Anal Sex

anal sex
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.

HER: So is hand-holding or passionate lovemaking. But seriously, I don’t consider you an anal afficionado. In our eight years together we’ve done it, what, six times?

HIM: Well, six times before a recent house party, when you kind of went crazy. But more about that later. You’re right, anal sex hasn’t been an obsession of mine. While I think of it as very intimate, the act itself just doesn’t seem worth all the trouble. Every guide to anal sex talks about the importance of going slow, and using lots of lube, because the potential for pain and injury is always present. That seems like a lot of distraction when you’re just trying to have some fun.

HER: Well, I have had a complicated relationship with my ass from birth. According to my mother, when I was a newborn, I didn’t poop for a week. She took me to a doctor, who stuck his unlubricated index finger up my tiny anus. I screamed so violently it made my mom cry. Apparently I was bruised for a week. My mother likes to blame this incident for my lifelong anal-retentiveness (both literal and figurative). Now, I don’t know how much of our adult attitudes stem from early bodily trauma — if they did, every circumcised man would be afraid to touch his penis — but this apocryphal tale does set the stage for my thoughts about anal sex: it hurts. It hurt when I tried it for the first time with my first husband (who was very large), and it has hurt almost every time I’ve done it since. There was a time, however, — a very brief time, as it turned out — when that specific kind of pain actually appealed to me. I don’t know what it was, but I found myself craving anal because of the pain, not in spite of it.

HIM: I’ve always had trouble with that side of your sexual desire. You love being spanked, flogged, and choked, but causing anyone pain is the opposite of what turns me on.

HER: I do love those things. And I think, early in our relationship, I knew I wanted some pain, but I wasn’t sure what variety would turn me on the most. Anal wasn’t it, as it turned out. I much prefer spanking, which is one of the most reliable ways to get you hard lately.

HIM: You’re right, but it’s not inflicting pain that turns me on. It’s the transgressive nature of the act. The fact that it goes so far against my normal inclinations is what makes it sexy.

HER: Well, in the world of vanilla sex, you can’t get much more transgressive than anal. And at last night’s party, I was feeling a little naughty. It all started with a lock-and-key game conversation between me and Dominic (a frequent partner). We were at a friend’s house, and he and I got paired up. Since we know each other so well, we skipped the pleasantries and somehow got straight into a conversation about anal. He impressed me with his casual and knowledgeable answers. His partner, Maria, loves anal. In fact, that was the very first way they had sex. He made it seem like going in the back door was a skill and he had the know-how. My craving for that type of pain suddenly came back. I told him I’d like to try it with him sometime.

HIM: Later, when we were swapping with Maria and Dominic in the playroom, I heard you say something to him like, “Do you want to put it in my ass?” I was obviously trying to be ‘in the moment’ with Maria, but, at the same time, I couldn’t believe what I was hearing! Of course, I had no idea about your conversation with Dominic upstairs, so, for me, this came completely out of the blue.

HER: Did it turn you on?

HIM: Definitely! The thing I love the most about you being with another man is when you are enthusiastic. Offering anal is not exactly something you do when you can’t think of anything else to say. Dominic’s wife Maria and I have been taking our time getting to know each other, while you and Dominic have had sex several times. Maria and I get along fantastically, but we had just never gone beyond oral sex. Hearing you announce that you wanted Dominic’s cock in your ass made me instantly hard, and suddenly Maria and I were having full-on sex for the first time.

HER: I was so happy for you! But I was a little worried that it might make you jealous that I haven’t had anal with you in a long time, but there I was offering it up to someone else. That didn’t sting a little?

HIM: No. I’m weird that way. I think you could literally look in my eyes over breakfast tomorrow and tell me you’re having a gang bang at a biker’s club house after work and I would say, “That’s cool, baby. Don’t forget to take pictures.”

HER: Well, there’s no danger of that happening. I’m not good with beards, for starters. But I did get pretty slutty at that party. True to his word, Dominic was a master of the art of anal. He went so slowly and had me so relaxed, that it actually didn’t hurt. I came hard at least once. After I washed up, I wandered into another room where there was an FMF threesome happening. These were people I had just met that night. In fact, I don’t know if I even spoke to the man more than a cursory introduction, and even at this moment I can’t remember his name. But I wasn’t worried too much about him. I saw an available pussy and got between that woman’s legs. I’m helpful like that.

HIM: Yes you are. But sometimes your helpful nature gets taken advantage of, and this seemed to me like one of those occasions. In this situation you ran into a classic lifestyle problem: you were attracted to a pussy, but that pussy was attached to a woman and that woman was attached to a man. Before long he felt some entitlement to your pussy, which was not what you thought you were signing up for.

