Probably not a great idea, I mean, unless you're perfectly comfortable with the person you're dating shagging 3+ people every day.
Ironically a few months ago I considered something similar... I saw a WG in Winchmore Hill, London about 2 months before Xmas. She was really young, 20, a student, English, really hot mixed race girl. She said she only does it every now and then when she has time off from uni. She seemed quite lax about the whole escorting thing and was quite happy to do things lots of WGs either won't do full stop, or won't do unless you pay them £20 extra. I don't mean BB btw, I'd never do that. Anyway she seemed to generally love sex.
We went way over time and she'd said something like 'I don't usually finish my night in that great a fashion' and I thought 'yeah I'm sure you say that to all your last punters of the night'. But then at the end I asked her if she always wants guys to pay her, and she said 'not if I like them, no...'. So I said, well how about next time I give you a call, I don't bring any money with me'. She said that sounded good and gave me her personal phone number. Needless to say I walked out feeling pretty smug and had visions of having just found a great fuck buddy from a punt. I called her a week later and went to see her at an agency house she was staying at, but hadn't made clear that I didn't want to pay her. I got there and said that and she said you need to leave (lol), but I can see you tomorrow afternoon. I left and her pimp, who was a woman who let me in, somehow got my number and text me having a go at me for turning up with no money. I actually saw her the next day and never again, basically because she was really unreliable around meeting up and always seemed to have some kind of problem with where she was staying, or would prioritise money over seeing me (fair enough). I'd considered that we actually apparently got on so well, I could see myself seeing her and hanging out with her etc, if she wasn't working as a WG all the time.
End of the long story... Moral of the story is it probably isn't a good idea. Seems a good idea at the time but it isn't realistic. Also once you've gotten used to getting £100+ for something, you're probably always going to do that over doing it with someone for free. And that will affect how reliable you are, and how trustworthy that person perceives you to be...