Gay Crossdressing Stories, Page 3

Becoming Joni Kayse

By luvaslip 13 Jun 2024

Joni and her Uncle are on their way to colorado, on a graduation trip., there is some naughtiness on the way.

8.5 (29) 3022 5 Min Comments

Crossdressing Boot Bitch

By Prettyboy 13 Jun 2024

Jackie is a crossdresser and has new pair of women's knee high white patent leather laced boots and is looking for a top. Jackie hooks up with a leather boy, Jeff.

8.5 (13) 869 3 Min Comments

Uncle's Magic Hands

By luvaslip 11 Jun 2024

Uncle Owen has future plans for his pretty nephew. But patience is the big key.

8.8 (19) 4493 7 Min Comments

Dave

By LostSoul 31 May 2024

An amazing holiday hookup.

7.8 (16) 2786 7 Min Comments

First time at a gloryhole

By Jester4fun 26 May 2024

True story of my first time visiting a gloryhole

9.3 (124) 8067 6 Min Comments

My wishing star (ch. 6)

By Kaysa 24 May 2024

Kevin and Clark get to work. It's not easy for Kev with all his body changes, but it becomes harder when he forgets something very important...

8.7 (12) 1651 10 Min Comments

Uncle's Hand

By luvaslip 20 May 2024

Young Johnny becomes his uncle's sex toy and ultimately his wife.

7.5 (25) 5850 8 Min Comments

Only One Draw (ch. 6)

By Habu 10 May 2024

The Pitches

9.6 (6) 656 20 Min Comments

Walking in the Mall

By luvaslip 5 May 2024

Jerry meets a charming new friend while out for an early walk in the local Mall.

8.1 (8) 2514 6 Min Comments

Auntie and Uncle

By David Tossell 4 May 2024

A boy living with Aunt and Uncle for a holiday

6.8 (29) 5082 3 Min Comments

Chrisy - The Sissy Slave

By Slutty Whore 4 May 2024

See how two horny ass adults convert a straight boy into a submissive sissy slave that becomes a horniest slut

8.4 (51) 8551 6 Min Comments

Married Man love being a woman

By Joey 2 May 2024

Married Man prefers to be a woman

8.2 (22) 4109 2 Min Comments

Stacey's First Love (ch. 2)

By luvaslip 15 Apr 2024

Stacey goes into the Army where he meets Dexter and they have a love filled weekend.

9.6 (9) 890 4 Min Comments

Wearing my wife's thongs

By Viki 15 Apr 2024

Just a short story - I sent him pictures of me in my wife's thong. He liked them, especially how my ass looked in them.

8.0 (10) 3011 4 Min Comments

The pond

By luvaslip 8 Apr 2024

Stacey is at her friend and lover's funeral as she reflects on the past.

8.8 (3) 507 23 Min Comments

A crazy idea comes true

By BillyBoy 29 Mar 2024

A drag queen makes me her boy toy

9.4 (27) 3026 8 Min Comments

Gay or Not Gay?

By BillyBoy 27 Mar 2024

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!

7.7 (18) 2899 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) 2366 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) 6240 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) 2866 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 (58) 8088 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) 1625 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) 1500 4 Min Comments

Crossdressers first BBC

By Jester4fun 26 Feb 2024

My first BBC

9.2 (207) 15594 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.

9.8 (19) 3230 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) 1101 7 Min Comments

My time in the Brothel

By Joey 24 Feb 2024

My time working in the Wild West in a Brothel

7.9 (33) 3326 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.

8.8 (47) 9977 26 Min Comments

Spring Break (ch. 3)

By 243907 8 Feb 2024

fucking, group sex, cross-, dressing, domination

8.4 (11) 2154 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) 755 5 Min Comments

Gay Crossdressing Stories

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