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.

Gary's Choice (ch. 13)

By Major Tom 17 Jun 2020

"Now that I feel that mouth on my dick, I'm sure! This is the pro my firm used to hire to relieve us during late nights. Oh yeah! I know this tight ass so well." A family gathering went off in other directions.

9.2 (16) 1601 4 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

7.9 (23) 6100 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 (22) 2896 43 Min Comments

Gary's Choice (ch. 12)

By Major Tom 12 Jun 2020

"I did what needed to be done..." There was a new business venture.

9.2 (14) 1771 3 Min Comments

my life (ch. 17)

By bijim 10 Jun 2020

a club dancing and developing a crush on a guy

9.7 (15) 2744 9 Min Comments

I love My Dirty Daddy (ch. 2)

By Mikal 9 Jun 2020

Lola's Dirty Daddy Eric decides to give a lecture about sissy's to novice doms and share his little sissy with them.

9.0 (19) 4767 7 Min Comments

my life (ch. 16)

By bijim 5 Jun 2020

going to the doctors and taken out in public for the first time,

9.1 (18) 2430 5 Min Comments

Gary's Choice (ch. 10)

By Major Tom 3 Jun 2020

"None of us has shame. We can't afford shame, Anyway, all that's over. Tim's settled in at that factory and it's all's good." "I had tried to block that out. It was the most horrible thing I was responsible for."

9.0 (21) 1920 5 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 (40) 9057 6 Min Comments

my life (ch. 15)

By bijim 31 May 2020

more abuse from bill a double penetration surprise and falling for a milking machine

9.4 (17) 1882 7 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) 566 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) 2476 3 Min Comments

Gary's Choice (ch. 9)

By Major Tom 29 May 2020

"'Good boy!' He did some blow. 'Want some?' 'Yes sir, please.' He spread two lines on his fat dick that I had just been sucking on. I put my face down and snorted it off him. "Thank you, sir." I was buzzed and horned to take his prize tool up my ass."

9.0 (19) 2368 6 Min Comments

Those tough Marines are just as queer as the rest of us! (ch. 5)

By jon martin 27 May 2020

Stan has some downers and uppers.

9.1 (27) 1609 3 Min Comments

Gary's Choice (ch. 8)

By Major Tom 25 May 2020

"I sat at the kitchen table not believing what my shaking father was trying to explain to me. The only way out was for one of us kids to become a sex worker and work the debt off. I did what I was supposed to do and said yes." More from Timothy.

9.3 (18) 2244 6 Min Comments

my life (ch. 11)

By bijim 15 May 2020

we meet the owners and get acquainted to these remarkable people

9.6 (13) 886 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 (29) 7932 21 Min Comments

Crossdressing faggot meets a brutish construction worker

By Alex Walker 8 May 2020

A crossdressing fag makes a mistake that catches the attention of a burly construction worker and is invited over for some fun.

9.1 (76) 13978 6 Min Comments

Muscleboy Double-Teamed in the Gym Shower (ch. 2)

By GameBoy94 8 May 2020

Jake the muscleboy finds himself longing for another encounter like the one he previously had in the gym shower. He also starts wearing tight girly clothes underneath his regular attire to prepare for such an encounter. Little does he know that his deepest, most perverted fantasies are about to come true (again).

9.3 (18) 6151 18 Min Comments

Nocternal Eminations

By Mikal 7 May 2020

A story about being abducted and fucked by demons.

8.1 (14) 2744 9 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!

7.6 (22) 8577 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) 2894 6 Min Comments

Caesars Bitch

By Mikal 24 Apr 2020

Caesars Bitch is combination of a Cross Dressing & Sissy and First timer story. While I normally tell a story from the bottoms prospective I'm trying to expand my creative horizons and telling a good portion of this kinky tale from the Top Caesars prospective. it is also my sincere hope that you enjoy this tale and tell me what you think in the comments box.

8.7 (27) 2096 6 Min Comments

Sweet Chrissi

By Mikal 19 Apr 2020

A short story about a fem boy.

8.8 (46) 4753 8 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 (35) 9361 9 Min Comments

Sweet Chrissi (ch. 4)

By Mikal 8 Apr 2020

While this story fits in the Crossdressing/Sissy catigory it is also a BDSM story. In Sweet Crhissi Chapter 4 Naughty Sissy's get Punished Chrissi is caught in bed with another man by his boyfriend Steve and there is Hell to pay.

9.3 (8) 1353 6 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) 4999 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) 7223 4 Min Comments

Fighter Pilot's Pussy

By Clark Wayne 4 Apr 2020

Bi fighter pilot comes home to find his fighter pilot fuck-buddy waiting for him in sexy lingerie.

9.3 (125) 12940 25 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) 3521 11 Min Comments

Sweet Chrissi (ch. 3)

By Mikal 19 Feb 2020

Bored and in need of some dick Chrissi gets a surprise visit from a fellow sissy boy friend Daisy and it leads to a three way.

8.2 (13) 1062 7 Min Comments

Broken

By Clark Wayne 17 Feb 2020

Straight man is attracted to an alpha. He becomes the alpha's toy. He tries to rebel but his new Alpha has decided to fix his attitude and humiliate him. If the closeted straight guy wants to get fucked, he'll have to wear some panties to show his devotion.

8.7 (111) 12552 6 Min Comments

Before she turned me out

By Bob Long 10 Feb 2020

My girlfriend who fostered my obsession with crossdressing and living as a woman, trained and made me into one hell of a beautiful woman who eventually sucked a mans cock and loved it

7.8 (30) 8446 51 Min Comments

How I got started (ch. 3)

By Bob Long 5 Feb 2020

Our continuing story of the greatest time of my life exploring and fulfilling my deep seated desire to be a woman through crossdressing and learning about my sexuality with the best teacher in the world my mom

8.3 (17) 1302 19 Min Comments

How I got started (ch. 2)

By Bob Long 4 Feb 2020

This is a continuation of my glorious introduction to crossdressing and sex

7.8 (6) 2210 23 Min Comments