Boarding School Discipline Diary

BOARDING SCHOOL DISCIPLINE DIARY

Part One

Chapter One… A girls’ first visit to the Headmaster

‘Swish… Thwack!’

“Oomph!”

The crisp pain rips through her bare breast startling her, the thickness of the tightly wrapped cloth-eye mask keeping her in virtual darkness as a welt instantly rises across the flattened mound.  Her dreaded punishment’s begun.

‘Thwack!’

“Aaaggghhh!”

More piercing pain, her other breast flattening, enveloping the flexing bamboo shunt as she twists, jerks at her bindings, grunts through the soiled mouth-gag.

“You understand yet?”  He asks, lowering the shunt, flicking it upwards between her spread legs.

‘Thwack!’

”Gaaaaaaaddd!... Omph!... Oomph!”

Knees trembling, reflexively pressing inward as she frantically jerks her head up and down, the feel of the damp, flexing cane flicking away from the sensitive flesh between her thighs, the fresh pain resonates through her groin.  Reflexively tiptoeing, just as quickly slumping, wrists already chaffing from the leather bindings borrowing into her flesh, her fists clench as her head droops forward between her outstretched arms.  Hair entangled, spreading from the loose braid unraveling freely across her shoulders while also partially covering her face, she mumbles through the cloth gag, gingerly nods her head again up and down as she practically semi-squats, her quivering legs spreading apart at the knees between the wooden shaft, bound between her ankles.

Stepping slowly around her, the dampness shimmering across her youthful bare flesh beneath the glaring lights, the binding ropes creak, the pulley twisting from the weight of the horizontal rod supporting her from above.  Inspecting the welts, thin, crimson, raising a half inch or so above her otherwise unmarred flesh, watching her stomach hollowing, the silhouettes of her abs contracting, expanding with each forced breath, he flicks the tips of the pair of supple shunts of bamboo together a couple times as he positions himself directly in front of her.

“No… No I don’t think you fully understand just yet.”  He scolds, measuring a shunt deep beneath a breast, lifting upwards with a curling of his wrist.  Raising the symmetrical mound a couple, three inches, letting the firm flesh spread across the supple cane, the thickening nipple flip out and over as it jiggles, he flicks his other wrist as he adds.  “I think I’ll give you a little more to think about with a crisp flick right across this nipple after I center it… There… Right there… Now hold still.”

‘Thwack!’

“Aaaaaaaggggghhhhh!”

An anguished squeal, her jerking body twisting away in the flexing ropes, he lowers the shunts, watches the fresh crimson streak rise across the bruised areola.  Again ‘clicking’ the pair of shunts ominously together, stepping around her as he allows for her heaving breasts to stabilize, slipping the tip of the lower shunt beneath her other breast, watching her squirm, listening to her unintelligible mutterings through the saliva drenched gag, he flicks his wrist, again, just a little harsher.

“Hold that tittie still… I want a good path to the nipple… Might want to hold your breath though, this one’s going to be a little harsher… Now hold it still or I’ll do it twice!”

‘Thwack!’

“Ooooooooommmmmmpppppphhhhh!”

The bamboo momentarily enveloped by her titflesh, his wrist jerking back, the shunt flicking back from her stretching breast as her naked body contorts, she jerks at the flexing ropes hoisting her arms high above her head.

“Gaaaaaaaaaaaaddddddd!... Ooomph!”

Another guttural shriek followed with a whizzing breath, she bows forward, her firm breasts bobbing, swaying, both areolas, nipples crisscrossed with matching crimson welts.  Again sagging in her restraints, slowly twisting from one side to the other, her naked body glistens with a splotchy, uneven coat of perspiration.

Laying the bamboo down, untying the mask, tugging the damp cloth from her mouth, gripping her hair from behind, he cranes her neck back.  Brushing some loose strands of hair away, glancing into her welling dark brown eyes, across her flushed face, he gently cups a breast, lets it jiggle, bounce between his melding fingers as he drops the rumpled cloth from his other hand.  Her parted lips quivering, swollen eyes starring into his, she knows better then to speak, to beg even as he forces her to tiptoe as he hoists her upwards by her hair.

Bowed forward in his grip, her breasts spreading, swaying, she arches spread-eagled in her restraints.  Lowering her eyes, glancing down toward the pulsing pain resonating from her chest, the red welts crisscrossing both globular mounds, she stifles a whimper as she feels his clenching fist twisting at her hair.

