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.

I Would Never Kiss a Guy (ch. 2)

By GabbyGurl 11 Nov 2020

Gabby is falling for Nate!

9.4 (34) 2541 7 Min Comments

The Librarian (ch. 3)

By cut 10 Nov 2020

first gay bar

8.7 (20) 1705 3 Min Comments

1st BBC

By Danielle 30 Oct 2020

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

7.1 (57) 33084 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…

9.3 (140) 6048 17 Min Comments

Hungry for more

By Karl 5 Oct 2020

On the prowl after getting a taste for gay sex

8.3 (24) 3056 4 Min Comments

Scrambled Eggs

By Nils Huim 29 Sep 2020

A young college student helps his wealthy, much older roommate entertain a group of potential investors.

7.1 (18) 1466 7 Min Comments

Earning Power

By Petr-Johan 25 Sep 2020

Two factory workers find that their boyfriends, bored at home, have taken a fancy to ladies lingerie. Their money is stolen which forces all four of them into a line of work that none of them had ever done before but desperation for funds is very motivating.

8.8 (36) 2250 26 Min Comments

My teacher abuses me

By Darkdesires 16 Sep 2020

Guske wiped his dick with a tissue while giving my a disgusted look as I cried with the cum running down my face and soaking my shirt. His gaze changed. I think my broken state turned him on. I must have reminded him of those girls you see in porn who look destroyed by the time the video is over.

8.7 (107) 31182 20 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) 1123 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) 1404 5 Min Comments

I Would Never Kiss a Guy

By GabbyGurl 8 Sep 2020

Crossdresser finds love at the gym

9.1 (48) 4676 7 Min Comments

101

By Nils Huim 27 Aug 2020

A gay bottom has a sexual adventure with a stranger

7.5 (43) 13144 6 Min Comments

The Ways and Wanderings of a boy (ch. 3)

By Georgie d'Hainaut 21 Aug 2020

But after holidays the new life goes on. However: it takes an unexpected turn

9.4 (9) 552 24 Min Comments

I love My Dirty Daddy (ch. 4)

By Mikal 17 Aug 2020

This is my 4th installment in I Love My Dirty Daddy. While I am sure you may all enjoy Lolas Daddy dominating her and having her fuck other guys to get his this is a story about Lola who like her Daddy is polyamorous and enjoys having her own adventures. I love the input of other readers.

8.8 (8) 4957 7 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 (57) 22681 4 Min Comments

Ghost Hunk (ch. 4)

By Oddballs 1 Aug 2020

This body is really proving to be a challenge for the horny and raunchy ghost to control. This time around, Polter decides to give Blake a more... Simpler perspective on the night. Such includes making Blake thinks his ass has to have cock in it, getting on his knees and sucking MASSIVE meat, and then putting himself into a small orgy to really cement to the jock that the ghost is in control.

9.2 (8) 3635 34 Min Comments

I love My Dirty Daddy (ch. 3)

By Mikal 29 Jul 2020

Well it's been a while since I have had a chance to write but I'm back to it. Lola and her Daddy decide to go out for their 3rd anniversary and have a bit of fun with their friend which end with Lola getting a tramp stamp and an ass fucking from a guy with a titanic cock.

8.8 (14) 3348 7 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.

9.1 (121) 27229 14 Min Comments

Gary's Choice (ch. 14)

By Major Tom 24 Jun 2020

That Timothy was the first of my three children to get married was a big surprise. Then again, our lives had been so surprising.

9.3 (20) 2139 5 Min Comments

my life (ch. 18)

By bijim 19 Jun 2020

the end of my training being turned loose in the world as a transsexual submissive slut

8.8 (22) 2866 9 Min Comments

Gary's Choice (ch. 13)

By Major Tom 17 Jun 2020

"Now that I feel that mouth on my dick, I'm sure! This is the pro my firm used to hire to relieve us during late nights. Oh yeah! I know this tight ass so well." A family gathering went off in other directions.

9.3 (17) 1639 4 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

7.9 (23) 6416 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.

9.2 (23) 2945 43 Min Comments

Gary's Choice (ch. 12)

By Major Tom 12 Jun 2020

"I did what needed to be done..." There was a new business venture.

9.2 (15) 1812 3 Min Comments

my life (ch. 17)

By bijim 10 Jun 2020

a club dancing and developing a crush on a guy

9.7 (16) 2791 9 Min Comments

I love My Dirty Daddy (ch. 2)

By Mikal 9 Jun 2020

Lola's Dirty Daddy Eric decides to give a lecture about sissy's to novice doms and share his little sissy with them.

9.0 (19) 4975 7 Min Comments

my life (ch. 16)

By bijim 5 Jun 2020

going to the doctors and taken out in public for the first time,

9.2 (19) 2515 5 Min Comments

Gary's Choice (ch. 10)

By Major Tom 3 Jun 2020

"None of us has shame. We can't afford shame, Anyway, all that's over. Tim's settled in at that factory and it's all's good." "I had tried to block that out. It was the most horrible thing I was responsible for."

9.0 (22) 1968 5 Min Comments

Gay sex change?

By Rubbertransformation 31 May 2020

I love taking cock but often wonder what it would be like to have a pussy instead!

9.0 (41) 9346 6 Min Comments

my life (ch. 15)

By bijim 31 May 2020

more abuse from bill a double penetration surprise and falling for a milking machine

9.4 (18) 1947 7 Min Comments

Turn About is Fair Play

By Mikal 30 May 2020

Turn About is Fair Play is a Caesars Bitch Sweet Chrissi cross over both are Detroiters and Jay Jay is mentioned in my 1st Sweet Chrissi as JJ. Anyway Caesar takes his cross dressing sissy boyfriend Jay Jay out they meet Chrissi and things get real naughty.

8.0 (5) 577 6 Min Comments

Sweet Chrissi (ch. 5)

By Mikal 29 May 2020

Dear Rears I really struggled with the decision to allow the Pandemic to be an element in my story. But I am writing a story about a cute sissy that lives in Detroit which has been impacted heavily and so I included it.

9.2 (11) 2507 3 Min Comments

Gary's Choice (ch. 9)

By Major Tom 29 May 2020

"'Good boy!' He did some blow. 'Want some?' 'Yes sir, please.' He spread two lines on his fat dick that I had just been sucking on. I put my face down and snorted it off him. "Thank you, sir." I was buzzed and horned to take his prize tool up my ass."

9.1 (20) 2441 6 Min Comments

Those tough Marines are just as queer as the rest of us! (ch. 5)

By jon martin 27 May 2020

Stan has some downers and uppers.

9.1 (27) 1636 3 Min Comments

Gary's Choice (ch. 8)

By Major Tom 25 May 2020

"I sat at the kitchen table not believing what my shaking father was trying to explain to me. The only way out was for one of us kids to become a sex worker and work the debt off. I did what I was supposed to do and said yes." More from Timothy.

9.4 (19) 2295 6 Min Comments