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  Note: In this section, we are mainly addressing couples thinking about having a threesome. For single people who want to join a couple in a threesome, most of this advice still works, but a lot more talking and consensus needs to happen within a couple, so we are focusing there.

  FOR COUPLES WHO ARE CONTEMPLATING ADDING A THIRD

  Quiz #1

  Are you and your partner ready for a threesome?

  Read each of the statements below and check the ones that apply to your relationship:

  We are committed to each other and secure in our relationship.

  We are open about our sexual fantasies and share them with each other.

  One or both of us fantasizes about asking another person to join us in a sexual encounter.

  Neither of us is a jealous person.

  We can both separate our loving relationship from sex.

  Experimenting sexually is very important to both of us.

  One or both of us is bisexual or bicurious.

  Both of us would enjoy seeing our partner being pleased by someone else.

  If we try something new sexually and it’s not great for one or both of us, we can get past it.

  We are both able to have sex without getting emotionally involved.

  If you and your partner checked off the first five statements, you’re receptive to the idea of a threesome. Each statement you checked off after the first five means you’re one step closer to deciding to have one. If you checked off all ten, you’re raring to go!

  Quiz #2:

  Who should not have a threesome?

  Read each of the statements below and check the ones that apply to your relationship:

  One or both of us is concerned that we’re just not wild enough in the bedroom.

  We are bored with our sex life and want to spice it up.

  One or both of us experienced a threesome before (with other partners) and wants to do it again.

  One or both of us is afraid we’ll cheat on our partner and we think this is a solution.

  One or both of us has a jealous personality type.

  I want to test my significant other to see if he or she will cheat on me if given the chance.

  We have trouble communicating about what each of us wants out of our sex life.

  One of us thinks he or she might be gay/straight (depending on relationship orientation).

  If you and your partner checked even one of these statements, you need to have about three years’ worth of honest conversation before you even contemplate inviting another person into your bed.

  BARE FACTS

  The fact is, your relationship must be as strong as your desire to have a threesome before you should even discuss it. And you’d best discuss it fully clothed, too—not just as part of pillow talk.

  A threesome is not a way to subvert two-timing tendencies or get your partner to open up about what he wants you to do to him when he’s naked. It’s probably true that lots of threesomes happen as a result of each of the reasons in the second quiz, and that’s unfortunate, because it’s not a good idea to take a relationship that’s on shaky ground already and throw it into an earthquake. Make no mistake: a threesome will shake up your relationship no matter how much you’ve fantasized about it and discussed it and planned it and looked forward to it. It might be great, it might be all you hoped it would be, but things will be different in your relationship when it’s over. That’s why reality is so different from fantasy and why for couples a threesome should not be a spur-of-the-moment decision that is entered into lightly.

  DON’T BE A JERK

  The fact that your favorite twentieth-century psychoanalyst forced his wife to accept a third person into their relationship (and she put up with it for decades) doesn’t mean it’s ever okay to force or overly persuade your partner into a threesome. Things will not end well.

  If you’re sure you want to do it, read on and discover the who, what, when, where, and how of threesomes.

  BEGINNING THE JOURNEY

  You and your partner had a passionate sex session last night—it really got going when she mentioned how hot it would be if she could be having anal and vaginal sex at the same time. You got out the dildo and simulated it, and she had one amazing orgasm after another. It was pretty fantastic for you, too, and now, the next day, you’re thinking about how incredible the fantasy was and how much you might like to try it out in real life. So … how do you broach the topic with your partner?

  The good news is that because you are open and honest about fantasies, it won’t be an enormous, ridiculous jump to discuss the possibility of a real live threesome.

  SNAP OF THE FINGER

  For those of you who don’t talk about fantasies and are thinking of a threesome, start smaller. Try talking about toys or fantasies first so that you don’t precipitate a coronary in the love of your life.

  If you have a generally open and honest relationship already, bringing up the idea of a threesome shouldn’t cause anyone to get upset or be shocked. It is, however, a matter to be handled delicately.

  Assuming your initial statement (for example, “So, honey, how would you feel about maybe making that fantasy of two people pleasing you at once a reality?”) isn’t met with tears or hand-wringing, there are probably a lot of questions that will be asked, and you’ll need to answer them honestly and with a fair amount of sensitivity. If your relationship is solid and healthy, that shouldn’t be a problem.

  COMMON INITIAL QUESTIONS

  Why do you want to do this? Aren’t I enough for you?

  Are you gay or bisexual?

  Do you still love me?

  Is this just an excuse to do it with someone else?

  What about our wedding vows?

  Are you cheating on me?

  Will you leave me if I don’t do this?

  If I do it, do I have to have sex with someone of my own gender?

