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.

holidays with grandad (ch. 2)

By Sisyboy 21 Sep 2019

Part 2 of getting caught

7.3 (45) 9614 2 Min Comments

holidays with grandad

By Sisyboy 20 Sep 2019

unexpected encounter with 18 year old boy and his grandad.

7.4 (32) 11728 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) 4656 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) 3714 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 (63) 6770 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

7.4 (31) 4396 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) 4127 4 Min Comments

Roommate surprise

By Steve Webb 24 Jun 2019

A horrific moment turns into a dream night

8.4 (89) 12307 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) 17119 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 !!!

8.2 (64) 8388 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.

8.7 (53) 34759 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) 8803 5 Min Comments

Daddy's Sissyboy (ch. 3)

By Rainsky 25 Mar 2019

A plan has been formed for seduction.

8.8 (51) 8635 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 (87) 15443 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) 6844 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) 10827 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.

8.9 (55) 14001 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.

8.2 (65) 14323 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) 18455 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) 21385 4 Min Comments

Boy to College Girl

By Sissy Scarlet 29 Nov 2018

Charles has battled against his feminine features all his life. It takes a single experience with a dominant, alpha high school jock in the locker room to make him know his place in the world. ! ARCS Needed !

8.6 (88) 30186 23 Min Comments

I'm a Slutty Cheerleader

By Brett 7 Nov 2018

Daddy wanted to fuck a teen cheerleader and I wanted him to fuck me, so he bought the outfit and I got more than I could have hoped for.

8.5 (80) 16004 8 Min Comments

The making of a sissy

By Jamie Villa 13 Sep 2018

How my fascination with all things femme began

7.0 (70) 9372 3 Min Comments

First me then my wife become a black guys bitch

By Shy Stuart 21 Jul 2018

A newly married young man is lured into becoming a black guys bitch but does he have the nerve to go through with it?

7.7 (124) 23401 6 Min Comments

My Love of Lingerie, carried me away.

By fetishlover 28 Jun 2018

I love wearing lingerie, and my best pal found out and gave me some help

8.2 (42) 10687 8 Min Comments

Sleazy Landlord

By Sissy Scarlet 12 Jun 2018

Jesse has been spending too much of his money on his... hobby. Now rent is due, what ever will he do? :)

7.7 (65) 12182 3 Min Comments

Singapore to Dubai unexpected journey (ch. 3)

By zeenatcd 12 Jun 2018

Razak showed me the heaven during sex and i became his slave.

9.2 (17) 4042 6 Min Comments

Boy to Bride (Feminization Novella)

By Sissy Scarlet 8 Jun 2018

Adam MacDonald secret life of crossdressing has always been both the escape and high of his life. A mysterious package with no sender address arrives one day, and inside it contains: a dress and more!

6.2 (82) 28714 7 Min Comments

A little body modification can be SO beneficial.

By Lingerielover 30 May 2018

I get my balls changed and my cock replaced with a..

7.5 (107) 44576 6 Min Comments

The Days when Girls still had Dicks

By Georgie d'Hainaut 29 May 2018

Sorry for being away for a while. I was forced by very sad circumstances. But I'm back again with what you might call a discovery trip from childhood to adult life

7.8 (13) 975 9 Min Comments

Good Lumberjack, Bad Lumberjack

By Sissy Scarlet 26 May 2018

A foreign loser in his hometown, a boy works at a carnival where he is embarrassed by dehumanizing customers. A charming Alpha finds the boy in tears, comforts him, and the two end up starting a secret relation

7.3 (30) 3707 5 Min Comments

Singapore to Dubai unexpected journey (ch. 2)

By zeenatcd 21 May 2018

This is the story how I reached to Dubai and how I was used during the journey.

8.8 (22) 3161 5 Min Comments

Chrissy's New Life

By sluttybttm4u 17 May 2018

Phillip/Chrissy has been seeking a loving life in the hands of a very loving man

5.2 (24) 6017 2 Min Comments

Homophobe gets feminized (ch. 2)

By Ben Drake 12 May 2018

Richard is given his first lesson and he had better pass.

6.4 (50) 8483 2 Min Comments

Buying tights and panties started a new life......

By fetishlover 11 May 2018

I went to buy new tights and panties, met a guy buying similar and our lives changed for ever!!

7.8 (37) 14927 13 Min Comments