F-15 strike eagle II on a friends computer in 1991, then when finally my family got a home PC I got microprose's Dogfight as first flight SIM (though first game ever actually was wing commander 2).
then in quick succession:
Tornado
Strike commander
Falcon 3
operation overlord
evasive action
Jane's USAF
F-22 TAW
Falcon 4
Finally Lock on modern air combat and its expansions ever since. :D
Missed many classics primarily due to lack of funds and time.