Digital Extremes, 3 on a Tree + Sex Banks - OZY | A Modern Media Company

Digital Extremes, 3 on a Tree + Sex Banks

Digital Extremes, 3 on a Tree + Sex Banks

By Eugene S. Robinson

Two people having sex.


Because good sex starts somewhere. And that somewhere is right HERE.

By Eugene S. Robinson

Accounts Payable

EUGENE, SIR: Let’s call him “Jack,” my boyfriend for the past 11 months, keeps track of how often we have sex. Not only this but the kind of sex we have. On the one hand it’s nice that he’s so focused on sex, but this number crunching is sort of no fun. The sex is fine, the documentation is not. Suggestions? —M.S.

Dear Goal Tended:

Well, on the one hand, this is the kind of guy that if you’re planning on being a long-term married, you probably want on your team, since if you haven’t had sex for 18 months and have forgotten that you haven’t had sex for 18 months, he might be nice to have around to remind you. On the other hand, you probably don’t need anyone around to remind you to brush your teeth after about 18 months. No. The world is wonderfully reliable that way, especially insofar as stank breath is concerned. And long-term marrieds probably go 18 months without having sex precisely because they want to and can since they don’t have any clock-watchers like him around. 

So six of one and half a dozen of the other. 

In any case, you should be mindful of the fact that “Sex With Eugene” is a problems column and you wrote to a problems column, meaning: I suspect that you think this is a problem in need of an answer. So my advice is this, to quote John Turturro from Miller’s Crossing: “Look into your heart.” And if that’s too indirect, how about this: Get OUT … while you can.


Hand Over Fist

EUGENE, SIR: Why would a straight guy, an ex, want to … no kinder way to put this, fist me in the rear? A power thing? Or he’s just so jaded from the usual control play? Mind you, I have not seen him in years, so it might be his e-fantasy. I said I am hesitant. He said he thought it would have to be something I was into in terms of the surrender. Just FYI: He’s a dom but this was never part of our play before. I recall in the very beginning he asked me if I was into it and I told him no back then. He’s not tried to get together in over two years, but he connects by email now and again. This just seems a little strong this soon into a return engagement. —Ahnika

Dear Butt, No:

I don’t know your ex, but asking why he’d like to put his entire hand into an orifice of yours and whether or not this informs on his usual sexual practice/preference is also probably one of those “knowable but unknown” things popular in America under George W. Bush. But if this had not been part of your practice before, two years later, with little or not contact in between, his shooting for the moon, so to speak, should be understood as the “what the hell-ism” that it is. Or like Nelly says, “I’m just kidding … unless you’re going for it.”

So he gave voice to either a penchant or a fantasy. Why he gave voice to it? This is unknown. Why he likes it, “it” being a sex act that is non-penis based and that gives neither of you any sort of direct sexual pleasure in the way that oral sex, for example, might? Well, part of it is something you said and the rest is something I said. Power and power play, a healthy part of sex sometimes, might certainly be a reason. And a penis that fails to radiate that power and the play that’s part of it might seek the same elsewhere. That elsewhere being fisting.

But these are just guesses. Advice that you didn’t ask for, though, and which I will give: Though this may have been on your bucket list of ways to spend Monday night, he had no way of knowing this. In fact, on the basis of what he knew, he knew you’d not be into this. So him suggesting it? Mark him as what Shakespeare would have called a jackanapes. Someone to not be taken seriously at all. And if he reads this column, he should know that he probably could have eased his way into this if, like many men, he had just a little patience. If he were to disagree, I’d suggest a little turnaround as fair play too. I mean, what’s the big deal?

Three by Land

EUGENE, SIR: New sex tricks? I need one! Got invited to a threesome and I want to impress. —Brian

Dear Dress to Impress:

A question that reveals more about the answerer than the questioner. A friend of mine used to work phone sex lines and would advise men to put ice cubes up their butts as this was the newest trend in sex trickery, and about part of that she was right. The “sex trickery” part. As in: This was just some shit she made up. But it underscores a certain approach that’s useful — making things up. Most people are bad at this and crutch their way through with porn, but I’ve found actual, real people much more inventive/imaginative than anything I’ve ever seen in porn. So clear your head, breathe deeply and plumb your imagination for the coolest thing you can think of that people might do with their clothes off; and if it doesn’t involve a felony, you might have a winner.

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