When I was a teenager, ALL of my guy friends would jerk off together. Dozens. Sometimes one on one, sometimes parties of 8 at a time. Like everybody came back from summer camp one year and suddenly getting naked and hard together was part of being a friend.
I've met up with guys since and while the orgasm is just as fun, it doesn't mean as much to me from a stranger. I want to feel like this is someone who likes me, then we both share the secret of how big our dicks are together, and play. So it should be someone who I already like hanging out with, even if we've just gotten together for a drink for an hour or so. When a guy comes into my hotel room and strips down INSTANTLY, it loses the sense of excitement. With women it's the opposite, I want to fuck them on first sight. It's almost like I see women as more casual sex, men as more emotionally serious.