/Robbing the Playpen

At twenty, I had two lovers. One was 34. The other was sixteen. Both were guitarists; the older one a jazz-fusion player who was my height, possessed these tiny, nimble fingers and was big in Japan; the younger was just discovering The Clash and Buddy Holly and was big in his head. The older one drank blackcurrant tea with half ‘n half and drove a Subaru wagon; the younger drank shots of tequila and drove an orange VW that he called “Herpie, the Hate Bug.” The older I dumped; the younger dumped me.

This study in contrasts turned out to define my dating choices for decades. It’s now 28 years later, and I’ve had one long-term relationship with a guy my own age, and three long-term relationships with men at least a decade younger. I’ve fucked exactly three men older than I—one I dated for about ten weeks. It was awful. He sipped a gorgeous expensive scotch given to me by my previous 27-year-old lover and responded, “Oh, strongy-strong.” I wanted to kill him.

I’ve always been mystified by my friends’ attraction to older men. In college, my BFF held a consuming passion for her music professor, a man who came with the full complement of middle-aged accoutrements: a wife, children, a balding and slightly scrofulous pate, a belly round as a pumpkin. It was incomprehensible to me, as was her reluctant acceptance of the amours of a hot, smart Ultimate Frisbee player with dancing dimples and a hard dick. I never got the older man thing. But then I’d never been much attracted to money, power, education or experience. (Only this last has changed; I now value experience very much. But I’ll return to this.)

I should, however, note that as much as I hold strong antipathy to the older man, I’ve no issue with men my own age. I like them. They’re swell. These days, middle-aged myself, I can look at a middle-aged dude and see the fragile beauty in eye wrinkles and feel tender toward slackening flesh. I like sharing a common cultural reference point. I can give up the high-and-tight greyhound testicles for some hard-won experience and the vulnerability of a healed heart. However, as much as I like middle-aged men, they tend not to be available. It’s essentially an unrequited interest.

But my preference for a man is younger. He used to be a standard eight-to-ten years younger (and, indeed, this is the age bracket I like for a relationship), but now he’s a lot younger than that. He is, if you look at my last ten years of sex history, anywhere between a seemly ten years to a rather staggering twenty. I admit it: I quake when I could have gone to high school with my lover’s mom. It makes me feel weird and, well, really old. Age is not just a number. Size matters. And you’re not only as old as the person you’re fucking.

But fuck them I do. Most recently, it was this creamy dish of an Eastern European of uncertain descent. He possessed a mind of dark beauty and a cock as long, straight and narrow as a ruler. So long and so straight was the cock of this polyglot that my throat closed abruptly. Not all the porn-starry spit in the world would make it glide easily down my throat. Aboard his disconcertingly maritime-looking hotel bed, he gave me small blackberry bruises all over my inner thighs with his bites. He was a lot of fun, and I left that room with a serious case of the tristesse. I’m not sure if I was smitten more by his biting teeth or sharp cynicism. Most likely, it was the deadly combination of the two.

Before him was the 27 year old, a skinny black geek with graphic novel tattoos, a generous mouth, a splendid cock and the atavistic need to be dominated. We spent a few days in various beds painstakingly learning how to please one another. It turned out that I liked riding his mouth. He liked me to insert toys into his ass and then fuck him stupid. I feel the great blush of accomplishment in knowing that I made multiple fantasies real for this man, whispering in his ear as I worked some giant hunk of metal into his reluctant anus.  It worked for me until it didn’t, and now we’re very good friends.

Before him I have to go back two or so years (I actually don’t have a lot of casual sex). He was an utterly forgettable 23 year-old redhead. Mistakes, I’ve fucked a