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.

Mr. Phillips's Loves My Body

By Browncherrygurl 21 Dec 2017

A trusted neighbor finally gets the opportunity to take advantage if a young crossdresser he has be watching through his window

8.7 (95) 11071 8 Min Comments

Gurl Story

By Browncherrygurl 19 Dec 2017

Crossdresser meets craigslist date at isolated dive bar and has a rough unexpected time

8.4 (39) 7161 16 Min Comments

My Cross dressing Story with Friend And His Father

By zeenatcd 16 Dec 2017

A guy gets banged by a father and son due. Read hot crossdressing story of threesome sex when he was made to dress as a woman.

7.7 (41) 16306 6 Min Comments

Invisible seams CAN sometimes be exactly that

By fetishlover 12 Dec 2017

two cross dressing guys get more than they bargained for asking for seamless underwear!!!!

7.5 (20) 4671 7 Min Comments

Think Before You Speak

By fetishlover 10 Dec 2017

Love doing a little cross dressing and its a shame that I have a cut cock which show through all my pantyhose and panties etc.....

7.4 (19) 3198 6 Min Comments

Quick Enslavement (ch. 3)

By Anon 27 Jul 2017

This is the first two chapters of quick enslavement which have been corrected and the final third part of a very sudden enslavement of an old sub/slave. He is quickly taken over and made to service his Master in many ways some of them extremely unpleasant.

8.7 (18) 2627 39 Min Comments

Big Mistake

By bud C 22 Jul 2017

Getting drunk isn't a good idea

7.8 (60) 13328 16 Min Comments

Craigslist Quickie

By bud C 21 Jul 2017

Meeting a guy

9.1 (84) 16036 22 Min Comments

Quick Enslavement (ch. 2)

By Anon 9 Jul 2017

An old slave goes to his Master's home to be trained for the weekend and the first night proves very demanding and challanging for the old slave

8.7 (24) 2658 14 Min Comments

Learning to be a Girl

By Cari C 6 May 2017

Becoming a pretty, sexy girl in public eventually leads to some very unexpected results!

9.0 (114) 15471 21 Min Comments

Fem Black Uber driver stranded with Japanese tourists

By Mr.GoodBooty 30 Apr 2017

Mixed hertiage Uber driver Javier is stranded with two Japanese tourist in the heart of a major winter storm.

7.9 (27) 3932 15 Min Comments

My Second BBC

By mwmalone 30 Apr 2017

Posting Craigslist ads and I found a man who would finally use me like a whore...

8.7 (77) 14648 10 Min Comments

White Cable Man, Latin Weed Dealer & young Black CrossDresser

By Mr.GoodBooty 25 Apr 2017

A big booty fem black male crosses two fantasies off his bucket list when the white Cable Man and Latin weed dealer met at his apartment one early Saturday morning in Tampa Florida

8.9 (35) 4293 12 Min Comments

Meeting 'Katie'

By acessez 3 Apr 2017

the fictional account of my first encounter with 'Katie' in amsterdam

7.7 (24) 2766 10 Min Comments

Locker Room Romp

By Gauged 4 Feb 2017

Heating up in a locker room

8.4 (59) 9572 6 Min Comments

Escape to Constantinople (ch. 7)

By Habu 30 Jan 2017

Back in Constantinople, Pyotr returns to the bed of the American diplomat Kenneth O'Dell and, while mooning for Katya, finds a reason to accept O'Dell's offer to take him to the States.

9.0 (34) 1049 20 Min Comments

Escape to Constantinople (ch. 6)

By Habu 28 Jan 2017

Pyotr's last protector in Constantinople, a Greek, takes him to Smyrna, where a pogrom against Greeks has Pyotr on the dock not knowing if death will come before evacuation. Once more Katya turns up and saves him when the Turks start killing the men on the docks. Pyotr finds protection in the bed of a Turkish officer; Katya turns out not to be who/what Pyotr thought Katya is, which clears up some confusion he's had of his sexual preferences.

