My First Double Penetration

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).

HIM: Well, technically that’s not true. You’ve had a cock in your pussy and another in your mouth before. Lots of times, in fact. Surely that counts.

HER: Um, no. That has its own name in the vernacular: it’s called a ‘spit roast’. Highly descriptive and highly offensive at the same time. Let’s face it: whenever anyone talks about a DP they are referring to one cock in the vagina and another in the ass. That’s the gold standard. I think nothing says that a lady is a serious sexual player as much as having a DP.

HIM: That I would agree with. If someone had asked me two years ago, I would have guessed you would never try it. You haven’t been a big fan of anal sex in the past, so the idea of adding a significant degree of difficulty to something you already feel lukewarm about just didn’t seem likely to happen.

HER: Well, it’s not that simple. You’re mostly right that I haven’t been a big fan of anal sex in the past, except that on certain occasions I have felt downright desperate for it. There have been times when that very specific kind of pain has been the thing I wanted the most. I can’t explain why the desire comes and goes. But I have been going through a bit of an anal phase lately. I did it with Dominic at a party recently, and then there was that time last week when your cock was in my ass while my vibrator filled my pussy. That was what really got me thinking seriously about who our best prospect would be if we were going to actually do this thing.

HIM: Well, I definitely didn’t think there was any kind of momentum in that direction when we invited Derek over for dinner. He’s our longest-standing single male MFM threesome partner, so I knew the evening would end with sex. If anything, I thought there might be a little bit of a bi-male exploration, because we’ve been inching in that direction for years now.

HER: Derek happens to be a wonderful photographer, so we’ve come to expect that taking sensual photos will be part of our foreplay. This time, we set up a black backdrop in our bedroom and spent some time getting shots that required me to take off more and more clothes. 

HIM: That kind of photography is interesting: a creative endeavour in its own right, and a prelude to something more exciting. Eventually you were completely naked, and after a while it was clear Derek was struggling to concentrate on the technical details of getting a good shot. At that moment, you undid his pants and started blowing him. I watched you two as I slowly took off my own clothes. I always enjoy seeing you with another man, but eventually it was my turn to get involved. You knelt on the bed and took my cock in your mouth as Derek licked your pussy and ass from behind. From there, we went through our usual routine of taking turns fucking you while the other one watched, often while you entertained the extra cock with your exquisite combination of touch and tongue.

HER: I love the ease and fluidity we’ve established with him. You two are both so unselfconscious about the enjoyment you get out of watching each other with me. At one point, as I straddled him, I decided to go for it. I asked you if you wanted to put your cock in my ass while I continued to fuck Derek. I knew my invitation would have more than the standard appeal. I was pretty sure that, for both you and Derek, a big part of the turn-on would be the proximity of your cocks to each other.

HIM: Nice idea, but I can say with a high level of confidence that that made up precisely zero percent of my thoughts on your offer. I like to try new things, and I’m definitely interested in exploring my bi side, but my main concern was your comfort. Maybe it’s a man thing, but I could not juggle two sensitive objectives in the same sex act. But beyond that there were the practical concerns. A DP is a feat requiring certain gymnastic skills. It seemed to me like there would be a lot of core strength involved. Also: where would all the legs go? How do the two people on top keep from crushing the one on the bottom? You were straddling him on your knees, and I didn’t know if I could get low enough to enter your ass at the right angle. So it took me a moment of pythagorean calculation to figure out how to even approach your request.

HER: Wow, you really are an over-thinker!

HIM: You have to understand that this is a risky manoeuvre. If over-thinking was ever required, now would be the time. Everyone knows that with any kind of anal penetration, you have to use more lube than you think you’ll need, and you have to go very slowly. So, I got everything nice and slippery, and proceeded with caution. I was grateful when I felt your fingers there to help guide me. I went so slowly and I was so lubed up that, at one point, I had to ask if I was inside you yet. You assured me that I was, so, at this point, I paused for a moment of inner celebration. We had done it: we had successfully achieved double-penetration! There I was, frozen like Sir Edmund Hilary posing for a picture at the summit of Mount Everest. But, of course, it’s not about just checking some feat of daring-do off of a list. This is sex. It’s about having fun. When you squealed in pain a moment later, however, I realized there were now at least two of us who weren’t focused on having fun.

