It took me about twenty years between deciding to have a tattoo and then actually having one and then all of a week after that to decide I will definitely get another. The whole process is really quite exhilarating; from choosing the artist through settling on a design and on to the actual process itself. As for the "pain"... I enjoyed it - it is reminiscent of acupuncture and oddly relaxing.
In choosing the artist, a long waiting list is a good sign! And next time you see work that you like on someone else don't be shy about asking who did it.
I was quite prescriptive with my first design and that's probably how most people are but in future I'll give the artist much more free rein (obviously reserving the final veto).
Enjoy your first tattoo,
@Marmion . I'm jealous