“Understand now?”

“Ye… Yes Headmaster…. Yes Sir!”  Her voice almost a childish whimper as she answers.

Kneeling down, untying her ankles, standing, untying her wrists, he steps back a step, crosses his arms, speaks.  “I’m waiting.”

Sobbing, kneeling on one knee then the other, reaching up, unwrapping her tangled hair between her twitching fingers, she continues to stare down toward his feet as she struggles to hold back her tears.  Nervous fingers pressing through the clumping strands that were just recently a tight braid, shaking her head as she fidgets, pressing her hair behind her shoulders, she finishes, cranes her head back as she interlocks her hands behind her neck.  Thrusting her breasts outward, clenching her fists, spreading her thighs as her ankles slip across the floor in a practiced position, she takes a deep breath, holds steady, silent.

Holding her robe in his hand, the only clothing she was allowed to wear for his meeting, glancing over her fresh welts, none so severe a good lotion massage wouldn’t help heal, handing the robe toward her, he asks.  “Next time I call you to my parlor during the evening, you’ll leave your hair down… Understand?”

Chapter Two… Demerit Days Begin

       Holiday, watching most of the other girls leaving during the early morning hours, getting in limos, cars, cabs with their luggage, she watches out the third story window of the private little room, one of the rooms on the far wing of the rambling boarding school for the wards of the institution left behind for the Holidays.  Knowing she’s staying, the next few days the complex being virtually shut down to normal routine, she can only wish she was one of the others with somewhere, someone to go too.

       Glancing toward the clock as it appears the final car’s leaving, the campus left nearly vacant of students, she realizes it’s just a matter of moments before she’s summoned.  The whispers, the hushed stories of what happens to those few left behind runs through her mind as she cups her bare breasts after dropping her damp towel onto the mattress, stares toward the black leather hood, the leather cuffs laying across the dresser with the detailed note attached.  Having already felt the pain and humiliation of being disciplined with the cane by the Headmaster across her nude flesh previously, she’s about to find out just how true some of the more ominous tales are, the note laying out her instructions on the mask a stark reality.

       Sitting on the chair, the reflection of her naked body in front of her, bending forward she fastens a cuff to one ankle, the other as directed.  Heartbeat escalating, nervous, feeling the confining leather across her ankles, again glancing at the mirror, fitting a cuff across her left wrist, the right, she checks, makes sure they’re snug.  Taking a deep breath, the hood next, just a couple weeks since she’s last briefly warn it for punishment by the Headmaster; she holds it in her hands, fidgets with the straps as she takes a couple more deep breaths to calm herself.  Recalling the fit, the feel of the leather across her face, confining her, the straps that can close across her eyes, her mouth, she cuffs the supple leather between her fingers, positioning, aligning the mask while again glancing toward her reflection from the mirror.

Fitting, tugging the supple leather across her head, her face, peering out through the narrow slits as she fastens the straps around her throat, snaps the small, gold locks into place on either side, she feels the seams of the mouth slit compressing across her lips, the bridge of the leather contouring, flattening across her nostrils.  Finished, staring toward the mirror, the reflection of her otherwise naked body, she allows her arms to hang down by her sides, watches the four small locks gently sway from the mask, the third beside the eye strap, the forth beside the mouth strap as she waits, a steady thumping in her chest, anxious, embarrassed.

The tap on the door, it opening, she takes a deep breath, holds it in as he steps towards her.  It’s him, the instructor most of the girls seem to have private crushes on.  The fittest, the best looking of the faculty, his only setback, not really overly harsh but stern in handing out demerits, and following up with administering the discipline himself, she knows whatever she’s about to do will be wrong as she struggles with not covering herself, her naked breasts from  his view.  Sensing him closing toward her, glimpsing his form reflecting from the corner of the mirror; she remains virtually motionless, humiliated, eyes straight ahead as she sets there naked, in bondage, the mask concealing her flushing face as he’s obviously slowly taking in the rest of her nude form.

“Demerit days.”  His voice straightforward, assertive, she reflexively jerks, feeling his hand across the nape of her neck as he continues.  “First things first… The instructor’s lounge floor needs a good scrubbing to start with… Shall we?... Stand up straight, shoulders back… Hands behind you as you follow… I want to see those titties pushed out and bouncing.”

