Catching Up, Mistresses: Three Strikes and Yer Out!

As the reader may recall, I spent some time trying out mistresses. I analyzed costs and talked about a few experiences last year. I rounded out the mistress experiments toward the end of last year, and then gave it all up.

Why? Well, here's how it went:

STRIKE ONE

I had an interview process for mistresses which had led me to the few I tried last year. I continued the tail end of this interview process into last fall. Scheduling issues drove the last three meetings.

Rachel was an elegant mistress who was already a sex worker on the east coast. She was extremely intelligent, well read, intensely curious, and could write fantastic and thought provoking email. Sometimes I would get very turned on from her emails, despite virtually no sexual content. We met once, wholly non-sexually, but the excitement was definitely there. Unfortunately schedules were too difficult and we never made another connection. It also started to become obvious to both of us that the mistress concept wouldn't really work out -- it was too confining for her, and too episodic for me.

Around that time Rachel had an amazing opportunity to follow her dream (and it's a noble one), and she wisely chose to take it.

Ah, we never even had sex, but, boy, the foreplay was great...

STRIKE TWO

Raisa was a civilian, not at all related to the sex industry, in New York. She was an extremely drop-dead attractive Asian woman, born and raised in the US, college educated, and working in the real estate business. We had talked extensively on the phone, where she was the right mixture of flirtatious and charming. She was good on email. We had a rough patch when we kept missing connections, but eventually we hooked up in person. She wasn't as intellectually powerful as Rachel, but she was bright, fun, and witty. Sexually she was not as skilled as T, another mistress from the past, and certainly not as skilled as May or several other ladies from Asia, but she was energetic and fun. She was also younger than T, at a mere 23 years of age.

Alas, after a few dates over a few months, Raisa found the love of her life. After some consultation with me, we agreed this was not compatible wth the mistress system, so I wished her the best of luck, and away she went, moving to Texas in the process.

STRIKE THREE

Francisca was a southern California girl who worked as a print model in London, California and Chicago. There is a reasonable chance you've seen her in a magazine. She has been on second-rate covers and many advertisements. Gorgeous, but having hit 30, and seeing the handwriting on the wall with regards to her modelling career, she was willing to consider alternatives. I'm sure at 21 she would not have given me the time of day.

Again we spent some time talking by phone and email beforehand. She was more erudite than expected, and, did I say a knockout in the looks department? Yep. But to make a long story short, although I had invested the time in meetings and elaborate discussions on mistress terms, it did not work out. On a three day trip I found that she was a very hard partier, and she turned out to be just too crazy. She was all over me for sex, but there was no way I was going to complicate the situation after I saw the copious amounts of substances she seemed to like. Been there, done that. No more. So I held out for three days (not easy, I'm telling ya), and we parted, slightly unamicably.

How do they say it in baseball?

YER OUT!

The mistress situation seems to have just the wrong amount of commitment. It has the contractual upside that I like (and have written extensively about), and it is less transactional than traditional providers, which I also like. But I never got it off the ground from an emotional side. I think you can't set up a mistress situation upfront. In order to make the long term commitment that makes the whole thing make sense, you have to know each other too well. And the shorter term commitments it takes to get there (say, at six month lengths) were too difficult to make given my travel schedule.

So I write off the mistress case for now. But stay tuned, it kind of comes back...