The Headmaster   added 3 years ago    

  By: sexhopper69

What can I say; I'm feeling creatively bereft these days. Can't finish one goddamn story I start (and I've got 4 of them going).


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Naughty level to be set later

So I decided to repost my Headmaster stories, partly because I'm fond of them- this was the first spanking -oriented piece I ever wrote, and it remains a personal fantasy fave, and partly because I had a few e-mail requests for a repost.

Usual disclaimers- this story is sexually explicit and is meant for adults.

* * *

I am sitting in the principal's office of the exclusive girls academy I attend. I'm feeling nervous and rebellious; I've been sent to Dr.Mullen's office because my headmistress discovered me kissing one of the stable boys. Dr. Mullen has a reputation for stern discipline.

The chair that I sit in is wooden and austere, stiff backed, without a cushion; it is quite uncomfortable, and I squirm restlessly, waiting for you to arrive, anxious about what form my punishment will take. Suddenly I hear the door behind me open, and I stiffen nervously as you shut the door, then take your seat behind the desk. My head is bowed;

I'm unable to look at you.

"Raise your head, Michele, and look at me," your voice is soft but commanding, brooking no opposition, but I'm unable to obey. Again I hear your voice.

"Michele," and now your voice is softer, but paradoxically sterner; I realize that further disobedience may worsen my punishment, and so reluctantly I raise my head and meet your gaze.

"Michele, do you know why you're here?" you ask me, and I nod dumbly, too nervous to speak.

"Well?" you prompt, demanding an answer.

My hands twist nervously in my lap and I stutter, "I kissed a stable boy. Mrs. Harris saw us."

You shake your head slowly. "You're here to learn discipline. Discipline and self-control."

I start at these words as a tension that is not merely nervousness surges through my body. Suddenly I feel heated. Flushed. You continue.

"What concerns me is your . . . impulsiveness, your inability or unwillingness to control your desires. However, I recognize that part of a schoolmaster's job involves teaching you self-control, providing discipline. In fact, you might say that discipline is a vocation of mine." You smile meaningfully, then stand up abruptly.

"First things first, though. Before proceeding with your discipline, I'll have to examine you, to see precisely what damage this stable boy has done."

I jump from my seat, distraught. "But-but- he just kissed me. Nothing more! I swear!"

You interrupt me. "How am I to believe someone who has so little self-control? How are you to be trusted? Most importantly, if we're to begin reining in those wayward desires of yours, it's essential that I understand and explore them." Moving away from the desk you beckon to me.

"Come with me. We'll use my private study."

Having no choice, I follow you from your office, down a hallway, until we reach your rooms. Opening the door, you beckon for me to enter. The room is lushly appointed, richly carpeted and finely furnished. A fire glows warmly in the stone fireplace. You close the door behind us and I hear the click as the lock slides into place. Sitting down on a padded armless chair you ask me to sit on the small footstool directly in front of you. I comply.

"Remove your blouse." Your voice brooks no disobedience, and with shaking fingers I begin to slide the buttons from their holes, one by one. I find, however, that I'm unable to actually slip the blouse from my shoulders.

"Michele." Your voice, while quiet, carries the unmistakeable ring of authority, and a subtle warning. I daren't risk your impatience. With shaking hands I remove my white cotton blouse, and now I sit before you in my bra. You nod for me to continue. Slowly I slide the bra straps from my shoulders, then my hands move behind my back to undo the clasp. I let the lingerie drop to my lap and I cover my exposed breasts with protective, sheltering hands. Annoyed, you gesture at me, your meaning impossible to misinterpret, and I drop my hands to my sides, revealing the fullness of my breasts to you.

"Did he touch your breasts?" I shake my head in nervous denial.

You regard me disbelievingly. "Your nipples-they're erect, swollen. Surely the boy touched them."

Your hands reach out toward me, each grasping a breast in a firm caress. Your thumbs slide around the nipples, hardening them further.

