Lessons Learned from Our First Time Swinging

Fall 2019

So where does a married couple in the midst of the relatively conservative Midwest Suburbia find friends to fuck?

As a librarian, I’m ashamed to say that I didn’t do a thorough investigation of the best resources. Perhaps I was too excited to get started, perhaps I was too busy with back-to-school stuff.  Swinger podcasts and people we met at Hedo all seemed to unanimously recommend Kasidie.com, so that’s where we went first.

I can see how traditional swingers might like this site, but Jack and I weren’t the traditional full-swap couple.  In fact, I later discovered that Millennials and GenZs don’t use those terms — they call it “open,” “dating,” “non-monogamy,” or “poly”. “Swinger” has an entirely different connotation, and it wasn’t what we were going for.

I should have taken the hint from Kasidie’s profile structure. There’s this long checklist — they call it “Play Preferences and Clues.” We became overwhelmed considering the various possibilities. Kissing? Yes, but how do I specify just the ladies? Hand jobs? Oral sex? Full swap? Depends, right? Tickling? No thanks. Anal? Uh, didn’t we just meet? I just wanted an intimate female friend, dammit.

We skirted the checklist, which, despite its long list of ideas, felt limited to mostly heterosexual, swap-style interactions. Instead, we took to the blank box where we could write freely. We said that we were newbies, but that we were secure in our relationship as well as with nudity. We expressed my desire to have more experiences with other women, and added that we also desired to make true friends with whom we could be raw and real.

We posted a handful of sexy pictures, too, but omitted our faces from the public photos.
Then we scoured through the other profiles. This site was proving to be mostly couples, sometimes single men, and rarely single women. Most of the people seemed to be looking for hookups. 

I had thought I was a little risque putting up a photo of my cheeky bikini backside, but others were posting pussy pictures, titty shots, photos of people doing it doggie style. I hadn’t seen thumbnails like this anywhere other than YouPorn. I had been thinking about sex as beautiful and relationship-building, but this site made me feel sleazy.

Where were the other thirty-something moms who drank tea and read novels on weeknights? I wanted friends, not just big tits and a piece of ass, and certainly not an engorged uncircumcised cock. 

We weren’t opposed to flings on vacation. That no-strings-attached model seemed like an uncomplicated way to start off in this game. Like a frat party, you know? But if we were going to invest our time in this game at home, we wanted it to be a touch more meaningful. Actual friends, but ones who fooled around sometimes. This site screamed “One Night Stand.” Our people didn’t seem to be there.

Well, that’s not entirely accurate. There was one couple who piqued our interest immediately. They lived about an hour from us, and they had also vacationed at Hedo — several times. They oozed the vibes of fellow free-loving hippie types. And they were cute. 

We messaged them, and the guy promptly wrote back using correct grammar with a friendly tone — score! We chatted about Hedo and got some veteran advice from him. He seemed kind and intelligent, and the way he described his wife was intriguing. But then the frequency of our messages faded out. We got busy, and it seemed that they did, too.

We still wished for friends-with benefits, and I still felt the pull of my newly unearthed desires, but we were swamped with curriculum nights, apple picking, pumpkin carving, and all of the other events that fill up a suburban family life. We weren’t in a rush; we figured we’d let things happen naturally. 

In the meantime, we consciously worked on our one-on-one game at home. Immediately upon returning home from Hedo, we implemented music into our routine. I curated a soundtrack just for us, adding to it often. 

We browsed online stores for new sex toys. Our afternoons in our Hedo hotel room reinforced how much I enjoy being restrained, whether it was spread eagle on the bed or “just” my arms tied behind my back. We searched for BDSM toys, eventually settling on under-the-bed restraints that featured velvet velcro-closure cuffs. They looked like they’d hold better than our tie-on restraints, and they looked sexier, too. We also purchased a riding crop and vibrating kegel balls. 

When I took my son to his swim team practices, I’d sit in the very back of the risers, researching on my phone how to implement anal play into our repertoire. I blushed while I ordered a set of trainer butt plugs and anal-safe lubricants while Holden swam laps in the pool. 

In November, we received a message from another local couple who had also taken a few lifestyle vacations before diving in at home. They billed themselves as classy professionals, with some faceless photos of the female in black lacy lingerie. The messages they sent sounded “normal,” and we seemed to have things in common…kids, socioeconomic status, education. Would we be interested in meeting up for drinks to discuss more? Jack and I were eager for interaction…er, action? We all agreed on a date.

