When I go out with a guy for the first time, I'm very nice and really like letting the situation unfold at a natural pace. If I'm out with the guy, that means I already like him, and probably have spent time with him chatting somewhere - a party, a club, on the bus, in the pool .. wherever. I might have had the chance to check out and see what might be lurking under a zipper, either by seeing a bulge or maybe hearing about him from a mutual friend. Either way, if we get to that point where I might play with his cock, we've almost always been kissing or making out first ... if he hasn't made some move to get to my boobs, I direct his attention to them, and let him know I like it. As he's checking me out, if he hasn't taken my hand and put it on his crotch, I usually ask "Do you mind" as I very lightly brush my hand over his bulge and judge his reaction ....the light brushing usually turns into more aggressive rubbing and squeezing pretty quickly, and a handjob or blowjob is about to be served up.