Taking each breast tip between thumb and forefinger you begin to pull, gently at first, then more demandingly, worrying and pinching the rigid flesh.

"Like this, Michele? Did he touch you like this?" Again I shake my head, nervousness making my tummy churn. You reach under my arms and pull me onto your lap so that my legs straddle yours. I can feel your erection beneath me. Your mouth descends to my right breast and you suck strongly at the nipple, even as your other hand ensures that the other rubbery breast tip is not neglected. You pull and suck on both nipples strongly, rhythmically. I'm breathing heavily, chest rising and falling, bewildered and excited by the sharp ache that surges through me.

"How quickly you are aroused," you chide me, smiling knowingly, and I bow my head, ashamed by the desires I feel rising inside me. Your fingers continue to flick and pinch my nipples, grown impossibly tight and swollen. Abruptly you push me upwards, so that I am standing again.

"Take off your skirt." Your command is brusque, abrupt. With shaking fingers I unzip, then slide, the skirt from my hips, so that I am standing before you, naked except for my schoolgirl socks and white cotton panties. You gesture for me to remove my socks and awkwardly I do so.

"Bend over my knee." Your voice, still full of authority, demanding compliance, has a softer, seductive timbre, and I find myself eagerly obeying you. Somewhat clumsily I drape myself across your legs, still clad in my panties, my hands resting on the carpet to support me. I am dizzy and flushed, disoriented by this awkward, shaming position. I pull my legs tightly together.

I feel your hands on my backside, positioning me. Readying me.

"Spread your legs, Michele." With a muted whimper I ease my legs apart.

"Where else did the stable boy touch you?" Your voice has dropped to a whisper, but is no less commanding.

I shake my head in panicky denial. "Nowhere! I told you, all he did was kiss me-" My voice is shaky and pleading.

"I'll have to check, young lady, and you'll regret it if you've been lying to me," you warn. I feel a hand slide from my rear to my thighs, slowly separating them; then, through my panties I sense the light caress of your fingers, slowly stroking my labia. Almost against my will I arch my bottom, rubbing my sex against your exploring fingers.

"Look how wet you are," you chastise me. "Your panties are damp. Obviously this stable boy has done more than kiss you. How else do you explain your aroused state?" Your fingers continue to rub my vulva through my cotton panties. Suddenly you give my mons a gentle spank.

"I'll have to take these panties off and examine you further." At your words I gasp, aroused and shamed at the same time by my arousal. I feel your hands at the waistband of my underwear, and I arch my bottom so you can slide my panties down, over my rear, then off my legs. A shudder of anticipation runs through me.

Slowly your hand returns again to the leaves of my sex, gently spreading them. "So swollen, so needy," you murmur, your fingers sliding slowly towards my aching bud. I moan, low and pleadingly, wanting you to stroke me and pleasure me. Gently you squeeze my hooded clitoris, your touch light and teasing. "Surely he touched you here?" you question me, your voice urgent.

"No- no-" I gasp pleadingly.

"Little liar," you chuckle, your fingers continuing their seductive torment of my aching pussy.

Now I feel an inquisitive finger at the entrance of my sex, circling slowly, then easing inside me. I feel your fingers caressing the velvety walls of my pussy for a moment, then penetrating me deeply.

"Not a virgin," you comment, but I am silent. "Did the stable boy fuck you, then?" I am both shocked and aroused by your coarseness. Weakly

I shake my head in denial. You penetrate with a second finger, stretching me, your fingers slick with my arousal, your thumb gliding rhythmically against my swollen nub. I begin thrusting back against your hand and you spank my arched backside sharply. "Be still," you admonish me. "It's time for a lesson in self-control."

"You are aroused by my hand, yes?" Your question is rhetorical, my only reply a frantic, plaintive moan. "You need to climax. Your body yearns for release. I'll give you an orgasm, Michele, but after you climax, I'll also spank you, as a reminder of the need for self-control. A hard spanking. A long spanking. The longer you can hold off your orgasm, the longer you delay your punishment."

