School Sissy Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

Submitting to the Neighbour Lady

by Stillherer on Jun 8, 2020
BDSM

I went to high school with the Post twins in the late 60's. Tommy and Belinda Post. The Post twins were new to our area and it was rumoured that their father wasn't with them. It was our senior year and being 18 we just wanted it over with so we could get on with being adults. Belinda never gave me a second look but before he knew better Tommy struck up a te...

Sissy School

by zeta515 on Jun 19, 2018
Novels and Novellas

Copyright 2018 by Zeta All rights reserved This story may be freely distributed in electronic form but must include this copyright. Sissy School is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincide...

A Sissy Saga Ch. 05

by Snurge on Sep 15, 2017
Novels and Novellas

Miriam opened the door and poked her head through the gap into her daughters bedroom. "Sorry to call on you at such short notice darling, but the water boiler's buggered and I have no other choice but to ask Hardwick to go and have a look at it. I've no idea how long he's going to be, so could you take his first session?" Jennifer roused herself from the bo...

A Sissy Saga Ch. 15

by Snurge on Sep 15, 2017
Novels and Novellas

A fine day, thick and hot making Miriam Hancock's face dewy with sweat. She gazed at the house. Was this the place? She checked the card in her hand. No mistake. It was an unimposing Edwardian terrace house in a street of equally unimposing houses, narrow fronted, three stories high, the windows heavily draped. She went up a set of steps to a porticoed door...

Center of Attention Ch. 02

by Seethru57 on Sep 16, 2017
Group Sex

Disclaimer: All characters in this fictional story are 18 years or older, and all names are ficticious. This is a continuation series. Debbie Ross was sitting on her bed, writing in her diary about the events of the previous night. She wanted to keep those memories, and hoped to add new ones to the lusty events at Mr. Collin's home. Her thoughts were interr...

Black Man One Ch. 23

by Weak_White_Wimp on Sep 19, 2017
Interracial Love

As I peered through the darkness of the parking lot and towards the bushes where the other white husbands were hiding, my feelings of curiosity grew even more intense. "Richard? Come on already." one of the weaker, white husbands yelled in a heavy whisper. "Yeah. Hurry up." another whispered voice shouted from the darkness. Tentatively, I minced my way...

The BNWO changes my school

by sissymeretrix on Apr 29, 2025

The atmosphere at calmer waters college has changed drastically in the last month and a half, a new physical Education teacher had started. He's a tall black man with large muscles, he insists on being called coach. The students and teachers hadn't thought anything if it but a week after he started, the headmistress had changed personality slightly going fro...

Man to sissy

by fortifiedfortfightinfortnite on Jun 15, 2018
Fetish

I had asked out one of the cutest girls in school. Alex, being a cheerleader had no problem picking a quarterback, but to my luck I had worked up the courage to ask her and she excepted! When I had got to her house, I rung the doorbell, As she opened the door her aura enveloped me. When she invited me inside I didn’t hesitate. She then lead me and said, I co...

The Good Son

by sissysub34 on Apr 22, 2025

You sat in your room after just arriving home from school you had a long day dealing with the constant harrasment from your bully's constantly making fun of your looks and appearence looking more feminine than masculine constantly making fun of your looks and appearence looking more feminine than masculine you stand up of your bed and make your way towards t...

Sissy Boy Secretary Ch. 07

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the...