasped for air, her breath no longer existing in her body. Her legs twitched as her toes curled down, shaking and trembling like a leaf caught up in a storm. Through some miracle, however, her fingers remained where they were, keeping her most intimate place spread open for the headmaster to see, even as molten fire flowed through her veins. Had she let go, then the stroke wouldn -(TM)t have counted. -Did that feel good? - asked the headmaster. -No! - cried Sarah. The headmaster tapped the end of the crop against the pinkness of her abused flesh. -Are you going to keep sticking your fingers down here where they don -(TM)t belong? - he asked. -No! - cried Sarah. -And are you going to play with your bottom, or the little nub that you begged me not to punish? - he said. -Please Sir, no more! - cried Sarah. The crop rose up one more time, and she watched in horror, her hands frozen in place as it came down again between her legs. It landed with a sharp smack, and her vision turned white as every muscle in her body clenched down all at once, the pain shooting through her amplified further by the burning in her rear. Between the spread lips of her privates, she felt the frustration rising as the blow threw her towards the edge of the abyss. Scrambling desperately to keep from falling over, she clung to the knife -(TM)s edge, desperately praying that she would be able to keep herself from spending. Then, it was over, and she sobbed as her legs gave out, lying back against the surface of the desk with her head turned away. Gently, ever so gently, she felt the headmaster reach out to take hold of the ginger root, and she hissed as he drew it out of her backdoor. Setting it aside, he reached out with a tissue to wipe away the tears running down her face. -Hush, now, - he said, -It -(TM)s over at last. - Sarah tried to close her legs only to fail miserably as the muscles in her thighs refused to obey. Laying there with the wetness of her own fluids still seeping out of her now thoroughly punished privates, she sniffed as the headmaster held her hair out of the way. Slowly, after a good minute of crying, she was finally able to climb back to her feet. Stumbling a little, she wiped her eyes one last time and reached for her clothes. -One last thing, - said the headmaster. Slowly, Sarah turned around, her mind already anticipating what the headmaster was about to say. As expected, a moment later, he reached into a drawer to pull out the familiar metal bands of a chastity belt. She winced as he slid it up around her waist and locked it in place. Then, he bent her over again to push a medium sized plug into her bottom. Held in place by the belt, every time she needed it to be removed, she would have to ask to borrow the key. -Two weeks, - said the headmaster, -One week for each time you -(TM)ve been punished. After that, you may come to have it removed. Please do your best to ensure we won -(TM)t have to go for three weeks the next time, however, Ms. Whitney. - He smiled, and striking a match, he bent over his pipe to light it again, and taking in a careful draw, he blew a ring of smoke up over her head. Despite the soreness she felt, and the plug stuck up her rear, Sarah couldn -(TM)t help but smile a little in turn. Even if it was only because she was glad the punishment was over, it still felt nice to do so. Pulling her skirt and her school uniform back into place, she opened the door of the office and left. She would have to return again in two weeks of course, but for now, with her worries behind her, she was finally free. Chapter 2 Mornings started early at the St. Margaret -(TM)s Academy for Wayward Girls, and an hour before the first light of the sun had even broken across the sky, the dormitories were already abuzz with activity. To any visitors who happened to be walking by, it would have been a most industrious sight to see. Hundreds of girls from all over the country, doing their best to rise early and prepare themselves for school. How incredulous, how inspiring. How incredibly proper and charming. Of course, that was only if they were unfamiliar with the inner workings of the academy. For the girls themselves, the reason was far less grandiose. Nobody, not even the most disobedient of the delinquents, wanted to be marked late for their morning inspection of the day. Quick showers were taken, beds hurriedly made, and in between the chiming of the old clock tower at 7:00 am sharp and the first of the morning rays, it was time to begin. Standing in a line and ordered by grade, each girl would raise the front of their skirts in turn as the Sister in charge walked past to check for any signs of nightly sin. A quick swipe with two fingers along the seam of their panties, and a pink slip was handed out to the worst offenders. Then, it was off to the breakfast table for a quick bite before classes could begin. The ritual was of such importance that save for illness, no girl was exempt from attending. For Mary Ellens however, standing in the headmaster -(TM)s