“Tell me about her…”
There’s curiosity in your voice. I can hear it.
You remind me of her. Not your accent, of course, but your natural inquisitiveness. The way you probe and question hints at a voracious intelligence, that hunger to explore and examine, to strip away my facades and see what lies underneath. Just like she always did.
More than once I can remember her telling me: the deeper you delve, the more interesting a story becomes. Causes and effects are suddenly revealed, how sometimes the fickle finger of fate nudges a pebble, and we are the avalanche.
Isn’t it funny, I almost never got to know her at all.
We like to believe we’re the masters of our destiny, proud tall ships unfurling our sails, as we turn the wheel and boldly follow our compass. But that’s just a comforting delusion, in reality we’re little more than rowing boats, buffeted by the capricious currents of circumstance.
What are the forces and factors that come to shape us? What are the petty chances and coincidences? What were the influences that truly fashioned me? What formed my personality and my sexuality? And where did my fascination with spanking come from?
And at the centre of every answer, is her.
You’re already intrigued, I can tell. Even though I can not see you. My naked body is already exposed to you, bound by my wrists to the top of the bed. Now I know you want me to expose my deepest secrets as well.
But dare I reveal myself? Dare I drop my mask and tell my story?
Perhaps I shall.
* * 1 * *
The story of who am I really begins during my school-days, though I doubt you’d recognise my younger self. I was reticent and introverted, doing what I could to avoid drawing attention to myself, preferring the anonymity of crowds and the solitude of quiet spaces. By then, I’d been at my grammar school for several years, and like many of my peers I was a typical jumble of teenage ambitions, misconceptions and impulsive hormones. Although it must be said, some of my schoolmates concealed their inner insecurities much better than most.
There are some locations that come to define us, someplace where something remarkable happens. Yet I’ve no idea what lead me to lurk there, perhaps I’d just been swept along as several unknowable forces converged, a quirk of the school timetable, an eccentricity of the my grammar school’s layout, a relic from the building’s lengthy history. All coming together like ripples meeting in the middle of a pond; sweeping me along like a leaf.
As I recall, I’d wanted to be close to my next class during break time, and I’d stumbled upon a little alcove just a few minute’s walk away. It provided a quiet place to sit, a somewhere I could relax and clear my head. This particular corner of the school must have been one of the very oldest parts of the building, as above the alcove I found was an ancient wrought-iron staircase, which lead to the classrooms on the first floor. But being at the corner of the building, few people ever came this way, preferring the more direct route between the school buildings across the diagonal paths of the rose-lined quad. This accident of architecture created my little secret spot, providing me a sanctuary where I could retreat and doze undisturbed.
I’m not even sure how it first happened, but one day I remember idly gazing upwards through the stairs’ black painted latticework, and being amazed to catch a glimpse up one of my teacher’s skirts. She had stopped to chat to one of the older girls, and was standing with feet on different steps, balancing her weight with her legs slightly apart. From where I was sitting the view up her skirt was like peering into a dark tunnel, only there was light at the end, a light patch that I realised was her underwear. Yet instead of being shocked, I was transfixed.
The moment passed quickly, the teacher resuming her passage overhead and down the stairs, whilst I blushed unseen in the alcove, pointedly staring at my feet. My peeping had been quite out of character for me, normally I’d never have considered spying on others. And yet, when the opportunity had occurred, that’s exactly what I did. I had looked up a woman’s skirt, and stared at her knickers. More than that, I was secretly disappointed I didn’t catch sight of more.
After that, I began to spend more and more time lurking beneath those stairs, like some spider in a web, waiting for someone else to halt above me. I found the clunk of footsteps meditative; girls and boys had their own distinctive cadence. The wide heels of the girls’ shoes clip-clopping in time with their elegant gait, whilst the boys flat soles slapped and thudded as their owners slouched upwards or skittered downwards. Sometimes I saw it, a flash of white through the black ironwork above me, a momentary glimpse of what I knew to be underwear. And behind that thin strip of material, I knew, lay magical, feminine secrets.
I don’t know when my Headmistress first noticed my interest in those passing up and down the staircase. To be honest I was rather oblivious of everything around me, my attention fixed on those passing by, through the little gaps above my head.
But one day she approached me as I sat there, staring upwards. She didn’t make a fuss, simply addressing me by my first name to secure my attention. I remember the shock that coursed through me when I saw her, standing just in front of me, and how immediately guilty I felt inside. Without saying any more than my name it felt like she’d reached inside me and squeezed my stomach.
Any lingering hope I had that my crime had not been noticed was dispelled by the only other words she spoke to me:
“Please visit me in my office after classes today.”
And just like that, she turned and walked away, leaving me slumped against the sides of my sordid little alcove, dizzy with shame, my heart thumping in trepidation.
Shall I continue?
* * *
Later that day, when the school bell rang, the school seemed to empty usually quickly, as if some latent crisis was unfolding, and the premises needed to be urgently evacuated. But then again, it was a Friday. Usually I’d be part of this rapid exodus, hurrying to the bus stop outside the school gates, eager to beat the queue and get home to start the weekend as soon as I could.
When I stashed my books and bag in my locker, my hands were trembling. I’d never needed to stay behind before, now just a handful of stragglers wandered amongst the empty corridors, there were hardly any after-school clubs on a Friday. Every now and then I’d encounter a teacher locking up a classroom, or strolling to the carpark, burdened by tall piles of jotters and folders, like some particularly well-educated sherpa.
Her office, the Headmistress’s Study, was in the school’s oldest building, a miniature cathedral of Victorian redbrick, a latter-day temple of learning. I approached via her secretary’s office, itself at the end of a long corridor of glossy emerald green tiles. The very fact a visitor had to enter one intimidating room in order to reach another of even great importance made me feel like I was approaching an antechamber to a Pharaoh’s tomb.
