Gay Crossdressing Stories

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

Meating Samantha

By JoeSoapNamibia 28 Apr 2021

My one and only meeting with a very hot cd

8.1 (10) 1194 10 Min Comments

Taken

By Alleykat 26 Apr 2021

Six years ago I was just a innocent boy, I took a shortcut home at the park late at night.

9.1 (69) 6832 5 Min Comments

Becoming a sissy wife (ch. 2)

By Punkboi18 3 Apr 2021

After I moved in with Rick I quickly became his submissive slave. I learned I loved my daily punishment and enjoyed the pleasure that comes with pain.

8.8 (60) 10462 3 Min Comments

Femboi Freddie at the Truck Stop

By Nathan James 27 Mar 2021

Freddie was a very femanine gay boy who them big old burly truckers loved.

6.4 (39) 10257 2 Min Comments

The cruising park

By Punkboi18 19 Mar 2021

My first night in my towns notorious cruising spot and my first time having anonymous sex with strange men.

9.0 (48) 5167 5 Min Comments

Girl friend sets me up to get turned into a sissy

By Wannabesissy 11 Mar 2021

So I'm 35 masculine male with beard and tattoos, I also have a girl friend. But I have a secret, when u get high on crystal all I can think about is big hard cock. So much so that I just run off on my gf and get caught.

7.7 (36) 9303 5 Min Comments

Just another night whoring

By desire_e4bbc 3 Mar 2021

Another beautiful night fulfilling my desires

8.7 (17) 3289 3 Min Comments

The Wall

By Caliban 20 Feb 2021

A bricklayer teaches a feisty queen a lesson...

9.0 (358) 6463 7 Min Comments

My wife watched as I got fucked by a big cock (ch. 2)

By Bob Long 16 Feb 2021

Sorry this took so long to post but with everything thats been going on in the world I hadn't had time. This is the follow up to on my encounter with Dave my wife's friend who helped her get revenge on my for having some rough sex. As always this is 100% true and factual with the exceptions of the names of the parties involved

8.6 (18) 6706 24 Min Comments

Becoming a Slut The First Time Out

By Tye Dye Sissy 11 Feb 2021

I go to an adult bookstore for my first time while dressed as a Gurl and get my first sex with men, lots of men. sissy, first time, spanked, DP.d, oral, anal, domination, sexy, slut

9.2 (74) 17440 11 Min Comments

Forced Sissy

By Dave H. 10 Feb 2021

A trip to P-town transformed me.

8.0 (54) 13176 3 Min Comments

Lost Bet Leads to Humiliating Sissification

By Sissy Stacy 6 Feb 2021

How a lost bet lead me to becoming the sissy slave of my neighbor

8.9 (85) 20281 14 Min Comments

Gone fishing

By Gpasboi 21 Jan 2021

He told me that he had put some clothes on my bed that I could wear for the night until my stuff had a chance to air out. When I walked in my room there on the bed was a white tshirt and a pair white silk panties with lace trim and I yell to Jim what the hell is this ?

8.4 (64) 12220 12 Min Comments

Daddy's Surprise

By Thormand1963 19 Jan 2021

Bisexual man gives his meet-up Daddy a crossdressing surprise

8.7 (38) 5031 8 Min Comments

The truck driver (ch. 3)

By bijim 23 Dec 2020

the final of my story being taken by two truck drivers and turned into a sissy bitch,

9.4 (41) 6289 21 Min Comments

When I found out I was really a whore

By desire_e4bbc 22 Dec 2020

How I truly became a crossdressing whore and loved it

8.7 (23) 4505 4 Min Comments

Daniel Effeminate College Student (ch. 14)

By Colourfast 14 Dec 2020

A series of stories about effeminate college twinks and their encounters with mature gentlemen

8.9 (6) 1127 22 Min Comments

Tell Tales Of A Jock

By Labeautifull 13 Dec 2020

A college Quaterback is caught all dolled up in Ladies Langerie by his Roommate who happenes to be the Wide reciever of their Team.

8.9 (39) 3949 29 Min Comments

I Would Never Kiss a Guy (ch. 4)

By GabbyGurl 26 Nov 2020

Gabby makes a major lifestyle decision and visits Nate.

9.4 (30) 3821 9 Min Comments

I become Amanda in Prison

By Amanda 12 Nov 2020

A fantasy tale of a spell of incarceration

8.4 (28) 12177 5 Min Comments

1st BBC

By Danielle 30 Oct 2020

When I realized rge saying "once you go black you never go back is true"

7.2 (46) 30871 5 Min Comments

The Girl Within Me

By Caliban 7 Oct 2020

Ninh’s first feminine adventure has an unusual consequence, after ‘she’ meets Allister…

9.4 (134) 5288 17 Min Comments

Hungry for more

By Karl 5 Oct 2020

On the prowl after getting a taste for gay sex

8.4 (22) 2924 4 Min Comments

The Kiss

By Nils Huim 11 Sep 2020

A pair of sex partners, one of them a CD, invite a third man over

7.7 (6) 1041 9 Min Comments

My second encounter with a guy whom I met in metro

By Hema CD 9 Sep 2020

My second encounter in gay sex with a guy whom I met in metro. Read how we connected met and read the story in detail to know more about the encounter

7.1 (8) 1302 5 Min Comments

101

By Nils Huim 27 Aug 2020

A gay bottom has a sexual adventure with a stranger

7.6 (42) 12946 6 Min Comments

A Harmless White Nylon Thong

By nylonlingerie 3 Aug 2020

I received a small parcel through the post, not ordered anything from any mail order, so I carefully opened it..

7.0 (56) 21975 4 Min Comments

A Sissy Life

By Faedirk 7 Jul 2020

Cat-sitting for your neighbors becomes alot more exciting when you stumble upon their wardrobe collection.

9.2 (117) 26288 14 Min Comments

Meetup Gone Crazy

By Luke Holton 16 Jun 2020

After I met a guy at his hotel, him and his team tie me to a bed and chloroform me. Read to find out what happens next

8.2 (20) 5350 11 Min Comments

Failed Connections

By Habu 12 Jun 2020

It's all about the pro soccer player's need in fetish play in Denver and Chicago.

9.4 (21) 2745 43 Min Comments