office with a sheepish look on her face, that was exactly what had happened. Shuffling her feet around, she handed the headmaster the slip of paper she was holding. Yellow, not pink, thank god for that, but it made little difference all the same. Instead of being caught with her hands between her legs, she had somehow managed to oversleep, and had missed the inspection in its entirety. From his usual place behind his desk, the headmaster looked across at her with a bemused expression on his face. -So let me get this straight, - he said. He stopped briefly, as if even he couldn -(TM)t quite believe what he was saying. -You claim that you were unable to wake up in time because you spent the entire night in a closet instead of your bed, - he said. -No sir, - mumbled Mary, -Not the entire night. Just half of it. - -And how did you end up there in the first place? - asked the headmaster. -I locked myself inside, sir, - said Mary. -By accident? - he asked. Mary looked away, in the silence that followed, the headmaster almost seemed to be at a loss for what to say. Then, to her surprise, he started to laugh, and she felt shame rush up into her face. She was here to be punished, not to be laughed at for her mistakes! Still, even she had to admit that it was the dumbest excuse she had ever used. Or even heard, for the matter. Looking up from where she stood, she did her best to look sorry for herself. The last thing she needed now was to make the situation even more absurd. -Well then, - said the headmaster after some time. The sound of laughter slowly died down, and he dabbed at the corner of his eyes with a handkerchief. -I suppose you -(TM)re here to make penance for your mistake then? - he said. -Yes sir, - said Mary. The headmaster was still smiling, but she felt her heartbeat slowly start to increase in her chest. While not as bad as a pink slip, a yellow slip still warranted a punishment, and she wasn -(TM)t looking forward to sitting down with a sore bottom for the rest of the day. Especially considering that most of the chairs at the school were made of oak. With nothing except the thin material of her skirt to protect her rear, just trying to pay attention in class would be a lesson in futility. For now though, whether her punishment would end up as a spanking seemed to still be up in the air. There was more than just one way for her to repent after all, and leaning back in his chair, the headmaster folded his hands across his chest. Hopefully, he was feeling a little more lenient today. -Alright, I do want to know one last thing though, - he said, -How on earth did you manage to get out? - For obvious reasons, most of the doors at the academy could only be unlocked with the proper key. The fact that many of the students came from wealthy families probably had something to do with it. -I unscrewed the doorknob, sir, - said Mary. -Unscrewed? - said the headmaster. His eyes widened as he leaned forward, and she blushed in turn. -I knew I wouldn -(TM)t be able to pick the lock, but by chance I found a screwdriver inside and so I just thought that-..., - said Mary. In spite of her best intentions, the hole she had dug underneath herself only seemed to grow deeper as it dragged her down. Before she could get a chance to recover however, she was cut off again as the headmaster laughed again. Clasping her hand over her mouth, she tried to preserve what little sanity there was left. The situation was getting more and more ridiculous by the minute, and she only had herself to blame. Whatever her punishment was going to be, it was not going to end well. -That is the first time I -(TM)ve ever heard such an excuse, - said the headmaster. -I -(TM)m sorry sir, - said Mary. -I -(TM)m sure you are, - he said. But a moment later, his smile seemed to fade, and the room grew quieter. -But I assume that unless you have something else to say, then the academy is now in possession of a broken door? - he asked. -I-..., - said Mary. She hadn -(TM)t thought about it that way before, and now she looked down towards the floor in shame. Stuck there in the darkness though, what else was she going to do? Someone was definitely going to have to come around later to fix what she had done. It had taken her an entire half hour of fumbling about to take the handle off, and putting it back together was something well outside her expertise. Not to mention the unknown number of screws she had no doubt lost as well. With the school having been built so far out from the nearest town, she didn -(TM)t even want to think of how much it would cost to drive someone out. -I really am sorry, sir, - she said again. The headmaster looked across at her as if trying to decide, and a long while seemed to pass before he finally made up his mind. -Well, I suppose if it -(TM)s just a door, then I can overlook your behavior just this once, - he finally said. -Thank you, sir! - said Mary. -However, structural damages aside, - the headmaster continued, -There -(TM)s still the issue of your absence this