Crossdress Stories

204 results
Orientation
Length
Source
Infinite Scroll

Michele Nylons' True Stories Ch. 05

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

Wedding Date

by bullockhall on Sep 13, 2017
Transsexuals & Crossdressers

It was friday night, and I was at a sports bar watching college basketball with my best friend, Alan. We'd grown up in the same suburban town and had been friends our whole lives, meeting in kindergarten, and taking the same classes through high school. We did everything together, slept over at each other's houses, double dated, and were like brothers. We...

Inaugural Crossdress Sexfight Ch. 02

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

CXSFL – Match 2: Dani vs Jamie With my first match under my belt, albeit a humiliating lopsided loss, I felt better prepared and even more excited to try another match. I was hoping to be on the giving end for my next match and felt I had learned some valuable lessons that would increase my chances of getting a win. Although it's difficult to complain about...

David and Jess Ch. 04

by TGDIB on Apr 22, 2020
Transgender & Crossdressers

This story is entirely fictitious. All names and likenesses are fabricated, and all characters depicted are over the age of 18. This story is multiple pages / chapters, and involves elements of romance and erotica. ---------------- Chapter Four: I stared in disbelief for a moment, frozen in place as my mind reeled. Surely I must have misheard. Jess's hip...

Magic Panties Ch. 03

by nolfon1 on Sep 12, 2017
Transsexuals & Crossdressers

This story is a work of fiction, all characters are fictional and obviously the events are fake. You may reprint this as needed, just give credit to the author. If any differences occur between continuity, accept the one you like better as truth, and enjoy! * For those just joining us, let me recap, my name is Rachel...er, Roy, yeah let's go with Rachel, a...

My Chastity Story Pt. 01

by Digger66 on Oct 3, 2018
Fetish

[Massive re-write of this story. Good feedback. I flushed out the character's motivations.] * It all started because I jerk off too much. Every night, I would retreat to the basement after my wife, Kate, would go to bed early. Both of us are in our mid-forties. I often asked for sex, but my wife complained that I was never any good at it. She always said t...

Maid to Order Ch. 03

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Michele lay on her bed sobbing. She felt confused and defiled. Michele's alter ego Mick had spent many years in the army, he knew how to fight and would never allow himself to be coerced or forced into doing anything he didn't want to. But when he transformed into Michele, all of his resilience training and self-defence mechanisms seemed to have disappeared...

How I Became Sissy Willow Ch. 02

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

"Now the preliminaries are over, and it's time for the entertainment part of our evening!" That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation. Fer...

Barrack Room Betty Ch. 04

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Four - A Night at the Flicks Michele was confused; she didn't like Leading Recruit Jason Jones one bit, he was a bully but he was also handsome, strong and actually quite intelligent. She knew he had a thing for her as soon as the Leading Recruits made the grommets crossdress, and of course last night he had ejaculated in his pants when he was span...

Inaugural Crossdress Sexfight Ch. 03

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

The third match of the season matched me up against another rookie that shared the same name as me. Dani had read my stories on the internet and enjoyed some of my photos on Flickr and wanted a match with me. I guess it would seem pretty enticing as I'm sure he was noticing that I was seemingly now a jobber. I had seen Dani's photos on Flickr as well and we...