Crossdresser Stories Stories

58,858 results
Orientation
Length
Source
Infinite Scroll

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

My First Crossdresser Pt. 01

by Princess_Rebecca1991 on Nov 26, 2017
Transsexuals & Crossdressers

Tempting, isn't it? Being in a room or just being aware of there are drawers filled with lovely, feminine underwear. The kind of feminine garments you have dreamed of wearing for sometime, your fantasy you've longed to make a reality. How could a pair be noticed missing? There are so many and they wouldn't suspect you, not the straight going masculine male t...

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...

Your inner femboy

by SkirtSkirt on Feb 10, 2021
Transsexual

The first thing you have to ask yourself is, who are you Are you an ignorant boy about to be turned into a little cum slut?But then who was there to show you who you really are?Or did you do it to yourself? Or are you already a cum dumpster about to reveal themselves? Or maybe you want to be a slutty crossdresser that's secret gets exposed,one throat fuck at...

Open in Reader

Interactive Crossdresser...Dare Me Ch. 02

by PorscheKaru on Sep 16, 2017
Transsexuals & Crossdressers

Hi Porsche I loved your kinky stories and I think its hot how you let strangers tell you what to do. I would like to hear you do something more humiliating though... Are you ready? I dare you... to dress as a hot woman, very high heels, fishnets, tits on, makeup, but with a very short mini skirt and no panties. I want you to get a dog collar and a lead...

Sarah Had to Give a Blowjob

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ---------------------------- After collage, my girlfriend's best friend, Alison, and I found ourselves working in the same city and...

Finally a Princess Pt. 01

by fireandlace0533 on Sep 14, 2020
Transgender & Crossdressers

The first part, of what will be a multi part story, of a crossdresser who loves Disney getting to step out of the closet. I like to develop the characters so if you are hoping to get straight the sex you will likely be disappointed. Finally a Princess (Part 1) You could feel the excitement on the bus as it traveled along the highway. The video showed a bun...

Going Gurly Ch. 01: Cara's Clitty

by anna_subCD on Sep 16, 2017
Transsexuals & Crossdressers

My stories are all true recollections of events from my life, as accurately as I can remember them, with two exceptions: 1. The names of my partners have been changed for their privacy; and 2. I have omitted any references to safe sex, because reading about people fiddling about with condoms is not to my mind very sexy, and in stories you don't need to be...

My Life in High Heels Ch. 07

by cdandie on Sep 14, 2017
Transsexuals & Crossdressers

Hi all! I haven't written in some time as I have been soooo busy. Career, life, new relationships. I'm not going to elaborate on these as all are works in progress but I get so many requests for more stories about things that have happened to me so I thought I would indulge and try to recall an event or two here. Hope everyone enjoys. :) ***** My favorite...

Cheating

by twizted77 on Dec 26, 2018
Cheating Spouses

You never thought it would happen, but here you are after years of marriage, waiting quietly at a dark table in the corner of a hotel bar to meet someone you'd connected with online. Someone who, if things went well, you would be having sex with later tonight. You take a shot of tequila and breath deeply. It burns, but you barely feel it. You are a mixture o...

Open in Reader