When I had my nipples pierced, I found it hurt a lot less than I thought it would. It was more like someone pinched me really hard (which is exactly what happens) and it was gone almost immediately.
I was incredibly sensitive for a few days afterward(Oh, how I wish I had stayed that sensitive!!). To the point where even my bra was....erm.....
distracting.
I also suggest getting them both done at once, but for a different reason. I had my done about six months apart. When I went back for the second one, my original piercer had moved. The new was just as professional, but he didn't line the piercings up exactly right. Now, my left 'hole' sits slightly forward. It's not a big deal, and I'm the only one who can really tell, but you know.... I guess I'm just anal like that.
So, for purely symmetrical reasons, I'd go with both at once.
They're really not hard to take care of. Follow the after care instructions that your piercer will give you- religiously.
And here's something that might come in handy: don't let your father give you a big bear hug the day after you get them done. Ow!!
I reccomend getting hoops to start with, as they will turn easier, and you need to almost constantly turn them, anyway. Also, if you're like me, your nipples will be slightly swollen for a little while, and if you want barbells that fit snugly against the nipple, you'll need to wait.
I think that's everything I have to add. Let me know if you have any other questions.
Good Luck!
