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
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.
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?
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
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.
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.
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.
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
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.
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.
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He came up behind me
By sandybotm 31 Mar 2025
You never know what can happen when you chop veggies in a skimpy outfit.
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.
Tricked into actually being his bitch
By BillyBoy 11 Mar 2025
He was suppose to untie me but he had other ideas first
Caught in her panties by my mean stepfather
By BillyBoy 6 Mar 2025
George finds me in panties. Then the real trouble really begins
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.
Fuck me in my Mary Janes
By Prettyboy 1 Mar 2025
Jackie, a crossdressing bitch, has a new pair of Mary Janes and is looking for a guy wearing high black boots to fuck her. Jeff is turned on my Jackie wearing Mary Janes so they hook up for a hot fuck.
Dad's Book Store
By BJJL 25 Feb 2025
When his son decides to take over the book store, there are some changes dad didn't count on.
Closeted Crossdresser
By slut4roughuse 15 Feb 2025
Blackmailed crossdresser sissy used by neighbor
The Mastery of Table-Turning (ch. 28)
By Rawley Myers 13 Feb 2025
Can one imagine anything more blood-curdlingly horrendous to contemplate than for a thirty-year-old man having to stand - in nylon stockings, suspenders and high heels, dressed in a tiny pair of frilly lace knickers, clearly on view and openly revealing his rampantly aroused manhood.
The Mastery of Table-Turning (ch. 27)
By Rawley Myers 12 Feb 2025
As I was told to stand up, a woman’s black lace suspender belt was produced and fitted round my waist. Elastic straps with satin ribbons hung down at both the front and back of each thigh with the little rubber button clasp.
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Revenge of the gay master
By BillyBoy 6 Feb 2025
I forgot to watch myself when posting rude remarks online. I was found out, and the Gay Master came to visit. He did everything to me that I'd said was crude and disgusting. This a fantasy piece.
Another Gay sex encounter
By BillyBoy 5 Feb 2025
My gay neighbor seduces me, then keeps me on the hook for his kinky Gay pleasures. What to do now?
Crossdressing Boot Bitch (ch. 2)
By Prettyboy 4 Feb 2025
Jackie likes Only Maker website which features guys in women's boots with high heels. He is wearing a pair of knee high white patent leather laced boots which attracts Jim. Jim enjoys fucking Jackie in his knee high black Docs
Tyler said he was a top
By BillyBoy 29 Jan 2025
Tyler said he was a top, but he didn't sound stern enough. I was wrong!
Hassan My Mom's Arab Boyfriend (ch. 4)
By Catwithapen 26 Jan 2025
With Emma still in Hawaii, Chris began to settle into his role as a submissive to Hassan. See how their usual morning routine goes.
Jamal the Star Athlete (ch. 2)
By Catwithapen 19 Jan 2025
Just when Liam thought things were not possible between him and Jamal. A school announcement gave him a chance at being Jamal's bitch. Starting with a firery sexting.
Hassan My Mom's Arab Boyfriend (ch. 3)
By Catwithapen 18 Jan 2025
Chris is about to be kicked out of his Mom's house, but his mom is going on a trip to Hawaii, leaving him alone with Hassan. Chris had to think of a desperate plan to stay in the house. Watch as Chris finally submits to his desire and becomes a submissive to Hassan.
Jamal the Star Athlete
By Catwithapen 17 Jan 2025
Liam is a college student who had a crush with his college's football star Jamal, a black muscle god who stand at 6 foot 5. Liam couldn't help but imagine the things Jamal could do to him.
Husband decides on drastic action
By Frank Chainges 6 Jan 2025
Husband decides he needs more than most wearing feminine clothes and calls for drastic action.
Late night mystery man
By BeefyFem 5 Jan 2025
A random online encounter between a femboy and man leads to an evening of passion and excitement.
Big Ass student (ch. 3)
By Dondee 3 Jan 2025
Got gangbang by different men in my sexy red fishnets showing my big Fat Ass
Straight friend from the military orchestra uses me (ch. 4)
By Sufficient_Offer 29 Dec 2024
Ivan is desperate to fuck a pussy and might actually cross the line with me this time.
Hassan My Mom's Arab Boyfriend
By Catwithapen 28 Dec 2024
Chris is feeling conflicted as he falls for Hassan, his mom's hunky, arabic, muscular and dominant boyfriend. He can't help but imagine Hassan slapping him, choking him and fucks him like an alpha does to his bitch.
Thank you, Mister Townshend (ch. 6)
By Okamaguy 27 Dec 2024
Paige services one of the workmen. She has a narrow escape from an Uber driver and is rescued by Jerry. She puts on her maid costume to service the workman again, sucks his co-worker, and sets herself up for two night of fun alone at the resort before Mr. Townshend joins her.
Thank you, Mister Townshend (ch. 5)
By Okamaguy 26 Dec 2024
Paige gets a double taste of Africa and enjoys herself at an adult cinema, and Mr. Townshend gives her something to look forward to.