HIM: I was in high school the first time I heard of a gang bang. It wasn’t in porn, but in Pliny the Elder’s Natural History. In Book X, published in the year 77 AD, he tells the story of Messalina, wife of the Emperor Claudius.  She was a beautiful young noblewoman who, among her other outrageous qualities, was widely reputed to be a nymphomaniac. It was said that she once engaged in a competition with a renowned prostitute to see who could have sex with the most men in a single day. Messalina won by a score of 25 to 24! While Pliny didn’t call it a gang bang, that’s exactly what it was.  

HER: Wait — you were reading Pliny the Elder in high school?

HIM: Ok, to be precise, I was reading a book whose title I can’t remember now that quoted Pliny the Elder. But that’s not the point. This story about a woman who so spectacularly rejected the ideal of feminine chastity seared itself into my imagination. Even at that age, I subconsciously longed to believe that sex wasn’t just a bargaining chip to be cashed in by women in exchange for the status and security of marriage. 

HER: Well, that explains a lot. Every time we talk about our sexual bucket lists, you remind me that one of the few things left undone on yours has been to arrange a gang bang for me. I have to admit, I’ve always felt uneasy when you’ve shared your vision of shopping online for the perfect group of men for me: respectful, fit, handsome, and nicely hung. You would have them come to a hotel room while you play the role of referee and videographer as they each had their way with me. While I’m generally  game to make all your fantasies come true, very little about that scenario appealed to me.

HIM: My goal was actually to make everything perfect for you, to spoil you sexually. What was I getting wrong?

HER: I’m just not that into the idea of fucking a bunch of strangers. Sex alone doesn’t turn me on all that much. I don’t think most women would say that getting fucked en masse is the epitome of sexual pleasure. I need to have my mind stimulated. I need to engage with a person in more than just a physical way, and that means meeting and having chemistry in advance of getting naked. I imagined me lying blindfolded on a bed while you ushered in these mystery men to take turns on me, but being too uncomfortable to have fun because I didn’t feel safe or connected to them. I also have a sensitive pussy and worried about it getting painful after a few guys.

HIM: That’s all understandable. To be honest, I had begun to think it would never happen. Which is fine, because it’s not your job to make all my dreams come true. Even if you were suddenly enthusiastic, setting up a gang bang is a very complex operation. It’s probably one of the hardest fantasies to bring to life. You have to start with a definition: how many men constitutes a gang bang? Is three enough, so it isn’t just an MFM threesome, or does it have to be an astonishing number, like Messalina’s group of 25? Once you’ve decided how many people you need, it’s like casting a play or a movie. The actors have to have the right looks and personalities, for starters. Then they must be available –and reliable enough — to all show up at the right time and place. Finally, they have to be capable of performing the role. It’s a lot of pressure. It’s the classic ‘you’ve only got one job’ scenario: to produce a serviceable erection and fuck the lady of honor when your number is called. In every porn video of this scenario, you see a few young, fit men struggling to play their part.

HER: Hey, you make it sound like it’s all about the men, but what about the lady involved? The guys at least get to tap out when their part is over, but there is one person who has to be involved every single minute. And while the men are each taking a turn focusing on one individual — her — she may be fucking one guy while sucking another and stroking yet another. It’s a lot of work!

HIM: I’m sorry, you’re right. It sounds like a thousand years of patriarchy folded into one sex act!

HER: But still, it’s not like I was uninterested. I’ve always had my ‘party favor’ fantasy, that you would tie me up on a bed blindfolded at one of our parties so that whoever wanted to could just come along and fuck me. The advantage of that scenario is that we only invite people I know and like to our parties. I might not know exactly who was doing me at any given time, but I would be sure that they were a nice person. I just couldn’t imagine myself feeling comfortable with a group of randos, however nicely hung they might be.

HIM: Yes, I’ve known about that fantasy for a long time, but we’ve never been able to make it happen. It would be like a special event that would still require a lot of coordination. And I’ve always felt like it might make the other women at our parties uncomfortable, as if you were trying to be the center of attention. 

HER: That’s what got me thinking, in advance of our recent trip to Desire, that this might be the perfect opportunity. The group we were meeting there was the same group we had spent a week with at Desire last year. They’re all friends of Jay and Kay from the TCND (That Couple Next Door) podcast, and they are all amazing human beings. In fact, I had played with three of the men on that last trip, and the only thing that stopped me from playing with the fourth was that we ran out of time. 

