My first cigar was a montecristo tubo. It was NC, of course... nothing exciting to say from it.
A more interesting story was my first full bodied smoke. I mustered up some guts and got a La Flor Dominicana DL-700 maddy for my first cigar that wasn't mild or medium. Bad mistake... especially on an empty stomach. I smoked the entire thing sitting down, with a can of coke... and as soon as I stood up I felt light-headed and slightly nauseous... I also learned that day how to puke without getting any on myself. My seersucker suit was saved for another party later that day
