Ladyboy Fuck Guy Stories

265,399 results
Orientation
Length
Source
Infinite Scroll

First Suck

by mercury7259 on Dec 10, 2019
Transgender & Crossdressers

Donna I'm sitting here looking out the window, seeing, but not really looking. My mind is racing, not being able to single in on any one particular thought. I see puffy cotton ball clouds and a radiant blue sea as the voice comes on and says "We'll be landing in Manila in 30 minutes. The current temperature is 86 degrees and clear. We hope you have enjoyed...

A Ladyboy for Master Hans

by justincbenedict on Sep 16, 2017
Fetish

After Chip had cooked dinner and waited on Hans, and had his own meal in the kitchen, cleaning up quickly, he got busy polishing Hans's shoes and boots. But in the middle of polishing Master Hans's last set of boots, Hans interrupted Chip. "Chip. How many times I must tell you? You have not written down your Stuhlgang, your poo-poo!." Hans, who was a st...

Blind Date

by VeniVici on Sep 16, 2017
Group Sex

"Hello, I'm supposed to be meeting a Mr. James here." The receptionist looked up from her desk and glared at Zil, seriously not smiling. "I believe you'll find him in his suite, on the first floor. The River Suite." She snapped, returning to her bookwork without giving so much as a second glance or a welcoming smile. Zil walked slowly, almost hesitantly...

Suspected Affair

by 69Jance on Apr 21, 2020
Transgender & Crossdressers

I had suspected for a while but recently found confirmation, not that I would blame her. I know we loved each other but I also knew there were needs the other could not fill. I found evidence she was having that need I could not meet, met by someone else. I was a bit jealous but in a strange way. There was no anger but a bit of arousal as I imagined her love...

Miss Chianti's Troy-Boy

by justincbenedict on Feb 26, 2019
BDSM

Chianti finished brushing her hair and gave it a cursory look, and the doorbell rang. Chianti put her brush down, and pulled the scoop neck of her pretty pink sundress down a little, just so the jugs poked out a bit more. The bell rang again. "I'm coming!" What a beautiful dress, sleeveless and so short. Purchased by Ingersoll, a sad little man who needed...

Lucy in the Sky

by DirtyyDom on Jan 16, 2019
Erotic Couplings

It was half past midnight at Club Sky; sweat was beginning to overpower the smell of cheap cologne and booze. On the dance floor what looked liked a large school of confused sardines, wriggled around to a rhythm. "It's your round, bro." Patrick asserted. "I've got two bids over there eyeing me in the corner. They're looking a little thirsty—parched, if you...

Marion's Turn Ch. 01

by jomar on Sep 13, 2017
Fetish

I stood in the foyer. She was gorgeous. Hair up, dressed in black; corset, stockings, panties, high heels. And a strap-on. "You really gave it to me good last month, baby. I didn't expect those other guys. At first I was a teensy bit mad...but I gave into it and I couldn't get enough cock, could I, baby. Mmm, those cocks in all my holes, all slippery with...

Juliette Gets a New Dress

by Dreamstime on Sep 16, 2017
Transsexuals & Crossdressers

It builds up like a huge wave of excitement, lust and fear. My want for a dirty, no holds barred session with my wife. She knows it's building up in me, the grumpy comments, the early morning hard-on's that prod her in the back. Nice, romantic love making has its time and place, but the sexual animal in me is beginning to stir. "I want to be your sex...

Letter from Gander Cove

by justincbenedict on Nov 20, 2018
BDSM

Dear Shoeblossom, My teachers always said to me, "Norbert, you'll never amount to much, smoking weed and playing video games..." but I found I had hidden talents... Recently I joined a sadomasochistic group. It's a local thing. Amazingly, I met the hottest girl who wanted me to punish her! Victorine is a very attractive woman who's got about twelve or thi...

Housemate Deception

by EnojadoConsado on Sep 16, 2017
Transsexuals & Crossdressers

I watched my Amelia, my new flatmate walk to the kitchen. I took a moment from my videogames to watch her walk past. She was only wearing a shirt and panties. It hadn't taken her long to get comfortable around me, her having only been here for a month. She reminded me of myself a few years ago. I was only three years older, but I noticed despite being a girl...