I don't specifically remember my first flight, but my first flights (multiple) all were with the sim version that came before MSFS98. A wireframe "scenery" of the Chicago area, always taking off from Meigs field and crashing into the high rise buildings off to the left. With my knowledge today, I know why that happened and what to do to prevent that, but at the time I was just pressing buttons to see what reaction I would get out of the default C172.
By the time FS98 came out, I had a basic grasp of what the concept of flying was all about, and then things really "took off", so to say.
I even had a copy of FS98 installed at work so I could practice during lunch time (and slightly beyond

).
I joined EHM on 12/12/2008 with a flight from EHAM to EHGG in the Sukhoi 80. I flew that plane for quite some flights, because I got used to it rather quickly.
My favourite plane ever in the fleet is probably the Beechcraft 1900D, especially in the Croisière Noire livery. Easy to handle, good range and speed, versatile, even usable on unpaved strips... awesome!