Boston
So I'm a dude (shocking!) and I have never been "picked up" by a stranger, and I have always wanted to. You know the story.. I'm having a drink in the hotel bar (or whatever) and you were to come strike up a conversation about how my face makes me look ugly but everyone else in the room sounds like a douche.. we have a couple minutes of cute chatter at which point you ask me how to use the remote control in your room. Think a simple "Dear Penthouse" letter. 
In fact I've done something similar before. You would need good references and you would still need to have your envelope ready when the lady arrives at the bar to slip her discreetly. And make sure you book enough time to allow for your bar flirtation and your fun behind closed doors upstairs. 
I'd be happy to indulge you if you think we would be a good match (visiting tonight until Tuesday morning). I bet there are lots of ladies who would be totally into this if you just ask ladies who are specifically your type, though.