morning. The academy has a rather strict policy on such behavior you know. - In this case the headmaster was correct. And as much as she wanted to believe otherwise, the rules were more than clear on the consequences of missing an inspection, and she had been naïve to think elsewise. Perhaps the headmaster could write off a broken door, but letting her go on such a serious charge was most likely something even he couldn -(TM)t excuse. Whatever hopes she had of escaping without punishment disappeared as she looked back down towards the floor. There was no need for the headmaster to say anything else after that as she slowly reached up to undo the buttons of her uniform. Like every other girl at the academy, she had been punished more than enough times by now that she knew the steps by heart. Setting her school blazer to the side, she stripped free of her skirt. Then, with trembling hands, she lowered her panties down to her knees. -Over the desk now, - said the headmaster. Forcing herself to move, Mary did as she was told. Leaning forward over the smooth grain of the surface, she made herself comfortable the best she could before reaching back behind herself to spread open her cheeks. -Please sir, - she said, -Can I at least pick? - -Pick? - asked the headmaster. Pick, of course, whether she was to have her anus or her clit disciplined today. And bent over the edge of the desk like this with the tight entrance of her ring spread apart between her fingers, it was quite clear which one she preferred. -Oh no, not like that, - said the headmaster. -But sir-..., - said Mary. -What I mean is that your punishment will be quite different from the usual spanking today, - he said again, -You may still keep yourself spread open however, if you think it -(TM)ll make things easier for you. - There was a pause as she tried to understand, and the headmaster reached into the drawer of his desk to take something out. Instead of the leather crop or the cane as she had expected, he held up a small device in the palm of his hand. -This, - said the headmaster, -Is an anal plug. - The toy was small for its size, though given where it was likely to end up, it was still quite larger than she would have preferred. At a little over three inches long and just under an inch or so wide, the sides flared out to form a tapered base, and she swallowed on a dry throat. Compared to a spanking, this almost seemed worse. -Is that-...? - she asked. -Of course, - said the headmaster, -Since you seem to have trouble waking up today, I figured I -(TM)d give you something to keep you awake. - In a strange sort of way, the logic made sense. It was hard to argue against the facts. With something like that shoved up her rear, she would have more than enough reason to stay awake for the rest of the day. Actually being able to focus on her classes, however, was an entirely different matter. -Is there no other way? - asked Mary. -Not unless you want to take fifty with the paddle, - said the headmaster. Well, fifty didn -(TM)t sound so bad... -And ten more on your holes, - said the headmaster again, -Both of them, I -(TM)m afraid. - That was more than enough to get her to shut her mouth, and clenching her teeth together, Mary forced herself to decide. -Thank you for punishing me with a plug sir, - she said. With that out of the way, the headmaster smiled as he got up to walk around the edge of his desk. Running his hands up the inside of her thighs, he used his fingers to feel in between the sensitive folds of her lips. Desperately, Mary prayed that she was still dry. Even if she wasn -(TM)t the one who started it, she could still end up with another infraction if she went past the limits of her permitted arousal. For the next few minutes, she held herself as still as possible while the headmaster teased her around the hidden entrance of her virgin tunnel. Then, satisfied at her abstinence, he moved further upward to press against the puckered entrance of her backdoor. There was the cold touch of lubrication, and then the sensation of something entering her as he pushed the tip of his finger ever so slightly inside. -Ahh-..., - said Mary. It was hard to stop herself as her voice flowed out. Spreading her cheeks apart even further, she forced her bottom up even higher as she tried to escape the intrusion. -Sir, please, not so sudden, - gasped Mary. -Hold still now, - said the headmaster, -You wouldn -(TM)t want me to put it in the wrong hole now, would you? - Judging from the way her insides were starting to clench, it was doubtful whether her body felt the same way. There was no way she could ask for such a thing, however, without also giving up her virginity as well. And with her purity being a requirement for her continued enrollment at the school, her parents would be more than disappointed with her if she did. -Ohhh-..., - said Mary. It seemed like an eternity went by as she lay across the desk, and she breathed out a sigh of relief as the headmaster finally drew his finger back out. It didn -(TM)t