Ladyboy Massage Stories

55,680 results
Orientation
Length
Source
Infinite Scroll

The unexpected housekeeper

by manhasso on Mar 30, 2020
Transgender & Crossdressers

After experiencing difficulties in his personal life, a lawyer discovers the benefits of having a live-in housemaid. 1.Prelude After almost 20 years of legal profession, I was now an accomplished lawyer: I had my own firm, several younger lawyers working for me, big and important clients, a sports car, and a house on the hills overlooking the city. But...

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...

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...

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?"...

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...

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...

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

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....

Seduced and Hoodwinked Ch. 04

by walterio on Jan 7, 2018
Transsexuals & Crossdressers

SHOPPING, MASSAGES AND SEX On Tuesday morning Darin and the ladyboys passed on sex and after breakfast they went shopping. They picked up supplies first and then went to a boutique and picked up some new clothes and accessories. They stopped for lunch afterward and at the restaurant many eyes were on the three beauties. Darin was sure that people were wonde...

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...