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.

My first time with Terrell

By pawb bunny 14 Oct 2024

White 18 year olds first time having sex and its with a sexy 26 year old black man

9.0 (80) 9117 9 Min Comments

Closet crossdressing goes very wrong, or did it?

By BillyBoy 10 Oct 2024

Dressed in private but I have to answer the door for my neighbor. It turn out to be a very naughty afternoon.

8.2 (36) 7767 6 Min Comments

CD Hotel sex

By Jester4fun 3 Oct 2024

Sissy CD takes dick in hotel

9.3 (137) 13192 8 Min Comments

Spit roasted at home

By BillyBoy 12 Sep 2024

He had me cuffed, wearing a humiliating pink frilly outfit, with a huge nasty purple veined rubber cock in my mouth, and his fat cubby cock fucking my ass from behind. John was kind enough to fulfilled my fantasy for me.

8.7 (31) 5480 4 Min Comments

Cruising

By Danni 5 Sep 2024

Falling in love sucking strangers in public it’s scary dangerous but sooo EXCITING

8.2 (35) 4611 6 Min Comments

Miss Jenny from Ohio (ch. 4)

By Okamaguy 28 Aug 2024

Jenny spends the day as a schoolgirl and gets more cock than she bargained for.

9.5 (11) 3345 16 Min Comments

Miss Jenny from Ohio (ch. 3)

By Okamaguy 27 Aug 2024

Jenny goes from schoolgirl sex to truck stop sex..and loves it all

9.4 (9) 911 33 Min Comments

Miss Jenny from Ohio (ch. 2)

By Okamaguy 26 Aug 2024

Day 2 of Miss Jenny's adventure in rural Japan. She gets all the cock she wanted and a liltle more than she bargained for..and keeps uncle and granddad happy.

9.6 (8) 1273 22 Min Comments

Miss Jenny from Ohio

By Okamaguy 25 Aug 2024

I go to stay with a female friend's male relatives in rural Japan, end up becoming Miss Jenny from Ohio, and get to sample most of the local manhood.

9.6 (27) 2651 12 Min Comments

Bound Gagged and Gay'd Me

By BillyBoy 23 Aug 2024

He answered my ad, answered my fantasies, and answered my question: Was it good for you?

8.8 (21) 5463 8 Min Comments

How I became an adult bookstore slave

By Filthyslagbag 21 Aug 2024

How I became a bookstore sub

8.9 (118) 13060 5 Min Comments

Cruising the Highway

By deansaz 2 Aug 2024

Just on a short drive down the highway when a couple girls began flirting with me from another car on the highway.....

8.3 (26) 2905 3 Min Comments

College and finding the real me

By KellyGirl2010 29 Jul 2024

After graduating high school, I try to figure out who I am and I find that in the arms of another man. Parts of this story are true like my first time panty shopping, going to the adult bookstore, my brother knowing about me wearing panties and the college LGBT Center.

9.1 (31) 4194 23 Min Comments

Call Me a Fuckin Fruit

By Prettyboy 28 Jul 2024

Jackie is wearing a new pair of pink leather shorts with the hopes of attracting a horny top. Jim is a turned on by Jackie's shorts and enjoys her ass both in the gorgeous pink leather and also in the flesh.

7.5 (12) 1283 5 Min Comments

Finally giving in

By ClosetCd 28 Jul 2024

A married husband finally giving in to his desires

9.1 (99) 7818 6 Min Comments

Wearing panties

By KellyGirl2010 25 Jul 2024

Sucking my first cock

8.3 (28) 9787 7 Min Comments

BDSM lovers

By BillyBoy 24 Jul 2024

I wander into a sex shop for gay BDSM lovers. I'm in the wrong place!

9.0 (48) 4007 6 Min Comments

Just to Dream a Dream

By luvaslip 20 Jul 2024

Terry arrives at her uncle's house early and lays down for a nap. She dreams a dream that becomes real and gets a lot of loving.

