I know anal sex usually hurts at first, but does it hurt at first EVERY time or what? I’ve tried googling and I can’t find the answer I’m looking for. Like, if it hurts at first every single time I try it, I’m not freaking doin it. That’s like losing your virginity every time you have sex. Now, if it just hurts the first few times you try it, about how many times do you have to keep doing it until it doesn’t hurt?