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 listed by date.

7.4
461 Votes

The neighbor made me his bitch

Story by mwmalone

25 Jan 2015 126140 Readers comments 10 Min Read

Older neighbor borrows some tools but ends up making me his bitch.

Topics: Anal Sex, Crossdressing, Chastity, Big Dick, Spanking, Neighbour, Sissy, Face Fuck

8.7
195 Votes

Sissy slut Gangbanged hard and put up wet

Story by mwmalone

22 Dec 2014 60503 Readers comments 13 Min Read

Total fantasy of mine to be used by several men, even though this has not cum true I hope it will one day.

Topics: Anal Sex, Crossdressing, DP, Chastity, Dildo, Big Dick, Spanking, Group Sex, Slut, Sissy, Face Fuck, Big Balls, Gangbang

8.6
19 Votes

Adventure (ch. 8)

Story by Joe Wilson

28 Oct 2014 1026 Readers comments 16 Min Read

Chapter 8, the story about a young gay male coming out in New Orleans.

Topics: Black Men, Anal Sex, Crossdressing, Poppers

9.3
15 Votes

The B'anati

Story by Daddy

22 Oct 2014 2718 Readers comments 140 Min Read

An Alien, the B'anati, has been on Earth for centuries, going from body to body to bring back information to Its home planet. In Its final leave, It becomes a part of a self-absorbed, hedonistic young man whose life, and the lives of many of those around him, becomes incredibly changed.

Topics: Black Men, Latin Men, Anal Sex, Crossdressing, Big Dick, Leather, Sloppy Hole, Cum, Sci-Fi, Big Balls, Oral & Blowjobs, Aliens

8.5
79 Votes

Shipping Dock Raunch

Story by Joe Wilson

27 Sep 2014 6257 Readers comments 16 Min Read

That summer, my Uncle Fred got me a job working on the shipping docks of his company. Not the kind of job a sissy-boy would like, but Uncle Fred said it would make a man of me. Shit! I hated it.....that is, until I saw Ralph, the guy who ran the freight elevator.

Topics: Piss, Black Men, Anal Sex, Crossdressing, Big Dick, Uncle, Interracial

7.1
19 Votes

Sandwich

Story by bibilly

23 May 2014 5072 Readers comments 3 Min Read

2 bi men and wife share each other.

Topics: Anal Sex, Crossdressing

8.3
44 Votes

Ernestine

Story by Habu

30 Apr 2014 3273 Readers comments 10 Min Read

Drawn into the world of interracial beauty contest transvestites.

Topics: Black Men, Crossdressing, Transgender, Interracial, Oral & Blowjobs

8.1
7 Votes

The Desires Of A Witch (ch. 8)

Story by KiddContortion

17 Mar 2014 429 Readers comments 9 Min Read

While Miguel and the gang come to a conclusion about Melody's problem, things start getting steamy for Mr. Satner

Topics: Latin Men, Crossdressing, Fantasy, Witch

7.5
21 Votes

Shear black stockings

Story by CindyUSA

16 Oct 2013 4376 Readers comments 9 Min Read

I love to dress for the pleasure of others,and I post messages on the internet to find dates.

Topics: Crossdressing, Transgender, Oral & Blowjobs

7.1
105 Votes

Bait and switched

Story by CindyUSA

14 Feb 2013 18233 Readers comments 4 Min Read

Someone found out I like to cross-dress and that I was looking for a tubed preamp. I receive a reply to my ad for a preamp not knowing that I have been invited over for more.

Topics: Anal Sex, Crossdressing, Group Sex

8.0
39 Votes

Special help at a second hand clothing store

Story by CindyUSA

14 Feb 2013 6117 Readers comments 4 Min Read

I met a fellow cross-dresser on line. We agreed to meet at a used clothing store where he worked. He said he had a few outfits and offered to help me try them on.

Topics: Crossdressing, Sissy, Face Fuck, Oral & Blowjobs

9.3
12 Votes

Kenny (ch. 2)

Story by wetpants

19 Oct 2012 1229 Readers comments 130 Min Read

What happened next.....and what happened to Kenny afterwards.

