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 ?
Gay Crossdressing Stories
GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.
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.
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.
New hormone tabs from the web
By Frank Chainges 29 Jun 2025
Need to improve my sissy, I am too masvukine
Jock Princess
By Victor 28 Jun 2025
My son's jock best friend wants to be daddy's side pussy.
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).
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.
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.
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.
Choose Your Fate
By Sissyboi69 11 Jun 2025
Three assaulter's are forced to decide what their punishments should be.
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21 Birthday
By Don 7 Jun 2025
Taking a friend out for his birthday
Abusive Sissification (ch. 4)
By Aditii 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
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.
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
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
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.
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.
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.
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.
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
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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?
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
My dirty trip to NYC
By Sluttyfemboy 9 May 2025
A horny femboy lives out their sexy fantasies In the big city
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.
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
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
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
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
My full time journey
By Jester4fun 18 Apr 2025
The story of how and why I went full time feminine
Caught Crossdressing
By BillyBoy 15 Apr 2025
in her underwear, I'm exposed and turned into his cock slave.
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.
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.