Gay Crossdressing Stories

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

My Vegas trip

By Jester4fun 24 Apr 2023

My real Vegas trip:)

9.4 (196) 4082 10 Min Comments

He showed me I have a girl inside (ch. 8)

By Jerryisjulie 24 Apr 2023

Daddy’s hold on me gets stronger - my lessons continue

9.2 (37) 5256 4 Min Comments

Prom Dress Contest for The Boys

By BillyBoy 22 Apr 2023

Having all the sissy's in town show up wasn't as hard as I thought

5.8 (10) 2540 8 Min Comments

Bras, Bros and Blowjobs

By BillyBoy 21 Apr 2023

my study buddy caught me playing in my sisters underwear

7.5 (25) 6771 5 Min Comments

First time sex as a CD

By Jester4fun 21 Apr 2023

My dream come true

9.3 (193) 7387 5 Min Comments

When I was first getting started

By Famsammie 14 Apr 2023

Living at home with my parents still my eager 19 yr old was begging for some type of action late at night

7.2 (13) 4179 4 Min Comments

Being Used By Dad

By Phaggotry 10 Apr 2023

A crossdressing queer becomes a cum dump for his dominant father.

8.7 (57) 22299 13 Min Comments

I am the pervy Uncle

By BillyBoy 6 Apr 2023

Everyone has a pervy uncle, but it turns out, I am the pervy uncle

8.4 (34) 7045 17 Min Comments

Russian Roommate (ch. 3)

By TyPeirson 27 Mar 2023

After finally taking Danyl's cock, "Jess" is ready to submit totally. After a trip to the gym, things don't end up going according to plan, and Jess's level of submission to the life of being a sissy is tested.

9.4 (62) 9782 13 Min Comments

Sissy panty boy can't find a dom to fuck him

By BillyBoy 22 Mar 2023

Been looking. I guess guys aret really into a panyboy unless they are young and pretty. I'm not either of those. But I'm willing, obediant and fun!

8.1 (15) 2438 5 Min Comments

A simple mistake

By BillyBoy 20 Mar 2023

My wife catches me in her underwear. She tells her friends. One of her friends husband call me. Then it begins.

6.6 (48) 8089 2 Min Comments

Kept Men

By Habu 13 Mar 2023

Young Lawyer gives special service in building of Biltmore Estate

8.8 (29) 1959 33 Min Comments

Ron & Hema first encounter

By Hema CD 9 Mar 2023

Read how ron and hema had their first encounter. second part coming soon

6.1 (5) 596 9 Min Comments

A unexpected good time (ch. 2)

By Famsammie 5 Mar 2023

Waking up next to chelsea after a night with her brother mark and friend Lamar

9.0 (11) 2753 6 Min Comments

My Father Loves My Trans Ass

By Phaggotry 3 Mar 2023

Arin knew his father never liked him. His other sons were men and Arin felt more like a girl and dressed accordingly. Her world starts to unravel when things goes bust with her boyfriend and her father decides to violently pluck her cherry.

8.0 (43) 14373 12 Min Comments

The bully (ch. 3)

By Darksicko 1 Mar 2023

I pressed my lips like a kiss on his asshole and pressed my tongue in. His tight hole pushed it out right away and a hand grabbed my neck. I kept at it and after ten presses his but started letting me in.

8.2 (23) 5462 6 Min Comments

It all started with an innocent blowjob (ch. 2)

By Viki 28 Feb 2023

It is a story of a young gay man discovering his needs and desires. Experimentation and first encounters, experiences, and something more.

8.8 (19) 2798 37 Min Comments

Swingers trick me into being their bitch

By BillyBoy 28 Feb 2023

Bob and Lacey invite me over to join their swingers' group. But I'm alone with them.

7.2 (25) 4978 3 Min Comments

my sissy encounter turns into a bondage fuck-fest

By BillyBoy 27 Feb 2023

Greg searches for submissive sissy type guys on the dating sites. He messages me, seduces me, dresses me in silk and lace, and begins playing in some light bondage. Then he introduces me to his Dom daddy, Bob

8.7 (28) 6066 5 Min Comments

I'm aged but still horny

By Italian sub Cindy 21 Feb 2023

Aged but horny dominanca and submission lover

6.8 (12) 1950 5 Min Comments

The Sissy Transformation of Christian

By TheNaughtySlut 18 Feb 2023

Christian has turned 18 Years Old, and his friend's sister is interested in him. What happens next nobody could anticipate, Christian becomes a sissy cock-loving cumslut. But how does this happen? Find out by reading The Sissy Transformation of Christian.

8.9 (45) 8721 13 Min Comments

Sale of sissy slave Cindy her poem

By Italian sub Cindy 9 Feb 2023

letter from Domina Anna for Cindy total submission

5.6 (5) 1074 2 Min Comments

Sexy CD's first gay encounter (ch. 2)

By fanny 6 Feb 2023

After our first encounter, he was getting hungry again for some of my ass. After a month, I saw some new packages was sent to me. As I opened them, noticed there are some new sexy lingeries and dresses with panties.

7.9 (13) 1723 2 Min Comments

Cabot's Adventures

By satyrDaddy 29 Jan 2023

An elder gentleman finds new lust

7.7 (12) 2073 6 Min Comments

Neighborhood faggot boy (ch. 3)

By Alleykat 29 Jan 2023

I used to be just an innocent Kidd now I’m a Heather 4 my daddy n his friends. And they know where I live

9.1 (47) 9952 3 Min Comments

Princess and King Show Off

By BeefyFem 27 Jan 2023

Every household needs both roles determined. I’m the husband, you’re the wife. You’re my Princess, I’m your King. This is the dynamic King and Princess decide to show off to the world.

8.4 (15) 2488 6 Min Comments

Hendry

By satyrDaddy 18 Jan 2023

Hendry is an ambitious femboy

7.2 (11) 2531 2 Min Comments

He Wanted Sex In Lingerie

By Jjj1975x 5 Jan 2023

I am a married man who met a guy at a party. The guy wanted to have sex with me in lingerie. That is, he wanted me to wear lingerie. I didn’t think I would like it. But it was amazing.

8.8 (28) 5803 15 Min Comments

Cd curious of what a homeless man is packing

By Famsammie 19 Dec 2022

Everyday to work I would see the same homeless pitching quite the tent in the morning from sweat pants

8.9 (54) 8113 7 Min Comments

CD meets BBC first time

By Famsammie 12 Dec 2022

When he said I don't know I think 6 inches when I asked how big, I should of known that was a lie

8.7 (45) 9333 6 Min Comments