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.

Bits and Pieces: A Rossford Book (ch. 21)

By Chris Lewis Gibson 26 Apr 2026

As the chapter ends, we learn that you can take the porn star out of porn, but you can't take the porn star out of Paul Anderson

9.2 (3) 18 6 Min Comments

I keep coming back for more

By BillyBoy 22 Apr 2026

He told me he was surprised I wanted to come back for more. I couldn't answer him because I don't know myself.

6.5 (8) 607 4 Min Comments

Finally met a guy i could kiss

By BillyBoy 15 Apr 2026

A married straight couple invited me for some fun. Turns out she wasn't into doing anything but giving orders and watching. He was into wearing her underwear, and into me.

7.1 (9) 527 1 Min Comments

Bits and Pieces: A Rossford Book (ch. 15)

By Chris Lewis Gibson 9 Apr 2026

Paul arrives in California, and all is not well.

9.2 (3) 88 9 Min Comments

Feeling Good in My Skirt and Heels (ch. 3)

By Prettyboy 6 Apr 2026

Jackie's new pink leather skirt has just arrived. After fucking himself with his dildo he hooks up with a leather man who is turned by femboys and Jackie in his pink leather skirt and knee high white patent leather boots

6.6 (3) 650 3 Min Comments

Crossdressing and bondage

By BillyBoy 26 Mar 2026

I finally found a guy to help me with my fantasies. Then this happened!

8.3 (8) 1220 4 Min Comments

Bits and Pieces: A Rossford Book (ch. 10)

By Chris Lewis Gibson 18 Mar 2026

A lot's been going on. At last we're back on track as chapter 4 begins

7.7 (4) 76 11 Min Comments

The Cunting of Lucas (Lucy) (ch. 5)

By GWSHomo 18 Mar 2026

Lucy's first day with her newly formed cunt comes to a close. But will tomorrow bring new challenges?

8.2 (19) 2467 8 Min Comments

The Cunting of Lucas (Lucy) (ch. 4)

By GWSHomo 17 Mar 2026

He got up and pulled me off the bed. Leading me upstairs where he said he had lunch waiting. We both sat at the table. Me still feeling the aftermath of his fucking. He tossed me a small pillow. Which seemed to help a little.

9.0 (25) 2687 11 Min Comments

The Cunting of Lucas (Lucy) (ch. 3)

By GWSHomo 16 Mar 2026

It is time fir Lucy to have her new cunt molded and shaped into the perfect hole to fuck.

8.6 (23) 2728 13 Min Comments

Jessica

By KellyGirl2010 3 Mar 2026

My friends roommate...

9.6 (4) 1804 37 Min Comments

Contender Match: Phillip the BlondeAlphaSadist v. BeefcakeBobbyHawk

By vinnymusclestallion 1 Mar 2026

The photo showed a gorgeous blue-eyed stud with dark brown eyebrows with a mop of unruly blonde hair with dark roots.  He looked to be in his mid-20s.  His chest and abs were smooth and well-defined.  He had large brown nipples.  He had raised one muscular tatted arm to reveal cropped dark brown armpit hair....

9.6 (7) 660 6 Min Comments

Being owned (ch. 6)

By Chocolate_Boo 19 Feb 2026

Taking control of his/her whole being

8.8 (17) 2342 4 Min Comments

Champ Luis Cortez v. Tino Gavras aka Samson (ch. 6)

By vinnymusclestallion 19 Feb 2026

Cortez held Samson against his washboard abs.  Then he twisted the once Mighty Gladiator upside down.  With Samson’s face buried in Luis’s junk, the Champ thrust his hard 11” cock between Tino’s lips and into his throat.  The crowd roared at the sight of Gavras impaled upside down on the Champ’s big dick.

9.3 (10) 354 11 Min Comments

Champ Luis Cortez v. Tino Gavras aka Samson (ch. 5)

By vinnymusclestallion 18 Feb 2026

Samson reached again for the waistband of the Champ’s Speedo.  This time, however, he also grabbed the front of Luis’s poser.  He yanked both back and the crowd went wild at the sight of Cortez’s black pubic hair and semi-hard 11” cock.  Then Samson delivered another gut-punch—POW!—that rocketed the 19-year old’s body.

8.4 (13) 331 10 Min Comments

Men, Bondage and Discipline

By BillyBoy 18 Feb 2026

how i started becoming a sub bitch for so many dom men

8.1 (13) 1962 6 Min Comments

Bits and Pieces: A Rossford Book (ch. 9)

By Chris Lewis Gibson 17 Feb 2026

In the present, Sheridan and Brendan return from a party Elias is curious about, and in the past Elias remembers his first guilty encounters with Dylan Mesda

8.9 (7) 51 5 Min Comments

Champ Luis Cortez v. Tino Gavras aka Samson (ch. 4)

By vinnymusclestallion 17 Feb 2026

DeLovely removed each man’s red Speedo.  She had hogtied the naked Jorge with his own rope, exposing his big brown ass cheeks.  Naked Carlos was on his knees.  His wrists were bound by rope and pulled upwards in a “V” shape where they were tied to piping in the exposed ceiling.  His 9” cock dangled downward below his hairless pubic area.

