My grandfather taught me to play when I was maybe 9 or 10. He never let me win.
I didn't start studying the game until years later. I worked at an all-night coffee shop called 'Notsuoh' in downtown Houston, TX. The owner was an avid player, and there were chess boards all over the place, and this big box of pieces from like 100 random sets. The engineers from the NASA base would come in and kick my butt mercilessly... I learned a great deal from those beatings.
I clearly remember the first time I beat one of my best opponents. Maybe half the pieces left on the board, and he hung a rook. I dogpiled him with a knight, a bishop, and a rook, and mated in the center of the back rank - he had never castled.
I remember being quite proud of having my pieces well positioned to take advantage of his mistake, and finish the game quickly. I remember what he said to me: "See, that's what you can do when you stop feeling sorry for yourself 'cause you ain't the best, and just play the game." He was absolutly right. ;-)
I remember my first ever draw. My grandfather taught me to play when I was about 4. He was a fairly strong tactical player (about 1600) with little-to-no opening knowledge, which clearly rubbed off on me as he was my only opponent for another couple of years. I would visit regularly after school and we would play about 10-15 games a week (every single game was a Giuoco Pianissimo). He would encourage me to use as much time as necessary but would never forgive a touch-move violation.
Day in, day out, he would win every single game. Then one fateful night, my grandparents came around for dinner and we decided to have a game. Maybe it was the homeground advantage but suddenly I was up a piece... then another... and another! Before long I had my Queen and Rooks positioned to mate-in-one with some minor pieces floating around and then sure enough, with a lone Queen, perpetually checked my King.
I did win my first game a few weeks later but it wasn't as memorable. Soon after I started playing in chess clubs and learnt about other openings. I grew particularly fond of the King's Gambit - he didn't win many games against me after that