Had my first when I was about 10. My dad bought it for me so I could see that smoking was disgusting. I actually enjoyed it, or at least didn't hate it, to his surprise. But I had no other urges to smoke as a kid. I guess when your dad buys you a cigar at age 10 the mystique and allure of smoking disappears.
Had a few cheapies at 18 and a few golf course cigars in my 20s but didn't really start smoking cigars regularly until I was in my late 30s. I've smoked the equivalent of about 30 packs of cigarettes in my life, mostly when I'm drinking with people who smoke them.
Strangely enough, I started collecting lighters which led me to cigars.