Boarding School Discipline Diary

BOARDING SCHOOL DISCIPLINE DIARY

PART TWO

Chapter One

       Her small room quiet, the steam from the long, hot shower fogging the view from the window along with most of her dresser mirror, she fluffs her hair with a terrycloth towel, allows the other to hang down loosely across her breasts.  Dropping the towel from her hair, clenching, spreading open the other, she glances toward the reflection of her chest, less for wear, barely discolored, the nipples naturally thick on the prominent yet still developing mounds jiggling as she slowly turns, examines herself.

       Spreading her legs a little wider, letting her fingers glide down across her inner thighs inside the opened towel, her fingertips pinching, tugging the puffy folds in separate directions, her clit exposed, the nub protruding into view, she flicks a finger back and forth between the damp slit, envisions his hand, his fingers doing the same.  A soft moan, her breasts noticeably twitching with each heartbeat, she senses the physical transformation, the slippery entry of her finger now unencumbered.  Sliding the finger in a knuckle, two knuckles deep, glancing down past her glistening pubic mound, pressing her thumb across the swelling nub, holding her cuntlips apart with a thumb and forefinger, she imagines his shaft, the thick girth, huge length impaling her again, pressing past her navel, tickling her womb, just like yesterday.

       Her virginity taken the day before although denied an orgasm, finally alone in her bed the past night, she relieved herself a couple times, yet not to the extent she so much wanted.  Working her fingers now, still thinking of the past day, how he threatened to mount her to the stock and take her from behind while punishing her breasts, she remembers him then snickering, returning her to the room with the promise of continuing her sexual education the next day, today.

“Oooohhhh!... Uuuummmmm!”  Audible sighs, her thighs twitching, a second finger pressed inward, burrowing side by side, twisting, curling inside her moist orifice, the masturbation’s soothing, enjoyable, yet still not on the same level of him manipulating her, not to mention how it felt, him mounting her.  Another session scheduled for today, still over a half hour or so away as she glances toward the clock on the far wall, she can’t help wondering what she’s facing, obviously it’ll involve more sex, probably even more pain, but this time hopefully an orgasm.  The note laying flat on the dresser, her instructions, no bondage gear, just basically to be showered, shaved and naked, the towel slips away, drops to the floor as she spreads her hips wider while leisurely pleasuring herself.  Eyes fluttering, having already learned how sexual release dulls pain, another minute or so passing she hears a rap on the door, it swinging open earlier then anticipated.

       “Ready?”

       “Huh?... Ohhh!… Oh, ye… Yes… Yes Sir!”  Her harried response to his question immediate, nervously standing, facing him, she frantically assumes the practiced position, eyes lowered toward his waist as she arches her shoulders back, palms turned outward beside her quivering thighs, feet shoulder width apart.

       Remaining silent, slowly stepping around her, he senses her freshly bathed scent, her damp hair clinging to her shoulders, the moisture still beading across her naked flesh.  Slipping a couple fingers along her waist line, down across the smooth curves of her buttocks, around toward her navel, up beneath her protruding ribcage, his fingers finally cups a breast, lifts, hoists the nipple higher, outward.

       “Quick healer… That’s good.”  He smiles, giving a closer look.  “Means you can receive harsher demerit sessions when deserved, right?”

       A nod, glancing down toward her gripped breast, her nipple tingling to his touch even as it’s bulging between his thumb and forefinger, she mutters.  “Yeh… Yes Sir… I… I guess.”

       “Well then… How are we down here today?”  His voice curious as he slips his other hand between her thighs, slides a finger between the folds of her vulva, his knowing look obvious as he slips his finger back out, lifts the moist tip up toward her flushing face.  “What’s this… What you been doing to yourself?... Masturbating?... Let’s see those hands.”

       Sensing the warmth crossing her flushing face, slowly raising her hands, turning one, the other palm up, she feels the escalating heartbeat in her chest, senses the tell-tale stickiness between her fingertips.

       “Let’s see… I asked you… Have you been masturbating yourself?”  His voice becoming firm, direct, he reaches out, twists, turns her left hand, then her right.  “Answer me… Now!”

       “I… I’ve kinda… I was wiping myself with the towel after showering.”  She fidgets.  “And… And I begin felling, rubbing my… My priva…..”