last long, however, as he reached for the plug next. -Ready? - he asked. With the only other option being fifty strokes with the paddle, and then ten more upon both her holes, it wasn -(TM)t exactly as if she could say no. -Yes sir, - said Mary, -Thank you, sir. - It was then that the real punishment began. Still keeping cheeks spread apart with her hands, she took a deep breath as the headmaster reached down to press the plug against her backdoor. The tip of the toy slid inside, and aided by the lubrication, the rest of it followed soon after as well. She felt her body stretching around the widest point near the base, and then she gasped as the muscles of her ring squeezed down. The plug was now inside her, but it wasn -(TM)t over just yet. As the headmaster pressed a button, the entire device started to vibrate. Biting down on her lips again, Mary struggled to keep herself still. Between her legs, she could feel the walls of her tunnel clenching down. With nothing to hold on to, however, it didn -(TM)t feel satisfying at all. A minute passed, and then another as the headmaster reached down to run his finger in between the soft contours of her folds, teasing her ever so slightly without letting her spend. -Hold it in now, - he said. Mary tried, she really tried. With the fullness of the plug still stuffed up her rear however, she couldn -(TM)t help but be dragged higher and higher up the mountain and towards the edge. Especially when the headmaster reached down to peel away the hood of her clit. Her nipples were harder than steel now as they pressed against the surface of the table, and she could hear the beat of her pulse pounding in her head. When the headmaster brought his finger back down to circle the entrance of her tunnel again, it took her everything she had to stop her hips from thrusting back against his hand. -Please sir, I can -(TM)t, - she begged. But the headmaster simply shook his head. -Ten minutes, hold it in, - he said, -For every minute you don -(TM)t, it -(TM)ll be a week in chastity. - There was no stronger motivator than that, and Mary clenched her teeth together as she did her best to endure. Nothing worse than being locked in a chastity belt, and even the red-hot touch of the cane was much more preferred. Or in this case, a vibrating plug stuffed up her rear as she bent naked over the edge of a desk. The next ten minutes that passed did so with a slowness that made her wish she had never ended up where she was now. Desperately, she did everything she could to stop herself from going over the edge. Biting down on her lips, digging her fingernails into her hands, it all seemed futile against the constant stimulation between her legs. Still, she held on with a grim determination that only ten weeks of chastity denial could bring about. It was only when the headmaster finally reached for her clit again that she finally broke. -Please sir, not there! I -(TM)m going to cum, - cried Mary. Desperately, she tried to move herself out of his reach, but there was no escaping it as the headmaster reached out to press against the sensitive organ at the top of her lips. Squeezing her eyes shut, she tried her best to hold herself still. By then, however, it was already too late. The walls of her tunnel spasmed once, twice, three times, and then her endurance failed. Mary cried out as every muscle in her body tensed up in preparation for the most wonderful climax she had ever felt. Just before she could go over, however, the headmaster withdrew his hand. -No! - she cried. The only orgasms that were permitted at the St. Margaret -(TM)s Academy for Wayward Girls were those that were given out for good behavior, and bent over the edge of the desk like this with her bottom thrust up into the air, there was no way that she was going to be allowed one now. Out came the leather crop from its drawer as the headmaster raised it high into the air. There was a swish as it fell, and she cried out as it landed squarely against the tender flesh of her virgin hole. Smack! Smack! Smack! Dancing up and down in place, Mary cried out at the thrashing between her legs. She had been so close. Only a few more strokes and she would have been able to go over the edge. With the pain of the impacts landing against her privates, however, there was no way she could finish now. Laying face down, she sobbed as her orgasm was cruelly beaten into submission, even as her hips thrust backwards in frustration against the empty air. Thrust back inside, the long-awaited pleasure was left with nowhere else to go except to swirl endlessly around. Smack! Smack! Smack! Smack! Smack! Smack! It was only after another half-dozen strokes that the headmaster finally lowered his hand, and she cried out softly as he reached out to massage the soreness of her flesh. In her haste to escape, a few of the blows had wandered off course, drifting up and across to where the fullness of the plug filled her backdoor. Those were the ones that hurt the most, and the sudden shock of the crop as it