Crossdressing Sex Stories

224,832 results
Orientation
Length
Source
Infinite Scroll

Best Camping Trip Ever Ch. 04

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

*This is a work of fiction. Most of my stories are true, but I do have unrealized fantasies...that I'll try to make reality...hope you enjoy!* *Note-this is part four of my story entitled 'Best camping trip ever for CD'...if you haven't read the first three parts, or at least part two and three, you won't understand what's going on at first. I don't like to...

Life and Time of Lady Vargos Ch. 18

by rik581 on May 21, 2019
Transgender & Crossdressers

Chapter 18 "Changes upon Changes" Martin rolled over on his side hugging his pillow trying desperately to fall asleep. Though the curlers that Leanne had tightly wound in his hair for the night were very uncomfortable and trying to position his head to sleep in them was exhausting, it was the events of the day weighed heavily on his mind and kept him awake...

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...

The Bio of a Masturbator

by Chatomana on Sep 18, 2017
Toys & Masturbation

Disclaimer: Although this is a work of fiction, some parts contain actual facts and events. The author can not and will not be held responsible for any injuries that may occur if the reader tries to reproduce of these events. The author holds all copyrights to this story, printed and/or digital. Prologue This story is not about love, nor about romance, or...

Sarah Was Caught Masturbating

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

After collage, my girlfriend's best friend and I found ourselves working in the same town and so we decided to share an apartment. Her boyfriend had another year to go in college and my girlfriend worked in a different city. I loved living with her; we became the best of friends; just friends but very close. We cooked together every evening and watched TV....

Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

Escapism: The Modern Man

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

*Synopsis: 25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. Sick of his friends and routine, Alex accidentally reawakens feelings he has not had for a long time. Think Trainspotting for sissies - American Psycho without the violence and lot more lace, lip-gloss and high heels.* ESCAPISM:...

With Her Blessing

by komrad1156 on Sep 12, 2017
Transsexuals & Crossdressers

"Hello again, Kyleigh!" he said as he looked at himself in the mirror after carefully pulling on his very expensive human-hair wig. Ky Finley was now Kyleigh Finlay and she felt this wonderful rush of endorphins flood over her as she looked at the beautiful creature she'd become over the last ninety minutes. Ky had sandy blond hair so Kyleigh could easily b...

Stacy and Matt

by mattpantyhose on Jan 28, 2020
Fetish

Matt's bliss ended almost as soon as it had begun. The girl he had met and who not only was pretty and smart, but also enjoyed his crossdressing decided that career was her priority after merely few weeks of their relationship; the two broke up as she moved to a different distant city. Matt still had a good job, amazing boss and sympathetic co-workers, but d...

Gender Change: Magic Closet

by Zekar on Jan 26, 2017
Fantasy

There is magic in the world. Narnia was just the tip of the iceberg when it comes to the magic that a wardrobe or closet can do. You find yourself directly in the crosshairs of such a magical encounter. Whether malicious or benevolent, that is up to you... This is merely the introduction to a much more interesting tale. (Dear reader, if you like this story a...

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