Every guy thinks he wants to have a threesome. They just look like so much fun in porn. The problem is, real people aren't porn stars.
Before anyone says, "But Cosmo Frank, I think my gentleman lover would enjoy a ménage à trois in which I am intimate with another woman," let me say two things: first, why are you talking like you're from the 1920s? And second, every guy thinks they would like that. They might ask directly, or drop hints and hope their girlfriend will get the idea to have one "herself." This is because before a threesome, there's little understanding of what's about to happen.
Other men realize that threesomes are a recipe for disaster. They can work, but it takes a very specific kind of couple and a specific kind of situation. I'm not going to get up on a soapbox and scream at everyone to never have threesomes (after all: porn still has to get made). I don't even know where to get a soapbox. But I think if you're on the fence about having one, the answer is just an outright "no." Strangers, or people in noncommittal relationships, or couples who are confident they don't mind sharing their partners with other people are one thing.
Here's what happens in many real, not-porn threesomes: two people do a lot of active fucking, and one person kind of hangs out. You have to ask yourself if you're OK watching your significant other give it to someone else for a while. If the answer to that question is "yes," then go crazy. If the answer is "no" or "I'm not sure" or if there's any kind of pause, don't do it. You can't go into it with any kind of doubt.
I know plenty of unicorns this has happened to. I've heard the phrase "sick to my stomach" used more than once when describing a threesome, and oftentimes it was a guy describing a threesome with two women. If you're going for guy/girl/guy the potential for awkwardness increases exponentially, at least as far as the guy (if he's straight) is concerned. If this is the kind of thing you want to try as a couple, maybe ease your way into it first. Have someone just watch you or try some mutual masturbation. Because you might hate it.
If your man is clamoring for a threesome, and you are just not interested in having one at all and have expressed as much? Then he's probably not worth your time and you should dump him. His fantasy should not be more important to him than his relatlonship with you.
I'm not trying to stand in the way of anyone's good time. Have sex how you want when you want. But know that, if you actually DO go all the way to Threesome Land, all three of you need to be ready for a straight-up awkward sexual encounter. If you're up for that, the best thing I can say is: I'm praying for you, and stay hydrated.
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