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 zeenatcd 18 Oct 2021
I met one mature men on grindr and and then we enjoyed a lot in hotel room. He fucked my 2 times in row continuously. Then he became my fantasy partner.
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 BillyBoy 12 Oct 2021
I thought wearing my sister's underwear made me gay. I was worried about that. But it didn't. But finding someone who wasn't repulsed seeing me in her stuff was very difficult. Until now.
By BillyBoy 9 Oct 2021
When I came back from California, changed into a Caitlyn, I was surprised how many of my old schoolmates and teachers were trying to get in touch.
By BillyBoy 8 Oct 2021
I only found out much later that she set me up to catch me in her undies and tricked me into becoming a sissy peg boy and later a slut for her x boyfriend who she was still fucking. I guess that is the whole story, actually!
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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 5 Oct 2021
Joe found my personal chats and used them to blackmail and abuse me. I loved it!
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.
By BillyBoy 29 Sep 2021
I met her at the hotel bar. There was a crossdressing convention there that weekend. I didn't know it. But I found out soon enough.
By BillyBoy 28 Sep 2021
im not very fem but i love to wear panties. A golfing partner saw my profile on a webite like this and made the most of my situation.
By popperboi 25 Sep 2021
A young virgin continues his first bathhouse experience. Fortunately a Masterful Black Daddy takes him under his wing
By Don 18 Sep 2021
How my life change forever
By Don 17 Sep 2021
How a trip to grocery store changed my life.
By MontanaBiGuy 17 Sep 2021
Alone in a bookstore and got surprised with my cock in my hand
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By BillyBoy 15 Sep 2021
Some anonymous man recognized me from my posts on this website. He orders me to meet him at a hotel but I can't see who he is. Now everyone I know is a suspect. It's really weird and scary in a kinky sort of way.
By Badman 15 Sep 2021
Interracial story. A sissy boy meets a cruel mature black man and dresses as a pigtailed girl for him. The cruel man treats the little sissy rough, tearing off his clothes and ripping apart his favourite little white cotton school panties before spanking and raping him. The theme and story line runs parallel to "Sissy Boy Loses Panties To Perverts"
By BillyBoy 14 Sep 2021
After tying myself up I invite a web chat buddy over to finish tying me, and finish me off, too.
By Heather_xd 13 Sep 2021
This is a short story of what has just happened early on a Sunday and left me wanting more
By BillyBoy 12 Sep 2021
He orders me to dress in her underwear. Put on some tight restraints. I have to drive for an hour to his home. Then he treats me like his own sex toy, sex slave, and spank bitch. But I keek coming back. He is a bad man.
By BillyBoy 11 Sep 2021
The guy next door was watching me dressing in my moms and x wife's old underwear for a while. He watched me playing with some self bondage for a while, too. So, this day, he bursts in and grabs me, just as I'm cumming all over. Now I'm at his mercy.
By BillyBoy 6 Sep 2021
I remember like it was yesterday. Girls' underwear, being tied up, helpless. I guess I loved it
By BillyBoy 5 Sep 2021
caught in panties by a stranger who wanted me for sex and more sex
By Heather_xd 4 Sep 2021
What Heather became after finishing with her first Master.. This is all pre the Internet.
By BillyBoy 4 Sep 2021
Well, I fianlly had enough and gave it to him. The little sissy fag
By Daves 4 Sep 2021
Prefer top or versatile crossdressers like smooth. I enjoy getting buttfucked. Love sucking dick. Prefer smooth, not hairy. Mutual sucking. Like taking turns fucking each other. Was always attracted to fem boys just turned me on.
By BillyBoy 3 Sep 2021
Tricked into crossdressing for Halloween
By Lacee00lessa 3 Sep 2021
Some of my friends took me to a rap concert I got backstage and three thugs invited me to a backstage party.....
By BillyBoy 2 Sep 2021
I posted some pics of me in my sister's panties and bra. I guess I should have expected to be used like a girl slut
By satyrDaddy 2 Sep 2021
Michael comes to see his online Daddy