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Sex With Steph: How To Have A Threesome

Two years ago, I was lucky enough to find an amazing, loving, and supportive man to share my life with. Our sex life has been GREAT, and we enjoy playing with fantasies. Recently, I admitted that I fantasized about having a threesome with him and another woman, and he told me that he fantasizes about the same thing. (I know, big surprise.)

At first, we just enjoyed using the fantasy as fodder for our dirty talk during sex or for sexy phone calls when I traveled for work. But a few weeks ago, he asked if I had ever thought about taking it beyond a fantasy and actually having a threesome. I have to admit, I really like the idea. It turns me on, and I want to do it. The problem: we don’t know where to find a third person. We live in a small, conservative town, so it isn’t like we can just go to the local swinger’s club. Do you have any advice for a couple of swinger wannabes? How do we find someone? What kind of questions should we ask? What precautions should we take?

And, in case you were wondering, my man says that he will still love me even if we don’t have a threesome.

A long time ago, in a universe that seems so far, far away, and at a time when my wardrobe consisted primarily of wide-leg jeans and random T-shirts, I was a sweet, suburban 16-year-old who had never been kissed. The me of that time never imagined that, one day, I’d touch my first penis, begin a long-term love affair with a vibrator, take cardio-striptease classes, attend sex parties, cuddle parties, and porn parties, and have my very own sex column. She certainly never imagined that she’d one day have a personal touchstone relevant to a threesome-related question.

But before I ended up marrying some dude I met on Friendster, a woman contacted me through Nerve personals and asked if I’d be interested in going out with her and her husband. We never slept together, but we did go out on several dates. You know. The usual. Dinner. Drinks. Fetish-wear shopping on Christopher Street. They referred to me as their “cute little submissive.” It was nice.

If this experience taught me anything, it’s that it’s possible to find people who are open to just about anything, no matter where you’re located.

If you’re looking for another woman for your Sexy Time Triad, it could be ideal for you to do the fishing. Why? A woman may be more comfortable talking to you about the possibilities of a threesome because then she’ll know that you’re as invested in this experience as your partner is. No woman wants to unsuspectingly come between a man and his jealous, forced-into-a-threesome woman.

So how do you find someone who’s up for the experience? Well, it can help to target those who are already looking.

Try personals sites. That way, you and your man can shop for the perfect sex partner together. Dating-oriented sites like Nerve allow users to specify whether they’re looking for men, women, or both. To further narrow down your search, you can pop in “threesome” as a keyword. That way, you’ll know that anyone you contact is already interested.

Hit up the dance club. Those hosting mixed dance parties can be ideal for finding someone willing to play with both men and woman. Put on your dancing shoes. Have fun together. Flirt with others. Keep it casual and treat this particular fishing expedition like any other nightclub pickup.

Tap into your network of friends and acquaintances. While I would find it weird to bring someone I already know into the bedroom (wouldn’t it make things awkward later on?), you may feel safer going that route.

Find yourself a swinger party. Or a sex party, or a cuddle party, or a kissing party, or an eye-gazing party. While most towns don’t have a local swingers club you can pop into at any time, many smaller towns do have roving parties under the radar. Look online and see if you can find something close by.

Go on vacation. A sexy, hedonistic vacation.

As for what questions to ask, you may be over-thinking this. (Though a few pointed questions about a person’s sexual health wouldn’t be out of line.) What have you asked anyone in the past before having sex with them? More important than asking questions is establishing ground rules. Every person partaking in this threesome will likely have varying comfort levels when it comes to sex play. Sit down and have a talk about which sex acts you’d like to avoid (perhaps you’d prefer your partner didn’t penetrate another woman, or share an intimate kiss with her), or whether or not the third person will be allowed to sleep over. And you should stress the fact that, if anyone’s feeling uncomfortable, they have the right to pull the plug at any time.

Keep in mind, jealousy may pop up when you least expect it. It’s only natural. When you’re used to having sex with only one person at a time, it can get logistically confusing to divide your attentions equally amongst two people. You should all agree to make your best efforts to ensure that no one feels neglected.

And above all, practice safe sex.

Got a question for “Sex with Steph” sex adviser Steph Auteri? Send her an email with your sex questions!

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