With these words I sob despairingly, knowing that my spanking is imminent. Your fingers continue their relentless penetration of my quim as your thumb circles the swollen bead of my clitoris, making me ache. I arch my rear pleadingly toward your hand, ashamed by the intensity of my need, thrusting frantically toward you. You work a third finger into my cunny, widening it even further, intensifying the sensation. I'm almost there . . . .so close . . . .

Now a finger from your other hand slides from the small of my back to the cleft of my bottom. I feel it slide down the divide, toward my anus and I cry out, ashamed by the immediate jolt of pleasure I feel.

You rub gently at the tight, wrinkled hole, pressing teasingly at my most secret entrance. Massaging my clitoris in a series of quick caresses you ease a finger past the tightness of my anus, rimming it teasingly. With a sharp, keening cry I climax, the muscles in my pussy contracting tightly on your penetrating fingers. As my breathing begins to slow, you murmur to me wordlessly, bringing me down, soothing me. Gently you pull your fingers from my quim and bum to stroke my inner thighs. For a moment both of us are silent. Your weight shifts slightly beneath me, and you open a drawer in the table placed beside your chair. I hear you remove some objects from the drawer, but am unable to see what they are, perched as I am, upside down on your lap.

"Time to prepare for your punishment, Michele," you announce, and with a sense of delicious, shamed apprehension, I wonder what form these preparations will take.

* * *

Draped as I am, upside down over your lap, I cannot see what objects you have removed from the table drawer, and my body, from toes to shoulders, grows rigid with anxiety. Sensing my tension, one of your strong hands rubs my back in long, sweeping strokes, then slides down to cup and squeeze the cheeks of my bottom, rubbing and massaging them with circular motions. Unwillingly I arch into your caress.

"That's right, Michele," you urge me as your hand continues its tantalizing motions. "Relax for me. There's nothing to worry about. I'm going to prepare you now for your spanking. Try not to tense up; you'll only make things more difficult for yourself."

The hand on my bottom pulls firmly at one of my cheeks, revealing the deep cleft and tiny pink anus to your dispassionate scrutiny. I let out a mortified gasp as I feel your index finger prod insistently at my most secret entrance.

"No need to be nervous," you admonish me with a hint of laughter in your voice. "I've played inside this shy hole recently. Open up for me."

Stubbornly my bottom hole remains tightly clenched. Your finger slides away for a moment, dropping down to stroke the sensitive area between my pussy and anus. Immediately aroused, I moan plaintively and arch my rear needily towards your knowing hand. As your finger continues its delicate caress, your thumb works lightly on my anus.

"Go loose, Michele," you encourage me. "Let me in."

And I feel my sphincter yield to the unrelenting thickness and pressure of your thumb, the tight muscle clenching and unclenching against this invasion, slowly accepting you.

For a moment you are content to steadily thrust your thumb in and out of my anus, my secret passage growing accustomed to this welcome intrusion. Your other hand holds me firmly across your lap, gripping my waist. Then slowly, reluctantly, you pull your thumb from the hot, tight confines of my rectum, patting my bottom approvingly at my obedience. I sigh deeply and settle more comfortably against the scratchy cloth of your trousers.

Almost immediately I sense a new pressure at my anus; it is not a finger, but something larger, smoother, more rounded. I jerk convulsively, feeling panicked, but my anus, prepared by the careful attention of your thumb, eagerly accepts this new, thick presence. As you slide the object deeper into my bottom, I groan protestingly, feeling uncomfortably full, but you ignore my complaints, working it insistently deeper into my bum. Finally the unrelenting pressure ceases, and I clench cautiously on my invader, feeling its flanged, flat circular base spreading my cheeks. Your fingers flick and tap at this handle, sending shock waves through the sensitized flesh of my rectum, and I moan helplessly. You give a pleased murmur.