The warmth of her flushing face obvious to her even beneath the mask, feeling his fingers squeezing her shoulder, his other hand sliding across her midriff, she senses herself almost shivering to his touch, to his hand roaming across her bare flesh.  Standing and turning toward the door, his fingers momentarily cupping her breast as she’s slowly twisted around, she gives off a slight moan, her puffy nipple tingling beneath his fingertips.  Bare breasts barely jiggling, actually too firm to bounce, she takes a single step forward, the sense of utter humiliation as she feels his hands pressing across one shoulder, forcing her other shoulder back.  Obediently sliding her hands behind her bowing back, the leather cuffs scrape together as her firm mounds jaunt outward, spread apart.  Holding back another grunt as she feels a breast twisted, the nipple teasingly pinched before let go by his firm fingers, she tries to remain silent, obedient.

“Need a floor scrubbed… From wall to wall… Come with me.”

Following, turning down the hall, a couple minute jaunt naked through the now vacant corridor usually filled with students, she follows him into the empty study, watches as he slips off his tweed jacket, rolls his white shirt sleeves up to just below his elbows.  Glancing around the near barren room, the blinds up, the sunlight filtering through, she can’t help noticing the wooden bucket sitting near the center of the oak surface, soap overflowing into a puddle across the floor.

“Okay… Now on all fours… Face the bucket, look up here at me and keep those hands clenched behind your back while I demonstrate want I want done.”

Obediently kneeling, knees slipping across the damp floor as they spread beneath her, facing toward the bucket as she clenches her wrists behind her back, she peers through the mask’s slits as he reaches over, shoves his hand into the bucket, retrieves a sopping bristle brush.  Watching him step around, position himself behind her, his left hand cupping her left breast, squeezing, melding before lifting it out and upwards, holding her breath, the sense of his hands on her naked body’s humiliating.  Glancing downward as the cool soapy water splashes across her bare breasts, her thickening nipples, her eyes widen as she sees the brush dripping in his other hand.

“Keep those titties pushed out here just like that.”

His voice demanding yet somehow not harsh, his fist squeezing tighter, she again  obeys,  but hesitantly as he tugs her breast out even further in his tightening grip,  Squinting her eyes as she stares toward the bristle brush being lowered directly toward her chest, realizing what he’s about to do, taking a deep breath, she groans, closes her eyes.

“Like this… Scrub the floor just like this.”  He orders as he flicks the brush slowly back and forth, back and forth, scrubbing across the nipple flipping out across his thumb, flattening and stretching the nub as her breast instantly reddens, tugs back and forth, side to side beneath the flexing bristles.  “Soak it… Drench it… Scrub it good and hard… And look up here at me, like I said.”  He continues as he splashes the brush back into the overflowing bucket, squeezes the base of her breast even firmer, again scrubs back and forth above, below, across the swelling nub as the soap suds streak down across her stomach.

“Ooomph…. Humph… Ooomph… Oooooommmppphh!”  Grunting with each passing of the brush across her bare skin, feeling his hand releasing her breast, blinking, seeing the brush again being dipped into the bucket, his hands switching, her right breast gripped, nipple bulging, the brush scrapped back and forth at a brisker pace, up and down, crisscrossed against her contorting breasts, she again squints, grunts, stares up toward him, accepts the chafing pain of the harsh bristles against her tender flesh scrapping back and forth.

“Every nook and cranny, squeaky clean… Understand?... And keep that back bowed!... I’m not done yet.”  He orders as he looks in her welling eyes peering up from the mask’s slits.  Another dip into the bucket, her breasts released, the brush raised out in front of her, scrapping across both thrust out breasts, his free hand tugging back at her mask, the brush chaffing her soaked flesh back and forth, back and forth, squeaking, squeaking with each thrust, he finally steps back a step, reaches out the brush, orders.  “Here now… Get to work!”

The brush dropped with a splash into the overflowing suds, him stepping back another step, she numbly obeys, aching but relieved he’s finally done tormenting her sore breasts for the time being.  Reaching in, retrieving the brush, leaning forward, both hands on the brush, her bare butt thrust upward, she begins scrubbing the hardwood floor as her sopping breasts, reddened and chaffed, sway back and forth, drip soapy water to the floor beneath her.

“Stay busy… I’ll be back in about an hour or so to get you for the Headmaster’s scheduled session… It better be at least half done or I’ll scrub something else of yours that’ll be even more painful with that brush.”  He orders as he wipes his hands, rolls his sleeves back down one at a time.  “You don’t want that… So you better not waste anytime… Understand?”

