This is interesting, I am in a situation similar to this although not exactly. I have been seeing this woman for about 1 year now, after a while of interacting her through a conventional booking number and ad she reached out to me and provided me with an alternate set of contact details which are of "her real world". since then we have been discussing a number of things about ourselves and our lives, she has requested that she wants help transitioning into other kinds of work, a field which I had mentioned I have expertise in. We still see each regularly as usual but recently it came to the point we spent time together but without me paying, she has also stated that she "wasn't working today" To be honest I am not overly investing myself into this situation and continue to play it cautious. I don't normally believe its logical to dive into anything whether it be a transactional relationship or a non-transactional conventional relationship. the biggest thing I can learn is that life is Grey and uncertain and it always bodes well to treat things with caution before there are Clear as day signals to dive into anything.