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.

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) 29778 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 (79) 15877 8 Min Comments

The making of a sissy

By Jamie Villa 13 Sep 2018

How my fascination with all things femme began

7.1 (69) 9206 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 (123) 22777 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 (41) 10413 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) 11957 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) 3963 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) 28005 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 (104) 44279 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) 958 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) 3661 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) 3118 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

5.5 (22) 5965 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) 8423 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!!

7.9 (35) 14746 13 Min Comments

Homophobe gets feminized

By Ben Drake 11 May 2018

Max kidnaps Richard and teaches him how to be a good slave girl.

5.6 (41) 10080 1 Min Comments

Abandoned Parking Lot (ch. 2)

By Sissy Scarlet 9 May 2018

After fighting with a drunk girlfriend, a boy is fed up with women. He decides to finally live out a fantasy he's had for years.

8.0 (94) 20946 2 Min Comments

Abandoned Parking Lot

By Sissy Scarlet 7 May 2018

After fighting with a drunk girlfriend, a boy is fed up with women. He decides to finally live out a fantasy he's had for years.

6.6 (68) 26794 3 Min Comments

Singapore to Dubai unexpected journey

By zeenatcd 1 May 2018

This is story how we caught by one Arab guy in bathroom and he also enjoyed sex with me and he offered me to come Dubai.

8.2 (20) 5656 6 Min Comments

Wish I had not worn those lace panties

By Lingerielover 16 Apr 2018

Gay cross dresser wore new lace panties and things suddenly got out of hand!!!

7.8 (40) 14722 12 Min Comments

Sex with my boss honeymoon in Singapore

By zeenatcd 2 Apr 2018

This is a third part of my Singapore honeymoon trip. We enjoyed our best honeymoon night in hotel room.

8.0 (19) 6887 6 Min Comments

strapped in Houston

By knickerlesstina 16 Mar 2018

it was hot in Houston but I was determined to go out on the town that night. I had a red mini dress on with red strappy sandals. Pink Victoria's Secret panties and bra. Long reddish hair and well made up ...

6.8 (29) 3551 5 Min Comments

hit on in my London hotel...

By knickerlesstina 14 Mar 2018

meeting the man of my dreams in the bar of my London hotel and having a wonderful time after initial hesitation...

7.4 (30) 5827 4 Min Comments

the Silver Swan...

By knickerlesstina 13 Mar 2018

night out at the Silver Swan leads to sex in a 4x4...

7.6 (22) 1951 3 Min Comments

Singapore trip with arjun Boss (ch. 2)

By zeenatcd 5 Mar 2018

We had dinner in hotel sex in bathroom and then we had sexiest night at the hotel. Hotel arranged honeymoon for us.

8.1 (18) 4575 4 Min Comments

Porn star debut

By DevilBrew69 5 Feb 2018

Travis takes the first step to his porn star career.

8.0 (30) 2822 4 Min Comments

Revenge is sweet !!!!

By fetishlover 23 Jan 2018

Gay guy loves wearing leotards, pantyhose, panties and swimsuits.

7.5 (22) 4921 6 Min Comments

Became My Friend's Mom (ch. 2)

By zeenatcd 16 Jan 2018

Even after banging my ass for the whole night, the horny family was not satisfied. They gave me a beautiful dress and banged my ass once again.

7.7 (39) 20375 5 Min Comments

Became My Friend's Mom

By zeenatcd 5 Jan 2018

This is a gay incest sex story of a guy with his friend and his dad. After my friend's mom left the town, father and son made me their bitch for two days.

7.2 (74) 35898 4 Min Comments

Lap Dance For Rent Money

By Browncherrygurl 24 Dec 2017

Short for this month's rent money must perform for a disgusting old geezer.

7.5 (33) 8819 5 Min Comments

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) 21106 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.

8.0 (36) 9969 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 (34) 5854 16 Min Comments

Sugar-Coated Hot Pepper

By Habu 22 Dec 2017

Banished CIA agent mixes it up in Key West.

9.4 (63) 3992 40 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.

8.2 (25) 3708 4 Min Comments