Gay Crossdressing Stories

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

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) 502 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) 1574 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.

8.6 (70) 6341 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) 3607 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

7.0 (21) 4119 2 Min Comments

Didn’t know it was a gay bar (ch. 3)

By Alleykat 27 Sep 2025

Drugs blackmail sissyboi

8.8 (53) 6888 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) 2119 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,

9.0 (30) 3140 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.

7.5 (40) 7063 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

8.8 (46) 10639 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) 4212 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) 2939 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) 3680 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) 2749 3 Min Comments

None as much

By Luvonstkylip 2 Aug 2025

How i changed, sides!!!!!

7.8 (21) 2493 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 (47) 6637 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) 2624 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) 6637 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) 2735 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 (148) 9127 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 (19) 3216 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.

9.2 (44) 7336 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.

8.0 (56) 18814 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 (71) 5165 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 (51) 9284 8 Min Comments

21 Birthday

By Don 7 Jun 2025

Taking a friend out for his birthday

6.6 (28) 2471 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 (70) 4818 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) 489 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) 4714 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) 4831 4 Min Comments

Joining femboy hooters strip club (ch. 2)

By Sluttyfemboy 2 Jun 2025

Cooks at femboy hooters on strike how will the femboys solve this issue with their femboy mouths or ass who knows? read.

5.8 (5) 1475 3 Min Comments

Sissy Call Girl

By ChasingRisque 30 May 2025

Jesse's life is falling apart -- until he turns his secret passion for crossdressing into a dangerous new hustle: escorting for men. Each rough, raw encounter drags him deeper into shame and desire, confusion and craving.

8.8 (24) 4679 29 Min Comments

Testing His Limits

By Victor 29 May 2025

Two college guys have a love/hate relationship. You can hate someone and still want to fuck them. The dominant Brendan wants the pretty boy Matt to realize just how much Brendan wants a girlfriend.

9.5 (60) 4230 16 Min Comments

Out for some fun turns into a rough night

By BillyBoy 28 May 2025

wearing girly underwear gets me in a lot of fucking trouble

7.7 (5) 2734 2 Min Comments

Caught and seduced

By BillyBoy 16 May 2025

The old guy working on my outdoor lighting recognized the webpage I was looking at. Later he called me to see if I might like to be his bitch. I wonder what I did?

8.5 (46) 5426 4 Min Comments