I was tremendously relieved to discover the secretary’s room empty, her desk already cleared and no sign of her possessions. Ahead, a honey-coloured wooden door loomed, seeming to grow in size with every successive glance. A brass plaque glowed in the late afternoon sunlight.
I tried to knock as discreetly as possible, but I clearly remember my rapping somehow reverberating thunderously. I half expected to hear the cries of a dozen startled ravens squawking outside. There was a moment of silence as I held my breath, wondering – earnestly hoping in fact – that she’d forgotten all about me. But then her voice called out from the other side of the door, proud and clear.
Reluctantly, I pushed the door handle and shuffled into her room, tugging the door closed behind me, lest someone behind me glimpse my walk of shame.
My eyes instinctively surveyed her study, my caveman brain scanning for the thicket ahead for snarling sabre-toothed predators. Her room was comfortably furnished, a cream-coloured soft pile carpet underfoot, a brown velvety sofa, and a matching armchair. The walls were painted a warm white rather than wallpapered, and three enormous wooden rafters loomed high overhead. And by the large bay window was a timeworn oak desk, behind which she sat silently and imperiously, a single elegant finger beckoning me closer.
I’d only been in her office once before, when I’d first visited the school for the entrance interview. Come to think of it, that had been the last time I’d spoken to her. I distinctly remember entering her room so timidly, feeling like a tiny mouse crawling towards a sleeping cat. But on that occasion she’d been so kind to me, greeting me warmly and inviting me to take the sofa whilst she sat nearby on the armchair. She had quickly put me at ease with her easy smile, and then teased from my stuttering mouth my interests and ambitions.
This time, however, she didn’t even say hello. Her captivating smile had been replaced by a disquieting glower. I dared not meet her disapproving gaze, and ended up staring down at my shuffling feet, which only earned me a swift rebuke.
“Stand up straight!”
I did my best to comply, straightening my guilty slouch, raising my chin, forcing myself to look at her.
Miss Snow was eye-catchingly attractive, one of those individuals who seemed to radiate a presence that made those around her eager to please. She wore her sandy blonde hair in cheek length bangs that framed unblinking cool blue eyes, with just a discreet touch of matte red lipstick. She dressed conservatively, a white blouse, three buttons undone, and a navy knee-length skirt, over which she wore her black academic gown. She was probably old enough to be my mother, but I was at that impressionable age when I considered all women to be fascinating and beautiful. Even now, years on, I still believe that.
There was one of those awkward pauses as we seemed to be evaluating each other, and then she broke the silence.
“You…” she said accusingly, “have been a very naughty boy.”
“Yes Miss” I admitted readily.
“I’ve been watching you underneath the Old Building stairs for weeks. I know exactly what you’ve been doing there.”
I was mortified. I thought I’d been so discreet, so unobtrusive. But it was also true that I‘d been in a world of my own, staring upwards and between the passing feet, quite oblivious to what was going on around me.
“I am very disappointed.” she tells me, “The mission of this school is to turn boys into young gentlemen, and I consider peeping to be the most unmasculine of behaviour.”
“Yes Miss. I’m so sorry, Miss” was all I could manage in reply, in a weedy timid voice that just confirmed her criticism.
There was another excruciating pause, as my judge pondered my sentence.
“The only fair punishment is to dress you in a skirt for a day, so you can appreciate what it’s like to be gawped at.”
“No Miss! Please!”
I pleaded for mercy, my face burning red hot with shame, my eyes almost watering with tears.
If I was made to wear a dress around school I’d be a laughing stock. Even worse, I knew I wouldn’t be able to justify it, not without admitting I’d been a dreadful pervert.
“Please, Miss…” I implored, “anything but that.”
No longer able to hold her gaze, I looked behind her. That was when I noticed the cane resting on two hooks on the wall.
“I see no alternative” she stated bluntly.
I remained silent, lacking the words to argue for an alternative punishment, just staring at the cane, my eyes traversing its long straight edge and its curved crook handle. Even on the wall, it looked intimidating. And painful.
A long awkward silence developed. She must have noticed my attention had wandered, and she turned her head, following my gaze to look behind her.
“Oh…” she exclaimed. “We don’t use that anymore.”
Guilt, shame and desperation overwhelmed me. I could hear myself whimpering.
I can still remember forcing myself to look at her with imploring eyes, and how she looked into me, deeper than anybody ever had, as if she was scrutinising my very soul.
“Have you ever been spanked?”
She pondered my reply silently, pressing her fingers together in front of her face, until she slowly rose to her feet, and walked around her desk and past me. I heard a subtle click as she locked her office door. Then she approached me, placing a finger underneath my chin, and raising my face so she could look down at me.
“Very well, young man. You may be punished the old-fashioned way.”
I felt the pressure of her finger under my chin increase for added emphasis.
“I expect complete obedience, boy. If you disobey any of my instructions I shall stop, and you can spend a day in a skirt instead.”
“Yes Miss! Thank you Miss.”
“Then we’ll begin. Do you know how naughty boys are punished?”
“Er… no… Miss” I admitted hesitantly.
At the time I didn’t have much experience of corporal punishment, but I must admit it had intrigued me whenever I’d stumbled upon it – which had chiefly been in comics and books. There’d been a particularly memorable episode of discipline in Tom Sawyer, where he’d been caned in front of his class to protect the girl he adored, an act I’d always considered incredibly noble. I’d even seen a few spankings in films, which usually involved a miscreant bending over, and then a few off-camera smacks and squeals. My headmistress was about to shatter my tame preconceptions.
