My first ever OS was a windows 95.
I remember my first experience with programming was windows 98 and purebasic. I made a trivia game.
The first computer I got close to was an IBM650 with revolving drum memory, punch card I/O and vacuum tube flip-flops. That was at the University of Western Ontario in 1961.
My own first computer in the 1980s was a Radio Shack MC-10 Micro Color Computer with 4KB RAM (upgraded to 20KB!), cassette tape I/O, Basic in ROM and a serial port. It connected to a TV set and had a 4 baud modem which required flipping a switch manually to connect. I used it to connect to my friend's account on the mainframe at York University.
I also made a game, but not trivia. I used peek and poke commands in the screen buffer to make the screen scroll in reverse and created an arcade-style action game called "Acid Rain". When I started dreaming in loops and branches, I packed it in and decided to come back to computers when they were more user-friendly.
That happened with Win95 and my first dial-up internet connection. Building rigs was fun back then... no plug and play. Lots of jumpers, specifying HDD parameters, etc.
Those were the days.