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Another erotic story from the FLOGMASTER!

Copyright 1985-2016 by the Flogmaster. All Rights Reserved. Free distribution via electronic medium (i.e. the internet or electronic BBS) is permitted as long as the text is _not_ modified and this copyright is included, but _no_ other form of publication is allowed without written permission. This document _may_ contain explicit material of an ADULT nature. ***READ AT YOUR OWN RISK!*** Anything offensive is your own problem. This story is for **entertainment** purposes only, and it does _not_ necessarily represent the viewpoint of the author or the electronic source where this was obtained. All characters are *fictional* -- any resemblance to real people is purely coincidental.

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(****, M/f, Edgy, nc caning, anal sex)

A headmaster severely punishes a sexy student. (Approximately 3,147 words. Originally published 2004-01.)

I was absorbed in my Agatha Christie mystery and the fifteen-year-old girl was so quiet that she must have been standing there for several seconds before I became aware. I suddenly looked up, startled.

"Chelsea!" I exclaimed. I was delighted. Chelsea's one of my favorites. She's a stunning beauty with dark hair and a round face dominated by a killer smile. Of course she wasn't smiling now.

She looked up at me briefly, her brown eyes wide and nervous, her lower lip caught under the bite of a row of white teeth.

"There now, dear Chelsea, it can't be all that bad, can it Sweetie?"

Her mouth opened, then shut, and she silently handed over the yellow punishment slip. Her slender arms folded protectively across the swelling bumps of her chest, and wet tears glistened in her eyes. She looked away, her young body shaking with faint trembles.

The paper explained everything. Dear Chelsea, sweet innocent Chelsea, had skipped her Geometry class. Worse, she had done it with a forged doctor's note. That would also require punishment.

"Oh dear," I said gently. "It looks like you've been a naughty girl." She just stared at the floor, unable to look at me. She was such a wonderful mixture of apprehension, contrition, and delicious schoolgirl that I found my mouth watering in anticipation.

I motioned her to turn around, loving the way the skirt of her uniform hung off the swell of her hips and jut of her ass. There was a nice gap between the material and the back of her legs. Chelsea was growing fast: this was surely last year's uniform, for the skirt didn't reach her knees, giving her the appearance of a big girl in a little girl's outfit.

I slipped my hands under her dark green skirt to palm the mounds of her ass. Chelsea has a splendid ass, firm with youth yet plump and swelling with newfound femininity. As I squeezed and kneaded the cheeks, I gently scolded and teased her, saying things like "I hope it was worth it."

She was crying when I unbuttoned her skirt at the back and let it drop into a dark green puddle around her ankles. Her white panties were glorious, hugging her hips tightly, framing the round ball of her butt to perfection. My erection swelled.

"Oh please, Mr. Lancaster. Please!" They were the first words she'd spoken since entering, a faint whisper, her voice trembling with fear and emotion.

"Hush now, darling. You know there's nothing I can do. You did the crime, you'll now have to do the time."

Her shoulders shuddered and her head went down, her entire posture one of defeat. I patted her rump to turn her around again, studying her from the front. She truly was a delicious girl, so sweet and slender, womanhood blossoming before my eyes. In the dark green jacket and white blouse she looked polished and sophisticated, a look that conflicted with the obvious youth of her face. Below the waist was the brief vee of white panties, framed by stout columns of white thighs leading to slender ankles and petite feet clad with white stockings and black pumps. Oh, she was a treasure this one.

"Chelsea," I said firmly, to get her attention. "Do you need a spanking to break you in slowly or shall we just get it over with?"

Technically, a spanking was against the rules. She'd been sent to me for a thrashing and it was supposed to be strict. But I often spanked, if the girl wanted it, for it was immensely enjoyable for me and it usually calmed a nervous girl. It stung a bit, but warmed the flesh and made the caning to come easier to bear.