“Naughty boys get six of the best on their bare bottoms.”
She withdrew the finger that was holding up my chin, and I felt myself gulp, but I didn’t dare contradict her, and merely compliantly nodded my agreement. My eyes followed her finger as she pointed to some vacant hooks on the wall.
“You may hang up your blazer.”
I did as she instructed, and then walked back to stand where she indicated in the middle of the room.
“Now take down your trousers.”
My shaking hands fumbled with the button and then the fly at my waist, before I was able to slip a couple of fingers in at each side and slid my trousers off my hips. They bunched around my thighs, so I needed to tug them further down to my knees. But a stern look from my headmistress indicated she expected my trousers all the way down, so I bent over and pulled them down to my ankles.
“Now pull down your underpanties.”
It was a shock to hear my underwear being referred to in such childish language. But I could recognise her intention well enough, to ensure I really did get to feel like a naughty little boy.
From my crouching position I reached upwards to my waist and hooked my fingers into the elastic of my underwear, tugging it down in one swift movement, so quickly I didn’t allow myself to dwell on what was actually happening. I consoled myself with the thought that at least being bent over like this, Miss would not be able to see my privates. Looking back now across all these years, I find it ridiculous I ever thought that mattered.
I kept my head down, and could hear her footsteps moving away – and then a little rattle as she must have plucked the cane from the wall. I heard her footsteps returning, accompanied by several ominous swishes as she experimented, probably loosening her wrist, getting a feel for the rod in her hand.
“Now, the first lesson naughty boys learn is proper posture.” she stated primly as if channeling the spirit of a Victorian governess.
The tip of her cane tapped my calves and then my thighs until I straightened my legs. I got taps on the backs of my hands too as she encouraged me to straighten my arms and grasp my hands together behind my ankles. And a few taps on my bare bum too to ensure I stuck it out at the right angle.
“The next lesson naughty boys learn is gratitude.” she said cryptically.
I was still ruminating over what she meant when her palm slapped one of my buttocks, leaving a fiery sensation that lingered long after the impact had faded. Then there was a moment of calm, as if she’d given me time to appreciate the tingling in my bottom – the very first spank I’d ever received.
Then a second smack landed, then another, and another. A burning sensation was rapidly spreading across my whole bottom, confusingly I could feel the impact of her palm each time, although I’d been steeling myself for the swoosh of her cane. Another flurry of spanks heated up my bottom further, amplifying the tingling into a lingering sting.
“It seems the second lesson is more difficult to learn.” she observed.
It took me a moment to recognise I was the target of her comment, and to refocus my attention away from the fiery pain in my behind, and engage my faculties instead. As soon as I repeated back her words inside my head, I realised immediately what she’d meant, and what I had been expected to do.
“Thank you Miss!” I exclaimed.
“That’s better,” she commended in a rather patronising tone, “a good boy should always be grateful for his discipline.”
A chilling swish cut the air just behind me, making my legs stiffen apprehensively.
“Now, the final lesson naughty boys learn is acceptance.”
She didn’t elaborate any further, and just ran her cane across my bare bottom, still tingling from her earlier assault. I could feel the length of the rod as she rested it against me, as she moved it laterally, like a cellist working their bow. A cruel tease to add to my trepidation.
Suddenly there was a rapid swish, a crack, and a hot line of pain seared across my bum.
I yelped, instinctively, as if I’d just sat down on a fire, wiggling my bottom childishly, as if I’d caught alight and was trying to waft out the flames. Seconds later I realised how silly I must have looked, and immediately berated myself for my unmanly lack of fortitude.
The initial whack was a flash of lightning, shockingly sudden but gone in an instant. It was followed by an enduring rumble of thunder, a throbbing burn that glowed and lingered. I could feel the aftermath tingling in my balls.
I heard my disciplinarian give a little sigh, as if she was expecting something that had never came, and then after a brief lull, a second swooping swish heralded another excruciating whack. Again my knees wobbled, but this time I managed to muffle my discomfort. I had no cause to plead for leniency, I knew this was, after all, no less than I deserved.
“Thank you Miss” I whimpered, guessing that was the show of acceptance she expected. I didn’t cry out or make a scene this time, which didn’t go unnoticed.
“Good boy. Five more.”
It took an age to receive my remaining whacks. After each stroke she would pause, and run her fingertips along the stripe she’d just inflicted. I couldn’t be sure if this was a courtesy to me, a few extra moments to allow the sting to fade, or a genuine fascination with what her cruel cane had done.
I took the remainder of my caning as stoically as I could, holding my breath until each initial flash of pain had ebbed away, then thanking her for punishing me. I felt so childish bending over in such a submissive position, my bare bum on display. But I knew without being lectured that discipline wasn’t just a few smacks on the arse, it was acknowledging I deserved to be punished, to admit to myself I’d been a disgracefully naughty boy.
Something else was happening too. Between my legs I could feel my penis dangling heavily, and my scrotum seemed to feel tighter after each successive whack. After the third stroke I began to feel my swollen member resting against my inner thighs. After the fifth, I was no longing dangling but conspicuously erect. By the end, my face was as hot and pink as my arse, my cheeks burning with shame; my headmistress had just spanked me and given me a hard-on.
“Thank you, Miss!”
I gasped moments after the final whack had scorched across my bum. I was keen to make my deference quite clear, lest she think I needed more.
“I was a very naughty boy, Miss. I’ve deserved a sore bottom.”
She walked around me and set the cane on her desk.
“Now, stand up straight. Let’s have a look at you.”
My hands left my ankles and fled to cover my crotch, as I naively tried to hold my erection against my body.
“Hands on your head, boy.”
