In the nearly 7 years that I have been an escort, I have told three men that I loved them. In all three cases, I never took another envelope from them.
In one situation shortly after I began escorting, I met someone travelling on business who wound up falling in love with. There was never any expectation that a long term relationship would develop. We didn't even live in the same time zone. His business brought him to my city 3 or 4 times a year, and over a period of about three years, anytime he visited my city, I simply dropped everything and spent a few wonderful days with him, no strings attached. We were friends with benefits.
In another situation I met someone and we clicked immediately. We decided to give a relationship a try. I don't know if its irony or just reality, but in spite of having met me as an escort, he simply could not cope with my job once we decided to get serious. About the time I met him, I had been wondering to myself if escorting had jaded me to the point where I couldn't have a normal relationship. So when I met him and we developed feelings for each other, I welcomed it. I just regret that in the end it didn't work out.
And in the third situation, I told him I loved him, but it is more like a love I would feel for an older brother. He's become a best friend, and to be honest, I just can't see him as a client anymore. I adore him, but ours is now a friendship, and not so much a business relationship.
So yes, it does happen. In all honesty, this is a very personal and intimate business. It is inevitable that emotions will occasionally get involved. I hope I never reach a point where emotional involvement becomes impossible. I think if that happens it will be time for me to retire. The real key, is how two people handle their emotions, and in that respect no two situations are alike. Hobby romances more often than not do not end well, but I know of one happily married couple who began as escort/client, and as far as i know, have now been happily married for a few years now.
But the best advice I can give someone is to manage expectations, go slowly, and communicate. Pretty Woman was indeed a work of fiction