What a cool thread! Wish I had seen this last fall when it started, not sure how I missed it. Thanks for starting it, Tommy. It's nice to see how so many of the people I know from the boards got started.
I really wish I could remember more details about my first trip. I was 11 or 12, so it would have been arounde 1967 or 1968. Went with my parents who weren't gamblers at all. I was a math geek even back then, so gambling was pretty interesting to me and I learned a lot about the games even though I couldn't play. I don't remember where we stayed, but I'm pretty sure it was at or near Flamingo, so it was probably MGM Grand. I remember trying to sneak into the casinos and getting chased, watching my mother put a quarter into some sort of keno machine (might have been a mechanical thing back then) and winning like $30, also distinctly remembering going over to Little Caesar's and playing a few pulls on their penny slot machines (didn't get caught). I also remember some cheap food: nickel hot dogs and nickel beer in front of some of the Strip casinos, and a prime rib dinner at some fairly nice restaurant (maybe at the Dunes or the Aladdin, can't quite figure it out). Maybe even the Circus Circus buffet (my parents liked a bargain); obviously, no great memories of that meal.
Might have had another trip later, when I was an older teenager; I seem to remember having an adolescent-looking picture of myself in front of the million dollar display at Binion's Horseshoe (the original display, with the hundred $10K bills in the lucite frame). Next trips were in the mid- and late-1980s, but I wasn't really serious about gambling back then. First semi-serious trip was for a convention at the Venetian in 2004; I had studied some blackjack and the casino was too rich for us, so we mostly walked down to the Frontier or the Ho to play. Started getting serious around 2007, been coming twice a year since then (almost all downtown).