My first flightsim was actually something on the ol' C64 (back in 1988), though I never actually 'flew' the game as the floppy had cracked, and the game was damaged.
After the C64 finally refused to run, I upgraded to something with Microsoft Windows (as late as 1995), and got Flight Simulator 95 from a friend. I remember being very chuffed with myself for flying all the way from North Weald to Heathrow the very first time in the default Cessna, using just a roadmap as a reference. ;p
FS95 made way for the original Combat Flight Simulator, which later made way for FS2000, and after that CFS2. But then I made a small deviation to IL-2, IL-2FB, and IL-2 1946.
Finally, in or around 2005 I got FS9, as it was 'chucked out' of the stores on the arrival of FSX, and I returned to civilian flying. At first I tried the default planes, but soon I decided I rather liked the DC-3. I remember my very first 'around the world' flight came soon after, when I took the DC-3 around the world via the East. Took me quite a few months, too.
At the time, I only sporadically did addons, mostly stuff purchased from the discount bin in computer stores. Mostly stuff like Flight Deck, the C-130, Airbusses, and that kind of stuff. But I never flew much with them, as they weren't my stuff.
And then, one day, I happened to stumble upon a site called 'Calclassic', sometime in 2006. I was actually searching for something quite different (modelling, information on the interior of a DC-3). I still remember the first time downloading the classic traffic - for quite a while, I had the 'double install' (CC traffic with the default one).
Then, September 2007, I did my first venture upon the Calclassic forum, with a query about something. I had little idea about how things were about to snowball.
So now, five-and-a-half years after that first install, and four-and-a-half years after that first query, well...
Let's just say I'm flying a full Calclassic version. I always thought the fighters and bombers would be more exciting (hence the CFS & CFS2, and the IL-2 games), but I've had far more enjoyment just flying the 'boring' airliners. For example, my last two flights were El Al flight 209 (1957) - a Lockheed L-149 Constellation from Tel Aviv to New York via Rome, Paris, London and Gander; and Air France flight 20 (1957) - a Lockheed L-1049G Super Constellation from New York to Tel Aviv via Boston, Paris (with a technical landing at Shannon) and Rome. I've even got the fuel- and weightsheet for the next flight next to me: TWA 925 (1957) - a Lockheed L-749A Constellation, again from Tel Aviv to New York, but this time via Athens, Rome, Geneva, Paris and Shannon...
Not to mention the couple of sceneries I've contributed to. Or the flightplans. Or the SNCASE Armagnac that is slowly taking shape in a lonely hangar...