9.0 (14) 1422 2 Min Comments

Twins bothers have lot more in common (ch. 3)

By Xoxo 19 Jul 2024

Harry gave his BBC friends a little show

8.9 (10) 2652 7 Min Comments

Can I go back to my favourite club? (ch. 2)

By Frankfurt Chronicler 17 Jul 2024

Our narrator's adventure at his favourite club continues with an unexpected sexual encounter while the band plays.

9.6 (17) 2053 13 Min Comments

Jocks and Panties

By Victor 17 Jul 2024

Branson is a big, muscular, athletic jock who can't understand his need to be treated like an another man's bitch.

9.6 (90) 8465 19 Min Comments

Can I go back to my favourite club?

By Frankfurt Chronicler 16 Jul 2024

Our narrator has an unexpected sexual encounter with two men at the club while the band plays, losing his cherry and his pants in the same evening.

8.9 (24) 3167 11 Min Comments

Making the fantasy become reality (ch. 2)

By Try To Be Quiet 16 Jul 2024

Daddy had something planned for me this time, I wondered the whole week waht would happen during our next encounter

8.2 (14) 2514 8 Min Comments

Learning to be gay

By BillyBoy 3 Jul 2024

From playing in panties and shoving a dildo up my ass, I finally found a gay guy to fulfill my desires, fantasies and fetish needs.

8.0 (10) 3611 7 Min Comments

Loving my high heels (ch. 3)

By Prettyboy 27 Jun 2024

Jackie loves wearing high heels. He just received a pair of high black Chucks with 3" white heels. He meets Tom who is turned on by these Chucks and tops Jackie.

8.8 (10) 1029 4 Min Comments

Straight guy turned gay (ch. 6)

By Jaden 27 Jun 2024

A new experience - It was Monday morning, I woke up and found myself alone in bed. I found the sexy french maid outfit on bed. I wore it and headed to the kitchen. My master was having breakfast by himself.

9.5 (28) 8133 9 Min Comments

Bent Over

By RedJulian 25 Jun 2024

A cross-dressing bodybuilder slut awaits our narrator at the door.

8.5 (23) 3260 3 Min Comments

Swapping Spit

By luvaslip 23 Jun 2024

Joni joined the Marines and rented an apartment in Carlsbad. She takes a fifteen day leave and meets a neighbor who helps her.

8.5 (13) 1210 7 Min Comments

Straight guy turned gay (ch. 3)

By Jaden 22 Jun 2024

Turned into a sex slave.

9.1 (60) 12517 6 Min Comments

Twins bothers have lot more in common

By Xoxo 22 Jun 2024

Harry finds his brother suck neighbour BBC without sharing with him

9.4 (16) 4950 19 Min Comments

My first gay kiss

By KellyGirl2010 18 Jun 2024

My first hook up with a guy I met online!!

8.3 (17) 3176 2 Min Comments

Keds Bitch (ch. 5)

By Prettyboy 16 Jun 2024

Tom likes to top pretty femboys. He meets Jackie who just bought a pair of red Keds. Tom goes to Jackie's shoe store and buys a new pair of purple cowboy boots. Tom wears his new boots as fucks Jackie in his red Keds

7.0 (10) 627 4 Min Comments

Becoming Joni Kayse

By luvaslip 13 Jun 2024

Joni and her Uncle are on their way to colorado, on a graduation trip., there is some naughtiness on the way.

8.5 (33) 3920 5 Min Comments

Crossdressing Boot Bitch

By Prettyboy 13 Jun 2024

Jackie is a crossdresser and has new pair of women's knee high white patent leather laced boots and is looking for a top. Jackie hooks up with a leather boy, Jeff.

7.5 (17) 1308 3 Min Comments

Big black ass fucked (ch. 2)

By Dondee 11 Jun 2024

I was born with a big ass .I got fucked many tim

8.2 (2) 4273 8 Min Comments