I don't remember my very first, cause it was back in the 80's and it was part of what I know as a PPP. Soon after that I made my first purchase, and I'm pretty sure it was a Davidoff. Cause that's what the guys I worked with smoked. My first cc was with my then-BIL on vacation at OBX, and it was a RyJ tubo.
I smoked on & off for a number of years--usually the same few brands--and then took a "cigar break" for a long time. About 4-5 years ago, I picked up an Acid

at a Long Beach B&M and I got roped back in. I only smoked that one Acid, but it opened my eyes to the variety of what was on the market.
And a few years after that, I found Club Stogie. And it's been downhill ever since.