Sexy Time: One, Two, Three, Not Only You and Me

Threesomes seems like they’re becoming less and less taboo and scary these days. I saw one in person at a bachelorette party. Britney sang a song about threesomes and it debuted at number one on the Billboard Hot 100. Gossip Girl featured the most awkward threesome ever in the history of the universe a couple of years ago (Dan, Vanessa, and freaking Hilary Duff? Still not over it). I’m pretty sure any reality show that involves a bunch of strangers living in a house for a prolonged period of time cultivates in a threesome (or more) at some point. They just don’t seem to be as scandalous and taboo as they once were.
That said, the idea of engaging in one myself seems daunting. I occasionally like to tease my boyfriend with talk about having a threesome with his favorite model, but imagining myself in a threesome is…difficult at best. However, my inner Girl Scout always wants me to be prepared, so naturally I’ve done some research on how to make a threesome not suck.
Talk it through thoroughly with your partner.
Cover all the bases – the participant, the logistics, the potential emotions…everything. Determine if the third is going to be a guy or a girl. A stranger or a friend? Make sure you have a totally private place that you can make as comfortable as possible. Talk about your worries, your insecurities, the possibility for jealousy, the ramifications of your relationship. Incorporating someone else into your own little intimate world is not something to be taken cavalierly. Make your boundaries abundantly clear – is penetration okay? Vaginal or anal? What body parts are off limits? What about oral? Toys? Role play? It’s important to set detailed ground rules before it happens, so you’re not completely taken aback in the moment.
Make sure you’re totally okay with it.
If the only reason you’re into the idea of a threesome is because your partner has mentioned it, don’t do it. Sex is supposed to be pleasurable for everyone involved. Your partner’s happiness can’t override your own. ┬áMoreover, a threesome challenges a lot of our ideas of our sexuality, which can be terrifying and unnerving. But being in a threesome doesn’t necessarily mean anything significant. Sexuality is a spectrum. Being aroused by someone of a sex/gender you’re not usually attracted to doesn’t mean you have to totally re-evaluate your sexual identity. It’s okay to have to work through some hangups before you decide whether or not you’re interested.
Find a good fit.
I’m no threesome expert, but I don’t think the “third” should be someone you are friends with. While it may seem like a great idea — you know the person, trust them, can communicate with them, etc. — I think it would ultimately end up being messy and sloppy and not worth it. I’m not saying it’s impossible, but it’s highly unlikely that the dynamics of the friendship wouldn’t be irreparably damaged. Luckily, we have the Internet. Craigslist, Adult Friend Finder, Sexually Social and FetLife are all sites you and your partner can find candidates. Don’t approach this expecting to email someone today and be naked with them tomorrow. Take a few days to correspond, maybe go out to coffee or something to see if the chemistry is there. The best thing about finding someone online is you can be completely straightforward since everyone knows what the endgame is.
Be safe.
Everyone should know everyone else’s STD status. Don’t be afraid to ask for proof. This is your health and it’s super important. Make sure you don’t double dip with condoms. Never use the same condom with two different partners. Make sure you assign a hand to each person so you’re not, um, “cross-contaminating.”
Have realistic expectations.
While, ideally, it would be awesome if all three of you connected seamlessly, and the sex was spectacular, and everyone felt 100 percent amazing about it, there is also the very real possibility that one or more parties is going to feel uncomfortable before, during and/or after. Someone may feel left out and jealous. Someone may have just been totally bored. Someone may have started developing feelings. Sex can stir up a vast spectrum of emotions due to the hormones and chemicals our bodies produce, and it is okay to reflect on your experience and not like it, or to reflect on your experience and want to repeat it. Like everything else, a threesome is just a live and learn experience. It doesn’t have to be a defining experience if you don’t want it to be.

Ask A Dude: How Do I Know If I'm Doing It Right?
Ask A Dude: How Do I Know If I'm Doing It Right?
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