High School Sissy Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

Megan's Crescent Moon Atonement

by badger_ravenmoon on Sep 16, 2017
Novels and Novellas

This is a work of pure fiction. Any relation between the events and characters herein and reality is coincidence and may the gods help anyone who has done anything like this. This first story is “slow-burn” because I am first and foremost a storyteller. Later stories will assume an understanding of the Way, and will be a little more fast-burn. Also be aware,...

My Online Love Affair Ch. 3

by Traci Spencer on Sep 26, 2017
Erotic Couplings

Kelly: I was just getting home from work and it was 7:30 PM and I thought I would give George a call. I dialed his number. "Hello?" Greg answered. "Is George there?" I asked. "Just a minute...DAD, some lady is on the phone for you." I heard Greg yelled. "Hello?" George answered. "Hi. It's me, Kelly." I answered. "Oh, hi babe. I can't talk right now; c...

School Drop Off

by daciasdesire on Apr 19, 2018
MILF

Spencer Askren leant down and hugged his daughter Amy goodbye. “Be good in class today sweetie. I know you will crush your physics test,” he told her before giving her a kiss and sending her off. “Thanks Dad,” Amy replied. “Don’t forget I have softball tryouts this afternoon,” she told him as she left the school drop off area and made her way to the entrance...

Open in Reader

High School: Zero to Hero Ch. 00

by yoursilentknight on Sep 19, 2017
First Time

This is the beginning of a rather long series (Prolog, ten chapters, and an epilog). There is also a follow up series in the works, so if this is well received I hope to continue the development of the characters. This is not a quick "stroke story" but it is not a novel either. Each story will be branded with the 'theme' that best fits. Story elements will i...

Susie Ch. 09

by Susie_O on Sep 15, 2017
Exhibitionist & Voyeur

Susie O'Connell tells me she is writing a journal and asked me to write something describing what "Trish" and I did after I met her. She said she wanted to have my perspective. I guess an introduction is appropriate first. My name is Howard Duncan. I am 19 and am about to begin my second year at the local community college. I am preparing for a career in ci...

The Learning Curve Ch. 01

by guitarman100 on Sep 16, 2017
Romance

I swear the longer I live the more I realize how truly fucked up this thing we call life is. We're taught one set of rules and ideals as we grow up. Then when we finally end up a "responsible adult" we find out that not everybody plays by those rules. In fact a lot of people don't. Then maybe we do a little reading that wasn't assigned in school and find ou...

Katrina Ch. 01-02

by DG Hear on Sep 13, 2017
Romance

This story is seven chapters. I will be posting two chapters at a time till all are posted. Hopefully every two days. Thank you to Linda62953 for taking the time to edit my story. Chapter 1: My name is Katrina but my friends and family have always called me Trina. I want to tell you about my life and the mistakes I've made; maybe some of you can learn fr...

Melissa's Mistake

by CityWolf on Dec 12, 2018
Exhibitionist & Voyeur

The big school dance was that night. Melissa planned ahead. She came there earlier that afternoon and dropped off her clothes. In a wooded area off the parking lot she placed a short skirt, tights, shoes, a blouse and a spare key to her car. She covered them over with leaves. Even the thought of what she planned excited her and caused her stomach to flutter....

Monster Girl World Ch. 03

by Venus444 on Apr 9, 2019
NonHuman

Chapter 3-Stalker Girlfriend part 1 Akira Kanzaki was a loner. To his fellow students and even his teachers he rarely interacted with anyone save his small circle of friends. He was a taller, slender young man who looked like he belonged in a gang, but those who knew him would say that he actually is a softie at heart who unfortunately inherited his father'...

My Husband's Dream

by SweetAss21 on Sep 17, 2017
Loving Wives

"When are you coming?" Lynn asked her best friend, Terri, over the phone. The two had been best friends since junior high, and even the distance of over 400 miles hadn't been able to break them apart. "I'm going to leave Friday morning, as soon as I get up and going. I'd like to be at your house by early afternoon," Terri replied. Although Terri was not loo...