High School Sissy Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

Grab Bag Transvestite Story

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

I am a part time transvestite, who, if I do say so myself, looks quite attractive when dressed as a woman. It has taken me years to become adept at makeup and being capable of selecting sexy clothing that is in my size and that suits me. I have also had a number of lovely encounters with other TVs and male admirers. You can read my True Stories on this site....

My First Honeypot

by WilliamRollins on Oct 3, 2018
Group Sex

When I was nineteen I was a hardcore athlete competing on a D1 college gymnastics team. I was naive growing up in a small town and my experience with the opposite sex was limited to two high school girlfriends who were even more innocent than me. My body was what you would expect from daily double training sessions and I knew I was fit but never thought of m...

Brandy Ch. 03-04

by TonyDowse on Sep 16, 2017
Novels and Novellas

Chapter 3 SHOWS In my experience it seems that there is one, really big difference between men and women's attitude to sex. Not that it applies to all men of course and there are some women who don't fit the pattern either - but, as a general rule I think it's true. Men like a 'show', a 'production', whereas women go much more for the atmosphere created by...

Tom & Sue & John & Debbie Ch. 11

by Reversecowgirl2014 on Sep 26, 2017
Novels and Novellas

Thanks for reading my series, Tom & Sue & John & Debbie! If you haven't read the previous Chapters, 1-10, please do so before reading this chapter. Otherwise, you're going to miss a lot of the details as each chapter builds on the previous chapter. Chapter 10 gives the readers a 'hint' as to what will happen to the characters as they continue to take the rea...

Debbie's Addiction Ch. 05

by masterofnymphoslut on Sep 19, 2017
Exhibitionist & Voyeur

Debbie stood under the hot shower trying to wash away the smell of sex that clung to her body. Every muscle in her body ached from the fucking she had just been given by Master and his five friends. Her breasts felt like two pieces of raw meat hanging from her chest. They had been pinched, squeezed, bitten, spanked and used more thoroughly than she'd ever th...

The Halloween Prank

by Rod_Walker on Sep 17, 2017
Loving Wives

My wife Linda and I have known each other most of our lives. We grew up in the same small town living less than a quarter of a mile from each other. We went to the same schools together starting with kindergarten. In most stories of this type I would be telling you how she humiliated me at the Prom or how I saved her chastity at a wild party. Unfortunately...

Kim Driver: Graduation Ch. 01

by 7footrabbit on Sep 16, 2017
Non-Erotic

Chapter – 1 The Beginning Day one of their journey through school they met; Kim Driver one of prettiest girls, the most athletic and the toughest kid in kindergarten, Ron Clark squirt kid afraid of nothing, tried anything but always got hurt and Lori Ferst little princess, teachers pet and didn't like to get dirty. They hit it off and became friends. Ron lo...

Three Kisses, One Past

by YDB95 on Sep 13, 2017
Erotic Couplings

I know everyone has their Christmas rituals, reading A Christmas Carol or watching It's a Wonderful Life and so forth. Mine is reading the last few pages of The Great Gatsby, where Nick waxes nostalgic about the "thrilling returning trains of my youth". From the first time I read that, when I was a kid from the slums trying to fit in at my ritzy private scho...

Learning to Love Louise

by RetroFan on Feb 12, 2018
Romance

Introduction & Disclaimer - Set in the city of Adelaide, South Australia, this is the tale of what happens when divorced single mother Louise moves in next to Paul, a never-married high school teacher. Paul is immediately taken with the pretty redhead but cannot work up the nerve to ask her out, finally getting the courage to do so after plenty of encouragem...

Oh Teacher, My Teacher Ch. 01

by coaster2 on Sep 15, 2017
Novels and Novellas

Author's Note: This story is situated in Canada and hence the different spelling and word choices. I hope it doesn't interfere with your enjoyment. It's the story of a man who has a hard time accepting good fortune. As always, I am indebted to Erik Thread for his skillful, insightful and helpful editing. Any errors are mine alone. * Chapter 1: My name i...