Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

Sanctuary Pt. 01: Aubrey Ch. 01

by inkstand on Mar 20, 2018
BDSM

"Barbra Streisand that hurts!" I said, rubbing the elbow I had just banged into the aluminum window frame. That was one of my trifecta of weaknesses; toe stubbing, papercuts and funnybone abuse. All I could do was to rub the prickling sensation skittering through my arm and grimace. The scene kept rolling past the window, an endless parade of decayed subdi...

The Role Players Pt. 05

by hollygurl29 on Aug 1, 2018
Transsexuals & Crossdressers

DISCLAIMER: This is a work of fiction and all characters represented here and in any additional parts of this story are all over the age of 21. This tale involved crossdressing, bdsm & role playing. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. The main characters in this tale are as...

From a Husband to a Dutiful Sissy Ch. 12

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Twelve: New Days, New Times, New Possibilities. As in life the Sun still rises and sets, days will pass by, tears will dry, life will go on...Over the last few days, I have kept myself busy as I can to keep my mind off of Jack. It is hard not to think of him to sense him and to want to be held by him. He was my first love now that I live as a trans...

Texas Hold Him Ch. 03

by jthunderbolt on Sep 15, 2017
BDSM

Showering and shaving took a long time, but Audrey helped me get completely smooth everywhere. Feeling her hands between my legs, shaving around my balls and ass, was almost enough to make me cum by itself. On her advice, I used plenty of moisturizer on my newly bare skin. Our minds were still reeling from the excitement we'd been through and the anticipatio...

Emily's Summer Vacation

by David Phillips on Sep 12, 2017
Anal

(Part Two of The Brat's New Roller Skates) Eighteen year old Emily White was the only daughter to her small town's widower Baptist minister. This small riverside community was dull, at best. Especially now as the Depression sunk even lower, many people were forced to live as migrant workers leaving the town feeling a little deserted. Emily was a tom-boy at...

Oddball Ch. 02

by JimBob44 on Sep 12, 2017
First Time

*Author's Note: Any persons Engaging in any sexual activity are at least eighteen years of age. Chapter 1 'Crack this shell and bring me home,' autumn's 'Shadow Girl' poured out of the speakers and Mary Farmer sang along with it. Thomas looked over and smiled at her and she blushed and looked away, embarrassed. He wondered what she would do if he leaned o...

The Dividing Line

by Adrian Leverkuhn on Sep 16, 2017
Romance

Part I May 10th Sara Wood kept to the shadows, tried to blend in; failing that she would simply disappear into the nameless warrens of the city. Sara Wood was an expert on urban camouflage, at falling through the cracks in whatever systems there were left to deal with girls like her. There was no home for Sara Wood, there never had been. There had been fos...

Letter From Shana

by JamesxPendergrass on Sep 13, 2017
BDSM

Letter From Shana By James Pendergrass – Copyright James X. Pendergrass 2012 Hello, My name is Shana. I'm a 32-year-old, happily married suburban woman. This is the story of how my marriage came to be the way it is. Let's start with the basics. I come from an upper middle class family. I'm white, hold a master's degree, and am a marketing director at a...

They Are A-OK Ch. 19

by fantasyhunter2 on Sep 14, 2017
Group Sex

Note: This story depicts a group sexual scene that includes male to male contact. * I returned home to many surprises. The first was being met on the tarmac by a uniformed man. Instead of a long walk through the terminal, he took me in a golf cart like vehicle to a private parking lot where he had a limo waiting. I was quickly learning that the world was a...

A Couple of Similar Likes Ch. 05

by slave_william on Sep 25, 2017
BDSM

Please note that this and my other works are mainly fantasy and should not be read by those not into heavy BDSM. This is the first of the new "slave william and slave michelle" adventures. Some scenes are close to reality that I have experienced and all are others are ones that I would like to experience first hand. If you dislike my writings, please be matu...