I say go with him. I begged my mom since I was like 12 for one, and at 16 it was my birthday present. He is 18, but it is always better to have someone go with you on that very 1st trip. I'd say just discuss, and even though he knows it's permenent to get something that he will forever love because it is a big decision. Find some shops, check them out, ask to see their work and such and how they go about with the tattoo. If they're not willing to show you then well that's a no. And discuss about putting it somewhere it can be covered for work as you said. It is better so support on something like this than to try and fight it. Us kids have a way with things, and don't necessarily make the right choices. Good luck on that though.