Finally I find someone who is a fan of these! I've always wanted one there! But the thing about them is you need a touchup every once in a while because the ink will fade. Most times, they will fade within the first month. The upkeep of them is greater than any other tattoo. As far as pain, it really depends on your pain tolerance, but it is said the closer you get to the teeth, the more it hurts. But it hurts a lot less than places like the foot or ribcage. Your lip has a lot less nerve endings there (and thats what makes it hurt more or less).