Topics: Black Men, Asian Men, Anal Sex, Crossdressing, Oral & Blowjobs

8.9
14 Votes

Kenny

Story by wetpants

17 Oct 2012 2080 Readers comments 102 Min Read

A rentboy approaches a prospective trick, and his life changes forever....

Topics: Anal Sex, Crossdressing, Prostitution, Cum, Bareback, Rentboy

8.0
96 Votes

Loving my black teen daddy

Story by Maikol

26 Sep 2012 18665 Readers comments 7 Min Read

A Latino sissy faggot's hot weekend with her black teen daddy.

Topics: Black Men, Latin Men, Anal Sex, Crossdressing, Big Dick, Daddy, Sissy, Oral & Blowjobs

7.8
74 Votes

A Lesson In Revenge

Story by mouseytwink

20 Aug 2012 14406 Readers comments 7 Min Read

A young guy in a mundane relationship seeks out secret fun, but it comes at a price. A price he is going to have to pay.

Topics: Crossdressing, Spanking, Bisexual, Revenge, Virgin

7.4
13 Votes

The Bonus

Story by Habu

8 Aug 2012 1630 Readers comments 23 Min Read

Blowing bonus money on a secret trip to Key West.

Topics: Arab, Anal Sex, Crossdressing, Rimming

8.0
127 Votes

almost a daily event

Story by craig

2 Jul 2012 30011 Readers comments 9 Min Read

Ive told my story before about being feminized and used by older gay men, now this is what i do and how i do it on a almost daily basis.

Topics: Anal Sex, Crossdressing, Big Dick, Group Sex, Slut, Cum

8.3
10 Votes

Barbed Wire Mansion (ch. 2)

Story by FanGirlGronym

11 May 2012 3130 Readers comments 21 Min Read

This is SBB (Slave Boy Bunny) Revised, REedited, and Redone! Hope you like it!

Topics: Crossdressing, Werewolf, Twink, Master & Slave

7.5
14 Votes

I did not know I had a disorder

Story by CindyUSA

26 Mar 2012 3635 Readers comments 15 Min Read

Roger is bi and likes to meet strangers to give them head. Ray is traveling and sees Roger post about free head. Ray wants to have a threesome with a She-male and when his plans change, he convinces Roger to wear sissy things.

Topics: Anal Sex, Crossdressing, Threesome, Bisexual, Sissy, Pantyhose, Oral & Blowjobs

7.6
8 Votes

Chasing the feeling!

Story by Larry

13 Jan 2012 1318 Readers comments 5 Min Read

Always searching for the unbridled lust of my first gay relationship.

Topics: Crossdressing, Relationship

6.5
16 Votes

Chink in the Armor

Story by Habu

12 Oct 2011 2315 Readers comments 12 Min Read

Looking for that strategic piece of countering campaign ammo.

Topics: Crossdressing, Transgender

8.2
21 Votes

Career Guidance

Story by Habu

28 Sep 2011 3826 Readers comments 11 Min Read

Reining in a young actor gone off character.

Topics: Anal Sex, Crossdressing, CBT, Master & Slave

6.9
11 Votes

Preparation

Story by Larry

20 Sep 2011 3052 Readers comments 6 Min Read

How my lover Nephew prepared for me.

Topics: Anal Sex, Crossdressing, Big Dick, Spanking, Masturbation, Oral & Blowjobs

4.0
3 Votes

Scared Stiff

Story by Larry

31 Aug 2011 2077 Readers comments 4 Min Read

Extreme Voyerism at its best.

Topics: Crossdressing, First Time

9.0
151 Votes

The Redhead Caper

Story by Jack Sofelot

12 Aug 2011 3269 Readers comments 29 Min Read

Private Dick is caught up in a murder mystery.

Topics: Crossdressing, Big Dick, Mystery & Crime, Big Balls, Oral & Blowjobs, Redhead

8.0
17 Votes

Our most exciting day

Story by Larry

1 Aug 2011 2694 Readers comments 6 Min Read

The day I learned about a crossdressing lover.

Topics: Anal Sex, Crossdressing