All the questions you need to ask yourself before having a threesome

I’m [an older] female, and my boyfriend wants to do a MMW threeway. Should I?

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—Anon.

Dear Anon.,

That really depends on what you left out. Namely, do YOU want to do a man-man-woman threeway? If you have zero interest in pursuing this kind of arrangement, then it doesn’t really matter if your boyfriend wants to try it.

If, however, you are maaaaybe into it, but on the fence about it, you should ask yourself what your apprehensions are. Make a list. Be specific. Write everything down that’s a pro or a con about banging another dude with your boyfriend.

Some things you might want to think about: Does this idea turn me on? What about it, specifically? Is it the taboo, the multiple hands and mouths on me, the novelty? What about it makes me feel squicked out? Will I feel jealous watching my boyfriend mack on someone else? Does he even WANT to mack on someone else, or is the third only going to play with me? Will my boyfriend feel jealous if I mack on someone else? Are there boundaries I don’t want to cross? (For instance: certain sex acts or intimate acts, such as kissing, touching, penetration, oral or even spooning and sharing a bed with a third. Would you rather the third person leave right away, or is staying the night OK?)

Other issues to ponder: What kind of safer sex precautions do I require to feel safe and cared for? Do I have a third in mind? If not, how will I go about finding one? What kind of person am I interested in banging, and is my boyfriend on the same page? Do I want to know the third (as in a friend or acquaintance), or would I prefer it be a stranger?

Will this be a one-time deal, or do we want this to be incorporated into our relationship? Do I have safe words I can say if things get out of hand during the threesome? Do I trust my boyfriend and the third to respect my boundaries? When and where will the deed take place? Would I rather it be in the comfort of my home, or would that feel weird to me?

If and when you do find another person to play with, you then have to communicate with HIM so that you’re all on the same page. For instance, “We’re so excited to [verb] your [noun] soon, but just want to be clear that anal, kissing and sleepovers are off the table. What are you looking for?”

Remember, also, that you don’t have to go all the way on your first time. You can stick with making out and touching to see how that feels and proceed from there.

That’s probably a lot for you to think about all at once. To pare it down, the biggest consideration is: Do I want to do this? Do I find it hot or intriguing or exciting?

If the answer is yes, then give it a whirl. If the answer is maybe, in the right circumstances, your next step will be to go through some (all) of these questions with your partner and discuss expectations and boundaries. Don’t skip them! “Winging it” in threesomes can lead to a lot of hurt feelings, regret and unnecessary laundry.

Good luck!