My family did not have any restrictions on M rated games or R rated movies like so many other families apparently had. I was playing M rated games and watching R rated movies for as long as I can remember. That being said, if we go by earliest release date, then it would be Doom (PC) or Mortal Kombat (SNES), though like trunkswd said, these were technically released before the ESRB and were only retroactively given an M rating.
For a game that released after the ESRB was established and was given an M rating upon release (going off of a Resetera forum post because a cursory google search did not bring up any kind of official list) then the first game I can remember my family owning with an M rating would be Resident Evil for the Playstation, released in March 1996.
For an M rated game that I specifically requested and got for myself, and wasn't just an older sibling or family purchase, I think it may have been Legacy of Kain: Defiance, released in November 2003. This seems way late to me as I would have been 14 at the time and I feel like I must be missing some other M rated game(s) that I would have asked for before this, but none that I can specifically recall. It's difficult because I did have older siblings that would also get a lot of games, so most of the M rated games we had back then were probably requested by them (and getting an M rated game would not have been all that special to me, so it doesn't stick out in my memory).
I hope somebody can make a comprehensive list of M rated games that can be sorted by release date (and date ESRB rating was granted) so I can perform a better search, because I'm kinda curious.
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