“Oomph!”  Mumbling, a jerky nod of her head in the skin tight mask, her chest pulsates, burns as she scrubs the brush back and forth, rapidly back and forth across the oak planking, fearing the consequences of disobeying his order while trying to block the thoughts of facing the Headmaster next.

Chapter Three… A Demerit Discipline Session

       Led out the doorway, passing another unfortunate ‘student’ being led in virtually naked with just a similar hood and cuffs, her instructor leading her with a leader chain attached to the bottom of the hood.  Her wrists actually fastened behind her back, her more pendulous breasts jaunting outward, swaying, bumping together, it’s obvious that girl’s eyes are transfixed toward the crimson marks left from the bristle brush as she hesitantly steps past.

       “She’s going to finish the floor… Of course after being instructed on the proper procedure… Think she’s wondering about those scrubbed titties of yours?”

       His voice matter-of-fact, as he slowly turns, watches the girl being led to the other side of the room toward the bucket, he cups the discolored breasts in front of him, gives a slight squeeze.  “I wasn’t really all that harsh with these… Was I?”

       “Oomph!”

A low grunt, the chaffed titflesh aching, yet tingling to his touch, she stands obedient, allows his fingers to manipulate her damp, sore breasts as he’s obviously enthralled by the sight of the other girl kneeling, positioning herself in front of the bucket, the same brush being swiped back and forth across her bare breasts obediently thrust outward.

       “Okay…  Yes… Yes… She’s getting the feel of it now.”  He finally smirks, turns toward the hall as the squeaking sounds of wet brush across bare flesh mixing with tormented squeals echo from the barren room out into the hallway.  “Let’s go… Follow me.”

       To the stairway, breasts jiggling, swaying, still aching as she passes a landing, continues down another flight, she enters another hallway, passes a few shut doors to some familiar class rooms, finally to arrive at what she thought was an instructor’s private office.  Stepping inside, seeing the back of the Headmaster by a window, the sight of a whipping post, a St. Andrews Cross and even a stock lining the walls, she can’t help noticing a vat of crops, canes off to the side.  Heart pounding in her chest as she watches him turn toward her, a wide, barber style leather straps’ dangling in his clenched fists.

       “The hood… Remove it please.”

       Feeling the hands behind her neck, the hood manipulated, twisted and lifted above her flushed face, she senses the hands tugging at her raveled hair, twisting it behind her neck.

“Thank you… Now stand her in front of the post… Backside to it… Her hands up to the brackets.”  He adds as he casually steps within a couple steps of her.

       Shuffled backwards, pressed against the mahogany post, her arms hoisted upwards, wrist cuffs secured to the eyelets, she remains silent, nibbles across her lower lip as her aching breasts jaunt outward, spread toward her armpits as she’s forced to tiptoe.

       “Now, the eye mask and… And I think a throat chain… Then we begin.”  He orders as he flips the curling strap back and forth in swishing arcs.  “Time to work off some of those demerits.”

       Eyes widening, tears welling, she feels the narrower mask slipping across her forehead, down over her eyes, the black cloth loose ends twisted, tied behind her neck, the clanking of a chain stretching around her throat, affixed to the post.  Sensing her naked body being forced to arch outward, her already reddened breasts the obvious recipients of her forthcoming punishment, pressing back against the varnished post, she takes a deep breath, exhales.

       “Now… I believe you’ve earned… Let me see here… Eight… Nine… And let me think now… Yes… Yes… That’s right… That’s ten demerits that I can remember right off.”  His voice condescending, glancing toward the instructor he continues.  “So… I think we’ll just make it an even dozen to be safe, don’t you agree?”

       Hearing his voice close enough to her ear to feel his warm breath, the presence of the leather whisking back and forth just in front of her spread nipples, she quietly moans, braces.

       “Okay… Take another deep breath if you want too before we start… You should be familiar with the routine by now… Or will soon learn it.”

       ‘Swish!... Thwack!’  The almost immediate flick of the strap, the sound of flexing leather smacking across titflesh echoes in the otherwise quiet room.

       “Oomph… Oh!… One… One Headmaster!”  She grunts, the feel of the supple leather flattening her naturally puckered nipple into her chaffed breast burning.  More then a moan then her normal voice, she finishes her rehearsed repertoire.  “Thank… Thank you!”

