dont remember, but I think it was some game. currently I have over 150+ games in steam, origin and uplay combined. my first windows (vista ultimate) was given to me by a friend who being a ms employee felt bad that I was using pirated he also managed to convince me to buy original games if they were good.
These were a few of my firsts -
* A Nightmare On Elm Street
* Chuck Yeagers Air Combat
* Leisure Suit Larry in The Land of the Lounge Lizards
* Secret of Monkeys Island
Never bought any software in my whole life. Maybe the windows 7 that I got by default along with the laptop might be termed as one. But, I didnt want that as well because the first thing I did was installing the ultimate version.
First s/w I bought was win 98 SE (Not Win XP as I thought earlier). After that I slowly converted all the pirated s/w into licensed ones. It took me some time to convert all the pirated s/w. Last one got converted three years back. Currently I don't have a single pirated s/w either in my work machine or home machines. I do use a few open source or FW apps like CCleaner, NPP etc. in my home machines.