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Does three make a crowd?

Dear Jackson,

My boyfriend and I have a pretty wild sex life. We’ve talked about having a threesome for a while. First it was just a bit of a sexy joke, but now it looks like it might happen. She’s a younger woman (I’m mid-30s, she’s 24), very flirtatious and absolutely gorgeous. My boyfriend and I met her at a bar. I wouldn’t call myself bisexual but I’m interested in experimenting and want to keep the relationship (coming up to the three-year mark) fresh.
Equally, however, I recognise that I am a deeply jealous person. I’m worried taking this beyond a fantasy could ruin the relationship.

When you think of your boyfriend with this girl, are you turned on? Filled with jealous dread? Or a bit of both? If you’re on the fence, there are a few things you need to consider . . .

For most people, threesomes belong in the fantasy realm. If the relationship is long-term and committed like yours, the quick fun of the experience could quickly lead to a host of problems.

Watching him go at it with another girl is likely to bring up questions like: what if she replaces me? What if he likes it better with her? Will he start sleeping with her when I’m not around? There’s a big difference between experimenting as a couple and inviting a third person into the bed.

You need to trust your boyfriend and feel sure of yourself if you’re going to go through with this. And remember, the idea ought to turn you on as well. Make sure you’re choosing a girl you like too. From the tone of your question, it doesn’t sound like you are. “Younger woman”, “very flirtatious”, “absolutely gorgeous”?

If you’re eager to please your man and you don’t want to potentially hurt yourself and the relationship, there are other ways to keep things fresh: role-playing, new positions, novel locations, toys, etc.

But if I’ve read you wrong, and you are serious about giving this a try, you need to lay down some ground rules. Tell him what you’re comfortable doing and seeing him do. Tell him what would bother you. If you don’t want him hanging out alone with this girl after the fact, be clear about it. Gauge his response.

Try testing his emotional fidelity. Even if it doesn’t interest you, ask him if he would be willing to bring in another guy. If he won’t even consider it, does he really deserve you putting yourself out on such a limb?

If he gets defensive, it means he’s interested in sex with someone else, not mutual exploration – and the latter is what this experience should be. If he’s sensitive about it, perhaps he’s mature enough to turn this fantasy into a hot and fun experiment.

Still in doubt? Maybe it’s best to say no. After all, you risk opening a pandora’s box of insecurity that will last long after the fleeting passion.

Got a question about sex or relationships for Jackson? Email ppp.lifestyle@gmail.com

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