I didn't become that internet-savvy until after we had the Win95 computer for a couple years. On the Mac, I mostly perused an FTP directory I had bookmarked that had lots of freeware/shareware games.Do you remember an old peer 2 peer program for the Mac? Can't quite remember the name. Something Hat I think. You could host a file server on your machine or load up someone else's with their client software. Has chat room functionality as well. It was the first time I recall running into "go to this site, click this link and this spot is the password to download" messages.
I learned about P2P filesharing in my early teens after I bought my first computer with my childhood savings. I'll always remember the time I was looking up McLaren F1 videos and stumbled into a clip of a British guy with a peculiar manner of speaking.