Chelsea gave the briefest nod, and she didn't resist when I led her to the small sofa. I seated myself and drew her across my lap. She was a good-sized girl for her age, approaching five and a half feet tall. Her body was absurdly perfect, toned with no flab yet femininely curvy. Her ass was incredible, plump and round, two proud cheeks jutting upward and straining against the confines of her cotton underpants.

For a moment, I played with her bottom. I squeezed and petted the cheeks all over, sliding my hand from top to bottom and over her hips. Finally, I began to tug the panties down. I took my time, enjoying the way the flesh was slowly unveiled, and delighting in Chelsea's nervous wiggles across my lap.

First the subtle slopes of the tops of her bottoms appeared, the skin a slightly paler shade of pink. Then came the petite crack, the divider. As the panties descended, more and more cheek became visible, the round plumpness of the mounds obvious. The crack was strongly delineated, each buttock curling beautifully into the deep crevice. Chelsea's skin was smooth and flawless, and once the undergarment was pulled to mid-thigh, it seemed like there were acres of buttery flesh just waiting for the sting of my palm.

While beautiful in every aspect, the sweetest part of Chelsea's caboose was the join between buttock and thigh. Her thighs weren't skinny or fat, but stout columns of youthful health and vitality. Each connected to the impressive orb of buttock with a gradual swelling of flesh without a crease. The intersection between the cheeks made a perfect diamond shape, inside which I could glimpse the puffy lips of the sweet girl's sex, several tuffs of dark hair promising what would eventually be a luscious bush.

I placed a palm on Chelsea's left buttock, allowing my hand to conform to its shape. I kept it there for a moment, enjoying the feeling. I could faintly feel Chelsea's ass trembling. When I was ready, I lifted my hand and began to spank. The flesh bounced nicely, ripples of force echoing through the taut skin. I didn't spare her, but spanked her hard, and she wiggled and gave a light gasp as the sting mounted. After just a few spanks her skin was a pale pink, soon blossoming to a warm magenta. I spanked her bottom all over until her whole butt was nice and toasty. Then I paused, letting my hand caress the warm skin.

She lay quietly, breathing heavily, her body quivering against me. Gradually the tension mounted as what she dreaded grew near. Finally I gave her bottom one last hearty wallop and guided her to her feet. It was time for the cane.

As she stood, I glimpsed her front and saw the sweetest little dell, covered only by a slight vee of brown fur. Unlike women who shave, this was true innocence and I had to restrain an impulse to pet it. I looked at her face and was moved, for she was teary-eyed and frightened, but trying to be brave. She was so pretty, her face friendly and open and kind. I had to remind myself that she was a very naughty girl and deserved her punishment.

I guided her to the whipping table. This wooden structure consisted of a slanted board across which a girl was made to lay. It's height was adjustable, and took my time setting it so the lowest portion was pointing just above Chelsea's snatch. When she bent forward across the table, this had the effect of putting her on her tiptoes, which thrust out her rump deliciously. It also prevented her from being able to clench her gluts muscles, which would generate undesirable bruising.

With Chelsea on her toes and waiting, I went to my selection of canes. At fifteen, and considering the severity of her crime, Chelsea was going to get a senior cane. The question was, which one? The seniors are all thicker and longer, but I had several different makes, some old, some new, and the effect of each is subtly different. With so many strokes to administer, I decided I needed a cane that was whippier, causing more sting, so I rejected some of the older, stiff classics. I chose a recent addition, thirty-six inches long, tough and wiry, with a wicked bend.

Chelsea was looking at me imploringly over her shoulder, watching as I approached. She looked positively scrumptious, naked from the waist down, panties in a bunch at her ankles. Her round bottom mooned outward, its hot-pink flesh just begging for stripes. Strands of her disheveled hair had fallen over the side of her face and her beautiful eyes peered at me desperately through them.

"Sir, please..." she whispered.

"What is it?" As I spoke, I bent and helped Chelsea step out of her panties. I laid them on a nearby coffee table.

