Strap Yourself In: It’s Going to Be a Bumpy, Sexy Ride

Why go to couples therapy when you can turn to OZY's Eugene S. Robinson?

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Why you should care

OZY’s Eugene S. Robinson addresses queries from the love-weary in “Sex With Eugene.”

Peg of My Heart

EUGENE, SIR: My man wants me to “peg” him. I’ve been working out my sort of weirded-out feelings regarding gender role reversals, so I just really want to know, are there do’s and don’ts I need to know? Answering me sooner than later would be very helpful. —Strapping It On

Dear Strap-Happy: Hats off to you for even trying to work out the hows and whys of what you’re feeling when you consider the prospect of anally pleasuring your man. A friend of mine who, curiously enough worked at Burger King, told me one night how hard it was for him to find women who would do this. He said even the game girlfriends would eventually break down, and that tears were often involved, with them at some point screaming some variation of “I DON’T WANT TO BE THE MAN ANYMORE! I CAN’T DO THIS!” This puts him in a position of either having to forgo a clear-cut pleasure for the sake of her idea of what men do and don’t do, or let her go and keep going until he finds someone for whom this is a welcome and shared kink.

So, I’m sure he’d thank you. In regards to do’s and don’ts, if you’ve ever enjoyed anal sex from the receiving end, the same rules apply: lubrication, sensitivity and a blitzkrieg-like attack on his fundament. OK, I was just kidding with that last one. But Little Richard said it best in the unreleased and unexpurgated original words to his famous song Tutti Frutti, which was originally called Tutti Fruitti Good Booty: If it’s tight, it’s alright/If it’s greasy, it makes it easy. So yes, some water-based lubricant a little more significant than spit, and if you’re using a strap-on dildo, also consider a two-headed one so you all are having fun coming and going. Good luck.


Anal Intruder?

EUGENE, SIR: I met this woman online. We flirted like crazy, met for drinks and then started making plans to get sexy at our next meeting. We met at a hotel, headed up to the room and before the door had closed we were at it. No problems. In the middle, she says to me, “What is it with guys and anal?” Since we were at the time actually having anal sex, I thought she was joking and laughed and asked if she wanted me to stop. She said “no.” So we continued and had a great weekend together, but in the current environment, I wanted some clarity around this, so I asked her why she had asked, and she said that she thought I was maybe presuming too much doing that on the first date. Is that not a first-date activity? Is any sexual activity a first-date activity? And turning it around, I asked her what was with her and anal? I mean, she seemed to enjoy it, and when I asked if she enjoyed it, she confirmed she enjoyed it, but when I asked what were we talking about then, she waved it off. But now I’m a little irked but also don’t want to be part of some problem. Thoughts? — Going Where I’m Welcome

Dear GWIW: Easy. Seriously, take a breath. I think the tone and timber of our current discourse have us so keyed up for a fight (about things both worth fighting about and things very definitely NOT worth fighting about) that our ability to tell the difference or even walk right on by the unnecessary fights has just dropped to zero. The reality is anal sex has long been considered a taboo and, at the very least, it has been made mythical because of its taboo standing. As with any/many taboos, there are probably good and bad reasons that they have been taboos, but in regards to anal, specifically as it’s raised its head in your query, the issue is, is there a time that’s MORE right to engage in an activity that might require more than an amateur level of care and sensitivity?

And my answer is not going to make you happy, but here it is anyway: I don’t know.

Everyone is different, and you’re different with everyone. Moreover, I think sex works best when it’s depoliticized and when the participants are in a hungry hunt for that which pleases them the most because they’ve been granted/given license by a willing and similarly engaged partner. Which means that it could be the most right thing in the world or the most wrong, given the situation. Seems like she had moved beyond whatever her original concerns were, but you shouldn’t be unhappy that she wanted to talk about it. That’s what we do: talk about stuff we’re trying to figure out. Which is probably why you’re here now. Don’t stay irked. You’re not part of any problem.

Oh, Size DOES Matter

EUGENE, SIR: Who is pushing the lie that big penises do not matter? I just had my first over-8-inch penis and it made a big difference, all puns intended. Who benefits from the lie that size makes no difference? —Size Queen, No Regrets 

Dear Your Majesty: Listen, I don’t know who you’re thinking about here, but this is the business of generalities and, generally speaking, there are probably men out there with large penises who are ALSO bad in bed. So, it’s not automatic that a large penis will solve all of your problems. However, if what you’re suggesting is that assuming that the holders of a small penis and the holders of a large penis are both generally competent in bed, that it’s your belief that the larger penis will win out, well, OK. 

However, if you want my opinion, a much more reliable indicator of good sex is your partner’s ability to avoid saying (or doing) anything really, really stupid. Never has defeat been yanked from the jaws of victory more effectively than tangible proof that the person you’ve just had sex with is a fool. So, I stand by my previous advice of de-signifying the aesthetic or functional importance of larger penises in favor of understanding that any penis is only as good as its owner. 

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