Since my early teens I was always intrigued with the different types of body modification, piercings included.
At the age of around 15, I visited my mother over summer vacation from school. We were hanging out and I realized that she had her tongue pierced. I thought it was the coolest thing I'd ever seen, and knew I'd have it done someday.
So I recall asking my father back home if I could do it and whether he'd sign for me. He, of course, told me no.
So long, and patiently, I waited for my time. I was 17 years old when I graduated high school and moved to live with my mother. I asked her if she'd sign for me, and to my amazement, she agreed. It was my first piercing.
I have since had a labret, both nostrils, my nipples, and most recently a philtrum (or medusa).
All are retired save for my stretched earlobes, tongue and philtrum. I do plan on eventually having the rest redone when time and job (financially, and dress-code wise) allow it.
To date, the philtrum was the most painful, but is quickly becoming my favorite.