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.
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.
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.
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!
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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.
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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.
Sherlock Holmes Plays a Prostitute
By Del Crane 25 Dec 2024
Saving the crown jewels and makes the ultimate sacrifice-his ass.
Thank you, Mister Townshend (ch. 4)
By Okamaguy 25 Dec 2024
Paige is disciplined by a sadistic German and services a couple of drivers at a truck stop before getting worked over by Jerry, and Paige's mum dresses as a schoolgirl for the boys while Paige and Mister Townshend watch.
Thank you, Mister Townshend (ch. 3)
By Okamaguy 24 Dec 2024
Paige's friend Alan brings a Japanese guy to the house. Mr. Townshend makes sure he fucks her. The young man brings two of his Japanese friends over, Paige changes into her schoolgirl uniform, and three three of them take turns with her. They have another session with Paige as a slut, and Paige and Mr. Townshend make plans for Paige's mother.
Thank you, Mister Townshend (ch. 2)
By Okamaguy 23 Dec 2024
Richard goes to live with Mr. Townshend and becomes Paige, and 18yo sissy girl who loves being fucked by whoever Mr.Townshend decides is right for her.
How I became an adult bookstore slave (ch. 2)
By Filthyslagbag 8 Dec 2024
I fully immerse myself into my new role.
My first time with Terrell (ch. 2)
By pawb bunny 7 Dec 2024
The days following
Control and Corruption
By isaline_cd 20 Nov 2024
A dominant daddy meets up in public with a straight married man. Daddy decides to mark the wannabe sissy as his submissive slut.
My Halloween crossdressing story
By BillyBoy 19 Nov 2024
I knew I shouldn't, but I dressed in women's clothes again this Halloween. It turned out much different from last year, but the final results were the same. A cock in my mouth and another one in my, you know where.
Tom, the married security guard took me for a woman (ch. 3)
By Sufficient_Offer 17 Nov 2024
Sam is about to know why Tom's wife really can't take his monster of a cock aymore.
Tom, the married security guard took me for a woman (ch. 2)
By Sufficient_Offer 11 Nov 2024
Sam is desperate to be stretched again by Tom's monster cock. This time, they have more time to go further.
Caught in hers
By BillyBoy 6 Nov 2024
The gay man catches me in her panties and makes me his bondage fuck toy. I wasn't sure i was going to be ok with it, but, of course, now I love it!
The Ends of Rossford (ch. 10)
By Chris Lewis Gibson 18 Oct 2024
The turmoil of Dan's visit is nothing in comparison to what Fenn and his friends are about the learn.
Tom, the married security guard took me for a woman
By Sufficient_Offer 18 Oct 2024
I tell you this dude was something of a Gladiator movie. Huge guy, way past 6 feet, grumpy look, 38 years old or so, broad shoulders and visible bulge in his kaki workpants, beautifull face with a red cap.
Gaff panty, Cummy shorts, Deep insertion
By BillyBoy 16 Oct 2024
well, the title says it all. a crazy night indeed