Busty Tease And Boarding School Headmaster Stories Stories

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FemSub Boarding School For Girls

by JustForFun5676 on Apr 22, 2025

A long time ago in a galaxy far far away.... Blond girl Emily was nervous; as she felt that the chastity belt that had been placed between her legs by the boarding school officials was too tight. She also felt that the uniform was too short. At first she thought it would be strange, but after seeing how other girls were dressed in the academy, she realized t...

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Boarding School - Introduction

by pr0nnage on Sep 13, 2017
Non-Erotic

All characters in this series are fictitious, as are the encounters between characters. The boarding school is at the high-school level, and all characters involved in the stories are over the age of 18. A disclaimer will be placed at the beginning of each part, with categories that the story fits into -- so that, if it's something you're not into, you know...

Mercedes Senior Year at St. Vincent

by OTKTop on Sep 17, 2017
BDSM

Mercedes senior year at St. Vincent Boarding school ***** When she was younger, Mercedes went to a very strict boarding school, one that still allowed corporal punishment. Usually the punishment was used sparingly but with a new Headmaster, Dr. Hoffman, more and more of the young women of St. Vincent Boarding School were ending up in the Headmaster's offic...

Scottish Boarding School Ch. 01

by HollyRed on Sep 13, 2017
BDSM

It was a shock to be packed off to boarding school- especially at the age of eighteen. I thought my school days were over but due to a very damming report card I was not free just yet. I had enjoyed the last two years of my A'levels a bit too much. Party followed party and my results showed this. I may have learnt how to tease a man's cock up to greet me but...

Mary Carson's Punishment

by Lissette on Sep 17, 2017
BDSM

Mary Carson walked slowly down the empty halls of the girls' boarding school she attended. Most of the students had already returned to the dormitory for the evening to enjoy their evening meal and to complete their nightly homework. Mary, however, was headed to Headmaster Finch's office and she had a pretty good idea why. The Hutchens School for girls was...

Cane and Cock

by AnnGoode on Sep 17, 2017
BDSM

Lady Dawn was born into a family of wealth and influence. One of the families that had three centuries ago formed a secret society to preserve their status. Only male members of the families could join. In the year 1703 they set out the principles by which they and future generations would continue to prosper. Today those same families having endured wars an...

School Daze

by Croony on Dec 29, 2017
Fetish

Abbottsford College, situated in the City of London, was a prestigious all boys finishing school that catered for teenagers from the age of sixteen to eighteen. The pupils were mainly from rich and titled families who wanted their sons to experience the strict regime and make them into better adults. David Bryden was the headmaster that dealt with disciplin...

Geneva School for Girls Ch. 01

by rmdexter on Jul 9, 2019
Mature

PROLOGUE The Geneva School for Girls is a two-year finishing school for 18- and 19-year-old ladies just graduated from high school. These are girls who are mostly from wealthy families, who don't blink at the six-figure-a-year tuition and room and board (with a smattering of scholarship girls thrown into the mix). The school was founded by Headmaster Jake...

Finishing School For Ladies Ch. 01

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One -- The Beginning Valerie Swindon sat at her desk in her small study grading exam papers. A shadow fell over the opaque glass panel of the door and she looked up at the ornate mantle clock and realised it was time. She arose from her chair and came around to the front of her cluttered desk and unzipped her skirt. She caught it before it pooled...

A Headmaster's Lesson Pt. 01

by LittleKay on Nov 6, 2018
Fetish

Greetings! Thanks for taking the time to read my story. Feedback and Comments are welcome! Please read the disclaimers at the end before leaving negative comments on the themes or content. This *is* a dark, twisted story. Apologies in advance. _________________ The only thing worse than growing up in a wealthy religious family was being sent to boarding...