I got my first tattoos at 19. Small wings on my back, between my shoulderblades, just black-and-white flash. An angel wing and a devil wing. I got them just to get them, because I knew I wanted tattoos, but also knew that I could end up obsessing over getting something 'meaningful' for my first one and then never getting one. So I just grabbed an idea and went in and got them.
Didn't get another until I was in my 30's, now have 4 large-ish tattoos: upper chest, left ribs, left shoulder, and I just got those first small wings covered up with a much larger tattoo that fills the middle of my upper back.
Upper chest and left shoulder didn't hurt all that much, felt like a thumbtack being scraped over a mild sunburn is how I'd describe it. Ribcage hurt like almost nothing else. That was a 5-6 hour marathon of torture. Middle of my back was also pretty bad, bad enough that I immediately sent my wife a text saying "You gotta remind me of this pain if I start talking about another tattoo."
I'm 42 now and I think I'm likely done with tattoos. I have a couple of ideas that are still kicking around, I kinda-sorta want something on my right arm to balance out the tattoos on my left side, and I think hand-roses look seriously badass, but I'm a teacher and there aren't a lot of schools that are okay with hand-tattoos.