Stories by BillyBoy

Caught Crossdressing

4 Dec 2025 comments

You don't hear about these sorts of things actually happening, but they do, Caught by a pervy in my wife's panties and bra. Oh No!

8.8 (16) 3200 Reads 12 Min

Gay Golf

19 Nov 2025 comments

A golf game goes gay, and so did I

7.4 (22) 1305 Reads 5 Min

Does wearing pantyhose and a bra make me gay?

28 Oct 2025 comments

Confused as to why I feel like I should be sucking a man's cock when I'm just wearing a pair of ladies pantyhose and a cute little push up lace bra???? Am I gay?

7.2 (8) 1749 Reads 7 Min

Seduced by the 'lady' from corporate

15 Oct 2025 comments

Gail works downtown, mostly from home. But tonight, she attended the business dinner. For some reason, I was seated next to her.

9.1 (29) 2972 Reads 5 Min

Back to the gay sex toy store for more

8 Oct 2025 comments

Returning to the sex store, looking for the guy who playfully cuffed and knelt me in front of him, but I was in for a different surprise

9.4 (42) 2592 Reads 7 Min

Meeting the love of my life

11 Sep 2025 comments

a story about a girl. and me. and she isn't really a girl.

9.0 (41) 2755 Reads 10 Min

I took 'her' to the prom

11 Aug 2025 comments

A new younger friend said he always wanted to go to pram as a girl. I agreed and set it up

8.3 (20) 3103 Reads 7 Min

Halloween is a great time to experiment

9 Jul 2025 comments

My roommate suggested we try some crazy costumes and other fun stuff for this years Halloween party. I didn't know he was trying to seduce me. But it worked.

8.3 (37) 5812 Reads 3 Min

The bad man did what I wished for

13 Jun 2025 comments

i find a Dom man to meet up with. unfortunately, or maybe not, he has watched my posts for a long time and does everything I've even dreamed of. Or had nightmares of.

8.7 (36) 4031 Reads 4 Min

I'm no longer the man in charge

6 Jun 2025 comments

A normal guy gives in to his wife's requests to dress in her lingerie, giving him the best sex ever, but it's all a lie

8.0 (42) 4016 Reads 6 Min

Out for some fun turns into a rough night

28 May 2025 comments

wearing girly underwear gets me in a lot of fucking trouble

7.7 (5) 2411 Reads 2 Min

Be careful what you wish for

21 May 2025 comments

George is a real Dom. Not A PRETEND DOM!

8.2 (32) 2671 Reads 2 Min

Caught and seduced

16 May 2025 comments

The old guy working on my outdoor lighting recognized the webpage I was looking at. Later he called me to see if I might like to be his bitch. I wonder what I did?

8.4 (44) 4875 Reads 4 Min

you know what I do here, don't you?

18 Apr 2025 comments

Rumors of what my Friend's dad does to other guys in his basement got me strangely excited and curious

9.0 (55) 3565 Reads 8 Min

Caught Crossdressing

15 Apr 2025 comments

in her underwear, I'm exposed and turned into his cock slave.

5.9 (13) 4764 Reads 2 Min

Tricked into actually being his bitch

11 Mar 2025 comments

He was suppose to untie me but he had other ideas first

7.7 (45) 8952 Reads 5 Min

Car BJ turns into a long night of bondage and fucking

7 Mar 2025 comments

Daddy tricks me into his big truck and takes me for a long ride

6.5 (31) 4849 Reads 2 Min

Caught in her panties by my mean stepfather

6 Mar 2025 comments

George finds me in panties. Then the real trouble really begins

7.7 (38) 5867 Reads 4 Min

Meeting a gay sissy for the first time

5 Mar 2025 comments

My first encounter with a true gay sissy was very eye opening. She liked it kinky. And being the good friend I am, I did my best to please her.

9.0 (24) 3732 Reads 7 Min

Gay sissy hookup with daddy dom

15 Feb 2025 comments

Incest finds its way into a dark dungeon of a man

8.6 (38) 5220 Reads 4 Min

Revenge of the gay master

6 Feb 2025 comments

I forgot to watch myself when posting rude remarks online. I was found out, and the Gay Master came to visit. He did everything to me that I'd said was crude and disgusting. This a fantasy piece.

5.9 (9) 1696 Reads 2 Min

Another Gay sex encounter

5 Feb 2025 comments

My gay neighbor seduces me, then keeps me on the hook for his kinky Gay pleasures. What to do now?

7.8 (33) 3102 Reads 3 Min

Tyler said he was a top

29 Jan 2025 comments

Tyler said he was a top, but he didn't sound stern enough. I was wrong!

8.4 (27) 2084 Reads 4 Min

Too drunk to drive home

22 Jan 2025 comments

I'm drunk at his place and shouldn't drive home. He had some crazy ideas for us to try. Wife's lingerie, panties, handcuffs and a lot of cock sucking.

8.7 (41) 5572 Reads 8 Min

My Halloween crossdressing story

19 Nov 2024 comments

I knew I shouldn't, but I dressed in women's clothes again this Halloween. It turned out much different from last year, but the final results were the same. A cock in my mouth and another one in my, you know where.

7.0 (27) 5383 Reads 3 Min

Caught in hers

6 Nov 2024 comments

The gay man catches me in her panties and makes me his bondage fuck toy. I wasn't sure i was going to be ok with it, but, of course, now I love it!

7.8 (47) 3567 Reads 4 Min

Gaff panty, Cummy shorts, Deep insertion

16 Oct 2024 comments

well, the title says it all. a crazy night indeed

7.7 (13) 1955 Reads 2 Min

Cock sucking or Taking it in your ass?

11 Oct 2024 comments

what's your preference? and why? gay sex is a strange and complicated thing, isn't it?

7.4 (20) 1700 Reads 1 Min

Closet crossdressing goes very wrong, or did it?

10 Oct 2024 comments

Dressed in private but I have to answer the door for my neighbor. It turn out to be a very naughty afternoon.

8.1 (34) 7100 Reads 6 Min

Spit roasted at home

12 Sep 2024 comments

He had me cuffed, wearing a humiliating pink frilly outfit, with a huge nasty purple veined rubber cock in my mouth, and his fat cubby cock fucking my ass from behind. John was kind enough to fulfilled my fantasy for me.

8.6 (29) 4982 Reads 4 Min

BillyBoy Stories