I’ve never had sex with a woman but I assume there’s a level of expertise that comes when someone has had sex with multiple women. There’s an episode of Nip/Tuck where the doctor realizes the woman he’s having sex with is trans based on the shallowness of her vagina. I was like “Thats ridiculous”, but hey, the doctor was a whore and also knew a lot about vaginas. Maybe, of all people, he would know.