First Time Sex with a Ladyboy
An unintended adventure that set the stage for a life of openness and experimentation. An absolutely horror-filled moment, that was eventually accepted and indulged!
First Time Sex Series – First Edition
Jeremy opens up about the biggest mistake of his life. Jeremy meets the woman of his dreams one night while out with a friend in downtown Patong Beach just off Soi Bangla, the main nightlife strip.
Things go horribly wrong… or right, depending on your perspective on things.
Read the sample below.
First Time Sex with a Ladyboy (Free Sample from the book)
Before I went to Thailand for the first time I tried for weeks to find other guys or women already there to write me back, so I could get a better feel for the place. I’d lived in the USA all my life, and though I’d ventured out to other countries like Canada and Mexico, I’d never lived anywhere but the states. It’s a scary proposition just picking up and leaving to move to another country. I was definitely ready to go – but I had a lot of questions.
That’s where this mysterious guy named Mick comes into the picture. I had posted on a Thailand forum that I was thinking about moving over to Thailand and that I was a photographer in New York City in a past life. I thought maybe I’d do some adult photo and video shoots of girls in Thailand. There were some good websites covering that topic and I’d seen a hell of a lot of them. I’d come to love Thai girls and in truth, this was the major reason I chose Thailand over somewhere like India, China, or Japan. I just loved Thai girls.
I’d known some Thai girls in the USA – and ‘had’ some as well. They were usually great in bed, and eager to please. They had few hang-ups like American girls do – and I really enjoyed my time in bed with them when I was lucky enough to find a willing partner. I dreamed of a day when I could choose from among hundreds or thousands of fuck-partners.
Don’t we all!?
I thought it was possible in Thailand. I just needed to make the move and go for it.
So, this guy Mick wrote me back in response to my post on the forum.
He was from the states originally, in Las Vegas, Nevada. He was very secretive about what he was doing in Thailand. That led me to believe he was shooting porn. That was perfect. At least I thought I had a good read on this guy – but, he gave away so little information that I wasn’t sure. I was hoping he wasn’t trafficking drugs, but I was pretty sure he wouldn’t be on the internet at all in that case.
He did go way out of his way to answer questions I had about moving to Thailand – and, since he’d been there for more than three years already and was also from the USA – I trusted that he knew what he was talking about. As it turns out, I was right – the guy was a godsend, and he helped me feel good about selling all my shit in Miami and booking my ticket to Bangkok.
After I spent a few days in Bangkok (see this short story for my first night in Thailand – First Time Sex with an Asian Prostitute – Volume 1) I went down to Phuket Island where Mick stayed.
As it turns out Mick was shooting adult content for some of his own websites as well as other membership websites. Mick shot about 90% ladyboy (shemale) content. I was as surprised as you would be. I’d seen some ladyboys on the Thai sites – you couldn’t avoid them. I was never into guys in any way, so I looked at their tits with interest, and it was fascinating that some of them were able to make themselves up to look convincingly like real girls… but, there just wasn’t any big boner in my pants over them.
If Mick was into them, that was cool, I don’t judge anyone for what their personal perversions are – if you read some of my stories you’ll see that I have enough of my own.
So, Mick was a ladyboy nut. I’m sure he preferred them to women. Apparently, he got hooked on them once he moved to Thailand. He was already a photographer in the states, shooting pregnant, bondage, and hypnosis porn primarily.
Here in Thailand he built up a few ladyboy websites. For those who haven’t heard the term ladyboy – it means the same as shemale. Ladyboys are Thai guys with dicks (to start anyway) that dress as women, get boob implants, have their dicks changed to a vagina, and take hormone pills so they can squirt milk from their nipples and grow a shapely female body.
As I said, I wasn’t interested in the least, but I had seen some ladyboys on websites that were no different from real girls. I wondered if in person I could tell a difference.
Once in Thailand most of the gals that Mick introduced me to, I could tell almost right away if they were ladyboys or true girls. But, there were about five or so out of the usual group of a hundred that we saw nightly that I couldn’t be quite sure of. They were like passable women. I just could not tell they were guys.
It was Impossible to tell, no matter how hard I tried.
On this night, Mick insisted we go out. I was staying in a room in his house, so we went out a lot.
We had worked hard for a couple of days and were due some fun. For me that meant finding a hot girl with no inhibitions – usually for anal sex primarily, and whatever else happened was just a bonus. I loved anal sex and you might say I was a sort of anal addict at this disturbing time of my life!
We hit some of our regular bars – girl bars and ladyboy bars, and we were having an exceptional night. We landed at Tequila Club on Soi Crocodile, also known as Soi Ladyboy, or Soi Katoey (katoey is ladyboy in Thai). We were given the two best seats at the bar by the owner who was a good friend of Mick. The ladyboys were everywhere that night. It was probably a weekend night but honestly, I don’t remember which day it was. They all ran together when you didn’t work a nine-to-five job. Mick enjoyed a cult-leader-like status among the ladyboys in Patong Beach.
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