HIM: Which was perfect, since I had settled on the idea that five men was a good number for a lady’s first gang bang. Those four men, plus me, would be perfect. For those of you who follow the TCND podcast, and are familiar with the regular cast of characters, I’m talking about Jay, Nate, Rory and Chris. Still, it wasn’t a slam dunk. First, I had to find out if those men were interested, and then I had to find out about their wives.

HER: That part was important to me. These men weren’t four strangers dropping by a hotel room more or less anonymously: they were married to women I like and respect. Each of those couples had different swinging rules that would have to be taken into account, and we’d need everyone’s enthusiastic consent before we could move forward. No fantasy of ours would be worth bringing bad vibes into their relationships. 

HIM: Well, the women turned out to be very supportive. Two of them even expressed nearly identical sentiments that went something like this: ‘My husband is insatiable, so if you can take some of the pressure off me, you have not only my blessing, but my gratitude!’ It wasn’t too difficult from there to settle on a time and place. 

HER: Amy and Rory, the couple who volunteered to host, were staying in a beautiful villa that had a loft bedroom and a private pool. Everyone gathered there at the appointed time for some socializing, but it didn’t take long before the six of us all headed upstairs for the main event, leaving the women down in the pool with a fairly clear view of what was about to happen. I had decided in advance that I wanted to be blindfolded. I loved the idea of being entirely submissive with this group of men I trusted. I felt safe enough to give over control and be used however you all liked. I also thought the blindfold might help to eliminate the potential distractions of the whole procedural part and just let me focus on the sensations. What you guys were doing offstage wasn’t my concern if I couldn’t see it.

HIM: Once we were all ready, I laid out some simple rules. The most important was that, if at any point you felt uncomfortable, all you had to do was say ‘time out’ and it would be the job of any man interacting with you in any way to stop immediately. 

HER: I have to say, all this planning didn’t exactly make for the most arousing start to the experience. I felt like it was a little forced. There I was, blindfolded and naked on the bed, at the pre-set start time. But what happened next? Were you guys just going to lube up and dive in, or would someone be assigned the job of giving me a little foreplay? I knew I would get into it, but it wasn’t the most auspicious beginning.

HIM: Partly for that reason, I decided that I would start things off. I handed the camera to one of the guys so that my part could be recorded for posterity, then I got on the bed. You were lying on your back and I started by caressing you gently all over. Then I spread your legs and started stroking your pussy to get you warmed up. I even spanked your clit a bit.

HER: That’s when I knew it was you. It was kind of a bold move, and I didn’t think any of the other guys would lead with that.  

HIM: I was lucky, since I was the only guy who wouldn’t have to wear a condom. As I applied a little lube and prepared to enter you, you reached out both hands with gestures that said, ‘I can handle a couple more cocks here’.

HER: I had already worked out a kind of choreography in my mind — one man could fuck me, while I alternately stroked and sucked on two men kneeling close on either side of my face. The fourth man could then work the camera while the fifth was in the ‘on deck’ position, ready to replace whoever took the next time out. Of course, I was also very open to being surprised.

HIM: So tell me: was it fun at all for you, or was there too much going on? 

HER: It was fun in the way I imagine bungee jumping is fun. It’s exciting and crazy and new, but you don’t want to do it every day. I both liked and felt a little self-conscious about being the center of attention. It was exciting not to know what was going to happen next and to guess who was fucking me (which was actually fairly easy, since you all have different styles). But there was very little chance I’d have an orgasm. And I couldn’t have the same kind of one-on-one intensity that I usually love with a partner, where I feel really present and connected. My desire usually feeds off my partner’s excitement.

HIM: Any particularly memorable moments?

HER: Well, there was a lot going on, but some things do stand out. One was Jay’s new move (every time I’m with him, he whips out some innovative new position). This time it was something his wife Kay later dubbed ‘The Wheelbarrow’. I was kneeling on all fours while Jay did me from behind. Then he grabbed my ankles and pulled my feet up.  While I adore Jay’s spirit of innovation, my knees didn’t. That position didn’t last long before he grabbed a towel and used it under my hips to pull me toward him and maximize the thrusting. That was amazing.

