Gay Crossdressing Stories

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

Gone fishing

By Gpasboi 21 Jan 2021

He told me that he had put some clothes on my bed that I could wear for the night until my stuff had a chance to air out. When I walked in my room there on the bed was a white tshirt and a pair white silk panties with lace trim and I yell to Jim what the hell is this ?

8.4 (64) 12426 12 Min Comments

Daddy's Surprise

By Thormand1963 19 Jan 2021

Bisexual man gives his meet-up Daddy a crossdressing surprise

8.7 (38) 5102 8 Min Comments

The truck driver (ch. 3)

By bijim 23 Dec 2020

the final of my story being taken by two truck drivers and turned into a sissy bitch,

9.4 (43) 6464 21 Min Comments

When I found out I was really a whore

By desire_e4bbc 22 Dec 2020

How I truly became a crossdressing whore and loved it

8.7 (23) 4564 4 Min Comments

Daniel Effeminate College Student (ch. 14)

By Colourfast 14 Dec 2020

A series of stories about effeminate college twinks and their encounters with mature gentlemen

8.9 (6) 1162 22 Min Comments

Tell Tales Of A Jock

By Labeautifull 13 Dec 2020

A college Quaterback is caught all dolled up in Ladies Langerie by his Roommate who happenes to be the Wide reciever of their Team.

8.9 (40) 4031 29 Min Comments

I Would Never Kiss a Guy (ch. 4)

By GabbyGurl 26 Nov 2020

Gabby makes a major lifestyle decision and visits Nate.

9.4 (30) 3942 9 Min Comments

I become Amanda in Prison

By Amanda 12 Nov 2020

A fantasy tale of a spell of incarceration

8.3 (29) 12654 5 Min Comments

1st BBC

By Danielle 30 Oct 2020

When I realized rge saying "once you go black you never go back is true"

7.2 (47) 31173 5 Min Comments

The Girl Within Me

By Caliban 7 Oct 2020

Ninh’s first feminine adventure has an unusual consequence, after ‘she’ meets Allister…

9.4 (136) 5431 17 Min Comments

Hungry for more

By Karl 5 Oct 2020

On the prowl after getting a taste for gay sex

8.4 (22) 2945 4 Min Comments

The Kiss

By Nils Huim 11 Sep 2020

A pair of sex partners, one of them a CD, invite a third man over

7.7 (6) 1060 9 Min Comments

My second encounter with a guy whom I met in metro

By Hema CD 9 Sep 2020

My second encounter in gay sex with a guy whom I met in metro. Read how we connected met and read the story in detail to know more about the encounter

7.1 (8) 1319 5 Min Comments

101

By Nils Huim 27 Aug 2020

A gay bottom has a sexual adventure with a stranger

7.6 (42) 12982 6 Min Comments

A Harmless White Nylon Thong

By nylonlingerie 3 Aug 2020

I received a small parcel through the post, not ordered anything from any mail order, so I carefully opened it..

7.0 (56) 22078 4 Min Comments

A Sissy Life

By Faedirk 7 Jul 2020

Cat-sitting for your neighbors becomes alot more exciting when you stumble upon their wardrobe collection.

9.2 (118) 26410 14 Min Comments

Meetup Gone Crazy

By Luke Holton 16 Jun 2020

After I met a guy at his hotel, him and his team tie me to a bed and chloroform me. Read to find out what happens next

8.2 (21) 5460 11 Min Comments

Failed Connections

By Habu 12 Jun 2020

It's all about the pro soccer player's need in fetish play in Denver and Chicago.

9.4 (21) 2787 43 Min Comments

my life (ch. 17)

By bijim 10 Jun 2020

a club dancing and developing a crush on a guy

9.7 (15) 2607 9 Min Comments

Gay sex change?

By Rubbertransformation 31 May 2020

I love taking cock but often wonder what it would be like to have a pussy instead!

9.0 (38) 8324 6 Min Comments

Turn About is Fair Play

By Mikal 30 May 2020

Turn About is Fair Play is a Caesars Bitch Sweet Chrissi cross over both are Detroiters and Jay Jay is mentioned in my 1st Sweet Chrissi as JJ. Anyway Caesar takes his cross dressing sissy boyfriend Jay Jay out they meet Chrissi and things get real naughty.

8.0 (5) 528 6 Min Comments

Sweet Chrissi (ch. 5)

By Mikal 29 May 2020

Dear Rears I really struggled with the decision to allow the Pandemic to be an element in my story. But I am writing a story about a cute sissy that lives in Detroit which has been impacted heavily and so I included it.

9.2 (11) 2419 3 Min Comments

Muscleboy Double-Teamed in the Gym Shower (ch. 3)

By GameBoy94 9 May 2020

The second part of Jake the muscleboy's steamy molestation on a late-night train car.

9.6 (27) 7181 21 Min Comments

I Love Being a Faggot

By cock whore kimmy 5 May 2020

Gary is a cross dressing sissy faggot, and his love of hot, thick, juicy, stud cock has turned him into the biggest little faggot sissy whore! He’s not happy until he’s left cock drunk, with his face covered in cum, and his little asshole is sore and gaping! What a little slut!

7.5 (18) 7246 7 Min Comments

Caesars Bitch (ch. 2)

By Mikal 29 Apr 2020

This is a new installment of Caesars Bitch. In this tale Caesar has been with Jay jay for a time and is starting off on his first romance and is cementing his relationship. Yes there is abusive language but we are all grown ups so if you can't handle it move on.

8.8 (17) 2824 6 Min Comments

Living my dream (ch. 2)

By SissyBoi 16 Apr 2020

Cute 18 yo femboy crossdresser meets a real man who gives his little boypussy a proper stretching and makes him his bitch

8.8 (34) 8604 9 Min Comments

Sacked Quarterback

By Cracker 7 Apr 2020

A macho star quarterback goes from a chick fucker to a cross dressing chick-with-a-dick who gets fucked.

8.4 (42) 4697 9 Min Comments

Sissy Transformation

By Mikal 5 Apr 2020

Hi everyone I'm sure many of you are at home board and horny right now. Well I hope I can help relieve some of you with this story about a closeted sissy who meets a mistress that helps him find his true sissy self after he gets in debt to her.

8.3 (21) 6530 4 Min Comments

The end of a perfect night out as a sexy woman

By Bob Long 1 Mar 2020

This was the last but ultimately the best part of evening when my girlfriend took me out to a gay club, dressed as a woman just to test the water and to assure me that I not only very passable but also pretty damn hot. I got way much more than I imagined

8.4 (12) 3375 11 Min Comments

Gary: The Cock Hungry, Cum Guzzling, Sissy Faggot

By cock whore kimmy 27 Feb 2020

Kim comes home early from work and hears a whore getting fucked in her bedroom. She can only assume her BF Gary is in there cheating on her. So she slips in to catch him in the act, but what she finds in nothing like what she thought. She finds Gary all alone, lying on the bed. He’s wearing some of her sluttiest clothing, and trashiest lingerie. And he’s fucking himself with her favorite dildo.

8.0 (52) 7926 26 Min Comments