To the OP: you've just joined and come to the right place. You'll get the hard truth here, especially from punters who have been round the block more than once, done the trust thing, fallen on their face, and picked themself up again.
You maybe have a touch of what we call EAS syndrome as well. A bit like a virus. The lads here will help you get back into the punting hobby faststream but you won't get away with "not going into details" for very long. The first thing that shows you're on the road to freedom in this game and being honest with yourself is exactly that: admitting the details, who, how long and how much. Post them (and make sure you don't let your identity out). Do that and the truth sinks in that you are paying a prostitute, not seeing some version of friend-with-benefits. It's all fine and dandy -- as long as you cover yourself from being milked or scammed.
Prostitutes can be sweet and smiley. It's part of their job. Keep the customer happy and paying more (and
their idea of paying, not yours). btw, promises for freebies to 'pay back' what's owed rarely if ever amount to more than squat. She will expect you to be 'gentlemanly' and forget about it. At best try to get an extra bit that's 'owed' at the end of a paid booking but much easier to move on
now before she decides your cash dispensing is not to her liking and moves
you on.