I started with an Atari XE (can't remember which, think it was the 65) and a tape drive. http://www.atarimuseum.com/computers/8BITS/XE/xesystems.html That got returned to the stored and traded in for a Commodore 128D. Had prolly 200 games for the Commodore. The ones I remember playing hours and hours on were Super Huey, Beach Head I & II, One on One (Dr. J v. Larry Bird I think), and Way of the Exploding Fist (I think that was the name)
Got my first PC in 1992. Opened the case as soon as I got it home, poked around, then loaded up "The 7th Guest" and my cousin Justin and I played it the rest of the night. Next came Myst. The rest have been a blur as there've been a lot.
Of course, I played the Atari, Odyssey (KC Munchkins was great), Colecovision, Segas stuff, and all the Nintendo varieties. Also have had both playstations. Never have played an Xbox tho.
Then, in college, Lunk called me about a game called Team Fortress Classic, and then later about a beta of Counterstrike. Think those were my first real "online" games.