       “Your cunt?”  He interrupts, shoving a hand up toward her face.  “You mean fingering your cunt, right?... Smell those fingers.”  His stern look ominous, his grip on her wrists tight, he waits for his answer, her humiliating response.  “Tell me you’ve been fingering your cunt…”

       “I… I… I’ve been fing… Fingering my vagi….”

       “Fingering your cunt!... Say it!... You’ve been fingering your cunt!”  His fingernails gripping into her wrists, painfully twisting in opposite directions, forces her to tiptoe.

       “Yes... Yes I… I’ve been fingering my cu… Cunt!”  Her downturned face crimson with humiliation, a tear trickling down a cheek, she blurts out.  “Fingering my cunt… Cunt, Sir!”

       “Go clean yourself… The criterion for you today’s changed.”  His voice firm, slowly shaking his head, he turns, exits the room closing the door behind him as he finishes.  “The Headmistress will handle it from here… Be ready for her!”

Chapter Two

       Silent as she waits, sitting facing the mirror, she stares at her reflection.  Finally, the tap on the door, it swinging open, the Headmistress barely hesitates entering as she scans the room.  Clothed in a black with a trace of white modified habit garb, known as the strictest of the administration in doling out discipline, she steps toward the chair.

“Caught masturbating I hear… Huh Missy?”

Her voice bordering on soft, even toned, almost polite belies the piercing glance of her thirty-something dark eyes.  Meticulous, perfect posture, everything about her reeking of authority, she steps closer, briefly  glances back toward the ward obediently following her, virtually unclothed with only a familiar black leather hood mask concealing her identity.

       “I think we’ll have you remain naked… Just as you are… Yes.”  She instructs as she turns her attention on the ward back toward the reflection in the mirror, to the youthful naked image returning her gaze.  “No mask, no blindfold… Nothing… No anonymity while I have you following us on a roll call in front of the few remaining students waiting along the hall on your way to the discipline chamber… Understand Missy?”

       “Ye… Yes Mistress.”  She answers with a brief nod, the ‘Missy’ thing irritating, the being displayed to the other girls worse, the discipline much worse.  The pit of her stomach churning, her eyes quickly focusing on the floor while rehashing what she just heard, she’s more then frightened, humiliated, realizing the tales about the Headmistress must be as true as the ominous rumors.

       “Now… Here’s some simple rules to follow… First, you’ll cup your hands behind your neck… You’re not to lower them below your shoulders until instructed… Understand Missy?”

       “Yes… Yes Mistress.”  She instantly answers, hoping not to antagonize her.  Raising her arms, interlocking her fingers behind the nape of her neck, she briefly glances toward the mirror for approval.

       “You can arch those shoulders better then that.”  The Headmistress instructs as she hovers behind the chair, also watches the movements through the mirror.”  Lift those elbows higher… Press that chest out… Further… Until… Until it aches, then some… That’s it… Yes… Now remain in that posture.  She instructs, her attention still on the mirror.  “Don’t make me instruct you a second time or I’ll have to use some leather bindings… Wet ones… You don’t want that… They’ve been known to painfully shrink… Even cause dislocations.”

       Arching, bowing, contorting to instructions, she feels her breasts jaunting outward, spreading apart while her arms, shoulders strain as the ward approaches her from behind.  Feeling a slim chain slipping across her neck, the small placard flattening high against her breastbone, her breasts remain exposed as the ward aligns the single worded sign… ‘MASTURBATOR’

       “There… That’s it… Now come with us Missy… And remember… That posture better remain perfect at all times.”

       With the Headmistress leading the way, following just behind her, she clenches her fingers behind her neck, almost reflexively tiptoeing to maintain the awkward posture.  Led down the corridor, face reddening to a bright crimson shade, she notices the half dozen or so wards standing beside the spaced out doors to their rooms beneath the dimmed ceiling lights.  Each at attention, each in matching school gowns, and each gazing straight ahead through the narrow eyelets of their own black leather hoods concealing their identities, each maintains their obedient positions.

       “Your counterparts deserve to know your blasphemistic indiscretions… Don’t they Missy?”  The headmistress scolds, more then loud enough for each individual to hear as they pass by, momentarily hesitating time and again.  “Have a right to know if there’s a possible pervert in their midst who likes to masturbate… Let’s give them a good look so they know who you are when the Holiday’s over… When having to share the showers with you.”

