Headmasters Rules
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The Headmaster's Office free porn video
The headmaster’s office was a small, unassuming room located near the eastern side of the St. Margaret’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. She was eighteen now, what was there for her to be afraid of?
“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’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’t even control. Had she been a just little faster at getting changed today, then perhaps Sister Halsey wouldn’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’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’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’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’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’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’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’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’ll have to find out the answer to that together, won’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’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’t-…”
I didn’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 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’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’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’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’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’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’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’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’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’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’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’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’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’ve been punished. After that, you may come to have it removed. Please do your best to ensure we won’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’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.
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