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The second most painful moment of my life so far and hopefully ever: having my right nipple pierced.
The top most painful moment was getting the left one pierced, because whatever about not knowing what to expect making it worse, knowing exactly what's coming is pretty fuckin bad.
Glad I finally got them done, but man not being able to lie on my belly at night for a while is going to be a pain.
Band-aids on your nipples for awhile to keep them from moving around or snagging should help you ease into the piercing.