On the subject of “that guy” who always plays sexy women... Sometimes “that guy” is legitimately trying to explore a broader range of gender expression and identity. I mean, if their portrayal of women is making other people uncomfortable, obviously talk to them and try to discourage the problematic aspects, and if they aren’t willing to respect others’ wishes, probably ask them to leave the group. But sometimes they’re just fumbling through an earnest attempt at playing another gender, and don’t mean to come off the way they are.
On the subject of experiences in middle/high school with players portraying other genders, one of my best friends always played women in D&D. Those characters never came off as creepy or disrespectful, but it was a noteworthy pattern. Now, twenty-odd years later, turns out she’s trans. She’s far from the only trans person who used roleplaying games as a safe way to explore their identity before fully coming to terms with it, and I think that’s a big part of why we get so many LGBTQIA folks in the hobby, despite it having a history as a bit of a boy’s club.
So, yeah, I don’t question the genders players choose to roleplay. And if someone’s uncomfortable, we’ll talk about it. But restrictions around who can play what gender don’t fly at my table.