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.

Ana Le Babe - Becoming A Cross Dresser

By Ana Le Babe 21 Nov 2015

This story is how my alter ego, Ana Le Babe, came into being. This and following stories relate the encounters she has had (both sexual and general), and are all true. In writing this, I hope to help others in a similar situation deal with their feelings and stimulate those that are interested in our way of life.

7.5 (62) 10717 9 Min Comments

The clients

By Angie K 16 Oct 2015

Fun with a wife and her cross-dressing husband

8.2 (36) 4796 4 Min Comments

Truck Stop Encounter (ch. 2)

By bud C 12 Oct 2015

fun at the truck stop

9.0 (77) 5973 21 Min Comments

Truck Stop Encounter

By bud C 9 Oct 2015

Fun at the truckstop

8.9 (77) 11049 28 Min Comments

Painting Donovan (ch. 4)

By DSDS 18 Sep 2015

Alright, so I decided it was unfair to end this series on a cliffhanger. If you read this and want more, say something.

9.0 (69) 1740 16 Min Comments

My first BBC

By mwmalone 31 Aug 2015

A true story of my first BBC and being his crossdressing slut

8.1 (101) 27783 9 Min Comments

MY First Cross-dress experience: Simply Awesome

By sunny 21 Jul 2015

My first crossdressing story

7.2 (33) 10172 7 Min Comments

Noah Flip Flop

By Habu 20 Jul 2015

American college student traveling South Seas on winter holiday hooks up with Australian street musician in Sydney

9.1 (46) 2309 17 Min Comments

Blue Dragon

By Habu 13 Jul 2015

Small town Ohio café waiter Casey dreams of escaping and finding sexual adventure.

8.0 (50) 2814 9 Min Comments

Tennis Interview

By Habu 25 May 2015

Why would a tennis pro base in Bangkok?

8.9 (37) 1592 17 Min Comments

The sissy within me The Transformation from boy to Daddies sissy

By Ed 27 Apr 2015

Justin is slowly transformed into a sissy by his new daddy

7.2 (124) 37903 6 Min Comments

While the cats away, I get to play

By mwmalone 4 Apr 2015

A fantasy of becoming a black mans sissy slut but hope it cums true someday

7.9 (46) 8566 14 Min Comments

The sissy within me

By Ed 23 Mar 2015

This straight acting boy/guy has a sissy hidden inside him and is found out about by a friend who transforms him into the true sissy he wants to be.

7.5 (145) 50097 6 Min Comments

wow

By charles-smythe 23 Mar 2015

glory hole suck

8.7 (57) 4027 9 Min Comments

Decoy

By Habu 17 Mar 2015

Arab subterfuge played out a Washington, D.C., pro men's tennis tournament.

8.7 (42) 2063 16 Min Comments

The neighbor made me his bitch

By mwmalone 25 Jan 2015

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

7.5 (477) 132799 10 Min Comments

Sissy slut Gangbanged hard and put up wet

By mwmalone 22 Dec 2014

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

8.8 (215) 69730 13 Min Comments

Adventure (ch. 8)

By Joe Wilson 28 Oct 2014

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

8.6 (19) 1087 17 Min Comments

Shipping Dock Raunch

By Joe Wilson 27 Sep 2014

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.

8.5 (82) 7788 17 Min Comments

Cross Dresser New Sex Friend

By gila Louieville 4 Jul 2014

The guy and sex fun dressed like a girl.

8.3 (64) 15029 8 Min Comments

Sandwich

By bibilly 23 May 2014

2 bi men and wife share each other.

7.1 (19) 5437 4 Min Comments

Ernestine

By Habu 30 Apr 2014

Drawn into the world of interracial beauty contest transvestites.

8.3 (44) 3410 11 Min Comments

The Desires Of A Witch (ch. 8)

By KiddContortion 17 Mar 2014

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

8.1 (7) 461 9 Min Comments

CD goes to a adult theater for some action

By CindyUSA 16 Oct 2013

A CD goes to a adult theater to get used.

8.2 (274) 53753 8 Min Comments

Shear black stockings

By CindyUSA 16 Oct 2013

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

7.4 (22) 4683 9 Min Comments

Bait and switched

By CindyUSA 14 Feb 2013

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.

7.1 (107) 18470 4 Min Comments

Special help at a second hand clothing store

By CindyUSA 14 Feb 2013

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.

8.0 (42) 6497 4 Min Comments

Kenny (ch. 2)

By wetpants 19 Oct 2012

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

9.3 (12) 1410 135 Min Comments

Kenny

By wetpants 17 Oct 2012

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

8.9 (14) 2444 107 Min Comments

A Lesson In Revenge

By mouseytwink 20 Aug 2012

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.

7.8 (75) 14562 7 Min Comments

The Bonus

By Habu 8 Aug 2012

Blowing bonus money on a secret trip to Key West.

7.4 (13) 1711 24 Min Comments

almost a daily event

By craig 2 Jul 2012

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.

8.0 (128) 30613 9 Min Comments

Barbed Wire Mansion (ch. 2)

By FanGirlGronym 11 May 2012

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

8.3 (10) 3236 22 Min Comments

I did not know I had a disorder

By CindyUSA 26 Mar 2012

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.

7.4 (15) 3933 16 Min Comments

Chasing the feeling!

By Larry 13 Jan 2012

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

7.6 (8) 1364 5 Min Comments