Msfs95, first sim I bought with my first PC 
My first flight simulator was FS2002. I bought it on a whim because I had a Microsoft Sidewinder joystick for my PC and wanted something to use it with - the rest is history haha!
Hi,
My first sim was Microsoft Flightsimulator 95.
My first msfs was fs98
My brother had an IBM clone with one 5-1/2" drive ā no HDD. All programs incl the OS were on disk. I donāt actually know the version of the first Flightsim but it looked like the FS2.0 pics except it was all black and white I think. At one point I think I remember he got another version that had the Sopwith Camel dogfighting area.
First flight on FS98: taking off from Meigs and flying on a straight line, landing on that flat texture called ground some miles aheadā¦
Everytime I see a picture from FS98, I can remember that exact feeling of having a pixelated C182 or 737-400 taking off from Meigs with that gray-purple skiesā¦
First flight was Flight Simulator 4.0 on MS Dos
my god, this is all so old 
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SubLogicās Flight Simulator on an Apple ][. Essentially quit flight simulation after FSX because it was always like watching TV. Came back when VR came available. Totally changed what flight simulation was for me.
I started with the 1984 version
Look at it :
Measure the distance traveledā¦
This was mine too. Ah the Commodore 64 and sub logic FSII. How far we have come.
FS2 on the Atari ST for me. I even used it to learn cloud flying when I was taking my PPL to the point that my instructor said that he couldnāt understand why I could fly better when I could not see outside than when I could. Iāve had most of the ms flightsims since with the exception of FS2000 I think.
Apache 64 on a commodore 64, Iāve also flown MSFS 3.1 on a 8080 processor @ 8 MHz, was like flying white lines on a black screen with keyboard only. Since then Iāve owned and flown all of the MSFS series simulators except 2020 which MS only gives me content only.