So I'm joining a game that's a bit of gladiatorial combat crossed with professional wrestling, which means that we're as likely to fight humanoids as we are aberrations, monstrous humanoids, and animals
I want to make a lucha libre inspired character that focuses on beating a gentleman with another gentleman.
As far as I've found, most stuff that would allow me to grapple above my weight class doesn't stack with itself and I'm sadly stuck at only being able to grapple huge creatures as a medium luchadore.
What I'm trying to ask is, what can I get so that I may swing a whale at my fellow man?
The Tetori monk archetype's Graceful Grappler ability lets you spend 2 ki points to use their grab ability on any creature larger then themselves. Unfortunately, it costs 1 ki point to grab anything your size or smaller. So, you'd be limited in how often/long you'd be able to do it.
Of course, if you can already grapple anything huge or smaller then its probably less of an issue.
So... I'm pretty sure there aren't actually any size restrictions on grappling? There are on other maneuvers (notably Trip) and there are on the grab ability (which is why the Tetori gets a special exception on that), but you can grapple anything as long as you can hit the CMD. Hitting the CMD is the problem, of course, because bigger enemies will have ludicrously high numbers on that.
The Tetori is still the best grappler for other reasons, though.