Headmistress Spanking Stories

23,089 results
Orientation
Length
Source
Infinite Scroll

A Sissy Saga Ch. 04

by Snurge on Sep 15, 2017
Novels and Novellas

The highly polished writing table was uncluttered, the only item encroaching its pristine surface being the letter of application Miriam Hancock had received from Emma Twist, the young woman who now sat stiff backed in the chair facing her. Miss Hancock folded her hands over the pieces of paper and gave the impression of ignoring them as she assessed the ca...

Anne Virginia's First Halloween

by Longgfellow on Oct 8, 2019
Erotic Horror

This story contains elements of erotic horror, non-human (shapeshifter) sex, BDSM, virgin, and reluctant sex... eventually. All characters in the story are 18 years old, or older. Each chapter ends with a "bang", with a grand finale at the end... Note 1: This is a Halloween 2019 Contest story. Please upvote if you like it, and would like to see more! Note...

Too Many Spanking E-mails!

by glencane on Jan 7, 2018
BDSM

Rob had many fantasies all to do with spanking and caning. He scoured the internet for mature dominant Mistresses, anyone who offered exciting times in their well equipped premises. He had recieved many replies, quite diverse replies at times, as some had dungeons, others soundproof cellars and attic playrooms. Their roles were varied as some were rubber and...

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SSCG Ch. 01-02

by Crystal_Ash on Sep 11, 2017
BDSM

Chapter 1 - Arrival St Sayd's College is a very exclusive college for girls. Its pupils generally do very well in their academics, their sport and cultural activities. It is also very exclusive, for good reason, since its teaching methods are rather unorthodox. This is the story of Jennifer Smith, a tall, slender brunette with brown eyes and a nice figure,...

The Girls College Ch. 03

by TF2123 on Sep 25, 2017
Fetish

While aimlessly wandering around the front of the Jane Marwood Hall, Paul was approached from behind by a short, thin girl with jet black hair and her taller brunette acquaintance. He was brought to his knees and his hands that were previously covering his genitals were parted away so that his insipid manhood was exposed to them. He nervously looked up at t...

The Petworthy Finishing School Ch. 02

by Farinholt777 on Sep 16, 2017
Novels and Novellas

Chapter Two Where Mitten Becomes Oriented to her New Life at Petworthy Finishing School Because Mitten had a long time to consider her plight, she began to try to discern what was expected from her; by Daddy and by the Headmistress. The first problem was that she wasn't supposed to consider it a plight. It was appropriate for Mitten to feel like she was a...

A Professor's Tale

by binacontenda on Sep 11, 2017
Anal

I was beginning to think seriously about taking work outside the teaching profession that sunny, early fall Saturday, and I hate to think of what I would have missed if the phone hadn't rung during my lunch. The small college town of Giles, Michigan didn't seem to be able to offer any interesting positions for me in either of the two local colleges, and the...

By Day, By Night

by rick_oh on Sep 17, 2017
BDSM

This is the story of three females and the contrast between their professional and personal lives. They are employed as institutional discipline administrators at a reform school for males. Sandy and Veronica are experienced mistresses and Kendra is a new punishment mistress. Let's take a look at a typical workday. Part 1. By Day: Sandy Sandy stood nonchal...

RTFM

by astuffedshirt_perv on Sep 26, 2017
Toys & Masturbation

Note: This story takes place in the near future. The toy in this story was inspired by a story on another site, "The Curator," and is used with permission. Google "Streetwalker Squid Stimulator Deluxe with Partner Play" to find it. Karen started to shake in her silken sheets as her orgasm hit. Despite being alone in her apartment, she instinctively grab...

Naughty Naomi

by toocold on Sep 19, 2017
Fetish

When people asked Naomi what her job was, she told them that she was a school secretary, which was mostly true. She was a secretary, and it was a sort of school, though in actuality it was the sort of school that she previously assumed only existed in sexy fantasies -- an all-girl institution for ladies aged 18 to 21 who, with complex legal paperwork being s...