At the restaurant, seated across from them in a booth, we sized each other up. Raquel was stunning — friendly smile, gorgeous hair, toned body. She was very feminine, more Jack’s type than mine, but her confidence and sex-positivity were an immediate turn on for me. I like it when women slightly older than me take the lead. Hell, I like it when anyone takes the lead… 

Hal was a nice-enough looking guy, though not entirely my type. I’m spoiled, you see…Jack’s dad bod had melted away once he adopted my no-sugar diet, leaving him cut and trim. Though he’s slowly transitioning into a silver fox, there is still plenty of thick, brown hair on his head to offset his still-stunning blue eyes. He easily looks ten years younger than his actual age. 

Meanwhile, Hal was stockier — not fat, but not slim either, and something about his mannerisms reminded me of someone ten years older than his disclosed age. He spent much of that first dinner with his eyes locked on me, smiling, leaning in whenever I spoke. I found myself flattered, but averted his gaze in favor of the eye candy that both Raquel and Jack provided me with. 

No one is perfect, I reminded myself. I didn’t want to be shallow. Hal and Raquel were both attractive by all conventional standards, and they were easy to talk to. We chatted for hours that first night, our nerves dissipating just enough over drinks to detail our limited experiences and our desires, but not so much that the aura of tension ever left the air. 

Talking openly about sex with people in all its intimate, raw glory was refreshing and arousing, but, looking back, I think any chemistry I felt on that first night was misplaced. Simply put, we were more aroused by the situation than the people.

To that point, Jack and I went home and fucked each other’s brains out. When Hal texted to ask us out for a second date, suggesting that we book a hotel room “just in case,” we eagerly accepted. We wanted a notch on our belts; we wanted an experience. They seemed like a good enough match.

Well, that was silly. We wrote on our Kasidie profile that we had wanted friends to have sex with, not just random hookups. And yet, here we were, essentially agreeing to…a random hookup. 

We justified our actions by telling ourselves that this was safer — no deep feelings means no hurt feelings, right? They weren’t going to “out” us — it was clear they just wanted a discreet sexual encounter. They’d told us sex stories and assured us that they were STI-free, but we didn’t even know their last names. 

Plus, they were experienced, and we had no clue what we were doing. We decided to let them lead, and, oh boy, would we learn.

Our second date occurred the week between Christmas and New Year’s. We met for drinks again, sipping just enough red wine to make it to the hotel next door safely, then drinking just enough more to remove our clothes and proceed with our first official swinger experience. 

It began with Raquel and I kissing each other. Her face and lips were soft. She tasted sweet. Her breasts were soft and her nipples hardened under my touch. The men watched us, sipping on the last of their wine. Jack said later that he would have been happy to watch us for that entire night. In fact, he and I both hoped that the girl-on-girl would make up the bulk of our playtime. We’d made it clear that this was our thing, but, as we came to realize, this wasn’t theirs. 

Hal and Raquel were the first of many couples who would agree to our boundaries ahead of time, only to brush them aside later. Time and again, we would meet a couple under the terms of seeking intimacy between me and the female, only for the male to swoop in and want me for himself. 

Meanwhile, the female isn’t really bisexual — she’s bicurious, or simply willing to put up with some light lesbian action at the beginning to arouse the guys — gay for the gaze. The females see Jack as the charming hunk of a nice guy that he is, and they want his attention, not mine. 

 I wanted more with Raquel. I wanted to move from our positions sitting upright on the bed to a lying position, where I could see her body spread naked from head to toe. I wanted her to take off her panties for me and show me how she liked to be touched. I wanted to feel her from the inside and see how she responded. I could have spent hours exploring her body, but Hal interrupted us too soon, asking if he could massage me. I relented, letting them lead, but perhaps I should’ve spoken up.

His hands were strong, so that was nice. I watched as Jack began to massage Raquel, on the other bed, admiring how classically beautiful they looked together. 

Then Hal suddenly swooped in and kissed me on the lips. 

I lurched back. I shook my head slightly at Jack, who raised his eyebrows as if to ask, need help?