HER: It was just momentary discomfort — you passed that threshold that I would guess anyone who’s had anal with a thick man will recognize. Once you are in, though, I can generally relax and loosen up. But you were so hyper-sensitive to my potential for pain, you immediately withdrew.

HIM: Yeah, there’s nothing about my mental make-up that would assume it was your job to adjust. I hate the thought of picking a restaurant you don’t absolutely love. Physically hurting you is the stuff of nightmares for me. So it was interesting that you didn’t give up there. You suggested we try again, this time with me in the front, and Derek in the back. So I went to wash up and came back for part two.

HER: By this point, I was determined to make this work. It wasn’t about merely fitting two cocks inside me and then setting off the fireworks. There would have to be thrusting. There would have to be actual fucking. I really wanted to experience the intense, full feeling I so enjoyed when you and I used toys to create our ‘artificial DP’ a few nights earlier. But I have to admit that part of me is just competitive. I wanted to be able to say that I’ve had a successful double penetration. And I thought it might be easier to handle Derek’s cock in my ass since it’s — how do I say this — a little less girthy than yours.

HIM: It’s funny, I’ve heard you say that before, and I’ve never believed you. My feeling is that it would be obvious to any objective observer that Derek’s penis is both longer and thicker than mine. I thought you were just being a good wife when you would say that (the first lesson in the Good Wife’s Handbook being, of course, to always praise your man’s endowment in whatever way you can credibly manage). Yet this was a situation when the issue of relative cock size had totally practical implications. No time for ego stroking. With so much on the line, it seemed like you really did think I had the thicker cock.

HER: Well, just so you know, the first lesson in the Good Husband’s Handbook is not to constantly obsess over your endowment. It’s not attractive.

HIM: Sorry.

HER: So there I was on top of you, face to face, and spreading my legs as wide as I could. My thinking was that Derek should be able to straddle your legs while still being between mine. It took a few adjustments, but he eventually got in and was able to start thrusting with my encouragement. It was crazy intense. In fact, the sensations in my ass were so overwhelming that I couldn’t even feel you in the front. It was like your cock disappeared in the haze of fullness and pressure. How was it for you?

HIM: Well, I couldn’t really move. As the foundation of this complex sex structure we had assembled, I felt my job was to just hold steady.

HER: One of the things I was curious about in a DP was if the men would feel each other’s cocks when they were inside the woman. So, did you?

HIM: I actually did. I felt the ridge of his cock head pass mine on the way through with each thrust.

HER: And did that turn you on?

HIM: Not really. It was anatomically illuminating, yes, but not arousing. Having said that, though, I had no problem staying hard through the whole thing. The DP was clearly working for me at some level, but I honestly think it was all about you. A DP is a pretty transgressive thing for a woman to do, and transgressive is hot for me. On the other hand, I was also feeling very proud of you as you urged Derek to go deeper, but I’m not sure if there’s such a thing as a pride boner.

HER: If there is, I would have had one too. I felt a real sense of accomplishment. After a little while of Derek thrusting, that pain I had been craving turned back into just good old-fashioned pain, and that’s when I let you guys know that the experiment was over.

HIM: I would have understood if we were finished for the evening at that point even though none of us had come. Though orgasms aren’t everything, you’ve never been one to stop after the main course if there was a good dessert on the menu.

HER: Yes. Even though my ass was kind of on fire, my clit was still open for business. And you know, I hate the idea of leaving a customer unsatisfied, so I was definitely far from finished. So after you fucked me to an orgasm in the usual manner, the two of you took turns getting off.

HIM: I felt satisfied on every level. We had tried something new without planning to, and the whole experience had evolved organically with a minimum of angst. That’s about as good as it gets in the lifestyle.

HER: While a DP is never going to be a part of our regular repertoire (that shit is complicated!), I’m glad we did it. I’d definitely be open to trying it again … just not too soon.