Page 4, Stories by BillyBoy

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 (40) 6593 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) 1230 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 (43) 14617 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.

8.6 (40) 5705 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.

8.9 (70) 7638 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 (29) 6262 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) 11626 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) 5630 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) 2176 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!

8.4 (31) 3643 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

7.2 (11) 4681 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 (12) 2669 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) 964 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) 1717 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) 4373 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) 2799 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) 1745 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) 5730 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) 2782 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.

8.3 (45) 8239 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) 3187 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.

8.4 (13) 2227 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 (40) 3351 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) 4767 Reads 5 Min

Crossdressing

2 Nov 2021 comments

Envious of the girls always getting to wear those cute little bras and panties.

8.5 (19) 4635 Reads 10 Min

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.

8.9 (45) 5857 Reads 6 Min

A Halloween story

28 Oct 2021 comments

Dressed up for Halloween and nowhere to go. Until I get invited to a last-minute party.

8.8 (48) 14877 Reads 7 Min

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.

8.2 (13) 2160 Reads 8 Min

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.

9.2 (18) 2262 Reads 5 Min

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.

7.6 (23) 4071 Reads 6 Min

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.

9.3 (47) 5996 Reads 6 Min

Prom night for a sissy crossdresser

19 Oct 2021 comments

I meet a cute sissy out for prom night. But he needs a date.

8.1 (27) 3246 Reads 4 Min

My boss brings me into his kinky BDSM world

17 Oct 2021 comments

The title says it all

9.1 (33) 7322 Reads 9 Min

The crossdresser

16 Oct 2021 comments

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.

9.0 (14) 2065 Reads 5 Min

working my way up to a complete sissy tramp

13 Oct 2021 comments

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.

8.6 (18) 1739 Reads 10 Min