Sissy Schoolgirl Stories

13,642 results
Orientation
Length
Source
Infinite Scroll

Finishing School For Ladies Ch. 01

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One -- The Beginning Valerie Swindon sat at her desk in her small study grading exam papers. A shadow fell over the opaque glass panel of the door and she looked up at the ornate mantle clock and realised it was time. She arose from her chair and came around to the front of her cluttered desk and unzipped her skirt. She caught it before it pooled...

Sometime Succubus Pt. 02

by Quince on Sep 12, 2017
Erotic Couplings

PART I A week, later, Friday, October 31st, at around 7:30 in the evening, and Tres had a lot on her mind. A little less than a week ago, her roommate and best friend had knelt before her on her bed begging for an orgasm which Tres had eventually supplied. That evening had been, at once terrifying, blissful, confusing, and something like forty seven other a...

Beach Sex

by Wormwood_too on Sep 13, 2017
Exhibitionist & Voyeur

The sun broke through the mid-morning haze as Brandy and I made our way over the dunes and toward the beach. For the last couple days, we had been camping at Watch Hill Campground on Fire Island. It's a beautiful place, well removed from the hectic pace of the city. Unfortunately, the campsites are placed so close together that we haven't had much privacy in...

Arabian Nights Pt. 04

by MicheleNylons on Sep 26, 2017
Transsexuals & Crossdressers

Back in her cell Sarina helps Michele undress. "That suit isn't too bad; you can just brush it and hang it up. That blouse will need a soak to get the come out of it. Check out your lingerie and stockings and if they have any rips or tears just ditch them. You get an allowance for lingerie and hosiery; the boys are always tearing them because they are so ro...

Dealin' With Dawnie

by MTL17 on Sep 16, 2017
Celebrities & Fan Fiction

Author's note: This story is based in a slightly altered future a few years after Buffy the Vampire Slayer ends so all the characters, and those who would be playing them, are over 18. It's also from Faith's POV. ** One of the, many, things I like about dusting vamps is, if you're doing it right, there's no mess. Also no body, and B tends to be a nag if s...

He Fucked My Girl Ch. 05

by xleglover on Sep 25, 2017
Loving Wives

The next morning I had a massive hangover, but luckily Jen had gotten me to drink a lot of water and take aspirin, so by the time we got to the airport I felt better. Jen giggled the entire time about how I'd let our friends get me drunk. She was in a great mood, giddy like a schoolgirl. I asked her about it, and she said jovially, "Why shouldn't I be in a g...

Wives and Lovers Ch. 02

by GreenFingers2015 on Sep 26, 2017
Novels and Novellas

WARNING TO READERS - This is a long, rambling story and VERY British which has been divided into several parts for ease of editing and reading. The individual parts will make more sense if read in sequence as they follow straight on chronologically. Most, but not all chapters contain some sexually explicit sections and the story has a strong theme of taboo...

Alex Ch. 08

by HappilyM on Sep 19, 2017
BDSM

Author's note, please do not feel intimidated by this being a long story that started in Romance. I feel even if you do not go back and read the first 7 chapters, you will still enjoy this possible power exchange. * The next three weeks were spent organizing Alex's books for the farm and reading everything I could about the role of a sub. The more I rea...

Toy's BDSM Adventure

by PhilCanyon on Sep 13, 2017
Illustrated

This story is inspired by the same couple that supplied the artwork. For the purposes of this story we'll call them, Mr. and Mrs. VoyToy. This story is an attempt to write one of their fantasy BDSM adventures. I hope you enjoy it and I'm sure you will enjoy their artistic depiction of the story!! Please leave comments, as The VoyToys will undoubtedly read th...

A Wife Never Tells

by darkoverlord6 on Sep 18, 2017
Erotic Couplings

The noise from the bar sound system and the endless chatter of my fellow convention goers reverberated around me as I sat nursing a glass of wine and longing for this conference to end. My name is Jane, and due to the luck of the draw, I was chosen to represent my company at the annual Energy Expo trade show in San Francisco, so here I was knee deep in engin...