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How We Became Swingers

The morning everything changed.

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Golden morning light was streaming in through the windows but I was still asleep. And my wife was sitting at the foot of the bed, drinking her coffee, watching me. My eyes opened to find her staring into them. “What the fuck?” Drinking her coffee while watching me sleep could be considered strange behavior — even for her. Something was going on.

“I want you to take some photos of me for my dating profile.”


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She then walked out of the room and went to work.

Our journey into non-monogamy began around five years ago, and it began typically — although I wouldn’t necessarily say it began well. Chaya and I were legitimately monogamous for the first seven years of our marriage. My transgressions amounted to one kiss, which is to say nothing. Having sex with other people was something that I thought about but was always something I kept to myself. But one night in the Philippines the thought struck me that I knew nothing of the sexual underbelly of the planet that I traveled — and that I, myself, was pretty vanilla.

Vanilla. Chaya had actually called me that once and it stuck. I knew it was true. How could I, world traveler / culture writer / author / big media journalist / filmmaker be vanilla? I began realizing that there was an entire world that I was not experiencing, that I knew nothing about, and I didn’t like the way that felt.

At that time I was traveling away from my wife regularly for work, sometimes on the other side of the world for months at a time … often in places where the availability of sex was near ubiquitous. I was writing for a major global financial publication and through the course of this work was regularly meeting and getting friendly with women who I felt I could have engaged sexually with. But I held back, didn’t yet make the connection that sex and understanding a place and culture were inseparable, and then one night in the Philippines the drive to find out proved stronger than the drive to be sensibly return to an empty hotel room alone.

I don’t do well with not having experiences. Dangle a carrot in front of me and I bite. I spent the previous twenty years before Covid-19 — from the time that I was 18 until 38 — traveling. I racked up 90 countries, and lived a life that was driving by the hunt for experience. I became a writer and filmmaker along the way, which gave this inherent drive a much needed financial incentive.

But I thought that that experience in the Philippines would be a one and done type of endeavor. Tried that, it was fun, I’m done. But I was wrong. Instead it flipped a switch in my head that remained dormant for seven years. Suddenly, the prospect of a new sexual experience lit my mind up, synapses firing everywhere, and the urges became impossible to resist. Two core forces aligned: curiosity — the need to push beneath the surface of the places I was traveling in — and sex. I felt somehow reconfigured, and I couldn’t understand what was happening — for over a decade I walked right by potential sexual experiences without so much as an afterthought or regret; now it felt like I couldn’t do it. My legs would lead and my mind would follow. I believe, for the first time in my life, I was getting a taste of what addiction is like.

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But I didn’t initially tell my wife. I’m not sure why. I imagine cowardice had something to do with it, but also the fact that I thought I could beat it. While I cheated on every girlfriend I’ve ever had up until my wife, for the first seven years of our marriage I was basically strong. Then I began breaking down … every experience I’d declare as my last … until the next experience.

I did little to hide what I was doing. I would hint at it, I would joke about it, and Chaya would too. I knew she knew what was going on — what person spends months away from their partner in places where sex is easy to find and doesn’t transgress? —but as it wasn’t confirmed it wasn’t an issue. Somewhere down deep I wanted to be caught, and when I was it came as a relief — like a crook on the run who finally gets apprehended.

Then the real work began.


We tried to go the conventional route at first. She told me not to cheat, I said I wouldn’t — and meant it — but on the next work trip away it would start all over again. Something clearly wasn’t working; I’d opened something that I was having a hard time closing, and thought there was something wrong with me and needed some help.

So we went to marriage counseling. I believe my wife thought that I was going to be berated and shamed and she was going to be somehow vindicated. That didn’t happen. Rather, the counselor was supportive of other strategies. At that time we didn’t know how typical we were.

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Nobody really knows how prevalent cheating is as it’s something that people tend to lie about, but estimates range from 30% to 70% of marriages experience infidelity and some research pegs the percentage of people who admit to cheating at around 50%, irrespective of gender. What is clear is that we were normal, and this in and of itself was a little hard to swallow. We both praised ourselves on how alternatively we lived, how progressive we were, and how we did things our way. We had our first kid when we were in our 20s and we just put her in a backpack and kept right on traveling. She spent her first years in Central America, Mexico, and China; some of her first words were in Spanish and she eventually became a native Mandarin speaker. But now we had fallen into the same pitfall of, statistically speaking, almost every other couple on the planet.

The counselor had seen this before, and knew that brow-beating me and trying to cram me back into the monogamous mold where I would live a life of quiet desperation was foolish. Instead, he was surprisingly supportive of us moving towards a more equitable, open, honest relationship — a relationship where we would sexually advance with other people, together. I remember him asking me how I would feel about my wife being with another man, and I could not check the smile that spread across my face. “That’s exactly what he wants,” my wife exclaimed with a laugh.

It was.

