Page 3, Gay Crossdresser Stories

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) 4866 17 Min Comments

Whispers by the Waves (ch. 4)

By gorillaz1993 14 Aug 2025

Their final morning together in the cabin, Alex decides to thank Marcus in his own way...

9.4 (19) 1171 5 Min Comments

Alex untied it curiously, lifting the lid to reveal black fishnet stockings and a pair of matching black lacy panties, the delicate fabric intricate and sheer. His eyes widened, a flare of nerves twisting in his stomach...

9.0 (18) 1621 5 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) 3978 7 Min Comments

None as much

By Luvonstkylip 2 Aug 2025

How i changed, sides!!!!!

7.5 (22) 2703 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 (50) 7273 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.

8.3 (19) 2901 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 (40) 7116 3 Min Comments

Tom, the married security guard took me for a woman (ch. 4)

By Sufficient_Offer 5 Jul 2025

It's Friday, campus is pretty empty but I'm about to meet Tom, the married security guard that is pretty impatient to train my poor throat all night long.

9.7 (40) 5350 9 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) 2938 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 (154) 9832 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) 3405 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 (48) 7843 32 Min Comments

21 Birthday

By Don 7 Jun 2025

Taking a friend out for his birthday

6.6 (28) 2550 2 Min Comments

Abusive Sissification (ch. 4)

By Kavya sissy 7 Jun 2025

It’s an incident where I was fucked raped and brutally tortured by a gang of 8 strong men and slowly turn me into their sissy whore

8.0 (41) 17469 5 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 (75) 5108 28 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) 5160 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) 5241 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) 1577 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.

8.9 (26) 5226 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 (67) 4505 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

8.0 (6) 2943 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?

8.4 (48) 5817 4 Min Comments

Hassan My Mom's Arab Boyfriend (ch. 5)

By Catwithapen 6 May 2025

As Hassan is out for an event, Chris is all alone at home—half-dressed, the night humid and still. But the quiet shatters as masked intruders break in, pinning Chris down, stealing more than just valuables. Just when all seems lost, the door bursts open—Hassan, seething with fury, charges in like a storm, fists flying to reclaim his pet boy

8.7 (44) 8086 19 Min Comments

Sissy Exposes Herself at the Cruising Park

By Bi_and_curious 5 May 2025

Married bi curious sissy decides to be a naughty little exhibitionist at a local park known for old pervs cruising.

7.4 (20) 5585 12 Min Comments

Straight friend from the military orchestra uses me (ch. 5)

By Sufficient_Offer 29 Apr 2025

Ivan comes back with a huge case of blue balls and an urge to fuck some good pussy. I oblige and give him the best possible hospitality.

9.6 (45) 5502 12 Min Comments

Loving my high heels (ch. 4)

By Prettyboy 28 Apr 2025

Jackie loves wearing boots with high heels. He meets Jeff who is looking to fuck a femboy and and gets hard seeing Jackie in his knee high white patent leather boots with 3" heels. They have some hot booted sex.

7.5 (7) 431 4 Min Comments

Saving The Twink and ...

By Mr.X 27 Apr 2025

WARNING: This storyline will depict thoughts of suicide, adventure-like spy-espionage, violence, guns, weapons, blood, gore, death, and military combat. 18-year-old Carter must save his mom with surgery, which is unattainable. He will have to borrow from dangerous men. As fate would have it, he meets Ethan, who is a retired 48-year-old spec intel

9.7 (100) 8420 40 Min Comments

My full time journey

By Jester4fun 18 Apr 2025

The story of how and why I went full time feminine

9.2 (49) 4103 7 Min Comments

Caught Crossdressing

By BillyBoy 15 Apr 2025

in her underwear, I'm exposed and turned into his cock slave.

5.9 (13) 5862 2 Min Comments

Gave in and got the BIG cut

By Frank Chainges 11 Apr 2025

41 year old single gay guy, Waited 30 years to get this done so I can carry out my life as I wanted years ago.

5.9 (17) 2275 2 Min Comments

He came up behind me

By sandybotm 31 Mar 2025

You never know what can happen when you chop veggies in a skimpy outfit.

8.4 (23) 3275 4 Min Comments

Fantasy fulfilled, or nightmare realized

By Dirty_Thoughts 28 Mar 2025

Fantasy fulfilled or nightmare realized, closet crossdresser gets more than they bargained for...or did they.

7.4 (32) 4151 10 Min Comments

Tricked into actually being his bitch

By BillyBoy 11 Mar 2025

He was suppose to untie me but he had other ideas first

7.8 (52) 11607 5 Min Comments

Caught in her panties by my mean stepfather

By BillyBoy 6 Mar 2025

George finds me in panties. Then the real trouble really begins

7.7 (43) 7779 4 Min Comments

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.