“I know, no kissing,” Hal whispered, his voice more gravelly than before. We’d texted our boundaries before this date — namely, I didn’t want anything to do with Hal’s mouth or penis. We worded it a touch nicer, but it seems I should have been more blunt. 

I just nodded and turned my head, allowing him to kiss my neck instead. 

I wasn’t at all attracted to Hal, I suddenly realized, but my body could respond nonetheless. It was as if I was a dancer with a new partner taking the lead. It didn’t mean anything that I could execute the moves, except that I had experience with the steps. It didn’t mean that I actually liked this new partner. 

 We repositioned, laying down alongside each other. One of his hands ventured downwards and began rubbing my clit and labia. He grabbed both my wrists with his other hand and pulled my arms up over my head. “You like it like that, don’t you?” 

I do enjoy being restrained, and my vagina grew wetter in response, but I didn’t like him saying that. As he maneuvered down there, I couldn’t help comparing. Hal’s touch wasn’t like Jack’s. I wondered if I would get to touch Raquel again, especially in the way that Jack was now stroking her below the waist. Hal’s body felt big and puffy next to mine, nothing like Jack’s fit physique, nothing like Raquel’s slim, soft curves. I was annoyed.

“Let’s trade again,” someone else suggested, and we went back to our own spouses. Jack performed cunnilingus on me and then fingered me until I orgasmed in squirts and fits. I let myself go, perhaps to prove that I wasn’t a prude, perhaps to bulk up Jack’s pride at his prowess.

Hal fucked Raquel on the other bed, alternating positions frequently until we heard him erupt in his own orgasm. The two of them lay there for only a few moments before they got up and headed to the bathroom, gathering their clothes.

Raquel leaned over and whispered to us, “You can stay here and finish. We have to get home to our kids.”

Jack and I exchanged glances. So they just felt us up, fucked, and now they’re rushing out? 

For a moment I wondered if Hal was remorseful over violating our boundaries. 

Then I realized that it was more likely that his pride had been hurt by my rebuke. It was clear I didn’t desire him. My interest in his wife was obvious, but he didn’t like that. He didn’t really want to watch two women, nor did he want to watch me orgasm repeatedly at the hands of my husband. He wanted me for himself, and he was willing to let his wife be with Jack in exchange for that.

Hal was the type who would agree to anything to get me in bed. He’d probably hoped that I’d come around to him once the action started, and now he was irritated that he wasn’t the stud his swinger status would proport him to be.

I didn’t call him out on any of this, of course. It’s not how we do things here in the Midwest. We all said goodbye in a perfectly polite way, and then we never saw them again.

There had been no chemistry. No elation, no feelings of connection, nothing sweeping me off my feet. There was no passion, no primal urges kicking in that made me lose myself completely in the moment, the way I do with Jack. I briefly wondered if this was just how sex with other people would always be.

And then I remembered Ryan and Lauren at that Couples resort the year before, and the sexual tension that wafted through the air as we chatted and got the giggles. I remembered the chemistry we’d once shared with Kyle and Janie when we were young. The feeling that, with someone like them, it would be playing. 

That’s what it’s supposed to be like, right? Friends care about each other and try hard to respect everyone’s boundaries and feelings. We wanted friends, with benefits. Friends, with open dialogue around sex. Friends, who found each other all attractive and interesting and comfortable. Friends, who sometimes did fun kinky things together. Friends, who showed each other how to make their wives squirt.

When I thought about that stuff, I got excited. I felt the tingles of titillation shooting through my veins like a drug. Surely these feels would make for a fun evening of play, without any awkwardness the next morning. In fact, I would expect the innuendos to continue over brunch in the most congenial way. The trick would be finding the right friends for this activity.

When I had thought about the possibilities with Hal and Raquel, I hadn’t felt those same tingles. In hindsight, I felt a nervous tension akin to prepping for a performance. I wanted to complete the task and do it well, but I wasn’t elated about it. I was determined. It’s not the same type of arousal, is it?

We weren’t giving up on the lifestyle. We booked another trip to Hedo for that coming summer. We updated our profile on Kasidie to be more specific about our desires. We chatted with other couples on the site, and we started discussing our wants and needs in terms of relationships rather than just sexual mechanics.

We weren’t rushing. After all, Jack and I had each other. Anything more would just be a bonus.