Lets see. In order.
18 years old - Did a mom and daughter. Not at the same time (about 6 months apart) and they were both good looking.Daughter was 18, mom was 36. That was crazy.
20 -Did 2 girls the same day. I know I was a whore but I was 20. That has happened since then several times but after the first time, not a milestone.
Not interested in doing it again unless at the same time.
36 - A hot 21 year old stripper. Dated her for a while. Fun but too much hassle for me. (rebound fun time after a long relationship ended)
36 - First set of fake boobs.

Ironically enough stripper listed above just got new boobs and text me today.
Thats allthat sticks out right now.