Transphobia and Ladyboys

Transphobia and Ladyboys

It was one of my friend’s last nights in Chiang Mai, and I wanted to go out for leaving drinks with him, but he wasn’t too keen on going out. In order to encourage him a bit I told him “If you come out with me tonight, I guarantee you that you’ll get laid.” In my head I just thought, “I’ll try my best to wingman him, but if I can’t find him a girl that way, I’ll just pay a prostitute for him.” He took the bait, and we headed to Zoe’s, the main party area in Chiang Mai. We ordered a couple of beers and then got to work. We talked to a bunch of girls, but nothing was really sticking. At midnight, Zoe’s closed, so we moved on to Spicey’s, a late-night club, and it’s at this point that I fucked up: I lost Steve. Luckily, fifteen minutes before the club closed, a side door opened, and on the other side I saw Steve. Success!

In fact it was better than that - he had his arm around a hot Thai girl. The only issue was that this girl had a friend and she looked bored. Worse for me, the friend was fat and ugly. That said, I’d made Steve a promise and if there was a chance of success with the non-prostitute route, then I had to try my best to make it happen. I began doing a routine I, ever since hearing it from Tucker Max, refer to as “jumping on the grenade” - a noble sacrifice for the greater good. I talk to the friend and 10 minutes later we all leave the club together. I’m a little suspicious. The girl Steve pulled is hot, and Steve doesn’t usually get hot girls. It all seemed to good to be true, so before we left, I asked a few people in the club, “Do you think she’s a ladyboy?” and everyone responded, “No way man.” Anyway, on the way back to Steve’s apartment we stop by our coworking space to grab some beers (you can’t buy alcohol from stores after midnight in Thailand), and as I come back from the fridge the two girls are squatting to pee outside - a good sign; that’s what chicks do.

So we make it back to Steve’s and after a few minutes, Steve goes into his room with the hot chick and I’m left with the fat one. She leans in for a kiss, I pretend not to notice. “Soooo, do you have any brothers or sisters?” I’m trying to stall for as long as possible. Luckily for me, about five minutes later, Steve shouts from his room, “Jon! She has a penis!” Now normally this is something that would throw somebody off a bit, but I’d thought about fucking ladyboys before and come to the conclusion that if the opportunity arose, I’d give it a go, so I didn’t even hesitate - my response was immediately, “Wanna switch?” Steve took me up on the offer and came out of his room butt naked.

Now, Steve’s logic in his head was that rather hook up with the fat girl than the hot guy - fair enough, whatever floats your boat. I think my logic was pretty reasonable too: this chick was hot, like you couldn’t even tell she was a dude - well, except for the dick - and I’d promised Steve he’d get laid, so by switching girls he still had a shot. Unfortunately for Steve, after ten or so minutes he shouted to me again, “Jon! She has a penis too!” Now technically I guaranteed him he’d get laid, but I never said it’d be by a girl. He noped out of the whole situation, took a 30-minute shower, then demanded I give him money so he could stay in a hostel that night rather than in his bed that I’d just hooked up with a ladyboy in. Since it was late and the girls had nowhere to go, they both headed back to mine. The fat one ended up too drunk and passed out on the floor. I hooked up with the hot one again, and then called it a night. They left early the next morning and that was that.


I still saw the girls at Zoe’s regularly after that, but nothing ever happened other than friendly waves. I’d definitely do it again if I were single, and recommend to others to at least try it. Who knows, you might even like it? One thing I find weird about fucking trans girls is the social stigma around it. It shouldn’t matter to others who people have sex with provided it’s all consensual, but there’s a weird stigma against fucking trans girls, and I can’t figure out why. Is it transphobia?

I discussed this on Bitcoin Uncensored recently, and Chris DeRose made the point (paraphrasing), “If you ask a girl if she would or wouldn’t have sex with a guy who’d had sex with a trans person, and she said she wouldn’t, that would be socially acceptable. However, if you change the question slightly and say ‘black person’ instead of ‘trans person’, then suddenly it seems a bit racist if she says no. Why is one prejudice and not the other? Why is there a stigma against having sex with trans people?” I’d never really thought about it much before; I’d never really cared. For me, the core of the issue is all parties consenting and nobody else being harmed from the actions. As long as those two things are met, I can only describe an intolerance to it as transphobia. I cannot think of a sound argument as to why it’s not okay, or why it should be viewed as negative. If you disagree, or have further commentary on why things are this way, I’m open to discussing this either publicly on Twitter or privately via DMs. My contact info is in the section below.

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This post was initially released on 16 August 2017. I pulled it because I thought the writing style could be better. I then delayed release because I was going to talk about it on Bitcoin Uncensored. Finally getting around to rereleasing on 26 September 2017. “Steve” is a psuedonym as he doesn’t want his identity revealing.

Jonathan Sterling

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In March 2017, I quit my job as a software engineer and began travelling around the world. This unmonetized, open-source blog exists to document my journey, share my thoughts, and let my friends and family know that I'm not dead.