School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

Four F Girl

by SplendidSpunk on Sep 16, 2017
Exhibitionist & Voyeur

(This will be at some point in time a BDSM story, though I am not sure when it will get there as I am still organizing the input from the star or co-star of this Tale. I know where she wants me to start and where she will end up but I am not sure if a straight line telling is going to happen. In any event you have been warned. This is meant to be told from h...

Kenzi's Sexy Older Neighbor

by SexxySelina on Sep 14, 2017
First Time

Kenzi Reinman sat up in bed, slipping off her sleeping mask. Her breathing was heavy, and there was a slight glisten of sweat on her chest, making her white tank top cling to her breasts. She had had an incredibly sexy dream- a forbidden, naughty, delicious dream. It had been about her much older, hot neighbour Mark Grath. He was old enough to be her daddy,...

Teacher Outcast

by EdRichards7030 on Sep 13, 2017
Mature

While pouring coffee in the break room one morning, I got my first look at her. Being a male science teacher in the middle school, I was a little outnumbered by the other, mostly female, teachers. Several of them had interviewed Miss Northrop for the English teacher position opened months earlier. Since then, there was a non-stop flood of negative gossip abo...

Sam's Pink Panties

by EasySleazy on Sep 18, 2017
Transsexuals & Crossdressers

Sam and I had been friends for as long as I can remember. We met way back in preschool when he stole some crayons from my cubie, I complained to the teacher and he cried his eyes out until the end of class. That image right there- that's the Sam I'll always think of. I don't remember how we became friends, I think I've always felt sympathy for people who cry...

Cindy Lou

by jsmangis on Sep 25, 2017
First Time

The following is a story based on people and places that I am very familiar with. All of the names and places have been changed to protect those who were involved in what happened so many years ago except for the title character: Cindy Lou As I reach the autumn of my life and am mourning the loss of the love of my life and bride of nearly half a century,...

A Little Problem

by msound1 on Sep 19, 2017
Fetish

I keep getting pregnant. I can't stop. It's almost like a sport for me. I swear, I deserve a damn medal. I've spent eight out of the last ten years pregnant, and my pants are getting tight once again. It started in high school. I was a little slow getting to the perks of puberty, but when I got them, I got them in spades. Less than five feet became almost s...

Growing Pains & Pleasures Ch. 01

by SafTman2 on Sep 14, 2017
Erotic Couplings

Like a lot of women; I married young, without much sexual experience. I was eighteen and had never slept with anyone but my husband. In high school I dated, had a very active social life, cheerleader, Homecoming court, all the "right" things. I had petted a little now and then, but no boy ever even touched my breasts and I had no idea what a "hard-on" was ba...

Pornstar Ch. 04

by SimonBrooke on Sep 14, 2017
Novels and Novellas

Pornstar Ch 04: Being an Item We walked up the hill through the wood. Nancy wanted to hold my hand, which was cool with me. For a long while we didn't talk, and that was OK too. At one point I slipped on a tree-root and caught my ribs, and just doubled up, gasping. Nancy knelt down and held me. After a couple of moments it was a bit better and I straightene...

Ben & Nancy Ch. 01

by D.C. Roi on Sep 16, 2017
Novels and Novellas

Passion in James County XV: Ben and Nancy Ben Morris and Evelyn Thomas, as nude as the day they were born, groped at each other's bodies as they made their way across Ben's bedroom. They collapsed on the king-sized bed and Ben rolled on top of Evelyn and began to suckle her ample breasts. "Oh, God, Ben!! I...I want you!" the woman groaned, writhing under h...

Teaching Cristina Ch. 01

by likebadfun on Sep 12, 2017
Mature

A couple of Fridays ago my daughter Nancy (18) brought her best friend home from high school to stay for the weekend. Nancy's friend, Cristina, also 18, was a shy Filipina, only 5'0". I figured her lithe, petite figure had a C-size bust. Cristina, like Nancy and all the other girls at the high school, wore a neat, white blouse and the school's regulation pl...