The first game bought my own money was a game called Journey on tape for the Commodore 64.

Thanks to VICE and quick save I completed it in 2006.

First game I ever personally bought was Pandora Directive.

Age of Empires II: The Conquerors. My brother had the base game, so I was familiar with it. I received some money (£25, I believe) as a gift, which was exactly enough that I could buy the expansion; I remember it particular appealed to me because it included the Aztecs, who as a child I had an obsession with. I found it really cool fielding eagle and jaguar warriors with their obsidian-edged weapons. When I tried out the other new factions, I also found Attila quite fascinating, and I loved the turtle ships used by the Koreans.

Yars' Revenge cartridge for my Atari 2600.

It was Call Of Duty WW2 bundle on Steam, which includes Call Of Duty and United Offensive expansion, Call Of Duty 2 and Call Of Duty - World At War, plus Call Of Duty 4 - Modern Warfare, on the same day. All great Call Of Duty games in a single purchase. I wish they brought them on Gog as well and introduced the proper anti-cheat for all of them.

Heroes of Might and Magic 3, also my favorite game of all time, who would've guessed

Wrong. I am playing games since the late 90's, started with Sega Mega Drive. But that was my first purchase I made with my own money. All my PC games have been cracked throughout these years. I have started buying them recently when I got my credit card, in order to show my support and gratitude to developers and publishers.

The first one I bought myself was Icewind Dale. I still have it, too, I believe complete. I had a couple other games that my parents bought me before then, I remember I had wanted Warcraft 2 because I played the absolute shit out of the demo, but the store didn't have it so my dad bought me the first one. I did end up getting my dad to buy me the Warcraft 2 Battlechest at a later point though.

First game I actually ever purchased was on of those pirated "100 in 1" game pack CDs. Lots of history I picked up from that- Abuse, Aladdin, Lion King, Hexen, Heretic, etc.

First actual legal game I purchased with my own money was probably Grim Fandango. A very worthy purchase, near the end of the LucasArts store, where I just got the jewel case.

Technically, "Google Maths". Not exactly a comfortable "choice", as the family computer was originally purchased for educational reasons, and I had only a few options to "choose" from.

The first non-educational one purchased from my own money...Quest for Glory. A cheap re-release boxed copy of the original version (CGA/EGA). 4x 3 1/2" floppies, black & white paper manuals. Still got the floppies...and probably the manuals somewhere.

Pokemon Ruby for Game Boy Advance.

I actually have no idea.... But the first games I played were usually bundled with gaming magazines we used to buy. I still occasionally buy them when they have a good game bundled with them.

My first bought game on GOG was Grim Dawn.

In the beginning of my time of PC gaming, I bought a lot of games from the bargain bin, just getting attracted by the images of gameplay on the backcover. There where no (or at least I wasn't aware of) internet sites where you could check reviews before buying.

So many where a bad buy. The first ever game I bought (if I remember well) was called Destiny, a game that promissed "World Domination from Stone Age to Space Age". The game world had two views: a close up of your land and a zoomed out view where you saw your land on the planet viewed from outer space. However, once zoomed out, the key that should zoom in didn't function. I sent a support request (not by email, but by regular mail! all the way to the address somewhere in San Fransisco in the United States), but never got a reply nor a refund.

The laurels should actually go to the first game that I bought (after several bargain bin bad buys) and actually liked and played a lot: Age of Empires.

Tricky question, probably Colin McRae Rally 2.0.
First on GOG was KSP, then Everspace, and then Race Driver GRID when it was selling for £2 before it left the store. The oldest game I've played is probably Sim City 3000, SMAC, or Theme Hospital (whichever is older) all of them older than me.

Edit: Correct capitalisation.