Headmistress Stories

651 results
Orientation
Length
Source
Infinite Scroll

Headmistress' Slut

by mummys dirty angel on Sep 12, 2017
BDSM

Standing in the playground waiting for my daughter to burst through the school door, my thoughts of how fast the years were passing were broken by a familiar figure walking towards the entrance to the large hall, adjacent to the main block. I turned away, hoping she didn't catch me staring, but my curiousness over her brought my eyes back, resting on her cur...

David's Tall Girls' School Ch. 05

by Thorilla on Sep 19, 2017
Fetish

(It was late autumn of 1960 and I was 20 years old and was following my hobby of bird watching. I had unfortunately been captured by Amelia Wiff-Naseford, headmistress, for being a Peeping Tom in the grounds of 'Dentwood Finishing School for Tall Girls aged 18 to 20 years old'. There were 120 girls registered at the school. I had decided not to get the pol...

David's Tall Girls' School Ch. 17

by Thorilla on Sep 19, 2017
Fetish

(It was late autumn of 1960 and I, David Shaw, was 20 years old and was following my hobby of bird watching. I had unfortunately been detained by Amelia Wiff-Naseford, headmistress, for being an alleged 'Peeping Tom' in the grounds of 'Dentwood Finishing School for Tall Girls aged 18 to 20 years old'. There were 120 girls registered at the school. Clearly I...

St. Agatha's School for Herms

by YKN4949 on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 1: The New School I felt so disoriented. It was probably even worse than when my family had first moved me to America ten years before. I was just starting to getting ready to start my last year high school, I was eighteen and all of the sudden my parents told me that they wanted me to go to some private school in the middle of nowhere for TWO MORE...

A Sissy Saga Ch. 07

by Snurge on Sep 15, 2017
Novels and Novellas

The following morning Sammy was in Mrs Pardoe's class sewing a plain white collar onto a skimpy black dress. It was a compulsory project. During their first term all sissies had to produce their own parlour maid outfit, and it had to be done by hand because Mrs Pardoe claimed exclusive use of the only sewing-machine in the house. Sewing was one thing he hate...

Golden Rules

by peemypanties on Sep 19, 2017
Fetish

Disclaimer: *This story contains themes of an extremely sexually explicit nature. Every single character in this story is 18 and above. This story deals with everything pee. If you don't like that sort of thing, you really won't like this story.* Part 1 I hated going to new schools. They always intimidated me, and I never seemed to make any good friends. M...

David's Tall Girls' School Ch. 09

by Thorilla on Sep 19, 2017
Fetish

(It was late autumn of 1960 and I, David Shaw, was 20 years old and was following my hobby of bird watching. I had unfortunately been detained by Amelia Wiff-Naseford, headmistress, for being an alleged 'Peeping Tom' in the grounds of 'Dentwood Finishing School for Tall Girls aged 18 to 20 years old'. There were 120 girls registered at the school. Clearly I...

Schoolgirl Seductions Ch. 1

by PrincessKatie on Aug 31, 2017
Fetish

(All characters contained herein are aged 18 or above) (Copyright Princess Katie 2002) (Please keep special formatting "as is") (This is the first of 6 parts) (This story contains many scenes of a sexual nature-If you are offended by such material please go elsewhere, if not then read on) -------------------------------------------------- Chapter 1-The...

The Catch Ch. 01

by SlightlyRude on Aug 7, 2019
Transgender & Crossdressers

CHAPTER 1 -- the first catch There had to be a catch. There always was. And I fell for it every time. I was gullible and generally crap at life. I went to a crap school on a crap estate in a crap town. I wouldn't say my parents were crap, just a bit disorganized. They loved me and each other, just incompetently. I inherited their lack of talent. When the c...

A King's Touch Ch. 04

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

Sara stood on the auction block and tried not to cringe under the stares of the eager wizards who were arguing amongst themselves. The auction had yet to begin and already she could tell the tempers were starting to flare. Staring around the room, she was surprised when a tall wizard caught her attention. Philip! I can't believe he risked death to find me....