You've gotten some really good advice here, other than the stripper/sailor comment (was that necessary? But the responses were classic!) so well done everyone! As a person who's pretty colorful in a bathing suit and who was a professional tattoo artist for 8 years, here's my 2 cents:

Go sober. Nothing will screw you up more than trying to manage a buzz and the stress at the same time. And the artist will probably, if they're worth their salt, refuse you if you aren't sober.

Think it through beyond the next 10 years. (Which I think you are!) kids, jobs, old age, etc. imagine all sorts of situations you might be in where it might be visible - would you still want it?

Go custom. I can't stress this enough. Get past the designs designed to be tattoos - anything can become a tattoo. A sculpture, jewelry, paintings, anything is possible with the right artist. (I have an Amazing Stories comic book cover from the 1950s covering one of my calves - it's beautiful! And it has no line work whatsoever!!)

Shop around. Artists talents vary in specialties just like you'd think they might. For example, I hated doing Celtic work and lettering but my coworker loved to do it - he hated doing painting-style portraits and color work which I loved - it all worked out.

And as far as pain/discomfort goes - its your first one, so you're really not going to have anything to compare it to. So it's going to feel how it feels. On the plus side - the discomfort is temporary. I mean really, an hour or so for something that lasts forever? What a deal! Remember too, you do get what you pay for, if the deal seems too good to be true - it probably is. It's a service industry so if you feel you're not getting the service you deserve, you have choices.

Hope that helps a little! Good luck!!