I bought FS 5.1 in 1995 in a bundle with Microsoft Space Simulator. I bought it for Space Simulator and was disappointed in it, but hooked on Flight Simulator.
A couple weeks ago I used a few pictures from that version and it really hit home how far we have come in 27 years.
I know I flew MSFS1 and quite a lot of 2. I don’t recall if I ever flew an earlier Sublogic version. I doubt it but it is possible.
I didn’t own a version until MSFS 5.0 or 5.1.
Since FS2004,
I am really excited to see how far MSFS2020 can go. After a slow start it is really turning into a beautiful simulator.
This was my first flight simulator… Aviator by Olivetti… 1987
Born in 1955 and started with software running in Commodore 64 and regularly improved and updated to nowadays.
Sooo… a youngster then! Welcome to the club 
I began flight simming on an Apple II using BAO Sublogics flight simulator
Aviator on the BBC Micro, that’s the one! I couldn’t remember what it was called, thanks for posting.
MSFS2020 is the first one I’m trying to really sim in though. I’ve literally waited 35 years for something that looks realistic enough to want to make serious use of.
Since way back 15 months ago.
Timex-Sinclair 1000 - it would overheat and shut down before you did much.
FSII on Commodore 64 in 1985
Private Pilot in 1992
FS95, FS98 (Kids come along take the money, then the computer…)
FSX on Steam in 2017
MSFS on launch day with a computer built by my son and I with parts he bought for me for Christmas 2019.
Somewhere on the forum I posted a similar thread several months ago in which I added pictures of the software packaging of all my previous flight sims. My first was played on an Apple iic, Sublogic Flight Simulator. Every version since. I started in 1987 I think.
FS 5.1 1995, but Falcon Gold sometime before…
I first started flight simming on the Sinclair ZX Spectrum and have tried pretty much every simulator since. It’s incredible to see how far gaming has come in general
Since 1989, on a C-64 (born’76 , was a good year 
)
I remember my very first flightsim FS5.1 back just after it came out. I then had every version after that.
About July 1968 at Fort Rucker, Alabama. U.S. Army Aviation School.
I’m a relative latecomer. Saw FSX on a bargain bin around 2010 and decided to check it out, been hooked ever since.
first sim I “played” was fs98 when I was like 10 years old my brother who was always into aviation introduced me to flying a plane with the keyboard lol. but I never had a good enough pc for serious flight simming. first sim I bought myself was fs2004 and what can we say, its still legendary. I remember getting fsx for christmas 2006, installing it, and my laptop noping the **** out lol. when I was at my first job at 18 years old, I got myself a gaming laptop and started “playing” fsx again, but not seriously. I got some saitek panels and had the fun of my life. unfortunately that didnt last long, as my parents flat in that I lived that time caught fire and all my equip was gone 
the day I heard of msfs (2020) I swore to myself I´ll save for a gaming pc. well now after 18 months with msfs a childhood dream has come true as Im building my own homecockpit. and its a blast lol.
Looking at this site:
https://fshistory.simflight.com/fsh/timeline.htm
I’d say it must have been FS 4.0 for me, so somewhere around 1990 - 32 years ago.
Scince FS5 