Headmaster Stories

774 results
Orientation
Length
Source
Infinite Scroll

Morgana's Painful Lesson

by Morganauk on Sep 16, 2017
BDSM

Morgana stood outside the Headmaster's office, nervously holding the note in her hand. She didn't know the contents of the note, only that it was about her and that she was in some sort of trouble. At 18 years old she already had a woman's figure and somehow looked out of place wearing the compulsory school uniform. She was short with blonde hair and blue...

Six of the Best Ch. 02

by KinoKe on Sep 17, 2017
BDSM

It was a little after seven in the evening. The Headmaster was in his study, hunting and pecking at the keyboard that sat atop his large oak desk with its dark forest green inlaid leather top. Tap, tap, tap. Tap, tap, tap. And then, from the door opposite, almost an echo: Tap, tap, tap. 'Come!' The Headmaster called. The study door opened and Matron -- fif...

Detention Pt. 02

by Croony on Sep 15, 2017
Fetish

Susie Johnson had a sip of her chilled white wine as she got ready for a night out with a couple of her friends. She'd finished her make up and had chosen her sexiest black underwear with black hold up stockings. She had decided to wear her favourite little black dress. She remembered the last time she wore it. She would never forget the day when she was rav...

New Punishment System Demonstration

by TUnicornLiterotica on Jun 15, 2020
Transgender & Crossdressers

DISCLAIMER: This story involves the degradation of a trans character, this is not meant to be read as transphobic scripture. The writer, being me, is trans, not that makes it automatically okay, but just understand, this is a fantasy, and it fulfills some of my submissive desires. Characters all 18 years old above etc. * * * * * Carla had just been pulled...

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...

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...

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...

The School Prize Giving

by Mrzxcvb on Sep 13, 2017
Exhibitionist & Voyeur

I'm running a little late for the school prize giving ceremony. My nephew is singing in the school choir as part of the entertainment. The event is to be held in the school grounds on a glorious summer's day with blue skies and just a gentle breeze to keep the temperature to a bearable level. As I approach the seating area with a minute or so to spare I no...

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...

Telling Tales of Sunny and James Ch. 01

by Redgrenadine on Dec 11, 2018
Erotic Couplings

They met two years before, on the other side of the world. Tonight, Sunny and James both thought with bittersweet regret about how they got here - a third floor officetel on the outskirts of Seoul - Sunny, on the tiny kitchen hallway floor, wiped tears from her tightly closed eyes with a corner of her blanket, while James rested with one eye open, on his bed...