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.

Sherlock Holmes Plays a Prostitute

By Del Crane 25 Dec 2024

Saving the crown jewels and makes the ultimate sacrifice-his ass.

8.7 (12) 946 6 Min Comments

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.

9.8 (5) 579 33 Min Comments

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.

9.1 (6) 655 19 Min Comments

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.

9.1 (8) 971 19 Min Comments

How I became an adult bookstore slave (ch. 2)

By Filthyslagbag 8 Dec 2024

I fully immerse myself into my new role.

8.2 (52) 7626 4 Min Comments

My first time with Terrell (ch. 2)

By pawb bunny 7 Dec 2024

The days following

9.2 (33) 3216 7 Min Comments

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.

9.6 (83) 12260 27 Min Comments

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.

7.0 (27) 5780 3 Min Comments

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.

9.5 (107) 9770 9 Min Comments

Dad likes cheerleaders

By lxfagcumdump 16 Nov 2024

Scott knows his father loves cheerleaders... So he decides to dress like one to please him

8.9 (78) 8052 3 Min Comments

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.

9.3 (82) 8718 9 Min Comments

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!

7.9 (48) 3769 4 Min Comments

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.

9.5 (5) 130 11 Min Comments

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.

9.2 (162) 15107 10 Min Comments

Gaff panty, Cummy shorts, Deep insertion

By BillyBoy 16 Oct 2024

well, the title says it all. a crazy night indeed

7.7 (13) 2043 2 Min Comments

My first time with Terrell

By pawb bunny 14 Oct 2024

White 18 year olds first time having sex and its with a sexy 26 year old black man

9.0 (79) 8613 9 Min Comments

Closet crossdressing goes very wrong, or did it?

By BillyBoy 10 Oct 2024

Dressed in private but I have to answer the door for my neighbor. It turn out to be a very naughty afternoon.

8.2 (35) 7339 6 Min Comments

CD Hotel sex

By Jester4fun 3 Oct 2024

Sissy CD takes dick in hotel

9.3 (132) 12261 8 Min Comments

Spit roasted at home

By BillyBoy 12 Sep 2024

He had me cuffed, wearing a humiliating pink frilly outfit, with a huge nasty purple veined rubber cock in my mouth, and his fat cubby cock fucking my ass from behind. John was kind enough to fulfilled my fantasy for me.

8.6 (30) 5184 4 Min Comments

Cruising

By Danni 5 Sep 2024

Falling in love sucking strangers in public it’s scary dangerous but sooo EXCITING

8.2 (35) 4363 6 Min Comments

Miss Jenny from Ohio (ch. 4)

By Okamaguy 28 Aug 2024

Jenny spends the day as a schoolgirl and gets more cock than she bargained for.

9.6 (9) 3175 16 Min Comments

Miss Jenny from Ohio (ch. 3)

By Okamaguy 27 Aug 2024

Jenny goes from schoolgirl sex to truck stop sex..and loves it all

9.3 (8) 876 33 Min Comments

Miss Jenny from Ohio (ch. 2)

By Okamaguy 26 Aug 2024

Day 2 of Miss Jenny's adventure in rural Japan. She gets all the cock she wanted and a liltle more than she bargained for..and keeps uncle and granddad happy.

9.6 (8) 1209 22 Min Comments

Miss Jenny from Ohio

By Okamaguy 25 Aug 2024

I go to stay with a female friend's male relatives in rural Japan, end up becoming Miss Jenny from Ohio, and get to sample most of the local manhood.

9.6 (26) 2534 12 Min Comments

Bound Gagged and Gay'd Me

By BillyBoy 23 Aug 2024

He answered my ad, answered my fantasies, and answered my question: Was it good for you?

8.8 (21) 5151 8 Min Comments

How I became an adult bookstore slave

By Filthyslagbag 21 Aug 2024

How I became a bookstore sub

8.9 (113) 12066 5 Min Comments

Cruising the Highway

By deansaz 2 Aug 2024

Just on a short drive down the highway when a couple girls began flirting with me from another car on the highway.....

8.3 (26) 2814 3 Min Comments

College and finding the real me

By KellyGirl2010 29 Jul 2024

After graduating high school, I try to figure out who I am and I find that in the arms of another man. Parts of this story are true like my first time panty shopping, going to the adult bookstore, my brother knowing about me wearing panties and the college LGBT Center.

9.1 (30) 4036 23 Min Comments

Call Me a Fuckin Fruit

By Prettyboy 28 Jul 2024

Jackie is wearing a new pair of pink leather shorts with the hopes of attracting a horny top. Jim is a turned on by Jackie's shorts and enjoys her ass both in the gorgeous pink leather and also in the flesh.

8.1 (11) 1259 5 Min Comments

Finally giving in

By ClosetCd 28 Jul 2024

A married husband finally giving in to his desires

9.1 (89) 7320 6 Min Comments

Wearing panties

By KellyGirl2010 25 Jul 2024

Sucking my first cock

8.3 (26) 8576 7 Min Comments

BDSM lovers

By BillyBoy 24 Jul 2024

I wander into a sex shop for gay BDSM lovers. I'm in the wrong place!

8.9 (44) 3793 6 Min Comments

Just to Dream a Dream

By luvaslip 20 Jul 2024

Terry arrives at her uncle's house early and lays down for a nap. She dreams a dream that becomes real and gets a lot of loving.

8.9 (13) 1363 2 Min Comments

Twins bothers have lot more in common (ch. 3)

By Xoxo 19 Jul 2024

Harry gave his BBC friends a little show

8.9 (10) 2577 7 Min Comments

Can I go back to my favourite club? (ch. 2)

By Frankfurt Chronicler 17 Jul 2024

Our narrator's adventure at his favourite club continues with an unexpected sexual encounter while the band plays.

9.6 (17) 1986 13 Min Comments