Gay Crossdressing Stories, Page 4

How did I know? I wasn't just walking into a gay porn club and waving a rainbow flag. I needed to be persuaded, seduced or pushed a little bit, so I could say, I'm not gay, they made me gay!

7.5 (21) 3013 6 Min Comments

MY CD Chronicles

By NealPhat 24 Mar 2024

When it started and the rush and fun from it all

8.2 (17) 2457 3 Min Comments

How to become a gay sissy crossdressing slut

By BillyBoy 23 Mar 2024

from a young age I took one step after another to end up here

6.0 (13) 6656 2 Min Comments

We met for a beer

By BillyBoy 22 Mar 2024

I wore lingerie under my slack and polo. He liked that a lot

8.1 (14) 3101 5 Min Comments

Straight acting Chris lost a bet and his punishment was to be a cage dancer for 1 hour at a gay club, but he had to do it dressed like a slut. Colin and Kevin are straight, best friends, and roommates. They venture to the same club that night for a celebration. When Colin sees Chris dancing in a cage, something stirs inside of him and all he wants now is Chris.

9.7 (65) 8838 51 Min Comments

Becoming a Top (ch. 2)

By Prettyboy 2 Mar 2024

Ricky is Carl's bitch boy. Ricky is wearing a pink bra, skirt, and high top pink Chucks waiting for Carl to come home and fuck him. Carl enjoys topping Ricky wearing knee high black laced boots.

9.4 (6) 1674 4 Min Comments

Is that a boy or a gurl (ch. 2)

By Luvonstkylip 28 Feb 2024

This other side of me, she's is me , in fact I'm on her other side?.. wtf, that means!!!

6.5 (4) 1584 4 Min Comments

Crossdressers first BBC

By Jester4fun 26 Feb 2024

My first BBC

9.2 (222) 17041 8 Min Comments

The beauty of lingerie (ch. 2)

By Thatslife 25 Feb 2024

Following on from my first introduction to lace, in particular panties by my mother. I was now very interesting in exploring what other types of lingerie effected my cock and level of horniness. My search took me to the contents of my mother's underwear drawers.

9.6 (25) 3596 8 Min Comments

Coercion (ch. 16)

By Tommy 24 Feb 2024

I felt I was being watched, but wasn’t sure by whom and went about continuing with my plans wherever they took me and anticipated a big surprise soon, just not sure what.

9.7 (4) 1176 7 Min Comments

My time in the Brothel

By Joey 24 Feb 2024

My time working in the Wild West in a Brothel

7.8 (34) 3519 3 Min Comments

The Walk Of Shame

By NeedyScorpio 22 Feb 2024

I was used by two older men after working hard on their property.

8.9 (51) 10574 26 Min Comments

Spring Break (ch. 3)

By 243907 8 Feb 2024

fucking, group sex, cross-, dressing, domination

8.4 (11) 2253 6 Min Comments

Is it just me? (ch. 3)

By Luvonstkylip 5 Feb 2024

My journey continues as I begin to realize how much I don't understand about myself and where my heart is.

8.5 (2) 786 5 Min Comments

His wife missed out this time, or did she?

By deansaz 14 Jan 2024

He and I had sexually shared his wife for a long night, but this time....she didn't show and he had some kinky needs......

8.8 (24) 2926 3 Min Comments

Laundry will never be the same

By Ky 3 Jan 2024

Growing up laundry was one of our chores my brother and I had to rotate weekly between our sisters. We jokingly dared each other to try on our sisters clothes but had no idea what start between us

7.0 (15) 3722 3 Min Comments

Long trips aren't always bad

By Luvonstkylip 3 Jan 2024

A short fantasy of something I've imagined while lying in bed.

8.5 (6) 1870 4 Min Comments

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) 2979 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.

8.6 (15) 3763 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) 3895 9 Min Comments

My neighbor

By Eric 14 Oct 2023

My neighbor, didn't see this happening

8.0 (52) 9480 4 Min Comments

Gay Crossdressing Stories

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

Only One Draw (ch. 6)

Walking in the Mall

Auntie and Uncle

Chrisy - The Sissy Slave

Married Man love being a woman

Stacey's First Love (ch. 2)

Wearing my wife's thongs

The pond

A crazy idea comes true

Gay or Not Gay?