In May 2021 we spoke at a lifestyle gathering in Miami called Podcast-A-Palooza. One hundred swinger couples from across North America gathered for three days of seminars and partying on South Beach. Unofficially, the event served as a kind of coming-out party after the privations of the Covid-19 pandemic. For us, it was the beginning of two weeks of epic stories. Here’s the second in the series about an evening of lucky accidents, including an erotic massage from eight strangers.

HIM: Our approach to events like Podcast-A-Palooza (PCAP) can be summed up in three words: never eat alone. For us, connection comes first in the lifestyle, and we want to connect with as many people as possible. Every meal that we eat by ourselves is a wasted opportunity to get to know some other couple at a deeper level. Who knows? They could become lifelong friends.

HER: I noticed Jennifer & Mark right away at a private reception that was the unofficial start of PCAP. She had a great smile and a vivacious energy that was obvious to anyone who laid eyes on her. Mark was quiet, but in that ‘still waters run deep’ kind of way. He was smart and funny, and loved to ask unexpected questions.

HIM: So, it was a no-brainer that we would ask Jennifer & Mark to dinner that first evening. They accepted and suggested a restaurant across the street from our hotel. Our meal together was fascinating. It still surprises me that we’ve had this kind of conversation so many times now, yet it never gets old. The story of how a couple got together in the first place, and how they eventually got into the lifestyle, is always unique. And swingers are typically not afraid to share their struggles, which are inevitable. They are what make the stories both more entertaining, and more humanizing. The conversation and laughs flowed easily, and we walked away from dinner with a very high opinion of Jennifer & Mark.

HER: Still, I have to say that it wasn’t obvious that we would have sex with them at this point. With three days and nights ahead of us, there was no rush to ‘seal the deal.’ Dinner was a great foundation, but we’re not the kind of people who operate from a master plan. We like to leave room for things to progress organically.

HIM: The next time we saw them was on the dance floor a couple of hours later. Dancing is an intriguing social phenomenon for many reasons. I think of each couple as a compound molecule, bouncing around in microscopic space, and it’s interesting to see what attractions reveal themselves as they circulate. Sure enough, we kept finding ourselves dancing beside Jennifer & Mark.

HER: The theme for the night was ‘Through the Looking Glass,’ based on the Alice in Wonderland story. By the way, we need to applaud Cate of Libertine Events for coming up with the most creative themes we’ve ever encountered. Everyone who has been to more than a few lifestyle events is familiar with the old standbys: Glow Night, Lingerie Night, Naughty Student Night, etc. Cate wanted to be different. After the Alice theme, there was the ‘Desert Rock Festival’ and ‘MTV Awards night’. Because we were taking only carry-on bags for our two-week adventure, our costume game was pretty weak. Jennifer & Mark, however, were on point every night. We were even more impressed when we found out that Mark had designed and made their costumes. Remember what I said about still waters running deep?

HIM: As the dancing wound down, we told Jennifer & Mark that we were going to one of the playrooms on the second floor and that we would be happy to meet them there. I like this approach: rather than propositioning a couple directly, we just provide them with coordinates which they can respond to by showing up. After changing into more comfortable (i.e. skimpier) clothes, we found them in the third playroom. Mark was sitting on a sofa and Jennifer was kneeling in front of him, beside a couple who were doing exactly the same thing. Magically, there seemed to be room for one more couple.

HER: It wasn’t long after we settled in that Jennifer and I decided to switch positions. I looked up into Mark’s eyes as I took his cock into my mouth.

HIM: As Jennifer stepped around you, I got up off the couch, took her face in my hands, and said, “Just because our partners are doing this, you should feel no pressure to do the same.” As perhaps the first male of our species who has ever asked a woman to think carefully before giving him oral sex, I think it took her a second to tune into what I was saying.

HER: You’re such a gentleman, but it was pretty obvious that she was into you. Why not just relax and enjoy the spontaneous pleasure?

HIM: It was actually for my benefit. The more convinced I am that a woman sincerely wants to do something with me, and isn’t just going with the flow, the more of a turn-on it is. Anyway, you were right: she was into it. So I sat back and enjoyed.

HER: After a while, we decided to move into the suite’s bedroom. We had a great time playing with each other’s spouses, then we switched back to our own partners. That’s generally the best way for me to orgasm, with you at the control panel. And it worked like a charm.

HIM: I was surprised that I didn’t come, because, while I was fucking you, Jennifer was playing with my ass and balls. That’s about the most physically pleasurable combination of sensations I can imagine, the kind of thing I love but could never actually ask a new partner for. But, for some reason, I just couldn’t get to the finish line.

HER: Once I had come, it seemed to mark the end of our time together. Our total lack of a plan had worked out perfectly! After some pleasant post-coital chat, we hugged our new friends and wandered back down the hall toward our room, completely naked. I imagined that we would have more sex there, so you could have your orgasm and I could maybe add on a few more. But, as we passed the last playroom, we saw an interesting scene: a large group of naked people gathered around a massage table that a woman was just climbing down from. Our timing was impeccable. It seemed like everyone turned around to look at us as if we were standing in a spotlight. One of the men immediately said to me, “You – you’re next!” He motioned toward the table. How could I refuse? I’m an adventurer at heart. I jumped on.

HIM: I was so fixated on getting back to our room that it took me a moment to adjust to this change in course. At first, I hung back, but it didn’t take me long to figure out that this surprise was going to work very well for me. It was like discovering a fantasy I didn’t know I had. Being a numbers guy, I did a quick count: there were eight people in total, which meant that you were going to get a sixteen-hand erotic massage!

