Rejecting a Mistress

I had a recent experience with a civilian mistress, a woman who was looking for a "patron." She was not a provider in the traditional sense. She claimed to have spent the past few years as the mistress of a wealthy and married-with-children Fortune 100 executive in New York City. She was a "kept woman", that is, exclusive to this man, who in turn provided her with a monthly stipend, gifts, and travel expenses.

Recently his wife became gravely ill, needing care, and so they mutually agreed to terminate the relationship.

At the time I met her, she was seeking a new patron. A fellow hobbyist (who wishes to remain anonymous) had "sampled" her and found the quality to be excellent but the expense to be high, so he referred her to me. I can only imagine that it was my experience with Anne-Marie, the ten thousand dollar escort, that made him think that I'd be interested in an expensive mistress. I have always claimed Anne Marie represented my "young and stupid" days, but still I was curious as to what kind of woman could have been a mistress to a successful business executive who, like me, could have elected to be a hobbyist instead.

With my interest piqued, I spent two months both meeting and communicating with her, a "try before you buy" trial period. That trial period is now over, and last week in Asia I decided to forego the "mistress experience."

If you know me, you know that I keep trying long-term experiences. Rather than one hour meetings, I prefer an event, or even a shared vacation sometimes going as long as a week. My experiences have been mixed, but when I connect with a wonderful provider, I really like to STAY plugged in... (get your mind out of the gutter!) Sometimes it leads to trouble, other times it's great.

So I first met "T" at Jillian's, a pool hall and bar in Seattle, where we talked over drinks.

"T" is an attractive, dark haired, late-20's woman with striking eyes and a lithe body. She was recruited into a gifted children program when young and remains smart and informed. She is very well educated, has real-world work experience in politics and journalism (in Washington, D.C.), and is very presentable and stylish. She exudes class.

I would feel quite comfortable having her at a sit-down dinner with business associates, which is something I could not say about most US providers (or girlfriends) I have met. It's because she's used to it, having spent a lot of time with businessmen and politicians in social settings. She carries an excellent coversation, and has a good mixture of being head strong and accomodating.

T is sexy and smart, with a wicked sense of humor. She can also be comfortable and casual, in jeans and a t-shirt, or lounging in sweats. And T is sufficiently organized and tasteful that she can plan and schedule an outing or vacation herself, which relieves me of those chores.

Best of all, despite being masterfully urbane and polished in public, she is an absolute tiger in private. She is particularly good at creating mind-blowing scenarios with her exceptional intelligence; using her head in more ways than one, so to speak. Probably the only place she falls short of my ideal is that she is not bisexual.

But rather than bore you with details of a set of essentially civilian encounters, let me instead talk about why I elected NOT to do it.

1. A mistress is an odd kind of monogamy. On the positive, She is available 24x7 for you. On the other hand, she's expensive enough that you can't really play the field as much if you have her. Or if you do, you're spending a lot of money. I think the mistress system makes a lot more sense for somebody in the "married with children" situation than for me.

2. T is like a drug: expensive and addictive. Bad combination. She would be a great girlfriend if she hadn't picked up those expensive habits and liked her own freedom so much. She was willing to be my mistress for about half the price of her previous deal, but it was STILL expensive.

3. Worst: the hobbyist-provider boundary isn't there. Or it isn't as clear. Which is pretty damned dangerous. I could easily see losing the detachment needed to stay sane in this business. And, as I have written elsewhere, I can't seem to convert a paid relationship into a healthy girlfriend relationship.

But oddly, I was still on the fence and thinking about signing up for a year. I even had the tax and business structure worked out. I had gone back and forth, and forth and back on it for a few weeks...

Until my experience in Asia.

And that was what tipped the balance.

Who needs a regular provider? I'm just in the wrong country!