Sissy Contract Stories

32,406 results
Orientation
Length
Source
Infinite Scroll

Caught Red Handed

by desireethtttv on Sep 15, 2017
Transsexuals & Crossdressers

With Halloween falling on a Monday, my wife Suzie was busy the weekend before trying to find her costume to wear to work. As a dutiful sissy husband that loves shopping as much as any woman, I tagged along, although our choice of stores to peruse is completely opposite. Suzie is a Goodwill addict, with anything at a bargain giving her much pleasure. Me, I'd...

You Can Always Say No Ch. 07

by AngelCherysse on Sep 25, 2017
Transsexuals & Crossdressers

She awoke slowly, just as I had that morning. I gazed down longingly at her figure, still seductively attired in corset, stockings and heels, as she knelt before me on the coffee table. Her face rested to one side on the tabletop. I strolled slowly around the table, allowing her to drink in the sight of my body, tightly corseted in black calfskin with my bre...

Coming Home, Coming Out Pt. 09

by EiryCGar on Jun 1, 2020
BDSM

Author's note. As this saga continues, aspects of sadism, slavery, cuckoldry, lesbianism, denial and general bdsm are explored. All characters are figments of the author's imagination, and all characters consent to every aspect of the activities described. As always, all characters are aged over 18. Chapter nine. Saturday morning dawned, and Sara slipped f...

Dominating Ken Pt. 09-10

by oneguy4fun on Sep 26, 2017
BDSM

PART 9: THE POWER OF THREE Kimmee's (Ken's) heels clicked across the marble floor of the hotel lobby. He was in a hurry to go nowhere. He figured if he walked fast enough no one would notice the secret underneath the feminine facade. Mistress Kareena had done such a fabulous job at hiding his masculinity and highlighting his feminine qualities that someone...

Twist

by Seurat on Sep 12, 2017
BDSM

Once, long ago, I got fed up with the way femdom, forced transgender, and loving wife stories with BDSM basis ended; they had grown very predictable. In fact, a few authors had posted short lists of vignettes which, unintentionally, encompassed all of the common endings which I had grown to abhor. My own list, a response to the predictability of those storie...

The Vacation from Hell Pt. 01

by JamesMiehoff on Nov 27, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

A Game within a Game Ch. 02D

by doberinca on Sep 16, 2017
Transsexuals & Crossdressers

Author's Note: This is the second story. I still have sometimes trouble to find the right syntax. I hope you still have fun in reading this second story. A third will be following. The characters involved will appear more 'human', not real good and not real bad, and make sometimes bad decisions. Chapter 2D. Another session - or not. The next morning...

Caught in Her Panties Ch. 03

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

As we walk down the street I wink at some of the men walking past us. Alex and Mary giggle as they see the men checking me out. I even smile at the women too. "You are such a tease Krystal!" Alex says noticing some of the women blush as I check them out. We find a nice sidewalk coffee shop and take out seats. As I sit, I feel someone smack my ass. I jump a...

Craig's New Life

by Sweet0ne on Sep 26, 2017
Transsexuals & Crossdressers

I couldn't believe my luck. The woman interviewing me was the sexiest creature I had ever encountered. Long, silky, black hair framed a perfect face with piercing gray eyes and luscious ruby lips. I'd done more than my share of womanizing over the years, but I'd never conquered a female quite like this. Even in her conservative business attire she radiated...

Allyson's First Blowjob

by sissymaidallyson on Sep 16, 2017
Transsexuals & Crossdressers

I have been a closet cross dresser for many years. A few people knew but it wasn't well known and that is how I liked it. I enjoyed dressing up and prancing around my flat in ladies clothing but I always had fantasies about going further. I kept stopping myself from doing anything further but there was that burning desire to be truly slutty inside of me. On...