       The peering stares, the painfully awkward posture maintained exposing her completely naked body, the small black lettered white sign pressing against her chest as she’s humiliatingly displayed in front of each girl individually, she can’t wait to get past the corridor, even though her discipline session awaits.

       The end of the corridor, the series of black-iron steps divided by landings with hazed window panes reflecting light, on down past the main floor, into the bowels of the institution, to the isolated discipline area only whispered about.  Fresco laden arches stretching to the ceiling, the stone foundation terrain of the sub level, she’s led to a chamber with just a wooden framed bench mounted to the center of the floor.

       “On your backside… Spread out… It’s obvious where your hands and feet go.”

       Brass shackles affixed to either end of the bench, cranks, handles to either side of the apparatus, she hesitantly obeys, lays slowly back across the surface, stretches out her arms and legs to the restraints.  The ward obviously accustomed to her duty begins by undoing the sign’s chains.  Fastening the shackles to each wrist, she steps toward the end of the bench, begins adjusting, fastens the lower restraints one after the other.

       Arching, buttocks and shoulders pressing across the flat wooden surface, glancing across at the Headmistress while still being shackled, watching her slipping out of the traditional garb leaving only the wimple and veil of her habit, her almost nude body glistens beneath black leather straps as she turns.  The contoured straps crisscrossing, barely covering her pendulous breasts, her pubic area, seeming to be some sort of designed bondage gear held together by shinny metal ‘O’ rings, the image appears so surreal, unimaginable.

       “Well Missy… Shall we commence?”  Her voice strict, her appearance somehow forebodingly beautiful, masochistically erotic, her full breasts pressing outward against the crisscrossing bowing straps, lower down, the ’V’ shaped leather barely covering the noticeable bulge of her pubic area, the veil covering her head and shoulders, revealing just her rather striking face, she holds the thick handle of a modified black leather bull whip in one hand, ominously flexing the tapering smooth surface in the other.

       “Shall we start with the breasts first… Then work our way down to the thighs.”  She asks no one in particular while slowly stepping beside the bench.  “Then I think we’ll concentrate on the vaginal area.”  Allowing the stubby whip to flex back and forth in her hands while verbally dissecting her shackled charge, she continues.   “We’ll give some special attention to those nipples… Then of course that clitoris would be appropriate to taste the tip of the bullwhip a few times too, don’t you think?”

       Glancing toward the ward in her submissive position, she nods back toward the mounted table, toward the youthful bare breasts jaunting upward, outward, spreading, swaying with each breath.  “The gel… We need to administer the thicker salve.”  She nods.  “Spread… Plenty across both Missy’s mounds… Especially those perky nipples… And between her thighs, too… Work the stuff in good.”  Standing directly in line with the heaving breasts, staring toward the jiggling nipples while slowly nodding her head, she continues.  “Yes… We don’t want to lacerate her flesh during her session if we can help it… Bruisings’ to be expected… And of course welts… Just don’t want to scar her yet, if we can help from it… That would be a shame on someone with a developing body that’s so promising.”

       Leaning over, the leather barely covering her own breasts flattens between the bare breasts thrust upwards as the Headmistress whispers.  “Don’t worry Missy… I’m not going to maim you… Oh, the pain’s going to be quite discomforting to start with… Leave some bruises like I explained… But, you’ll get past that… You’ll see… Then I’ll tickle that clitoris you’re so fond of… But like I said… Don’t fret… The bruises will only last a couple… Maybe a few days at the most.”  Intentionally grinding her breasts back and forth, the straps of leather stretching between the pairs of firm mounds, she continues.  “Maybe before we’re done… We’ll see if you’re a pervert or not… See if your pain becomes your pleasure.”

       Gazing up from the bench while the Headmistress takes a step back as the ward steps closer, almost instantly feeling the cold globs of gel melting as they soak across her breasts, the fingers melding, stroking, stretching at her bare flesh, she arches, reflexively tenses, nibbles across her lower lip while closing her eyes.  Frightened, confused, yet the sensations of the soaking salve invigorating,  inhaling a deep, slow breath she senses her left breast, the other smothered with more gel, spread out in layers, the coolness slowly warming, resonating through her tingling nipples, spreading like expanding ripples throughout her chest as the feminine fingers continue kneading, melding in circular motions.

