Did you ever play “Never Have I Ever” in college? Here are the rules: Everyone puts up ten fingers, and you go around in a circle and one by one share something that you’ve never done (and as human nature goes, the experiences shared are usually sexual). If you’ve done it, you have to put one finger down, and of course, drink. The first person to put all 10 fingers down loses or wins, depending on how you look at it.
One day we all have to become grown-ups, but that doesn’t mean we have to stop playing Never Have I Ever, or better yet — checking things off your bucket list. AskMen is still playing, and the rules are simple: In each edition of this column, we speak to a couple about something they’ve always wanted to try in bed. They tell us about the fantasy, and why it turns them on. Then, they actually do it, and we get the lowdown on how the experience matched the fantasy.
Caroline enjoys a successful career in New York City’s music industry, but up until recently, there was one unaccomplished mission in her life, and that was swinging. What is swinging exactly? It’s a type of group sex, but the term “group sex” is like candy: it’s an umbrella term for all sorts of flavors. An orgy is group sex with many people of any gender involved. A gang bang typically refers to one woman having sex with more than two men. We all know what a threesome is, and swinging is when two couples meet, swap partners, and then usually finish off the night by having sex with one another. If that sounds hot to you, you’re not alone.
Caroline is polyamorous, meaning that within her romantic partnerships, she both dates and sleeps with more than one person. However, despite her open-minded relationship format, and living in an open-minded city riddled with sex clubs, it took her a while to fulfill her swinging fantasy. That is, until she began dating her current primary partner, and decided to casually bring it up on a Netflix and Chill-themed Valentine’s Day. Her partner agreed, and they began investigating the New York City swinging scene and creating swinger profiles on dating apps. They successfully met up with and slept with another couple on Feeld, formerly known as 3nder, a hook-up app designed to help facilitate group sex (and apparently it works). Since then, Caroline and her partner have enjoyed many more swinging nights. But wait, there’s more: Her first swinging experience was also the first time she hooked up with another woman. Did she get jealous seeing her partner have sex with someone else in front of her, or was it just hot as hell? Keep reading to find out.
AskMen: Will you tell me about your fantasy you had been wanting to try? What was it, and what about it appealed to you?
I’ve been an exhibitionist and a voyeur as far back as I can remember, so watching and being watched has always appealed to me on an intellectual level. I’d wanted to try group sex for a long time because it appeals to both those things; plus being overstimulated, given tons of attention, and having a multitude of fun bodies and distractions seemed like the holy grail of fucking.
What kept you (until now) from trying it?
I hadn’t had the right partner(s) who would be willing to experiment in that way. I’m in a poly relationship where we date and sleep with other people separately, so it seemed like a natural progression to try dating other people together. My partner is much more willing and curious to try new things and I feel more comfortable and supported because of it.
You mentioned that you and your partner swing — how do you meet the other couples?
Primarily Feeld, and a few from Tinder and OkCupid. I love online dating for all relationship structures because it allows me to get a sense for people’s personalities and values before meeting up. One couple we date is an ex of mine who was into cuckolding. I thought his girlfriend was cute, so I suggested we all go out and I’m glad my gut instinct was right because it’s some of the most fun sex I’ve ever had. We’ve never picked up another couple at a bar, but that is definitely a goal.
What do you think it is about your current partnership that led you two to try it? Was it trust, love, and communication — all that one would want in a relationship?
All of those things! Feeling supported and loved creates space for experimentation. It’s easier for me to be vulnerable when all those cards are in my deck. Since my partner doesn’t experience jealousy, he encourages me to be sexually free at every opportunity, and this includes exploring my queerness much more.
What sort of talks did you guys have before deciding to try it?
It was pretty cute. On Valentine’s Day this year we got really stoned and were having a “Netflix and chill” kind of night, and I point blank was like, “How would you feel about having group sex?” There was a lot of giggling, and downloading of Feeld, and talking about different scenarios that would be hot vs tolerable, and downright bad. We were super nervous to go on our first date from Feel’d back in February but I’m so glad we did; it was an awesome experience.
Will you tell me about swinging? What was it like the first time you played with another couple?â€¨
The thing that’s really special about swinging/swapping is experiencing the love and chemistry between others and sharing ours with others in return. It’s super hot to hook up with someone else, get them off, then finish with your (fluid bonded) partner. Just an endless sea of intimacy.
Did you feel any jealousy watching your partner sleep with someone else in front of you, or was it all hot hot hot?
All hot, no jealousy. There’s more anticipation building when more people are involved I think, so after my partner and I have fucked everyone else in the room and we get each other last, there’s this really intense build up.
And of course, I must ask, how was hooking up with another woman for the first time?
Women are amazing! I wish I hadn’t waited so long. Really tender and intuitive and soft and fun and bouncy, like meeeee.