Antigua Diaries: A Series of Sixsomes

group sex
Fernand Leger, THREE WOMEN, 1921-22

HIM: I have to start by explaining a little something about myself. I’m an introvert. An unusually outgoing introvert, for sure, but an introvert all the same. Socializing exhausts me. As a result, I don’t like open-ended social engagements, even when group sex is on the menu. And I don’t travel with other people. I always need a trap door, an escape plan.  Time alone is how I refuel.

HER: So I get why you were a little hesitant when I volunteered for us to share a villa with Neil & Layla at Room 77′s hotel takeover in Antigua. But this was the deal of the century! One afternoon,  just before we left Miami after PCAP, Richard & Lauren announced that they were making four villas available to the first four groups who volunteered to share their accommodations. These villas were luxurious and massive. They were meant for six to eight people, and I knew they’d be snapped up quickly. The first people I thought of who were going to Antigua were Neil & Layla. We had only had one dinner with them in Miami a few days earlier. But the connection we all felt was strong right from the beginning, so I took a chance and sent them a text suggesting we be roommates for a week.

HIM: I agreed with you that Neil & Layla were a fantastic couple, and that the villas were worth pursuing. With that much space, I felt comfortable that I could find a private hideaway when I needed one. But I soon figured out that there was another dimension to this arrangement that most vacationers never have to think about: sex. We’re all swingers. Sharing accommodations meant not only that we’d inevitably be having sex with them, but that they would have to figure into all of our sexual maneuverings. 

HER: Was that a problem for you?

HIM: Kind of. Now, don’t get me wrong, they’re obviously an attractive couple. And you know I was infatuated with her ass! It wasn’t about attraction, it was more about coordination. What if we met some other couple and invited them back to our hot tub. Would etiquette require us to include Neil & Layla in our plans, or us in theirs? You know, right of first refusal and all that. What if we couldn’t find them in time? What if we had different tastes? Would there be hurt feelings or awkwardness?

HER: Wow, you really have a gift for analyzing the joy and spontaneity out of every opportunity, don’t you? My philosophy was, we’re cool, they’re cool, we’ll figure shit out. 

HIM: Well, as it turned out, they were our co-pilots for every sexual adventure we had that week, and the results could not have been more perfect. I’m used to relying on you to get things going with other people, but Neil & Layla also have serious game in that department. We ended up having three sixsomes —  each grouping made up of you & me, Neil & Layla, and one other custom-curated special guest star couple. 

HER: There were so many to choose from. Richard & Lauren put on an event for the ages, drawing a fantasy crowd of beautiful human beings to a luxurious island paradise. The first night we played with Adam & Eve from the Spiritual Swingers podcast. We had met them originally at Podcast-A-Palooza in 2018, and then again at Club Euphoria’s Foamageddon event in 2019. We had never played with them, but we were definitely looking forward to seeing them again and exploring the possibilities.

group sexHIM: This is something that happens to me from time to time — I become aware of someone in the lifestyle and think, “Oh, we’re going to get along perfectly.” With Adam & Eve, all I needed was to hear the name Spiritual Swingers, and I liked them without even seeing them. Soulfulness and sex are near to the heart of who I am as a person, so I was sure we’d have a lot in common. But for some reason, our conversations just never managed to achieve lift-off. 

HER: They, like you, seem to be a little introverted. She’s beautiful and statuesque. He’s well-built with piercing blue eyes. They weren’t lacking for attention from others, which might be part of why we struggled to connect with them for more than a few minutes at a time in the past.

HIM: Antigua was different, however. They seemed to be at the pool every moment of every day, so there were abundant opportunities for talking. When we finally had an unhurried chance to talk they came across as grounded, earthy even, while also soulful and idealistic. That’s a very attractive combination for someone like me. So I was ecstatic when Neil and Layla announced that they had set up a play session for the six of us. 

HER: Me too! We started with drinks in the hot tub, which would be the pattern for all three nights. Then we went up to the playroom (an extra bedroom at the villa we’d set up with lights and toys for exactly this purpose). The girls got things started with oral all around. Then the guys joined in. Adam did something I haven’t seen before: he had me straddle him, then he held me tight and pounded me from the bottom. It was impressively athletic!

HIM: Yeah, I overheard later that he does crunches while hanging upside down in his garage, so now I know why.

HER: That explains it. But I don’t remember you being around much that evening. Where were you? 

HIM: Do you remember when Eve said that she wanted to be a ‘fluffer’ for the day? She also mentioned something about giving a mean massage, so while you were busy with Adam, I asked her if she wanted to give me a massage in our room down the hall. 

HER: And that’s all you did? You just lay there taking a massage without giving her anything back?

HIM: No, we actually had a great conversation. But I interpreted her ‘fluffer’ comment to mean that she didn’t want to engage too intimately. A woman could have many reasons for that, so I thought that putting her in the driver’s seat as the masseuse was the best way to make her feel comfortable and involved.

HER: Ok, Gentleman Jim, but did you happen to notice Neil going down on her with reckless abandon? Eve didn’t seem to be trying too hard to escape.

group sexHIM: Neil is far more of a risk-taker than I am. In fact, his devil-may-care approach led directly to our second sixsome. I don’t know if you remember this, but the next day we were talking to him and Layla in the pool when he slipped away to pick up a drink. On his way back he stopped to chat with an extremely pretty young woman. Before long, they were locked in a passionate kiss. On the outside, I was chatting with you and Layla about her interesting Master’s Degree program, but on the inside, I was thinking, “Holy fucking fuck, Neil! How did you make that thing that never happens to me happen so effortlessly!” When I asked him later, he seemed to think it was the most natural occurrence in the world.

