My problem is that I tend to fall in love a little with my "providers," sometimes just a crush, sometimes veering towards more. And it’s sometimes mutual—I’ve actually dated two providers I first met as a client. Truly dated, without paying for the sex. I think it goes back to my young marriage. I was quite young, 19 years old, and I married a girl my age who was so completely sexually open that she set an almost impossible bar for the relationships I’ve had since. We divorced when we were both 23, and for a long time the only way I could experience the kind of sexual intensity I had with my former wife was to date much older women, 30 or older. Occasionally I would date someone my age or younger, but invariably I was disappointed. Younger women, and I know this is generalizing, are just not as comfortable in their own skin. Now, at the age of 38, I realize just how lucky I was with my young wife.
Right around the age of 30, I started seeing prostitutes, always in between "real" girlfriends. I use a local Internet review board and do a lot of research before settling on someone new. For the first few years, it was more about sexual variety—women of different ages, races, body types. And they were almost always extremely sexually skilled. It created kind of a vicious circle: when I started my next relationship, I would long for and expect the sexual competence and freedom that prostitutes often provided. Finally, about four years in, I started falling for a provider for the first time. Her working name was Trixie, and I was smitten the moment I laid my eyes on her. She looked like Bettie Page, tall and voluptuous, and we both felt an instant rapport. The sex was completely off the charts from the very first time. I’ve been with many women and can be a little jaded, but she surprised me with every move. From the deepest deep throat of my life to her actually asking for anal (and coming that way), she initially reeled me in with her superior sexual skills. But then, fuck, she turned out to be smart, as in scary smart. She was more than just a dirty talker... she would spin crazy, creative, erotic stories on the fly, while we were fucking, and by the time an hour was up, I felt as though I’d had sex with a dozen goddesses.
I saw Trixie as a paying client for about six months before I finally asked her out. I took her out just a few times, and we had a lot of fun, as well as a lot of really great sex. Unfortunately, I started having true feelings for her. I remember a really sad moment where the impossibility of the situation hit home. We were having Sunday brunch at a cool little neighborhood spot, and it hit me: "Dude, you’re dating a prostitute." I suddenly realized that this was something I just was never going to be able to explain to most people, certainly not my family, although I’ve since told a couple of friends who didn’t think it was that big a deal. Anyway, that was the last time I saw her as a non-client. I stayed away for almost two years and went back as a client just once before she retired. We had a sweet little reunion, and she told me about her plans for going back to school, and getting married, and moving to a small mountain town. She said, "You know, we probably could have made something work." We had amazing sex one last time. About a year later, I got an e-mail invite to a BBQ at her and her new husband’s place. I had a new girlfriend at the time, and I couldn’t figure out a way of explaining my connection to Trixie, so I ignored the invitation. I think of her fondly now, but haven’t tried to make contact.
Since then, I’ve dated one other provider, and a part of me wants very badly to ask out another who I’ve been seeing recently. It’s sad, because the sex is at the level I desire, and, like so many working girls I’ve met, she’s incredibly witty, big-hearted, and intelligent. But there’s no good end. It would break the hearts of so many people in my life if they knew the truth about a relationship that started that way, and I couldn’t live with myself lying about it. I have a suspicion that I will always harbor crushes and strong feelings for providers. There are worse crosses to bear.