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.

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 (478) 134304 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 (220) 71697 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) 1091 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.

8.6 (84) 8070 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) 15307 8 Min Comments

Sandwich

By bibilly 23 May 2014

2 bi men and wife share each other.

7.1 (19) 5540 4 Min Comments

Ernestine

By Habu 30 Apr 2014

Drawn into the world of interracial beauty contest transvestites.

8.3 (44) 3433 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) 467 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 (277) 54428 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) 4793 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) 18511 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) 6572 4 Min Comments

Kenny (ch. 2)

By wetpants 19 Oct 2012

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

9.3 (12) 1456 135 Min Comments

Kenny

By wetpants 17 Oct 2012

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

8.9 (14) 2506 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) 14597 7 Min Comments

The Bonus

By Habu 8 Aug 2012

Blowing bonus money on a secret trip to Key West.

7.4 (13) 1726 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) 30718 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) 3269 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) 3980 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) 1373 5 Min Comments

Suddenly I Realized I Wanted This

By Larry 2 Nov 2011

I finally found my true self.

7.2 (14) 3352 6 Min Comments

Chink in the Armor

By Habu 12 Oct 2011

Looking for that strategic piece of countering campaign ammo.

6.5 (16) 2366 13 Min Comments

Career Guidance

By Habu 28 Sep 2011

Reining in a young actor gone off character.

8.2 (21) 3980 11 Min Comments

Preparation

By Larry 20 Sep 2011

How my lover Nephew prepared for me.

6.9 (11) 3207 6 Min Comments

Scared Stiff

By Larry 31 Aug 2011

Extreme Voyerism at its best.

5.6 (5) 2198 5 Min Comments

The Redhead Caper

By Jack Sofelot 12 Aug 2011

Private Dick is caught up in a murder mystery.

9.0 (153) 3359 30 Min Comments

Our most exciting day

By Larry 1 Aug 2011

The day I learned about a crossdressing lover.

8.0 (17) 2933 6 Min Comments

I try to be straight but gay men can tell somehow

By Larry 30 May 2011

A series of true gay relationships where gay men know I love other men

7.1 (10) 2481 6 Min Comments

Coming to Savannah

By Habu 14 Feb 2011

Author struggles to find love anew in Savannah.

8.8 (35) 6234 20 Min Comments

A Night on the Town

By Henry Giles 31 Aug 2010

A crossdresser meets his crush on vacation, and it turns out his crush is gay too.

6.7 (107) 27351 3 Min Comments

Forced Entry In Cubicle

By cumfusion 30 Jul 2010

Sequel to: 'Sissy Boy Rectified By Rugby Forward' "OK just relax your ass, this is probably a bit bigger than what you're used to. So all you've got to do is bend down and let it happen boy!"

8.2 (32) 14409 13 Min Comments

Sissy Boy Rectified By Rugby Forward

By cumfusion 23 Jul 2010

I felt a little pain and a wonderful feeling as this huge powerful man came right up inside me. His cock felt really hot and huge. I was overwhelmed by him; it felt like all the power of his beautiful body was right there up my rectum

9.2 (65) 12217 10 Min Comments

Tricked By A Sissie, Now Made Into A Sissy

By sissybrucie 21 Jul 2010

How I was a tough guy, now a panty wearing sissy.

7.2 (165) 32605 3 Min Comments

A Guy Like Danny

By alexcarr 16 Apr 2010

My own true expeience of meeting Danny and...

6.8 (8) 4758 20 Min Comments

Knock on the Door

By alexcarr 16 Apr 2010

Jerry is after his "Fix" again.

6.2 (6) 2942 9 Min Comments