HER: I saw the same thing and gave Neil a high five afterward. That girl was smokin’ hot! Her name turned out to be Shirley, and her partner was Jonathan. After some conversation in the pool, we exchanged contact info. and agreed to have them over later that afternoon.

HIM: On their way over, there was a very interesting text exchange between us and them:

     Jonathan – Do you have a blindfold by any chance? Little bit of erotic chat going on here…

     Liam – We do have a blindfold.

     Shirley – How lovely! Not-so-subtly, may I ask to be blindfolded and directed to please?

     Kate – Sounds good!

     Jonathan – Hoping to have 5 of us enjoy the blindfolded Shirley…

HER: So just like that, we had a script for our afternoon play session. Again, we started out in the hot tub, but it wasn’t long before we moved up to the air conditioned comfort of the  playroom. We put the blindfold on Shirley and the group of us proceeded to do everything you could do to a blindfolded woman.

HIM: I quickly figured out that, while Jonathan wanted to see five people enjoying Shirley, there wasn’t a lot of real estate to go around. Shirley is quite petite, so I thought that maybe I could enjoy her with my camera. I asked Jonathan if that would be ok with them, and he said yes after whispering in Shirley’s ear and getting a nod in return. 

HER: After lots of caressing with hands and our feather tickler, I also thought I would use an instrument to enjoy Shirley with: my strap-on. I had brought the harness plus two sizes of dildos: large and really freakin’ large. I asked Jonathan if Shirley would be up for trying either or both and he again whispered the question in her ear. When he returned with an enthusiastic yes, I put on my gear. Jonathan asked if he could suck my dildo to lube it up. That was so erotic! Then I entered his girlfriend with the medium attachment. She took that easily, and I think she had an orgasm. Then we upped the ante and switched to the extra-large dildo. I was a little worried about her, given that she’s so petite. But I lubed up and put it in slowly.  She took it and came again as Jonathan held her head and Neil and Layla caressed her all over.

HIM: It was a great experience for me, trying to capture this story as it unfolded in front of me. Seeing this petite woman handle such a large cock was such a turn-on. When you finished, you went out on the balcony to cool down and I saw Jonathan follow you out. I assumed you were going to chat about what had just transpired.

HER: Well, what happened next was something I have never experienced before. In fact, I’ve never even heard of it. Jonathan was so turned on from watching his girl get fucked by another girl that he was as hard as a rock. I started stroking his cock as we watched the waves roll in. It seemed like the polite thing to do. It soon became obvious that he was going to come. I was surprised he was ready so quickly because you never orgasm from a handjob. Anyway, he went into a whole-body spasm, but there was no ejaculation. Apparently, this is something he does quite regularly. It seemed like he got to experience all of the ecstasy multiple times over with none of the mess. So practical!

group sexHIM: I have heard of that before, but I have never seen it. Very interesting. Meanwhile, something magical was happening inside. When you left, Neil & Layla and Shirley settled into a cuddle pile on the bed while I sat on a corner of the bed, distractedly looking at the footage on my camera. When Layla sat up from the group, however, I immediately snapped back into the present and started to kiss her. It was surprisingly passionate, probably a result of the intimacy that had built up between us from living together for the previous few days. I like to kiss, and I actually think I’m pretty good at it, but I’ve learned that you need the right partner. In my experience, you can’t be good on your own: a bad kisser turns both people into bad kissers. Fortunately, Layla is a really good kisser, and she brought out the best in me.

HER: Yes, I had kissed her a fair amount over the previous few days, and I can vouch for that.

HIM: After a while, I felt a body pressing into my back. Shirley had roused from her blissed-out repose and was now caressing me from behind. It was beyond exquisite. Both women found my cock with their hands, taking turns jerking me off while the other stroked my perineum. At times, they were double pumping my cock. I was in that place that the word heaven seems inadequate to describe. I wanted it to never end, and both women seemed to be in no hurry either. 

HER: When Jonathan and I came back in, we saw Neil circling you with the camera. I was so happy, seeing you as the center of so much attention,  and also the subject of videomaking. You almost never get to be in any of our videos because you’re always the one making them.

HIM: Like I said at the beginning of this article, I don’t like open-ended engagements. It turns out that applies even when I’m experiencing something amazing, I’m the one who has to say ‘enough’. As you mentioned, I never come from manual stimulation anyway, so I knew it probably wouldn’t end like that. So in spite of the fact that my every enraptured nerve ending in my body was begging me to keep the good times going, I eventually thanked both ladies in a way that said ‘this is over now’.

HER: Are you really sure you couldn’t have come? That’s the most aroused I’ve seen you with other women in a long time. I’ll bet you could have had an orgasm if you had let them continue.

HIM: Baby, it was one of the most pleasurable experiences I’ve ever had in the lifestyle. Maybe the most pleasurable, in fact.  But I hate the idea of reaching the top of the mountain and then starting to slide down the other side, seeing something great turn into something not so great because of a dumb lust for more more more. I was extremely happy, and looking back now, I wouldn’t change a thing.

HER: Well, I’ll take your word for it, I guess. But was there at least something you can learn from it, that you can apply to future encounters?

HIM: Unfortunately, no. This was a sexual situation sui generis, totally unique. How could I ever plan to repeat it — wait for everyone at an orgy to exhaust themselves before making my move? It was pure magic, and I prefer to be grateful that it happened once rather than lamenting the possibility that it might never happen again.

HER: Alright, this article is pretty long already and we didn’t even get to our third sixsome of that week. We’ve got some serious cutting to do here.

HIM: But we’ve already left out so much, I don’t want to cut it back further. Why don’t we just save that story for a stand alone article. It had a special magic of its own that deserves to be told in an unhurried way. 

HER: Agreed. Stay tuned….

 

 

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