Headmistress Stories

651 results
Orientation
Length
Source
Infinite Scroll

When Angels Cum Ch. 08

by CapDragon121 on Oct 31, 2018
Sci-Fi & Fantasy

Author's Comments: Someone asked me for more action. I am going to try, but this isn't that kind of a story. Besides a couple of major battles, I've planned, there isn't going to be much action. Adventure yes, but not too many fights. * I've had a revelation while writing this story. I've always been squeamish about anal, but once I removed the disgust fac...

Naughty Naomi Ch. 04

by toocold on Sep 19, 2017
Fetish

This has been much-delayed and is only half complete so is shorter than previous chapters but positive feedback for part 3 wanted more and wanted dirty, so toilet action follows - you're warned if that's not your thing. I hope to get back into the swing with this, if I have time. Everyone's legal age and consenting and in my imagination anyways... All thre...

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 King's Touch Ch. 01

by dragontatto on Sep 19, 2017
Sci-Fi & Fantasy

Sandova, 2118 "Prince Philip." Philip turned around and couldn't believe his eyes. In front of him was his Sara, but not the same Sara. She still looked like the little vixen who had tagged after him, but the stillness which clung to her was not the same high energy radiance he'd become accustomed to seeing in Sara. "Sara. You're back! It's good to see...

The Doctor is In Pt. 03

by limeybato1 on Apr 9, 2019
First Time

I apologize to my readers. I incorrectly referred to a cervix as a hymen in my last missive. My mind doesn't work so good these days that's why I'm writing this down. When I have an erection I have even more trouble... So please forgive me. Anyway, I hope no one is reading this as prep for their medical exams! Talking about hymens reminds me of this story...

Persephone's Secrets Pt. 03

by mollycactus on Mar 28, 2018
Exhibitionist & Voyeur

Sunday, after Persephone and Jocelyn had accomplished whatever weekend tasks that needed to be done, they went out to eat together, and went to the movies. In the darkened theater, they leaned against one another, and held hands. It was a wonderful evening. On the way back to Persephone's home, they agreed that Jocelyn would virtually 'move in' and stay over...

Courtview Refinement College Ch. 01

by Zack2981 on Sep 13, 2017
Erotic Couplings

In the fifty years since the foundation of the Courtview Refinement College for Women, there had only been two deans. At other colleges, a dean could be expected to serve between eight and ten years and would then step down to enjoy the benefits of retirement. But at Courtview, nothing could beat the benefits of the position. Being the dean of such a prestig...

The Romantic Rollercoaster

by u1u1u1 on Jul 4, 2018
First Time

It was a brisk October day. Emily strolled to work. She spent her Saturdays working checkout at the grocery store to make some spending money. She wore a light silk scarf over her uniform, which gave her an air of elegance and sophistication beyond her age. She arrived in good time and sat at her checkout. Her manager, Damien, asked for a word before she be...

Erotica Magica

by JackOLantern on Apr 18, 2019
Fantasy

To the people of Greenwall, the Des’Cantier family were the closest things to celebrities that anyone could be in such a small town. They were well-loved and admired by most of the townsfolk for as long as they had lived there for generations on end. However, these days when someone spoke the Des’Cantier name it was usually followed by a shake of the head or...

Open in Reader

Sissy's First Day

by whispy_sub on Sep 13, 2017
Transsexuals & Crossdressers

Sissy let out a disheartened groan as he closed the classroom door. He looked down despondently at the discipline demerit clutched in his gloved hand, "It's my first day and already I screw something up; I can't believe this." It was only his fourth hour here at the Academy, and already he recieved a demerit. He wasn't quite regretting his decision to enrol...