It seems that everybody knows somebody who has accidentally made out with a ladyboy, or worse. I never thought I’d be one of them, but then again, nobody ever does.
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First off, let’s establish what a ladyboy is.
A ladyboy is a transgendered or transvestite individual in Southeast Asia. In Thailand, for example, they are openly tolerated if not embraced and even regarded as good luck charms.
My story takes place between Christmas and New Year’s last year, on Phuket. I would normally avoid what has become such a seedy place like the plague, but it so happened that I had to head there to get a chest x-ray for my Australian visa. While there, I met a group of friends who wanted to check out the ladyboy cabaret. Given that I had nothing better to do, I tagged along.
Ladyboy shows are often a way for ladyboys to save up for the final step of the surgical procedure to become a woman. The performers tend to at least have breast implants, and are quite often absolutely beautiful, and convincing!
I sat through an hour or so of performances in Russian, English, Chinese, and, of course, Gangnam Style, so that every possible member of the audience would be satisfied hearing a song in his/her native language, performed by crystal-adorned ladyboys dancing a little out of sync with smiles plastered on their faces.
After the show, we had an opportunity to take photos with the various performers. One of the more beautiful ones I had noticed on stage beckoned me over.
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I couldn’t say no, right?
He (she?) grabbed my hand and slung it over her (his?) shoulder. My friend, Dylan (who attended with me on the pretense that ‘the journalist in him said yes’), snapped a photo just as the unthinkable happened:
The ladyboy stuck my hand down her (his?) top.
It rested there for a few seconds (though it felt like hours) before I realized what was happening. I pulled it back out at lightning speed, completely flabbergasted, as the ladyboy laughed at me.


For the remainder of the night I just kept looking down at my hand, unsure of what to do.
Do I wash it? Sanitize it? Chop it off?
And so, without even meaning to, I made it to second base with a ladyboy. I have now joined the rank and file of tourists in Thailand who have befallen such a fate.
I think the best course of action for me now is to do as the locals do, and regard this as a good luck charm. If nothing else, it makes for one hilarious story.
*This post is for Chelsea, who so eloquently said one night, “The title of Kristin’s Southeast Asia memoirs: I Made it to Second Base With a Ladyboy.”
*Special thanks to Dylan Lowe for the photos, and you’re welcome, Dylan, for getting to be the one to witness this account first-hand.
2015 Update: Transgendered individuals have a hard enough time with acceptance into the societies they were raised in without the burden of someone like me writing a post like this. I’m ashamed for highlighting our differences and instead want to celebrate the beautiful (inwardly and outwardly) and strong women who have the bravery to embrace their lives as transgendered individuals. If this post offends you, it’s because I’m a silly girl without an understanding of the difficulty those who dare greatly to be different. I support you in all that you do, empowered woman. I respect your struggle and promise that moving forward, all that I do in my writing and attitude will reflect that. Much respect where it is due.