Earliest was a shemale VHS. I don't recall the name but the first person on screen was a tranny Barbie Woods laying on a bed talking to the camera. I didn't jerk off though, too young for that.
It wasn't until we got our first internet connection that my friend told me about a site called dirtybird.com, which was a tgp site so there was a lot of brand new things for me to experience. I gravitated to the big tits page and fell in love with Aria Giovanni.