High School Sissy Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

The Corner Office Ch. 05

by tom6432 on Sep 14, 2017
BDSM

Chapter V -The previous weekend (This is a fantasy containing spanking and humiliation. If you do not enjoy reading this type of story please do not read it. Thank you to my editor you know who you are.) ------- I was in the dining room of my 45 year old administrative assistants' house waiting to pick up some documents that I needed for work on Monday....

Running into a High School Mistake

by MissLit on Mar 6, 2018
Erotic Couplings

***This story will be written in several parts. Also, this fictional narrative has a slow start! If a fast paced story is more your style I suggest you don't read this one! Thank you!*** 1 "Excuse you! What are you doing?" I asked while I was rushing down the stairs to my old bedroom. My heart was racing as I saw his hands flipping the pages through my di...

Transwood High Pt. 04

by BoobVillian on Sep 12, 2017
Transsexuals & Crossdressers

Christmas is Cumming... Authors note: All the characters in this series are over 18, this is the fourth part of the serious so be nice :-) Sorry for keeping you horny for so long, hopefully this satisfies. The story focuses on our main heroine, and some new/ old faces appear. Enjoy and leave comments! ******************************* 10/12/2016... 'Open u...

First Time Nudist

by WuLiMaster on Sep 13, 2017
First Time

I was on a business trip to Sydney, Australia and looking through a guide book to see what I could do during my time off. I had already walked across the Sydney Harbour Bridge, toured the Opera House and taken the ferry to Manley but the thing that caught my eye Sunday morning was the nude beach at Lady Bay. As a teen, I had avoided school showers. I was th...

Erotic Math

by WestVaCouple on Sep 12, 2017
Erotic Couplings

Why didn't I study harder in high school. Then maybe I wouldn't be taking these remedial math classes in the summer. I mean, I just graduated and I am supposed to be out partying with my friends before we all leave for college. But instead, I work at the pool in the morning, go to class in the afternoon, and do my assignments at night. It's just not right....

Young High School Football Coach

by jamisonh213 on Sep 12, 2017
Erotic Couplings

Note: This story will be written from two points of view. Lily is a hot wife that has been given permission to roam by her husband. Jonathan is the young coach giving his account of the events. ***** Lily: About five years ago I was working as a nurse at a rural hospital. One of my female co-workers was getting married. The gals at work decided to have a...

Gangbang Movies Ch. 01

by R. Richard on Sep 15, 2017
Group Sex

Chapter 01: Arianna All of the characters in this story are fictional and at least 18 years of age. The fourth story in the Gangbang Movies series, Ch 4 Charlotte, has been placed in Incest. Call me Zach. I was just a kid growing up in a town probably much like your town. The main highway cut the town in half. The rich people lived on the north side of to...

Old High School Crush Pt. 01

by Elkman1984 on Sep 13, 2017
Loving Wives

My wife was sitting on the love seat talking away on her phone when I walked inside with steaks fresh off the grill. I heard her say "Sounds great, we will see you soon" I asked who was that. Lynn replied "Britt, she is flying in from Washington for work next Thursday and wanted to know if I could pick her up from the airport." I asked how long she would be...

Zeek's Surprise

by EroticKeys on Sep 13, 2017
Romance

The door-bell rang. She wasn't expecting anyone. She looked through the door's security viewing hole. A well groomed man stood in front of her door dressed in sport shirt and slacks. His face seemed familiar. "Yes?" she said through the locked door. "Hello Patty. You probably don't remember me. It's Zeek from high school," he said. "Ohmygod. Zeek," she s...

The Teacher & Me Ch. 02

by Scarlett Marsden on Sep 16, 2017
Romance

It began when I pulled out the lost school uniform I had bought home when Jude and I moved in, after I finished high school. No, before I finished school, but once I’d moved out (boarding school). The pleated skirt, the polo shirt, the knee high stockings. “You know, I have to admit,” Jude said as I suddenly found him standing close behind me. “There is a...