I know a couple of guys like the musician. Older, divorced or widowed—not really interested in having a relationship. They’re good people and have they’re reasons for going for hookers and not regular relationships. I think they are afraid of domestic and financial entanglements. The domestic takes an emotional toll and they might not have it in them for that anymore, and the financial can ruin you for a long, long time. They also get what they want when they want it from whom they want it from; no dancing around, no entanglements. CIark Gable was once asked why he paid for hookers when he could have any woman he wanted and he said, “I don’t pay them to screw me, I pay them to go away.”
Ask any concierge down here or in South Beach, Miami and they’ll tell you that there has been a growing tourist market in the past twenty years for gigolos as well, although women tend to be more discreet. The term “rentboy” is no longer exclusive to homosexual relationships. I imagine their reasons are along the same lines as the men above. They can shop for exactly what they want, pretty much guaranteed to get it from a very charming pro, then pay them to go away. No entanglements.
Personally, I need to know that the woman really wants to be with me. That’s the foreplay before the foreplay. And I enjoy charming them. That leaves me open to a lot of things, but I can’t be any other way. I think the artist you describe in your details is like this. He might be paying to simply have a nice evening with a beautiful woman he may not be able to attract anymore. Nothing else, no physical intimacy, because she’s basically a paid actress in bed. And the hookers probably love the guy.