Below you can find the complete collection of stories by BillyBoy.
9 Mar 2022 comments
Dave and his wife are swingers of sorts. They like to bring sissy guys in for her strap-on dildo fuck while he throat fucks them. She likes to watch him suck off other guys. She likes to watch him get fucked, too. It was a crazy weekend!
7 Mar 2022 comments
A kinky way to get me really nervous and struggling.
5 Mar 2022 comments
Someone recognized me from the post in GayDemon! Maybe I was hoping that would happen?
4 Mar 2022 comments
One of several kinky bondage games the boys like to play.
3 Mar 2022 comments
Late in life I finally explored the dark side. And there is no going back.
2 Mar 2022 comments
I lived my greatest fantasy. Bound gagged and penetrated. That fucker!
1 Mar 2022 comments
I let him dress me like a schoolgirl, tied me up and fuck me.
25 Feb 2022 comments
Needing a big cock and not finding one sucks. I've always wanted one. I've always wanted a man to take me and use me like a slut. Finally, my dreams come true!
24 Feb 2022 comments
dad finds me in her room wearing her panties and bra. Oh fuck!
4 Feb 2022 comments
Another Halloween is here! Maybe this year I'll catch my first man!
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28 Jan 2022 comments
A hotel get-together turns kinky with a double ball gag. Then the Master comes later.
22 Jan 2022 comments
I played for a long time in her clothes. I even took some pictures of me dressed up pretty. Now I have men calling me all the time. What should I do? Does dressing make me gay? I do dream of sucking a big fat cock a lot. Maybe I'll answer one of the guys.
21 Jan 2022 comments
Jim noticed I was wearing nylons and a bra. He used my embarrassment to his advantage.
19 Jan 2022 comments
He was great. He followed all my requests. A dream come true.
15 Jan 2022 comments
I started wearing moms underclothes when I was younger. They were always laying around in her bedroom and in the laundry. But later I discovered he was leaving them around for me to find. He was tricking me into becoming a sissy crossdresser for him.
13 Jan 2022 comments
My gay lover left me but not before he turned me over to a gay Dom Master. I guess I should have been more careful of what I asked for.
11 Jan 2022 comments
I dressed like a girl for prom. My friend Jeff and I didn't have proper girl dates. It was sort of a joke and a few of the other boys were doing it. And Jeff's dad seemed to like me a lot.
6 Jan 2022 comments
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!
30 Dec 2021 comments
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.
28 Dec 2021 comments
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?
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22 Dec 2021 comments
'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.
17 Dec 2021 comments
She works in advertising. She is HOT! I waited for a long time to even say hello. I've never been with a trans girl. Does she still have a dick? I don't know. But I want to find out!
10 Dec 2021 comments
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
9 Dec 2021 comments
Every day I awake from a dream of being used as a girl whore. I can't stop it. I'm in trouble!
8 Dec 2021 comments
They told me the Karaoke bar it was in a gay part of the city. Now I go back frequently.
7 Dec 2021 comments
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!
2 Dec 2021 comments
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.
1 Dec 2021 comments
Remembering sexy guys in sexy jockstraps got me thinking about having my first gay date.
20 Nov 2021 comments
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!
19 Nov 2021 comments
After drinking with some seedy guys in a dive bar, I get lost and end up at their front door.