I had both nipples pierced, and it hurt, and they were the most painful piercings I have ever gotten, but it was only for a second so you should really not be afraid of it at all. If you can mand up enough to jump off a cliff, you can certainly get that done. however, after like a year they still hadn't healed right. I was also stuck wearing underarmour and wife beaters everyday or they would hurt like crazy from catching on my shirt, mostly just when I was skiing or being active though. I would say that if you get them, look into ptfe(teflon) or bio-flex as a steel alternative, they might heal better that way. Maybe titanium. And don't go with anything smaller than a 14 gauge.