Teaching the Tomboy

by Tasty Little Pop Tart

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft, Consensual, NonConsensual, Reluctant, Spanking, Anal Sex, .

Desc: Erotica Sex Story: A punishment story with a twist. Sara is dragged before the headmaster for yet another spanking over the discipline rack. This time, however, Sara's punishment takes on a more personal note. It turns out to be unlike anything either she or the headmaster envisioned.

Based on the short story:
SARA'S PUNISHMENT
By Mr. Stefens

The three buxom matrons marched Sara into the punishment room, one on either arm, the third trailing behind with a scowl on her face.

"Get offa me!" Sara protested stridently as the two large women marched her toward the discipline horse. How delightful it was to encounter Sara again--and so soon.

"Strap her down," I ordered with a sigh.

While Sara twisted and struggled and mouthed indecipherable words at her tormentors, I sat against the edge of my mahogany desk and watched with a false expression of boredom. Inside, I was alight at the prospect of being alone with my tomboy again.

Sara was an anomaly at our little school. Recently transferred from St. Jude's School for Girls in Piscataway, New Jersey, she was a hesitant troublemaker. Hesitant, in that she made trouble only when provoked, which appeared to be all too often, and certainly one of the reasons she was with us now instead of with her former teachers.

The problem was, Sara was the proverbial tomboy. Tall in stature--5'9" if I remembered correctly from her records--slim of build and awkward, both physically, and in her relationships with the other students, she had ridiculously short, sandy brown hair, a long but surprisingly attractive face, a freckled complexion, and features that she refused to enhance with any kind of makeup. Because of her appearance, our male and female students alike teased Sara mercilessly, responding too often to that teasing with her fists.

The two burly matrons positioned--hoisted, truthfully--Sara onto the wide padded back of the horse and, while holding her in position, the third matron secured Sara's wrists in the padded leather cuffs positioned at the bottom of the stout oak legs. That done, she strapped the wide leather belt around Sara's waist, and then secured her ankles in the provided leather anklets at the back of the kneeboards. Sara, despite her protestations, was rendered immobile.

"Thank you Ladies," I said evenly. "You may leave now."

Scowling but obedient, the three brawny matrons marched single file to the door and exited it, the last, the charge matron, throwing a last glance at the defiantly struggling student. Nodding to me curtly once, she swung the door closed behind her. Sara and I were alone.

"So, what brings you back here today, Sara dear?" I asked conversationally.

Sara struggled fruitlessly against the leather cufflets and the belt, the same as she always did. "Nothing!" she cried vehemently. "I didn't do nothin'!"

"I did nothing," I corrected absentmindedly. Pushing off from the desk, I crossed the room to where she lay horizontally atop the horse. It was my favorite piece of furniture in the world, and the student body's worst nightmare. No student at St. Augustus's Catholic Prep School wanted to visit this office. Some few, those like Sara and her rowdy cohorts, did anyway.

Sara was eighteen years old, in the 12th grade. Her current period was Algebra with Sister Mary Ellen if I remembered right, her fifth period of the day. A grin suddenly stretched my face, remembering that old joke about the red schoolhouse: You'd be red too, if you had eight periods a day. I suppressed a chortle.

"Okay," I began again. "What infraction didn't you commit this time?"

Grumbling incoherently, Sara yanked one hand, then the other against the tough leather cuffs. By the time she limped out of this room an hour or so from now, her wrists and ankles would all be angrily raw, despite the heavy padding on the cuffs. I sighed, thinking of the stupidity of it.

"Do I have to call Sister Mary Ellen?" I asked patiently.

"Call anybody you want!" she shouted back, yanking both of her hands at the same time. Then she realized what she'd done and became motionless. "Sorry," she said hurriedly, too late.

As did all our students, Sara wore the required white button-down blouse and a gray woolen skirt. Her knee socks were the regulation Wednesday red and gray, and her shoes a perfectly shined black Raising the back of her skirt and laying it across her back, then lowering the back of her plain white panties to the bottom of her slim but nicely rounded white buttocks, I listened to her moan of frustration.

"I'm sorry, Reverend Father," she pleaded miserably. "I didn't mean that to come out the way it did. Please forgive me. Please?"

"You have your choice of a cane or a wooden paddle," I advised.

I always left the choice to the students. It gave them a sense of involvement in the decision making process. There was also the leather strap to consider, and the tawes and the flexible paddle, but for the sake of brevity, one had to limit their choices. Otherwise, the student would paralyze herself with indecision.

"Please, Reverend Father!" she begged. "I haven't done anything wrong!" Frantically wild-eyed, she looked back over her shoulder at me. Her last punishment had been via the cane, and faced now with this decision, she certainly remembered that punishment. All anger and bluster had disappeared from her. She was now just a scared little tomboy about to be spanked. Or so she thought.

"Actually," I said, "I have something different in mind for you today." Placing my hand on her fine young bottom, I let it glide over the warm flesh, untouched by any sunlight and oh, so pleasingly white.

Sara gasped loudly. "Reverend Father! What are you doing?" Her eyes were no longer pleading but shocked.

