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Headmaster Stories

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Justina's Accusation (YNAS) - Pt. 12

The headmaster is caught having broken several disciplinary rules in his dealings with Justina!

12 - Accusations It took enormous restraint to resist opening the envelope the night before, but I did manage to wait till the following morning. Certain that nothing would be happening before tonight, or likely even this weekend, I didn’t feel in a hurry to open it, but for no other reason than my curiosity getting the better of me, I made my morning cup of tea, sat at the kitchen table, and opened it. Inside was another...

It's the end of my senior year, just weeks until graduation, and seeing that most of my work is finished, I've been finding it hard to care. I've been rolling into class late a lot, sometimes not bothering to show up at all. I had a feeling it'd catch up to me eventually, so I just roll my eyes and shake my head when I get called into your office. I stride down the empty hallway toward the office, where your matronly secr...

Friday Morning, Panties Down

Just another visit to the Headmaster's office

Another Friday morning, outside your office, This is my fifth time, so I'm hardly a novice Same old infringement, my skirt is too short, I should know better, I really ought 🍆 The Head Master they said, it's that or detention, It was an easy choice. I love the attention Though English is my subject, I'm not fond of inflection, Now I'm standing before you, awaiting inspection 🍆 'Touch your toes', you say just for your pl...

Headmasters Rules

Mr Evans knew the job would be challenging and he relished it.

Mr Dafydd Evans thumbed through the report on his desk. Five pages of misbehaving from two young girls both aged sixteen and born just one week apart; both of them just three weeks away from their seventeenth birthday. The reports were from Mr Gregory who taught Mathematics, Mr James who taught Geography and the worse report from Miss Thornton who taught Religious Instruction. It wasn’t a one-off. This report landed on hi...

Carla Meets Mister Theobald

Crossdresser dresses as a schoolgirl for a meeting with a headmaster and is dealt with appropriately

Karl Baxter was an unmarried man aged forty who spent a lot of his time as attractive thirty-something Carla Baker. Throughout his twenties and early thirties, Karl had had sexual liaisons with both females and males but if he were to express a preference at that time it would have been for cock rather than cunt. At about the age of thirty-five, Karl had started to dress, from time to time, as a female although in the ear...

The Headmaster

A fantasy about my sixteen-yearold school days.

To say that Mr. Lavender and I didn’t hit it off would be something of an understatement. In this strict all-male environment us boys were referred to by surname and teachers as “Sir”; we stood when they entered the room and sat when we were given permission. Having just turned sixteen I’d frankly had enough and while I still attended classes a paid no heed to the maths lesson or the homework; I had better things to do wh...

Last Wills and Testaments - Two

Kim's caning is repeatedly interrupted by the headmaster's secretary and phone calls

Preston and his wife Gail sat fidgeting in front of the massive desk of Janet Johnson, Attorney at Law.  Would the woman stop with the small talk and get down to business.  To the business of reading the Last Will and Testament of Preston’s now-deceased father, Irwin T. Lakehurst Jr.?  Finally she got down to the nitty gritty. “I appoint my faithful attorney Janet Johnson, Esq. to be Executrix of this my Last Will and Tes...

My Headmaster, My Master

Naughty schoolgirl gets spanked

Once again, Holly walked down the school corridor, she was being sent to the headmaster’s office. This time it wasn’t even her fault, one of the other girls had thrown the paper airplane. She always got the blame. She walked past the toilets and decided it would be better to hide out in there. Sneaking in, she looked at herself in the mirror. Holly was a cute seventeen-year-old girl with dirty blond hair and blue eyes. Sh...

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Lexie's Adventures

Lexie is a wild girl who get's sent to a boarding school for girls

This is the story about when my parents sent me to a boarding school. My name is Lexie and I'm an eighteen year old girl. I have long blonde hair that I always wear in a ponytail. I've been told that I have blue piercing eyes. I'm five foot five, and weigh one hundred pounds. I've been blessed with large breasts. I am a 38 C cup size. I also have a shaved pussy. I've been a real handful for my parents. I've been getting i...

St Mary's - Part One

The secretive school for boys

Alexander James paced the corridor outside the headmaster's office, waiting to be seen. It was an ashen-faced Mr. Norris, his form teacher, who'd silently passed the meeting note to him in class that said Mr. Hampton wanted to see him.St. Mary's was unique among English all-boys sixth forms in its selection process. All young men must be, as well as hard workers, in the very best physical condition. As well as an entrance...

Headmaster's Revenge - Chapter Two

Her punishment continues as she learns her lesson about good timekeeping.

Shooting pains seared down my arms right from the shoulders, down to where the cheap polyester tie still bound my wrists together behind my back. One side of my face was pressed to the cold floor and I could feel his cum drying and flaking on the exposed side of my face.He was sat in his chair; head tilted back, leaning on the wall behind him with a look of utter bliss on his face. I pulled my legs closer to my chest, too...

Headmaster's Revenge - Chapter One

She thought he would forget, little did she know...

The day the letter dropped onto the doormat and I caught a glimpse of my old school crest a flood of emotions and memories hit me. Bending down to pick it up I swept the hair from my face and let out a big sigh. Trudging back to the kitchen I put the envelope by the kettle as I started to make a coffee. I lit a cigarette, inhaling deeply as I tore open the envelope and began to speed read through the letter. My shoulders...

Please Sir

Rachel never followed school rules

It had been a normal day in school when the Headmaster had summoned me too this office that afternoon and thats when the nerves set in. Girls had been called into his office before at random and came out different, they came out and refused to speak of what happened. Rumors spread that he was using the cane on girls to keep them in line during his uniform check and if he found anything wrong it was a swift thwack with the...

Soft Target: The Head's punishment

When Chrissie had to see her son's headteacher he got more than he bargained for.

Chrissie sat outside the head teacher’s office, shifting nervously. Even though she was now a parent, with a son at the school, the old memories still made her shiver. She could still remember standing outside the headmaster’s office, all those years ago, biting her lip in anticipation of the yet another harsh telling off about the latest indiscretion. But now she was here discuss her son’s behaviour. Mark was a typical t...

I am just coming to the end of a very successful teaching career. I am respected within my profession and often newly qualified teachers ask me for advice. My response is always the same “maintain classroom discipline.” Until now I haven’t elaborated on this response however I think it is time to reveal how I learned this very important lesson. I had just qualified as a teacher and having undertaken a probationary period...