Page 5, Stories by BillyBoy

Crossdressing

2 Nov 2021 comments

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

8.5 (19) 4259 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 (41) 4926 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 (47) 14117 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) 1782 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) 2153 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) 3901 Reads 6 Min

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.

9.2 (45) 5720 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.

8.2 (24) 2958 Reads 4 Min

My boss brings me into his kinky BDSM world

17 Oct 2021 comments

The title says it all

9.0 (31) 6352 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) 1834 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 (17) 1576 Reads 10 Min

scary trying to be yourself

12 Oct 2021 comments

I thought wearing my sister's underwear made me gay. I was worried about that. But it didn't. But finding someone who wasn't repulsed seeing me in her stuff was very difficult. Until now.

7.2 (6) 556 Reads 9 Min

A weird twist I'll never forget

11 Oct 2021 comments

A therapist suggests a strange clinic for me for the weekend. Somehow I get transfered into a womans body for two days. I guess you need to be carefull who you tell your fantasies to. Even your therapist!

7.9 (22) 5445 Reads 4 Min

Responding to a dominant man for the first time

10 Oct 2021 comments

Out of nowhere, I'm suddenly obeying the orders from another man. Not my usual thing. But this guy has my number.

8.9 (14) 2530 Reads 5 Min

I'm a gay sissy transgender fuck toy

9 Oct 2021 comments

When I came back from California, changed into a Caitlyn, I was surprised how many of my old schoolmates and teachers were trying to get in touch.

8.3 (23) 3605 Reads 7 Min

I married a fat girl

8 Oct 2021 comments

I only found out much later that she set me up to catch me in her undies and tricked me into becoming a sissy peg boy and later a slut for her x boyfriend who she was still fucking. I guess that is the whole story, actually!

8.3 (19) 4187 Reads 6 Min

first time caught in hers

6 Oct 2021 comments

Wife catches me the first time. Very embarassing. But not at all as bad as when she turns me over to the kinky gay guy she works with.

8.7 (25) 4645 Reads 10 Min

diapered like a helpless bitch

5 Oct 2021 comments

Joe found my personal chats and used them to blackmail and abuse me. I loved it!

7.9 (24) 11073 Reads 4 Min

An interactive fantasy game

1 Oct 2021 comments

Going to a hotel dating game is different when all the people are matched up to their kinky fetishes and fantasies.

8.1 (18) 2745 Reads 8 Min

What is a cockold? Now I think I know.

30 Sep 2021 comments

My first wife was a bitch. She put me through hell. But the second one put me through something worse. Watching her boyfriend fuck her while I was bound and gagged and tied to a chiar in the bedroom. Maybe my third wife will be nice to me.

7.5 (16) 2023 Reads 7 Min

i guess you could say she seduced me

29 Sep 2021 comments

I met her at the hotel bar. There was a crossdressing convention there that weekend. I didn't know it. But I found out soon enough.

7.9 (18) 3119 Reads 4 Min

caught crossdressing

28 Sep 2021 comments

im not very fem but i love to wear panties. A golfing partner saw my profile on a webite like this and made the most of my situation.

8.8 (26) 4509 Reads 2 Min

a secret admirrer uses me like a girl slut

15 Sep 2021 comments

Some anonymous man recognized me from my posts on this website. He orders me to meet him at a hotel but I can't see who he is. Now everyone I know is a suspect. It's really weird and scary in a kinky sort of way.

8.7 (30) 8398 Reads 3 Min

Self bondage gone right for a change

14 Sep 2021 comments

After tying myself up I invite a web chat buddy over to finish tying me, and finish me off, too.

7.1 (7) 1632 Reads 4 Min

he is a bad man

12 Sep 2021 comments

He orders me to dress in her underwear. Put on some tight restraints. I have to drive for an hour to his home. Then he treats me like his own sex toy, sex slave, and spank bitch. But I keek coming back. He is a bad man.

8.5 (17) 2267 Reads 3 Min

Caught and compromised

11 Sep 2021 comments

The guy next door was watching me dressing in my moms and x wife's old underwear for a while. He watched me playing with some self bondage for a while, too. So, this day, he bursts in and grabs me, just as I'm cumming all over. Now I'm at his mercy.

8.9 (27) 6878 Reads 12 Min

fantasy about being found out and moved up one more step

7 Sep 2021 comments

discovered by my boss and then he makes me his sissy bitch

9.1 (32) 4787 Reads 9 Min

I suppose this is how it all started for me

6 Sep 2021 comments

I remember like it was yesterday. Girls' underwear, being tied up, helpless. I guess I loved it

8.2 (12) 3114 Reads 6 Min

he noticed my panties under my jeans

5 Sep 2021 comments

caught in panties by a stranger who wanted me for sex and more sex

8.7 (30) 5218 Reads 5 Min

My brother's friend is a sissy fag

4 Sep 2021 comments

Well, I fianlly had enough and gave it to him. The little sissy fag

8.8 (30) 7404 Reads 7 Min