Gay Crossdressing Stories

GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.

Got my wish (ch. 2)

By Luvonstkylip 18 Dec 2023

This is the other part of " Got my wish".. My crossdressing encounter that I had one night when I was spun!!!

8.1 (17) 2883 2 Min Comments

Weekend with a Dom Master fuck buddy

By BillyBoy 12 Dec 2023

i finally joined Grinder and a guy liked my fetish and kinky desires. He fucked me like a whore.

8.5 (14) 3613 6 Min Comments

Femboy chronicles (ch. 9)

By Johndoe 15 Nov 2023

Caly is in for a rough session after giving Chris a tough time, hope you like it!

8.8 (13) 3695 9 Min Comments

My neighbor

By Eric 14 Oct 2023

My neighbor, didn't see this happening

7.9 (48) 8950 4 Min Comments

Going to my prom

By BillyBoy 12 Oct 2023

Yeah, I'm too old, but I wanted to go to a real prom dressed like a girl anyway.

7.6 (14) 3078 8 Min Comments

Crossing the line (ch. 3)

By lickme 25 Sep 2023

Ruby starts to live out her fantasy of pleasing a man

8.6 (23) 2866 4 Min Comments

House help is my Master now (ch. 5)

By Slutty Whore 15 Sep 2023

The slave is now married and loses his virginity to his mastee. But there is more to it....

8.2 (14) 2895 7 Min Comments

Crossdressing Freak

By Getoutofmymind 13 Sep 2023

I have a huge cigarette fetish. I have had it since I was seven or eight. I’d sneak into my mom’s cigarettes and pretend to smoke them. I would also sneak into my mom’s things, her bras, panties, and most of all her tall boots. So now, being grown I’ve become a crossdresser, passable too, and when I dress, I smoke. These two fetishes have made me a complete freak and an exhibitionist.

8.4 (13) 2367 4 Min Comments

Mistress of Cindy submitted male slut

By Italian sub Cindy 8 Sep 2023

how my wife from submitted become Mistress and me amale sissy, submitted and slut

8.2 (17) 3448 19 Min Comments

Daddy and Candy

By Maikol 29 Aug 2023

An admirer who was very excited after reading some of my stories here sent me this story where I play the the role of Candy and told me to publish it, he wrote most of it and I added a few more details. I think he is Daddy!

8.3 (16) 4546 4 Min Comments

Trailer trash cumdump

By Alleykat 19 Aug 2023

How I became white trash for rednecks at the trailer park

8.4 (112) 20776 3 Min Comments

Falling for an older married man

By Maikol 13 Aug 2023

Falling for an older married man

8.6 (40) 8229 4 Min Comments

Tie me up and fuck me like that

By BillyBoy 11 Aug 2023

The first time with a dom alpha guy and I ask to be tied up. But why?

8.9 (29) 5855 8 Min Comments

Frat Initiation

By Victor 2 Aug 2023

The president of the frat is slowly manipulating his freshman pledge, a masculine, cocky, gorgeous muscleboy to his will during hell week when all the pledges have to dress up like French maids and serve their future frat brothers at a party. The new pledge realizes he liked it a little too much.

9.3 (156) 16302 28 Min Comments

First or was panties

By Alleykat 24 Jul 2023

I kept staring at those sexy panties in the adult bookstore

9.3 (82) 8617 5 Min Comments

Mentor

By BillyBoy 14 Jul 2023

I'm not a young buck anymore, but another old man showed this dog some new tricks.

6.7 (16) 2360 3 Min Comments

Bobby's Pink Panties

By luvaslip 6 Jul 2023

Bobby has been hiding a big secret and he meets a stranger who helps him fulfill that secret and more.

8.8 (66) 6730 5 Min Comments

Playdate with Daddy

By BillyBoy 26 Jun 2023

call me daddy. yes Sir. oh, sorry, yes daddy

8.6 (28) 6928 8 Min Comments

A visit to Canada changes my life

By Maikol 11 Jun 2023

I was cleaned up inside and out. He liked that my body was hairless and commented about not having to shave. Dressing me up in stockings, garter belt, panties, bra and a very girly dress all in pink we went to the living room where he sat on one end of the couch and I kneeled in the middle being instructed on how to suck cock.

8.5 (42) 4672 4 Min Comments

Secret Kisses (ch. 2)

By luvaslip 7 Jun 2023

Contuing story of young and old beginners as they grow in their relationship. Joni wants all the cock she can give as Kyle tries to make her happy

8.7 (13) 1383 4 Min Comments

Caught by Aunt's Boyfriend

By Katie Femboy 5 Jun 2023

Stayed at my Aunts house most weekends, thought the house was empty and got caught in her lingerie by her boyfriend. He ran out quite fast but ended up sending me a drunken text message

8.5 (58) 9969 3 Min Comments

Bar Bathroom fuck

By Viki 14 May 2023

A story of how I finally got to courage to dress up and search for a cock to fill me up.

8.9 (47) 6871 8 Min Comments

Wife discovers husbands sissy secret

By SecretsissyJ 10 May 2023

Wife forces husband to embrace his sissy side after she discovered his secret stash

8.8 (70) 13189 6 Min Comments

Child hood bestfriend helping me open my eyes

By Famsammie 8 May 2023

When I first got started in general with crossdressing my childhood bestfriend help my development all the way around

8.9 (29) 6070 6 Min Comments

Seduced and on my knees

By BillyBoy 5 May 2023

Visiting a hotel bar during a gay drag queen weekend, I become involved with some dominant crossdressing ladies

8.3 (16) 2600 3 Min Comments

My Vegas trip

By Jester4fun 24 Apr 2023

My real Vegas trip:)

9.4 (191) 4020 10 Min Comments

He showed me I have a girl inside (ch. 8)

By Jerryisjulie 24 Apr 2023

Daddy’s hold on me gets stronger - my lessons continue

9.2 (37) 5191 4 Min Comments

Prom Dress Contest for The Boys

By BillyBoy 22 Apr 2023

Having all the sissy's in town show up wasn't as hard as I thought

5.8 (10) 2507 8 Min Comments

Bras, Bros and Blowjobs

By BillyBoy 21 Apr 2023

my study buddy caught me playing in my sisters underwear

7.5 (25) 6711 5 Min Comments

First time sex as a CD

By Jester4fun 21 Apr 2023

My dream come true

9.3 (188) 7262 5 Min Comments