So this came from the board game "Sheriff Nottingham," in which the goal is to try to smuggle/bribe your way past the player who more-or-less is playing as customs. Illegal goods are worth more, and you can literally offer whatever you want to try to convince the sheriff to let you pass without a search (of course, the game doesn't force players to follow through on anything past using the in-game currency, which are also points).
So what did I do? I said that if Lost would let me pass, I would get a commission of his and my character! And thus this image was made. I'm sure he thought I'd get something more adult themed, but I think this fits the situation a bit more!
Link
Sakke
There is something of an implication either way, so I wouldn't call this an entirely non-adult commission either. Heheh.