Sissy High School Stories

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The Domme Diet Plan Pt. 01

by subm_atty on Sep 11, 2017
Fetish

Day 1—The Plan I have been fat as long as I can remember. I have tried various diets with no lasting success. Being uncomfortable with my body was probably one of the many factors that drew me into being a submissive. Two years ago, I met the Domme of my dreams. My Mistress was about 5'10" but towered well over 6' tall in the heels she usually wore. Her hai...

High School Sweethearts Pt. 03

by Lawyerlyzach on Sep 25, 2017
BDSM

The next morning Andi and Jack got up and did their makeup. Andi then produced the clothes that she wanted Jack to wear, and he put on his chest piece, and got dressed. The skirt on Sunday was even shorter than the previous one. Jack was mortified that a good breeze would be enough to let everyone see his ass. The two went to breakfast, and then spent most...

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...

The High School Principal Ch. 04

by JohnLaw1950 on Oct 7, 2019
Erotic Couplings

The Cruise© The school year finally ended. The Seniors graduated, which meant there would be a new batch starting in the fall. Lexi and Miranda both graduated and were off to college out of state. That meant I wouldn't be getting any more pussy from them. At least Lexi's mother, Marcie, was still available. Although she had started dating again, thanks to,...

High School Dilemma Ch. 05

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. L...

High School Dilemma Ch. 04

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. This particular episode is very XXX with pee scenes etc. However, I do know many parts of my stories will not appeal to all of you. I only wish there is enough to make each of you happy. To those who have given me constructive criticisms as well as those with praise tha...

High School Dilemma Ch. 06

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. I...

Amanda

by tsto123 on Sep 25, 2017
BDSM

High school was not a fun place for me. Being more of the geeky outsider, more interested in science, computers, and the related pop-culture associated with those interests, meant I had few friends. It also meant that I was so far out of the social ladder that I wouldn't be able to see the bottom rung with a pair of binoculars. So, when Amanda, one of the mo...

Cosplay Wife, Cuckold Life

by SatinSlip on Dec 3, 2017
Exhibitionist & Voyeur

My wife and I were high school sweethearts. Kimberly was a brilliant, lovely girl. With big breasts and long curly red hair. Academic and popular. I was nerdy, and smart. A bit to feminine to be handsome. I was shy and weak. Neither of us had been with other partners and our sex life was pretty vanilla going into our mid twenties. Mostly missionary style...

Making of a Sissy

by danni5858 on Mar 2, 2020
Erotic Couplings

A number of years ago, I was on an international excursion with my daughter's high school-aged travel water polo team when a series of rather unexpected events resulted in me having a fling with another player's mother. Truth be told, I had long been attracted to this woman, Rachelle, whose daughter played the same position as my daughter. Despite the girls...