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Whatever you do, make sure that if the tattoo is supposed to have any special meaning, make it a theme that you'll always be proud of. Or, as many people do, use the tattoo as a way to remind a much older version of you what you were thinking/feeling at this age.
Myself, I've picked designs that I know I will always hold dear: the first picture I ever drew that I was really proud of (a tribal piece). I'm a much better artist now, but it will always remind me of how I got my start in art. For my other two, I'm working on a large grouping of three hearts, each one representing a facet of the Holy Trinity. Given that I was raised Christian, I figure that if I ever get to a point where I regret that tattoo, then I'll have bigger problems in my life than a tattoo (i.e. some very large spiritual changes) kinda like a colorful, permanent WWJD bracelet.
As for the pain, eh, it usually isn't that bad. I got my first one done a while back (right bicep) and it wasn't too terrible, the second one is on my upper left arm and was done when I was around 300 pounds, the extra padding lessened the pain greatly, however my third was done last Tuesday (left bicep/tricep) and hurt a little more, since I no longer have a great deal of extra weight on my upper torso. So, I'd have to say that it's all dependant on your body type, the placement, how the artist tattoos (my first one was done by a guy that drives the needle hard..a little more sting), and your tolerance for pain. I'd compare it to a sharp sunburn.
But, if you choose the right artist/design (I tend to design my own or have them drawn up just for me) it's well worth the temporary discomfort.
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it's all about self-indulgence
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