Honestly, no time at all. Don't even need to know her name. I've been with more than my fair share of sex workers in my time and I've routinely gone from go to whoa in under ten minutes.
As for assholes...? Probably about forty minutes to beat on that one. The other time was a little over three hours cumulatively over a few sessions.
My latest story is a racy little piece about what happens when someone cute from work invites you over to watch Netflix and Chill. I'm going to cheat and say "about the same length of time as it'd take for me to consider intercourse with her". There can be a lot context that can change the answer to that question. Barring some heath issues (aka taco tuesday), I'll go down on anyone, likely before I'll have sex with them, whether that's first date or not.