forced the toy further inside had had almost caused her to scream out loud. -Is it over? - she sobbed. -Ten minutes and thirteen seconds, - said the headmaster, -I suppose that -(TM)s enough for today. - Sniffling, Mary wiped away her tears as she lay across the desk. Reaching out for her clothes, she made to take the plug out, but the headmaster stopped her. -No, keep it in, - he said, -You can drop by tomorrow though to have it removed before the start of school. - As if acknowledging what he just said, the plug turned on again, and she jumped as it vibrated softly against her backdoor. A few seconds later, however, she let out a sigh of relief as the power cut out. -It -(TM)ll be a good reminder for you to wake up early as well, - said the headmaster. He smiled as she reached for her panties to slide them back around her waist. With the plug set to stimulate her at random intervals every few minutes now, she would have to be careful to ensure her thoughts stayed pure until it came out. That was easier said than done though with the heat of her arousal still swirling about. Her nipples stood up rock hard from the center of her chest as the headmaster drew the covering of her hood back over her clit. Staring straight ahead at the wall opposite to her, Mary tried to keep her voice down. It felt frustrating to have the tiny nub forced back into the confines of its sheath, but at least it wouldn -(TM)t rub against the inside of her panties as she walked down the hall. There was a chime from the clocktower down the hall, and the headmaster glanced over at his watch. -Fifteen minutes before class starts, - he said, -You better hurry or you -(TM)ll be late again. - -Yes sir, - mumbled Mary. Grabbing the rest of her clothes, she hurried to get dressed and made for the door. The plug shifted inside her as she moved, and she clenched her teeth together as the walls of her tunnel squeezed down. The denial felt almost painful as stimulation blew fresh air over the embers of her pent-up arousal. Looking back over her shoulder, she saw the headmaster waving at her one last time with a smile on his face. Then the door closed, and she had other things to worry about. Like how she was supposed to make it through the day without giving out. Already she could feel herself growing wet again, and there was little doubt her panties would be soaked through by the time lunch came around. The soft vibrations of the plug as it turned on again didn -(TM)t help. Adjusting the toy inside her, Mary slowly set off towards the lecture halls. Her legs ached from where she had bent over the desk, and she had a long day ahead of her still. Chapter 3 Despite the fearsome reputation that the St. Margaret -(TM)s Academy for Wayward Girls had gained for itself over the years, life at the school wasn -(TM)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 -(TM)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 -(TM)t happen again! - An international student, 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. -If my parents ever find out, they -(TM)ll kill me! - she begged. There were tears of desperation in her eyes as if she knew her life was about to end, and given the conservative background she came from, it might as well be the case. A doctor, a lawyer, even an accountant, these things were the norm when it came to the expectations of such families. A harlot, however, was not one of them, and kneeling on the ground right now, that was exactly what she had become. Sitting behind his desk, the headmaster sighed in response. -Do you realize the magnitude of what you -(TM)ve done? - he said. -Sir, I-..., - said Reena. -The issue here isn -(TM)t about just you now, - he said softly, -It -(TM)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 caf(C) 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 -(TM)t have, she really shouldn -(TM)t have, but separated from the controlled supervision of her parents and living halfway across the world, it hadn -(TM)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 -(TM)t taken long for the school to find out. -I -(TM)m really sorry sir, - sobbed Reena. -I -(TM)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 could see her like this now? 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 -(TM)m willing to make an exception. Provided of course that your purity is still intact. - 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 after that 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. -What if I -(TM)m not, - she asked. -Then I -(TM)m afraid I can -(TM)t help you there, - said the headmaster, -On the chance that you still are though, it still won -(TM)t come cheap. Three months of detention, and travel privileges suspended for the rest of the year. - Reena felt a sense of relief. She had been fortunate that sitting side by side in the car that night, she hadn -(TM)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 she was still intact. At least she hoped so. There had been a bit of pain when he stuck his finger in, but it hadn -(TM)t gone in very far at all. Of course, with the only other option being expulsion from the school, it wasn -(TM)t as if she had much of a choice. 