Whenever I tell somebody that I lived in Thailand for a year, the response is always the same:

Did you fuck any ladyboys out there?

I usually smile, swat at the air, give a “Pssh!” like that could NEVER happen to me… and then go into the bathroom, turn the sink on, and let my tears pour endlessly into the basin.

Throughout my time in Thailand, I had lots of close calls; and then, there was my date with Matty.

“Matty” worked at my favorite club in all of Thailand: “The Club”.  Which, let’s be honest, is the greatest name for a club you could ever give.

“Where you at?”

“The Club.”

Matty was a promoter for The Club.  I would usually bump into her on the street out front.  The Club was located along the notorious “Khaosan road” strip of Bangkok, one long street which could be walked start to finish in about fifteen minutes.  On Khaosan, you would always run into a colorful cast of characters: drunken backpackers, Thai’s selling paraphernalia and offering massages, people eating fried insects, and of course, kathoey, the aforementioned men who at some point of their life, decided to become women through means of dress, or surgical operation.  In other words, “ladyboys”.

I used to see Matty outside The Club and offer a salutation before going in.  She had a great figure.  She was taller than most Thai girls, and had a gigantic pair of knockers.

I had been going to The Club for many months before I decided, “Hey, I should ask this chick out.”

The date was super informal.  Unlike other places in the world, in Thailand, you can get by with just chowing down on some street food in these little plastic chairs on the side of the road.  Everyone is cool with it.  If a chick wasn’t, she would be deemed high-so, the Thai word for “high society”, or basically a snobby bitch-face.

I made my intentions clear from the beginning.  This date wasn’t about the conversation, nor the food.

Each time I would make an advance, or lean in for a kiss, she would give me this stunned look and say, “Oh really, you okay with that?  Even though I ladyboy?”  And then she would cackle maniacally.

I started thinking, “This chick has a sick sense of humor.”  Although her English didn’t surpass that of the atypical spunky Thai girl, she could communicate well enough, albeit in a highly broken accent.  Her vocabulary was limited.  Yet, it was unusually advanced in the area of medical terminology.

When she caught me staring at her tits, she uttered.  “Oh, you like?  I have very good doctor.  He give me best breast surgery in Bangkok!”

I frowned.  She immediately burst out laughing, and once again, and I assumed this to be a joke.  But now I was a little suspicious.  When she got up to use the toilet, I whipped out my phone and called the expert.

“Alex.  Alex!  I need your help.”

My Swedish partner-in-crime (the same guy I tripped on acid with on my first day in Colombia in Epic Epochs) was an expert, by virtue of having sex with three ladyboys.  Oral sex on two occasions, anal  the other.  The guy pulled chicks, so I couldn’t criticize.  He always maintained that ladyboys were like women but hotter, and if you ignored the dick it was nothing to freak about.

“I’m with Matty.  Remember her?  From The Club.”

“Oh yeah?  The one with the big tits?  How is it going?  Did you fuck her?”

“No, listen,” I said, checking the doorway to the bathroom, my phone time limited.  “Do you think there is any chance she is a ladyboy?  I’m getting some signs here…”

“Her?  Naaah.  I mean, I’ve always been really fucked up when I’ve seen her, but I wouldn’t worry about it,” he reassured me.  “But I think you should still–“

I hung up the phone as Matty stepped out of the bathroom and walked toward me.

“Everything ok na kha?” she asked.

I nodded, slammed my drink, and ordered another.

---

A couple of hours later, we were back at my house.  I was horny, and we were in my bed.

Clothes came off.  First mine, then we started with hers.  I had no idea what to expect once I took her pants off, but I just prayed it would be anything other than a cock.

I unbuttoned her pants, and slowly, ever so cautiously slid them off.

And I saw…

Underneath her panties…

The outline…

Of a vagina.

HALLE-FUCKING-LUJIAH

When I went to take her panties off, she howled like a werewolf in what seemed to be her auto-defense mechanism.  She forbade me from going any further, and feeling dejected and being absolutely trashed, I laid back and closed my eyes.

It felt like just a brief moment to me, but truth be told, I’m not sure how much time passed.  And then I awoke to Matty tugging at my leg: “I can’t sleep!”  she whined.

That was what I had been waiting for.  Anytime a female gives you that line, there is only one, infallible medicine you can provide: penis.  Doctor Darby delivered that medicine.  And!  To my relief, her vagina was wet!  Fake ones can’t do that.

And so we fucked, I came on her while she screamed, and it was time for bed.

The next morning, after I had kicked her out, I reflected on the experience over breakfast.  I was pleased.  I had done it.  Another Thai sexploit in the bag.  Although there were some scares, I was sure that “she” couldn’t have been a “he”.

I knew the warning signs.  I had just written an article on how to avoid ladyboy’s for a backpacking magazine.  I started thinking about that article, and how I should have included one more thing.  Something a French guy had just told me about surgically-altered ladyboys.

He claimed that since artificial vaginas can’t get wet naturally,  sometimes ladyboys will go into the bathroom with their little pursey, pre-sex, and lube up.

Sitting there, letting that dude’s advice ruminate in my head, I knew that I was safe, since Matty never went into my…

Oh my God.

I was absolutely hammered last night.  Did I pass out last night?  When I closed my eyes, how long was I out for?  Seconds?  Minutes??  If I passed out, she could have easily slithered into the bathroom and lubricated herself!  She didn’t even want sex until after I had opened my eyes… and then she was all for it!  OHMYGODOHMYGODOHMYGOD

And then it hit me:

Her NAME.

Her familiarity with surgical terms.

Her ladyboy jokes.

Her place of employment.

I don’t know if I had sex with a ladyboy.  I don’t think I’ll ever know.  In fact, I would probably say there is about a 60% chance that Matty was a “Matt”.  But what’s there is pretty incriminating.  I may have put my penis inside a fake vagina.  Which doesn’t change anything now.  But heed my kind advice stranger:  If you ever go to Thailand…

DON’T FUCK ANYTHING.