Our twenty-first-century rogue tells you how to deal when you’re suddenly faced with a friend’s naked oversharing.
Illustration by Celia Calle

The other night, I was in the middle of performing my nightly ritual of masturbating before bed. I was on my tablet surfing an amateur porn website where photos are submitted by users. One woman was featured in more than 20 photos, mostly naked self portraits that looked like cellphone photos, and a few of her hard-core fucking. She, and the pics, would have been extremely hot if it weren’t for the fact that she’s my wife’s best friend. I’m not sure what to do in this situation, or if I should do anything at all. If I tell my wife, I have to suffer the slight embarrassment of admitting to whacking it to online porn. Or do I pretend the photos don’t exist and hope her friend knows she’s naked and fucking on the internet?

Before we get into my answer to your dilemma, here is a fascinating game for everyone to play. Ring up your old man and ask him how many people he knows who have posed naked, or who he’s seen nude photos of. Next, ask your friends. Finally, find a couple of teens and
college-age kids and ask them. Don’t be alarmed by the massive jump in numbers, or by the photos those college students have saved on their phones. (Okay, set aside the results of that informal survey.)

Now let’s squash the idea that your wife is clueless about your nightly pecker-poundings. She knows full well what you’re doing in the bathroom for 20 minutes before bed. My guess is that if it keeps you off her ass (literally and figuratively) for the evening so she can watch The Next Iron Chef, she’s all for your nightly knob-knocking.

You’re missing the most obvious solution: Go right to the best friend about the photos. There are a couple of likely outcomes. One, you tell her what you saw and maybe even provide her with a link. (Don’t be embarrassed about admitting to your perusal of porn, since you’re not the one getting slammed online for all the world to save to their hard drive.) Tell her that you didn’t tell your wife because you figure the fewer people who know, the better. She might be oblivious to the photos and thankful for your honesty and discretion.

The second possible scenario is, she submitted those photos to the website herself and is just as horny as she appears on the web. You’re now face-to-face with possible side action. Of course, there is the sticky situation of your new fuck buddy being totally cool with posting personal sex photos online. Be careful. Remember that survey you did? Do you really want all those people to answer, “You mean besides you?”

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