On the hurting, it's already been said that it depends, and some people like it some people don't, etc, etc. I'd want to add that it also really depends on where you gonna do it. Obviously, sensitive places (like wrists, or anywhere on the inside of your arm) hurt more. But also places where there's very little fat between the skin and the bones, like feet and chest (although that depends on your build, and gender, I guess.) I have both my tattoos on rather sensitive places (under my collarbones and on the soft bit just under the inside of my elbow) and I must say, it was more than just a sting. I don't mind, in fact, during the second one I almost fell asleep, but if you're really, really, really afraid of the pain, you might want to consider a softer spot than the chest (or gain some weight 😉) Although it has also something incredibly romantic to go through the pain to show her how much you love her.