I’ve always liked the idea of my wife fucking other dudes. I would often fantasize about it while we were having sex — the image initially put in my mind by a rather traumatic experience at the Syrian border many years before. When walking through city streets, hanging out in airports, or drinking in bars I would often entertain myself by imagining a particular dude (or two, or three …) that we’d see putting their cocks in my wife. This began happening long before I broke the ice in the Philippines … but like that event in the Philippines I never mentioned it — it wasn’t that it was taboo, it was that I didn’t fully understand it. Why did the thought of another man sexually pleasing my wife turn me on?

At that time I didn’t have many direct references through which to frame the desires that I was having — We were predominately living in Asia outside the bounds of any kink communities, clubs, or even friends who were into progressive interpretations of sex and relationships. The lifestyle was something so remote and distant from us that we hardly even knew it existed. To us, swingers were 50-something year old cougars from the 70s hosting cocktail parties in their living rooms and fucking on shag rugs. I was so adrift I didn’t even know there were places to moor up to.

So I kept it to myself.

And this is what I really regret.

I don’t regret that experience in the Philippines. I don’t regret any of the dozens and dozens of incidents of infidelity. I feel bad for how they would come to make my wife feel, but I don’t regret them. What I regret is not having cultivated a close enough relationship with my wife that I could share my feelings with her. I regret how emotionally and psychologically closed off I was to her; how guarded I was. I think back on this now and I have no idea why I just wouldn’t tell her — I talk to her openly about everything now, and not just sex stuff, and it seems foreign to me that there was once a time — years and years — when I didn’t do this.

But things were different then. We were still in our first marriage.

We decided to give non-monogamy a chance. It was either that or separate — which would have been a dumb thing for two people who really liked each other and enjoy their time together to do. While we didn’t frame it like this at the time, what we needed to do was to start a second marriage … with each other.

Part of the problem with transitioning from a relationship with the expectation of monogamy to a more open, swinger style relationship is that we try to remold the parameters of the union that we’ve already created rather than burning it down and start building it again from the ground up. A non-monogamous partnership can not exist within the parameters of monogamy — this isn’t a matter of a simple substitution. No, everything must change or else the baggage of the previous relationship — the unrequited expectations, the lying, the feeling of being undervalued — will sink the ship. You need to mourn the previous relationship, get over it, and create something else that’s entirely new — new expectations, new outlooks, new ways of communicating.

We did not do this perfectly … it actually took us years to get over our first marriage. But when we did something new and beautiful opened up before us: imagine being in a relationship where you can tell your partner anything, where you can express your innermost desires, where you can be fully honest without fear of repercussion.

This is how monogamy is supposed to be, but isn’t.

Our non-monogamous life did not start out equitably. We were living abroad, had two young kids, and no babysitter, so going out to the clubs together at night was not an option. My wife was also deep in her AMI training in Prague and lacked much free time — the time she had she wanted to spend with our kids rather than going out to get fucked. So we entered into this interim period where I would go out and hook up with other people at clubs, parties, or privately and I would come home and tell her all about it. At that time this was a huge step forward — I had to rebuild trust and doing things that gave me the opportunity to be honest proved to be an effective way to do this.

Then we moved to New York City … and a few months later the Sars-Cov-2 pandemic hit … and we were locked down. It was a time where people were afraid to stand too close to each other in the streets, let alone meet up with strangers for an anonymous fuck. So our non-monogamous practice was put on hold.

But eventually some clubs began reopening and I began frequenting them. There were more the underground, edgy style of club — I assume many of them were either illegal or sat on the fringe of such. They were seedy; they were exciting … like going into deranged fictional lands that you only imagine in noir novels. But not really places my wife would want to go.

So we continued like that … But there was a limit as to how long that could go on for. There needs to be some degree of equitableness in an ENM partnership — if only one party is engaging the entire apparatus gets knocked out of balance. There are some people (mostly men) who enjoy that imbalance … but that’s something different than what we were doing.

So I encouraged her, I’d invite her to come each time I went out to a club or met up with a couple, but I didn’t push it. There were a few forces that seemed to be holding her back … common insecurity, the fact that she hadn’t dated in over a decade, as well as a feeling that if she did start hooking up with other people it would somehow vindicate my transgressions … bring her down to my level, so to speak.

Then we had this exchange:

“You just want me to fuck other people so you can have sex with other women.”

“But I’m already having sex with other women.”

There was nothing else to say.

At that time she didn’t really get my stag, cuckoldish proclivity. She didn’t get how arousing I found the thought of her taking another man’s cock was. She seemed to think I was bullshitting; scheming to find a way to put myself on even footing with her in our extramarital endeavors — just looking for a way to make it more okay for me to fuck other women.

She really, really didn’t get it.

“I want you to take some photos of me for my dating profile,” she said from the foot of our bed.

I was just startled out of a deep sleep by her sitting there just looking at me drinking her coffee. I have no idea how long she was sitting there, if she got the idea on a whim, or if she planned it out. All I could do was say okay … and smile. I was surprised. I felt excited. I felt that little tinge of insecurity and worry that makes such prospects so absolutely stimulating.

