Everyone dreams of wild nights in Thailand — gogo bars, massage parlors, short-times in Pattaya, long-times in Bangkok, or late-night adventures in Phuket. But nothing messes with your head quite like your first time with a Thai ladyboy. Some guys come here thinking they know what to expect, but trust me — if you don’t know the etiquette, you’ll make mistakes. I did.

My first Bangkok ladyboy experience was inside a neon-lit gogo bar on Sukhumvit. I was nervous, didn’t ask the right questions, and didn’t set clear expectations before heading to the short-time room. I paid too much for drinks, agreed to extras without knowing the price, and rushed into sex before I had even relaxed. Instead of enjoying the blowjob, the cowgirl ride, and the unique energy that Thai ladyboys are famous for, I ended up worried about money and time.

The same lessons apply whether you’re chasing Pattaya ladyboys on Walking Street, barfining a Phuket ladyboy from Bangla Road, or finding freelancers in Bangkok:

Always negotiate price upfront — drinks, barfine, short-time or long-time, and any extras like CIM or anal.

Take your time — the best sex happens when you’re not rushing. Ladyboys in Thailand love to show off their skills, from deepthroat blowjobs to wild doggy-style sessions.

Be clear about what you want — oral sex, full service, safe sex, or just company. Miscommunication ruins the night.

Respect goes a long way — many ladyboys will give you the experience of your life if you treat them like a person, not just a quick thrill.

So this thread is for guys to share their first-time ladyboy mistakes — the expensive lessons, the funny stories, the surprises in bed — so newcomers don’t repeat them. Whether it’s in Bangkok, Pattaya, or Phuket, let’s talk about what went wrong, and how to get it right the next time.