On the inside of my right wrist, I have my dad's signature. I got it as a memorial tattoo when he passed away this May. This one barely hurt. It's very small, done with a single needle, took about 15 minutes in total to tattoo, and felt just like being scratched. The vibration along my bone actually annoyed me more than the needle.
On my left shoulder, from above the joint onto my upper arm, I have a thundercloud with rain and a rainbow, to always remind me that it takes a storm to make a rainbow - good things can come from bad. The artist actually put a numbing cream on my shoulder because it was a lot of work close to bone, but by the time we were on my upper arm the cream had worn off and it didn't hurt.
On my right lower leg, above my ankle, I have the wand movement for the Harry Potter spell 'alohomora', the one to open doors/locks, with a watercolour background. This one is symbolic of opening future opportunities - and I'm a Harry Potter fan! This one hurt the most because it was very close to bone. I wouldn't say it was unbearable, but it's not the most pleasant thing. I hadn't eaten enough before getting it done so my blood sugar dropped about an hour in, and we had to stop so I could have some soda.
I have several more planned, just making sure I really like the idea before committing - it's with you for a lifetime and they're not cheap, either! But they are addictive and I love seeing them on my skin.
If you're going to get one done, make sure you do your research - find a really good artist and make sure you love what you're getting tattooed. Also, make sure you eat about 2 hours before going, and take sugary snacks or a drink with you so that you can keep your BP/blood sugar up during the process.