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.

9.5 (43) 2178 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

8.9 (3) 126 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

7.9 (18) 891 5 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.

7.4 (10) 982 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.

5.6 (3) 502 3 Min Comments

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.

7.9 (10) 981 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 (35) 1573 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

6.8 (3) 1006 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?

8.1 (35) 2555 4 Min Comments

Older man gave me my first sissygasm

By BeggingAndBlessed 16 May 2025

How a man twice my age gave me the best sex of my life and the first sissygasm of my life

8.8 (26) 2961 5 Min Comments

My dirty trip to NYC

By Sluttyfemboy 9 May 2025

A horny femboy lives out their sexy fantasies In the big city

6.8 (9) 1430 1 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.

8.5 (9) 1486 12 Min Comments

Sissy for old Men (ch. 2)

By Cherrypie 26 Apr 2025

Our sissy slut has discovered she loves pleasuring nasty Old Men in every way possible..join in our sweet gurls journey

8.5 (14) 2385 16 Min Comments

Wearing panties at the video store

By Alleykat 23 Apr 2025

I can’t forget that time I was wearing panties in the video store the clerk turned me into a sissyboi in just 20 minutes

9.3 (25) 2537 6 Min Comments

Trailer trash cumdump (ch. 2)

By Alleykat 22 Apr 2025

Three months ago I was drugged and made into a cum dump for old perverts at this trailer park i sucked cocks for the first time letting everyone cum on my face my naked body in my belly

8.9 (29) 2608 7 Min Comments

Rest-stop custodian my best job ever (ch. 2)

By Alleykat 21 Apr 2025

After getting a job as a rest stop janitor I broke up with my fiancé now I’m a full time cocksucker

8.0 (28) 1540 5 Min Comments

My full time journey

By Jester4fun 18 Apr 2025

The story of how and why I went full time feminine

9.2 (34) 1844 7 Min Comments

Caught Crossdressing

By BillyBoy 15 Apr 2025

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

5.3 (10) 2552 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.

8.1 (18) 2049 4 Min Comments

Fantasy fulfilled, or nightmare realized

By PnwRobert 28 Mar 2025

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

6.9 (24) 2307 10 Min Comments

Doing It For Daddy

By JessiW 24 Mar 2025

What do you do when you hear strange sounds at night? On a hot, restless night. This one is strictly fantasy.

4.5 (11) 2238 2 Min Comments

Feminization

Sissy Dad's Awakening

By ThePerfectcameltoe 21 Mar 2025

Chapter 1: A Hot Mess. In this chapter, an alpha son named Boland receives a distress call from his omega father, who's struggling to cope with a chaotic situation. Desperate for support, the omega dad reaches out to his son, seeking refuge and a temporary place to stay for a few days, hoping to find solace and stability with Boland.

8.4 (45) 3978 29 Min Comments

Into the looking glass

By Okamaguy 16 Mar 2025

An unplanned visit to an unprepossessing suburban gay bar changes a 19-year-old English femboy’s life.

6.1 (11) 2122 17 Min Comments

Keds Bitch (ch. 15)

By Prettyboy 10 Mar 2025

After having hot sex, Tom and Jackie spend weekends together. In the morning they start with Tom licking the soles of Jackie Keds while Jackie blows him. Later in shower Tom pees on Jackie's pretty ass who loves the taste of Tom's urine when she sucks his dick

9.3 (2) 400 3 Min Comments

A Deal's a Deal

By Sissyboi69 8 Mar 2025

Jack finds out something he did to his girlfriend in the past has finally caught up to him... and now he has to pay the price.

8.8 (81) 7354 10 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

8.2 (29) 3428 4 Min Comments

Meeting a gay sissy for the first time

By BillyBoy 5 Mar 2025

My first encounter with a true gay sissy was very eye opening. She liked it kinky. And being the good friend I am, I did my best to please her.

9.5 (20) 2435 7 Min Comments

Want more porn with crossdressing men?

If the gay sex stories and fiction with transvestites fired up your imagination, and now you want something more, we have everything you could desire. The femboy & crossdresser gay porn videos we provide our users are filled with guys dressing up as gals and having hot gay sex with handsome partners. Should you be interested in what the most popular sites on the web offer, the gay crossdressing porn reviews we write and publish will give you a clear idea of what to expect. The latest productions are the stars of the gay porn blogs that keep you up to date. In case your taste for sissy adventures is not yet satisfied, the gay porn pics are available with sexy entries that will get you going like nothing else can.

About our sissy crossdressing stories

GayDemon Story Library has been online since 1999 and is currently the best source of gay erotic stories you can find. All the gay sex stories with transvestites and sissies in this vast archive are available to read and download for free. Individual authors create and upload the gay erotic stories you will find here in our story archive. Please respect their copyright and do not repost these creations without obtaining permission from the writer first. If you like a particular crossdressing short story or novel, don't forget to rate and leave a comment to express your appreciation.