Gay Crossdresser Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressing up as women and gay sex with transvestites and crossdressers.

Bang, Bang

By JemOfAGirl 7 Aug 2021

This story was written from the prompt "Sexy Cops and Robbers". That is all I had to write this story, so that is all you get before reading to see what I came up with.

7.5 (19) 4147 16 Min Comments

Friday Night at the Neighbors

By satyrDaddy 5 Aug 2021

Kenny gets outed and used by neighbor couple

8.2 (26) 4560 7 Min Comments

Young Sugar

By satyrDaddy 28 Jul 2021

A curious couple, reverses the sugar Daddy idea

7.3 (17) 1451 2 Min Comments

Made Over

By Victor 27 Jul 2021

College football star meets a man who shows him he can be a stud with a feminine side.

9.3 (161) 16059 55 Min Comments

Jizelle

By satyrDaddy 23 Jul 2021

Jizelle becomes obsessed with Daddy watching her cum for him

8.3 (7) 1404 1 Min Comments

The first time i got caught crossdressing

By A Anal Addicted Slut 3 Jul 2021

Caught crossdressing & what i had to do to have my secret kept.

8.6 (124) 48353 11 Min Comments

My first & earliest sexual experiences with a man

By A Anal Addicted Slut 2 Jul 2021

This story is based on my actual experience. My first earliest sexual experiences with a man. Including the first time i was fucked & a few times after.

8.2 (57) 14128 13 Min Comments

Horny Asian Boi and The Black (ch. 2)

By Lonely Planet Boy 19 Jun 2021

" Be a good neighbor", so my boyfriend sent me to make a good relationship with a lonely straight American , ex Navy.

6.0 (9) 2581 9 Min Comments

I love My Dirty Daddy (ch. 5)

By Mikal 16 Jun 2021

So I have been a bit busy with work lately but I still wanted to add to the I Love my Dirty Daddy stories but how I mean it would get boring if every story is about Daddy handing Lola over. So I thought perhaps a prequel on how they actually got together in the first place.

8.8 (7) 2294 5 Min Comments

From student to sissywhore

By bootlicker 14 Jun 2021

A university student is drugged, blackmailed, and forced to become a submissive sissygurl slave for a perverted retired teacher and his friends as they transform her into a feminized thoroughly abused sex toy.

8.6 (64) 32154 44 Min Comments

Public sex

By Alleykat 14 Jun 2021

I’m a cocksucking faggot

8.6 (30) 4241 2 Min Comments

Lingerie Disaster

By Frank Chainges 31 May 2021

I have always a little lingerie under my suits for work, has my luck finally run out???

7.8 (18) 3773 4 Min Comments

Mail Order Slut (ch. 3)

By bootlicker 25 May 2021

The captive sissy is prepared and opened for her owner, and taken repeatedly in a night filled with oral and anal fucking by the African Chief.

8.4 (54) 7556 14 Min Comments

Mail Order Slut (ch. 2)

By bootlicker 23 May 2021

The captive sissy is transported to meet her new owner and the start of her transformation into a feminized slave is begun. She is trained to provide him with pleasure and taken upon delivery...given her first thorough fucking and used as his slut.

9.0 (40) 8017 23 Min Comments

Turned into a sissy

By Alleykat 16 May 2021

Forced by a stranger photographed blackmailed used by strangers at the park dressed like a little girl. This is the 3rd part of my adventure into becoming the sissy boy/girl I want to be.

8.9 (57) 15216 3 Min Comments

Sissy's Need Dick

By Mikal 9 May 2021

A lonely Crossdressing Femboi Isolated by the Covid restriction takes charge and gets the dick she so desperately needs

8.5 (28) 5136 8 Min Comments

Cherry (ch. 2)

By Cirkle7 2 May 2021

More from Turner’s basement.

9.1 (27) 6936 16 Min Comments

Meating Samantha

By JoeSoapNamibia 28 Apr 2021

My one and only meeting with a very hot cd

8.1 (10) 1277 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 (73) 7787 5 Min Comments

My Sophomore Sweetheart (ch. 2)

By silkybottom 17 Apr 2021

Pt. 2 of "The Gym Teacher". I finally find my man and embark on the quest of seducing him. It's a difficult start, but I'm unwilling to falter.

8.3 (10) 1487 7 Min Comments

My Sophomore Sweetheart

By silkybottom 16 Apr 2021

High school is the time when I really let my naughty and wild side come out. Hormones and lust got the better of my docile and innocent little mind and introduced me to a whole new world of sexuality. It was a time to remember, for both me, and my first real man crush

6.5 (11) 2551 7 Min Comments

One wild night in a posh hotel

By MontanaBiGuy 9 Apr 2021

This is several fantasies of mine rolled into one. Hope you enjoy reading as much as I enjoyed writing it.

8.9 (19) 2499 29 Min Comments

Plumbered

By Habu 5 Apr 2021

A guy renovating his house finds just the right plumber.

9.4 (98) 9816 37 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 (62) 11685 3 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 (57) 6186 5 Min Comments

The Wall

By Caliban 20 Feb 2021

A bricklayer teaches a feisty queen a lesson...

9.0 (359) 6652 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

8.7 (22) 8823 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 (80) 19764 11 Min Comments

Gay Pride

By Habu 25 Jan 2021

Alumni jock on frat gangbang trip falls for gay stripper.

9.4 (86) 6851 27 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 (65) 13207 12 Min Comments

Daddy's Surprise

By Thormand1963 19 Jan 2021

Bisexual man gives his meet-up Daddy a crossdressing surprise

8.7 (41) 5385 8 Min Comments

The Blond Foreigner

By Habu 16 Jan 2021

Stranger mixes up love relationships at Spanish café.

9.6 (15) 1671 35 Min Comments

Muscle Daddy Wears Lingerie

By ManScent 31 Dec 2020

A muscle stud wears lingerie and gets fucked like a housewife in his penthouse.

9.3 (57) 10548 10 Min Comments

I Would Never Kiss a Guy (ch. 5)

By GabbyGurl 24 Dec 2020

Gabby makes a commitment to Nate.

9.6 (34) 2679 4 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,

9.3 (48) 7200 21 Min Comments