School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

Emma's Endurance

by ladyredmuff on Sep 19, 2017
BDSM

Emma stood in the cool bedroom, shivering slightly and feeling more terrified than ever -- and this had been a day of quivering fear and mixed dread and anticipation. Three weeks earlier, she had been at her Catholic boarding school, finishing her 'A levels' and wondering if she would get the grades that she needed to study history of art and when she could...

Show & Tell Ch. 06

by murphtsurf on Sep 14, 2017
Erotic Couplings

Since we'd been sitting there for over an hour, there was no time for another, "interlude," even if we'd both been in the mood. After our discussion and her revelations, it appeared that neither of us was interested in anything but letting all that had been said, by both of us, sink in. Walking her to her car, she finally noticed the bag I was holding and...

Ebony's Punishment

by Knot_By_Numbers on Sep 13, 2017
Fetish

The misbehaving young woman is real but the story is purely fiction. Enjoy the story and pass along your comments, there may be more of her since she loves to read about herself in such naughty situations. Thanks! KBN It was her last class of the day and she was glad to be going home soon, it had been hot in the school all day and she wanted a nice cool bat...

Never Satisfied

by joe1018 on Sep 12, 2017
Toys & Masturbation

Amy is an 18 year old senior in high school. She is captain of the varsity cheerleading squad, straight a student, dating the quarterback, and turns every head as she walks by. With perky D cup breasts and, what many guys referred to as a badonkadonk, both guys and girls get aroused watching her. Amy always enjoyed walking around school and public places in...

Ch. 05 Angela's Confession

by Bushman on Sep 17, 2017
Mature

I ON HAVING A FAMILY I'm Angela, a twenty-nine-year-old college professor with something to confess. I have witnessed a grace and an openness on the part of a seasoned married couple that I envy and would emulate. Granted, my dear step-brother Bill and I each developed a strong physical attraction to both Herb and Lianne; additionally, gaining their friend...

Life As It Is Pt. 01

by Tacobox on Sep 16, 2017
Novels and Novellas

I.Mickaela The first time I saw her, she was leaning over the bar, ordering a drink. I watched her for a few minutes-I watched the way her long, light brown hair fell across the front of her shoulders and onto her smooth, tan arms. I watched the way her smooth, beautiful hands, with perfectly manicured nails, wrapped around the bottle of beer that she had j...

A Chance Encounter

by Chimney Sweep on Sep 14, 2017
Erotic Couplings

My first year of college was rough in many ways. The classes were harder than I expected, the freedom was more difficult to manage, and the relationships too hard to maintain. I had kept a long distance relationship with my high school sweetheart, but it died near the end of classes. I was very depressed that summer and very lonely. I worked ridiculous overt...

Valentine's Day Teddy Bare

by clinton09 on Sep 2, 2017
Erotic Couplings

[©2011 BY CLINTON09; ALL CHARACTERS ARE OVER THE AGE OF 18 WITH IDENTITIES DISGUISED; FOR AGES 21 OR ABOVE] [Nerdy Valedictorian guy and shy Salutatorian girl are hooked up as a joke by high school gossips on Valentine's Day.] * Arnold was the archetypal 'nerd', with thick glasses, a 'nerd-pack' (calculator, mechanical pencil, cheap pen) in his top pocket...

Heat

by madengineer3 on Sep 14, 2017
Romance

I guess I should introduce myself. My name is Mark Turner. Have you ever noticed that sometimes reality can be stranger than fiction. That point was driven home to me over twenty years ago. At that time I was in grad school working for my masters in engineering physics. I had enough money to be able to afford a reliable, older, car and have an apartment to m...

High School Fun

by jazzyjeff98 on Sep 12, 2017
Erotic Couplings

As I sat in my 12th grade homeroom class, for what appeared to be another boring day, considering I had no homework to do as usual, it suddenly became more interesting. Crystal walked in about 10 minutes late, which was normal for her if she even showed up at all. Our teacher, Mr. Harrison, was very laid back and liberal and pretty much let us do as we pleas...