Once. Sukhumvit. She was flawless — small frame, soft voice, zero red flags. We chatted outside a bar for twenty minutes. She was witty, funny, even a little shy. I genuinely thought I was talking to a shy, petite Thai girl who just happened to be stunning.

We got back to my place and everything was great… until the pants came off. And there it was — surprise delivered.

I froze. Not angry, not freaked out, just genuinely stunned. She looked at me like, “So…?” and I had no idea what to say.

In the end, I just laughed. We didn’t do anything, but I gave her taxi money and said, “You should work in Hollywood.” She laughed too.

Lesson learned: never assume. But also — no shame. She was cooler about it than I was.

Yeah, it happened on my first trip. I was in Nana Plaza chatting with this gorgeous “girl” at a bar — slim waist, beautiful smile, killer legs. She leaned in close and whispered in a deeper-than-expected voice. That’s when it hit me. I was shocked, not disgusted — just surprised. I told her the truth, and she laughed. We kept talking for another hour. That moment actually broke a lot of my stereotypes and opened the door to one of the best trips of my life.

Once, I took a lady from Soi Cowboy back to my hotel without realizing. It wasn’t until we were both undressed that she confessed. I didn’t freak out, but I did decide not to go through with it. We ended up watching Netflix and drinking Leo beers. It was awkward, but kind of sweet. I learned two things: always ask if it matters to you, and don’t assume anything — some ladyboys are damn convincing.

Yes — at a bar in Patpong. She looked like a model, soft voice, perfect body. I only realized the truth when things were already getting hot. She saw the look on my face and said, “You still want me?” I paused for maybe two seconds and said, “Hell yes.” No regrets.

I was at a karaoke bar in Silom when a girl sat on my lap. Only realized when she grabbed my hand and let me feel everything. I froze. Then laughed. Then stayed the night. Best surprise ever.

Once I took a freelancer from Walking Street back to my room, and only found out she was a ladyboy after the BJ. No shame—she was hotter than most girls I’ve been with. Respect where it’s due.

Yeah, it actually happened to me once on Walking Street in Pattaya. I was drinking in a small beer bar near the pier, chatting with what I thought was a slim Thai girl. We laughed, she ordered a couple of tequilas, and only later one of the staff leaned over and quietly said, “She’s kathoey.” I’ll admit, I was shocked for a second, but honestly? She was gorgeous, fun to be around, and it didn’t change the fact that I was having a good night.

Another time in Bangkok on Sukhumvit Soi 11, I ended up sitting with a tall dancer who looked straight out of a fashion magazine. Didn’t realize until she mentioned it herself. Instead of feeling tricked, I was more impressed — she looked better than half the gogo girls I’d seen earlier in Nana Plaza. Phuket gave me a similar surprise on Bangla Road — a freelancer outside Tiger Bar who was so convincing that my buddy swore she was 100% female.

My reaction? At first a bit of confusion, then curiosity, then respect. The truth is, once you’ve spent time around Soi 6, LK Metro, Sukhumvit, or Bangla, you stop being surprised. Some ladyboys are more up front than others, but in Thailand, most don’t hide it — and a lot of them are way more fun than the “regular” girls anyway.