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well with every piercing there is a chance of pain
and it depends on your pain threshold
if you find things more painful then most likely it will hurt
I havent got a second hole in my ear but I did have a tragus peircing and that was cartilage and it didnt hurt much
so im guessing another hole in your ear lobe shouldnt hurt that badly
my mum had a second hole done and she said it was kind of uncomfortable when she slept because her ear was getting pressed like
as for the top of your ear(helix piercing) it would probably hurt more
because its cartilage and there also a chance it can ger infected quite badly
and cartilage infections are worse than normal lobe infections
and there is also a chance that it can go wrong then your cartilage can become softer or something and it could ruin the shape of your ear.
anyways the chances are probably low.
http://ezinearticles.com/?Helix-and-Helix-Orbital-Piercings&id=1163283
http://www.ladygodivas.ca/helix%20aftercare.htm
http://www.ladygodivas.ca/lobe%20after%20care.htm
these sites might help
good luck! 
The first answer is right. The bottom part of your ear is more fleshy and will be a small prickling pain but nothing too horrifying. Shouldn't hurt any more than your first piercing in your ears. However if you do go for the one at the top (I have this one) it can hurt a bit more than the bottom as it is more bony and less soft tissue. It is prone to be infected at the top as mine did but that was because I had a ring, once I had a stud it healed.
It all depends on your pain threshold. I'm a super wimp and can't bare any pain and I have 5 piercings: 3 in my ears, tongue and navel.
um...ok I got my 2nd hole done in may (for my b-day) and I was a chicken too. I couldnt decide if I relle wanted to do it or not until I was at the mall. I was sitting in the chair at Claires (where they do free piercings with a purchase of earings) and my bff was freakig out. she got me so scared that suddenly "ping" and my left ear was done. "ping", my right ear. it doesnt even hurt. actually, you don't even feel it. and trust me, if it ddnt hurt me it want hurt you because EVERYTHING hrts me. lol
pce<3
I got my 2nd hole when I was about 7 and both of my cartilages when I was 13. To me it was just a little pinch and it was over. I got mine done in the mall with a gun. It wasn't bad at all. where I get it done if you needed something to hold they have a stuffed animal there so you can squeeze it if you want haha. But really neither of them are bad at all.
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I want to get a second & third hole in my ears, does it hurt?
my birthday coming up and I really want to get a second hole on my ears and the top of my ear pierced but I'm SUCH a chicken and I have a feeling itll hurt!!! Can anyone tell me what to expect, like what type of pain is it so I could be prepared.