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.

The System Inside (ch. 3)

By whiteboi 8 Sep 2026

Ash's understanding of the prison deepens a little as cracks open revealing the system to perhaps not be quite as it seems. He also finds himself being just as compelled to obey by his own body as he was by his superiors. Small mention of narcotics.

7.7 (8) 543 26 Min Comments

Luke and his Dealer (ch. 2)

By Stories by George 6 Sep 2026

Luke, a big former college jock discovers the pleasure of true submission when his dealer Caleb notices him eyeing his package and decides to let him have a taste of his big black dick.

9.2 (32) 1869 24 Min Comments

Fucked hard by my best friend’s boyfriend

By Lush Diego 5 Sep 2026

A gay boy dressed in latex seduces the hot boyfriend of his best friend.

9.5 (30) 1463 8 Min Comments

The System Inside (ch. 2)

By whiteboi 5 Sep 2026

Further character intro and world building for The System Inside since it was received well. Unfortunately this is not nearly as graphic or steamy, but more coming soon. I hope you like it. I am obligated to say there are, briefly, implied watersports.

8.4 (15) 794 19 Min Comments

My first time sucking cock

By Anonymous28 24 Aug 2026

Basically my first time sucking cock and a strangers cock

7.3 (15) 1135 2 Min Comments

Fucking a Cum Soaked Pussy

By Prettyboy 18 Aug 2026

Jed lives with his femboy partner, Jimmy. They fuck a lot. Jed enjoys fucking Jimmy again after he has dropped a load in JImmy's pussy.

6.6 (9) 1063 2 Min Comments

Intense Sissification

By That One Dominator 10 Aug 2026

It all started with a simple notification on my phone— an Instagram message from an anonymous group dedicated to connecting sissies with their daddies. They kept their profiles hidden, wrapped in secrecy, asking only for my deepest, darkest desires. Without hesitation, I bared my soul. I told them I was a secret sissy femboy, that I had a history of being a submissive bottom.

6.3 (7) 2408 22 Min Comments

Post-Practice Release 

By Stories by George 10 Aug 2026

When a lost bet causes a teammate to dress up it leads to a hot and unexpected encounter in the lockeroom between two teammates

9.2 (35) 1940 6 Min Comments

Loving my high heels (ch. 6)

By Prettyboy 2 Aug 2026

Jackie has just received a pair of white patent leather shoes from Shoe Freaks with 3" heels. After fucking himself with his dildo he meets Jimmy who fucks Jackie in her new heels.

8.6 (6) 394 3 Min Comments

How it all began (ch. 3)

By BirminghamBoy 22 Jul 2026

Sir rewards with an outfit and my first blowjob

8.2 (11) 1570 6 Min Comments

Twinkle little Slut (ch. 4)

By westside 9 Jul 2026

The continuing Sexual Adventures of Twinkle.

9.8 (7) 1803 61 Min Comments

Bulge & Panties

By Tyler Blake 8 Jul 2026

Desperate for cash, hung jock Gavin offers his broke roommate Toby $250 to wear panties and bend over for a quick video. One torn lace later, Toby’s virgin ass takes every thick inch. Raw, relentless, and way too good to stop.

9.4 (76) 4269 19 Min Comments

Raw Timber (ch. 9)

By Sufficient_Offer 5 Jul 2026

Bastien's landed a soft kiss on my neck, almost shy, then he flipped us gentle but firm, pulling me onto his broad bare chest so my face rested against his furry pecs, his massive arms wrapping around me tight.

9.8 (20) 1784 12 Min Comments

My Pretty Booted Bitch

By Prettyboy 28 Jun 2026

Jess is 38 and lives with his pretty bitch, Ricky. They both have fetish for boot and go on the Only Maker website and pick out a new pair of boots. They are calf high laced pink satin boots with 3" heels. When they arrive in the mail the new boots stimulate some hot sex.

9.2 (6) 672 3 Min Comments

Homo Hollow (ch. 8)

By Chip 12 Jun 2026

Hairietta arrives

8.7 (9) 494 3 Min Comments

Bits and Pieces: A Rossford Book (ch. 32)

By Chris Lewis Gibson 3 Jun 2026

Layla reflects on the love that brought her to this moment.

9.2 (3) 67 8 Min Comments

Bits and Pieces: A Rossford Book (ch. 31)

By Chris Lewis Gibson 2 Jun 2026

In which we learn a little bit more about fajita burritos

9.2 (3) 46 8 Min Comments

Stepbro Catches Secret Slut (ch. 2)

By ANSH 31 May 2026

His mouth was hotter than I expected. Wet and greedy and making these desperate little gulping sounds as I pushed deeper, the head of my lund dragging across his tongue like he'd been starving for it.

8.9 (19) 2694 7 Min Comments

Stepbro Catches Secret Slut

By ANSH 30 May 2026

Stepbro finds Josh's hidden lingerie and sex toys, snoops his phone for pegging erotica, then confronts him with chastity devices and filthy breeding.

8.4 (26) 5336 8 Min Comments

The Cunting of Lucas (Lucy) (ch. 12)

By GWSHomo 20 May 2026

A short interlude. But an important one on the side of Danny. Our Lucy's beloved daddy and conqueror.

8.2 (13) 1555 5 Min Comments

The Cunting of Lucas (Lucy) (ch. 11)

By GWSHomo 9 May 2026

Lucy learns her first lesson in self-care and choosing men on her own to serve.

7.4 (13) 1754 15 Min Comments

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

9.4 (4) 57 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.

7.6 (16) 2574 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.

6.6 (10) 1865 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.

9.4 (4) 203 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

7.0 (8) 1699 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!

8.2 (11) 3111 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) 89 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?

8.5 (31) 4862 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.

9.1 (42) 5527 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.

8.8 (41) 5983 13 Min Comments

Jessica

By KellyGirl2010 3 Mar 2026

My friends roommate...

9.3 (5) 3115 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 (8) 773 6 Min Comments

Being owned (ch. 6)

By Chocolate_Boo 19 Feb 2026

Taking control of his/her whole being

9.1 (23) 3983 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) 408 11 Min Comments