Windows 98. Later the first Linux distro I tried was Mandrake Linux but I didn't really get into it until later with Crunchbang.
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I had a Debian PC for a while, it was more of a project. IT work still revolved around Windows back then. Later I discovered Puppy Linux and ran that on a live USB. I encrypted the hard drive in my work laptop and never had to worry about anything making from the USB to my work data. Not a bad way to live, only had to carry around one laptop when I traveled for work.
My first OS was Windows 98.
Linux distro was Ubuntu 6.0.
First OS: MS-DOS 5
First Linux (many years later): Yellow Dog on one of those dome-shaped iMacs with the PPC chips
Red Hat 7
mint->chromeOs->kali->windows->arch->openbsd->arch->nix