Everyone, as you probably know, has different levels of pain tolerance. Something that hurts one person badly, may not be as bad for someone else.
Generally speaking, though, the most painful areas to get tattooed are:
1. Any Joints (the crook of your arm, armpit, backs of the knees, etc.)
3. Top of the foot.
4. Inside of the ear.
5. Top of the head.
6. Between the fingers (and TOES)
7. Any place on the body where there is not a lot of "weathering" i.e. soft, tender skin.
8. Right near your areola. (Damn near peed myself on that one, no lie)
Least painful? Forearms, back (right over the spine- the love handle area hurts like a bit**), biceps, neck (sides), calves, kneecaps, elbows.
Personal tattoo collection and 16 years as a tattoo artist.