Gay Crossdresser Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressing up as women and gay sex with transvestites and crossdressers.

My First Trip Out of the Closet

By Jo 23 Oct 2007

As I young man, a friend introduced me to the joys of cross dressing. This is the story of what occured that eventfull weekend.

8.6 (53) 11223 16 Min Comments

Misty the slave

By Misty Stiles 29 Jun 2007

Misty a crossdresser is taken by by a man and forced to serve him as his slave.

7.6 (60) 19118 24 Min Comments

My Best TV Encounter

By Janice 25 May 2007

While I was crouched down, I'd flipped the top off a tube of KY jelly and smeared a good dollop on and up my arse. I wanted a good wet slippery fuck, didn't I? I stood up. He slipped a condom over his knob, showing me what he was doing. I went down again and rolled it on with my lips.

8.9 (11) 4820 7 Min Comments

Finally Fucked

By Willing 6 Apr 2007

He did it. He fucked me for a half hour, more, both of us using the poppers. Finally I felt his cock swell, throb, lurch, jerk, and the condom filling with his cum.

8.2 (50) 14620 10 Min Comments

The Ballerina

By Misty Stiles 15 Feb 2007

a submissive crossdresser, into bondage, meets her master.

7.6 (32) 11485 10 Min Comments

Living with Libby (ch. 2)

By Kewtieboy 12 Dec 2006

My girlfriend is hot for a guy who is is gay and comes up with a novel way of having sex with him.

8.1 (12) 2210 10 Min Comments

Cross My Heart

By David Solomon 8 Dec 2006

Eric thought he knew his best buddy. But then, Trevor thought he knew his whole circle of friends!

9.3 (30) 10271 55 Min Comments

Sex in Stilettos

By AnonymousMan 12 Oct 2006

I knew exactly what she meant. I removed her shoes by gripping the heels between my teeth, then made love to her silk stockinged feet with my mouth. Though she retained her tight grip on my hair, she did not manipulate me in any particular direction.

8.7 (13) 3773 17 Min Comments

2 Girls Out for a Night on the Town

By Pat Sizer 11 Oct 2006

Brittany winks over his head at me, as she starts kissing him passionately. His hands quickly found their way into my bra. He was squeezing my tits and fondling them as Brittany sucked on his tongue and felt up and down his chest.

6.7 (148) 41039 4 Min Comments

A Girl Called Eddie

By Pat Sizer 11 Oct 2006

My challenge went unfinished as he practically leaped upon me, pinning me to the wall and silencing me with a lip-crushing kiss. While his tongue filled my mouth, his hands clawed frenziedly at my dress, wrenching it up over my hips.

7.4 (122) 39127 18 Min Comments