HER: Well, he was good looking, which was nice because I was just drunk enough to fall into the ‘indiscriminate’ zone. Basically, I was horny, and he was there. He started fucking me enthusiastically, holding my legs up over my head. I’ve always loved that position, so I wasn’t about to complain.

HIM: I had stayed in the other room a little longer with Maria, so by the time I found you, you were already fucking this new guy. Unfortunately, I arrived just in time to hear you squeal in pain. It was a sound I had, unfortunately, heard before.

HER: The guy had pulled out too far during one particularly rigorous thrust, and his hard cock slammed into my ass on the downstroke. All the way in. Now, you might think that, after the lube and relaxation of having anal just 15 minutes earlier, I’d be okay. But no. It hurt. A lot.

And, as you say, it’s not the first time I’ve experienced that particular surprise. A couple of years ago, our long-time threesome partner Derrick made the same mistake. In that case, he was doing me hard doggie-style, and there was no lube or anal preparation before he jammed it all the way in. That time was even worse. I was in pain for three days. With this more recent ‘accident,’ I only hurt for a day. So, I guess I was helped by the preparation.

HIM: Well, that’s very understanding of you, but I have to say that I just don’t see how someone could make that mistake innocently. Had this guy seen you with Dominic and thought your ass was fair game? Had he taken a chance, and only claimed it was an accident when you yelled? Could anyone be that presumptuous? I have had sex with you over a thousand times (yes, I have the records to prove it!), and that has never happened with us. Fast or slow, deep or shallow, keeping to the designated opening has never seemed challenging to me.

HER: So you think the same thing about Derrick?

HIM: Well, we’ve known him a long time, and he’s a sweet, sensitive person. I’m inclined to give him a pass. I just can’t imagine him trying something like that opportunistically. But that still doesn’t mean I get it. I have a cock. I know how they work.  

HER: I know you’ve always harbored doubts about this. That’s why, when it happened again, I did an informal Twitter poll to see how many other people had experienced ‘accidental anal’. A few people said this same thing had happened to them. But, more often, there were near misses: ‘pokes’ in the wrong place that were caught before things went too far. So, I guess it could be a combination of alcohol, genuine error and lack of awareness, blended with the unfamiliarity of a new partner. I’m inclined to give both those guys the benefit of the doubt.

HIM: Well, I will say this much: after you rolled out from under the guy at the party, the apologies were pouring out of him. You managed a reassuring “don’t worry about it” as you walked over to me and took my arm. At this point, anyone would think that you would be tapping out for the evening. But that’s not what happened. You and I went around the corner to a private bedroom for what I assumed would be some gentle reconnection time. I was sure you weren’t interested in more sex. I figured my role would be to provide a little solace after your traumatic encounter. So I was shocked when you offered me a turn to give you anal.

HER: That was ill-advised, I now realize. But at that moment I felt a little guilty. These two other men had gotten in my ass, so I figured you deserved a chance too before I sobered up or lost my nerve.

HIM: Well, I was certainly grateful. Considering all that had gone down I should have declined, but when I asked if you were sure, you said “no problem” pretty convincingly. So I went slowly, and soon enough I was all the way in. It felt fantastic, in that tight way that anal sex is famous for. And sweetie, you did an amazing job of portraying someone who was relaxed and comfortable and into it.

HER: I’m pretty sure I’ve got an Oscar nomination coming. Comfortable would definitly be an overstatement. It was very … tender back there. Again, though, the pain was part of the pleasure. I came again (maybe twice). As did you, all over my lower back: the traditional way of rounding out a swinger event.

HIM: It’s funny looking back at my “anal sex, anal sex, and anal sex,” answer to the top three fantasies question all those years ago. It’s clear that I had a completely fetishized view of the act itself and what it meant. Now, it’s all about context for me. On the night of the party, I wasn’t looking for anal. It really hadn’t been on the agenda with us for a long time. But the fact that you did it spontaneously with Dominic, who is a true gentleman, turned it into something fresh and excitng. Come to think of it, that’s a big part of what I value about you as my partner in the lifestyle: your improv skills. Your instincts in the heat of the moment are first rate. Improv is all about responding to the other people in a scene, doing the thing that seems both totally perfect and totally surprising at the same time. It can’t be scripted. So even now, as awesome as that was (and holy fuck, it was awesome!), I’m not obsessed with having anal sex again soon. I mean, I’m sure we will do it at some point in the future, but it will almost certainly be in a situation where it’s completely unexpected.

HER: Well, as long as you mean the good kind of unexpected, not the ‘sorry I missed your pussy on that last stroke’ kind of unexpected, count me in.


  1. Nain Singh says:

    Candid expressions
    No wonder you to are together and happy

  2. S says:

    Fabulous blog

    1. Him and Her says:

      Thanks for reading!

Comments are closed.