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Crossdressing
Gay Crossdressing Stories
GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.
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By cock whore kimmy 27 Feb 2020
Kim comes home early from work and hears a whore getting fucked in her bedroom. She can only assume her BF Gary is in there cheating on her. So she slips in to catch him in the act, but what she finds in nothing like what she thought. She finds Gary all alone, lying on the bed. He’s wearing some of her sluttiest clothing, and trashiest lingerie. And he’s fucking himself with her favorite dildo.
8.0 (54) 9055 26 Min Comments
By Bob Long 10 Feb 2020
My girlfriend who fostered my obsession with crossdressing and living as a woman, trained and made me into one hell of a beautiful woman who eventually sucked a mans cock and loved it
7.8 (30) 8536 51 Min Comments
By Bob Long 4 Feb 2020
This is a continuation of my glorious introduction to crossdressing and sex
7.8 (6) 2240 23 Min Comments
By Bob Long 1 Feb 2020
This is the story of how my ex girlfriend, made it her mission to get me to suck a guys cock
7.3 (40) 9935 25 Min Comments
By cock whore kimmy 26 Jan 2020
Little CD fuckdoll has his first sissygasm and his life changed forever!
8.5 (49) 10819 3 Min Comments
By SandyCD 6 Jan 2020
Caught by daughter with me dressed as woman
8.7 (85) 15672 12 Min Comments
By Nils Huim 28 Dec 2019
A gay sissy bottom receives a surprise birthday gift
7.8 (16) 10985 10 Min Comments
By Kristen Kross 23 Dec 2019
crossdresser's first time prostituting first timer
8.8 (92) 21569 10 Min Comments
By FishnetSissy 21 Dec 2019
2 blonde bimbos help a little sissy faggot become the girl he always wanted to be and Introduce him to a man who knows just what to do with a special girl like this!
7.8 (72) 34949 29 Min Comments
By Kristen Kross 21 Dec 2019
cd sissy meets her apartment manager
8.7 (67) 6385 9 Min Comments
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By Nils Huim 16 Dec 2019
Two ex-cons have anal & oral sex and then plot (?) a robbery
7.7 (21) 1796 10 Min Comments
By Kristen Kross 7 Dec 2019
CD, girl, and a stranger meet in a motel room
8.7 (16) 2952 25 Min Comments
By Sisyboy 21 Sep 2019
Part 2 of getting caught
7.3 (45) 9566 2 Min Comments
By zeenatcd 14 Sep 2019
My mistress made me her slave and gang banged me with her friend Domino,Alisa and Mariana.
7.8 (11) 4606 6 Min Comments
By Crossy Arora 26 Jul 2019
How my life changed from imagination to reality
8.3 (22) 3707 2 Min Comments
By Steve Webb 23 Jul 2019
A friendly tourist gets the surprise of his life. A fantasy
8.2 (62) 6752 6 Min Comments
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) 4116 4 Min Comments
By Steve Webb 24 Jun 2019
A horrific moment turns into a dream night
8.4 (86) 12200 5 Min Comments
By fetishlover 20 May 2019
My love of wearing panties, stockings and tights went too far nad got me into serious trouble...
7.4 (56) 17052 6 Min Comments
By Lingerielover 25 Apr 2019
My mini cock and balls are driving me mad, so I did something about it !!!
8.3 (63) 8332 6 Min Comments
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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.
8.6 (52) 34087 66 Min Comments
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) 8791 5 Min Comments
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) 10664 27 Min Comments
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.
7.7 (87) 15345 4 Min Comments
By fetishlover 20 Jan 2019
Girfriend gets revenge on her man after finding him with a gay guy
7.4 (55) 10780 8 Min Comments
By Sissy Bitch 27 Dec 2018
Got dominated by a 9 inch cock while i was traveling
6.4 (81) 18318 2 Min Comments
By Sissy Bitch 23 Dec 2018
My history on how i became a little bitch that can not live without cock.
7.3 (97) 21276 4 Min Comments
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 !
8.6 (88) 30044 23 Min Comments
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 (80) 15956 8 Min Comments
By Jamie Villa 13 Sep 2018
How my fascination with all things femme began
7.1 (69) 9313 3 Min Comments
By fetishlover 28 Jun 2018
I love wearing lingerie, and my best pal found out and gave me some help
8.2 (41) 10589 8 Min Comments
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? :)
7.7 (65) 12099 3 Min Comments
By zeenatcd 12 Jun 2018
Razak showed me the heaven during sex and i became his slave.
9.2 (17) 4012 6 Min Comments
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 (82) 28454 7 Min Comments
By Lingerielover 30 May 2018
I get my balls changed and my cock replaced with a..
7.5 (106) 44485 6 Min Comments