Personally, I think earrings are feminizing, even on dudes. If you are attempting to look masculine, I'd advise against getting pierced now.
OK, I think that's wrong, but let me tell you why.
I know way too many guys from all walks of life who have pierced ears. They don't wear all the time, but they are there.
And... There are very fem earrings, sort of fem earrings, and tons of unisex earrings, and some macho, and some very macho. I'm thinking of some nice silver hoop, with a silver wire wrap, with some nice macho detail - thunderbolt, diamond, whatever... a nice tight to the earlobe ring, that's pretty male, girls don't wear things like that, well, nice girls don't, and fem girls don't.
All you're really talking about is putting some good size studs in, treating them with the salt water, or alcohol or whatever they tell you to use for a month and a half, let them stretch and heal, then you only need to wear something every now and again.
You can have fun, I know I do. I wear something on one ear for the first part of the night, and switch it and see if anyone notices. But then again...
I'm easy to amuse.