I have had five relationships with ladies of the night over more than 60 years, and I'm not sure to what degree they all qualify.
When I was very young and good looking a girl asked me to live with her - be a ponce or pimp, I guess. I only spent one night with her and decided I would be too cowardly to do the job. I suspect I would have been jealous, too.
The second was many years ago with a very successful girl who had been fitted up by the police and forced to retire. Bizarrely enough she was one of the most jealous women I ever met, but the relationship lasted over two years. I was excited by her past, and amused that one of our clients had been someone famous whom I knew.
The third was far more recent with someone I saw twice who then asked me to come and stay with her for the weekend. She has now retired. We exchange messages every day and she has invited me to come and stay with her when her husband is away (I have met him).
The fourth is quite recent; it was her idea, we remain very good friends and she knew I had no intention of moving in, but the sex got less interesting anyhow.
I am currently seeing someone else who after two meetings suggested I stay with her over the weekend, no charge. As I like her I shall also take her away - again no charge.
I am pretty sure my attitudes have totally changed since I was young, when I think I was naturally jealous. I actually am excited by the idea of someone who sees clients, especially if they are very kinky, which she certainly is.
I don't think of it as getting sex free when I usually pay. In fact I don't mind giving her money, and do without being asked as I see her as a friend. When I think of what my marriages have cost me it seems a smidgeon.