Converting a Vanilla to the Swinging Lifestyle


Converting a Vanilla to the Swinging LifestyleMr. Doubleplay and I are friends with a very sexy single lady. She’s beautiful. Loads of fun. We talk about sex a lot. She complains to me that she hasn’t been laid in over six months. She doesn’t want a relationship but needs a good fuck. I almost fell off my chair when she said that. My resolve about never revealing my super-secret Swinger identity within my vanilla world started to waver.

Remember, this is a small town with about one degree of separation between acquaintances. If the proposition goes wrong, I could lose a good friend. And half the town would know what happened.

But this gal is possibly worth the risk. And some not so innocent flirting has tested the waters. To some of it, she has responded well. To other instances she has responded with an “Ewww.” Very mixed messages.

Mr. Doubleplay thinks that if we do decide to proposition her, it should be me alone who makes the proposition and we pose as first timers ourselves. “We’ve always had this fantasy….” Could you be the one? That way we are not revealing all of our secrets. I’m not sure if I can do it though. Risky business.

We are friends with two swinger couples who have shared their experiences with converting the vanilla. For one couple, it did not go so well. The ladies were friends from college. They had flirted with one another for years. The couple went to visit the college friend and her husband. The girls ended up getting it on in the bedroom. The problem is that our friends did not realize that the other couple had not fully talked it out on their end. It was their first experience and they weren’t quite ready. That relationship is awkward these days. It may never recover, actually.

At Desire, we met another couple who got started in the lifestyle by having threesomes with her girlfriends. The lady in this relationship is a carefree soul. Very loving, very open, and likes to keep life light and fun. I think that attitude with her friends helped to keep the threesome propositioning fun and lighthearted as well.

So I end this blog asking for advice. Is it worth it to try to convert the vanilla? And if so, how does one do so without blowing a relationship?


Mrs. Doubleplay is 40-something mom living in the middle of America with kids, a career, and pretty house in the suburbs. She’s active in her local church, coaches the kids’ soccer games, and happens to have a secret life as a swinger. Married to her high school sweetheart, Mr. Doubleplay, the couple dipped their toes in the lifestyle for a couple of years but then dropped off the radar to have kids. They rejoined the lifestyle in 2005 and haven’t looked back. They have been soft swap from the start but are working their way toward greater forms of adventure as we meet hot couples on lifestyle vacations, swinger clubs, and online websites.


  1. Ah this one is very difficult to understand.

    The revirberations can be extreme if you misunderstand the signals that the vanella is sending out. They may not even be aware that they are broadcasting an incorrect message of their desires or intentions.  Ask congressman Weinner.  LOL  could not resist that jab congressman.  

    Hubby and I were 30 when we got the itch and being bi for several years I had several GF.  Like me the GF had guys that were horn dogs wanting to try the lifestyle so that was our entry. Three couples at a motel for the weekend.  A room with a king bed with a connecting door to a room with two queens–beds that is, a well stocked bar and a few dozen joints.  Hey Dude!

    We’ve had very few encounters with introducing vanillas.  They are about as rare as the unicorns. Most of are encounters have been with people we met at a club, house parties, or hotel meet and greets, or family reunions.  OK, just joking about the family reunions.  LOL

    One of my half sisters has brought home GFs to play with her and her hubby. Sis has a radar for corectly picking up those signals. That may be the secret

  2. Evolving Wife on

    Eek. That’s a big risk, I don’t know that I would take it. I’ve seen too many friendships and relationships going sour lately. I would excercise caution.

  3. Not blow the relationship…?  Choose to not be dishonest with an intimate, least of all a good friend.  And certainly not as a ploy to get into her pants.  Come up on to her truthfully, if you choose to do it.

    As a unicorn, I gotta add that honesty here comes with some excellent selling points. “We’ve done this before.  We’re not going to be fumbling awkward noobs, and we know how to make it great for YOU. No worries about stirring up any drama between the Doubleplays or in our relationship with you which we really quite value.”

    Keep in mind that wanting a good fuck is not the same as wanting to be fucked by two people, let alone one that may or may not be of her orientation.  So I’d start by inquiring first for more sense of what she’s craving.

  4. Without blowing your cover, next time she mentions something about f-ing without a relationship, you might ask if she ever thought about  a threesome or….  

    Another possibility may be to let her and your hubby have a romp in the sack..  But this may not be something she, you, or hubby would be comfortable with…. 

  5. Also a guage of her inhibitions might be a light discussion of her activity history. Like during high school, college.  Bi curiouity?  This also brings up the issue of how much of your own history do you want to share.  Some are very open about such, others not.    i think the more uninhibbited her sexual history the more open she may be to trying it. 

    but as evolving wife said that can be a big risk.

    Keep us posted with the results of your eforts in this area.

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