Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

Mother in Law's Suitcase Ch. 09

by sethwaite on Sep 23, 2019
Fetish

Authors Note: This story contains scenes of incest or incest content, please do not continue if that offends you. ***** Saturday morning arrived and I was awake early. I had already showered and dressed before Sarah was out of bed, my mind racing at the possibilities that the day ahead held. I was sitting in the kitchen enjoying a coffee and reading the p...

Mad Women: Hiring Interns

by galitea on Mar 16, 2020
Transgender & Crossdressers

Mad Women: A Futa Story Hiring the Interns It was barely 11 AM and already there was a large group of people gathered in the center of the office. In fact, it seemed to be just about everyone who worked in the office gathered around in a circle. The women of the marketing agency were all pushing and prodding each other to get the best view of the action....

The Robertson's Sissy Ch. 04

by Clite69 on Aug 6, 2019
Transgender & Crossdressers

**A quick note. The chapters of this story can fall into multiple categories, group sex, reluctance/nonconsent and transgender/crossdresser. If any of these are not your taste than this story may not be for you.** ***** I woke the next morning almost forgetting where I was before realizing I was still at the Robertson's. I layed there in bed, still dressed...

Chains Willing Ch. 01

by Radiantlies5 on Oct 24, 2018
Sci-Fi & Fantasy

Chapter One: Illiana ...Or Liana for short. Regardless, when I woke up it seemed as if my life was about to end. So, my name didn't matter anymore. Not that anyone cared, that is. My vision returned with a headache and sudden rush of other feelings. My arms were over my head and bound by leather straps chains that led to a hook on a post. I began to hyperve...

Role Playing With Kirsten

by Just Plain Bob on Dec 24, 2019
Loving Wives

A story by Just Plain Bob I suppose you could say that I was na‹ve and maybe even that I should have seen it coming, but I didn't. It just happened. I thought that I was strengthening my marriage when actually what I was doing was weakening the fabric that would eventually let it disintegrate. +++++++++++++++++++++++++++++++++++++++ It started innocently...

Working the Holidays

by es_larsson on Dec 10, 2019
Transgender & Crossdressers

I negotiated my way through the packed crowd of shoppers and wheeled the trolley towards the stockroom doors. "It's mental out here." Kareem glanced over and raised his eyebrows in greeting. "Christmas rush - you know how it is." Kareem was the security guard in the store, and had been for 25 years. He was about 6' 2 and had the physique of a rugby playe...

Sexy Mandy and Nikki Buy a Car

by BAD BOY BILL on Jul 14, 2020
Interracial Love

On a warm Friday afternoon, Jake "Action Jackson" Baxter stalked like a tiger pacing his cage. Jake was ready to sell a new car to every customer who walked through the showroom door; positive they would leave with a set of keys and a stiff monthly payment and a smile on their face. Jake was the top dog at Costa Mesa BMW. He knew it, the owner knew it, an...

Coming Home, Coming Out Pt. 06

by EiryCGar on Apr 13, 2020
BDSM

Author's note: The events described in this chapter occur roughly ten years before the events in chapter five. They include cuckolding, enforced chastity, BDSM, sexual denial, submission incest and smoking. All characters are fictitious, aged over 18, and all activities described are consensual. Chapter 6 The newly qualified Dr Mary Walters looked at her...

Bayonetta's Abuse Ch. 10

by ChainedToAKeyboard on Jun 1, 2020
BDSM

Lust, animosity and the will to power! Dangerous forces combine as a showdown looms. Bayonetta's Abuse X - Gathering Storm "Ohhhhhh! OHHHH GOD!!" Moans flowed freely from James' mouth as Bayonetta's fist slurped in and out of his well stretched pucker. It was late morning and although their play session had stretched on for nearly two hours, Mistress s...

Ash's New Career Pt. 03

by Fibaro on Oct 19, 2020
Transgender & Crossdressers

Chapter 4 Sensing Ash's nervousness Jessy took charge upon entering the house. She had the feeling that something wasn't quite right with this shoot, but most of all she wanted to appease Ash a little. "Alright, if you all don't mind I have a lot of work to do and I rather do so quietly, well at first at least. Once I'm ready with the foundations I'll call...