Crossdressing Interactive Stories

1,783 results
Orientation
Length
Source
Infinite Scroll

The College Hottie: INTERACTIVE

by System32 on Dec 19, 2010
Erotic Couplings

Consider the following adventure more as an interactive game rather than a story. In order for this to work, you will need to visit the following URL: http://www.wizards.com/dnd/dice/dice.htm When instructed, you will be required to roll 1 x D100 die to find out what happens to your character. All my stories will work in the same way. You are 19 year old...

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Death By Fucking Ch. 21

by thebullet on Sep 14, 2017
Romance

Chapter 21: Interactive Love Deirdre’s Story Our little girl has changed our lives. Something – hypnotism, magic, psychic brain surgery – has moved our relationship to a place we never knew existed. It’s what I suspected about our children all along. But I never expected it for my husband or my sister or myself. We long ago had recognized that the childr...

Virtual Sex with Jennifer Anniston

by lenux on Aug 12, 2003
Fan Fiction

Welcome John Doe to "virtual sex with Jennifer Anniston"< you will soon find out for yourself that this is one of the most detailed and descriptive interactive sex scenes you will ever have the privilege to witness. The first ten or so steps of the story are to set up your specific sex scene, out of the options that we provide you. The first opt...

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Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Eliminated CYOA

by Deathcon on Apr 3, 2021
Fetish

It was a seemingly normal day in my life, when I heard a banging on my door. Not expecting any visitors, I go to look through the peephole at who it could be. But instead, I simply open the door! Gasping at my bodies incorrect action, a tall woman in robes brushes past my stock still form, into my house and beyond. Picking my jaw up off the floor, I slam the...

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Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......