Ask Professor Foxy: How Do We Have A Threesome?

This week-end column “Ask Professor Foxy” will regularly contain sexually explicit material. This material is likely not safe for work viewing. The title of the column will include the major topic of the post, so please read the topic when deciding whether or not to read the entire column.

Dear Professor Foxy –

I am a mid-20’s woman in a monogamous relationship with a man of the same age. We’ve been dating for almost five years, and we have a great relationship and a good sex life. I am confident that we have a lifetime together ahead of us. However, ever since my early 20’s, I’ve been really interested in fooling around with another woman. I’m not questioning my bisexuality or anything – in fact, I’m not very interested in those kinds of labels, that’s not what this is about.

I think that the desire has been growing stronger lately. I find myself fantasizing about it, and getting extremely turned on, and I’d really like to try a threesome with my boyfriend and another woman. I’ve talked to him about it, and he’s interested, but cautious. He had a threesome with an ex-girlfriend and one of her friends, and in the end, it destroyed the friendship between the two girls because of his girlfriend’s jealousy. I’m not a jealous person at all, and he knows that. And besides, I’m not interested in inviting one of my friends to join us sexually; for one thing, none of my girlfriends are bisexual, and even if they were, I would be much more interested in meeting someone new and inviting her home with us.

He and I have talked about how it would work; I figure I’d like to meet someone online, being entirely honest and open about what we’re looking for (a casual encounter with another woman), chat with her for a bit, then maybe go out for dinner once or twice to see how we all get along, and if the vibe feels right, we’ll invite her back to our place. I have no desire to rush into anything; if it takes years to get to the point where both he and I feel comfortable enough with someone, so be it. I wouldn’t want to sacrifice anything I have with him over a sexual fantasy. So if we never even meet the right person, then whatever, I’m not going to get broken up about it. The point is, though, that I think we’re at a point where we are mature enough to handle it, both individually and as a couple. He is less convinced. He is jaded by his first experience, and he doesn’t want to threaten our relationship with something like this, because he and I really love each other and of course I am glad that he cares about us enough to want to avoid any pain.

The thing is, he’s definitely turned on by the idea of having a threesome with me and another woman, he’s just placing his respect for our relationship above his sexual desire (which, of course, is fantastic). And since he is so cautious about it, I’m not at all interested in pressuring him or convincing him or trying to change his mind; because I know that if he only does something like this begrudgingly, then it will become a threat to our relationship. So I’m not asking if there’s any way I can convince him; I believe that this can only happen if he comes to the conclusion independently that we can handle it, just like I did. I can wait until that day comes. So here is my question: Is there any way we can sort of work our way up to it? Like, rather than diving right into a full-out threesome, are there little games we can play or activities we can try, just he and I, to sort of test the waters? Something that will help us decide if we are truly ready, so that we can turn away before we get too deeply involved. I want as easy a transition as possible, so that at any point if one of us is feeling uncomfortable we can just turn it around. Should we go to a swingers party or something, just to feel the vibe in the air, before we have any plans to take someone home? I wouldn’t even know where to go about finding a swingers party.

So that is part two of my question: I’m also wondering if you have any suggestions on how we can meet a partner like this. Are there any dating websites devoted to this sort of thing? I’ve seen some Craigslist “casual encounters” postings related to this stuff, but is there anything more official out there, like a match.com just for sexually adventurous couples? Of course, if we meet someone online, we’ll be very careful, and ask all the right questions about STD tests and birth control etc etc, and take our time getting to know her first.

No Signature

Dear No Signature –

You can ramp up to the threesome, but can only do so much planning. You also have to be ready for the conversation(s) afterwards. How can you ramp up? There are a number of steps.

First step: figure out your boundaries as an individual and as a couple. You’ve already made it clear that it won’t be a friend. What else matters? What does safe sex look like? Condoms, dental dams for oral? Is anything off limits? Are there any sexual or intimate acts you want to reserve for just the two of you? Can she sleep over afterwards? Can she sleep in the same bed? Work these things out beforehand. Keep in mind, I am not saying you will care about all of them, but work out agreements about what you do care about.

Second step, fantasize about it together. Talk dirty during sex or while making out. Describe the other woman being in bed, what you would do to each other, what he would do, how it would feel to watch. Now, really, how does it feel? Still hot? Still feeling good?
No jealousy is not the goal. Jealousy is normal and it happens. Working through it is a good thing. You will learn how to reassure each other. Plan ahead: is there something you two like to do together? Eating out? Hiking? Movies? Be ready to do that the next day.

I would start with craigslist or nerve.com. You are not necessarily looking to become swingers, so start with what you actually want. Sit down together and write an ad. What are you looking for? Be explicit. How would you describe yourself? Him? Sort through the ads together – is this turning both of you on? Does it work?

When you find someone interesting, meet them out. See what develops. There is only so much planning one can do: at a certain point, you just gotta go for it.

Best,

Professor Foxy

If you have a question for Professor Foxy, send it to ProfessorFoxyATfeministingDOTcom.