I hovered uncertainly outside the headmaster’s office. I’d knocked, but not heard an answer.
I was apprehensive - I’d only been in this job a month. It was my first since I’d qualified as a teacher. The school was imposing, with a lot of rules that seemed archaic compared to what I’d been led to expect from my training.
I’d been to a strict school myself as a child, but the discipline here was next-level.
It was a private boarding school, in the middle of nowhere. The pupils were all the problem children of fabulously wealthy families and this was basically a luxury reform school of last resort.
It was unusual, in that all the pupils were over 18. They’d all failed to finish school at any other institution, so they were with us until they could either improve their grades enough to go to university, or until their parents gave up and withdrew them.
In theory, they aged out at 21, but in practice, the school seldom housed them for more than a year. It had a sterling reputation for obedience and could usually turn around all but the least motivated of students.
So far, the pupils seemed ok, but some of them were only a couple of years younger than me and I struggled a little with that dynamic. Many of the pupils had the laconic confidence of the extremely wealthy that I sometimes found quite intimidating.
I thought I’d been doing a good job though, so I had been dismayed to be summoned to the headmaster’s office. I’d actually started trembling as I walked down the long path of flagstones that led from the quadrangle to his enclave. My footsteps sounded deafening as my heels clattered along the stones that had been worn smooth by many years of use.
The man terrified me. I’d met him twice - once in my final interview and once on my second day. Both times, I had felt hopelessly intimidated.
He made no concessions at all to 21st century schooling. He still wore black academic robes over his clothes, tweed trousers just visible, peeping out from beneath his gown and impeccably polished brogues. The pupils had to wear uniform. All teachers were referred to formally as “Miss -“ or “Mr -“.
The teaching staff was mostly male, similarly arcane and virtually all bachelors. The school was so remote that living on-site was really the only option. A handful of the housekeeping staff lived in the surrounding villages, but all the academic staff lived in the comfortable lodgings provided by the school.
I was yet to really get to know anyone well. I was at least two decades younger than any of the other teachers. Mr Chapel, the geography teacher, was always keen to chat, but from the way that he ogled my breasts, I suspected that his motives weren’t exactly pure.
A brisk “Come in!” interrupted my thoughts. Quickly tidying my already pristine appearance, smoothing my skirt and patting my hair, I finally entered the headmaster’s office for my audience with him. I felt the same stomach-churning anxiety that I used to feel as a pupil at my own school.
The headmaster was sitting behind his enormous mahogany desk and, without looking up, motioned to me that I should sit in the antique tall-backed leather armchair in front of him whilst he continued unhurriedly shuffling through some papers.
I perched myself gingerly in the chair, terrified of damaging anything. The room was opulent, large, and lined with vast shelves of books on every wall. A fire roared on the far side of the room, giving the office a stuffy feel. I felt myself starting to sweat, a rivulet running down my back, sticking to my blouse.
The headmaster made no effort to acknowledge me once I was seated and was now scribbling some notes in the margins of the pages in front of him, his Mont Blanc fountain pen spewing elegant dashes of blue ink as he wrote, frowning.
He was a handsome man, in an imposing way. He had apparently played rugby at university, I’d heard from somebody when I’d first started. He still had a massive frame, standing around 6 foot 4, with broad shoulders and huge hands and feet. He had to be in his 60s, but had a full head of thick grey hair that he wore severely, combed back from his forehead. He probably used Brylcreem, I smiled to myself.
“Something amusing you, Miss Fenwick?.
How had he done that? His eyes hadn’t left the papers in front of him.
He raised his head and I felt the full force of his cool, blue-eyed stare. It was the same way he had always looked at me, a combination of total disinterest but as though he could see all the way into my soul.
“Well, Miss Fenwick?”
I realised that I still hadn’t replied to his question. I stumbled out a response, which he received impassively, evidently bored of this entire encounter already.
He resumed writing for a few minutes, then capped his pen and stretched his fingers out at the knuckles, each of them cracking sharply. i jumped a little at the sudden violence of the movement.
“So, Miss Fenwick. How are you getting on here?”
“Um… Well, I think, Headmaster. Thank you.”
“Hmmm. Any issues in the classroom?”
“Oh, a few bumps along the way. You know. I think that’s normal at the start of a job…”
My voice petered out and I lost confidence under the weight of his steely stare.
“Miss Fenwick, I’ll get right to the point. I have become extremely concerned with some aspects of your comportment here.”
He moved a hand under his desk and must have flicked a switch of some description as a giant screen suddenly descended from the ceiling behind him.
Remote in hand, he clicked a couple of buttons and suddenly I was on the screen, in the classroom. A little counter at the bottom of the screen showed a date a couple of days beforehand. The image was disturbingly clear and high-resolution.
“Now, Miss Fenwick. Let’s look at a few things, shall we?”
Struck dumb, I nodded mutely. What on earth was happening? I had no idea that the lessons were being filmed, this had never been explained to me. My mind whirled, trying to work out where I might have failed.
Grabbing a pointer from behind his desk, the headmaster tapped at the screen.
