First Game overall was Indiana Jones and the Fate of Atlantis, back in like early 1994
First console game was earlier, i think it was The Ninja for the Master System.
First digital purchase was on Steam was Titan Quest Gold, Chrome, Ghost Master, Port Royale 2, Thief: Deadly Shadows and Dirt all at once.
On gog it was Jagged Alliance, Jagged Alliance 2 and SiN Gold

The very first game i bought with my own money was surely something on tape for C16, cannot exactly remember, bought so many... on Sega Master System was "Phantasy Star" and for PC "Ultima VI".

The used Commodore 116 my parents bought in 1988 (East Germany...) came with an original tape of "Mayhem" - I still don't know how that game is supposed to work...

The first games I bought with my own money were Battle Isle and PowerMonger for Amiga.

First game I got (pocket money, plus some addons I would say) was Starcraft. First game I bought using own money was HOMM3. First game here Railroad Tycoon 2 (plus other rails titles in small pack). First on Steam Age of Empires 2. On Blizzard Warcraft 3 Reign of Chaos (I played it before, but I wanted to play it once more). This year is 20th anniversary of playing computer games for me, long may it continue ;)

Saved up money from chores and whatnot to buy Black and White. With money from actual jobs, it was World of Warcraft!

Hmm, I bought two games actually. POD, a racing game, and The Fifth Element. Both for PC.

I was in my early teens. I think I was 11 or 12... It's hard to say, but I do remember my parents giving money to buy something for myself since I had good grades. We were in a big store that had everything and I found myself in the gaming section. I don't know why exactly I bought these two games, but there you go.

I have vague recollections of these games. I do remember enjoying POD. I might even buy it here on GOG since I noticed that they sell it now. It will probably be just a nostalgia trip, but could be fun.

The Fifth Element on the other hand... I don't think it was that good.

In general Mickey Mania for Sega Mega Drive 2 (Genesis) and Worms World Party for PC. ❤

I think it might have been when Office Depot & Office Max merged, and I bought Combat Flight Simulator 2 and Age of Empires 2. I regret not getting Mount and Blade Warband, Victoria 2, Hearts of Iron 3 or 4, EUIV, and a bunch of other Paradox games for $1 each. I avoided buying them because I was short on funds and had yet to get a steam account or a PC with a dGPU.

Can't remember that far back. But the first game I bought on GOG.com was Heroes of Might and Magic 3 Complete, followed by Age of Wonders 2: The Wizard's Throne.

Ghostbusters along with my shiny new Commodore 64 back in around 1985.

On Amiga 500: Test Drive II, The duel. (purchased by my brother, since it was his computer), about the 1990, it was my first game, (without counting arcade machines and G&W)
On Megadrive the games that came as a gift with the console, (Mega games I and Sonic). over 1992
On PS1 V Rally (1998)
On PC C&C red alert 2 (2002)
On GOG Witcher 1 on 2015 summer sales

First ever game that I bought? That's a hard one. When I was a kid I would ask for a new Nintendo game for Christmas or my birthday. It's possible I just got money once and decided to spend it on a game.

The first game I have memories of buying myself is Breath of Fire III for the Playstation 1. It was in a $5 bargain bin. Best $5 I ever spent. Got hundreds of hours into that game. I didn't have a guide or anything, so every time I found a unique gene combination by splicing at random it was like Christmas. COOL ANOTHER NEW DRAGON!!! I remember going apeshit when I found Tiamat. XD

But there could have been an earlier one. I played the NES and SNES a lot when I was a kid, and got a lot of games for both. I also bought a lot of PC games too.

My first on GOG is also another hard one. I think I came here when I heard there was a deal on Dungeon Keeper. Either it was free or on sale or something. I then looked around and found a bunch of old favorites. I think Castles II was one of my first purchases.

I think it was Adventure Construction Set by the OLD EA.

Console: Maniac Mansion.
PC: Drakkhen. EGA version packaged in the VGA version box.

With my own money (rather than parents'): Command and Conquer (first one). My friend and I pooled our money, and bought it together. He took the GDI disk, I took the Nod disk.

First on GOG: Evil Genius (sadly disappointing game, after having just finished DK and DK2.) along with Lords of the Realm 3 (sadly disappointing after the first two in the series).

RobotTron 2084 for the Atari 5200.