An appreciative nod, he slowly steps to her other side, watches her stomach flexing, her breasts jiggling, glances knowingly toward the instructor.

“Very good… Yes… Proper response right away… That’s good… Our little ward’s coming along rather quickly, isn’t she?”

Letting the handle of the strap glide beneath her right breast, press into the titflesh, lift upwards, sliding the handle higher, toying with the seductively thick nipple, the natural little mound of both nipple and areola, he teasingly probes, twists the tanned areola slowly back and forth, shoves inwards, forces the youthful, yet erotically succulent mound to swell around the probing leather tip.

“This tittie next… Now on the count of three.”  He speaks.  “And again… Right across that puffy little very nub of the nipple.”  He intentionally aggravates her verbally while nodding toward the instructor.  “Here, grip her breast… Hold her nipple out here for me… Watch your fingers though.”

Feeling her breast being cupped, hoisted in spread fingers, feeling the firm mound being squeezed, the nipple swelling and standing out, she grunts, holds her breath, presses the back of her head against the flat surface of the post as she hears the countdown.

“Two…. Three!”

‘Thwack!’

“Oomph!”

A harsher stroke, the searing, piercing pain of the flattening leather smacking across her engorged nipple, her naked body shudders as she grunts, jerks across the slickened post as her breast’s released to barely bounce.

“Ohh… Ohhh!”  She groans, mumbles.  “That’s… That’s two Head… Headmaster… Two… Tha… Tha… Thank you Headmaster!”

Both breasts throbbing, fingers clenching into fists above her head as she feels the chain rattling across her throat, she inhales, exhales, tenses against the post.  Blinking into the blackness of the eye mask, a tear trickling from beneath it, she steadies herself, awaits the next lashing.

Surveying the red splotches superimposed across her already discolored titflesh, reaching out and cupping one, the other, squeezing, examining the feel of the pliable, yet firm mounds, the Headmaster smiles toward the instructor, gives an approving nod while ignoring her whimpers.  “Youthful tits are so resilient.”  He smiles.  “And these are so perky… Just seem to bounce back so nice and firm… Don’t they?”

Positioning himself to her side, continuing to squeeze a breast, he flicks his wrist.  ‘Thwack!’

“Oomph!”  Startled, feeling the curling strap unexpectedly flatten her other breast so quickly, she hesitates responding, realizes the consequences, blurts out.  “Thr… Three… That’s… That’s three Hea… Headmaster… Three… And… Oh… Thank… Thank you!”

Again a pause, releasing her breast, slowly stepping around her he whispers almost gently near her ear.  “Just In time… Painful… Is it?”

“Yes… Oh yes Headmaster.”  Her voice just above a whimper, her breasts throbbing with each heartbeat, she slowly nods.

“Well… What have we left?... Let’s see… Nine… Nine more to come… Haven’t we?”  He whispers, glancing toward the instructor with a smug smile.  “Just nine more across these firm, youthful breasts of yours… Right?... How many more do you have coming?... Did we say nine?”

”Ohhh… Ohh yes Sir.”  She stutters.  “Yes Headmaster… Nine… Nine more!”

“Let me ask you something.”  He smiles as he lets the strap slide ominously back and forth across her aching breasts.  “Would you like to feel less pain?... Actually maybe even just the opposite?”  Probing the strap a little harsher across a nipple, he continues.  “Go ahead… You may answer me.”

“Wha… What Headmaster… No… No more pain?”  Her voice a pleading whimper, she begs.  “Oh… Please… My… My breasts hurt so bad… Please, yes!”

“I said less pain… Then maybe something different.”  He answers, letting his free hand glide lightly across her quivering stomach, her waist.  “I’m willing to give you a chance… But you must obey… Completely obey and submit or face the consequences of a much harsher punishment… Now… Are you willing?”

Listening to his voice, strangely different then his normal demanding tone, feeling his fingers gliding across her rippling navel, down across the rounded curve of her pubic mound, sensing a couple fingertips flittering across a fold of her labia, she inhales, tiptoes, reflexively braces as she feels the fleshy lips between her thighs spreading apart.  “Ooooh!”

“The next few lashes are down here if you refuse… Right between this slit… And with the bamboo cane.”  He rasps as his fingers gently tug, part her labia.  “Hard… Crisp strokes… Or else you……. You can ask me to continue with what I’m doing now.”

