I go a bit further back than the original Windows. My first Windows was Windows/286, but I didn't use it for drawing because the paint program included was monochrome, and the 1MB of memory on that old 286 couldn't handle even a rudimentary Windows. I mainly used DOS programs for drawing until Windows '95 (though I did dabble with the Paint program in Windows 3.1 too).
My first digital "drawing" experience would have been using a program called "Logo" on a Texas Instruments TI99-4a in 1982. I was in grade four and the school bought a bunch of those computers. It had no mouse and used a TV set for a monitor and a cassette deck for storage. Drawing was done by entering commands to tell the "pen" called the "turtle" what to do - you'd tell it to move ahead so many pixels, then rotate a certain number of degrees, then ahead again, you could give it commands to lift off the "paper", etc. You could also create moving sprites, but they were monochrome and could not interact with each other as they would in a game.
The first computer I ever owned would have been in the late 1980's, a Fujitech Jumbo 8086 6MHz IBM-compatible, with 640kb of RAM, a 10MB hard disk, two floppies, and an amber monochrome monitor. The name "jumbo" was apt - it was the size of a large microwave oven. No mouse, no sound card, no modem, running MS DOS 3.3a, it was basically just a fancy typewriter, which is pretty much what I used it for. I used a word processor called "Professional Write" back then. I didn't draw at all on that, because with no mouse and no colour I didn't see the point.