Other than bare her rear end the last time she was here, my hands had never touched her body. Now my right hand was caressing her in a most intimate way. When I let my fingertips glide down the valley between her buttocks and briefly touch her soft, defenseless privates, she shuddered violently.

"Reverend Father!" she whimpered. "You can't do that! It's--"

I unzipped my trousers and grinned, listening to her gasp again. Though formed into a comical looking O, her lips trembled, as did the rest of her body. As I removed myself from my trousers and displayed what I had waiting for her, both her eyes and her O-shaped mouth grew appreciably wider.

"This should make your punishment very interesting," I said, stroking myself to maximum hardness.

"No!" she objected in a terrified little squeak.

Taking it to the front of the horse, I climbed the footstool I kept there for just this purpose and let her examine it at close range. Stroking her short brown hair, I said to her: "I'm so going to enjoy having you suck this, my little troublemaker. But I'll save that treat for later, after you've taken the first half of your punishment."

Terrified and shaking uncontrollably, all Sara could do was stare at my magnificent cock head with her bugged out eyes. She had not even the presence of mind to close her mouth, still held in that comical looking O. How I wished to stick myself into that warm wet opening, to experience the feel of those trembling lips and untested tongue, but that would come later. Restraint in all matters was what I preached, and I followed my own teachings.

Stepping down from the stool, I walked to my desk and pulled the chair out from beneath it and wheeled it over to Sara. She had begun her struggling again, with a renewed fervor now, but that would pose no problem. The wide leather belt kept her hips and buttocks very tightly in place. She could struggle all she pleased while I still enjoyed myself. Sitting down, I leaned forward and smelled the wonderful bouquet emanating from her rear end. It was divine, truly magnificent. Unsavored as yet, I hoped, by any other male. Gently, I placed my lips on her right buttock and gave it a kiss, then kissed the other. Sara gasped loudly.

"No!" she cried again. "Reverend Father, don't!"

I answered by licking up the valley between her buttocks and them kissing them both wetly again. Sara froze in place, breath sucking into her lungs in a sharp gasp as I spread her cheeks and exposed the tight little orifice hidden between them. It was small and pink and clenched tightly shut, as of course, it should be. Being exposed to the air made it clench even tighter still. As I leaned forward, I wondered if she'd ever imagined a tongue about to do this.

"Reverend Father! NO!" she screeched in shock. Although hidden from me, I felt through the twist of her body that she was now craning her head to look back over her shoulder, incredulous eyes and mouth both wide in shocked disbelief that any man would touch her there. Not just kiss, but lick and tickle it lovingly as I was now doing with my tongue. So shocked was she, that for the moment, she had forgotten to struggle. Only eighteen, she had so much to learn.

While Sara resumed her struggles, I settled in for a thoroughly enjoyable five minutes of licking, kissing, tickling, and penetrating her with my tongue. I stopped only when the strain in my muscles became apparent, and then I settled for kissing and licking her gently. I left no portion of her anatomy untouched, though, due to her positioning, I was unable to reach as far forward as her clitoris, which I wanted badly. I did thoroughly enjoy the time spent inside her vagina; however, by now convinced that she was indeed, a virgin. Her hymen, that thin little protector of virtue, was surprisingly unbroken. Though it made me sad, I decided that her virginity should remain intact. I had responsibilities to my students, after all.

I continued my kisses down the inside of her thighs and up the backs of them to return to her buttocks, and the pink flower between them. I have to admit a certain fascination (obsession?) with the female anus, and Sara was not the first student I had explored this fascination with. She was, perhaps, the most desirable however, and that made it hard on my self-control. If nothing else, the duties of a Reverend Father are all about self-control.

Rising, I returned to my desk and slid out the lower right hand drawer. Lifting out a tidy stack of folders, I removed the bottle of K-Y Personal Lubricant and a handful of paper towels kept just for these occasions. For a moment I studied the box of condoms, then slid the drawer closed and returned to Sara's bare rear end. I had no doubt my little virgin was free of any infection, and of course, I was. Besides, I intended to sodomize her only, not engage in sexual intercourse with her. I really had no need of a condom.

"I'm about to lubricate your rear end with K-Y Personal Lubricant," I informed her appropriately. "I--"

"No!" she wailed. "You can't do that!"

Unbothered by the interruption, I continued: "I don't want you upset wondering what I was about to do. I'll make sure you're well lubricated and ready for me before I insert myself. I don't want this any more painful for you than necessary, Sara."

"No, please," she whimpered miserably. "I don't want to do this. Please, Reverend Father."

"Should have thought about that before misbehaving today, Sara. Remember the last time I saw you? I made it very clear that your next punishment would be much more severe than what you had just received. You remember I told you that, correct?"

"Yes," she agreed miserably. "But I didn't think..." She broke into tears and sobbed out the words: "But I didn't think you would rape me."

