Headmaster Punishment Bdsm Stories

61,534 results
Orientation
Length
Source
Infinite Scroll

Arcadia Castle Ch. 01

by Hal1031 on Jan 8, 2018
BDSM

Chapter 1: THE HEADMASTER The taxi driver checked his odometer, sighed, and cranked the A/C as high as the knob would go. The desert was especially unforgiving this time of year. Sweat trickled down my neck and rolled inside the paper-thin, white tank top they'd so generously provided for my trip. No bra, no panties allowed. Just the tank, a pair of cheeky...

Bad Girl Ch. 1

by anneski on Sep 14, 2017
BDSM

She stood with head bowed in front of the Headmaster's desk, flanked by the head girl and her crony of a deputy. Her heart was pounding and she was very scared indeed. Anya had only been at this institution for a short time, but already she was finding that the discipline was like no other she had come across. She had heard of canings, and rumours of more,...

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...

Schooling Ch. 02

by VGracen on Sep 12, 2017
BDSM

The darkly paneled hallway to the Headmaster's office seemed to grow longer with each step she took that day. Her body moved obediently, never betraying the war going on in her head. "What he is doing to me is abuse! I should report this to somebody, I should just tell him NO! He doesn't have any right to touch me that way or tell me what to do"! Her hand...

Finishing School Handbook

by brewster926 on Sep 16, 2017
Humor & Satire

Please note: this is an official copy of the handbook actually used at Dr. Deucel's famous finishing school which was in existence in Wayward on the Tool in Lower Suckexx during the latter part of the Nineteenth Century. Dr. Deucel's school was known for taking ladies in their twenties and older that everyone else had given up on and helping them become happ...

Morgana's Painful Lesson Ch. 2

by Morganauk on Sep 16, 2017
BDSM

It was Friday afternoon and the last day of the school year. There was an expectant buzz in the air, as everyone's thoughts were concentrated on tonight's leaving party. Morgana was as excited as everyone else – she had big plans for tonight. Headmaster Dave had kindly agreed to hold the yearly event in his large country house. Only the older pupils were in...

The Party's Ripe for Caning Ch. 03

by lesliejones on Sep 19, 2017
BDSM

[This story takes place in a prep school which prepares pupils for three years after high school for university, from ages 18-20. Previous chapters explored Miss Crawford's introduction to the strict disciplinary regimen as the first female teacher of the boys' school.] Linda Crawford now had completed her second full year as an English teacher at Hamilto...

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...

The Program Ch. 01-06

by IdeeFixee on Sep 19, 2017
BDSM

Chapter 1: How the Program works - exam, selection, installation, observation and accessories The Headmaster of exclusive Ansonia Academy was sitting by the fireplace in the Faculty Lounge with his younger colleague from a sister prep school in New England. They were drinking sherry at tea time, alone. In his mid-forties, the Headmaster was wiry, with stiff...

St. Mary's 6th Form Sluts Ch. 17

by Celtic_Heart on Sep 14, 2017
Novels and Novellas

Shona and Jane sat nervously outside Mr. Beattie's office. Inside, the Battle-axe, Miss Carlisle was appraising the headmaster of the girls' latest misdemeanour. "What's the bets she tries to have us expelled again?" Shona asked her blonde friend. "Mr. Beattie won't do that, not with the exams starting next week," Jane replied. "The Battle-axe is sure to...