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A Deeply Honest Conversation with a Veteran Swinger

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Daniel Stern, swinging veteran, recently authored Swingland: Between the Sheets of the Secretive, Sometimes Messy, but Always Adventurous Swinging Lifestyle, which is now available for purchase. I sat down with Daniel to chat about one of the most notorious and misunderstood subcultures, the rules of the Lifestyle, and how he arrived at his sexual peak. Just, please, don’t confuse him for that robber from Home Alone.

What compelled you to get into the Lifestyle?
Well, I actually didn’t know there was such a thing as the Lifestyle at first. What I knew is that I sucked at sex. So I wanted to get better at it. All the sex I had through my mid to late 20s had always been in long term relationships. The way I operate is there are a lot of emotional entanglements that it involves. It was sort precluding me from getting better just at the physical act of sex. I set out to have what I termed “sexual batting practice”.

I had my first NSA sex and then at a small gathering someone mentioned “the Lifestyle”. They described what it was and they mentioned a site. I said, “Oh, that’s what I want. I want to go there.” I went to the site, created a profile. Once I started meeting the people and having the experiences, that was a match. There’s a saying that goes around the lifestyle, “You don’t choose the Lifestyle, the Lifestyle chooses you.” I don’t know empirically if that’s true, but it was true in my case.

What was your first experience swinging like?
I had been searching for casual sex online for six months, getting nothing but flat out rejections or no responses or spam. Then a Craigslist ad just wound its way through the bowels of the internet and I found this party being hosted for this woman. They were looking for guys and the theme of it was rough sex. The logical part of my brain said, “Hell no, don’t go near that.” But the desperate, emotional part of me said, “You haven’t gotten anything, you have to take what you can get.” I did what’s called a voice verification, which is when you’re making contact over the internet and they like what they see in your email. They call you to make sure you’re a legitimate person. The conclusion that they came to after verification was that I didn’t sound too crazy, which basically means, “You’re invited.”

How’s that first conversation go? Is it sort of like a first date or more straight to the point?
The conversation is really like the fourth stage. Because it goes from email, to instant message, to call, to meet and greet, to play. So by the time you get to the phone call, you’ve been through a lot of information. What do you like, what do you not like, what are your limits, what are you looking for, what are your bad experiences? You’ve gotten that out of the way. The phone call is more about finding out if the chemistry you’re having online is translating into a conversation. You’re just getting a gut feel for what the other person is like.

You’re also making sure the other person is claiming to be the person they’ve been saying they are. As one woman said, “There are guys in this lifestyle who are masters of Photoshop like you won’t believe.” People will often put up a photo where they are twenty years younger and have half a head more hair. If someone doesn’t look like their picture, you’re thinking, “If you’re lying about this, what else have you been lying about?”

Have you ever met up with someone and they were completely not the person who they put out there?
I wouldn’t say it was completely not the person. It’s never that extreme. But there are cases when their pictures were certainly younger and it was before they went on a big, gorging diet. They were just gaining weight. There was a situation with a female and there was a party I was invited to. She was looking to go to a party, so we met up. She didn’t have a gut in the picture, her jowls weren’t as affected by gravity. When you show up and you smell like you just came from the gym, it’s not the best impression. More often it’s single guys who are lying, because they’re just so desperate for anything that they will try anything to meet up. To me it doesn’t make sense, because if you show up and you’re not who you say you are, you’re going to get turned down. I guess they’re hoping if they play the numbers, one of them will say, “Oh, fuck it. Let’s just go play.”

Have you ever showed up anywhere and someone got up and left?
Yes, it’s not like someone has ever bolted for the door, but at meet and greets once you get about 15 minutes in after a bit of a talk, I’ll excuse myself to the bathroom for a few reasons. If I’m meeting a single female, odds are she’s told a friend she’s meeting a guy. She’s going to check in at a certain time. I want to give her the opportunity for that. If it’s a couple, sometimes couples have developed hand signals or trigger words to let the other know what they think. But usually I leave for three minutes and let them have a talk. It also lets me get my thoughts straight. Sometimes you get back and the person says, “Hey I don’t think we have the chemistry,” which is totally cool. I’d rather do it then than four hours later.

What would you say is your general batting average. Your meet-up to actual play ratio?
My percentage is pretty indicative of everyone because when you get to this point, you’re 90% sure you’re going to play. It’s sort of last minute stuff. I’d say over 90%. More times than not, the rejection you get is right in the beginning or right before the phone call. Sometimes they’re fakes and just want the connection online for no reason.

