Like a lot of the other people here, most of my "first" maps were on paper.
The oldest alternate-history map I found on my computer was this one of Europe in a ridiculously implausible scenario (which is pretty much all I'm capable of
) involving, ironically enough, a superwanked UK:
And then the first map I uploaded to this website, a fantasy scenario set in the future in which LEGO minifigures become sentinent- but turn out to be evil
I wanted to post the blurb, but the old map thread it was in has been lost to the virtual shredder of time. I remember I described the various regions as being associated with LEGO themes, for example I believe the big square in the middle of Africa was called "Pirates' Island" or something, and Iceland was "Ice Planet 2002". (Bleh, I hate looking at my old posts- they seem so immature)