When she got home from work I took some photos of her and helped her pick out others. She asked what dating apps to use besides Tinder. I suggested Feeld. I watched as she assembled her profiles … She put them out there, closed the apps, and we went on to have an ordinary night.

Then the next day she opened them … and boom, found that she had hundreds of likes and dozens of messages. After a couple of days she asked me to guess how many swipe rights she had on Tinder — it was over a thousand — and she collected about as many on Feeld as well. The messages kept streaming in — random dudes telling her how beautiful she is. Granted, this is the experience of just about any women on those apps … but something about the deluge of attention seemed to make her feel good. She’d tell me how many new likes she got and ask me how many I got … haha, yeah.

I am going to say her that my wife is legitimately sexy. She is thin, she is curvy, she is petite with big Hasidic eyes and a sweet smile. She also knows how to emphasize her natural beauty … and just has this overtly sexual air about her. She likes to fuck, and throughout out marriage we have had sex just about every single day (literally).

But my wife has the tendency of undervaluing herself, and she seemed to think that she would go unnoticed on the apps or only the ugly dudes would be interested. She did not anticipate the fact that legions of attractive men wanted to take her out … and get her naked. I could see her confidence perk up a little … and two days later she was going out on a date with some hot guy who lived a couple of streets over.

While I’ve harbored fantasies of my wife fucking other men for many years it was still startling to me that it was actually going to happen. How I would take it I really didn’t know — was I really into it? Did I really want another cock inside her — the first one since we got together? Did I really not want to be her only one?

I have to admit that these were thoughts that I had but they were quickly overpowered by my excitement. She was going to meet someone she didn’t know, remove her clothes, and let him fuck her … The thought of that made me convulse in a rather pleasing way. It made me feel sexually aroused in way that I’ve never experienced before … and I found myself going through her lingerie drawer picking out what I wanted her to wear.

She was now standing at the door next to me, looking deep into my eyes. She was fully beautified — eye liner, lipstick, her hair was straightened, tight black jeans, a revealing top, and the lingerie that I picked out underneath. She hesitated before walking out, giving me one last chance to call it off. “You can still say no if you want to,” she said.

“I love you,” I said. “Have fun.”

With that she went out the door and down the stairs. I watched her go, mesmerized by how beautiful she looked … walking away from me.

We installed this family tracking app that allows us to know where we are before she went on the date. It was a safety measure … but also an erotic one as well. I could watch her meet him at the bar, leave the bar, go back to his building, go into his apartment, go into his bedroom. I couldn’t take my eyes off it the entire night, imagining what she was doing.

It really didn’t take her long. They met at a bar around the corner and only stayed for around 15 minutes before leaving for his place.

For the next two hours I kept imagining what was going on. I enjoyed the way that felt. I knew she was having sex with him and I just laid in bed thinking about it.

I then saw her little blue dot move on the app and begin moving up the street. She was coming home.

She walked through the door and into our bedroom. I was waiting for her. I grabbed her and we began kissing. I asked if they fucked; she said they did. I tore off her clothes and threw her onto the bed. I licked her freshly fucked little pussy and then put my cock inside her. I slowly fucked her as she told me everything that happened in graphic detail. She orgasmed for the third time that night. I came inside her, flipped her over, and began fucking her again, climaxing a second time without the need for a refractory period.

Yes, I liked it.

I really fucking liked it.

After that night something changed within me. I began feeling different towards my wife. I was suddenly consumed by this warmness towards her. I wanted to please her. I listened to her more deeply. I began doing whatever I could to make sure she was always comfortable. I respected her more.

This wasn’t a tit-for-tat, you did this for me so now I’m going to treat you better kind of thing. It was just a flip of a cerebral switch that made be feel and act differently. Now, I’ve always treated her rather well, but I suddenly became obsessed with her well-being. I started treating her everyday like someone who’s on a first date — I felt as if I was competing for her 24/7 and felt a constant drive to put forward my best self. I realized that she tends to get ornery when doing housework so I began doing all of it; I began diverting more money towards her and the family and away from my business; I began feeling the urge to spoil her with a constant stream of small gifts and surprise her with Uber Eats deliveries for lunch at least once a week — thoughtful things that I simply never really thought of doing before.

A switch was again flipped … only this time it was my wife who was igniting my synapses … like what used to happen when we first got together. I thought that this heightened degree of infatuation with my wife would eventually wear off, but years later it hasn’t. Imagine that feeling that you get when you first get with someone. I feel like that towards my wife everyday.

This new emotional and psychological attraction was something that I did not expect from the swinger life. I thought that we’d start having sex with other people


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Ender Wilder
Ender Wilderhttps://swingingsolution.com
Ender Wilder is a former big media journalist and author who escaped from that world to be able to write about anything he wants. He has been actively living the swinging life with his wife for many years, and is available to coach those who are just getting into the lifestyle or have hit some bumps along the road.



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