Story First Experience With A Ladyboy Stories

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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...

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....

A Ladyboy

by Owmyballs on Apr 29, 2025

Hello. My name is Chantara Noi. I am a twenty- two year old ladyboy from Bangkok Thailand who recently emigrated to the United States. Today I live in Columbus Ohio. I have shoulder length black hair and gorgeous brown eyes. I'm five foot two and petite with average sized breasts. Please don't ask if my tits are real. I'm a ladyboy...of course they're fake d...

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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...

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...

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...

My Thai Ladyboy

by TheSevenSeas on Apr 27, 2020
Transgender & Crossdressers

There is a saying that 'when one door closes, another opens.' That was certainly true for me. My relationship with Jen (see my previous story: My First Ladyboy) continued for some time, but we rarely managed to see each other. I was mostly working in Africa and just couldn't get over to the Philippines very often. Eventually we drifted apart. Yet I was truly...

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...

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...

Briefly Encountered

by wylite on Sep 16, 2017
Transsexuals & Crossdressers

I had business in the Middle East and this required frequent trips between the UK and various middle Eastern capitals. The routing of my flights was my choice and I often used to transit via Amsterdam; I would ensure that there was a good long transit time between my flights and this allowed me to make leisurely visits to Amsterdam's city centre. It's a shor...