I tried to recall the first but it’s fuzzy, I do recall specific early events but it’s based more on other events.
‘82 came home with a 45 of AC/DC let’s get it up and J Geils Centerfold. I was 10, I played violin and acoustic guitar and a friend and I each played one as an “air guitar” and jumped up and down on my bed. My mom came in with a WTF look
‘85 I was 13 and my oldest brother was living in Houston and just had my first nephew. I got to fly down out of Pittsburgh by myself and I remember rocking Ozzy Bark at the Moon and Van Halen 1984 on my Walkman during the flight.
‘89 I got my first CD player for Christmas ,the same oldest brother bought me Steely Dan Can’t Buy a Thrill. So clean, no hiss, no cracks, no pops, love at first listen.
2005 my wife won a fancy IPod classic at my work Christmas Party. I joined iTunes and learned how to rip my library. AC/DC Highway to Hell was my first rip and it sounded exactly like the CD when I attempted to sync them and toggle. Been playing with that ever since then, love the ease of use and only really needing one device that I already carry daily (a good cell phone) for a source for my whole collection which still amazes me.
I also have fond memories of swim team in high school and practicing with my Sports Walkman. I think I was the only kid in school who used theirs in pools.