I also remember getting pounded hard by Rory, who rocked my uterus in a not unpleasant way with his considerable length. Another thing that stood out was when I was flat on my stomach while Nate was on top of me. He was fucking me in the way I normally orgasm, with the kind of full-body contact and intense, tight holding that I love. The only problem was I had a cock in my mouth. With the full weight of Nate’s body on mine, I couldn’t lift my head to move up and down on the penis, which was getting shoved dangerously far down my throat. At one point, I thought I might have to tap out because it was getting a little suffocate-y, and not in a good way.

HIM: I have to say, it wasn’t all smooth sailing on the men’s side of the experience. I was glad you were blindfolded for those moments. At one point there seemed to be a consensus that we should try a DVP (Double Vaginal Penetration). I’m not sure where that came from, because you and I have never tried it before during a threesome or foursome, but I assume someone must have run it past you.

HER: It was Jay. I was riding him and he suggested someone come in from behind for a DVP. I figured, why not? It had already been a day of firsts. 

HIM: Nate was the closest to the bed, so he jumped back on. Unfortunately, he only heard the D and P parts of the acronym, but not the V, so he started lubing your ass. Nate is at the large end of the endowment spectrum, so I knew that wouldn’t go over well.  I clarified the situation for him, and he stepped aside like the true gentleman he is. I positioned myself to join Jay for the DVP, but about three seconds in, I realized that was never going to happen!

HER: Um, no. I would need a pair of less girthy men. It just did not feel physically possible.

HIM: After a while, there was only one man remaining who hadn’t had a turn, and it was Chris. There was a lot going on, but I had noticed at different times that he hadn’t really achieved a full erection while watching. I definitely know what that feels like, desperately scouring the scene in front of you — not to mention your entire sexual history — for anything your libido can latch onto. It began to feel like things were winding down as you lay on your tummy blowing Jay. Perhaps it just wasn’t Chris’s day. No problem, I thought, four out of five ain’t bad. But this seemed to be the moment when Chris found his mojo. He slipped a condom on and positioned himself behind you. 

HER: I recognized his lovely cock from the day before at the rooftop orgy. He had been the one to make me come so hard at the end, so it seemed fitting that he would also wrap up the proceedings on this day. I like his gentle, quiet energy. I don’t think he made me come this time, though, because I remember reaching for you and my vibrator at the end as the rest of the men hit the shower. That’s usually how I finally orgasm: with you. And I had a good, loud one.

HIM: When it was all over,  the wives in the pool (plus a few other audience members who had assembled) broke out in applause. I honestly think they were impressed by what you had done. So, my question is, would you do it again? Do you think it’s the kind of thing that could get better with practice?

HER: I usually say you should try everything twice because the first time is rarely the best. However, I wouldn’t seek it out. Honestly, it was too much to juggle. I don’t know how this Messalina chick handled 25 men. I’m a pleaser by nature. I always want to be sure my partners are satisfied, but having so many people to think about was distracting. I didn’t feel like I could just lie back and enjoy the sensations, because I wanted to be sure I was taking care of all the cocks. And I really missed the presence of women.  What I love most in group play situations is being able to move between different energies, to watch and touch and get involved with both the men and women.  But this was your fantasy. So, how was it for you? Was it everything you had hoped it would be?

HIM: You know, there’s something hopelessly artificial about bucket lists. While our best memories in life tend to be about things that happened by surprise, there is nothing surprising about the bucket list achievement. It is pre-programmed, carefully scripted, intentional. It says ‘time is running out, and I can’t depend on serendipity to deliver all the experiences I long for. I have to take matters into my own hands and make it happen myself.’ 

HER: So you were disappointed?

HIM: Not at all. Everyone involved was fantastic. We actually achieved this thing that is very difficult to do: have five men get hard on demand and fuck one woman. I have to admit, that feels good. But mainly, I was proud of you. You were game to try something new, to make a fantasy of mine come true, and you dove into it with energy and enthusiasm. You were the star of the show. So I am fine if we never try it again…unless you really want to, that is. That’s the key for me: nothing turns me on as much as seeing you turned on. So if that happens — if we should somehow stumble into a perfectly spontaneous, totally organic gang bang situation sometime in the future — I’m sure we’ll both benefit from having rehearsed all the moves in advance.