I also feel badly to take his money but I should explain I saw him many times and undercharged him because he was a regular and we didn't have actual sex (but i charged way way lower than my hourly rate cause he asked me to...mistake number one) but even after me doing this, he still wanted more (not nesc. a cheaper session, but more from me i.e emails after the session, never giving me notice for meetings, always asking at the end of the session "so how much do i owe you?" which made me feel really awkward etc etc) so I think, well I've given him a lot more than he's given me really so why not?
The bright side of this situation is that this guy has been an absolute poster-child for what to AVOID AT ALL COSTS from any client. If you wrote out a big, bullet-pointed list of his behaviours, as outlined by yourself above, and pinned it up on your wall somewhere, you could check it regularly and make sure to NEVER EVER see anyone who does ANY of those things, and then you'd be safe from 90% of the unpleasant types straight away!
It's a tough lesson to learn in life - that there are people out there who will treat you like an idiot, and will take everything they can from you without even a split-second's doubt or empathy about what they're doing - when you're a decent human being yourself, but it's important to learn quickly. These mini-psychopaths, as I think of them, are sadly common and are usually really good at toying with emotions (i.e. this guy, trying to make you feel like you owe him something because of his "feelings" for you, when I would actually bet ?10,000 right now that he's never had a genuine feeling in his life
apart from self-pity because he can't get enough attention from ladies without playing these sorts of absurd games with prostitutes) so please don't feel like you need to feel sorry for him even one second longer. He's having a right jolly old game with you.
There is no limit to the effort he will put into his boundary-pushing with you so I wouldn't ever see him again. Cut off contact. There is no easy ?500 for you in this - you cannot cut him off if he feels like you owe him, so if you take his ?500 then you are basically entering into an 'agreement' that he can harass you for even longer. He will be delighted to know that he can make you perform according to his wishes so easily.
Cutting people off is easy and you need to learn it VERY EARLY ON in the process of becoming a happy, sane, successful prossie, because the alternative is becoming a victim to every pathetic saddo like this guy (and the hundreds of others) who get off on using people.
I think I have to treat this more like a business and not worry about hurting feelings of clients old and new.
Please do. I'm not sure how old you are but these guys, from what you've mentioned, are older than you and they are therefore a LOT wiser and craftier than you think they are. Every escort who's been working a year will have 100 tales of boundary-pushing guys and they always start, "I didn't realise at first that he was that kind of guy..." because these kinds of guys get really good at disguising themselves as normal/sensitive/whatever. But they're just manipulative creeps. Eventually you learn to recognise the signs very quickly and you learn to set the Smart Prossie Rules (full fee, in proper, checked British bank notes, up front and counted right there and then before any services or even a shower are offered, etc).
I'm saying this as someone who's had her own fair share of surprising/horrifying incidents of, "Why would anyone put
so much effort into trying to push me into doing things I don't want to do when they could just go elsewhere and get what they're looking for?!?!" so please don't think I'm talking down at all. It's very confusing to us straight-forward, generally-pleasant kinds of folk. But trust me - there are too many boundary-pushers out there with nasty, selfish attitudes and they are ALWAYS really good at hiding it. You do always think it's your fault the first few times, but it actually isn't at all. You just have to learn quickly to be on your guard with EVERYONE you meet, especially the men who contact you via your escort ads because they (the bad ones) think of prossies as very easy targets. Try not to prove them right. ((hugs)) Learn from this experience, though, and you'll be sorted from now on.