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.

A Trans-Lesbian Montreal Love Affair

By Cari Christi 24 Jun 2009

A Beautiful Boston T-Girl falls for a very beautiful blonde French Montreal "Gal".

8.5 (93) 19457 14 Min Comments

Sperm Detective (ch. 3)

By sleepwalker 1 Apr 2009

Caught in the act by the people we were following.

8.8 (7) 1202 5 Min Comments

Sperm Detective (ch. 2)

By sleepwalker 16 Mar 2009

Man cheating on wife gets a surprise.

8.5 (8) 1945 8 Min Comments

Harry (ch. 2)

By BubbleButtLuvr 18 Feb 2009

A bi sexual muscular college jock with a fetish for women's underwear must submit the sexual desires of a frat full of nerds or have his secret revealed to his girlfriend.

9.4 (27) 9779 22 Min Comments

Preferring To Go Straight

By Kewtieboy 27 Feb 2008

This is about young gay guy and his driving interest in having sex with absolutely straight guys. There are four encounters in this tale.

8.5 (22) 8505 33 Min Comments

Malta Intervention

By Habu 5 Nov 2007

It seemed an arrangement made in heaven, but it proved to be their downfall. Just when Sandy and I thought that our foursome could not get any better, there was a bitter battle royal in the old villa above St. Julian's that we could hear down at the art gallery in the harbor.

6.6 (14) 946 16 Min Comments

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) 11249 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) 19230 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.

8.6 (13) 4856 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) 14682 10 Min Comments

The Ballerina

By Misty Stiles 15 Feb 2007

a submissive crossdresser, into bondage, meets her master.

7.6 (32) 11583 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) 2223 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) 10287 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) 3787 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) 41057 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) 39157 18 Min Comments