I've got one on my right shoulder blade and I don't regret it. It's coverable if needed, but in general I don't mind if people see it, because I'm proud or at least don't mind, what it represents. Which would be my grandfather. He's a lovely man, who has done much, and seen a lot in his life, and I love him dearly. So when I turned 18, or was about to turn 18 I decided to get something that represented him on my shoulder. Or rather, when I was 17 I started considering it and after talking it over with my parents for nearly 6 months (including designing it myself, for the most part) I got my tat. Which my parents paid for (thanks mom

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It turned out to be a fender stratocaster hanging from a paraglider (picture http://www.flickr.com/photos/49692641@N00/3215011839/ ). On itself that sounds whacky but it makes more sense when I tell you that my granpa is (he's 69) a paragliding instructor and indeed paraglides himself. And when he was younger he used to play a fender strat, a wooden one at that. And lastly, he has two necklaces which he always wears, one of them with a paraglider and the other with a fender strat.
The actual process of getting one wasn't all that painful for me. The guitar even tickled because the tat artist had to place his hand on my arm and I'm really ticklish. The straight lines really hurt, because it felt like he was slicing something open. Which he was. And the higher up he got the more it hurt, due to my permanently knotted neck muscles. But all in all it only lasted half an hour and the it's a very strange sort of pain. Yeah you're getting your skin sliced open or punctured open, but it also vibrates, so it just felt weird. I still claim that getting a cavity filled without being sedated hurts far worse (I hate my dentist, no wait, ALL OF THEM).