It depends on the situation for me too, of course. I'm more bold with guys I meet on sites like MM4M, MF, rentmasseur or at spas that are more famous for being "friendlier." In fact, for the independent masseurs, I almost always start my request asking for them to be nude too. I hate wasting my time and dealing with "oh, that's more money" if they find out what I want later. With a new masseur in a spa, I'll make my desires known slowly, like you mentioned with a hand brushing his thigh. Once that seems to work, I make more obvious moves to move things along at a quicker pace, as I mentioned above, in order to get to the good part.