Sissy High School Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

A Change Of Luck Ch. 01

by KremnaPita on Sep 13, 2017
Transsexuals & Crossdressers

I met Mary when I was still going to high school and I immediately fell in love with her. But, since I was very shy I could only worship her from a distance. I just loved her perfect breasts that weren’t too big but just about the right size, her curly brown hair that always smelled so sexy and her sweet ass that had the perfect bounce when she was walking....

My Renaissance Ch. 04

by Modern_Citizen on Sep 15, 2017
Exhibitionist & Voyeur

Chapter 4. I meet Rachel. Brian brought Rachel over to the house that Friday, the day after he watched Crystal and I making love out in the Florida room in the hot tub and on the couch next to it. I guess he was feeling a little frustrated after watching the show with Crystal without a female around for the perfect sort of happy ending. It was the first ti...

Wife Has a Plan

by underdrive on Sep 17, 2017
Loving Wives

Note: There will be at least two chapters to this story. It isn't the most graphic sexually, but it is a sexually inspired tale of a wife taking control over her husband. I hope you enjoy. ***** This story began ten years ago at my ten year high school reunion. At the time life was great. I had no idea of what was to come. No idea that I was going to be he...

Three For Tea

by jimmydanger on Sep 16, 2017
Anal

Sara and Ron had been a couple for the entire time they were in high school. Ron played in a local rock band that often played at the school dances, which is how she met him. He was a strikingly handsome young man, and slightly full of himself. Sara was a beautiful young girl herself; she had medium length brown hair and was rather thin. But it was her eyes...

Third Quarter Luau Ch. 01

by junebugg011 on Sep 16, 2017
Romance

I never would've thought I would end up here in this situation. My parents: dead. All my life I never would have guessed they'd end up this way. Both murdered by a drug lord. A simple case of the wrong place at the wrong time. No,my parents didnt do any drugs or drink. They were just out on a much needed date, to which I had convinced them to go on. "Mom, D...

Do You Want Larger Breasts? Ch. 01

by SplinteredSteel on Sep 14, 2017
Erotic Couplings

It was the day that Karen Leasor looked forward to the least: her group swim at the rec center. Karen had a close group of friends who all went to the gym together, with each day focusing on a different workout. It was a great way to stay in shape for Karen, who had lost 10 pounds in the four months she had participated. What was wrong with group swim? Kare...

Kate Lets Loose Ch. 01

by bigjerseyguy on Sep 14, 2017
First Time

Kate wasn't an attractive girl. She wasn't ugly, but you wouldn't describe her as plain, either. She didn't have a nice body, she didn't have nice legs. Her boobs were small but nice enough. She didn't do herself any favors by never putting on make-up or fixing her hair. She figured since she wasn't attractive, why bother. She grew up in a small town in Ver...

On the Bus: Excuse Me

by Tara_Neale on Sep 11, 2017
Chain Stories

Jamie slid quietly down the too narrow aisle. "Excuse me, excuse me, excuse me," was her mantra as she went. The bus was packed and for a moment she feared she would not find a seat at all. Tears sprang to her eyes at the possibility of having to take the next one. She wanted out of this place now. No, she needed out of here. Desperation ate at her gut. A li...

Welcome to the Sisterhood

by _M_Odette on Sep 14, 2017
Fetish

There is a very interesting campus in a rural part of New York State. The campus has both a fraternity and a sorority. All members of the fraternity and sorority houses are older than the age of consent, of course. The fraternity and sorority houses are on a street separated from the rest of campus housing. Both houses participate in various forms of pledge...

She Thought I Was Sleeping

by GoodEater on Sep 16, 2017
Toys & Masturbation

So after all of these years I decided to finally write that diary I have always considered. The only problem with the diary concept is that someone always finds it. And if someone finds it, they read it. And, I would always be afraid of that so I wouldn't write any of the real good stuff. And if you are not going to write the good stuff, then why write anyth...