Headmaster Punishment Stories

31,842 results
Orientation
Length
Source
Infinite Scroll

Sexual Institution Ch. 02

by NudeDreams on Sep 11, 2017
Fetish

~Everyone in the following is over the age of 18~ ~Thanks to everyone for the positive feedback! It's very much appreciated from a new writer like myself!~ Maddie and Bailey's punishment had yet to be decided on, and the former had spent the entirety of the next day worrying about how dreadful it would be. During her Discovering Fetishes class, she drifted...

Sean Leaves Karen

by jacksgirl on Sep 17, 2017
BDSM

There was going to be a party. Sean invited several friends and business associates. He told us to be prepared for twenty guests. Jillian and I cleaned and cooked for days. Well, ok, Jillian did most of the cleaning. Since I am an excellent cook, the kitchen was my domain. And I loved it. Of course, Sean insisted Jillian and I remain naked at all times. Whic...

The Head Master and the Panties

by Misslexia on Aug 29, 2017
Fetish

Marion was beginning to wish her best friend Caitlin hadn't persuaded her to sneak back into school with her to retrieve her purse. The two 18 year-old sixth-formers were best friends. Marion was Head Girl and Caitlin was Sports Captain, yet as they stood by the sign reading 'Staff Only -- Entry to all pupils forbidden' that stood on the gate to the courtyar...

Schooling

by VGracen on Sep 12, 2017
BDSM

She sat angrily in the hard chair outside the office, glaring at the two aides who had apparently been assigned to watch her. “SO WHAT if I tried to run away last night...! I didn’t ASK to be sent to this STUPID school. It’s not my FAULT that my mother died and that my stepfather “just can’t handle me” any more! SO WHAT if the drinking and drugs and parties...

Lucia Gets Spanked

by jennanips on Sep 12, 2017
BDSM

*This story is a work of fiction. All resemblances to any person are purely coincidental. All rights reserved by author.* * Lucia was really hoping this was going to work. She looked herself over in the mirror. Although Lucia was in her mid-thirties, she looked much younger, especially in the schoolgirl outfit she had donned. The top was a white button-do...

Not Naked in School

by bradley_stoke on Sep 16, 2017
Exhibitionist & Voyeur

Wendy felt so embarrassed as she stood waiting for the school bus, with her fellow school students at the bus stop. Her hair was tied in plaits, her skirt came to just below her knees, a blazer and blouse covered her from the pit of her throat to her waist, and long white socks from her ankles to her knees. And worse, if that wasn't bad enough, beneath these...

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...

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...

Pakistani Daughter

by StoryTeller07 on Feb 6, 2018
Fetish

A daughter takes over Ayesha was shopping locally with her mother, getting to know the new area. She hoped not to run into anyone from the new school while wearing traditional Pakistani clothes. Although, while wearing an abbaya and head scarf, there wasn't much chance she would be recognised. The clothing completely covered her, leaving just her face parti...

Another Year at St Cat’s Ch. 05

by nightvoice2 on Sep 25, 2017
Novels and Novellas

Reality Stings ------------------ Wednesday, 9 April ------------------ It was the kind of bright, airy spring day that felt warm when you were in the sunshine, but made you shiver if you were caught in the shadows, the cold, northerly breeze nipping at your ears and nose. Along the path that led down to the river the cherry trees were in full blossom lo...