Four Crazy Weekends

HER: As we looked back over our last few articles, we realized there hasn’t been much sexiness. But that doesn’t mean we’ve been behaving ourselves. Quite the contrary, actually. We’ve been very busy. Last month was one for the record books – four lifestyle events, four weekends in a row. So, for our sixtieth article (trumpet flourish), here are the highlights.

WEEKEND #1 – THE COUNTRY RETREAT

HIM: A good friend of ours has access through his business to a house that was once the temporary home of Mick Jagger and his entourage when The Rolling Stones were rehearsing in Toronto for a tour. His idea was to have four couples spend Friday through Sunday together in a casual environment without the sometimes artificial pacing of the typical lifestyle event. You know how it often goes — “ok people, enough talking/eating/swimming/dancing, time to start fucking!” We had thought of organizing something like this ourselves but it proved harder than we had thought it would be.

HER: So we were thrilled when all we had to do was pack an overnight bag and show up. As we emerged from the long, leafy driveway, we were blown away by the gorgeous private lake and stately country manor. We were even more impressed after the tour revealed nine bedrooms, five baths, a sauna, hot tub, and infinity pool. Then there was the amazing dinner served up by a private chef. We felt like guilty teenagers trying to keep our conversation civil for the sake of the chef and his assistant.

HIM: After they left, the clothes came off quickly as we all headed to the hot tub. It was a cool night, and the hot tub was some distance away from the house, so some naked sprinting was involved. Once we were settled in, the more uninhibited conversation we had been supressing at the dining room table resumed. Eventually those conversations morphed into action, but I forget exactly how that happened.

HER: It was Sarah who straddled Colin (not her husband) and started rubbing and moaning. I remember being unsure about exactly what was going on beneath the water. Were they actually doing it or just dry-humping, as we would have said in middle school?

HIM: Does it still qualify as dry-humping if it’s happening under water?

HER: You know what I mean. We had all remembered our drinks, but no one had thought to bring condoms out with them and the house was too far away to make a quick grab. But we were the newcomers to this tight-knit group who had known each other for 17 years, so, as I watched her sliding up and down with more urgency, I wondered if maybe they had a ‘no protection required’ arrangement.

HIM: I was thinking the same thing, and that uncertainty actually got me rock hard. You know bare-back swapping is a powerful fantasy for me, so watching other people do it is definitely the safest form. Laurie, who I had been flirting with over the course of a few events, must have read my mind and straddled me too. This time, I was sure it was only (let’s call it) wet-dry-humping, but feeling her pussy lips rub up and down the shaft of my cock while I watched the action unfolding around me was exquisite. We went on like that for what seemed like half an hour, but it couldn’t have really been that long. We were having a perfectly casual conversation above the water and a perfectly carnal one beneath it – my favorite combination.

HER: Meanwhile, I had been casually running my hand over Ben’s thigh. Ben is a shorter guy with a surprisingly nice cock and a sentimental streak a mile wide. He started kissing my neck, so I straddled him (clearly a trend this evening), to take advantage of the cock that I had made hard and let him get better access to my neck. We were both loving it. After rubbing my clit on him for a while, he whispered that I should stop or he’d come. I said, rather cavalierly, “Go ahead. It’s not my hot tub!” So he did. Feeling like I had a formula that was working, I moved over to Colin, hopped on, and rode him until he came too. We all decided to get out shortly after that. Ick.

HIM: Hold on now! While you were on your mission to alter the pH balance of the pool, I had moved over from Laurie to Kaitlyn. I had also spent a long time easing into a very sweet connection with her, and this was another sort of culmination. She and I did everything you could do in a hot tub short of actual penetration. By the end of the evening, I felt like this was our most mutually successful lifestyle experience yet, where we both had very satisfying interactions with multiple people (in spite of the fact that neither of us came).

HER: And that was just the start of an amazing weekend.

WEEKEND #2: Pool Party

HIM: The very next weekend, we helped friends celebrate the completion of their backyard renovation. After ooh-ing and ahh-ing over the pool and waterfall, we all ended up naked in the pool … ’cause it was that kind of group. But this time, most of the interesting stuff happened out of the water on the outdoor sofa. I had been aware that you were making out with Craig in the pool. You soon whispered in my ear that you and he were heading for dry land.

HER: This time, I made sure that my bag with the condoms was close at hand. I lead Craig to the couch and, after getting him excited, rolled a condom onto his hard cock. I rode him, aware of putting on a nice show for those still in the pool. Then his girlfriend, Kerry, came up behind him, kissing the two of us for a while. She then came around behind me and rubbed her breasts up against my back while I moved up and down on her man. I dismounted, and we gave him a joint blowjob.

HIM: I was definitely enjoying that show, but by the time I had extricated myself from the conversation I was involved in, you were winding things down. That actually worked to my advantage, though. As you and Craig left, Kerry and I took up the baton. We had fantastic sex, considering that patio furniture rarely makes for a comfortable ride.

HER: After that, a bunch of us headed to the basement where I spent a long time going down on our hostess. I’m pretty sure I made her come, but it would be nice if there was some kind of alert system so you could tell for sure. The night ended as so many do: with a bunch of naked people eating around the island in the kitchen. It was a great party.

