Probably the strangest punt I've ever had was with a favourite indie out-caller in Prague, a 30-something Ukrainian. We'd already met for bookings quite a few times at apartments I had rented, and we seemed to get on really well. I had also taken a tram trip over to her place once, to return the cheer-leader outfit that she'd left behind. We did end up in bed on that occasion - and she didn't seem to be bothered about asking for paying, in the end I brought the subject up.
Not sure if it was the very next time we met, but, at a later booking anyway, we'd arranged to spend a long lazy afternoon and she turned up with a takeaway thai lunch, and thai beer. She refused money for the takeaway, which we put away for later. She changed into a sexy black cat suit, gave me a fairly dominant seeing to, before we settled down to some lunch and a friendly catch up.
When she left she refused payment, saying "that's just two friends having lunch".
I've met her twice since, both times just socially, and although I've tried to book her professionally, there's always been some problem. So I'm guessing we were getting too close for her comfort and that was a goodbye.