“Huh?... Waaa… Huuuuuhhh?”  Rasping, sensing her hips twitching, his fingers lightly probing between her thighs, she purses her lips, clenches her fists high above her head to the humiliating sensation.  “No… No please…. Ohhhhh… Not the… Cane… Cane down there!... Ooooohhh!... Uumph!... Do… Do that… Ohhh… Do that!”

“Then tell me how this feels…  Concentrate and tell me.”

Bracing against the post, arching, hips rotating, responding to his fingers, she feels the tingling, the strange sensations she’s only felt the few times she’s touched herself, touched herself in private, under the covers, maybe in the shower’s pulsating water.  But, this time so much more defined, magnified as his fingers press inwards, searches, flicks across her engorging nub.  Humiliating, yet certainly not painful, the thought of the cane being used down there and she focuses on his manipulating fingers probing into her tight slit.  “Ooooohhhhh!... Uuuuummmmm!”

“You’re still a… Virgin… Aren’t… You?”  His voice almost pleasant, slower, in rhythm with his fingers gliding back and forth, probing, massaging.  “You’ve come to us a virgin… Never… Never… Had… A man’s fingers inside you… Before… Have you?”

“Aaaaahhhh.”  A sigh, arching backward with her hips, feeling her buttocks grinding back and forth across the post, her lower lip curling, her teeth gently gnawing, she moans, whimpers.  “Oh nooo… Yeesss!… I… I mean I’ve… I’m a… Vir… Virgin… Yes… Ohhhhhh!.... Ahhhhhhh!”

“You’ve a choice to make then if you don’t want the cane.”  He whispers in her ear as he presses close to her naked body.  “Being a ward of the institution… You’ll… Spend the rest of this Holiday as the others under strict supervision… Workng off their demerits… Or……….”

Feeling his finger probing her hymen, pressing against her clit, her thighs a continuous series of twitches, she leans back against the post, feels his body pressing against her breasts, flattening her firm mounds across her chest.  Thinking of the scrubbings, the punishments, the abuse, she wonders what to answer, to submit too even as the pain across her breasts are becoming somehow, someway less noticable, the soothing sensations between her thighs, even her flattening nipples responding, becoming warm and tingling to his touches.

“Ohhhhh!... Ahhhh!... Ohhhh!... Not… Not the cane… Not down there… Please!”  Each breath a sigh, each touch forcing a reflexive response of her naked body against the post, she finds herself moaning, pleading, rambling.  “What… Whatever else you… You want to do to… With me down there… With… With me… Oooohhhh!... Yesssss… Yesssss Headmaster!”

A smile, a nod, stepping back he glances toward the instructor as he raises a dampened finger.  “I think she’s ready for some personal tutelage now… Maybe even ready to feel what its like to be mounted… Step out here with me for a moment, okay?”

An appreciative nod back, the instructor follows as they leave the room, her quivering body suspended against the whipping post.

“I’ve got another appointment… Another ward to administer too.”  The Headmaster instructs as he turns down the hallway.  “Carry on with her, I’m sure by the end of the holiday she’ll be quite prepared with the free reins I’m giving you.”

“Glad too!”

Chapter Four… Personal Training

       Stretched against the post, the pain’s become no more then just a discomfort, even having to be naked not as humiliating, the mask actually a kind of relief, giving some sense of anonymity.  Feeling a man’s touch for the first time, a man’s touch massaging her privates, the strange sensations; so far, considering the alternative; it seems far less of the two evils.  Again she’s thankful for the mask blinding her to their stares, to what’s being done to her.  Barely able to hear any of their conversation in the hallway, wondering, pretty well anticipating what he meant by being mounted, she finds herself taking deep breaths as her heart beats in her chest while she tries to anticipate what it’s going to feel like to be taken by a man.

       “Well… Seems you’ll be under my tutelage for the rest of this instruction… Understand?... You’ll be answering to me now, for the time being anyway.”

       Hearing his voice, the voice of the instructor, her thoughts are immediately of being his ward, of surrendering to him, actually somehow a sense of relief it’s not the Headmaster.  Slowly nodding her head, her voice almost a whimper, she replies.  “Yes… Yes Sir… I… I undertand, Sir.”

       “Well then… Let’s get started.”