I knew then it was hopeless, I was powerless to preserve my modesty. I raised my hands to the top of my head and my erection sprang forward, pointing towards my headmistress like an accusing finger. I was terrified she’d shout at me, that she’d accuse me of being a horrible little pervert – but her expression didn’t change, as if there was nothing special to see, nothing she hadn’t seen countless times before.
Despite her dismissive lack of interest in my nudity, I stood mortified in the middle of the room as she turned her back on me and walked over to her desk. I watched as she opened a drawer, and was surprised to see her take out a tape measure, a pencil and a little notebook. When she returned she knelt in front of me, examining my foreskin, pulling it back slightly to inspect the bright pink knob of my glans, and then cupped my scrotum in her palm, as if gently evaluating my balls.
You can imagine my shock when she unspooled the tape and began to take measurements. She used it around my cock first, establishing my girth, and then she determined my length from the tip of my cock to its base. Next she measured me like a tailor might, around my waist, my chest and my shoulders, even my inside leg and inside arm too, halting every time to record each vital statistic in her little book.
Finally she made me shuffle to the side of the room, my trousers still around my ankles. I had to stand up straight against the wall as she took my height. That was an immensely embarrassing experience, I hadn’t been measured like that since I was a little boy. Although it did have a compensation, the cool wall felt so good, so soothing against my poor burning bottom. I’d have loved to have stayed in that position, but Miss insisted I put my hands on my head again and turn around to face the wall for a period of silent contemplation.
There was much to meditate on. So many life firsts, the first time I’d been exposed in front of a woman, my first ever spanking, the first time I’d become hard without touching myself. Meanwhile my headmistress returned to her desk, and from behind me, I heard scribbling.
I’ve no idea how long she left me standing there, but it was long enough for my erection to soften, and the stinging in my bum to subside. I was instructed to turn around, look my headmistress in the eyes, and given one last lecture about what happens to naughty boys. Finally I was allowed to pull up my underwear and trousers.
“I expect to see you here again same time next Friday afternoon, after classes.”
I groaned inside, but tried not to show it. I had hoped my punishment had concluded and my slate was now wiped clean. Clearly though, my misdemeanor required some further intervention.
Sometimes you decide to say something, forming the words in your mind before delivering them to your tongue. But sometimes words just emerge almost automatically, bursting forth unthought and unvetted, with a natural sincerity that can’t be faked. So what I found myself saying next came as a complete surprise.
“Thank you, Miss.”
My words seemed incongruous. What was I thanking her for? Thank you for robbing me of my modesty, for beating me, for inflicting shame and pain on me with a Victorian-era corrective relic. Thank you for humiliating me, and for your intention to do it all again next week. My logical mind baulked at what I’d said, but there must have been a part of me that that was genuinely grateful. And to that part of me, my headmistress smiled.
I walked away from her office in a daze, my footsteps echoing through the empty school corridors. When I got home I hurried to my room, locking my door, throwing off my school uniform and pulling down my pants to examine my marks in the mirror. There were several thin pink lines on the lower half of my buttocks, faint stripes rather than the vivid red weals I’d expected. It didn’t hurt, just a lingering tingle and a dull ache when I ran my finger across the little raised lines.
I also had a remarkably hard erection. If this was the effect of a caning, it was no wonder Tom Sawyer had volunteered to take one on behalf of Becky Thatcher.
Naked, I lay back on my bed, massaging my stiff cock as I pictured Tom examining his marks, just as I’d just done. And in her own elegant bedroom I imagined beautiful Becky slipping her hand into her bloomers as she replayed Tom’s caning in her mind, secretly wishing she too would get the discipline she so earnestly craved. To be told to bend over, to feel her dress being lifted, and her bloomers parted. And then – as she delicately stroked her most intimate folds – imagining authority’s cruel rod mercilessly whacking her bare little bottom.
* * 2 * *
My return visit to my headmistress dominated my thoughts for subsequent week. Alternating tides of dread and excitement washed over me as I tried to picture the horrific humiliations that might lie in store, scenes that were assuaged by an unexpectedly intense erotic buzz. Since my last visit my fantasies had never been so vivid, so varied, or so enjoyable. It was as if what I’d experienced in the short time I’d spent with her had massively expanded my erotic vocabulary.
That week seemed to pass in a blur, until finally the Friday afternoon bell rang and the school emptied rapidly, and I found myself trembling nervously in front of the headmistress’s door once more. This time when I knocked, and answered her summons to shuffle nervously inside, she greeted me with a sly knowing smile.
Being in her commanding presence made me feel like a small boat, bobbing on stormy seas, approaching a lighthouse. She loomed over me, occasionally sweeping me with her gaze that made me flinch and avert my eyes, as if I was being dazzled. I knew the jeopardy of getting too close, yet invisible inexorable forces seemed to draw me towards her.
When I lowered my eyes I could see several garments lying neatly folded on the desk in front of her. And disturbingly, one of these garments was clearly a skirt.
“Yes. I’ve got you a little present!” she beamed, clearly noticing what I was staring at.
“I used your measurements to get a schoolgirl uniform from our stores, it should fit you perfectly!”
Meekly, I thanked her as best I could, trying not to sound too disrespectful, but inside my heart had sunk.
And then she offered me a choice: either I could wear my new uniform to classes on Monday, or I could put it on now, and go for a walk around the almost empty school with her. But if I chose the latter, on our return to her office I would be caned like a naughty girl.
This choice really wasn’t a choice at all. Dressing as a girl for a day in a crowded school, and being teased for the rest of my schooldays, or a few minutes of embarrassment followed by a sore bottom. I told her I’d get changed now.
She nodded, seemingly unsurprised by my decision, and watched me as I began to undress and fold my own clothes neatly on the sofa. Funnily enough, having already exposed myself in front of her last week I felt much less self-conscious when the time came to pull down my underpants again.
