Bumping this thread because a semi-regular of mine has asked me out on a non-paid meet, which I suppose in the real world would be a date.
She actually suggested this before - we have met up for off-the-clock drink and a chat before now, and she is good fun. I am of course extremely cynical, but it does seem she genuinely would like to spend some social time with me. I think she might be a bit loney/bored.
I don't see any problem, although it is an odd situation - she realised this would probably lead to sex anyway, and so it's a weird thing to negotiate, since she knows I'm prepared to pay her, so why give it away?
I left the ball in her court, and said if she wanted to meet for a drink or free fuck that was fine, and she could dictate the time and events etc rather than me. If I were to take the initiative, it would be odd - basically asking to book her without having to pay. Bizarrely she seemed sad at this, saying it seemed like I didn't want to meet.
No interest in a relationship with her, but despite my very high level of cynicism, I do think it's possible we simply get on well, and she enjoys chatting, which is fair enough - even WGs are human, so we shall see. I'll probably meet up with her sometime for a drink, and if she wants to fuck afterwards, that's up to her. A very complex scenario, once money has changed hands, I think.