I want this piercing in my ear called Scaffolding, it looks like this
I think it depends on your threshold of pain, but my friend had it and she's a pretty big wimp and she said that it hurt, but wasn't unbearable. Plus she gets tons of complements on it now!
Their is a girl where i work and she has an x design their. She has two of those that make an x in her ear and she told me they did not hurt at all.
That's also called an industrial... not any more painful then another cartilage piercing...but the healing time is usually longer.. expect soreness for 3 months to a year after you get it...
It hurts like hell having it done but it's worth it. Depends if you got a high pain threshold though. I almost cried.
I have seven piercings in each ear and seven body piercings, and out of them that was one of the most painful. They take a needle and just stick it through the top and then through the bottom. I didn't cry or vomit or anything, but it hurt.