In the mid-90s I was just starting to explore my bi-side. I arranged to meet a guy around my age at his place in a seamier, transient side of town near the Naval base - these were the days of dial-up internet, hook up bulletin board sites, and cheap local mags with hookup ads in the back. I dropped in, we got naked, started to play, taking turns sucking face and dick when all of a sudden he flips me on my back, throws my legs over his shoulders, and starts teasing my hole. I hadn't expected or prepared for anal, but the vibe was right and my juices were flowing. He lubed up with spit and away we went. He knew I had no experience with anal, took his time and broke me in easy until he was all the way in and jacking my cock. I've been with thousands of guys since, but he's the one I remember best. Completely anonymous, never saw him again.