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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...

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...

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...

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 f...

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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...

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 enve...

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 wh...

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,...

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 t...