Page 4, Stories by BillyBoy

Be careful what you wish for

1 Mar 2022 comments

I let him dress me like a schoolgirl, tied me up and fuck me.

8.2 (27) 3289 Reads 3 Min

Needing a big cock

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!

8.2 (13) 2260 Reads 5 Min

Dad and me

24 Feb 2022 comments

dad finds me in her room wearing her panties and bra. Oh fuck!

8.7 (81) 13221 Reads 3 Min

Trying on a few new things

4 Feb 2022 comments

Another Halloween is here! Maybe this year I'll catch my first man!

9.4 (21) 2538 Reads 11 Min

Double ball gag hotel fun

28 Jan 2022 comments

A hotel get-together turns kinky with a double ball gag. Then the Master comes later.

7.8 (19) 3026 Reads 8 Min

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.

8.0 (16) 2751 Reads 9 Min

Caught in hers and compromised

21 Jan 2022 comments

Jim noticed I was wearing nylons and a bra. He used my embarrassment to his advantage.

8.9 (39) 6307 Reads 6 Min

Tell me you love me

19 Jan 2022 comments

He was great. He followed all my requests. A dream come true.

7.3 (9) 1133 Reads 2 Min

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.

8.8 (41) 12388 Reads 13 Min

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.

8.7 (36) 5409 Reads 4 Min

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.

8.8 (68) 7208 Reads 4 Min

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!

8.6 (28) 5252 Reads 5 Min

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.

8.9 (58) 11122 Reads 9 Min

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?

8.6 (23) 5106 Reads 5 Min

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.

8.4 (14) 1979 Reads 3 Min

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!

8.3 (28) 3391 Reads 3 Min

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

7.7 (10) 4294 Reads 5 Min

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!

7.9 (11) 2537 Reads 5 Min

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.

8.4 (15) 921 Reads 8 Min

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!

8.3 (9) 1611 Reads 2 Min

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.

8.0 (17) 4097 Reads 3 Min

Jock Fanatsy

1 Dec 2021 comments

Remembering sexy guys in sexy jockstraps got me thinking about having my first gay date.

8.3 (34) 2687 Reads 7 Min

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!

8.7 (11) 1660 Reads 4 Min

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.

9.2 (30) 5314 Reads 6 Min

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.

8.3 (25) 2684 Reads 6 Min

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.

8.2 (43) 7709 Reads 6 Min

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!

9.2 (37) 3052 Reads 6 Min

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.

8.5 (11) 2070 Reads 7 Min

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.

8.9 (39) 3194 Reads 6 Min

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.

8.2 (44) 4639 Reads 5 Min