Rule #1: Keep it Casual
Even though I’ve had several threesomes, I’ve never had one while I was in a relationship. Why? Because it would get weird. Even if you’re sure it wouldn’t. Even if she’s sure it wouldn’t. Sure, maybe it would work if you’re both polyamorous or into sex with other people as a lifestyle choice, but if that’s the case, chances are you don’t need to read this to learn how to have a threesome.
You can definitely do it with a woman you’ve just started seeing, but think twice if you want to be with her longterm. Personally, I’ve found the best combination is me + friend-with-benefits + his bisexual friend-with-benefits who is visiting from out of town. Ideally, the situation would happen organically, but you may want to help things along with games of “Never Have I Ever” or confessions about the craziest stuff you did in college.