"Please, I know I have to be whipped, but I don't... I mean, you don't have to... you know."

"Chelsea, Chelsea, Chelsea. You are so darling. Of course I must. It's part of your punishment and I don't want to hear another word about it. In fact, with a long session like you've got coming, I might even do it twice."

The girl groaned. "Oh no! Please, sir, I beg you... cane me extra, just don't--"

"That's it!" I said sharply, swishing the cane through the air. "You just earned yourself four extra strokes, young lady. Now close your mouth and profit from your discipline."

Obediently she went quiet, but I could see it was a struggle. I knew why. Chelsea, you see, is very tight. Though she's already developing hips and has a marvelous ass, she's still a young girl. She hasn't been stretched enough. I knew from our previous sessions that I would enjoy what was to come far more than her.

I decided to go slow with the caning and see if I couldn't maybe do her three times. I was already hard, but I wanted a few stripes for me to rub against.

The first stroke was low, about an inch above the join. The flesh was so meaty and tender there and the welt that rose up was glorious. Chelsea reacted as though I'd plugged her into an electric outlet. She tensed, writhed in place, and a soft whimper escaped her lips. She was silent during the second cut, which was right next to the first. The third was a little lower yet, the three weals swelling like rising dough and touching each other.

I paused, bending forward to study the marks. They were scarlet with dark crimson edges, like a crust. The far end, where the tip of the rod had sunk in, was purplish. Lovely. Chelsea quivered and danced, waving her bum from left to right as she tried to absorb the frightful sting. My cock was like a steel bar, and I decided it was time to get the quick one over with.

Releasing it from my pants, I approached Chelsea from behind. She moaned when I put my hand on her left hip to steady her.

"Oh!" she gasped, and I could hear tears in her voice.

I didn't say anything but slipped my penis between her legs, rubbing it against her sleek thighs. Her body danced against mine, not moving that much, but providing me with wonderful sensations. I pried open her cheeks then, ignoring her gasp of pain when my hands clenched her wealed skin. There, nestled between the wonderful round mountains, was the dot of my target.

As I expected, it was a difficult entrance. Chelsea was tight and not especially cooperative. But I gripped an asscheek in each hand and guided her, poking her most cruelly. Lord she was tight. It took me considerable effort to move in, but I did it, my dick aroused by her cries of pain. Once I was all the way, a little rhythm got me slowly moving, back and forth, in and out. Chelsea was crying and I told her to be quiet, that it was only this painful because she hadn't had enough experience.

The effect of everything -- sweet naked girl, round rump wealed with three delectable stripes, and the tight hole -- had me sperming in just a couple minutes. I had expected it, for I'd been hard since Chelsea came in the door. I finally pulled out, panting, and let Chelsea clean me off with her tongue. Then it was time for more cane.

The strokes were as brutal as I could make them. I didn't use all my strength because that's not what makes a caning hurt: it's all in the technique. I struck hard, timing my blows to the downslope of the previous pain, and I used my wrist to flick in the rod, giving it that extra intense sting at the end. I was careful about placement, striking untarnished areas first, and making judicious use of the cane tip, using it to indent the fleshiest portions of her butt.

By the seventh stroke Chelsea was struggling. She was crying silently, tears dripping from her shining face, her mouth clenched in agony. She gripped the table furiously, her hips rocking as she rode out the pain. To her credit she didn't kick her feet and flail, as some of the girls do, but then her punishment was just beginning.

After the tenth stroke I paused, Chelsea panting with relief at the break. Her bottom was beautifully marked with rows and rows of crisp tramlines. I saw with concern that I had pretty much run out of virgin land: future stripes would have to cross these, and that was going to sting a bit.

To my surprise, I was already randy, my cock stiff and eager. The thought of plunging back into such a sweet girl had my balls aching, and I decided to go ahead and do her again. It was risky, for I wasn't sure I could be ready for a third by the time the thrashing was done, and I prefer to end a beating with a good fucking, but I decided to risk it.

