Hah! I can relate. I am the oldest of three brothers, and I terrorized my siblings growing up. Funny thing karma... by the time we were teenagers, both my little brothers outgrew me and are much bigger than I am. I remember when I was about 19 my "little" brother picking me up and tossing me across the hood of my old Firebird. Revenge must have been sweet, I assume!
Your bro was a trooper and seemed to be enjoying the whole experience. I thought he was a pretty cool guy. Dimetri is a good name for him, methinks.