Gay Crossdressing Stories

GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.

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 (96) 5040 29 Min Comments

BBC Cum Diet (ch. 2)

By Sissyslutgurl69 12 Nov 2025

Part 2: Femmie whiteboi continues cum-only diet.

9.1 (29) 8674 12 Min Comments

Femoby catfished by a Femdom and her Lover

By Sissyslutgurl69 11 Nov 2025

Feminized sissy gets tricked by an aggressive mean Femdom.

9.2 (20) 4570 54 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

7.5 (33) 6242 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) 2840 7 Min Comments

I Love My Pretty Pink Boots

By Prettyboy 27 Oct 2025

Jackie has a fetish for boots and hi top sneaks. She has several pink boots that are a turn on for his partner Jeff. The story describe Jackie's day and the hot sex she has in her pretty pink boots.

5.3 (8) 516 4 Min Comments

Rahul's Sissy Awakening Under Master Ansh (ch. 7)

By ANSH 16 Oct 2025

The story comes to its final chapter read how both Ansh and Vikaram uses Rahul

8.5 (9) 1627 6 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.

8.5 (71) 6598 5 Min Comments

Romantic Fem Bottom

By sandybotm 9 Oct 2025

It's late at night. They need each other. Both horny for each other and can't wait. He loves being fem to a strong top.

8.8 (32) 3794 8 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

7.1 (22) 4352 2 Min Comments

Didn’t know it was a gay bar (ch. 3)

By Alleykat 27 Sep 2025

Drugs blackmail sissyboi

8.7 (55) 7303 6 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.

6.3 (14) 2242 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) 3261 8 Min Comments

Being A sissy Slave For Money

By yourboy68 5 Sep 2025

Story Includes sissy getting Multiple Sex, Public Sex, Rough and much more, enjoy reading and lemme know in the comments for improvements.

7.6 (42) 7452 6 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 (50) 11686 10 Min Comments

Crossdresser Slave Imprisoned

By tiffanyobeys 18 Aug 2025

Tiffany CD is welded in to chains , for a lifetime of serving strangers cocks - no escape

8.2 (16) 4559 17 Min Comments

I Love Cock

By Prettyboy 18 Aug 2025

Jackie loves cock in his mouth or up his ass. He lives with Jeff and who llkes Jackie tight shorts and high heels. The story describes a day in Jackie's life and how he gets fucked with a BBC in the afternoon and by Jeff in the morning and at night watching porn.

7.4 (27) 3002 4 Min Comments

I took 'her' to the prom

By BillyBoy 11 Aug 2025

A new younger friend said he always wanted to go to pram as a girl. I agreed and set it up

8.3 (20) 3853 7 Min Comments

Pretty Boys

By Prettyboy 10 Aug 2025

Bill loves pretty boys- blowing them, eating their asses, rimming them and fucking them. He connects with a pretty boy, Jeff, for some hot sex

6.1 (23) 2821 3 Min Comments

None as much

By Luvonstkylip 2 Aug 2025

How i changed, sides!!!!!

7.8 (21) 2600 3 Min Comments

Tom, the married security guard took me for a woman (ch. 5)

By Sufficient_Offer 21 Jul 2025

Tom wants to share Sam's dicksucking skills with his colleague Frank. Will two security guards be enough to satisfy Sam's hunger for straight cock ?

9.7 (49) 6961 11 Min Comments

New Pantyhose brought out my cross dressing fetish

By Frank Chainges 13 Jul 2025

Bought some new seamless tights (pantyhose) and they worked miracles for me and my new friend.

8.7 (16) 2761 3 Min Comments

Halloween is a great time to experiment

By BillyBoy 9 Jul 2025

My roommate suggested we try some crazy costumes and other fun stuff for this years Halloween party. I didn't know he was trying to seduce me. But it worked.

8.3 (39) 6892 3 Min Comments

New hormone tabs from the web

By Frank Chainges 29 Jun 2025

Need to improve my sissy, I am too masculine

6.9 (10) 2848 3 Min Comments

Jock Princess

By Victor 28 Jun 2025

My son's jock best friend wants to be daddy's side pussy.

9.3 (152) 9491 14 Min Comments

Night Drive

By vaportide 23 Jun 2025

A nervous first-time crossdresser drives to a motel for a late-night hookup with Daniel, a young top from Grindr (Part 1).

8.3 (20) 3308 4 Min Comments

Muscle Boy Girlfriends

By Victor 21 Jun 2025

Two football teammates at odds with each other find out they have some things in common: Muscle, domination, lingerie.

9.3 (47) 7612 32 Min Comments

I become a sissy to my daddy

By big ass faggot slut 20 Jun 2025

This is the story of how my daddy turned me, a already phat assed sisssy slut into a full time sissy housewife.

7.9 (60) 20154 6 Min Comments

Fan Meet and Greet

By Victor 18 Jun 2025

true story of me relenting to meet with a fan, a big, muscled, closeted, college athlete who was too perfect to pass up.

9.6 (73) 5309 15 Min Comments

Choose Your Fate

By Sissyboi69 11 Jun 2025

Three assaulter's are forced to decide what their punishments should be.

8.3 (52) 9588 8 Min Comments

21 Birthday

By Don 7 Jun 2025

Taking a friend out for his birthday

6.6 (28) 2513 2 Min Comments

Gym Bag

By Victor 7 Jun 2025

For extra income, two college jocks whore themselves out to men who like other masculine men in lingerie. One of them meets a man who thinks he's met the man of his dreams.

9.6 (73) 4967 28 Min Comments

Pretty in Pink (ch. 5)

By Prettyboy 7 Jun 2025

Jackie loves her Keds and hi top pink Chucks. She lives with Jim and wears pink leather shorts that are a turn on for Jim. They enjoy some hot sex together enjoying the pink shorts and boots

6.8 (6) 500 4 Min Comments

I'm no longer the man in charge

By BillyBoy 6 Jun 2025

A normal guy gives in to his wife's requests to dress in her lingerie, giving him the best sex ever, but it's all a lie

8.0 (47) 4926 6 Min Comments

First time used as a lingerie slut at the parking lot

By Bott in lingerie 3 Jun 2025

For a few years now I have had a sex fantasy to dress myself up as a slut, in ladies lingerie, and let a man use me. I am 29 years old and my fictitious name is Lin.

7.3 (20) 5026 4 Min Comments