Gay Crossdressing Stories

GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.

Cross Dresser New Sex Friend

By gila Louieville 4 Jul 2014

The guy and sex fun dressed like a girl.

8.3 (63) 14569 8 Min Comments

Sandwich

By bibilly 23 May 2014

2 bi men and wife share each other.

7.1 (19) 5222 4 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 (270) 51641 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) 4499 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 (105) 18320 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 (41) 6269 4 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 (127) 30255 9 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.

7.5 (14) 3755 16 Min Comments

Our most exciting day

By Larry 1 Aug 2011

The day I learned about a crossdressing lover.

8.0 (17) 2769 6 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) 27193 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!"

8.1 (31) 13598 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 (61) 11514 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.

7.1 (156) 30851 3 Min Comments

Becoming a Sissyboy

By Maikol 1 Mar 2010

I try pantyhose for the first time, enjoy it, get my buddy Corey to enjoy it too and we become sissy buddies.

7.7 (402) 57804 5 Min Comments

My New Pretty Sissy-boi James (ch. 2)

By Maikol 1 Mar 2010

James comes over for pictures and money again and I get the surprise of my life!

8.9 (53) 8916 5 Min Comments

Sissy Gets A Drilling at the Army Camp

By cumfusion 22 Feb 2010

"He's oozing fuck out his ass! Look Don, Cyril must have given him one hell of a stuffing!" Jeff had his fingers in my crack and I just lay there .....

8.4 (29) 14072 20 Min Comments

Turned into a Mexican Master's Sissyboy Cockslave

By saltlakecockslave 24 Aug 2009

A young man is forced into a interracial role as a sissyboy for a Mexican Master!

6.9 (67) 20526 7 Min Comments

My First Trip Out of the Closet (ch. 2)

By Jo 15 Apr 2008

I knelt on the bed and lowered my face to her wet, stretched womanhood. I stuck out my tongue and licked the outside clean before digging in for the "REAL" thing. It was delicious.

8.2 (32) 3684 11 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 (19) 7984 33 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.

7.7 (58) 17793 24 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 (47) 13987 10 Min Comments

The Ballerina

By Misty Stiles 15 Feb 2007

a submissive crossdresser, into bondage, meets her master.

7.4 (30) 10605 10 Min Comments