Eager to regain my modesty, I reached for the pair of white knickers on her desk first, but she beat me to them, and to my considerable surprise, instructed me to hold my foreskin and pull my penis back between my legs. I did as I was told, flattening my scrotum against my body between my legs, so it was reduced to a fold of flesh either side of my penis, like a crude parody of a girl’s cleft.
Then she knelt and examined me, then held the knickers open by my feet, and invited me to step into them. I continued to hold my willy in place until she’d pulled my knickers up snugly to my waist. How weird it was to then look down at my own body and see a girlish curve in place of my familiar bulge.
She passed me the uniform skirt next, I’d never worn one before, but it seemed logical to step into it as if it was a pair of trousers, and then reach down to pull it up to my waist and button it closed. It was a dark charcoal grey, pleated all around so it flared slightly outwards, ending just above my knees.
The next garment she handed me was a padded bra. I needed some assistance to put that on, my headmistress showing me how to put my arms through it and then helpfully fastening it behind me. Its cups were small, but fitted snugly against my downy haired chest, the foam interiors providing me with visible mounds. I put the white blouse on next, then tied my tie, before pulling up my white calf length socks and the modestly heeled shiny black shoes she’d provided. Finally I donned my own blazer, and stood upright for her inspection, my transformation complete.
“How lovely,” she said admiringly, “now come with me, young lady.”
My headmistress strode purposefully out of her study, and I followed obediently in her footsteps. I felt like I was wearing a disguise, with a sense of not belonging that made me feel like a burglar on the prowl. I desperately hoped no one would spy me as we trod the deserted corridors. The school was not completely empty, occasionally I could hear the distant thud of a door closing or the scuff of running faraway feet. But I knew my awful secret would be safe as long as we avoided anyone who might recognise me, which made me begin to wish my new outfit had also included some makeup and a wig.
Suddenly Miss Snow abruptly turned to our left, pushing through a door into a forbidden realm I’d never dared enter before: the Girls’ Lavatories. I followed hesitantly, partly intrigued, but mostly terrified of who I might encounter.
As it happened, the white-tiled room was empty. I think what surprised me most was that it wasn’t a gleaming temple of hygiene. Tissues and paper towels lay on the floor, discarded and forgotten. The shelf by the sinks had accumulated several tampon wrappers and disposable contact lens foils, and beneath lay the puddles of a day’s worth of drips, splashes and hurriedly washed hands.
Most of all I expected it to smell different, perfumed somehow, like some luxurious cosmetic emporium. But it didn’t, it smelt like any other toilet, the acrid scent of disinfectant mostly masking the whiff of bodily functions. Up until this epiphany I‘d always idealised girls as beautiful fragrant angels, but now I was beginning to realise that they really were just as messy and pongy as the rest of us.
However, I think my headmistress’s real intention in bringing me here was so I could look into its full length mirror. There was something dizzily unnerving about gazing at the reflection, it mimicked my movements, but I felt weirdly disconnected. It was as if I was looking at a chimera, my head on a schoolgirl’s body. My gaze lingered on the curves of my faux bust, fascinated to suddenly be inhabiting this feminine form. I even did a little twirl, watching the pleats of my skirt dance around my waist. And behind me, in the mirror, I saw my headmistress smile.
“How the other half live.” she observed.
She let her comment hang in the air for a moment, before turning and pulling the double doors open. I followed her back into the corridor, and soon we were walking past the vacant classrooms of the Old Building, it wasn’t long before we arrived at the foot of the old iron staircase.
“Carry on…” she prompted, “you may stop halfway up.”
I did as I was told, looking down through the lattice steps as she watched me. I knew what was expected of me, why she’d brought me here, so widened my stance so she could look up my skirt.
It was undeniably erotic. Not just the thrill of being dressed like this, but the pulse-quickening apprehension that someone I knew might appear at any moment at the top of the stairs. Then there was the soft hugging sensation of my knickers, and the cool draught whispering underneath my skirt, tickling my inner thighs. I could already feel my cock swelling painfully between my bottom cheeks, aching to spring free but being held in place by my tight white underwear. And beneath me, my headmistress silently watching me.
I don’t know how long I stood there on the stairs, but it was long enough for a realisation to begin to grow in my mind, one that I didn’t properly come to understand for several months afterward. It was the difference between the seedy and the erotic. The realisation that spying on others was just rude, a one-sided indulgence of gratification, an immature act of exploitation. Eroticism, on the other hand, was a far more fulfilling activity, it engaged the senses and aroused the mind, it involved willing participants. It was what grown-ups did.
Eventually she beckoned me down again with her finger.
“Now young lady, for your spanking.”
My blood ran cold hearing her announce my sentence so publicly. I could feel my palms growing clammy as we walked back in silence to her office. Towards my next appointment with her cane.
* * *
We’d only barely entered her office, but my headmistress didn’t stand on ceremony, sliding the lock on the door behind us, then striding determinedly to the wall to pluck the cane from its resting hooks.
“Well, young lady… it’s time to learn what happens to naughty girls.”
Her custom of addressing me as a schoolgirl made me squirm inside, but I did not demur. I hung up my blazer, and obediently took my place in the middle of the room.
I reached over, clasping my fingers behind my calves, feeling the hem of the skirt rise and drift up the back of my thighs. Moments later I felt her lift my skirt to the small of my back, tucking the hem into the waistband. I was expecting to feel her fingers in the elastic of my knickers next, the prelude to having them pulled down, but instead she tugged my underwear upwards, pulling the stretchy fabric up into my bum crack so the skin of my bottom cheeks was fully exposed.
