Gay Crossdressing Stories

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

When and How did I start (ch. 2)

By Crossy Arora 26 Jul 2019

How my life changed from imagination to reality

8.3 (22) 3623 2 Min Comments

Dressed for success

By Steve Webb 23 Jul 2019

A friendly tourist gets the surprise of his life. A fantasy

8.2 (60) 6601 6 Min Comments

The birth of Slutty Tanya

By Slutty Tanya 9 Jul 2019

A chance encounter leads an occasional cross-dresser down the path of becoming a full time slut.

7.2 (34) 3928 4 Min Comments

Roommate surprise

By Steve Webb 24 Jun 2019

A horrific moment turns into a dream night

8.4 (85) 11476 5 Min Comments

Cross dressing went too far

By fetishlover 20 May 2019

My love of wearing panties, stockings and tights went too far nad got me into serious trouble...

7.3 (54) 16365 6 Min Comments

My new body modification

By Lingerielover 25 Apr 2019

My mini cock and balls are driving me mad, so I did something about it !!!

8.3 (62) 7818 6 Min Comments

Girly

By bootlicker 22 Apr 2019

A small, weak, submissive man is feminized and abused by a trio of dominant perverts intent on transforming him into their sissy slave gurl.

8.4 (45) 27570 66 Min Comments

Dressed as an Easter Bunny, Fucked like a Rabbit

By Shy Stuart 19 Apr 2019

Me and my gurlie friends go to the local tranny club dressed like Easter Bunnies and get fucked like rabbits

8.4 (37) 8555 5 Min Comments

She turned me out

By Bob Long 13 Mar 2019

My girlfriend not only encouraged my crossdressing but how she turned me into the cock sucking whore I am

8.2 (50) 9401 27 Min Comments

First me then my wife become a black guys bitch (ch. 2)

By Shy Stuart 10 Feb 2019

I bottle out of going into Carlton house and he's not happy. However, a week or so later while in a drunken stupor I give Carlton my address and invite him around to fuck me.

7.6 (76) 14378 4 Min Comments

I was a man this morning, but now?

By fetishlover 20 Jan 2019

Girfriend gets revenge on her man after finding him with a gay guy

7.3 (54) 10356 8 Min Comments

Sissy Hypno Vids ... how I've changed

By need2btakenow 29 Dec 2018

I started watching sissy hypno about 3 years ago. Played with the idea of dressing up as a CD many times growing up and occasionally as an adult. But the fad would pass and go away for years. Not anymore...

8.3 (65) 14124 7 Min Comments

Getting dominated by an 9 inch cock

By Sissy Bitch 27 Dec 2018

Got dominated by a 9 inch cock while i was traveling

6.4 (78) 17357 2 Min Comments

How i became a bitch addicted for cock

By Sissy Bitch 23 Dec 2018

My history on how i became a little bitch that can not live without cock.

7.3 (95) 20052 4 Min Comments

Boy to College Girl

By Sissy Scarlet 29 Nov 2018

Charles has battled against his feminine features all his life. It takes a single experience with a dominant, alpha high school jock in the locker room to make him know his place in the world. ! ARCS Needed !

8.5 (84) 28499 23 Min Comments

I'm a Slutty Cheerleader

By Brett 7 Nov 2018

Daddy wanted to fuck a teen cheerleader and I wanted him to fuck me, so he bought the outfit and I got more than I could have hoped for.

8.5 (79) 15450 8 Min Comments

The making of a sissy

By Jamie Villa 13 Sep 2018

How my fascination with all things femme began

7.0 (68) 8722 3 Min Comments

My Love of Lingerie, carried me away.

By fetishlover 28 Jun 2018

I love wearing lingerie, and my best pal found out and gave me some help

8.2 (41) 9720 8 Min Comments

Sleazy Landlord

By Sissy Scarlet 12 Jun 2018

Jesse has been spending too much of his money on his... hobby. Now rent is due, what ever will he do? :)

7.6 (59) 11353 3 Min Comments

Singapore to Dubai unexpected journey (ch. 3)

By zeenatcd 12 Jun 2018

Razak showed me the heaven during sex and i became his slave.

9.2 (17) 3683 6 Min Comments

Boy to Bride (Feminization Novella)

By Sissy Scarlet 8 Jun 2018

Adam MacDonald secret life of crossdressing has always been both the escape and high of his life. A mysterious package with no sender address arrives one day, and inside it contains: a dress and more!

6.2 (77) 26087 7 Min Comments

A little body modification can be SO beneficial.

By Lingerielover 30 May 2018

I get my balls changed and my cock replaced with a..

7.5 (104) 43490 6 Min Comments

Good Lumberjack, Bad Lumberjack

By Sissy Scarlet 26 May 2018

A foreign loser in his hometown, a boy works at a carnival where he is embarrassed by dehumanizing customers. A charming Alpha finds the boy in tears, comforts him, and the two end up starting a secret relation

7.3 (30) 3524 5 Min Comments

Chrissy's New Life

By sluttybttm4u 17 May 2018

Phillip/Chrissy has been seeking a loving life in the hands of a very loving man

5.4 (20) 5855 2 Min Comments

Homophobe gets feminized (ch. 2)

By Ben Drake 12 May 2018

Richard is given his first lesson and he had better pass.

6.4 (50) 8224 2 Min Comments

Buying tights and panties started a new life......

By fetishlover 11 May 2018

I went to buy new tights and panties, met a guy buying similar and our lives changed for ever!!

7.8 (32) 14200 13 Min Comments

Abandoned Parking Lot (ch. 2)

By Sissy Scarlet 9 May 2018

After fighting with a drunk girlfriend, a boy is fed up with women. He decides to finally live out a fantasy he's had for years.

8.0 (92) 20688 2 Min Comments

Wish I had not worn those lace panties

By Lingerielover 16 Apr 2018

Gay cross dresser wore new lace panties and things suddenly got out of hand!!!

7.7 (39) 13891 12 Min Comments

Sex with my boss honeymoon in Singapore

By zeenatcd 2 Apr 2018

This is a third part of my Singapore honeymoon trip. We enjoyed our best honeymoon night in hotel room.

8.0 (19) 6513 6 Min Comments

strapped in Houston

By knickerlesstina 16 Mar 2018

it was hot in Houston but I was determined to go out on the town that night. I had a red mini dress on with red strappy sandals. Pink Victoria's Secret panties and bra. Long reddish hair and well made up ...

6.8 (29) 3482 5 Min Comments