My First Double Penetration

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Francois Boucher, RESTING GIRL, 1753

HER: This week we had two single-male dates in three days.

HIM: What were we thinking?

HER: This was one of those rare times where I felt compelled to fill every opening in our social schedule, and the only two single guys we have ever played with both happened to be free. The date on Tuesday (the subject of our previous article) included a first for us: you staying downstairs while I played alone with our sexy friend upstairs. Last night’s brought another new experience: my first double penetration (DP).

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The Single Male Experience

 

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Unknown Athenian Sculptor, The Riace Bronzes (Statue B), c. 460 B.C.

HER: I was deep into post-holiday work mode when a couple of texts lit up my phone.

Happy holidays gorgeous. Hope you are keeping well and had a lovely Christmas.

Thinking of you both. All the best for the new year as well. 😚 Would love to cross paths some time.

I got messages like this every few months from Justin, a friend we met four years ago. He was the first single male we ever met online and deemed worthy of a date. He’s still the only man I’ve met through a web site that I’ve ever had sex with. We’ve been on the once-a-year plan ever since, but we had somehow missed the most recent year. And this is one guy that I did not want to let slip through the cracks! Continue reading

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Fear of Fucking

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Franz Von Bayros, TALES FROM THE DRESSING TABLE: THE FETISHIST, 1908

HER: If opening up your relationship is a fantasy you hope to make a reality, you might imagine that having sex with other people is all fun and easy. Just mix three or more horny people together and let the carnal geometry unfold.

HIM: If only! That certainly hasn’t been the case for me. In fact, I feel badly if we have contributed to that misperception. Because the truth is, I have had erection struggles since the very beginning of our journey, and that has shaped my entire experience of the lifestyle. Continue reading

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Confessions of an Orgasm Faker

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Nan Goldin, The Ballad of Sexual Dependency, 1979-1995

HER: The house party was in full swing. I was lying in the middle of a mattress with the third person of the evening licking my pussy, doing their damnedest to make me come. There were no hard cocks around me, and I was nearly crying in frustration. Try as I might, I just could not crest the mountain. I considered faking it to make the guy feel better and end it, as I have done so many times before, but I didn’t have the energy this time. I can’t fake it anymore.

Confession: I’m shit at climaxing. There. I said it.

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Playing Separately

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Torii Kiyonobu, EROTIC CONTEST OF FLOWERS, c. 1710

HER: I’ve listened to three podcasts in the past month where well-known lifestyle personalities have expressed their discomfort with separate room play. Each of them said they would ‘never’ have sex without their partner present. And I understand where they’re coming from. We used to feel the same way.

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Naughty in N’awlins

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Thomas Couture, Les Romains de la Décadence, 1847

HER: When I was a kid, I ate an entire chocolate easter bunny in one sitting (who hasn’t?). And, of course, I got sick. I remember my mom saying something about too much of a good thing. Naughty in N’awlins was a little like that Easter bunny. Continue reading

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Swingers Take Italy

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Marc Chagall, Nude Over Vitebsk, 1933

HIM: There are two kinds of travellers. Tourists take in all the sights, but never get past the superficial. They remain outsiders. Adventurers connect with real people. They get to see things from an insider’s perspective. We always talk about how much the lifestyle has changed the way we live, and last month it happened again: the lifestyle turned a couple of Tourists into International Sex Adventurers. Continue reading

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Anal Sex

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Unknown Sculptor, Venus Callipyge (Roman copy of a Greek original), 1st Century BCE

HIM: I remember being in an online chat room many years ago when a woman I was interested in asked me what my top three fantasies were. “Anal sex, anal sex, and anal sex,” I replied.

HER: Wow, you were quite the charmer!

HIM: I know. It’s embarrassing looking back now. One of the Golden Rules of online profiles is never lead with anal sex.

HER: Making it all three of your top three fantasies is a little aggressive. So, did you get the girl?

HIM: Actually, I did. But that was obviously in spite of my adolescent enthusiasm, not because of it. And, no, we never actually had anal sex.

HER: Great story.

HIM: In my defense, though, I don’t think it was about asking for the dirtiest thing I could think of. In my mind, anal sex is all about intimacy.

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Breaking The Rules

Electric Underground Inka Essenhigh

Inka Essenhigh, ‘Electric Underground’, 2013

HIM: Max seemed to be silently fuming as I stood beside him in the door to our family room. By the fireplace was a massage table, and lying on that massage table was his wife, Melissa, naked and clearly in a state of bliss. You were looking pretty happy yourself, baby, as you and two male accomplices rubbed Melissa down with hot coconut oil. I asked Max if he and Melissa had discussed their boundaries for this type of scenario in advance, and the lid popped off his simmering rage — quietly, but unmistakably.

“No,” he replied, “we didn’t at all. In fact, we had one of the biggest fights of our marriage just this afternoon. I don’t see how she can magically become a totally different person so quickly.” I asked him if he wanted me to go over and diplomatically put an end to it. He told me not to bother. “She’s free to do what she wants,” he said, with a note of bitter resignation,  “but that doesn’t mean I have to stand here and watch it.” As he walked away, I worried that we might have inadvertently made their already rocky relationship worse by inviting them to this party.

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Sex Therapy

Self Portrait with Skeleton Marina Abramovic 2003

Marina Abramovic, Self Portrait with Skeleton, 2003

HER: What happens when swingers lose the desire to have sex?

HIM: Not much swinging.

HER: Nope. Or much of anything in the bedroom. This has been our reality for the past several months.

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