Big black sissy Crack whore
By Big Black sissy 9 Jan 2022
My life that i want
Gay Crossdressing Stories
GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.
I'm his bound and gagged girlfriend
By BillyBoy 6 Jan 2022
She told her friends I wanted to wear her underwear and be tied up when we had sex. It was a weak moment for me. I shouldn't have asked her. I was young and didn't know any better. She didn't appreciate my wishes at all. That was it for her, and most any other chance I may have had with a girl. But, she handed me off to someone who did appreciate my fantasy. For better or worse!
After Halloween
By BillyBoy 30 Dec 2021
I wore a girl's dress as a joke to a Halloween party. It was all in fun. Wives and girlfriends were there. But after that, I got a few uncomfortable calls and texts from a few of the men who saw me.
bondage blowjob
By BillyBoy 28 Dec 2021
I woke up in his bedroom, wearing his wife's wedding lingerie. I'm on my knees with his cock in my face. What now?
Santa Rosa Slut
By bootlicker 27 Dec 2021
A young drifter in Palm Springs is taken in and trained as a sissy, a slut, a slave, and a boi-whore by two older men and their friends.
Cross dresser.. Twink.. Tranny?
By djfmonkey 22 Dec 2021
My straight buddy and I visit a gay bar, where we discover our own inner selves, and the truth about each other
Shower Power
By BillyBoy 22 Dec 2021
'Daddy' shaved me in the shower. While the water was pouring over us, he put me in a matching set of rubbery vintage Playtex bra and open bottom girdle panties.
Secret Sissy
By BillyBoy 10 Dec 2021
I've been in the closet all my life. Finally, I have a chance to try out being a sissy girl for a real man
Dreams and Frustration
By BillyBoy 9 Dec 2021
Every day I awake from a dream of being used as a girl whore. I can't stop it. I'm in trouble!
My secret dreams
By BillyBoy 7 Dec 2021
The gay date I'd love to experience. I've had a few gay experiences, but someday a man will make me his little bitch. I'd love that!
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Halloween party
By BillyBoy 2 Dec 2021
I finally let him seduce me. I agree to meet him. He has been flirting and making promises. Then at the last minute, he tells me I'm going to dress like a woman tonight.
Park Slut (ch. 3)
By Alleykat 30 Nov 2021
Turned into the park cocksucker by a fat old man
Park Slut (ch. 3)
By Alleykat 23 Nov 2021
I would go to the park at night letting guys blow me until the fat old man turned me into the cocksucking cumloving slut at the park and at my mom's house.
Now I'm a crossdressing Domme?
By BillyBoy 20 Nov 2021
A shy, submissive guy hits me up to dress like his wife and Domme him. I actually liked it more than I thought I would!
How this straight guy became a sissy bottom
By Somewhat Straight 17 Nov 2021
It took while, but my transformation is complete
Doctors are human too
By BillyBoy 11 Nov 2021
I forgot and wore some panties to my check-up. The doc was surprised. But he responded differently than I expected.
In a short span I became a sissy boy trap (ch. 2)
By Desertbiguy 10 Nov 2021
I had spent all of my time getting indoctrinated in gay sex by Tom G. I forgot about my first man to pop my anal cherry Mark.
Introduction into Gay Domination (ch. 2)
By Anthony 8 Nov 2021
I went to work and tried not to run into Jerry, but that was hard, seemed like Jerry kept looking over at me and would walk by me giving me a look. When no one was around, he would come up to me and show me a picture of me on his phone of me in one of the positions that I was in.
Nanny cam gone bad
By BillyBoy 5 Nov 2021
My wife installed one of those nanny cams. She wanted to see what the dog was doing when we were at work. She didn't tell me. She started watching me dress in her underclothes and tie myself up like a kidnap victim, jerking off. Not sure what to do, she asked a friend to watch the videos. He knew just what to do with me.
Halloween is a great time to express sexual feelings (ch. 2)
By Desertbiguy 4 Nov 2021
Dressed up for jr high halloween party. Was dressed as a sexxy sissy. I was that skinny nerd that nobody knew. Had a a nice bubble butt. Mark the handsome popular guy had his girlfriend breakup with him. Not knowing who I was. I turned him on. We made love even after he found out I was a guy
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Crossdressing
By BillyBoy 2 Nov 2021
Envious of the girls always getting to wear those cute little bras and panties.
Becoming the Fishing Camp Princess
By Dickguy4U2 31 Oct 2021
While well over the legal age of sexual consent, my looks represented a much different picture. Broght up by a single parent overbearing mother, my being raised was far from the normal channels of a lone single male son.With mom making dresses and me the perfect slender size to model her creations, I guess you could say that the soft silk and lace never failed to stimulate me in a secret sexy way
A Halloween story
By BillyBoy 28 Oct 2021
Dressed up for Halloween and nowhere to go. Until I get invited to a last-minute party.
Macy's gay parade
By BillyBoy 23 Oct 2021
The clerk at Macy's gave me a strange look as he checked out the lingerie I was buying.
Prom night for a sissy crossdresser
By BillyBoy 19 Oct 2021
I meet a cute sissy out for prom night. But he needs a date.
The crossdresser
By BillyBoy 16 Oct 2021
Silly me gets seduced by a pretty closet crossdresser. I help her come out, so to speak. And I have a nice time as well.
working my way up to a complete sissy tramp
By BillyBoy 13 Oct 2021
A pervert friend takes me from my first hand-job, up through the progression to where I was escorting him out to bars as a woman.
Sex at a funeral home
By Alleykat 9 Oct 2021
Seduced at a funeral home by older strangers
first time caught in hers
By BillyBoy 6 Oct 2021
Wife catches me the first time. Very embarassing. But not at all as bad as when she turns me over to the kinky gay guy she works with.
An interactive fantasy game
By BillyBoy 1 Oct 2021
Going to a hotel dating game is different when all the people are matched up to their kinky fetishes and fantasies.