It's painful anytime it's unwanted or you're highly stressed.
First times tend to be like that, but not always. Other sex can hurt just as bad too, it's more about set and setting.
I find that cringe tbh. Just be curious about the other person and talk like a human, not like a creep.
Asking shit like "are you trying to get time drunk?" might sound funny to a man, but it is a legitimate concern for women and makes you sound like an arrogant teenager.
Yeah. That's how it works. If you don't get involved you effectively support the party that wins. Lol