It's not happened much but I always find it weird if a WG suggests me staying after the booked session e.g. if they've no other bookings. The topics of conversation are usually pretty mundane e.g. working conditions, dislike of aspects of UK life etc.
Usually true but there are exceptions. One girl I see occasionally we hit it off from the first meet, when I book her for an hour I'm usually there at least another couple by the time we've stopped talking. The only trouble is I once booked her for an all nighter - not something I'd do with any other WG. Obviously we had a good time, but I don't think there was any more action than I'd normally get when I book her for an hour; we ended up just talking and having a laugh for longer.
Back on topic:
I have sort of told one friend. It was semi-tactical though, she's an old fuck buddy who I'd like to have another go on and who's admitted she still likes me too. She's also a bit down on her luck at the moment, so when we were talking ways to help her I hinted that we could probably come to an arrangement where we could have some fun together and I could help her out financially. Said something like I'd rather give her my money instead of paying for it elsewhere.
There was the inevitable "have you actually done that?", to which I replied "hasn't everybody?". The conversation then went more along the lines of whether there was a difference between spending money on flowers, dinner, drinks etc to get what you want or just outright paying for it. I never specifically said I'd punted but I think it was enough for her to get the picture. I also told her how I used to give my ex-girlfriend some money each month to top up her income so she wouldn't just think it was straight up selling herself.
So far it's only got as far as me lending her a bit of money to help out, which she's said she'll pay back but we both know she can't afford to (and we both know it's money I don't really need back). Whether anything else will happen I don't know, I'm not going to come straight out and offer her a deal - I figure it's got to be her idea. I won't be disappointed if it doesn't happen, unlike punting this one is real life so there are other complications to think about, but I hope it becomes a win-win situation for us both.