[nsfw?] What kinds of situations allow you to bring up the conversational topic of sex the quickest?

I come from a background where people almost never talk about sex—not even when they are drunk. Ribaldry with people I do not know very well can make me very uncomfortable although it also attracts my intense interest, because for whatever reason, I am intensely curious about the role that sex plays in other people’s lives.

I have found online that I can generally ask questions that I would consider to be outrageous in person, but people don’t seem to mind them at all online. How many partners have you had? When did you first start getting sexual? How often do you cum? Do you watch porn? Are you interested in me that way? Does size matter? Oh the questions seem endless.

Online, people will answer them—I don’t know why. Maybe someone could offer an explanation for that. But I rarely, if ever ask them in person. However, I have an outrageous friend from my support group who will ask these questions that I’m too whatever to ask. And the women answer them. It’s a crazy, wild form of flirtation (I know I don’t intend to go anywhere with it, and he seems not to care) to me. It makes me a little manic, to tell the truth. My mind starts racing. It’s very exciting (mentally, not really physically). I really enjoy that jazzed up feeling. It just feels full of… potential, I guess, even though I know nothing except flirtation will happen.

But it really never happens in reality for me. Just virtually. What about for you? Do you talk about sex with people you have just met? Under what circumstances? How do you get to that topic? Why do you think people are willing to talk about things we are trained to keep behind closed doors, mostly?