Ladyboy Massage Stories

55,680 results
Orientation
Length
Source
Infinite Scroll

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...

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...

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...

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...

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...

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-...

Encounter of the First Kind

by gendidi on Sep 16, 2017
Transsexuals & Crossdressers

I'm a married man in my mid forties. I have an older disabled wife. We don't have any children. We have been married for a decade. Ever since she was disabled, we stopped having sex. She gets depressed occasionally and has been taking happy pills for years. Maybe that's why she lost her sex drive and I don't blame her. We never discussed about sex. I assum...

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...

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....

My First Ladyboy Experience

by Junglist187 on May 11, 2020
Transgender & Crossdressers

I'm a typical man, big hairy and rough on the edges. For as long as I have had internet access I've always been drawn to watching shemale/ladyboy porn, just the sight of such magnificent female bodies always ignited a flame in my crotch area, I had masturbated to these clips thousands of times and I still do to this day. That was as far as that went. I r...