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.

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.

8.6 (15) 393 10 Min Comments

Men, Bondage and Discipline

By BillyBoy 18 Feb 2026

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

8.5 (16) 3088 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) 63 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 (14) 431 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.

8.8 (22) 3398 4 Min Comments

Being owned (ch. 3)

By Chocolate_Boo 12 Feb 2026

Free use of a sissy and forcing drugs

8.7 (34) 6774 4 Min Comments

Being owned

By Chocolate_Boo 10 Feb 2026

Sissy being owned for the first time

8.4 (44) 8358 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 (19) 4775 17 Min Comments

Big black Ass Grandma and Son (ch. 2)

By Dondee 21 Jan 2026

Fucked by the football team

7.0 (15) 2760 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.

6.5 (11) 1690 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 (32) 7717 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

9.4 (19) 3678 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

8.0 (10) 2878 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) 3342 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

8.2 (14) 1910 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.

9.3 (51) 4441 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 (97) 5287 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 (112) 12187 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

7.4 (34) 6703 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) 3025 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) 2296 6 Min Comments

Rahul's Sissy Awakening Under Master Ansh (ch. 6)

By ANSH 15 Oct 2025

Read what happens between the 3 . How Rahul satisfies both Ansh and Vikram

8.9 (5) 805 5 Min Comments

Seduced by the 'lady' from corporate

By BillyBoy 15 Oct 2025

Gail works downtown, mostly from home. But tonight, she attended the business dinner. For some reason, I was seated next to her.

8.8 (40) 5970 5 Min Comments

Rahul's Sissy Awakening Under Master Ansh (ch. 5)

By ANSH 14 Oct 2025

Vikram continues to train Rahul with Ansh and goes on to train his submassive. To know what happens next read next..

8.7 (4) 972 5 Min Comments

Trans gurl Tiffany is abducted by powerful Arab men

By tiffanyobeys 14 Oct 2025

Tiffany , mature M2F trans gurl is snatched off the streets of London by wealthy , powerful Arab Dominants and led down the path of becoming the ultimate sex slave and human toilet.

6.7 (17) 3372 18 Min Comments

My first top experience

By Loves black men 12 Oct 2025

How a young curious male discovering his bisexuality met his first top. How a masculine man can be transformed into a cross dressing bottom in the bedroom. First time experience that lasted 10 and formed his love for BBC and the bottom experience.

8.6 (72) 6834 5 Min Comments

Rahul's Sissy Awakening Under Master Ansh (ch. 3)

By ANSH 11 Oct 2025

"I want to be a sissy master your sissy" Read how Rahul expresses his feelings to be his masters own pet.

9.2 (7) 1557 5 Min Comments

Rahul's Sissy Awakening Under Master Ansh

By ANSH 9 Oct 2025

The story continues of Rahul . Rahul has conveyed to master ANSH that he is irked by the idea of cd and wants to try read what happens and how the story unfolds.

8.6 (11) 2226 6 Min Comments

Used the wrong medication

By Frank Chainges 7 Oct 2025

Needed to enlarge my manhood and bought some meds off the internet.. results were NOT what I expected

6.7 (24) 4538 2 Min Comments

Feeling Good in My Skirt and Heels (ch. 2)

By Prettyboy 5 Oct 2025

Jeff loves seeing Jackie in skirts and has bought one for her in black leather. It looks so hot on Jackie they have sex. They go out shopping and buy a longer blue skirt with flowers with leads to another round of fucking.

6.3 (17) 1288 3 Min Comments

Feeling Good in My Skirt and Heels

By Prettyboy 26 Sep 2025

Jackie loves wearing her skirt and gets and erection when she puts it on. Jeff, her partner, loves seeing Jackie's lovely ass in in lace panties. On this day Jeff enjoys Jackie in pink laced panties and comes on them

7.4 (13) 2217 3 Min Comments

I Love Wearing Laced Panties

By Prettyboy 9 Sep 2025

Jackie got hard the first time she put on white laced panties and came in them. He partner Jeff is turned by Jackie wearing her laced panties and her pretty pink Nike boots. They enjoy sex with the white lace and pink boots and finish with Jeff pissing on Jackie's laced ass.

6.0 (15) 2311 2 Min Comments

My very first time broke the rules

By Remember 6 Sep 2025

This was my first unplanned encounter and he broke the rules,

8.9 (31) 3406 8 Min Comments

Black Alpha turns trans in to a human toilet

By tiffanyobeys 20 Aug 2025

Black man Jay is surprised to find he enjoys using sluts as human toilets and he binds and keeps sissy Tiffany eating , then sells her to strangers.

8.2 (32) 7355 7 Min Comments

Sissy trained to become black mens slave

By tiffanyobeys 19 Aug 2025

A Black Alpha binds and uses Tiffany sissy , then turns her out to dozens of other black Alphas who use her mouth and arse for their pleasure

8.9 (52) 12735 10 Min Comments