So, one of my buddies and I stumbled home from the bar last night and I started playing some blackjack for btc. My buddy wanted in, so I sold him .5btc at tradehill's last trade price. He made off like a bandit and quintupled his money. I offered to generate a wallet for him and send it with him on a flash drive so he could keep his bitcoin and stay in the game, but he wanted to cash out in the green ticket, so I traded him an eighth for the bitcoin back.
Bam. Two real world bitcoin transactions in one night. Unfortunately, both of them would be illegal upon close scrutiny...but still...used some bitcoin in meatspace. I am happy.