I almost think he found a sex-worker online to meet up with in Thailand and then he was acting as her sugar daddy.
You make an excellent point. For someone whose main (only?) outlet to the world is the internet, I certainly can see him setting this up in advance. For socially and geographically isolated people such as Lloyd, every in-person human interaction is embellished. The friendly server at the restaurant he frequents is his “friend”, someone who wrote an article for him at JW Watch is now a “correspondent”, and the woman/girl/ladyboy he paid for sex is his “date”. He can call it whatever he wants. He paid in cash for sex.
Or maybe he likes to watch. Who knows.
The only way he could "date" a sex worker in the context he uses it in, is if he talked to her online in advance of going to Thailand.
I’m sure they have packages for everyone and everything. With the incel movement being what it is, there’s probably a dial for how “aggressive” you want the sex worker to be in getting into your hotel room. A dedicated team of ladyboys are ready on standby to act out your Michael Jackson Neverland Ranch roleplay if you are so inclined and have the money.
Freaky shit - it’s why he went there!