Headmaster Punishment Bdsm Stories

61,534 results
Orientation
Length
Source
Infinite Scroll

The Last Sashay

by mDyne on Sep 15, 2017
BDSM

Chapter 1. Mr. Punire "Good to see you again Mr. Punire. Has it been two years already?" "Two years less a day, according to my calendar. Schools I always do Fridays, and for an old customer like you, always the Friday before spring break." "Still doing a lot of traveling?" "Not so much any more; there aren't too many places where I can learn something t...

Downtime at the Office

by Finansol on Aug 30, 2017
Erotic Couplings

Marissa had some downtime at work and was surfing the Internet trying to find a site to help with sales leads when she noticed that her email had a new message waiting. She checked the inbox and discovered that a friend of hers had sent her a link to an erotic story site. She smiled. It had been a while since she'd had the time to flip through such a site an...

The Headmaster and the Pupil

by irisheyesgirl on Sep 12, 2017
BDSM

The characters in this story are consenting adults. St. Ann's School exists in the imagination of two creative lovers. If you enjoyed reading these characters as much as I enjoyed writing them, please leave suggestions for what you'd like to see them up to next! ***** -The Headmaster- "WHAT am I going to do with you, Miss Connolly?" I sighed heavily as I...

Heather & Mrs. Harley Ch. 02

by UBU on Sep 14, 2017
BDSM

When I got up the next morning it all seemed unreal, as if what had happened with Mrs. Harley the night before really had been just a nightmare. I couldn’t quite convince myself of it though, and distractedly sleepwalked through my first day of senior year, avoiding Heather and only seeing Mrs. Harley from a distance, as she swept into her classroom with a q...

Little Miss Perfect & The Headmaster

by bbwsweetstuff on Sep 25, 2017
BDSM

Outside the heavy walnut door, Serena stood twisting the edge of her plaid skirt nervously in her fingers. Biting her bottom lip, her mind raced trying to fathom what was about to happen to her and if there was anything that should could say or do to get herself out of it. At 18 years old, she was an abnormally good girl. She had fabulous grades while atte...

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...

Alex Ch. 03

by HappilyM on Sep 19, 2017
Romance

If you are reading this in hopes for a stroke story, I am sorry to disappoint you. There is very little sexual interaction and a lot of plot development that will make the subsequent chapters flow. * The next morning I awoke in absolute pain. I could not find Alex. I grabbed the crutches and hobbled to the dresser. I pulled on an aqua-colored tee-shit. I...

Journey of Submission Pt. 02

by msterrilynn on Sep 17, 2017
BDSM

Chapter1 He had been watching her move through the lessons of the Academy, a school of submission. She moved with a quiet grace, a sparkle of joy in her eye as she performed her tasks. While watching her, He was reminded of the fawn that she had been named for during early training. Often near the top of her class, she was still unsure of herself but persev...

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...