To answer your question I think it's a little bit of column "A" and a little from column "B". It really depends on the escort... his physical limitations, how horny he is, whether he's in it to have fun too, etc.. 😛
I would say out of all the providers I met most of them orgasmed/came. I have never asked/told an provider before the fun began, "I want to see you cum." For me personally, it kind of takes away the experience, to say that in the beginning. Although I do understand it's a very import outcome for some clients. No pun intended. So i get why people ask upfront.
I have had a few providers ask me directly if I wanted them to cum after I had already did. I'm easy going... so I usually say, "if they want to." Most have. Some don't. For me the best is when it's obvious the provider wants to cum without me prompting. Even better when I make them cum and they didn't expect it or they're in the moment. I think one of my hottest is after a long session, I orgasmed and sat up to stretch at the edge of the bed. The escort says to me, "where are you going. I want to cum too"... raging boner in hand. I reassured him I wasn't going until he was happy as well.