I have four: a black squiggly thing on my thigh, a rubbish series of coloured blobs on my left lower back that is partially covered now, a swirl of blue stars on my left front shoulder (sort of in the nook between collarbone and arm, iyswim) and a full back piece (neck to hips) that is currently languishing half finished because life stuff keeps getting in the way. When it is finished it will cover up the crap coloured blobs thing, as well as looking mighty fine.
Being tattooed does hurt, but there's so much variation between people and locations on the body. Generally speaking less fat = more painful, but it's not always the way. Most people find their ribs unbearable but I know some who've breezed through that while saying they found their calf or inner arm the worst. It's probably best not to go in with a preconceived idea of how much it will hurt or what it will feel like, as the best way to manage the sensation is to stay relaxed!
Also make sure you eat a good meal before you get inked - carbs, lots of fluids, and take a sugary snack in case you start feeling faint midway through. Cake is always good in these situations
Definitely find a good, reputable tattooist - ask to see their portfolio, ask them about sterilisation and other hygiene procedures, try and talk to some of their other clients to see if they're satisfied. A good artist will be happy to go through all this with you.
I love my ink and wouldn't be without it