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.

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) 1061 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) 1056 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) 7779 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) 399 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) 947 9 Min Comments

Changes (ch. 3)

By bud C 21 Jul 2016

Learning the cross dresser life

8.7 (42) 4984 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) 39026 12 Min Comments

Changes (ch. 2)

By bud C 15 Jul 2016

A cross dresses journey

8.4 (28) 3644 13 Min Comments

Changes

By bud C 14 Jul 2016

A cross dressers Journey

8.6 (51) 9705 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) 518 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) 4079 42 Min Comments

Director's Choice

By Habu 30 May 2016

Hired to Play Romeo to cross-dressed Juliet

8.3 (50) 6700 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 (254) 73039 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.

8.3 (155) 16474 6 Min Comments

Halfway

By Habu 2 May 2016

Stuck in GM land between nowhere and nowhere else

8.3 (32) 2988 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) 2877 30 Min Comments

After Poker

By Habu 21 Mar 2016

Everyone gains and loses from a poker party.

8.4 (60) 13105 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) 7670 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) 3015 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) 19574 4 Min Comments

Ana Le Babe - Becoming A Cross Dresser

By Ana Le Babe 21 Nov 2015

This story is how my alter ego, Ana Le Babe, came into being. This and following stories relate the encounters she has had (both sexual and general), and are all true. In writing this, I hope to help others in a similar situation deal with their feelings and stimulate those that are interested in our way of life.

7.5 (62) 10744 9 Min Comments

The clients

By Angie K 16 Oct 2015

Fun with a wife and her cross-dressing husband

8.2 (36) 4859 4 Min Comments

Truck Stop Encounter (ch. 2)

By bud C 12 Oct 2015

fun at the truck stop

9.0 (79) 6078 21 Min Comments

Truck Stop Encounter

By bud C 9 Oct 2015

Fun at the truckstop

8.9 (78) 11277 28 Min Comments

Painting Donovan (ch. 4)

By DSDS 18 Sep 2015

Alright, so I decided it was unfair to end this series on a cliffhanger. If you read this and want more, say something.

9.0 (69) 1753 16 Min Comments

My first BBC

By mwmalone 31 Aug 2015

A true story of my first BBC and being his crossdressing slut

8.1 (102) 28265 9 Min Comments

MY First Cross-dress experience: Simply Awesome

By sunny 21 Jul 2015

My first crossdressing story

7.2 (33) 10324 7 Min Comments

Noah Flip Flop

By Habu 20 Jul 2015

American college student traveling South Seas on winter holiday hooks up with Australian street musician in Sydney

9.1 (47) 2315 17 Min Comments

Blue Dragon

By Habu 13 Jul 2015

Small town Ohio café waiter Casey dreams of escaping and finding sexual adventure.

8.0 (50) 2825 9 Min Comments

Tennis Interview

By Habu 25 May 2015

Why would a tennis pro base in Bangkok?

8.9 (37) 1611 17 Min Comments

The sissy within me The Transformation from boy to Daddies sissy

By Ed 27 Apr 2015

Justin is slowly transformed into a sissy by his new daddy

7.2 (126) 38561 6 Min Comments

While the cats away, I get to play

By mwmalone 4 Apr 2015

A fantasy of becoming a black mans sissy slut but hope it cums true someday

7.9 (46) 8726 14 Min Comments

The sissy within me

By Ed 23 Mar 2015

This straight acting boy/guy has a sissy hidden inside him and is found out about by a friend who transforms him into the true sissy he wants to be.

7.4 (146) 50791 6 Min Comments

wow

By charles-smythe 23 Mar 2015

glory hole suck

8.7 (57) 4070 9 Min Comments

Decoy

By Habu 17 Mar 2015

Arab subterfuge played out a Washington, D.C., pro men's tennis tournament.

8.7 (42) 2085 16 Min Comments