First cigar was a gift. In 2003 I believe, I was asked by a friend to be a groomsman at his wedding. At the reception, which was at the clubhouse of a nice golf course, the bride's father was passing out cigars. I believe it was an H Upmann (NC) but which I can't say. At the moment we were all inside so I just stuck it in the inside jacket pocket. A little while later the bulk of us were out on the patio and they started lighting up. I didn't inhale and I really enjoyed it. A couple weeks later I wanted to another. It was all downhill from there.
My first Cuban cigar was a Bolivar Royal Corona. I picked some up in Toronto, as I had not yet found CS or any other options. Yes, I paid the 175% tobacco tax there just to try them out. I was like Clark Griswold lacquered up my sled with cereal varnish for the slopes after that.