9.3 (13) 372 12 Min Comments

Being owned (ch. 5)

By Chocolate_Boo 16 Feb 2026

Daddy didn’t even let me stand. He grabbed my wig, dragged me across the hardwood on my knees, latex catsuit squeaking with every frantic inch.

8.4 (17) 2028 4 Min Comments

Being owned (ch. 3)

By Chocolate_Boo 12 Feb 2026

Free use of a sissy and forcing drugs

8.5 (28) 4075 4 Min Comments

Being owned

By Chocolate_Boo 10 Feb 2026

Sissy being owned for the first time

8.1 (36) 5370 4 Min Comments

Black Alpha now owns me as a gloryhole slave

By tiffanyobeys 21 Jan 2026

Tiffany tgirl find her destiny as a cheap , gloryhole slave

7.6 (16) 3464 17 Min Comments

Big black Ass Grandma and Son (ch. 2)

By Dondee 21 Jan 2026

Fucked by the football team

6.8 (13) 2015 9 Min Comments

I Love my Bitch in Heels (ch. 2)

By Prettyboy 7 Jan 2026

Jake loves to top his bitch Jeff wearing boots whileJeff wears a skirt and boots with 3" heels. Jake leaves his cum in Jeff with his hole sealed with a jeweled butt plug. He takes the plug out in the morning and pisses on Jeff ass in the shower.

6.7 (9) 1432 3 Min Comments

Caught Crossdressing

By BillyBoy 4 Dec 2025

You don't hear about these sorts of things actually happening, but they do, Caught by a pervy in my wife's panties and bra. Oh No!

9.1 (28) 5285 12 Min Comments

Tiffany trans begins her journey as a chained slave

By tiffanyobeys 1 Dec 2025

Tiffany begins on her new life as a chained sex slave. She will be trained as a human toilet and fisted/stretched and prolapsed

9.2 (13) 2595 10 Min Comments

Trans gurl Tiffany is abducted by powerful Arab men (ch. 2)

By tiffanyobeys 30 Nov 2025

The continuing saga of Tiffany Tgirl , abducted in to slavery by Alpha Arab men. In this episode , we see her becoming a human toilet

8.5 (8) 2260 4 Min Comments

The Party of Thirteen

By Barry 23 Nov 2025

After connecting with a former sexual partner on Grindr, went to meet him at his friend's place. Upon arrival, two other men were present. The Grindr date and the narrator had sex, but then the second and third men also had forceful sexual encounters with the narrator.

8.1 (22) 2888 7 Min Comments

The Chronicles of Alex

By Andrealegscd 21 Nov 2025

Alex is now 18 after many years of crossdressing and discovering his feminine self he is totally out and becoming more feminine by the day , taking hormones has aided the changes in his body and opened up lots of possibilities for sexual fun

7.8 (12) 1586 8 Min Comments

Playboys

By Victor 17 Nov 2025

A frat initiation goes sideways for one straight frat boy. Forced to waitress an alumni party while scantily dressed, brings a realization that he may be repressing his true sexual nature.

9.4 (42) 3609 41 Min Comments

Rocky Horror

By Victor 14 Nov 2025

Straight, frat boy Colt has never been to the Rocky Horror Picture Show, but his buddies assure him that it's perfectly normal to wear costume lingerie. When he catches the eye of an alpha Marine, he starts to wonder if he actually likes that attention he's getting dressed in slutty lingerie.

9.6 (90) 4496 29 Min Comments

Brother in Law (ch. 2)

By BabyBoiPussy 7 Nov 2025

I like wearing my sister’s lingerie. They feel so good on my skin. I usually just wear them in private but what I was doing today was very dangerous. I wait until the door unlocks at 2 am on Saturday morning, knowing he’s been drinking. Knowing also that my sister is on bed rest at the hospital for the baby. My own personal bedroom door is wide op

8.8 (103) 9649 3 Min Comments

Curious turns into first time guy on guy sex

By sissyjackie 5 Nov 2025

Was curious for years finely took the plunge had gay sex

7.6 (31) 5193 4 Min Comments

Does wearing pantyhose and a bra make me gay?

By BillyBoy 28 Oct 2025

Confused as to why I feel like I should be sucking a man's cock when I'm just wearing a pair of ladies pantyhose and a cute little push up lace bra???? Am I gay?

7.8 (10) 2341 7 Min Comments

Begging for Master's Filthy Creampie Praise (ch. 2)

By ANSH 15 Oct 2025

Ansh decides rules for Dhruv and how they are going to do. Dhruv receives his first task. Read more what happens next.

9.2 (14) 2137 6 Min Comments