"Lift your tummy." I immediately oblige and you slide a small cushion underneath my tummy, so that my hips and bottomcheeks arch invitingly upwards.

"Time for your punishment," you announce, and I let out a small whimper of anticipation and dread. Your hand on my waist tightens. "And the first part of your lesson requires that you ask for your spanking, Michele." Your voice is cool, controlled.

I shake my head furiously in mute refusal, staring rebelliously at the carpet of your private study. Under no circumstances will I ask you to chastise me. Never.

Again I feel your hand on my bottom, your fingers squeezing, testing the resiliency of the supple flesh. Then these fingers slide to the plug in my anus, and determinedly and deliberately you twist it, exciting my already aroused rosehole. Next I feel a light finger settle on my clitoris, swollen and needy in its fleshy shelter. You stroke my bud with a steady, teasing finger, and I feel my wetness begin to leak from my sex and trickle onto my thighs.

"Ask for your spanking, Michele. After punishment comes pleasure. But you have to ask. Be a brave girl and ask for your spanking. And after your chastisement I'll play with your pussy until you climax." Your voice is low, tender, commanding . . . . and convincing. You continue to play with my clitoris, but the pressure is too light to bring me to orgasm. Instead, it torments, promising future pleasures if I only submit to your dominance.

With a sweet, acquiescing sigh I plant my hands firmly on the carpet and in a shaky voice murmur, "please, spank me, sir."

I hear your sensuous, pleased chuckle, and then I feel your lips, soft and warm, plant a single kiss ono one poised, expectant cheek.

"Good girl."

The first spank immediately follows this brief caress. Your palm, wide and heavy, cracks sharply across my right cheek and I gasp and lurch against your lap, struggling to escape. Your left hand clamps more firmly on my waist and I hear your voice, seductive but stern: "be a good girl and take your punishment bravely. And remember, the hand that punishes also pleases." Your fingers slide fleetingly across my swollen, dripping labia.

Again your right hand swings forcefully down, this time to smack me high on my left cheek. The heat and sting of the swat blossom on my bouncing globe like a flower, and the warmth of the blow radiates and spreads through my rear. I wriggle in pain and pleasure.

"Be still," you admonish, and immediately I am motionless, my bottom arched expectantly toward your descending hand.

Now your hand rains down spanks on my defenseless bottom, the rhythm smooth and unhurried. You alternate the blows; first the right cheek, then the left, your hand progressively covering every inch of my arched backside. After twenty stinging swats to each cheek you stop to massage my reddening flesh, easing the pain somewhat. I gasp and hiss a little, unwillingly enjoying the caress, arching into your comforting hand.

When you resume paddling me the blows are harder, and I wail and kick my legs in protest; the stinging sensation is deepening and my bottom feels incredibly tender and sore. Your hand is relentless, however; the spanks are harsh and seem to be coming at a quicker pace. My poor flesh has no time to absorb one blow before another rains down. Again, after a series of spanks you cease chastising me. In the silence and still of the room I become aware of my breathing, heavy and ragged, and of my hair, hanging in my face, and of the weight of my breasts as they dangle.

For a moment or two you are content to stroke my reddened bottom, your fingers occasionally teasing my labia or prodding at the plug in my anus. I let out a relieved sigh. Perhaps you have finished spanking me. Your voice breaks the stillness of your study: "Open your legs for me, Michele." Reluctantly I spread my thighs, hoping that now you will begin pleasuring me as you have promised.

However, my punishment is not yet over. With my legs sprawled for you, the skin on my rear is tighter, my anus and sex fully exposed, and I hear you give a pleased sigh- at my obedience or at the vision my upturned backside presents- I cannot tell. Relaxed and anticipating your caress, I am dismayed to feel the sudden harshness of a spank immediately over the plug lodged deep in my rectum. I give a startled yelp; the blow is hard and it drives my body forward over your lap even as it lodges the plug deeper into my rectum. I scrabble for balance. Immediately you pull me back a bit so that I am again securely perched on your knees. You grasp my waist more firmly and the paddling resumes.