       Even while listening to his voice, she feels the cloth being unbound, slipped from her eyes.  Blinking through her raveled hair, seeing him stepping back a couple steps, picking up a small jar, she blinks again, focuses on his nude body from the backside.  Shocked, staring toward his muscular form, tanned, incredibly conditioned, practically forgetting she’s naked herself, she’s confused, embarrassed yet also somehow excited in a strange, unfamiliar way as he turns back toward her, sits the jar on the floor as he rubs his hands together.

       “Here… Let’s take care of these to start with.”

       Again just listening, unsure if she should stare, turn her head, close her eyes as his manhood sways semi-erect between his rippling thighs, huge, even though half limp, she feels a cold sensation across a breast, his hand cupping, melding a glob of cream across the slightly discolored flesh.  A startling sensation, a deep breath, feeling his hand gliding across to her other breast, the equally cold sensation jolting through that puckering nipple, she can’t help moaning, taking another deep breath as she glances down, watches his fingers twisting, squeezing, the whitish cream oozing between his stroking fingertips.

       “Let’s work this salve in… Take away the sting… Soften these firm mounds some.” 

       Surreal, the naked instructor standing in front of her, manipulating her bare breasts, the instructor all the other girls have their crushes, their fantasies about, she nibbles on her lower lip, accepts the spreading warmth of both his hands now massaging her bare chest.  Thinking of the other girls, their girlish talks sometimes at night, giggling about what they’d be willing to do with him if they had the chance, she can’t believe she’s virtually body to body with him now, both naked.

“Oomph”  Unable to suppress a moan, sensing her chest arching reflexively outward, her breasts flattening into his enclosing fingers, her nipples tingling, her stomach churning, she feels the pressure across a thigh, the sensation between her legs, his thickening manhood slapping back and forth as he leans closer, presses against her.

       “You’ve nine more lashes… Some across these… Nine more total… Maybe some down there if necessary.”  His voice firm, matter-of fact as he continues to meld the responding mounds, the initially cold salve warming, heating across her bare flesh.  “You’re still getting them… All nine… But you’re going to learn a lesson involving pleasure and pain… Start to learn how to respond… To accept it… To enjoy both at the same time.”  Stepping back a step, rubbing his hands together, he asks.  “Now… Ready to start your first lesson in pleasing a man?”

       Barely hearing his words, about the lashes, the pain, pleasure, her breasts aching, not from pain but something else, something  beyond her control, she slowly nods, closes her eyes, flexes her hips, searching for that warm presence that was pressing across her thighs, brushing teasingly against her pubic mound.

       “Stand still… Keep your eyes closed if you wish… Just accept what’s in store.”  He instructs as he steps forward, reaches for her breasts.  “But do as you’re told… Understand?

       His hands so tender cupping, massaging, his fingertips so electrical to her nipples, her shriveling areolas, she can barely nod, closes her eyes as she whimpers.  “Ye… Yes Sir… Oh yes… Yessss… Sir!”

       “Spread those legs… Keep them spread wide.”

       “Yessssssssssss.”

       “Bracing yourself?... You’re about to become a woman.”

       “Uh…Huh!”

       Hearing his orders, mumbling, stiffening, more deep breaths, she feels a set of fingertips gliding downward, tickling her ribcage, flittering across her hollowing navel, pressing across her pubic mound.  Uncontrollably quivering, sensing the fingertips parting her labia lips even as her nipple’s still being tweaked, feeling the tingling flesh between her quivering thighs stretching, tugged, she again moans, bites her lip, twists her head to the side, moans.  “Ooooooooohhhh!”

       Anticipating, actually experiencing the feel of the girth of his manhood being pressed between her spreading thighs, the warmth, the thick, hard shaft probing past his spreading fingers, pressing, sliding back and forth across her moist slit, against the aching nub of her responding clitoris, she stares into the darkness of her tightly squinting eyes, holds her breath.  Tightening her fists, anticipating, not knowing what to really expect, what it’s going to feel like being mounted, a man’s shaft burrowing inside her, his shaft splitting her hymen, impaling her, she presses her buttocks against the post, stiffens.

       Hand sliding down from her breasts, the other up above her vaginal area, his fingers cupping her waist, she feels herself drawn forward toward his thrusting thighs.

       “Aaaaaaaaaaggggghhhhhhh!”

