Headmistress Stories

651 results
Orientation
Length
Source
Infinite Scroll

Mandy Makes a Man of Mark

by RetroFan on Sep 19, 2017
Erotic Couplings

INTRODUCTION & DISCLAIMER - Set in Miami in 1964, this tale features the story of Mark, an 18-year-old student and Mandy, the mini-skirted single mother who lives across the street. Mark has always liked Mandy, but his prejudiced, God-fearing mother detests her, thinking she represents everything sinful in society today. Mark's long-suffering father just wan...

Tower of Babylon Pt. 03

by mrfudan on Sep 28, 2020
Sci-Fi & Fantasy

The Gaze of the Abyss Once she lost the attention of the retributive head mistress, Norma's life settled into a type of normalcy and mostly boredom, much to her relief. The vast majority of the female slaves served purely as decoration, housed and kept at exorbitant expense as a status symbol. The unseen potentate had detached private quarters where he kept...

Kellie and Brad Ch. 04

by drteetho on Sep 13, 2017
Romance

AUTHOR'S NOTE: This is the fourth chapter to a multi-part story, I would suggest reading the first three chapters before this one to understand the whole story. Please enjoy. She hated airplanes. She had ever since, as a seven-year old, she went on vacation to Florida with her family over March Break to visit Disney World. The vacation itself was fine....

The Witches of Ravenrook 03

by FinalStand on Sep 18, 2017
Sci-Fi & Fantasy

My thanks to PF for his editing handiwork *Imagine a life without Love; no Hate, Pride, or Passion* (There is a great deal of violence in this tale but I promise it will make sense before we are done. The 'hero' is no Conan the Barbarian -- normally. Slapping girls and woman is very abnormal but I hope understanding will come) "Hey Sally," I caught Sally...

The Black Power Virus: Graduation

by amb_anonymous on Sep 13, 2017
Interracial Love

This side story is very 'action' heavy, compared to all the other chapters. It felt a little bit immature in a 'grab as many groceries as you can in 60 seconds' sorta way, but I just really wanted to do a piece set on the post-virus education system. It's also the first time that we have a black, male main character. As always, leave as much feedback as pos...

Augmented Confidence

by Iwroteathing on Jan 7, 2019
Exhibitionist & Voyeur

Seraphina Kensington knew her house was a big family mansion, but she couldn't help but dwell on how empty it seemed while her husband was at work and her only son was at school. Seraphina had one goal in life, to marry into wealth and focus on enjoying her family, a goal she had achieved aged 24 when she found Tristan. He was from a wealthy family and had a...

Warren Baker's Valentine

by geronimo_appleby on Sep 16, 2017
First Time

Another Valentine's Day contest entry from me. I did think to use this scene as the precursor to a multi-chapter series. There was a lot of potential in subsequent scenes where Warren could enhance his sexual repertoire, but I got bogged down in the Granny's Dirty Photographs series recently and wanted to spread myself across a few more Lit story categories...

63 for a Handjob in the Garage

by MonsieurMaster on Sep 16, 2017
Erotic Couplings

This view was shitty. I couldn't really expect too much, considering I was waiting in my car in a parking garage of all places. I mean, you're only really suppose to be there for mere minutes; there's no point in trying to make the view interesting or pleasing to the eye. But I would really like something else to look at than a crumbling old building. Su...

A Sissy Saga Ch. 01

by Snurge on Sep 13, 2017
Novels and Novellas

The schoolgirl is wearing a gymslip of such a dark shade of blue it appears almost black. She is bending forward and stretching across a small table that boasts a cover of purple chenille, resting the flattened palms of her hands on the hard surface and pressing one side of her flushed face between them. The back of her skirt as been folded up to her waist a...

In Over His Head Ch. 10

by mouseyman99 on Nov 25, 2017
Sci-Fi & Fantasy

When they finally got home to their huge but decaying estate, she uncurled herself out from her coat and hopped out of the carriage, stretching. She'd be glad for a warm bath and a snack, too. She wouldn't be able to relax, though, until her grandmother had said her piece. She shuffled into the house, behind her grandmother, hoping that maybe if she was quie...