“Naughty girls always get spanked on their bare bums.” she explained.
I took that to mean she’d usually tug their panties down, but in my case pulling my knickers tight helped confine my penis tight between my cheeks.
By now my mind was racing, hang on… I remember thinking, there wasn’t actually supposed to be any corporal punishment at this school. So who had my headmistress actually been spanking? Have a procession of naughty schoolgirls been paying secret visits to her office? Or were they being invited to visit her at home, to have their panties pulled down in the privacy of her living room?
Her cane began to tap against my bare cheeks, as if ascertaining my readiness. My ears registered the swoosh moments before the first whack seared across my bottom. I thanked her through clenched teeth and steeled myself for the next one.
Five more hard whacks followed, each carefully aimed so my bare cheeks took the force of each strike – yet close enough that I could feel each stroke graze the shaft of my swollen penis, trapped as it was between my bottom cheeks. The now familiar itchy sting burned hotter with every successive smack. Nevertheless, I thanked my headmistress earnestly and sincerely after my final whack.
Afterwards, I was sent to stand in the corner like naughty girls do, with my skirt tucked up, and my pink lines on display. Real girls however would surely have their knickers around their ankles, not pulled up tight, cruelly confining their excitement. By now my erection was making my position painful as well as humiliating; but also at the same time, intensely arousing.
Eventually I was recalled to stand in front of her, and she knelt by my waist to unbutton my skirt. She let the garment slip down to my ankles, and made me step out of it, before she folded it neatly and put it back on her desk.
“Let’s have a look at you…”
She ran her finger down the flat front of my underwear as if to emphasise my demasculation, then slowly tugged my knickers down to my ankles. Once released my erection sprang free dramatically, only just missing her face. I can’t remember ever being so hard. Her response was typically blaisé.
Her finger pointing the way, I was sent back to the corner immediately. I must have stood there for 10 minutes, my face burning as hot as my sore bum cheeks as I willed my cock to wilt. But that only seemed to make me harder. When she called me back, my priapism was obvious.
“Dear me…” she observed, “we can’t very well send you away like that. You’d better get undressed.”
I complied quickly, undoing my remaining garments and returning them reverentially to her desk until I stood naked in front of her again, my erection pointing at her accusingly and quite obscenely. Then, to my considerable surprise, she handed me two tissues.
“Back to the corner, young man, and relieve yourself…”
I was shocked by the bluntness of her instruction. Part of me wanted to object, to protest my innocence, to naively ask her what she meant. But attempt would have been preposterous; a teenage boy claiming he’d never masturbated. It was absurd, I knew I’d never be able to tell that lie to her.
So I returned to face the corner of the room, wrapping the tissues around the end of my cock with my right hand, my fingers grasping around the bulge of my helmet. With my other hand I reached behind me, trying to soothe the itchy, burning sting in my bottom.
“No rubbing!” called a voice behind me.
“Legs apart too, please. I always make my girls stand with their legs apart. It’s not just boys who get excited by a good hard spanking, you know. I bet you’d like to see that, wouldn’t you? A naughty girl’s vagina, her pink lips wet and swollen…”
Her words were like a magic spell, conjuring an image immediately into my febrile mind, one so vivid it quickly pushed me over the edge. I grasped my cock with both hands as I climaxed, feeling several hot spurts collect in my hand. I continued to pump myself, imagining a girl standing in the same spot as me, stroking her wet slit at her headmistress’s command. It was the best orgasm I could ever remember, and left me struggling to preserve some decorum, I had to stifle my gasps, I almost wobbled to my knees. And behind me I knew that Miss was watching everything.
After my glow subsided, I shuffled back to her desk, sheepishly placing my messy tissues in her wastepaper bin.
“Well. That didn’t take very long.” she observed, with what I suspected was a tone of disappointment in her voice.
“I think you might benefit from some lessons in self-control, young man. Lessons on a wide variety of subjects in fact.”
She passed me another couple of tissues to clean myself up, and then allowed me to get dressed in my own clothes again. Only then did she fix me with her eyes, speaking slowly and seriously.
“Your punishment is over. You may go home.”
Sometimes tiny decisions change the course of your life. Right then, I could easily have turned and scurried away, but something made me stand my ground, sensing she had more to say. And it was her who ultimately broke the tense silence.
“Hmm…” she said to herself, and then nodded, as if she’d just mentally answered her own question. Then she addressed me directly.
“I think you’d benefit from additional instruction. Something outside the normal curriculum. Lessons on becoming a real man. If you’re ready to learn, I have much I can teach.”
I held her gaze, but didn’t reply. I was too busy trying to understand what her words had meant. Did she mean sex? Losing my virginity? What else could becoming a man involve?
“If you’d like to become my student, visit my office at the same time next week, and we’ll begin your lessons. Or, if you’re happy to remain a boy, you may ignore what I’ve just said, go home when the bell rings and play with your toys.”
I didn’t know how to respond. But the automatic part of my mind answered for me, and I heard myself saying: “Thank you, Miss.”
And then, in a daze, I left without saying another word.
* * 3 * *
Over the week that followed I ruminated obsessively on the events of our last encounter, and especially her final cryptic offer. I replayed every word I could remember, looking for clues in what she’d said and how she’d punished me. Was it her intention to truly build me up or just to humiliate and demolish me completely?
Yes, our encounters had been excruciatingly embarrassing, but I’d experienced things I’d never have imagined. The night before, as I lay in bed in the dark, I finally realised I couldn’t prevaricate. I had to take up her offer, otherwise I was sure I’d spend the rest of my life trying to guess what might have been.
