Dont be so shy, i know i was like you before, but eventually the feeling of wanting to kiss my girlfriend overcome my shyness and that's what break the habit, i dont know if its the same for you.
For starter, you dont have to kiss her just because you want to make out, try kissing her on the lip when shes not expect, just a fast touch on the lip. Its a fast kiss so that should be too much of a problem for you, sometime that could turn the situation into making out, its all depend. Or you could just laugh it off "hey i never done that before, hahaha" You have lots of sweet words that you could use in real live that you just wrote above, "She's beautiful in every way imaginable" try saying something like that to her, then kiss her on the cheek.
If you so uncomfortable with initiating everything, you should tell her. Talk to her, tell her something like you will try to initiate things, but that you are shy and maybe she could help you out a bit. If she's a kind of girl that like her men to take the driver seat, then dont talk to her about it (unless shes really understanding) and start with something small, ask her to go on a date with you, make decision on where you want to go eat, ask her out to a movie, then you should feel more comfortable with initiating things.
Hope this help, i, too, dont like initiating things, but it got alot better over the past year
Good Luck with Amy