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The first game i bought with my own money was Treasure Island Dizzy for the speccy. It was £2.99 at a local independent game shop which i still frequent most weekends.
Haven't a clue what the first game i had bought for me was, i have older brothers and have pretty much always had games around for one system or another. It was probably a 2600 game though :)
I did not buy very many games myself when I fist had an NES-- in fact, I don't remember buying any at all (having no allowance sucked, I hope I never put my own kids through that), but I certainly remember the day that I walked into Funcoland and walked out with Super Star Wars for Super Nintendo. Ah, what a glorious day that was! :D
The first game I ever bought was Smurf for the Colecovision. I must have been in the 4th grade and I mowed about six lawns to purchase it. The only hard part in obtaining it was getting my father to get off his ass to take me Toys R Us.
Choplifter for the Atari 7800.
Sonic & Knuckles Collection and Sonic R for the PC when I was 7
Jet Moto for PS1.