Years ago, I got a shirt from Greenguy that had his warning page on the back. After dinner with my then wife's friends, one of them asked where did I get the shirt. I told him I was friends with Greenie and he gave it to me at a convention. He then went off on where he goes, Tommy's Bookmarks, I told him, I know Tommy well, Persian Kitty, I used to chat with her back in the Sextracker IRC days, and the list goes on. True to form of everyone who found out back then what I did for a living, I got asked, "Can you get me passwords to this paysite?"
One of the funnier times in the past was when I walked my dog forgetting I was wearing Busty Amateur's shirt I got at a convention that said, "I Love Porn". The faces of my HO president as she drove by me while I waved at her oblivious to what I was wearing.