I started young. My cousin and I, when we had the rare opportunity to see each other, spent a huge amount of our time together roleplaying. Whether that be in our grandmother's backyard, or making up our own story for games that we were playing on the gamecube, we both really enjoyed the idea of having a new story each time. Eventually when I got my DSi, I found a website called 3DSPlaza that had a lot of others around my age in the chatrooms, some of which were roleplaying. I was very interested, and thus my sleep schedule got entirely fucked as I would stay up well past 5 AM each night as an 11 year old boy. I loved to roleplay, and eventually I had honed my skills to the point where I kinda refused to roleplay with most of the people on the site due to their incompetence.
That led me to stop roleplaying for a few months until I had started to borrow my Aunt's laptop on weekends. This let me play games like Team Fortress 2 and Garry's mod, the latter of which I had found out there were roleplaying communities on as well! I started playing Half Life 2 RP, and still do to this day on the same community. Last summer I was really in the mood to roleplay, and found this site after a google search, now here I am.