I remember using an old Packard Bell shell over DOS. I can't remember what it was called, but it simulated a "house" as the computer. It had an 'office' room for things like Spreadsheets, Word Processing, Finance, etc. That room could be 'locked' by a password. It had a media room, I think, and some other ones that I just can't remember. It also had a kids room with different themes and lots of games. It ran on top of DOS, but we had it dual booted with like Windows 2.0 or 3.1, or something. This was on like a 60mhz Pentium.
Then we upgraded to Windows 95 when we got a new computer. This was in late 1995 or early 1996, if I can remember correctly. I don't remember much about using it though. I do remember when we got AOL and started using the internet.
In 1998 we upgraded to a 466Mhz Celeron running Windows 98 with 64MB of RAM. I still remember upgrading that system in like 2001: we bought a 256mb stick of PC100 SDRAM from Crucial.com for like $40. It made Age of Empires II run so much faster.
In December 2003 I finally upgraded again to an Athlon XP 2000+ with 1GB of RAM and Windows XP. And then came DSL in 2004, and I started playing BF1942 online... and the rest is history.