Ladyboy Stories

248 results
Infinite Scroll

Promiscuous Parents and Sons

by walterio on Sep 14, 2017
Novels and Novellas

PRELUDE While Pete, Kurt's dad was spending the day with Sandy's mother Lisa, the two twenty somethings were involved with passionate sex. Sandy was sitting on Kurt's body with a thick cock buried in his ass. As Sandy rode his muscular neighbor, Kurt reached up with both hands and fondled the effeminate blonde's cute titties and tweaked the sensitive nipple...

Learning About Kathoeys

by walterio on Dec 2, 2019
Transgender & Crossdressers

PRELUDE Andy Morris was waking up slowly and as he stirred, he felt the presence of another body in bed. He rolled to his side and saw the lovely Jasmine who had stayed the night. She was on her side facing away from him and he took in her naked beauty. He recalled the night before and the marvelous sex they had together. As he looked at her incredible ass,...

Maid to Measure

by Poontanga on Sep 15, 2017

We'd hired Pina, the new Philipina maid a few weeks ago, my wife was away on a business trip in Thailand, and my twin adopted daughters Arkana and Arianne had been ribbing me that she'd be fired as soon as mum got back, given she was such an exotic goddess. Trouble is, the more my daughters ribbed me, the more my thoughts turned carnal. We'd adopted Ari an...

Recruited Ch. 01

by Rstyusameg on Sep 2, 2017
Transsexuals & Crossdressers

All characters are fictional, except me, everyone in the story is over 21. My stories will involve, male/male sex, cross-dressing, and bad language, so if this offends you please don't bother reading. I stare at myself in the bathroom mirror, carefully applying finishing touches to my pink lipstick, I'm ready. I walk downstairs to fix myself a drink, exu...

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...

Anal Anywhere, Anytime Ch. 01

by walterio on Jan 22, 2020

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...


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...

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...