Three is a Magic Number

Dear Tippy Maple,

My boyfriend and I have been thinking about having a threesome. Do you have any advice on where to start or how we should pick the third participant?


Three’s Company

Dear Three’s Company,

What a shame that we’re both writing anonymously because I’d say yes to your proposition in a second! But if for some reason I’m not your ideal third participant (I can’t imagine why I wouldn’t be!), I can still impart some threesome wisdom to you and your boo.

Let me preface this article by saying that I might not give the most relevant advice as I know neither your sex nor the sex of the person you would want to have in your threesome. Seeing as possible threesomes you could be having range from guy-guy-guy to girl-girl-guy, I’ll give you my personal spiel, and then we can go from there.

Personally, all the threesomes I’ve had have been impulsive decisions that alcohol has helped come to fruition. I apologize if in my very official Tippy Maple capacity I appear to be condoning drunk hookups; there may be better, safer, more sober ways to go about initiating threesomes, but none of them have worked for me (yet). All possible threesomes discussed between different combinations of lovers and friends have come to naught—probably because it can be pretty awkward to ask people to have a threesome!

I’ve found that the most successful way to start threesomes is if I am already hooking up with a female friend and we either ask a man to join us or somehow a male onlooker turns into a participant. I blame this on our voyeuristic, misogynistic society and the threesomes that are overwhelmingly represented and idealized in porn. But as a horny, bisexual female, I’m not complaining too much because this patriarchy has helped me simultaneously hook up with one female and one male (which just so happens to be my favorite type of hookup).

Unfortunately, comparatively, you and your boyfriend are at a bit of a disadvantage. Because of our lovely patriarchal culture, it happens to be a lot easier to find a straight man willing to have a threesome with two girls than it is to find either a man or a woman willing to have a threesome with a heterosexual couple. If you and your boyfriend are both men, then that is yet another situation, one that I don’t feel as qualified to speak to (unless you are looking to have a threesome with a woman, in which case I again, quite enthusiastically, volunteer myself!)

I’d recommend that you start by casually asking friends that you both find attractive about their views on threesomes in general and their interest in pursuing one. Don’t drop your and your boyfriend’s names right away; just gauge their overall interest level about a threesome in the abstract. If your friend seems especially enthusiastic about having a threesome, talk with said friend and your boyfriend (separately). Then, at some future time, all get together, and, probably after a few glasses of wine, get down to business.

Assuming this route isn’t successful, I’d say wait until you’re at a party and, after a few glasses of wine there, casually approach attractive acquaintances. If you happen to know if the person you’re approaching is bisexual/pansexual, that might be especially helpful (I don’t mean to imply that bi people are the only ones who want to have threesomes, but we can often be a good bet). This might be fairly awkward, but once conversation is flowing enough, ask the person if they want to have a threesome! Worst case scenario, they say no (but they will at least be flattered that you asked), but, if all goes well, you can ménage à trois away.

Assuming your threesome works out, I have some general threesome guidance. First, establish ground rules for how far everyone is comfortable going with everyone else. Next, make sure no one feels left out. Three is an odd number, which means an even sharing of attention is really important. Especially because you and your boyfriend are in a relationship, be aware of your emotions; if one of you starts to feel jealous, make sure to communicate or it could lead to animosity later on. Last, make sure you try as many fun positions as possible! I recommend “eiffeling” or some variation thereof, which is essentially one person on bottom pleasing both people on top using their mouth for one and their genitals for the other. (If you’re unclear, just Google it.)

May your quest be successful, may your bed be full of threesomes.

Happily Horny,

Tippy Maple

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