Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

My Treasure

by Tetris07828 on Sep 19, 2017
Transsexuals & Crossdressers

I drive truck. Have all my life, ever since I was a kid. My dad took me to my driver's test in a jacked up Ford 150 pickup and had to explain to the examiner that this is what I practiced with. Since then I got my CDL license and have been driving the big rigs. Got to admit, I love the life. You have to love it or you're going to be one miserable bastard. Th...

Meat

by xploring96 on Sep 15, 2017
Transsexuals & Crossdressers

The following story includes a transgender character, Domination/submission and derogatory terms used to humiliate. If this offends you please do not read any further. * James was supposed to meet a friend for a late dinner at "Meat," the best steak restaurant in town. Then just as James arrived, he received a text informing him something had come up, and...

Anal Anywhere, Anytime Ch. 01

by walterio on Jan 22, 2020
Anal

PRELUDE It was the first time that Charlotte had ever come to my place. We had fantastic anal sex on Friday night and we were up for more on Saturday morning. It was a rainy summer day and we were in no rush to get out of bed. She had ridden my cock until she orgasmed and now it was time for me to take that scrumptious ass again. I caressed her ass and tea...

A Pornographer's Apocalypse

by eneo on Sep 1, 2017
Humor & Satire

[Inspired by and dedicated to a very lovely Swedish woman The screenplay was submitted separately] Director's Diary 12.1.2011: We're waiting for Moi and Soi to get here, they're the asian ladyboys we've booked to play Toi and Noi. From their pictures they seem super hot and I think we'll get a boxcover that people will love. I picture Soi sucking off Moi...

Cockatoo Pt. 17

by nikkiesilk on Sep 19, 2017
Transsexuals & Crossdressers

Previously in Cockatoo James, recently divorced, travels to Bangkok on business for a fresh start. He meets Alex, a friend from their university days, whom he discovers is now transgender. Alex and her partner, Areeya, a Thai girl, run a successful restaurant and ladyboy bar on Koh Samui, an island off the coast of Thailand. James falls in love with Alex an...

Makati Ch. 09

by massageaddict on Jul 15, 2020
Novels and Novellas

Chapter 9 At 7:45 I rode the elevator down to see that Sam had the car ready and was waiting for me. I motioned that I would be getting in the front seat and told her to go to the Hotel where we would be picking up Jack and Yomi. I looked down at Sam's long legs encased in her stockings and felt a stirring of my dick. Damn, I needed to get laid tonight. We...

Anywhere Anytime

by xploring96 on Oct 14, 2017
Transsexuals & Crossdressers

The following story includes a transgender character, Domination/submission and derogatory terms used to humiliate. If this offends you please do not read any further. Feedback is appreciated. ***** DAY 1 Kyle slowly wakes up thinking he must have fallen asleep in the outdoors. He feels butterfly wings brushing against his ear and a tree limb against...

Home Again

by PeggyBuxton on Mar 6, 2018
Fetish

The senior year at the university was over at last. Tom had already broken up with Carrie. She was his mother's age and married. It wouldn't have lasted no matter how good the sex was. There had been two others before her, both similar ages, both married. He was handsome and could have had his pick of beautiful coeds. They never seemed to offer the same exci...

28-year-old Bisexual Stepfather Ch. 18

by walterio on Apr 16, 2018
Novels and Novellas

AUTHOR'S NOTE: Reader feedback was to continue with this series. Thank you! Reminder: This series contains straight sex, bisexual sex, gay sex and incest. ***** DAY TWO OF THE CRUISE That morning Dustin was up early and decided to get a quick workout in before breakfast. He went to the fitness center whish was virtually empty. There were only a few other...

Business to Improve Sex Lives Ch. 08

by walterio on Dec 24, 2019
Novels and Novellas

ANAL TRAINING Trace and Brittany were eating a light practice after their customary morning sex. Trace asked, "Who do we have scheduled today?" "A young woman named Justine. She is interested in anal training." "Really, an anal virgin?" "Yes, she has a boyfriend who she dearly loves. He has tried to get to her ass several times but she refused. Now she...