Is it awkward to make the first move towards a hand job?

I'd say don't give him a heads up, because the waiting will be difficult for him. Just surprise him with it when you get him alone. I'm sure he most likely is going to enjoy it!

Do you massage that area while making out? It would be easier to transition to giving a hand job if you've already been touching him while clothed.

I would say go ahead and make the first move, I doubt he is going to stop you. If he does not return the favor, just tell him when he is done. That it is your turn.

Honestly, like Bduffman, I wish there were more girls like you imo. Most guys would probably love it haha I know I would xP, but yeah there is the chance where he might be not comfortable with it so I would say go with what budphillips said, :].

Exactly what he said. Don't ask him. Go down, stall, not too long though, he'll stop you if he doesn't want you to continue.

The next time you guys are laying around, kissing, doing whatever (you don't even be have to kissing), if you have you hand on his chest you can casually start moving it down toward his pants. This is the way that the majority of girls have gone about this with me. Some girls like to play with the elastic part of the top of the guy's underwear or boxers, right before they start putting their hand down his pants. If he doesn't want you to do that, he can stop you or get up or move your hand away. If you slowly do it, it won't be a problem.

If he stops you, then you probably want to ask him what's up. Everything should happen slowly the first time, I imagine.

Damn why can't I find more girls like you, next time while your passionately making out, you should tell him to go all the way

While your making out, start touching him in those spots, if he likes it, he'll move your hand around to the point where it makes him feel good. if he doesn't like it, he won't do anything but to stop making out... but I'm sure he'll be horny enough to do it (x

The answers that suggest sort of moving your hand(s) in that direction slowly/playing along the top of his boxers/pants basically describe what I always do. I find that if like you've said its sort of been suggested that things might become more serious and neither of you has objected to it - you are both probably just shy to start. If you move your hands slowly downwards on him and kind of play around that area he will have time to guide your hands elsewhere or stop you in some other way if he isn't interested. Chance is he is though. I've never had a guys stop me. I just think you need to be sure that this is really what you want to do before you start... he probably won't appreciate you quiting halfway. Good luck.
oh and a random tip : if you are uncomfortable in whatever position you are in, move or ask him to move. Trust me, he won't mind much and it will be better for him too if you are more comfortable and able to move the way you want.