Headmaster Punishment Stories

31,842 results
Orientation
Length
Source
Infinite Scroll

Sexslave Acadamy

by daphneamber377 on Sep 12, 2017
Novels and Novellas

-This is a story set in a future dystopian society, a society in which there are way more women than men. The first few chapters basically builds a backstory. If you don't want to be confused later on about different things, please read patiently. Keep in mind that no one in the Academy, both male and female, is below the age of 18. Any younger children ment...

View From a Window Ch. 04

by Drmaxc on Sep 28, 2020
Exhibitionist & Voyeur

Three people in a car, travelling down little sun-drenched roads in search of a local beach. Graeme driving with Jill beside him and Mandy in the back. The air-conditioning on. "You all right there in the back, not too hot?" A day for the beach rather than sightseeing. The villa had a swimming pool so the sea was not essential for a cooling dip and they di...

The Headmaster

by PaulieCelt on Mar 11, 2019
BDSM

Fiona sat in her car for long moments, her head leaning toward the open window and exhaling puffs of smoke as she readied herself for the situation ahead of her. She glanced back and forth at the little gold-bracelet style watch on her wrist, shaking her head, and sighing through her nostrils each time. As her lips wrapped around the butt for the last time...

My Friend Sophie Ch. 02

by LeanneSinclair on Sep 17, 2017
BDSM

In the previous story I introduced you to my lovely friend Sophie and told you about an evening when she and I got very drunk and she told me, in great and explicit detail, about her submissive fantasies and desires, which were focused on her male boss. I'll pick up the story again on the morning after that, briefly, although I'll probably then gloss over so...

Painful School Reunion

by djt_one on Sep 19, 2017
BDSM

It had been over 6 months since John and Sue had first been introduced to the painful pleasures of caning by the fraudulent Dr Hay. Whilst they realised that his methods would not help their chances of conceiving their first child, they had found another dimension to their sex life. John very much enjoyed caning his wife, and Sue enjoyed the sex afterwards!...

A Costume for Every Trick

by Bethyboo on Aug 31, 2017
Group Sex

There's a brisk rain falling, I can hear it hitting the window pane, tappity tap. The accompanying wind is stripping the leaves from the trees creating a colorful carpet on the ground. A lazy stretch as I realize my bladder is done lying in bed, warm feet hit the cold floor and with a full body shiver I hurry to the bathroom. Just before the flush of the toi...

Alice Ch. 01

by Daddys_Touch on Sep 14, 2017
BDSM

Alice is an 18 year old girl studying at a 6th form college which is part of an all-girls boarding school. This story contains scenes of sex, violence and gunplay. If you are not comfortable with this: do not read on. * Alice left registration, pushing open the door that lead outside and turned in the direction of her English class. She heard someone calli...

Reunion

by LaurelAspen on Jul 4, 2018
BDSM

Penny's footsteps echo down the long corridor, early evening sunlight filters through windows set with leaded glass, splashing rainbow colours onto plain stark walls. Penny, more properly Penelope, stops for a moment; a knot of anxiety twists in her stomach, apprehension lines her face. Pushing back her shoulders resolutely she continues, carefully checking...

Service Provider Ch. 01-13

by IdeeFixee on Sep 19, 2017
BDSM

Part 2 — Service Provider Before beginning, please read Part 1: Mother's Helper, The Black Diary. In Part 1, Janice, a hot and sexually frustrated single MILF, is riddled with guilt over her poor parenting of her hot son Matthew, a high school senior. Matt discovers his voluptuous mother's unquenchable penchant for sex and punishment, and quickly increases...

The Headmaster's Room Ch. 02

by Mag58 on Sep 12, 2017
Fetish

When the bell rang for the end of the morning lessons at 12.30; I was strangely disappointed at not having been called back to Mr Skinners' office for him to finish my punishment in his study. I ate lunch with some girlfriends then hung around the gym buildings smoking cigarettes and talking about a party that we were going to on the Saturday night. As the b...