This time it was a little easier getting in, though Chelsea moaned and protested the intrusion. Once in, I had more movement and I was able to really give her a good fucking. I pushed up into her guts, really driving it in, causing her to squeal in alarm. I slammed myself in to the balls, my hips and belly pressing against her burning ass. I could feel the heat radiate from her and it made me excited. The weals were tender and pressure against them made Chelsea squirm and wiggle, which was wonderful while she was impaled upon my shaft. I encouraged her movements with non-gentle pinches and held out as long as I good. It was shorter than ten minutes, but definitely longer than five. Then I was spurting, hot semen pouring from me and splashing against her insides.

I was actually sore when pulled out. I'd worked hard for that come and it had been wonderful. I told Chelsea to be gentle as she licked me clean, but she was crying so much it took her a long while. That was fine with me as I wanted time to recover myself. Eventually the warm wetness of her tongue caused a stirring and I felt my penis awaken again. I ordered her back across the table and prepared to finish her whipping.

I was enjoying Chelsea's beating so much an evil part of me wished it could last all day, but I knew there were only ten strokes left. I would have to make each of them count.

I went to Chelsea's right side and prepared to cane her from the other side. I wasn't quite as strong from this side, though technique mostly made up for that, but I was determined to give the girl a balanced bottom with the tip gouging into both cheeks equally. As the stripes mounted, purple weals throbbing, Chelsea was having a more and more difficult time bearing the beating. She cried out loud now, writhed openly, and twice got out of position to beg me to not cut her so deep.

Technically, I could have beaten her extra, but she was already due twenty, including the four I'd added, so I had mercy and didn't extend her punishment.

But seeing such a pretty girl in so much agony made me hard again. Her bottom was well-thrashed when I reached the final stroke, and I knew I was ready for a third dig. I parted her cheeks as she cried out and plunged in, right to the hilt. Her body was extremely animated this time, which was incredible. She writhed, slid up and down the table, raised herself up and then lay back down. She moaned, cried, and whined, gasping when I lifted her to her toes with a deep thrust.

I played with her ass as I fucked her, squeezing the purple weals on the edges of her buttocks, pinching the flesh cruelly and making her dance in a frenzy of suffering.

"Have you learned your lesson?" I asked sternly as I thrust repeatedly into her.

"Yea-yea-yes," she chattered, her teeth rattling as I rocked her.

"No more fake doctor's notes?"

"Nnn-nnn-nooo," she moaned.

"No more skipping class?"


"Good," I grunted, and with one final plunge, exploded inside her. There certainly wasn't as much come this time, but what there was was still hot and gooey, and Chelsea felt it inside her. When I emerged, her hole was bright red and painfully open, and streams of white fluid dripped lazily from it.

I sighed with relief as she cleaned, while she sobbed, just glad the ordeal was over. I handed her a box of tissues when she was done, and she gratefully dabbed her eyes and wiped her face.

"A good whipping?" I asked.

Her face was pale. "Very thorough, sir. Thank you."

"You felt it, did you?"

"Every lash." She winced, glancing over her shoulder, trying to look at her battered ass.

"Your ass feel properly hollowed out and punished?"

"Oh, definitely, sir! Three times!"

"Good. That ought to teach you to complain about discipline and ask for exemptions. I have a mind that I'll give it to you at least twice every time you come in here."

Her eyes showed her fear, but her pasted-on smile was all obedience. "Yes sir. Thank you sir."

"You need the practice, Chelsea. You're damn tight."

"I'm sorry."

"You're young. Still, I think I'll speak to the Head about having you in for some practice sessions. Those marks'll be tender for the next week at least, so maybe be we can get in a couple sessions before they fade."

Chelsea looked distraught, but smiled nervously. "Yes sir."

I watched with immense satisfaction as she put her panties and skirt back on, and left to resume her normal class schedule. Damn she was hot.

The End

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