So when the Friday afternoon school bell rang, I let my classmates drift home and then crept furtively down the emerald corridor to her office. I knocked as loud as I dared, not even sure if I’d arrived too late. When I began to fear that she might already have gone home, I knew I was doing the right thing.
But then I heard her voice, calling me in. I gulped and turned the handle.
She smiled when she saw me. It wasn’t a sinister smile, or a mocking grin, I could see her face light up in friendly greeting, as if she was genuinely pleased to see me. I accepted her invitation and sat down on the sofa, and her offer of tea, and she sat in the armchair opposite, just like she had all those years ago.
We sipped our tea and started chatting, she asked me about my week, how my studies were progressing, what I was enjoying and what I hated. Our conversation was one-sided, I didn’t have the courage to cross-examine her, so she continued to ask the questions and I answered as best I could. Over time, the interrogation became more personal, she asked me the last time I cried, what upset me, my hopes and my fears. I knew she’d already seen a side of me no-one else had come close to seeing. She’d seen me naked, she’d seen me ejaculate, it felt pointless to try to conceal any more of my secrets. And with every additional question I could feel my mask falling further.
As time wore on, her questions became more intimate, and we began to talk about my sexuality. I apologised again for my silly intrusive transgression, hoping she’d understand it was motivated by immature curiosity rather than maliciousness. She did not absolve me, but merely nodded knowingly.
“How often do you masturabate?” she asked abruptly.
“Most… days” I croaked uncertainly, cloaking my answer in as much ambiguity as I thought I could get away with.
“And what do you imagine when playing?”
I had to think about that. It was unexpectedly difficult to explain. Just sexy things, really. An erotic montage of all the things that had ever turned me on. Glimpses of naked women, from holidays and movies. Scenes I’d read in books. Pictures of sunkissed naked models that might have been torn from porn mags, and were now secretly passed around amongst my friends like fragments of sacred scripture.
If that sounds archaic, I should explain. Whilst I did have a computer in my room, at the time my family home wasn’t connected to the internet. Few were back then. So I grew up without online porn. My head spins at the thought of how I would have turned out had I been given access to endless filth on demand.
“Er… naked women?” I replied uncertainly.
She didn’t challenge my answer, and rose from her chair, motioning to me to do the same, before strolling to the door, and locking it.
“Get undressed, please.” she told me.
I did as I was told without complaint, placing my shoes together and folding my uniform neatly beside where I was sitting. Then we swapped places, she took my place on the sofa and directed me to sit on the armchair, whose soft velvety velour felt wonderful against my bare bottom.
“Now, young man, show me how you masturbate.”
I almost blurted out a “What?!”, but her command was clear and unambiguous, it would have been rude to feign ignorance. So I reached down with my right hand and began to massage my cock, the act of undressing had meant I was swelling already, and it didn’t take much manipulation before I was fully erect in front of her. She watched in silence, like a naturalist observing sexual behaviour in the field, intrigued but dispassionate.
She never asked me what I was thinking of whilst I played, which was fortunate, as I might not have been able to tell her the truth. I was thinking of her, naked under her brilliant white blouse and elegant black skirt suit. I was imagining her suddenly standing, and undressing in front of me. I could feel myself getting close to coming, so I began to restrain my tugging, fearful of shooting my cream all over her.
“Good. Thank you. That’s enough I think.” she said at last.
I took my hand off myself, letting it rest beside my other hand on my lap. Meanwhile my headmistress had risen and gone to fetch something from her desk. She returned with a small sliver foil square.
My. Heart. Stopped.
Everything seemed to slow down for a moment. Around me the edges of the room blurred, as the tiny silvery package suddenly dominated my vision. I can remember feeling myself quivering, actually physically trembling. She immediately noticed my reaction.
“No, young man. We shall not be doing That.” she said firmly.
“I assume you’ve never worn one of these.” she added, clearly aware of my nervousness.
“Then you may consider this part of your sexual education.”
She passed me the featherlight foil packet and told me to open it. I remembered what I’d seen long ago in the sex ed films and tore from the serrated side, grateful to avoid struggling with the packaging like a total idiot. I teased the little rubber hat out with my fingers, it felt weird, surprisingly clammy and slimey.
I plonked it on the tip of my erection and padded the sides ineffectually with my fingertips as I tried to push it downwards. My teacher quickly intervened, telling me to pinch the top and roll down the rim. Of course. So obvious now, but back then I was a jumble of nerves with fumbling fingers. I rolled it down at my next attempt, which helped me feel just a little bit more grown-up.
As I was fiddling she retook her seat on the sofa, and then to my surprise pulled up the hem of her skirt to reveal the tops of her flesh-tone stockings. She unclipped the one on her right leg from her suspender belt, rolling the it down until it was a dark beige band just below her knee. Her beckoning finger indicated I should approach her, and then she pointed down towards her lap.
I did as I was told. She parted her legs slightly as I lunged over her lap, so my stiff penis ended up pointing down between her legs. Then she reached underneath me with her left hand, tugging the rolled-up band of her stocking away from her right leg so there was just enough room for my erection to slip inside. Then she squeezed her legs together so they held my shaft tightly in their soft nylon grip. I could feel the heat of her body against my erection. The sensation made my head spin.
“Well young man. You’ve already experienced the cane, but that’s for bad boys and girls. I’m going to show you how I discipline good boys and girls, to ensure they continue to live up to the high standards I expect.”
Whilst I was still pondering what she meant, she delivered a stinging spank with her palm to my bare bottom. I recoiled into her lap, pushing my erection deeper into the crevice between her thighs. It felt unexpectedly amazing, like wanking without using my hands, and it made me almost completely oblivious to the sting in my backside. I remember being surprised by loud I gasped.
“Ah. You like that?”
