Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

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...

My Cleaner Ch. 02

by gendidi on Sep 15, 2017
Transsexuals & Crossdressers

I only went back to my home country once a year. This year, I went back alone because my wife wasn't physically fit to travel. I had to leave her back in UK because my parents were in their late 70s. I needed to spend as much time with them as possible. When I arrived in Kuala Lumpur, it was late afternoon. I didn't sleep well at all on the flight and I wa...

A Perfect Life

by FarangPrince on Sep 13, 2017
Transsexuals & Crossdressers

As I write this, I am sitting at my laptop computer on the balcony of my apartment in Bangkok, Thailand. Behind me my ladyboy lover is puttering around in the kitchen, washing the dishes from our breakfast. My lover is a beautiful Thai ladyboy. She has gorgeous features – lovely almond-shaped dark eyes, upturned sexy lips, dark smooth skin, thick black hair...

Catia Becomes a Ladyboy Escort

by TimT1972 on Sep 14, 2017
Transsexuals & Crossdressers

The days when poverty stricken parents sold their children into slavery are a distant memory. They are stories from the nineteenth century not the twenty-first. This said, parents are quite entitled to earn a 'finder's fee' if they introduce prospective staff to an employer. Times were hard in Rio de Janeiro and Mateus' father wanted the best for his son....

Nephew Chris becomes Niece Chrissie

by walterio on Sep 19, 2017
Transsexuals & Crossdressers

PRELUDE "Okay Sara just slow down and tell me again what happened," Jake instructed his older sister over the telephone. "It's our son Chris. Henry and I came home early and found him having sex in the family room," Sara blurted out. "Okay I understand that. Chris is 18 years old so other than doing in your house it was consensual. Why are you so upset?"...

The Lab Rat Pt. 04

by TheMarlboroMan on May 13, 2020
Transgender & Crossdressers

The Lab Rat Part 4 Karla Wasley, Leah Guzman, Robin Venters, and Anna Edwards were standing there in an observation room watching me in my total nakedness via the eight-foot wall screen thanks to hidden cameras in the examination room as I came all over the ladyboy's face after he could no longer swallow what I was spurting fast enough. What struck them as...

Craigslist Bottom Bitch

by xploring96 on Mar 21, 2018
Transsexuals & Crossdressers

The following story includes transgender characters, Domination/submission, and denigrating terms used to humiliate. If this offends you please do not read any further. This is the second chapter in this series and picks up immediately after the first chapter. I recommend that you read Craigslist Cumslut first. In case you decide not to here is a summary....

NOT Waiting For Godot XXX

by eneo on Sep 1, 2017
Humor & Satire

Characters: Noi Toi Moi, the ladyboy actress who plays Noi Me, the writer, director and DP (director of photography you dirty-minded people!) Yes, I appear in all of my movies, usually as the lead actor, a balding Jewish nebbish who gets the best and prettiest asian ladyboys. and featuring Ron Jeremy, as Marlan Bondo Opening Scene: [Dialogue between T...

Busted and Hoodwinked

by walterio on Sep 16, 2017
Transsexuals & Crossdressers

INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack actually liked fucking Barry and having Barry suck his cock. Ma...

The Club

by SweeetLee on Sep 13, 2017
Transsexuals & Crossdressers

They entered the club and were greeted warmly by a long-time acquaintance. She was a dark haired beauty, and the one who had first told them about this place and used her membership to get them in. It wasn't that it was exclusive. It was off-limits to outsiders. You had to know someone just to learn the address. She ushered them through the very legitimate...