Thai Ladyboy Stories

2,151 results
Orientation
Length
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Infinite Scroll

Ladyboy Loves Up The Midwest

by danielblue on Sep 16, 2017
Transsexuals & Crossdressers

When Jasmine, a Thai ladyboy, moved into a small town in Iowa the locals didn't know what had hit them. She was instantly the talk of the town; initially for being so different and exotic but once she opened her club her reputation spread right across the county and state line. It was only a really small place with just room enough for eight tables. But you...

Addicted to Pream's Cream

by Vodka_Jim on Sep 26, 2017
Transsexuals & Crossdressers

It didn't take long after my divorce to settle into a routine. I had my kids the first, third, and fifth weekend of every month. That left me with a lot of free time on the second and fourth weekend. I wasn't inclined to date much at that point and had no real interest in hooking up through Tinder or other dating apps. So my routine on those Fridays was to g...

Thai Travels Ch. 06

by S_Queen on Jan 4, 2018
Transsexuals & Crossdressers

Welcome back, readers, for the final chapter of my story. If you've been with me since the beginning, you will have accompanied me on a taboo shattering journey, both geographical and sexual. I discovered a flair for public sex, I engaged in group sex and threesomes with lesbians, I fucked gays up the arse and received expert blowjobs from them, I played wit...

Sexy Thai Student Welcomes Teacher

by StarfireMayo on Sep 12, 2017
Fetish

Episode nine of the erotic photo journals of an English Teacher in Thailand. I guess this all began nine months previously while drinking with my buddy Dave in the UK. After a few beers, he had turned to me and said: "Tony, why don't you leave that f... lazy, money grabbing slag wife of yours? Tell me, Joanne fucks you how many times a day?" I looked...

Seduced and Hoodwinked Ch. 02

by walterio on Dec 31, 2017
Transsexuals & Crossdressers

ACCEPTING JASMINE Thursdays were working out wonderfully for Darin as a masseur at the Spa. He would massage the voluptuous Rita first and as always, she would leave him with a boner and ready for sex. Jasmine was his second and only client and they would spend hours together. He massaged her lovely petite body and he loved her tits and ass. She loved the w...

The Reunion Ch. 02: Thai Massage

by Valtikka on Jul 15, 2020
Anal

"Krissy! Long time no see! It's so good to see you. You look great girl!" As soon as I get out of the Uber, Micky comes walking to me with wide open arms and gives me a big hug. "Come let me help you with your bags. You're the first one to arrive so you have first pick on the rooms. The rest of the gang will arrive tomorrow." Instead of the overalls I'm use...

Thai Graduation Photos

by StarfireMayo on Sep 17, 2017
Loving Wives

Part six of the erotic photo journals of an English Teacher in Thailand. * Noi looked up at me with those cute mischievous little eyes of hers. Her mouth encircled my cock tightly while her head bobbed up and down on my dick, helped by my right hand firmly pushing down on her head to ensure she took all my long white cock deep into her throat. She had wok...

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,...

Cockatoo Pt. 20

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

I live for feedback. ***** I glanced back as I left the bar at Tony, who was smirking all over his face and I swore to myself I would wipe that look off his face as soon as I could. I hurried back to the apartment, where Alex was working on some business for the restaurant. I let her listen to the conversation on the tiny recorder I had used to tape everyt...

Inheritance Includes a Houseboy Ch. 04

by walterio on Sep 14, 2017
Novels and Novellas

AUTHOR'S NOTE: This story contains encounters involving gay sex, bi-sex and straight sex which is why it was categorized under Novels and Novellas. ***** BETSY'S WEEKEND Betsy arrived early Saturday morning as she wanted to get started early. She was accustomed to morning sex with me in the office so I wasn't surprised. When she arrived I introduced her...