Gay Crossdressing Stories

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

7.8
11 Votes

Met Mistress on grindr (ch. 2)

Story by zeenatcd

14 Sep 2019 3808 Readers comments 6 Min Read

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

Topics: Anal Sex, Crossdressing, DP, Dildo, Rimming, Big Dick, Group Sex, Friends, Sissy, Oral & Blowjobs, Master & Slave, Gangbang

8.1
58 Votes

Dressed for success

Story by Steve Webb

23 Jul 2019 6494 Readers comments 6 Min Read

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

Topics: Anal Sex, Crossdressing

7.2
34 Votes

The birth of Slutty Tanya

Story by Slutty Tanya

9 Jul 2019 3813 Readers comments 4 Min Read

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

Topics: Crossdressing, Slut, Gloryhole, Oral & Blowjobs

8.4
83 Votes

Roommate surprise

Story by Steve Webb

24 Jun 2019 11110 Readers comments 5 Min Read

A horrific moment turns into a dream night

Topics: Anal Sex, Crossdressing, Bisexual, Roommate, Oral & Blowjobs

7.3
51 Votes

Cross dressing went too far

Story by fetishlover

20 May 2019 15880 Readers comments 6 Min Read

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

Topics: Anal Sex, Crossdressing, Dildo, Big Dick, Boypussy

8.3
59 Votes

My new body modification

Story by Lingerielover

25 Apr 2019 7510 Readers comments 6 Min Read

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

Topics: Anal Sex, Crossdressing, Transformation

8.3
43 Votes

Girly

Story by bootlicker

22 Apr 2019 23653 Readers comments 63 Min Read

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

Topics: Piss, Crossdressing, Chastity, Dildo, Big Dick, Hairy men, Sloppy Hole, Enema, Slut, Sissy, Oral & Blowjobs, Master & Slave

8.2
49 Votes

She turned me out

Story by Bob Long

13 Mar 2019 8972 Readers comments 26 Min Read

My girlfriend not only encouraged my crossdressing but how she turned me into the cock sucking whore I am

Topics: Black Men, Anal Sex, Crossdressing, Handjob, Rimming, Spanking, Role Play, Oral & Blowjobs, Cuckold

7.6
68 Votes

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

Story by Shy Stuart

10 Feb 2019 13775 Readers comments 4 Min Read

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.

Topics: Black Men, Anal Sex, Crossdressing, Sissy, Boypussy, Drunk

7.3
54 Votes

I was a man this morning, but now?

Story by fetishlover

20 Jan 2019 10071 Readers comments 8 Min Read

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

Topics: Anal Sex, Crossdressing, Transgender, Cum, Face Fuck, Revenge, Transformation

8.2
63 Votes

Sissy Hypno Vids ... how I've changed

Story by need2btakenow

29 Dec 2018 13538 Readers comments 7 Min Read

I started watching sissy hypno about 3 years ago. Played with the idea of dressing up as a CD many times growing up and occasionally as an adult. But the fad would pass and go away for years. Not anymore...

Topics: Dildo, Hypnotized, Butt Plug

8.5
82 Votes

Boy to College Girl

Story by Sissy Scarlet

29 Nov 2018 27334 Readers comments 22 Min Read

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 !

Topics: Anal Sex, Crossdressing, Public Sex, Locker Room, Transgender, Sissy, High School, Twink, Oral & Blowjobs

8.5
78 Votes

I'm a Slutty Cheerleader

Story by Brett

7 Nov 2018 15000 Readers comments 7 Min Read

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.

Topics: Anal Sex, Crossdressing, Daddy, Slut, Oral & Blowjobs

7.1
65 Votes

The making of a sissy

Story by Jamie Villa

13 Sep 2018 8282 Readers comments 3 Min Read

How my fascination with all things femme began

Topics: Crossdressing, Cum, Pantyhose, Oral & Blowjobs

7.6
59 Votes

Sleazy Landlord

Story by Sissy Scarlet

12 Jun 2018 10928 Readers comments 3 Min Read

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

Topics: Crossdressing, Sissy, Landlord

6.2
75 Votes

Boy to Bride (Feminization Novella)

Story by Sissy Scarlet

8 Jun 2018 24265 Readers comments 7 Min Read

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!

Topics: Crossdressing, Sissy, Feminization

7.3
29 Votes

Good Lumberjack, Bad Lumberjack

Story by Sissy Scarlet

26 May 2018 3391 Readers comments 4 Min Read

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

Topics: Asian Men, Crossdressing, Slut, Alpha Male, Sissy

5.4
20 Votes

Chrissy's New Life

Story by sluttybttm4u

17 May 2018 5763 Readers comments 2 Min Read

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

Topics: Crossdressing, Sissy

8.0
91 Votes

Abandoned Parking Lot (ch. 2)

Story by Sissy Scarlet

9 May 2018 20507 Readers comments 2 Min Read

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.

Topics: Crossdressing, Sissy, Drunk