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Q. I've been swinging on and off for years as a single guy. Just over a year ago I met a woman who's kinky and pretty open minded and into trying BDSM. I hoped that I could draw her into swinging but she's very reticent about getting started despite her wanting us both to try some bi fun. My best efforts in making her feel secure in our relationship don't seem to be working as she still struggles with taking that first step. I'm finding it frustrating because I'm missing the lifestyle but don't want to ruin what we have now.
Any ideas on how to introduce her gently?
Rob
A. Rob, you need to figure out where her concerns lie with the lifestyle. It's possible she may not be comfortable with it in principle, and it's also possible she may never get to a point where she is comfortable with any level of ethical non-monogamy. BDSM, kink, and open-mindedness don't always go hand in hand with non-monogamy. That said, an open-minded and kinky person may be willing to push her own boundaries far more so than a vanilla person.
Where I would start is with fantasy play. But be up front with her, tell her you want to introduce a little non-monogamous roleplaying into your relationship to see how she feels about it. Make sure she knows that she can halt the play at any time. As hard as this may be for you to do, you must cede full control over the stopping and starting of any type of non-monogamy play, both real and hypothetical to her.
You're used to, as a single male, being the captain of your own destiny in the lifestyle. (Though, likely, having to bow to the whims of the hedonism gods due to the fact that you were a single male, sorry about that…) This will be all about relinquishing control. Once you get her confident that if she ever doesn't like something she can shut it down, then you'll be able to really play with her boundaries. The big card here that will push things in the non-monogamy direction will be her bi-curiosities. This is something that can only be achieved through non-monogamy, and will therefore push you into the edge of non-monogamy. Remember though, the competition for unicorns is insane, and the danger of playing with someone who's a friend can be difficult as well.
Ironically, your best move for a gentle introduction would be with a couple that you can have MGS (Monogamous Group Sex) with, that way you're expanding the comfort zone with another couple in the room, you're giving the girls the opportunity to connect if they chose to (they very well may not) and it's an excellent thing to talk about later. “Did you like this?” “Wasn't it hot when–” etc.
As with the last advice column, and many before, communication here will be the difference between success and failure regardless of the direction you move. Please do update us, or continue the conversation in the comments below.
Good luck!