“Ahhh!”  Unable to suppress a moan, a short groan, her body beginning to tremble, her stomach hollows, quivers as moist fingers glide down past her navel, slide up across her pubic mound.  Another deep breath, holding it in as she senses the drippings of gel across her spread thighs, her labia lips, the nub of her clit, she feels her hips reflexively jerking, her buttocks vibrating uncontrollably across the harsh surface.

“Ahhhhh!”  Fists clenching, toes curling, wrists and ankles twisting in the taut confines of the shackles as her back bows, she experiences the ward’s sensitive fingertips penetrating her moist orifice, sliding inward, twisting, curling back and forth, masturbating her unlike she could herself, the coolness becoming warmer, ever warmer like the tingling sensations encompassing her jiggling breasts.  “Oooohhh!”

       Flexing in rhythm with the penetrating fingers, sensing more then one, maybe two or even three spreading her cuntlips apart, gliding in a couple knuckles or more deep, she feels the other hand cupping, again massaging her breasts, back and forth, teasing one nipple, the other, tweaking and tugging even as her clit’s twisted and tugged between those moist fingertips in unison.

       “Moans, squinting her eyes, she accepts the manipulations, even relaxes somewhat.

       ‘Thwack!’

       “Aaaaaagggghhhhh!”  The crisp sensation’s instantaneous, both nipples burning, simultaneously jiggling beneath the flexing leather snapping across her breasts, her naked body reflexively arching in the restraints, her subtle moans’ becoming a harsh squeal.

       “Silence!”  The Headmistress rasps.  “Hush or I’ll really lash these titties to give you something to cry about… Now concentrate, and remain quiet… Bite your lip if you must.”

Another crisp snap of leather across the still quivering mounds resonates across the cravenness chamber, another guttural response, this time suppressed; again her body bows upward, stretching tautly in the bindings, faintly discolored welts streaking across her bare flesh, crisscrossing her puckering nipples.

       Stepping closer, the tip of the stubby bullwhip dangling, scraping across the floor, the Headmistress leans over, examines the pairs of fresh reddish stripes.  Glancing toward the ward, waving her toward the bottom of the table with a nod, reaching out, cupping a quivering breast, squeezing its glistening base, the gel still oozing, spreading between her fingertips, she smirks.  “That’s the first couple lashes… Actually just invigorating flicks like I said… And imagine… These nipples are getting rock hard… I don’t know if you’re a pervert after all… Or just really kinky!... Hear me Missy?... I asked… Hear me?... Are you into pain, too?”

       Blinking, glancing down toward her aching breasts, she nods, mutters.  “Ye… Ohh… I… Don’t know Mistress… I… I guess.”

       “Well then… Let’s continue… Shall we warm these titties up some more while she rubs more lotion between your thighs?... See how you react?”

Flipping her wrist while slowly stepping alongside the rack, she focuses across the glistening mounds, the swollen nipples as the ward obeys, swabs a glob of gel between the spread thighs in front of her.  First one flick of the whip, then another, another, finally another, the cadence of leather smacks firmly, yet not that harshly across bare titflesh, echoes off the stone pillars.

Each lashing bringing a muffled squeal, a silent grunt, her body twists, arches, stretches in the shackles from the sensations of both the Headmistress’ whip and the ward’s fingers.  The strokes still crisp, yet more then bearable across the jiggling nipples, the leather springing across both slippery mounds; the burning sensations resonate through her swaying breasts, her manipulated vaginal area tingling simultaneously.

       Again lowering the bullwhip, stepping toward the center of the rack, glancing across the bulging mounds beading with moisture, narrow bruising welts layered across both, the Headmistress nods approvingly toward the ward still using her fingers, melding in the oozing gel at the other end of the table.  “Okay Missy… Guess I was right… Hum… Look how puffy those nipples have become… How they’re responding… Actually makes you want more, huh?… Kind of enjoyable… Huh?... Now… Let’s start at these titties and work our way further down with the whip while she’s getting you in the mood, too… Okay?”

“Humph!”  A muffled nod as the leather creases flesh, turning her head, the warmth spreading throughout her chest, her vagina, gazing toward the bullwhip being flexed, snapped back and forth beside her naked body, seeing a quick flick of the Headmistress’ wrist, the supple tip of the black whip uncurling, she closes her eyes, muffles a grunt as she feels the stinging burrowing of leather sinking into her flattening stomach muscles just above her navel.

