Sissy High School Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

Almost Heaven Ch. 03

by 99_percent_oral on Sep 13, 2017
Loving Wives

Jeanne sat behind her desk as she waited for her next appointment. She was now a middle school teacher and parent conferences were being held. She was hurriedly scribbling notes from her last session and Buddy's dad was standing beside her before she was even aware that anyone had entered the room. Looking up, Jeanne shivered perceptibly. I wasn't even awar...

Angie's Education Ch. 1

by CNDPhD on Sep 16, 2017
First Time

Angie stood at the edge of the sidewalk waving, as the red minivan pull away. Alone, she stood for the first time in her life. Her parents and her younger brother were in the van, leaving her standing alone to face her first day at college. To say she had lived a sheltered life would completely fail to capture the degree of social isolation she had experienc...

Nick Helps Val with a Problem

by Cerby565 on Sep 12, 2017
First Time

NOTE: All characters in this story are fictional and of legal age for all of the various activities (over 18 years of age) that may occur. I am the sole owner to the copyright of this submission * My name is Nick and this is the story of how I finally lost my virginity. I was a Senior in High School at the time, and the only one of my friends that still...

Broadly Sexual Pt. 01: The Beginning

by broadlysexual on Sep 14, 2017
First Time

As this is my first submission, I'll tell you a little bit about myself to set the stage. At the time of writing, I'm 27 years old, tall, in good shape, white, and pretty much always horny. The point of me writing is to really explore, through writing, my sexual history. Until now I have experimented with lots of things, men and women, online relationships,...

Me and My Shadow Ch. 01

by MasterOfSin on Sep 2, 2017
Erotic Couplings

A new project! I'm not sure where i am going with this but i do have a few favors to ask for your readers. i wasn't in the popular click in school so i have near no idea what people with mire then 2 friends do on a day to day basis so I'm gonna kinda take suggestions from comments. Otherwise updates might be slower than my normal speed. ***** I first notic...

Reuniting at the Reunion

by ladventures1 on Sep 24, 2019
Group Sex

I grunted with effort as I lifted the box of props for the photo booth. It was full of silly hats, oversized sunglasses and little signs for people to hold while posing for pictures during the reunion later that night. The room was all set up, and the reunion committee and volunteers were starting to separate. Those who lived in town were headed home. Those...

Paranormal Coed Pt. 01 - Introduction

by Woreign on Jul 9, 2019
Sci-Fi & Fantasy

Chapter 1: Meet Britney Davis Britney Davis was 18 and had just graduated high school. As the only child of an overbearing mother, she was miserable at home. Her mother attempted to control every aspect of her life, and Britney resented her greatly for it. Working part-time and summers at the local country club was a Godsend, because it allowed her time awa...

Kittie Comes Out Pt. 02

by Arpea on Sep 17, 2017
Group Sex

This is a continuation of Part 1. To follow the story, the reader should read Part 1 first. ***** After meeting in law school, Kittie and I got married when we graduated and both had successful legal careers in downtown law firms in a major city. She's a tall, blue-eyed blonde with plump breasts that ride high on her chest and beautiful long legs. We had...

The Submissive Wife Ch. 02

by Authorman1969 on Sep 16, 2017
Fetish

Bobby and Debbie keep learning about their dom/sub needs until they finally meet. Future Chapters will focus on their relationship and marriage. Thanks to those who comment. ***** Bobby and Debbie's desires for domination and submission continue to grow as they grow up cementing the roots for what will become their lifestyle as husband and wife. Bobby and...

Like a Woman Scorned

by BadBoyPierre on Jul 13, 2020
Erotic Couplings

After our blonde eighteen-year-old smoke-show catches her boyfriend cheating, Ashlyn devises a plan to get revenge. However, the plan takes an unexpected turn when innocent flirting leads to passionate, mind-blowing sex with her ex's fifty-five-year-old father. Please email feedback, suggestions, and detailed story ideas to my profile. --------------- "W...