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!
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.
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?
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.
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
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.
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
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!
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!
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.
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By Alleykat 30 Nov 2021
Turned into the park cocksucker by a fat old man
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.
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!
By Somewhat Straight 17 Nov 2021
It took while, but my transformation is complete
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.
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.
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.
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.
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
By BillyBoy 2 Nov 2021
Envious of the girls always getting to wear those cute little bras and panties.
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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
By BillyBoy 28 Oct 2021
Dressed up for Halloween and nowhere to go. Until I get invited to a last-minute party.
By BillyBoy 23 Oct 2021
The clerk at Macy's gave me a strange look as he checked out the lingerie I was buying.
By BillyBoy 19 Oct 2021
I meet a cute sissy out for prom night. But he needs a date.
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.
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.
By Alleykat 9 Oct 2021
Seduced at a funeral home by older strangers
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.
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.
By BillyBoy 30 Sep 2021
My first wife was a bitch. She put me through hell. But the second one put me through something worse. Watching her boyfriend fuck her while I was bound and gagged and tied to a chiar in the bedroom. Maybe my third wife will be nice to me.