  If you bring it up and your partner has any of these questions, answer them honestly. If he or she is assuaged and receptive to the idea after you’ve done this, wonderful. If not, you may feel that you should try talking your partner into going through with a threesome. This is not a good idea. You both must want it; one partner should not just go along with it. That partner probably won’t enjoy it, and that’s a perfect recipe for resentment, from which no relationship benefits.

  If the initial discussion did not go well, let the issue lie for a good long time. If after several months you are still interested in pursuing a threesome, try again. If not, it’s no skin off your nose.

  Or, if you’re lucky, you’re both on exactly the same page and really want to do it individually and as a couple, and all that’s left is to work out the details before you’re blissfully on your way to a soft-swinging situation. Good for you!

  Once it’s decided that you will do it, though, there are still questions to be asked and answered, and this is where you’ll need to take a look at yourselves and your relationship and make sure a threesome is what you both want.

  SECOND-STEP QUESTIONS

  What do we hope to get out of this experience?

  If it doesn’t go well, will we be able to talk about it and move on?

  Will I be able to watch my partner having sex with another person?

  What would I like to happen during a threesome?

  What would I absolutely not like to happen during a threesome?

  How much work am I willing to do to make this happen for us?

  Will our relationship be strengthened and intensified if we do this?

  Will our relationship suffer if we do this?

  Once you and your partner have really talked about these issues openly and honestly, you must again assess whether you want to have a threesome. If the answer is yes, there is yet another set of questions to go over together.

  LISTEN UP, THIS IS IMPORTANT

  It’s probably a good idea to identify the gender of the third person in your proposed threesome early in the negotiations. Otherwise, t
he two of you may have very different ideas in your heads.

  ADVANCED NEGOTIATIONS

  1. Do we want a man or a woman to join us for a threesome?

  2. Do we want to ask a stranger or someone we know?

  3. How will we find someone without seeming creepy or weird?

  4. Do we want to meet in our home or somewhere else?

  5. What rules and boundaries must be set before the threesome experience?

  Now let’s break down how to answer these questions for your specific relationship and situation.

  Whether you want your third to be a boy or a girl is a pretty important thing to decide, no? The answer depends on what each of you wishes to get out of the threesome experience. Everyone’s situation is different, of course, but you can omit one sex or the other pretty easily:

  If you are a man and your female partner wants double penetration and doesn’t want to share you with another woman and you are curious about what it might be like to suck dick, you probably want a gentleman to join you (though you might not want him to act like one!).

  If you are a straight woman who is bicurious and doesn’t mind seeing your male partner in a sexual situation with another woman and your male partner has always wanted to see two women have sex, a woman as your third is probably a safe bet.

  Maybe you are in a same-sex relationship and would like to ask someone of the opposite sex to join you to see what it’s like or for any other reason, or you’d like to ask another person of the same sex because voyeurism is your thing or to fully realize a fantasy.

  Who to ask is a tough decision, especially if you decide to ask someone you know. This is a risky proposition, largely because in addition to changing the relationship between the two of you as a couple, your relationship with a third person with whom you are already friends with will also change. A lot. But still, lots of folks want to have a threesome specifically because both members of the couple are attracted to someone they both know. So if it’s a friend you’d like to ask, be cautious and be aware that if he or she says no, your relationship will still change.

  BARE FACTS

  Even if you don’t all get naked together, the fact that you asked your buddy to get naked with you and your partner could make fantasy football sessions or a book club a tad uncomfortable.

  So perhaps you want to find a stranger, someone with whom it will definitely not be awkward with afterward, because you will never have to see that person again at the work Christmas party, say, or at the gym. This is perhaps the most personal choice of all when you’re contemplating a threesome, and it’s a decision the two of you will have to make together. Just remember to consider the consequences.

  If you decide on a stranger, there are a number of avenues you might pursue to find a person to whom you are both attracted and who will be a welcome addition to your bed. The main ways to go about finding a third are these:

  Lifestyle clubs. These are basically swingers’ clubs where couples and singles can go to check one another out and then all play together. Not all clubs allow sex, though, so make sure you know which kind you are in. The major bonus with these clubs is that your first introduction is face to face—you won’t have to worry that the person won’t show up. The drawback is that swingers’ clubs do not cater to threesomes specifically but to all kinds of group sex. Also, there isn’t a lifestyle club on every corner, not even in these progressive times, so you might have to travel a bit to find one.

  The mighty Internet. There are so many adult dating sites online that it would be insane to try to list them here, but Adult FriendFinder (adultfriendfinder.com) and Adult Find Out (adultfindout.com) are popular and allow you to specify exactly what you want.