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. Still developing, the small pert mounds were hardly large enough to even be considered B-cup in size. -Sir, I-..., - said Reena. -Don -(TM)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 -(TM)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 -(TM)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 -(TM)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. Unless she wanted to risk being expelled though, there was no option left but to continue. 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 as the headmaster reached out to touch her, and his hand trailed up the inside of her thigh. 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. She didn -(TM)t want to, 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 felt awkward to have to expose herself in such a way, but gritting her teeth together, 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. Holding up a camera, he snapped a single picture as proof before turning it around to show her the results. 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 putting it 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 -(TM)t seem as good of an idea as it had once been. The feeling didn -(TM)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 -(TM)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. -Ah! Take it out! Please, take it out! - she begged. The longer it stayed in her, the more it started to hurt, and with every twitch of her insides, the pain only grew worse. She grew distracted again however as the headmaster raised the paddle up and brought it straight down across her rear. Only at the last minute did she 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, -I can -(TM)t! - 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 -(TM)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 from her chest, they rubbed against the smooth grain of the table every time she moved. It must be from the purity inspection earlier, and the shame of having to spread herself apart in such a way. Reena turned her head away in shame. A single drop of clear fluid stretched down between her legs, 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 -(TM)m sorry sir, - she mumbled. -Do I have to discipline you down here as well? - said the headmaster. -Please, you don -(TM)t understand sir, - begged Reena. But the headmaster was beyond listening to her now, and snapping on a pair of latex gloves, he spread her apart 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. Moving it about, he pushed it further inside until it made contact with the barrier of her hymen before 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! - She tried to rise up to run to the bathroom, 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 -(TM)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 her insides 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. As the cane continued to fall across both her cheeks however, the thought was brushed aside as she was thrown once again into the depths of her own personal hell. Crack! Crack! Crack! Crack! Crack! An entire eon seemed to pass as Reena lay naked 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 -(TM)t spared as the headmaster moved the cane down every now and then, and Reena whimpered as it took her by surprise. It was only after losing track of the number of strokes more times than she could count that the headmaster finally relented. 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 -(TM)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, as if the universe was trying to torment her, 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 -(TM)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 -(TM)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 -(TM)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 -(TM)t as if she had much of a choice now 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 -(TM)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 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. Stepping forward from behind, the headmaster placed his hands on her shoulders, and she whimpered as the pressure pushed her further down. -Ready? - asked the headmaster. Her clit twitched in response at the fullness of the foreign object inside her rear. With nothing to hold onto, the walls of her empty tunnel flexed in turn. -Yes sir, - lied Reena. -Good, then you may begin, - said the headmaster. Reaching out to pick up the pen, Reena turned to the first page of 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 debt 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 -(TM)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 ones 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 for as long as she was still at the academy. 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.