Literotica Wifes First Time With A Big Cock Ladyboy Stories

372,017 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Ladyboy DP for Thai Wife

by StarfireMayo on Sep 19, 2017
Transsexuals & Crossdressers

Part five of the erotic photo journals of an English Teacher in Thailand. * Dear Reader: Some people are not comfortable with their own sexuality and they object to cuckold and bi-sexual stories. That is okay - To those people I would suggest not to read this story or to leave your negative comments. * I opened my eyes and lay still in bed, awake unusu...

Anal Anywhere, Anytime Ch. 02

by walterio on Jan 22, 2020
Anal

BEFORE CHARLOTTE As long as Walt could remember he had been drawn to a shapely female bottom. I didn't have sex until I was 18 but I had hundreds of boners from just looking at the outline of curvy buttocks contained in skirts and slacks. I found myself watching TV hoping to get a look at an actress's derriere. Even during commercials, I checked out a curvy...

Seduced and Hoodwinked

by walterio on Dec 27, 2017
Transsexuals & Crossdressers

INTRODUCTION Darin Thomas loved his job as a masseuse working at an upscale spa in California. He loved massaging the bodies of wealthy and horny women. There were some who just had a massage and others who wanted sex following the massage. Each massage room was private and the door could be locked to insure privacy and no interruptions. He was still stud...

Ladyboy for my Thai Wife

by StarfireMayo on Sep 19, 2017
Transsexuals & Crossdressers

Dear Reader: Some people are not comfortable with their own sexuality and they object to cuckold stories and wife sharing. That is okay - To those people I would suggest not to read this story or to leave negative comments. To all the many others, and especially my thousands of readers and fans please read on- and enjoy. If you like this story, do not forget...

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...

One Night in Bangkok

by trouser on Oct 25, 2015
Transsexual

You were extremely nervous. Not only was it your first time to Bangkok, or Asia in general, but you had also arranged to turn one of your most secret fantasies into reality: One night with a thai ladyboy. And since your company had sent you for an important meeting to Bangkok the chance was finally there. You had already hooked up with some potential ladyboy...

Open in Reader

Ladyboy Maid

by HarlanPilate on Sep 25, 2017
Transsexuals & Crossdressers

'Hi,' she said, her voice sultry. 'I'm the new maid. Lisa.' The new maid had turned up at the house of Mark and Susan Reynolds. Mark had answered the door, and he was impressed. Lisa was around thirty, with large brown eyes and wide red ruby lips. Her exotic features made Mark think that she was from somewhere near Persia. She was about 5'6" in black high-...

My Cleaner Ch. 03

by gendidi on Sep 15, 2017
Transsexuals & Crossdressers

My father had a second stroke recently. The moment I got the news, I was asked to fly back immediately by my mom. I can fully understand, a man in his 80's...My wife was getting frail and could hardly walk. So, I decided to hire someone to look after her and I went back alone. I bought the next available flight flying East. After 13 hours' flight I finally...

Alone In Pattaya

by gendidi on Mar 9, 2020
Transgender & Crossdressers

That must be almost 10 yeas now. I was in my late 30s and married back then. I was working for an international company as Regional Director. Every few months, I had to fly to Asia for business meetings. One year, I went to Southeast Asia for a business trip but unfortunately the meeting in Bangkok was cancelled at the very last minute. so I had a few days...

Banker's First Encounter

by gendidi on Sep 13, 2017
Transsexuals & Crossdressers

The story below was based on my personal experience... During the economy downturn in the 90's. I was in my later 20s. My job then was a banker. Banks stopped lending money and all those bankers who managed to keep their jobs were told to sell fixed deposits instead to keep the bank healthy. Being a sales guy. I went out all day trying to meet customers to...