       A shrillish grunt as her breath escapes her, her thighs quivering, knees reflexively drawing tighter, she feels the sharp penetration of his throbbing shaft, over half its nine inches ramming into her stretching, tearing slit as his fingers grip firmly into her waist, holds her steady.  Tears tracing across her cheeks, hips quivering, fists clenching high above her head with clawing fingernails, her heart pounds as she reflexively responds to her first penetration, feels his girth engulfing her, stretching her vaginal walls, pulsing inside her as her breasts flatten against his chest, her body trembling between him and the post.

       “Oooooooommmmmpppphhhhh!

       Another guttural groan as she feels his shaft draw momentarialy back, instantly thrust inward another couple inches, again the jolt floods her womb as she feels the final tearing, senses being engulfed by the hot, throbbing meat.  Held firm again, his hands cupping her sides, guiding her, she feels her body beginning to tilt back and forth, slightly, in rhythm with his cock pressing inward, drawing outward, now just fractions of an inch more with each calculated thrust and withdrawal.

       “Ooooooohhhhh!... Aaaaahhhh!... Uuuuummmppphhh…. Aaaaaaahhhhhh!”

       Rasping with each slow, deliberate entry, each measured thrust penetrating further and deeper, the never before experienced sensation’s almost overwhelming as she uncontrollably trembles, quivers.  More almost gentle thrusts patiently repeated time and again, slowly in and out, still just a little deeper, the sensations from his burrowing cock stretching her vaginal walls boarders on unimaginable.  Moaning with each motion, gripping the post with clenching fists as she’s being impaled on his shaft, their naked flesh grinds against one another’s, her swollen nipples responding, pressing, twisting across his muscular chest.  His gripping fists still in position, holding, guiding her by her waist, the pain, the aching melding to something so different, something unbelievable, her contorting body instinctively responding, her hips jerk, her muscles tense, flex as she thrusts back, forces her flattening breasts to twist against his chest, her thighs to grind against his.

       “Oooooooohhh… Gaddddd!... Oh…. Yeh… Yeeeeeessssss!”

       Blinking, mumbling with each rasping breath, riding his pulsing cock, every inch of her body tingles as their naked bodies glisten, bead with perspiration.  Now following his lead as he pumps harder, deeper, flexing her hips as his shaft thrusts inward, withdraws, thrusts, withdraws, long, harsher strokes, stretching, engulfing her taut vaginal walls, she moans, groans in sequence.   “Uuummm!... Ohhhhh… Ahhhhhh!”  The pain forgotten, the pleasure flooding her body, her mind, eyes hazing, blurring, she wants more, even while his hands slides upwards, reaches up across her breasts, to squeeze them, meld them, manipulate her nipples as she tiptoes, slumps, tiptoes again.

“Ohhh… Yeessssss… Ohhhh!... God… Yessss… Yessss!”  Hearing herself responding, her voice almost unfamiliar, her breasts responding, aching, tingling, she begs.  My… My breasts….. Ohhhhh… Yesss… Squeeze my breasts too!...  The nipples… Pleeeeeeease!... Ohhh… Please!... Hard!... Harder!”

Obliging, cupping, hoisting her higher and higher against the post by the stretching mounds, letting her harshly drop in return a few more times onto his impaling shaft, her head slumping forward, her face pressing against his shoulder, her body trembling uncontrollably, he tightly grips,  squeezes, tugs and twists her thickening nipples, stretches the firm, perky mounds upwards to just beneath her chin, holds her steady, partially withdraws his cock.

Her ear just inches away, he inhales her scent, presses his chin across her dampening shoulder, whispers.  “Want me to continue… Have you experience an orgasm before we finish with your demerits?”

“Oooooh… Huh?…. Yeh… Ohhh, yessssssss!... Gad, yes!”

Rasping with each forced breath, her naked body still trembling as she feels her backside being lowed, slid down against the post, sensing the warm, stickiness between her thighs as his thick, long shaft slowly withdraws the rest of the way to slap back and forth across her wet thighs; she slumps in the wrist bindings.  Shaking her head back and forth, glancing toward him with glazed eyes through her matting hair, she whines.  “No!... Don’t… Ohhh… Don’t stop now… Please… Please don’t.”

“You session’s just begun… Time to work off the demerits now.”  He smiles.  “Time to learn to mix pleasure with pain.”  Glancing toward the wooden stocks, reaching out, cupping her chin and turning her face toward the stock, he continues.  “Get you bent over and secured in that… We’ll work these titties for awhile… Do some things to ‘em that’s going to really hurt while I give you your orgasm from behind.”

End Part One