  SECRET TIP

  Many adult dating sites are free, which is a big plus since you’re probably going to want to spend all your money on lube anyway.

  If you want to keep it very local and you’re in a fairly large metropolitan area, a good place to try is your city’s alternative newsweekly’s personals page. These pages are generally chockablock with folks seeking all manner of kinky fun. The drawbacks with adult personal ads are the same as those with regular ones: People lie. The person you choose might not be “model beautiful” or have a “ten-inch love rod” or might not even show up. Also, someone might see you online—someone you don’t want to know you’re trolling the Internet for a third to visit your bedroom. And it may take some time to find someone, since there are tons of folks out there looking to spice it up. But you’ve already committed to spending quite a bit of time on this, so that shouldn’t deter you.

  Regular bars or clubs. This is a less daunting option for sure, but the chances of finding someone whom you both find attractive and who is open to the idea are slim to none.

  SECRETS TO MAKE YOU LOOK GOOD

  Relying only on the bar scene to find a third can be an exasperating experience. You might have to keep at it for years to you find someone this way, and by then you might not be limber enough to bother.

  The decision on where to meet is based on several factors, though perhaps none is as important as your comfort level. If your third is a friend and lives near you, it probably wouldn’t hurt to talk about it at your own place and then do it there, too. If your third is a person whom you’re meeting specifically for a threesome, you might not be comfortable having the initial meeting in your home because the person is a stranger and you may feel that your bedroom is for you and your partner alone and that a threesome should happen outside it, in a hotel or vacation home or the like. There is also the issue of how far this person lives from you; if it’s a good distance, you might not have a choice except to meet somewhere in the middle. For some people hoping to engage in a threesome, the money for a room might also be a concern.

  YOU’RE WELCOME FOR THE TIP

  Don’t invite a potential third to your home until you are absolutely positive that his person isn’t going to steal your iPad and HDTV.

  Deciding on the rules and setting boundaries for the experience is maybe the most important preliminary step to having a threesome. This is where you’ll figure out what you both want and don’t want from the encounter, and you should hold nothing back at this stage. You need to be comfortable talking about how you want the threesome to go, or else how will you ever be comfortable enough to participate? This deserves its own section.

  SETTING BOUNDARIES

  Here are some rules that should jump-start a discussion of boundaries and make the threesome experience safe and enjoyable for all involved:

  1. Be selective about who you invite into your bed!

  2. Get comfortable with your body.

  3. Be honest about your boundaries.

  4. Don’t do anything any of the participants is uncomfortable with.

  5. Always use condoms and/or dental dams; unprotected sex is not an option.

  6. Don’t drink more than one or two alcoholic beverages to get loosened up; being drunk will compromise your ability to play it safe.

  7. For your first threesome, don’t perform any sex acts with the third person that you’ve never done with your partner.

  8. Respect all participants’ boundaries.

  9. Don’t do anything you don’t want to do.

  10. Don’t assume anything; always ask.

  Some of this is common sense and some of it is a little less intuitive, but regardless of how obvious you think a rule is, you should discuss it with your partner.

  It’s very important to decide on your personal level of involvement before you are actually naked with two people. For example, if you only want to watch your partner get it on with someone else, you need to let your partner know (and your third, but that comes later). If you’re willing to perform oral sex on your third but don’t want that person going down on you or if it’s okay with you for your partner to perform oral sex but not penetrate the third with his penis, you need to tell your partner.

  It might seem ridiculous to have to spell all this out, or
it might seem like it doesn’t leave room for spontaneity, and that’s true: it doesn’t.

  YOU’RE WELCOME FOR THE TIP

  Spontaneity seems like a great idea only until you’re naked and uncomfortable and your partner is obliviously having sex with someone who is not you while you watch.

  Another important boundary to set for mixed-sex threesomes (as opposed to same-sex ones) is how much same-sex contact you or your partner is comfortable with. You may be a woman who is way psyched to make out with another woman but doesn’t want to be involved in a girl-on-girl cunnilingus situation. Or you’re a man who’s always wanted to go down on another guy but you’re absolutely not okay with having anal intercourse with him. These specific parameters need to be itemized. If same-sex behavior makes you uncomfortable, having a “let the chips fall where they may” attitude will not serve you well during a threesome. This experience is supposed to be fun, after all. Setting clear boundaries will help ensure that it is all you hoped it would be.

  Of course, if you and your partner discuss all this and decide that each of you really is okay with whatever might happen—and you’ve considered every permutation of sex that might happen—then by all means, let the chips fall where they may. Go wild!

  MAKING IT HAPPEN

  Once you’ve selected a third and set firm boundaries with your partner, it’s time to arrange the initial meeting with the person with whom you’d like to have a threesome.