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Honestly, don't worry about the pain. Yeah, it hurts, but it's part of the process. Pick a good artist with a light hand and you'll be able to tolerate the pain. The idea of gaining a piece of cool art or jewelry (in the case of piercings) can help you overcome the usually mild pain. I mean, I'm scared to DEATH of needles but I've sat for over 25 hours of ink (12 hours in one sitting) and I pierced my own frenum (google it if you're not familiar).
As far as a design, get something that means something to YOU. I can't stress that enough. Most of my designs are custom, or at least taken/modified from flash drawn by tattoo artist friends of mine. I'm almost guaranteed that I'm not going to see the same piece of work walking down the street on someone else's body.
And I'll second (third?) the recommendation to check out bmezine.com. Hang around there, and get a good idea of tattoos and the community that surrounds them. You'll learn a lot that will help you prepare for getting a piece of your own.
As for the weight loss issue, it is possible for tattoos to change with weight loss, but in my own experience (I've gone from 300 when I got my first piece to 235 as of my last piece) the ink didn't change THAT much.
Good luck, and feel free to PM or e-mail me with any questions.
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it's all about self-indulgence
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