The first cigar I remember smoking was a Dutch Masters. I was way too young to be smoking (7th or 8th grade). I don't remember much about it but I liked it.
My buddies bought me my first premium cigar on my 18th birthday. I think it was a Punch but I'm not sure. I do remember that it was like 9 inches long!!! We went to our local indian casino (which allowed 18yo at the time) and I remember the security guards wondering if they had to confiscate the cigar because it could be used as a weapon

I smoked that thing for like 3 hours!!