Headmaster Punishment Stories

31,842 results
Orientation
Length
Source
Infinite Scroll

Plain Jane Ch. 09

by KaereniSister on Jan 15, 2018
Novels and Novellas

This story is copyrighted 2008, revised 2016 by Kaereni, may not be excerpted, reprinted, reproduced, or reposted in any form without the express written consent of the author. Visitors to this web site may read or temporarily download pages but are not permitted to modify or re-distribute them. The story may contain sexual activities and situations that ar...

Pledge Initiation

by professorjames on Dec 12, 2018
BDSM

Michael carried his tray into the student union and looked around for a place to sit. Thursday night it wasn't particularly crowded but off in the right corner he noticed a table with five distinctively attractive females and immediately decided his dinner view would be much improved if he settled where he could watch them. He spotted an empty table against...

Ann: The Married Years Ch. 21

by mimaster on Jun 11, 2019
BDSM

© 2019, All rights reserved -- mimaster ~*~*~*~*~*~*~ Ann could feel something tugging at her neck but she didn't understand, at least at first. Opening her eyes, she was startled by her surroundings. Everything seemed shaded in a deep blue, like she was wearing a pair of tinted sunglasses. Her pupils were having trouble adjusting. "Where am I?" she whisp...

A Taste of Slavery Ch. 53

by Thors_Fist on Apr 6, 2020
Novels and Novellas

This chapter has our three slaves joining their Master in LA. His behavior continues to befuddle them. What is he trying to do? This chapter contains, oral, lesbian, interracial sex and lots of fucking with multiple partners. Scott finally explains himself. Like every other chapter in this series, Sexually Transmitted Disease doesn't exist and unprotected se...

Sam Spade 07: Case of the Wayward Sister

by KaereniSister on Sep 19, 2017
Novels and Novellas

This story is copyrighted 2006 by Kaereni, may not be excerpted, reprinted, reproduced, or reposted in any form without the express written consent of the author. Visitors to this web site may read or temporarily download pages but are not permitted to modify or re-distribute them. The story contains sexual activities and situations that are to be read only...

Charlie and Megan Wilson

by BroderickWinston on Sep 17, 2017
BDSM

"Who's that," I said, as we walked down the hall. "Her? You can't afford her," said Marissa. "Besides you've got a date with a switch. So, let's try to focus shall we?" she said. "Yes, yes of course ma'am," I said. For the price of $100 an hour, once a month for the past year, I had had the extreme pleasure of having my hide tanned real good by Marissa. In...

A Cup of Tea Bk. 03

by soppingwetpanties on Aug 13, 2019
BDSM

This is the final installment of a three part series. It's recommended, though not essential, that you read the first two installments. There's a ton of sex in this installment as we watch Dax's submissive tendencies get the better of him. Enjoy! This is a work of fiction. Names, characters, businesses, places, merchandise, companies, events and incidents...

My Workmate Julia

by sadbluekid on Jun 8, 2020
BDSM

This story was initially inspired by jack562004's series 'Femdom between friends'. I read these stories and found them exciting and hot. There are some similarities, but quite a few differences. This story, I think, is gentler as it goes. I hope you enjoy and welcome comments, particularly from those willing to put their names to them. If femdom isn't your t...

The Good Kingdom

by fmcchris on Sep 12, 2017
Exhibitionist & Voyeur

My name is Francesca Karin Aadland Romanetti and I am the leader of the people of the "Good Kingdom," the mountain valley paradise that is known to the native Tibetans as Swarga Loka, which is its Sanskrit name. My family of sisters and I live on the highest mountain in Tibet, called the Shishma Pangma, where the colossal Himalayan Mountains form a border be...

The Old House

by l_anonym on Jan 22, 2019
BDSM

Prologue This story is about a group of young people living together in a big old house a bit outside of town. Most of them are students so they enjoy the rather cheap rent and the somewhat secluded place where they can party anytime without having to worry about the neighbours. Don't get me wrong: It's not a place with a nonstop party -- they all have to...