Headmaster Punishment Bdsm Stories

61,534 results
Orientation
Length
Source
Infinite Scroll

A Very Shameful Punishment Ch. 04

by lesliejones on Sep 16, 2017
Fetish

For Meggs and Bill This story treats some matters that may offend some, so if you dislike reading about either menstruation or bodily functions of all kinds, this story is not for you. * Eleanor had been very relieved—no, overjoyed—when the District Court of the Women's Republic had released her from her punishment for the adulterous conduct in which she...

Suck My Big Tits Pt. 11

by breastysadie on Sep 18, 2017
Anal

I was in a world of trouble. We'd been back from our trip for less than a week when Daddy came home from work early and found Jamie and me twisted up in a dyke 69. Daddy was enraged that we'd dare fuck without his permission. He was always very generous with his permission, he reminded us, but permission was required. It's one of Daddy's strict house rules...

A Bunny to Play With Ch. 04

by ChrissieLecker on Sep 12, 2017
Novels and Novellas

* Author's Note: This chapter is one of fifteen in a novel. If you want to enjoy it fully, please start reading at the first chapter! * "Let's hit the road, Bunnie!" That war cry was so Anne, with her spontaneity and fable for the dramatic. For some unknown reason, I thought back to the moment the name 'Bunnie' had come about. It was actually a bit embarra...

A Game with Dice

by MALIBUMAN666 on Sep 13, 2017
BDSM

It all started when I suggested to my beautiful Mistress/Wife that she might like to extend her control over me beyond our monthly one-hour sessions. We've always kept our normal life and our femdom activities fairly separate, although Mistress does sometimes indulge me during the month by sitting on my face after I've come inside her and telling me to lick...

The Party Nun

by jonnicat on Sep 13, 2017
Erotic Couplings

Wearing the nun's outfit always gave Erica such a thrill ever since the time she had worn it to a fancy dress party in a country house hotel and used it to seduce a man dressed as a monk. She had arrived in a state of excitement (not unusual for her), her tiny panties hopelessly wet under the light imitation of a nun's robe, loving the feeling of walking in...

Jack's ex, Jack's slave Ch. 05

by AngryYoungMan on Sep 19, 2017
BDSM

Thank you all for the feedback. I should let you know this story takes much of it into consideration. I have never been in a relationship like the one I describe in my story, and had no idea about the motives and behaviours that are involved. Please let me know what you think of this story. Not much sex involved, more setup for the rest of the story as I hav...

How to Fix Your Editing Problem

by PDeanMurphy on Sep 12, 2017
BDSM

This is a copyrighted original work by the author. All rights reserved. All characters featured herein are at least eighteen years of age, even if not expressly stated. Any resemblance between actual persons, living or dead is entirely coincidental. Everything that happens in this story is consensual sex between a husband and wife. You may want to read My W...

Freya Takes Charge

by FreyasMaster on Sep 12, 2017
BDSM

Dedicated to my wife (Freya), who is my fantasy, and whom I love dearly. * Freya decided that she was hungry, hungry for her master's cock. It had been a week since she had tasted his thick white creamy fluid filling her mouth and it had been longer since he had unlocked her chastity belt and fucked her raw in her holes that she so lovingly keep hairless...

A Billionaire's Son: The Escort

by playfulsin on Feb 7, 2018
BDSM

She came over to where I was sitting. She was a beautiful young blond girl of no more than 19. As she approached I could see she had blue eyes under eyelashes that were obviously enhanced with makeup. When she closed her eyes you could see the dark green eye liner she used, and it only enhanced the feeling that she was very young, perhaps younger than the es...

Arranged Marriage Ch. 01

by indsub89 on Mar 26, 2019
Exhibitionist & Voyeur

Arranged marriage! Arranged. Marriage. A combination of two words that was completely alien to anyone who was not born and brought up in India. However, in India, it was the norm even in 2019. Well, maybe not "the norm". Love marriages were becoming more and more commonplace in India too, but it was a far smaller number in comparison to arranged marriages. T...