9.1 (27) 1044 35 Min Comments

Rescued from pantyhose peril by officer Ron

By Zman350 29 Dec 2016

A straight married cop comes to the rescue of a cross dresser, and discovers a hidden desire

8.7 (77) 7615 9 Min Comments

Syndrome (ch. 9)

By Shyann Lee 29 Dec 2016

"No, you can still call me that." Rex said, letting out a deep exhale, "Look, I'm here, which means I still love you very much. I don't think I could ever stop loving you. You've been my brother for what, 11-12 years?! How can I just turn those feelings for you off? It's impossible. So, yeah, I'm still your brother....

7.8 (5) 391 34 Min Comments

Opposites Attract (ch. 4)

By wabuck 12 Aug 2016

Joe discovers that Craig has another man in his life.

8.3 (20) 924 9 Min Comments

Changes (ch. 3)

By bud C 21 Jul 2016

Learning the cross dresser life

8.6 (41) 4944 40 Min Comments

A Very Naughty Night

By Cari C 20 Jul 2016

Cari goes out dressed as a sexy woman to a night club and becomes a woman in the arms of a very masculine man!

8.6 (263) 38932 12 Min Comments

Changes (ch. 2)

By bud C 15 Jul 2016

A cross dresses journey

8.4 (28) 3623 13 Min Comments

Changes

By bud C 14 Jul 2016

A cross dressers Journey

8.6 (50) 9646 38 Min Comments

True Confessions (ch. 23)

By Mighty Mouth 30 Jun 2016

My association with the most fantastic guy I've ever met, who is now my employee. Also I see my first live sex show in a theater.

7.4 (10) 515 7 Min Comments

The Affair

By Angie K 13 Jun 2016

"YOU BITCH!!!!" she screamed. "YOU DAMNED, FILTHY BITCH!!!' Tears were streaming down her face as she softly cried, "I trusted you! How could you?"

8.5 (10) 4018 42 Min Comments

Director's Choice

By Habu 30 May 2016

Hired to Play Romeo to cross-dressed Juliet

8.3 (50) 6667 13 Min Comments

Becoming Daddy's Girl

By Cari C 17 May 2016

A cute young cross dresser submits to the wants of a "Daddy".

8.9 (251) 72176 41 Min Comments

A new Bookstore

By charles-smythe 11 May 2016

For years I'd frequented adult bookstores. I would look around the shop a little pretending to be interested in buying something from the store. After what I felt was a sufficient amount of time browsing I would get tokens from the clerk, always hesitating to look directly at him so as not acknowledge what I was about to do.

8.2 (154) 16422 6 Min Comments

Halfway

By Habu 2 May 2016

Stuck in GM land between nowhere and nowhere else

8.3 (32) 2968 39 Min Comments

All Fools' Day Foolery

By Habu 30 Mar 2016

Power top NYPD vice cop Mike Kavanagh hunts blonds and a serial killer of blonds in New Orleans

8.8 (42) 2855 30 Min Comments

After Poker

By Habu 21 Mar 2016

Everyone gains and loses from a poker party.

8.4 (60) 13045 37 Min Comments

The Adult Bookstore

By Angie K 21 Mar 2016

"You know.....there's a lots of men here who'd probably love to have you suck them. And, maybe, they'd like to fuck your pretty bottom."

6.2 (29) 7522 6 Min Comments

Trapped

By charles-smythe 13 Mar 2016

Besides discovering the joys of sucking dicks I've reconnected with Linda and old girlfriend and briefly moved in with her in her mobile home in Kennedale. This had a double pay off. Besides living with Linda, it put me less than fifteen minutes from the adult bookstores with the viewing booths.

8.8 (23) 2911 21 Min Comments

Bathouse Fun

By iamcontent 8 Jan 2016

I pay my admission get my locker put my clothes in it, shower dry off and lube my ass up just in case, but also love having a finger stuck in me.

7.7 (92) 19491 4 Min Comments