Oooh! The first fandom I spent actual time doing fandom-y things for was Harry Potter. I was reading fanfic, listening to podcasts, going to midnight release parties for the books and movies... all that fun stuff. I never shipped for Harry Potter, though.

Shipwise, before I even knew what shipping was, I was shipping Tommy/Kim in Power Rangers and Buffy/Angel in Buffy the Vampire Slayer. Baby's first M/M ship was Yusuke/Kurama from Yu Yu Hakusho. I know Kurama/Hiei is a much more popular ship, but I was always drawn to how protective Yusuke was over Kurama, despite the latter being a demon that was hundreds of years old.