Ladyboy Fuck Guy Stories

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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....

Makati Ch. 05

by massageaddict on Jul 15, 2020
Novels and Novellas

I sat at my favorite table smoking when Lilly showed up to ask if I needed anything. I asked for a bottle of Perrier and she smiled and said "Right away Mr. Bob." I sent off a few emails, sent some pictures of the new place to my wife and then scrolled through my WeChat deleting all the whores wanting to connect then checked my Whatspp. I had a message from...

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...

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...

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...

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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 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...

Flavia's Secret

by TimT1972 on Sep 16, 2017
Transsexuals & Crossdressers

Filipe had always yearned to wear satin knickers. He loved the idea of wearing tight, little briefs made of sensuous silky material. He simply could not see why boys should not be able to wear silks or satins instead of plain cotton. But at home he had no opportunity to satisfy his desires. His mother would be sure to find any illicit underwear and then ther...

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...