The Golden Rule for Mistresses: Keep It Casual


My first sexual relationship was an affair, and I was the mistress. Perhaps I developed a taste for it, or it’s just the blueprint that I started out with, but for me, one of the most appealing aspects of an affair is its casual nature. The subtext is not to fall in love or become too attached. This is a difficult balance to strike, and the long-term challenge is to somehow maintain this degree of casualness.

I was young when a beautiful girl, newly arrived from Japan, approached me. She is a DJ who went on to become very successful in Los Angeles, and I still feel a jolt of excitement when her name comes up in my newsfeed, or she sends me an email. It’s been ten years since she was my lover and I her mistress, and we’re still friends. The secrecy and the heartache we shared have long given way to thrilling memories.

Our clandestine meetings took place late at night. I rode a taxi all the way to her house, and we spent hours kissing and talking and listening to music she was mixing. Her talent was apparent even then, and it’s one of the reasons I was instantly drawn to her. And the way she pursued me so aggressively is what reeled me in. Then there was the sex: the way she arranged toys throughout the bedroom; the way there was always gay porn playing as soon as we both confessed our addictions to it; the way she instructed me to touch her there, and there, faster, and over and over again; the way she coaxed my sexuality right out of me.

I knew the DJ’s partner would likely never find out about us, and years later — as far as I know — she has no idea. We’re all still friends in the way that people who now live in different corners of the universe, but share youthful memories, often seem to be. My lover’s partner never got hurt because she never found out about our affair. This is a delicate issue, I know. Her relationship with the DJ never dissolved as a result of this affair, and the dishonesty is something she was never privy to. Only my lover and I had to live with the deception; we kept the affair to ourselves, and we did so carefully.

If an affair goes on for an extended period of time, some terms may need to be negotiated. For instance, if the mistress begins a new relationship, or the lover needs to cool things for a while. This is where the DJ and I went wrong: I became too attached and she detected it, and we were too young to know how to discuss this. She ended things abruptly, at which point I confessed I was in love with her, at which point she surely sighed with relief that she had gotten out when she did.

When the desire for a different kind of commitment outweighs the desire for the casual freedom of an affair, well, you find yourself with an entirely different beast on your hands. It seems that like a non-monogamous partnership, there can exist a level of trust and intimacy between the mistress and her lover if the terms are established. I’m not likening affairs to non-monogamy; I appreciate how much trust and work go into the latter, while these can be pleasantly avoided in the former. The similarity is just that, like open partnerships, affairs require a particular kind of communication and negotiation not covered in the script of typical relationships.

Here’s the wisdom I can offer to mistresses out there: do not get too attached. I can’t tell you how to gauge the exact point at which the intimacy in an affair becomes too intense to manage. At some point, though, the relationship runs the risk of no longer being casual and free. One of the parties might stop feeling casual about the affair. Emotions might run too deep. Demands might be placed on the lover or the mistress. Expectations might come up, as much for the lover as for the mistress, but typically the mistress suffers through this sort of permutation more brutally than the other party.

What I’m talking about here is the importance of self-preservation, as well as the preservation of the illicit quality that defines an affair when it begins. Dear mistresses, here is the golden rule: keep it casual. If you need to re-imagine new ways to keep your affair casual as the intimacy deepens, and if you want to keep this thing going, talk about it with your lover. Find ways to keep things adequately unattached. Stay free. Some might argue that it’s the lover who holds all the power, and while there is some truth to this, a mistress possesses the unique ability to stay free. So don’t give that up. Your freedom is yours and yours to keep if you want the affair to continue. And in order to keep going, your affair needs to hearken back, as often as possible, to the early stages when it was casual and free.

Repeat after me, ladies: casual and free.

This piece originally appeared on HuffPost Divorce. Republished with permission. Follow Whiskey Tortoise on Twitter:

Image via signature photos/Shutterstock.

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