The blows are forceful and swift, and you deliberately target them to fall rapidly and painfully on my spread, stretched anus. Each spank lands on the plug lodged in my anus, further tormenting my aroused secret flesh. I begin to cry out, the sobs wrenched from my throat. The pain from the spanking, the soreness of my bottom, the heat radiating from my reddened cheeks, and the arousal created by the sensations in my anus- all combine. I can no longer distinguish between them.

The spanking continues and I find myself arching my bottom higher, seeking the chastisement of your hand. As each swat lands, I find my arousal spiralling higher and higher. My moans are no longer only of pain, but of intense sexual longing. As my anus clenches and unclenches against its welcome violator, the feelings of arousal are transmitted to my sex, and I rock my pubis against the firm pressure of your knee, needing desperately to orgasm.

With a sudden sharp cry I climax, rubbing my clitoris against your knee, my hips jerking convulsively. I hear your voice, as if from a distance, urging me on, and I feel your hand gently stroking my sore, burning bum, your fingers occasionally tapping wickedly at the plug that spreads my anus.

Sighing blissfully I relax across your lap, feeling sated, sweaty, sore and content. But you have not yet finished with me. With firm hands you lift me off your knees, so that I am standing in front of you.

"Show me your bottom," you command, and obediently I comply, turning so that my back is facing you. I know that you are relishing the reddened state of my backside. Then you rise and I feel your body, still clothed, against my back, your hands firmly clasping my hips. I hear your voice in my ear: "I want you to turn around, face the chair, and brace your hands on the seat."

Again I obey, placing my hands on the cushion of the chair you occupied moments before. Your hands settle on my hips, arching my bum towards you. With firm fingers you grasp the base of the plug lodged in my rectum and tug it from me. I hear the plug fall to the floor, then the rustle of clothing.

Suddenly your cock is nudging at my anus, seeking entrance. The plug has stretched me, and my body accepts you easily. Your erection slides steadily past my sphincter until you have fully penetrated my bottom.

For a moment you are still, savouring the heat and tightness of my ass. The fabric of your trousers scratches against my sore, tender cheeks, and your grip tightens on my hips. Slowly you begin to thrust.

As you shaft me your hands slide up from my hips to cup my breasts, squeezing the rounded flesh, toying with my nipples. With each determined thrust I gasp, enjoying the thickness of your erection as it slides deliciously in and out of my rectum. Your pelvis drives against my rear and I arch towards you, welcoming the pressure against my sore spanked cheeks. Your breathing quickens and grows harsher as you thrust more forcefully.

Suddenly your hands abandon my breasts to fall once more to my hips, and you torment me with a series of stinging spanks to my flanks, even as your left hand slides into my crotch, seeking my pleasure bud.

"Wanton hussy," you reprove me, your fingers sliding knowingly across my aching clitoris.

With a deep groan you bury your shaft in my tight back passage to the hilt, and I feel your semen spurting deep inside me. Giving my rear a final, stinging spank, with your other hand you rub insistently at my clitoris and I quickly climax, my bottom hole spasming around your erection.

Sighing regretfully you ease your cock from my swollen, widened anus, giving my rump a final, admonitory spank. I remain bent over the chair, waiting for you to tell me what to do. Finally you grant me permission to rise and dress. As I scurry to find my clothes you advise me: "It is obvious to me, Michele, that you require continuing lessons in discipline and self-control. I'll have Matron set up a regular series of disciplinary sessions."

Quickly pulling on my panties and bra, I shudder deliciously, both aroused and shamed by the meaning of your words, anticipating future punishment and pleasure at your capable hands.

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A fantasy by:

  sexhopper69 (view profile)

Uploaded fantasies: 8 (View all)
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Fantasy Info:

Categories: Steady Partner, Anal Sex
Location: Other | Roleplay: Student/Teacher
Fulfillment: Act on it | Nature: Agressive