I spread her buttocks and squeezed a stream of the clear liquid into the valley between her cheeks and onto her little pink vortex. She tried hard, of course, to squeeze her buttocks closed, but her position over the discipline horse made that difficult. Her eyes staring back at me continued to be hugely round, as did her delicate mouth. I thought again of how badly I wanted to plug it with my huge cock. She clenched again and moaned pitifully as I spread the lubricant around her pink hole with my fingertip.

"You've never been sodomized before, correct?" I kept my voice casual, as my middle finger was about to penetrate her rear end.

"Of course not!" she sobbed. "I've never done anything!"

"Nothing?" I repeated, though in the negative.

"Nothing!" she wailed in response. My fingertip was inside her to the first joint and I rotated it back and forth to completely lubricate her passageway. I removed it as she yanked her hands uselessly against the restraints and again attempted to clench her buttocks closed, while at the same time emitting a cry of frustration.

"Please stop!" she wailed at full volume. "I don't want to do this!"

I had no fears of her protestations being heard. This room was used specifically for the agonized shouts of frenzied young ladies--though admittedly, shouts of a different nature--and the heavy soundproofing behind the cedar paneling allowed not a whisper to be heard outside these walls. It was not fair to disrupt classes and cause anxiety amongst the other students.

Turning my hand palm upward, I dribbled more lubricant onto my middle fingertip, which pressed lightly against the bud of her anus. While the lubricant continued to drip onto my finger, I worked it into her anus and the beginning of her rectum. I twisted and turned my finger so that all surfaces were equally lubricated. While I did this, she continued to moan loudly and fight against the leather restraints. I so wished she wouldn't attempt to hurt herself.

"Please keep still, Sara," I advised. "The less you struggle, the less hurtful this will be for you. You don't want me to hurt you, do you?"

It would be hurtful no matter what she did, nor what I did for that matter. My cock was monstrous and would cause her great discomfort until she grew used to it. Most girls never grew used too it, however, but simply cried and wailed and sobbed while I enjoyed them. Sara, I was sure, would be no exception I stood up and prepared to mount her.

"Oh, please," she begged. "Please ... don't ... do ... this."

Her words came out broken by her sobs. I felt a stab of compassion for the poor girl, but I pressed my cock head against her anus anyway.

"Take a deep breath and hold it," I advised her. "This will be difficult, but I'll be as gentle with you as I can."

I was always gentle. Until I got myself completely in them and the testosterone took over, maddening me, and then it was make the girl wail and scream and whimper and sob as hard as I could. I always fought this animalistic behavior in myself, but unfortunately, I always lost. Perhaps with Sara it would be different. Perhaps.

Surprisingly, Sara inhaled deeply and complied with my advice on holding her breath. In and of itself, this was unusual. Most often the young lady was too hysterical to accept advice of any kind. This encouraged me about Sara and I honestly went about her penetration with unusual gentleness. Instead of pushing myself into her halfway and letting her scream herself out as usual, I stopped with my cock head only halfway inside, allowing her to moan softly for a few moments, and then took occupancy of her anal canal with deliberate slowness. To her credit, Sara clenched her teeth and sucked breath between them until the intense pain of her violation eased a bit. Then she let it out in a loud exhalation and collapsed onto the discipline horse, as though exhausted.

"Are you all right?" I asked worriedly.

"What do you think?" she grumbled back. "I have a cock up my ass."

"Sara," I chastised. "You shouldn't talk like that. It's demeaning."

She raised her head from the padded back and looked at me over her shoulder. "You're raping me. I should be concerned about my language?"

I felt a sharp pang of guilt. "You're being punished," I corrected. "For your atrocious behavior."

She rolled her eyes and put her head back on the padding. "Whatever," she muttered, startling me. "Just get it over with and let me go home."

It was my turn to stare in wide-eyed disbelief. Momentarily at a loss for words, I said the first thing that came into my head.

"What did you do wrong? Why are you here today?"

She seemed both amused and chagrined that I didn't know the answer.

"I punched a boy in the mouth for calling me a dyke."

I had unknowingly pushed myself another inch farther into her rectum and I halted myself. "Who said this to you?" I demanded.

"Tommy Reynolds," she said sullenly.

I noticed that she had raised her hips a bit to make her penetration less painful and surprisingly, was rotating them just a little. I couldn't tell if this was also to mitigate the pain, or because she was unknowingly enjoying it. I blinked slowly, more than a little confused.

"I'll have a talk with our young Mr. Reynolds," I announced, more to myself than to the immobile Sara. "But you were just as incorrect, Sara, hitting the boy in the mouth. Violence is never the answer. Violence only begets more violence."

"Humph!" she responded gruffly. "Violence is the only answer some people listen to. He had no right saying that about me. It hurt."

"You're not a lesbian then?" I had become entranced by the slow rotation of her white buttocks. She was seemingly unaware of it, or too angry to notice. I pressed forward into her another inch experimentally.

"No!" she hissed through her clenched teeth. There was no question that my presence inside was hurting her, but she seemed more concerned about her sexual identity than her sexual violation. "I am not a lesbian!"

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Story tagged with:
Ma/ft / Consensual / NonConsensual / Reluctant / Spanking / Anal Sex /