Gay Crossdressing Stories

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

An Ex-Boyfriend's Revenge

By Browncherrygurl 23 Dec 2017

An angry ex-boyfriend gets his last surprising act of humiliation against his gurl

7.8 (59) 20750 5 Min Comments

Trying panties and stockings for the first time.

By fetishlover 23 Dec 2017

Never thought that just wearing two ideas of womens underwear could get such fantastic results.

8.3 (33) 8686 4 Min Comments

Gurl Story (ch. 2)

By Browncherrygurl 22 Dec 2017

During blackout in a small town motel, a sissy learns never to tease the wrong man

8.2 (33) 5562 16 Min Comments

What I wear UNDER my suits.!!! first CD experiment

By fetishlover 22 Dec 2017

bored gay guy, thought I would experiment with some cd bits and pieces with my pal.

8.1 (24) 3392 4 Min Comments

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 (91) 10593 8 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.

7.8 (39) 14969 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!!!!

7.4 (19) 4456 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) 2931 6 Min Comments

Craigslist Quickie

By bud C 21 Jul 2017

Meeting a guy

9.0 (82) 15716 22 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 (113) 14680 21 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) 4065 12 Min Comments

Meeting 'Katie'

By acessez 3 Apr 2017

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

7.7 (24) 2599 10 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 (76) 7071 9 Min Comments

Anal Punishment

By BubbleButt Slayer 25 Jul 2016

Sissy boy loses the game, now he's going to lose his anal virginity.

8.0 (165) 54218 16 Min Comments

Changes (ch. 3)

By bud C 21 Jul 2016

Learning the cross dresser life

8.6 (41) 4816 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 (262) 38652 12 Min Comments

Director's Choice

By Habu 30 May 2016

Hired to Play Romeo to cross-dressed Juliet

8.2 (49) 6563 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 (246) 69934 41 Min Comments

Dave and Janet

By Angie K 18 Mar 2016

"I wonder what your parents would think? I wonder if they know their little boy was a cross-dressing, cock sucking slut?"

6.3 (96) 16624 4 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 (89) 19172 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) 10634 9 Min Comments

The clients

By Angie K 16 Oct 2015

Fun with a wife and her cross-dressing husband

8.2 (36) 4659 4 Min Comments

Truck Stop Encounter (ch. 2)

By bud C 12 Oct 2015

fun at the truck stop

9.0 (77) 5664 21 Min Comments

My first BBC

By mwmalone 31 Aug 2015

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

8.1 (96) 26355 9 Min Comments

MY First Cross-dress experience: Simply Awesome

By sunny 21 Jul 2015

My first crossdressing story

7.2 (33) 9820 7 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

7.3 (122) 35617 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

7.7 (43) 8047 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.

7.5 (144) 48701 6 Min Comments

The neighbor made me his bitch

By mwmalone 25 Jan 2015

Older neighbor borrows some tools but ends up making me his bitch.

7.4 (467) 128790 10 Min Comments

Sissy slut Gangbanged hard and put up wet

By mwmalone 22 Dec 2014

Total fantasy of mine to be used by several men, even though this has not cum true I hope it will one day.

8.7 (205) 64501 13 Min Comments