“Yes Miss! Thank you, Miss. May I have another?”
She obliged me, and I pumped between her thighs again.
“Now, I want you to be a good boy for me, and keep control of yourself whilst I give you a good long spanking.”
She continued to smack my bottom, slowly and steadily. Although I didn’t really understand what she meant about keeping control. To me, each spank just seemed like another perfect excuse to plunge between her thighs again. This must be what it’s like to have sex I realised, sliding your stiff cock in and out of a hot tight crevice.
It wasn’t long before I felt the familiar tingling surge of pleasure building at the base of my penis. Now I tried to restrain myself, to hold myself back each time she spanked me and not push down between her legs, but I’d already gone too far. I could feel the hot sting in my bottom seeping between my legs, the echoes of each smack lingering as tingles my balls, and the soft heat of her thighs eroding the last of my self-control.
“Oh Miss!” I pleaded, hoping for some respite.
But she just continued spanking me. I felt the tip of my cock throb, and moments later I knew I’d gone past the point of no return. Her next smack seemed to trigger my ejaculation, and I plunged myself between her thighs as I came, raising my hips and driving up and down repeatedly, milking myself, panting as I attempted to ride the wave of pleasure for as long as I possibly could.
“Naughty boy!“ she scolded, yet continuing to spank at her same steady pace.
I could feel my penis throbbing underneath me now, little spasms gradually ebbing away, and beneath me it felt wet, like I’d peed on her lap. I dearly hoped the condom hadn’t split, and I hadn’t spilled my stickiness down her leg. She seemed quite unconcerned though, and just continued spanking me.
It was an unwelcome surprise to discover that the aftermath of my climax had somehow made my bum acutely sensitive. Each strike of her palm now left a hot uncomfortable patch on my behind, despite her not seeming to smack any harder. Now I found each slap actually hurt, no longer the pleasurably warm tingle of before, but a succession of painfully sore stings. I felt like I’d suddenly regressed, going from virile lover to naughty little boy in a matter of minutes. I was squirming on her lap now, and had to clench my jaw to stop myself from whining like a silly little brat.
After what seemed an age, my spanking finally ceased, and she tugged at the band of her stocking to release my now floppy penis from her legs’ embrace. I rose awkwardly from her lap and stood utterly exposed in front of her, the sheath still intact and dangling, now heavy with the milky fluid it had collected. I reckon my bottom stung as fiercely as after my caning, but dignity demanded I control myself, and not reach back and rub myself childishly.
“Now roll down your condom and tie a knot at the bottom.” she said matter-of-factly, as if it was the most normal thing in the world.
I did as I was told, finding that the rubber was amazingly stretchy, and tying a knot in it was much easier than I’d expected. She directed me towards her desk and extended her hand, into which I placed my used condom, and in exchange she gave me a man-size tissue to wipe myself dry. As I cleaned myself up, she took out what looked like a little inkpad from her desk, but which actually turned out to be a small digital weighing scale.
“I think it’s time for some science.” she announced rhetorically.
I just looked back at her, baffled.
“I already know this brand of condom weighs exactly 2 grams… unused.” she added with a smile.
She placed the milky-coloured blob of rubber onto the scales, which changed its display to read 3.8. I realised that must mean I’d just spilled 1.8 grams of myself. Was that good?
“When did you last ejaculate?” she probed.
“Er… this morning, Miss.”
Fortunately she didn’t ask for details, that I’d wanked in bed after waking with an almost painfully stiff hard-on. I’d been thinking about my upcoming visit, of course. Imagining walking into her office to discover that behind her huge old oak desk, she wasn’t wearing anything below the waist. That the real reason she kept a cane on her wall was for guests to use, on her. I could still hear her voice in my head.
Oh please, she’d begged. I’ve been such a very naughty girl.
But she didn’t seem to react at all to my admission. She just nodded, and opened the little notebook on her desk, scribbling down the new data she’d collected in the manner of an eager field researcher.
“From now on, I shall be keeping a record of your visits.” she announced when she’d laid down her pen.
She fixed me with her basilisk stare, petrifying me where I stood.
“I expect you to be a good boy for me, and that means not masturbating without my permission.”
I just nodded, but my startled expression must have revealed I didn’t really understand what was expected of me.
“That means I expect to find more in your sheath next week.” she clarified.
Oh. Goodness. I felt a bit dizzy.
That could only mean two things:
And another session across her knee next Friday.
Another session of being spanked hard on my bare bottom by my strict, beautiful headmistress, until I climaxed shamelessly into her lap.
I got dressed as quickly as I could, feeling myself beginning to swell once more, hoping I’d be able to make it out the door before I got hard again.
* * *
I can almost see myself hurrying out of her office and down that long empty school corridor, watching myself like I’d been filmed on some secret camera. Isn’t it funny how the seminal moments of one’s life are preserved in such detail.
I realise I’ve stopped talking now. My mouth is dry. I can not see you, but I can still feel the heat of your crotch against my thighs. The tender softness of your labial lips, and the gooey wetness of your excitement.
From beyond my blindfold I hear your mellifluous voice.
“No! No! Don’t stop!”
I do love it when you plead.
And sorry darling, I’m afraid tugging at my cock isn’t going to get you your way, I’m not a vending machine. It seems that naive, callow boy learnt quite a bit about self-control under his strict hand of his Mistress.
“Tell me more! Please!”
I feel my mouth curve into a smile. You might currently hold me captive, but it seems my own story has captivated you. Only I know what you long to know, my dear, and my tale has only just begun.
So perhaps I should stop now, and tease you as you’ve teased me. And leave you aching with frustration, desperately trying to picture the possibilities, wondering just how my story ends.
Wouldn’t that be deliciously cruel…?
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