I'm not even watching this and I'm getting second-hand cringebarassment from reading the comments here.
Back on the topic of Drex, I found his very first appearance on Nick's stream from October 2018, and he brings up that
he just went to Sanctuary (bondage/swinger club) in Portland. In a later stream when he mentions this place, he says it happened near the start of his relationship with this girl who was his sub, so it's looking like they probably started hooking up sometime in 2018. In this stream, he pretends like they didn't know what Sanctuary was when they showed up, and that he went there with 3 female friends. If anyone has time, I'd suggest watching the whole thing, it looks like Drex launches into talking about "the lifestyle" pretty early on in the show.