I've got four. The longest time spent under the needle was 8 hours, but that included a couple of breaks for the latrine and getting a drink of water. It got a little irritating towards the end. The one that was the worst was the armband as it went on the inside of the arm. My wife has four and during the largest went to sleep. Our saying is "it's all about the pain, the picture is just the souvenir". I found that on a site talking about tattoos and we adopted it. As has been mentioned, pain is relative. I know a Soldier that would start crying at the sound of the tattoo gun. I also agree with the advice to talk to and question your tattoo guy. My wife says she is done but there are a couple others I'd like to get.

YMOS,
Tony