2001. Dreamcast was being discontinued so I took the money I had earned working with my uncle to buy one from Best Buy. They were only $50, so I brought a phat stack of $1s in the buy it, but I don't think I bought a game with it. My buddy had a Dreamcast before me and apparently the DC just didn't care about burned discs (as in, you didn't have to mod the DC for it to read burned games), so I had Dead or Alive 2 and some other games burned for me.

Can't remember my first software purchase, but it was a PS2 game.

None

Home computer: Commodore 128 with The Bard's Tale 1, Summer Games and a pretty bad (but cheap) text adventure.

Console: PS1 with Crash Bandicoot, a few months later N64 with Super Mario 64

PS3 was bought with my own cash. Splinter Cell: Double agent was the first game on my own cash. Ps3 version did disappoint me.

PS1 was a prize on a contest. First game Tekken 2 (PS1) again on prize money. I had kept winning prizes for a contest in magazine around the time. Lucky me.

First Playstation, the games I bought along with it day one were Casper: The Friendly Ghost, Ridge Racer and Resident Evil!

Pokémon Ruby Version, along with a GameBoy Advance. I was 8 (and a half) :)