WEEKEND #3: The Birthday Get-Together

HER: Our long-time friends, Dominic and Maria (Niagara Hotel Take Over) rented a cottage to host his 40th birthday party. We were among the first to arrive, which gave us a chance to get to know the other two couples there. I’m grateful for that, because, once things got started, they moved fast, and there was no more time for conversation.

HIM: When most of the guests had arrived, our hosts brought out a pair of home-made dice made of a box with naughty-to-very-naughty suggestions printed on the sides. What might have seemed a little hokey actually worked spctacularly well, but, of course, that depends on everyone buying in. ‘Remove one piece of clothing’ seemed to be over-represented, and after a few rounds, everyone was naked.

HER: A naked couple beckoned me over to the couch where they were making out with another woman. They were one of the couples we had spoken to earlier. Still on a high from their experience at Burning Man, which I suppose is the definition of middle-class cool circa 2018, they seemed nice enough. I went and dove in. The woman was cute, with a boyish figure, and she turned out to be gifted in the art of oral sex. But when I eventually opened my eyes, I saw you standing alone by the bar. You weren’t looking very happy.

HIM: I wasn’t. You were seeing what a man’s face looks like as he is in the midst of realizing he’s completely misplayed his hand. Earlier in the evening, things had started out really well. I had spent lots of time talking and flirting with Maria. During the dice game, I was the first guy fully naked, and, as you know, since I started my new diet, I’ve been feeling really good about my body. Maria and I were clearly in the zone, but when it came to play time, I started feeling like ‘Who am I to monopolize the hostess?’

HER: But she was giving you clear signals all night!

HIM: Oh — I know, I know. But that’s kind of how I was raised: don’t act like you’re special, keep your head down and, you know, don’t take the biggest piece of cake even when it’s offered. So, when you saw me at the bar, I was realizing that she had already moved on to someone else. I was feeling more than a little stupid. Not only had I lost out on what would have undoubtedly been a great experience, but I was worried that, in trying to do the right thing, I might have hurt her feelings.

HER: This is the first I’ve heard of this! I’m so sorry, baby! I know you two have been building toward something for a long time and never quite made it happen. Well that explains why, when I went upstairs with a couple I have never spoken to before, you came with me but just hovered by the door.

HIM: Yeah. In addition to my worry over blowing things with Maria, there were two other things on my mind: you had been drinking, which always makes me feel a little protective. I want you to have fun, but I want to make sure you’re treated with respect. The second thing was I wasn’t really attracted to the other woman in the room.

HER: Well, I was definitely attracted to him. Ok, let me be more specific: I was attracted to his cock. It was interesting — reasonably long and unreasonably thick. And hard as a diamond. After I left the couple on the sofa, I saw this woman giving him a blowjob in the middle of the living room. I asked if I could help her, and, before I knew it, he was suggesting we all go upstairs. But when we got there, I noticed your reticence and sensed that the other woman wasn’t too keen on sharing. I found out later that she was not his partner (I had assumed she was), so I was jumping in on her fun. He was certainly ready to take us both on, but I was sober enough to read the signals, so I left at the first opportunity.

HIM: The evening finished with us in the basement. You were flogged and fucked by Dominic, while I hung out with Maria. Overall, a good night for you, and a learning experience for me. Next time, I’ll try not to second guess what is so obviously a clear invitation from a beautiful woman.

WEEKEND #4: The Single Guy Hotel Event

HIM: Even though we were pretty lifestyle exhausted by this stage, I was excited about this event. It was hosted by our single male friend Justin (Big. Black. Cock.), and the concept was simple: an equal number of single guys, and couples who have played with single guys, would be brought together in a hotel suite. However, the reality did not quite live up to the potential of the concept.

HER: The first problem was that it was too popular: there were 55 people crammed into one sweltering suite. But the bigger issue was that the single guys all stood along the wall like it was a middle-school dance. There was hardly any attempt on their part to initiate contact with the couples.

HIM: I think that could have been overcome if the men had been more appealing. I had assumed that because Justin is so awesome — good-looking, intelligent, charming, confident — that the other single guys would be at least close to his level. But that was not the case. Honestly, did you see anyone that you wanted to fuck?

HER: Other than Justin? No. That’s why I suggested we get out of there and spend some quality time together in our own suite downstairs.

HIM: Which I thought was a great call, because we had taken three nights off sex to make sure we were extra turned on for this event. But, when it became clear nothing was going to happen upstairs, we broke that fast. Everything felt amazing. In fact, afterward I had this crazy thought that this was my best sexual performance ever.

HER: What?

HIM: I’m not saying it was your best experience ever, but if I wanted to show someone a demo real of my best work in bed, that was my best right there – lots of oral, lots of fast-and-slow fucking, smooth flow between positions, four orgasms for you. So while the event hadn’t been going that well, I definitely give Justin an assist on the play since I’m sure I was channeling some of the energy of the over crowded suite.

HER: Ok, well — congratulations to you! When we finished and went back upstairs, we found that security had shut the event down due to a noise complaint, and the party had been moved down to the lobby bar. It was there that we had the second redeeming encounter of the evening. We started talking to a couple of lovely ladies who introduced themselves as Tory and Sol. I immediately recognized their names from Twitter. They’re a same-sex married couple who are both bisexual and live in our city. We spent the rest of the night talking with them about sex, their trips to Desire, parenting, and their new podcast. It was a low key but very pleasant end to one crazy month.