My first actual experience roleplaying or my first experience roleplaying? If it were my first actual experience it was, to say the least, a brutal one where I found myself greatly out of my league. At my best, mind you quite young at the time, I was at most a "high free", "low casual" sort of writer and roleplayer, and stumbled on to a group who were what one would call "advanced" or "high casual" here on the Roleplayer Guild. Needless to say, they thoroughly enjoyed utterly dismantling me and effectively humiliating me. Fortunately I was observant enough even in youth to avoid obvious cliches and pitfalls, but my weakness was that I was still very uninitiated to advanced writing and my concepts were not elaborate despite staying away from the overt failings. A few months, a year of that even, and they had more or less made me into an actual roleplayer well beyond my age at the time and finally accepted me rather than treat me as a child, often speaking down to me and critiquing all I did. I hated the experience as much as I desired to improve and once I at last met their usual standards they embraced me as their own company; I felt I had well earned it, quite a rewarding experience too.
As for my first experience roleplaying, between being hazy and disjointed memories, what few I do even have of that time, I have been doing so since at least my time in elementary school. I never quite stopped and my character, rather my persona, only ever evolved and into new mediums. Nothing was truly lost there, the archetype refined, but when I was young I recall the reactions of others to be... less than accepting. Pouncing the other youth and or getting into brawls, attempting to slink around in the shadows or around brush, trees, and grass never went well. The game of tag was more a game of "Hunt and Chase", as being "it" was just part of taking on the identity and having an excuse to act it out. All of it was roleplaying from the start.
As for the next question please leave out names and do attempt to be ambiguous about it if that person is here among us on the Roleplayer Guild, but what was the worst, most egregious character you have ever encountered in roleplaying? Please do elaborate, we all love the horror stories here I am sure.