This a helluva old thread. I can't remember if I've contributed to it before.
1. It's a common newbie or fluffy or whiteknight fantasy, 300% misguided.
2. The rare times it has happened has not been with some regular that I then formed a 'relationship' with: it has been with women who escorted for a period and with whom I would not want punt. On one occasion it was for about two years with a woman of high intelligence who not only accompanied me to international meetings but accounted herself brilliantly in all situations, talking with my friends, colleagues and even including professors, and was always admired. She paid her own way on everything we did. She didn't live off me and I didn't live off her. She escorted through an agency, accepting two or three bookings a week to pay for books, artworks and other sophisticated tastes. It was mutually advantageous, as should be any relationship. I learnt from her (particularly Arts) and she learnt from different aspects of my life. Our working hours meant we both could spend time enjoying fabulous but fairly normal nightlife together. We separated amicably when conflicting interests meant she had to live abroad. On another occasion I had dated a lifelong friend who much later escorted for a few months so I wasn't actually dating a WG. I mention it as she invited me along one time to demonstrate the 'escorting experience' which she basically treated as a roleplay within which she worked. It was quite hilarious, especially when she switched back and forth in and out if character! I've also had one or two short, amicable relationships with women who happened to escort (no money ever changing hands and no 'in kind' payments) and with whom I would not have punted. Punting and dating are radically different things.
3. My conclusion of all this, and many years of punting, is that there is no such thing as 'dating a WG'. She is one character or the other. You can't do both. If you think you can then you are fooling yourself. If you entertain it as a hope while punting with her you are the biggest type of idiot.