What would you say you’re most attracted to when you look to swing, especially in a couple?
First and foremost, they have to be in a good place in their relationship. If I see that they’re looking to save their relationship, I run for the hills. I find that the lifestyle accentuates. So if you have a wonderful, solid marriage, it will accentuate that. If you have a troubled marriage, it will exacerbate it and push it closer to divorce. I don’t want to be any part of that. I want to make sure there’s a good foundation in their relationship. Normally they’re saying they want to try something new and spice things up. After that, I want to make sure they have a good sense of humor and they’re not rushing things. If they’re rushing things, it’s not going to turn out well in the Lifestyle.

I’ve played with some couples after a week of contact and others after 3 or 4 years. It just takes whatever it takes. You want playful people who like life. Basically, what you would want in a friend. Of course, there’s physical components, too. I’m personally not attracted to BBWs, which are big beautiful women. That’s just my taste. I’m also not into the BDSM scene, it just doesn’t spark for me.

Do you play with men at all?
Yeah, no, I’m a boring straight male. I’ve been approached by guys and I’ve been approached by couples with a bisexual husband, and I’m very flattered. I’m sorry, but men are just the uglier of the genders.

If you can single out one experience, what was the best evening of being in the Lifestyle?
I don’t know if I can name one because they’re all different. A newbie couple: I was their first experience and we’re still friends six years later. There was a couple who turned out the husband had a form of Aspberger’s and he had trouble with being overstimulated. But as I was playing with his wife, he felt comfortable enough to join in. I enjoyed being able to facilitate that experience. I can’t really say there is one because they all are unique.

Okay, what about your worst experience?
One was that woman who had the jowls, the gut, and the body odor. She was just rude.

But you still went through with it!
We were going to a party. So we got to the party and she didn’t mention she had a drinking problem. So, she ended up snoring on a stool for a while, so we just left her there. She was also really reclusive, so I eventually had to get her out of there. Then the other worst one was I was playing with a couple and the wife was giving her husband a blowjob and he just fell asleep. I said, “Thank you very much. I’m out of here.”  That marriage was about to implode.

So, the Lifestyle gives you the thickest skin you could possibly get from any sexual experience?
Yeah, I think the line in my book is something along the lines, “In the Lifestyle you need the thickest of skins and a Chicago Cub’s hand’s constitution.”

Haha. What’s your limit?
Safe sex. If someone won’t use condoms, I won’t sleep with them. The standard line is also no children, no farm animals, and nothing toilet related.

So, it seems like you’ve kept up a long term relationship with some of the people you swing with. Have you ever begun to develop feelings and thought, “Hey, maybe I’m falling for someone in the Lifestyle”?
No, it’s never gone that far. Only dear friends. I don’t know if there have been any women who have felt that way about me, but I’ve always been very upfront. It makes it easier when the majority of swingers you’re playing with come from couples. You already know where the boundaries are. I’m not there to blow up a relationship or destroy anyone’s life.

Are you at all opposed to relationships? You’ve been doing this for about ten years.
I’ve had a few flings, but the difference is that going through all this and seeing all these couples, it’s made me be more open to relationships. I’ve never been one to seek one out. I’ve never been someone to say, “God, I need a girlfriend.” If it presents itself, great, but I’m not on all these Match.com sites. I’m definitely more open and ready for it since I’ve slayed the dragon of poor sexual performance. You know, stop hitting on me, okay, Kate?

I’m sorry. I know. I was searching for you on Match.com earlier. So, would you disclose your lifestyle to someone or ask them to become a part of it if you started a romantic relationship?
I don’t see it as something I have to disclose right away, because I don’t know if the relationship is going anywhere. Of course, it’s not something you should wait to tell five years down the road. If things were getting serious, I’d introduce the topic. It’s really nice that I can say, “Hey, read this book and tell me what you think.”

That is pretty nice. In terms of the book, do you disclose that to people you’re playing with now?
Yeah, I’ve told people I’ve played with.  I’ve always been me being me. I changed all the names in my book. I’m never going to talk about the who, only the what.

When was the last time you played?
About a year ago. I’m still very active in the friendships. But it’s a very exhausting life. I was leading two separate lives and trying to keep them straight. I’m definitely not still playing to the degree I was at the climax of my book. As you know, as you get older your body can’t do certain things.

Well, I don’t know yet, but I don’t look forward to it. What was your main reason for writing this book?
I wanted to better the community that was so good to me. It’s really my love letter to the Lifestyle. If I’m going to direct people to the Lifestyle, I’m going to do it responsibly.

What’s the biggest misconception about the Lifestyle that you would want to impart upon the world?
That it’s not this secret society of deviants who shtupp anything with a pulse. It’s not this bacchanalian festival going on. It’s adult match-making. If you look at it that way, then you’ll understand it. I have this theory that everybody knows somebody who has participated in some respect in the lifestyle, they just don’t know it.

This article originally ran in Nerve’s Storytime series.