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.

The Skin of Things (ch. 16)

By Chris Lewis Gibson 4 Feb 2020

He could still feel Ezekiel's mouth on his, and on his neck. He could still feel Ezekiel's chest and stomach against his back, Ezekiel in him, and through him, his penis, swelling and pumping in his mouth, the warm touch of the palm of his hand.

9.6 (9) 241 11 Min Comments

Condo for Sale

By Habu 3 Feb 2020

Sex helps sell expensive San Francisco condos.

8.8 (42) 2473 18 Min Comments

My First time with a man

By Bob Long 2 Feb 2020

An encounter that just happened after years of repression

8.4 (83) 6910 14 Min Comments

Parking lot blowjob

By Bob Long 1 Feb 2020

This is the story of how my ex girlfriend, made it her mission to get me to suck a guys cock

7.3 (40) 9816 25 Min Comments

How I got started

By Bob Long 30 Jan 2020

This is how I began my life as a crossdresser, encouraged by my mother who lovingly guided me and embraced my desires to dress as a women

8.0 (131) 10727 12 Min Comments

The Art of the Sissygasm

By cock whore kimmy 26 Jan 2020

Little CD fuckdoll has his first sissygasm and his life changed forever!

8.5 (49) 10665 3 Min Comments

Sweet Chrissi (ch. 2)

By Mikal 22 Jan 2020

A new tale about the continuing adventures of Chrissi.

8.2 (20) 1596 5 Min Comments

Caught crossdressing

By SandyCD 6 Jan 2020

Caught by daughter with me dressed as woman

8.7 (85) 15211 12 Min Comments

Big Sissy

By Nils Huim 28 Dec 2019

A gay sissy bottom receives a surprise birthday gift

7.8 (16) 10828 10 Min Comments

Amateur Crossdressing Prostitute

By Kristen Kross 23 Dec 2019

crossdresser's first time prostituting first timer

8.8 (92) 21114 10 Min Comments

A Sissy’s Dream Comes True! Again and again!!

By FishnetSissy 21 Dec 2019

2 blonde bimbos help a little sissy faggot become the girl he always wanted to be and Introduce him to a man who knows just what to do with a special girl like this!

7.8 (72) 34562 29 Min Comments

My New Apartment Manager

By Kristen Kross 21 Dec 2019

cd sissy meets her apartment manager

8.7 (67) 6330 9 Min Comments

Starbucks

By Nils Huim 16 Dec 2019

Two ex-cons have anal & oral sex and then plot (?) a robbery

7.7 (21) 1765 10 Min Comments

Living my dream

By SissyBoi 9 Dec 2019

A true story about me finally giving in to my deepest desire to become a cum addicted slut that loves being fucked and used as a toy, worships huge cocks and eats cum for breakfast.

7.4 (30) 8219 6 Min Comments

Un-Expected Threesome

By Kristen Kross 7 Dec 2019

CD, girl, and a stranger meet in a motel room

8.7 (16) 2914 25 Min Comments

holidays with grandad (ch. 2)

By Sisyboy 21 Sep 2019

Part 2 of getting caught

7.3 (44) 9459 2 Min Comments

holidays with grandad

By Sisyboy 20 Sep 2019

unexpected encounter with 18 year old boy and his grandad.

7.5 (31) 11551 1 Min Comments

Met Mistress on grindr (ch. 2)

By zeenatcd 14 Sep 2019

My mistress made me her slave and gang banged me with her friend Domino,Alisa and Mariana.

7.8 (11) 4521 6 Min Comments

When and How did I start (ch. 2)

By Crossy Arora 26 Jul 2019

How my life changed from imagination to reality

8.3 (22) 3694 2 Min Comments

Dressed for success

By Steve Webb 23 Jul 2019

A friendly tourist gets the surprise of his life. A fantasy

8.2 (62) 6723 6 Min Comments

When and How did I start

By Crossy Arora 13 Jul 2019

First of all, it's my real story, which I am going share with you guys. I was born as a boy named Rahul

7.6 (30) 4377 2 Min Comments

The birth of Slutty Tanya

By Slutty Tanya 9 Jul 2019

A chance encounter leads an occasional cross-dresser down the path of becoming a full time slut.

7.2 (34) 4080 4 Min Comments

Roommate surprise

By Steve Webb 24 Jun 2019

A horrific moment turns into a dream night

8.4 (86) 12026 5 Min Comments

Cross dressing went too far

By fetishlover 20 May 2019

My love of wearing panties, stockings and tights went too far nad got me into serious trouble...

7.4 (56) 16922 6 Min Comments

My new body modification

By Lingerielover 25 Apr 2019

My mini cock and balls are driving me mad, so I did something about it !!!

8.3 (63) 8212 6 Min Comments

Girly

By bootlicker 22 Apr 2019

A small, weak, submissive man is feminized and abused by a trio of dominant perverts intent on transforming him into their sissy slave gurl.

8.6 (52) 32907 66 Min Comments

Dressed as an Easter Bunny, Fucked like a Rabbit

By Shy Stuart 19 Apr 2019

Me and my gurlie friends go to the local tranny club dressed like Easter Bunnies and get fucked like rabbits

8.4 (37) 8758 5 Min Comments

Daddy's Sissyboy (ch. 3)

By Rainsky 25 Mar 2019

A plan has been formed for seduction.

8.8 (48) 8331 11 Min Comments

First me then my wife become a black guys bitch (ch. 2)

By Shy Stuart 10 Feb 2019

I bottle out of going into Carlton house and he's not happy. However, a week or so later while in a drunken stupor I give Carlton my address and invite him around to fuck me.

7.7 (86) 15162 4 Min Comments

Met Mistress on grindr

By zeenatcd 21 Jan 2019

This story about how I met mistress who enjoyed me and did BDSM on me.

7.9 (29) 6591 6 Min Comments

I was a man this morning, but now?

By fetishlover 20 Jan 2019

Girfriend gets revenge on her man after finding him with a gay guy

7.4 (55) 10708 8 Min Comments

Daddy's Sissyboy (ch. 2)

By Rainsky 7 Jan 2019

fathers lust might be more than just lust. A son longing for his fathers cock. A strange box arriving with the postman and lots of thoughts.

8.8 (54) 13387 7 Min Comments

Daddy's Sissyboy

By Rainsky 27 Dec 2018

As things are revealed, things get hot between a father and his son. This is a requeast from one of my readers, enjoy xoxo rainsky.

8.1 (63) 13716 7 Min Comments

Getting dominated by an 9 inch cock

By Sissy Bitch 27 Dec 2018

Got dominated by a 9 inch cock while i was traveling

6.4 (81) 18108 2 Min Comments

How i became a bitch addicted for cock

By Sissy Bitch 23 Dec 2018

My history on how i became a little bitch that can not live without cock.

7.3 (97) 21052 4 Min Comments