HER: I probably should have thought a little more about it. I was going to be in a vulnerable position, face down among a group of horny strangers. I didn’t recognize a single person! But I guess inside I knew you’d be there to speak up for me if anyone got carried away.

HIM: I quickly assumed the last empty position around the table, at least partly to watch out for you while you couldn’t see what was happening. Someone had to be there to say, ‘She doesn’t really like fingers inside’, or ‘Gentle with those nipples’, or provide any other tidbits of crucial guidance. But it didn’t turn out to be necessary. They were a very respectful group, so my mindset quickly shifted from ‘helpful partner’ mode to ‘I can’t believe how fuckin’ hot this is!’ mode. I realized that this was like a gangbang lite.  Something about the vision of you being serviced by a large group of strangers turned me on like crazy.

HER: There I was, face down, slippery with coconut oil and relishing the touch of so many anonymous hands. At first, everyone was very cautious, staying away from any private areas. They massaged my legs and arms and back, just grazing my ass. But, the longer I was there, the more they ventured into my erogenous zones.

HIM: I think what turned me on the most was the actions of the women. They were so appreciative of your body. Fingertips traced the sides of your breasts and caressed your inner thighs. At one point when you were face down, I spread your cheeks as a woman I later learned was named Michelle reached out to caress your pussy. She stroked your clit with real enthusiasm. When she finally pulled her hand away (probably so someone else could have a turn), and with your cheeks still spread, she exclaimed, “Look at that gorgeous pussy!” I literally could have come in my pants and died at that moment.

HER: I was starting to feel a little selfish after what seemed like a long time on the table. I’m far more comfortable being a giver than a taker. But then someone told me to roll over, and, well, I’m also the kind of person who does what she’s told. I knew things were about to get even better, so I instinctively spread my legs. As soon as I got into position, a woman crawled up on the table and asked if she could lick my pussy. I didn’t even need to open my eyes and look at her to know that the answer was yes.

HIM: As someone whose eyes were wide open, let me tell you that your instincts were right. That woman was beautiful!

HER: She was soft and insistent with her tongue. And patient. She was definitely not in a hurry. At the same time, different men took turns at the head of the table, leaning in to kiss me and massage my breasts after first asking if that was okay. This group really understood consent! I was lost in the myriad sensations until one man went really deep with his tongue and the thought of COVID shook me out of my stupor. This was our first day here, and we had only had our first vaccinations. What was I doing?! I didn’t even know these people! Then Bomber from the Black and Kinky podcast kissed me and somehow, I forgot my objections. That man knows how to give the most delicious kisses! After that, things wound down and I thanked everyone as I got off the table as gracefully as my now wobbly legs could manage. I was on fire. I was anxious to get back to the room so I could have another orgasm…or five!

HIM: The sex between us was indeed spectacular. You asked me what I wanted, and I felt the weird stress of wanting to do everything at once while at that level of arousal. How about I spank your ass…or you spank my cock…or you sit on my face…or you suck my cock. Could we possibly do all those things at once? I settled on a massage, but it wasn’t long before I was begging to get inside you. I managed to get you a couple more orgasms before I finally exploded.

HER: In the end, I think what I enjoyed most about this night was the spontaneity. I tend to be a ‘go with the flow’ type of person in sexual situations, but you’ve always needed more time to feel comfortable. I remember watching you once telling a woman you had just been introduced to, “We are going to have amazing sex three years from now”.

HIM: I like to manage expectations.

HER: But look at you! That first night of PCAP, you were able to throw off the need for careful calculation and long periods of lead-up. We met, had dinner with, and had sex with a new couple, all in one evening. Then we leaped into the middle of this massage situation without any hesitation. It’s those unlooked-for, unexpected experiences and connections that bring me a lot of joy. I really appreciate the freedom of this lifestyle when we can just say ‘yes’ to whatever feels right and fun in the moment.

HIM: I did enjoy that, and that sense of spontaneity set the tone for the rest of our experience at Podcast-A-Palooza. It also reinforced an idea I’ve found myself thinking about a lot lately. It might sound strange, but I’ve been wondering if our entire lifestyle adventure is nothing more than the most elaborate foreplay two people have ever devised for themselves. Think about it: Jennifer & Mark were fantastic, and that sixteen-hand massage was amazing, but ultimately it all served as a prelude to you and I finally being alone together. It’s like everyone else was working hard to make things the best they could be for us. They were the supporting cast in a movie that we were starring in.

HER: That’s a little self-centered, don’t you think?

HIM: Not at all, because I expect that we were doing the exact same thing for them.  I’d love to think that some incidental touch or a word from us lit a fire in someone else. Who knows how many spectacular orgasms we played a small part in making possible?

HER: Which reminds me, I had left our door open when we went back to our room for sex that night. I figured maybe someone walking by after the massage might like to watch us. I had assumed no one did, which was fine, but it turned out I was wrong. The next morning, a man who I had seen earlier but never spoken to approached me and said, with emotion in his voice, that he and his wife had actually stood by our door and watched us for a long time. He said that our deep connectedness came across clearly in our love-making. In fact, it turned him and his wife on so much that they went back to their own room and had amazing sex, inspired by us. He actually had a tear in his eye as he told me. I was moved because I knew he had seen through the sex to witness the love you and I were feeling for each other. These are the kinds of unexpected moments no one tells you about when you first start thinking about opening your relationship.