Sissy High School Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

Steve & Hot Sara Seduce Me

by DW46 on Sep 13, 2017
Group Sex

I was out of town at a training session for my company when the usual "introduce yourself and say where you're from' thing started. A guy named Steve introduced himself and I realized it was the same Steve I had attended high school with many years before. He was still his tall, lanky self. When we were in high school, everyone said we could be brothers, pa...

The Drawing

by dragonfire6 on Sep 13, 2017
Erotic Couplings

During my first year in college I had become really close friends with Carl and Faith. Most nights we would be at Carl's apartment studying, talking and occasionally drinking ourselves silly. I had met Carl in my photography, as we were paired up by the professor on the first assignment. We both shared a love for motorcycles and that stood as the foundation...

Heather's Revenge

by alphawaves on Jan 14, 2019
Fetish

Heather and Ryan Starwood were twin siblings. Heather was a gorgeous brunette with long soft legs, a nice ass and big double D breasts. She was smart, funny and had a great personality. Ryan was also highly attractive. He had a nice square chin, large muscles and a firm ass. In fact, most girls would agree he is one of the hottest guys in town. However, unl...

Night Out

by KatieBoobs on Jul 20, 2020
Mature

There was loud music emanating from the closed door in front of me. I took a deep breath and walked up to the entrance, two men in black, leather jackets flanking either side of the door. They both wore dark shades even though it was at night and their well-built bodies sent shivers down my spine. As I approached the door, one of them held out his hand and...

Frat House Slut Ch. 01

by Jay142 on Jun 12, 2019
Group Sex

Julie was one of the most popular girls in her high school. She was a cheerleader for four years and was elected captain in her senior year. She was on the Honor Roll, on the prom committee, school newspaper and vice president of her senior class. She dated Dan, the quarterback of the football team, and was elected Homecoming Queen. Not only was Julie popula...

Oil's Well That Ends Well

by Sfbullrider on Sep 13, 2017
Loving Wives

By the time I reached high school, I already knew what I wanted to be. I set my goal to become a high school teacher, and maybe coach a little baseball. I was a good athlete in high school, and lettered 3 years in baseball. I was also valedictorian of my senior class. I was offered a baseball scholarship to a small junior college, but I was set on becoming...

Sherry Baby, Will You Cum Tonight

by walterio on Sep 14, 2017
First Time

Authors Note: I liked this story line submitted in a reader request so I gave it a shot. The names are fictitious and all characters are at least 18 years of age. INTRODUCTION It was the spring of 1959 and Cliff Walters could not believe that he would soon graduate from high school. He had played his last high school football and basketball games and soon...

A Kuwait Man Becomes Christian

by Samuelx on Sep 16, 2017
Interracial Love

The path I've chosen to walk is a difficult one, but I feel that it's the right one for me. My name is Tariq Rahim Alkaabi and I was born on the island of Failaka in the State of Kuwait. November 17, 1988, I came into the world. An undersized little brown bundle of joy, as my grandmother Bashirah would constantly remind me in later years. My father Abdul Alk...

Best Summer Ever

by DG Hear on Sep 14, 2017
First Time

Thank you to Estragon for his editing and making this story a much better read. * I want to tell you about my best summer ever. I have to tell you a little about my past, then about our vacation to Myrtle Beach. It was with my mom and twin sixteen year old sisters. My name is Jim Miller. My parents still call me James and my sisters call me Jimmy. I'm fin...

Kathy's Engagement

by serpentongue on Sep 17, 2017
Loving Wives

"Did Keith give you that ring, Kathy?" Joni asked. "And is it what I think it is?" The two 21 year old waitresses were waiting for drink orders at the Sam Glance Saloon, a restaurant and bar that featured a heavy handed Western theme. Both wore cowboy hats and plaid blouses with the three top buttons unbuttoned, as the manager's dress code required. "Yes,...