I started playing when I was probably 4 or 5. As I recall, my mom sat down with my big sister and I and had us make some characters just to get our imaginations cranking.
I should probably ask my sister and see what she remembers. Another time.
Mom was always good at coming up with creative activities like that for us. We were already fans of The Hobbit, Lord of The Rings (ok, my sister was a LOTR fan, but it was still a bit over my head) and the Shannara books, so we both thrilled at the idea of molding our own fantasy personas and experiencing our own fantasy adventures.
I don't recall if mom put us on an adventure or if she just turned us loose after that. I know my sister was primarily the DM, and we managed to recruit a few of the other neighbourhood kids into our game before long.
We loved it. I don't think we played it that frequently, or that hard, but it stuck with us. My favorite characters in those days were a Dwarf Fighter named Phasiden and a Half-Sandman Fighter (The Sandman image in the Fiend Folio haunted me) whose name escapes me. I was always drawing, so over the years I would pore over the books again and again, and I never failed to find new inspiration. Looking back on my life nearly 30 years later, I'd say D&D has been more of an influence on my creativity than any other single entity.
I have scads of characters and monsters I've drawn. I have folders full of adventure ideas and NPCs I dreamed up. I have hours of footage of medieval fantasy videos my friends and I made in high school and after. I wrote a medieval fantasy script that got made into a low-budget indie movie and went on to get developed as a TV series at Paramount, where it died.
Recently, following friends of friends, Zak and Mandy of Playing D&D With Porn Stars on Twitter and SG led me to Zak's afore-linked blog, which then motivated me to dust off my shelf of D&D books and start digging around on the internet. I was and am amazed at the volume of dialogue, ideas, and information that is out there.
D&D hasn't been far from my thoughts ever since.
I wrote my group of close friends whom I regularly engage in "family" activities with, and proposed trying D&D together some night. They are all for it.
Now it's up to me to put the pieces together.