Tell me you love me
19 Jan 2022 comments
He was great. He followed all my requests. A dream come true.
BillyBoy
Below you can find the complete collection of stories by BillyBoy.
Becoming a sissy crossdresser for him
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.
Bondage dreams come true
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.
Prom going wrong
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.
I'm his bound and gagged girlfriend
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!
After Halloween
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.
bondage blowjob
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?
Shower Power
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.
I knew she was a trans
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!
Secret Sissy
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
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Dreams and Frustration
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!
Seattle Karaoke bar experience
8 Dec 2021 comments
They told me the Karaoke bar it was in a gay part of the city. Now I go back frequently.
My secret dreams
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!
Halloween party
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.
Jock Fanatsy
1 Dec 2021 comments
Remembering sexy guys in sexy jockstraps got me thinking about having my first gay date.
Now I'm a crossdressing Domme?
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!
wrong place, wrong time
19 Nov 2021 comments
After drinking with some seedy guys in a dive bar, I get lost and end up at their front door.
I found him out. But then he found me out!
12 Nov 2021 comments
My cousin has been single forever. I always wondered how he manages it. I've been with girls. I even got a little gay for a while. But that is me. Mike is a whole different story.
Doctors are human too
11 Nov 2021 comments
I forgot and wore some panties to my check-up. The doc was surprised. But he responded differently than I expected.
blow and go buddy gets kinky
10 Nov 2021 comments
Joe was always pretty much a Dom. But he seemed to figure out I'd do pretty much anything to suck him off. So he just keeps pushing. Now I have to go out and buy some items he requested. And that is a whole other story!
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Nanny cam gone bad
5 Nov 2021 comments
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.
My first time being dom'ed
4 Nov 2021 comments
The rumors that I'd sucked off a guy from work got around. I guess I seemed like an easy mark. A boss from work took me to lunch. He had the Grilled roast beef. I got my lunch directly from him.
My first real gay encounter
3 Nov 2021 comments
I reluctantly go to a party with my girlfriend. She gets drunk and I get gay.
Crossdressing
2 Nov 2021 comments
Envious of the girls always getting to wear those cute little bras and panties.
Seduced by the 'girl next door'
29 Oct 2021 comments
I know she is a trans or whatever. But she is so nice. I finally agree to stop over for a drink and some pie. Later she had me sucking her straw and eating her ass like a pie.
A Halloween story
28 Oct 2021 comments
Dressed up for Halloween and nowhere to go. Until I get invited to a last-minute party.
Married Couple looking for Submissive playmate
27 Oct 2021 comments
A Married couple posting a search for a sub-male playmate. Bob is looking for a playmate. He has no intention of sharing me with his wife.
Macy's gay parade
23 Oct 2021 comments
The clerk at Macy's gave me a strange look as he checked out the lingerie I was buying.
Cockold. What is that?
22 Oct 2021 comments
Cockold? I guess I shouldn't have asked. But she was already into it big time. It was too late for me. And it still is.
bound to please
20 Oct 2021 comments
I made a mistake and posted a photo of a guy bound and gagged on my Facebook page. Clearly a gay BDSM reference. No one knows I'm secretly submissive and dream of being topped. Well, I sent that message, and boy did it come back to me.