Her breath escaping her lungs, rasping, grunting as her body tenses, arches across the flat surface to the crisper pain, still the ward’s fingers jamming deeper into her moist slit, she blinks, turns her head as she sees the curling black snake again snapping downward toward her midsection, feels the fingers still burrowing inside her stretching vulva.  A painful few inches lower, the sound of leather smacking abs, the welt streaks across her front side just above her pubic mound.  Again lurching in her restraints, fists clench, toes curl as her buttocks grinds between the flat surface and the ward’s twisting fingers.  Eyes tightly squinting as she again gasps for breath, her body uncontrollably shivers, trembles from both the pain and the pleasure.

       “You’re no longer needed at this time… Return to your room.”  The Headmistress’ voice firm as she nods toward the ward.  Stepping even further down along the rack, she lets the bullwhip drop to the floor.

       The ward obeying with a silent nod, turns and leaves.  The chamber momentarily quiet, breaking the silence, the Headmistress reaches across, gently massaging the glistening mounds across the crimson welts, whispers.  “I understand your virginity was taken yesterday… Let’s see.”

       Sliding an open palm down the naked body spread out beneath her, spreading fingers flittering across the pubic mound, she whispers.  “Well Missy… Let’s get a closer look at that little thing that’s getting you in all this trouble.”  Parting the glistening labia folds as she leans across the table, letting her lips brush across an inner thigh, her tongue to briefly flick the nub of the engorging clit, she gives a soft giggle as she watches it quiver.  “Sensitive, huh?... Like to play with it yourself… Or have me show you how to give it a real workout?”

       Arching, responding to the tongue again flicking a couple more times back and forth across the very nub of her clit, suppressing a moan, her entire body trembles in anticipation.  “Ohhhhh…. Oh… Yes… Yessssss!... Ohhhhhh!”

       Stretching the puffy folds a little wider, watching the youthful hips spreading, arching upwards, the Headmistress again smiles at the sight of the quivering vagina, the actual fluctuation of the moist flesh responding to her teasing licks.  Striping the leather bottom, dropping it to the floor, stepping toward the front of the bench, she instructs.  “Missy, I want you to do to me exactly what I’m going to be doing to you.”  Placing one knee, the other across the head of the bench, hoisting herself up, leaning, aligning her face directly over the youthful vagina, pressing her own vagina against the girl’s face, she shuffles, twists into position, lowers her head, rasps.  “Just do as I do now.”

       A flick of her tongue across the responding clit, momentarily waiting as she glances back, feeling a hesitant response, the pleasant but obviously unpracticed lap across her own spread slit, she smiles, again  lowers her parting lips to either side of the moist nub, sucks in, flicks her tongue back and forth, her head gently twisting between the twitching hips.  Gripping both thighs in her spreading fingers, sensing the quivering, the reflexive contortions, she sucks a little firmer, gently gnaws on the stretching clit.

       Sensing lips smothering her own vagina, teeth not so gently pressing into her exposed clit, a firmer nibble then comfortable, she clamps down herself, gives a warning twist, hears the muffled moans, feels the girl’s teeth quickly releasing, feels the more pleasurable suction of her clit, the tingling of a moist tongue flicking back and forth, up and down.

       “Yes… Yes Missy… Yessss.”  Whispering between licks, flicks, gentle nibblings, the Headmistress’ hips quiver beside the firm mounds pressing up against her stomach as her own clit’s manipulated, worked.  “Yes… Huh huh… Just… Just like me… Yes!”  She rasps between breaths.  “Do… Just as I… I do to you… Oh… Yessss!”

       The thought of doing the youthful, so inexperienced girl exhilarating, her amateurish responses seemingly even more enjoyable then doing a more experienced, knowledgeable partner, she rocks her own hips back and forth.  Seeing, feeling the girl’s awkward mimics, flicking her own tongue back and forth, again gnawing on the ever quivering clit, sensing the more gentle responses in kind, she can feel the stirring, the churning in her womb as their bodies press together, trembling, grinding across the table in unison.  Groans intermingling, stomachs, hips both in a series of short spasms, the table vibrates beneath them as their groans become grunts, sighs.

       Laying momentarily still, slowly rising, stepping to the floor, the Headmistress leans down, places her lips across the girl’s.  A soft, slow kiss, a nibble on the lips, she smilingly glances into the youthful, hazing eyes.  “You got your cherry broke both ways now, didn’t you?... You’ve got so much more for me to teach you in the days ahead… So much more.”

END PART TWO