“THIS, Miss Fenwick, is a pupil with a mobile phone on their desk. What is the school policy on cellular,” he elongated every syllable of this word, seemingly luxuriating in the sound, “phones, Miss Fenwick?”
“No mobile phones are permitted anywhere on school grounds during teaching hours, Headmaster, “ I parroted. This was one of many rules that had been drilled into me in my first week. “It was turned off though, Headmaster. I didn’t see the harm.”
This was the wrong thing to say. The headmaster exploded.
“The HARM, Miss Fenwick, is that the fabric of discipline in an INSTITUTION such as this is paper thin. The slightest infraction can lead to CHAOS. DO YOU UNDERSTAND ME, MISS FENWICK?”
He looked absolutely terrifying. Lips curled, eyes wild, even his hair was in danger of falling out of place.
“Yes, Headmaster. I’m so terribly sorry, Headmaster. It won’t happen again, Sir, I promise.”
Suddenly calmer again, he smoothed his hair back and fiddled with the remote once more.
“Sadly, Miss Fenwick, this is hardly the only example of your lax,” he spat this work out, “approach to school protocols.”
The video now showed one of the girls in my class loosening her tie. I winced. There were strict rules about compliance with uniform codes and this was, indeed, a violation. I hadn’t even noticed that this had happened. Shit.
“I’m so sorry, Headmaster. I will be more vigilant in future. I think it was a warm day, that day.”
His head snapped back to me from the screen. “Was it, Miss Fenwick. Was it a warm day that day?”
Confused, I nodded. “I believe so, Headmaster.”
He was furiously manipulating the remote, his mouth set in a grim line. Pausing the tape, he tapped the pointer so hard against the screen that I feared the glass might crack.
“In that case, Miss Fenwick, why the FUCK can I see your FUCKING NIPPLES here?”
Horrified, I watched as he slowly traced the stick around what was the very visible bump of my left nipple through my blouse. I couldn’t believe that the camera had picked this up. I’ve always had large, prominent nipples. The few lovers that I’ve had have either adored them or mocked them. I usually wear bras that they can’t show through, but I’d got my laundry days mixed up and now was confronted with the hard nub of my nipple, obscenely magnified on this giant screen.
Mortified, I tried to redeem myself. Whatever it took to get out of this humiliating situation. “I am so, so sorry Headmaster. This will never, ever happen again.”
“Miss Fenwick. I strongly suspect that you lack the MORAL FORTITUDE required for this type of work. You seem entirely unable to discipline your own body, let alone your students. I’m not sure that it’s entirely your fault. It’s your age. Your generation has, lamentably, lost their mettle.
I gave you a chance because Mr Chapel was very keen to get some younger blood around the place and he was quite taken with you. We agreed that he would be responsible for your supervision, on a more informal basis. So imagine my dismay when he delivered this to me earlier today.”
With a few manipulations of his thumb, the surroundings on the screen changed and it took me a few seconds for my brain to process what I was seeing. It was still me on screen, but, impossibly, the footage was from my bedroom, not the classroom.
“What… what is this, Headmaster?”
“This, Miss Fenwick, is one of a number of recordings that makes me question your moral fitness for this role.”
“But, that’s my bedroom. You have no right! How…”
The headmaster cut me off with a dismissive wave of his hand. Talking over me, he said icily, “The reputation and continued success of this school supersede any trifling questions of personal privacy, Miss Fenwick. It is imperative that we have only the most upstanding and dedicated teachers here, and it appears that you have failed utterly in this regard.”
Turning back to face the screen, he restarted the film and I watched in horror as I climbed into bed, quite naked. He had already passed the point at which I’d undressed, but I realised, aghast, that he must already have watched it. At least once.
The idea of him scrutinising my body with that contemptuous look of his appalled me and I felt myself start to sweat again. However, unavoidably, I also felt moisture starting to pool between my legs. There was something about his scornful detachment that I had always found inexplicably arousing and his large office suddenly seemed very small as we watched events unfold on screen.
After only a few moments in bed, the me on screen threw back the sheet. On my seat in in the study, I hung my head, unable to watch any more as the screen revealed my hand as it started to travel down my body, stroking my throat and slowly plucking at one of my nipples.
“Miss Fenwick, I must insist that you give this your fullest attention. How can you possibly repent for your transgressions if you aren’t willing to witness them?”
Miserably, I lifted my head, just in time to watch myself stretching that nipple taut, away from my body. My breast strained on-screen as I tugged slowly and lovingly at my own flesh, biting my lip, my thighs rubbing together in anticipation of ecstasy.
There was no sound on the video and the headmaster and I watched in silence for several minutes, as another version of me played with my nipples and stroked my breasts. The only sounds in the room were the occasional cracks from the fire and my intermittent gasps of humiliation as I reacted to the sight of me pleasuring myself on screen.
I wondered how much of this I would have to endure and was distraught to see my other hand on-screen, moving past the one that was still caressing my nipples and settling itself between my thighs.
The rest of this story is free for paid subscribers only.
If you’d like to read the rest, it’s available here.
More Headmaster stories here and here 💋🎓