Comparing the pain of nipple piercing? Trying to gauge the levels.

So I'm trying to think of the worst pain I've endured, I've never had children, but I have had an IUD (paragaurd) removed which does involve opening the cervix just barely. That was by far the worst but also brief, like the pain with piercing generally is. I have insanely sensitive nipples, but would like an increase. Without being to NSFW I've been using butterfly clamps more often, so I'm also not completely foreign to pain in that area.

Anyway, the point being I was hoping someone might have some comparative level of pain they've experienced that I might also have experienced..... Just want to be as prepared as possible. Also, how long till they stop hurting? Do they hurt during healing time, and do they need to be kept out of play for a long period?

Thanks!

Just to clarify. I have no nipple piercings yet nor have I had any in the past.