The first video game related item I bought from Amazon was a Wii in 2010. It took me several years before I trusted them enough to buy anything other than DVD's.
Funny enough it was Modern Warfare 3 for Xbox (which I didn't even own) then directly after that I'd ordered it for PS3 lmao. I don't remember fucking that order up.
First games online I bought were from Future Shop or Best Buy. Looks like I didn't buy any games from Amazon till 2014. Looking at the invoice, it was a buy 2 get 1 free deal.
I know exactly which game was my first from Amazon and it was during the time they were mostly known as a bookselling company and I had to mail them a check for Resident Evil 1 (new). Amazon was the only one who had it lol. I can't show a receipt for it since I don't remember having to create an account.
Come to think of it, I don't think it was a check. I had saved up pocket money that I would get and I sent that via mail by putting the cash inside of the envelope.