>>82911286
>How does that come up in the first place
Talking about history and a boyfriend comes up and you ask what she liked about him and she makes a joke about something he did well in bed. Talking about cosplayers and you mention a preference and she asks for more details. Any number of ways as long as you don't shy away from sexual topics in conversation like a virgin autist.
>how do you get into a conversation like that with a woman at all?
Add someone from /soc/. Get the instagram of someone you go to school with and message her. Shoot the shit with a mixed-gender group of coworkers in the break room.