There are too many stories to relate them all. I clearly recall finding and buying my first bootleg LP in a little underground hippie shop (E.M.I. Out-Takes). That started a regular weekly visit to the shop for more on my meager teenage budget, flipping through record racks as the owner's dog snuffled at my legs. It wasn't a great bootleg, but it had enough new stuff to get me hooked. The book All Together Now was my bible.
I picked up a bunch of LPs and 45s over the next few years, getting used to hearing a lot of the same stuff recycled and repackaged by different suppliers, with the occasional amazing track (Soldier of Love was also one of my faves).
Then I heard about some CD boots that had just come out and were supposed to be amazing. I hunted and finally found a couple (BackTrack and Ultra Rare Trax). I didn't have a CD player yet, so I had to listen to them at work. They were incredible, and a true revelation. My favorite memory is from working on a movie around that time. The show had rented a couple of expensive cars for the shoot. One was an Avanti, and a co-worker and I needed to drive it to the location. It was one of the few cars at that time to have a CD player installed. The only CDs I had were these two bootleg discs, so we drove through Los Angeles with unreleased Beatles music flowing from the car. It was magic.