I'm a single 27-year-old woman. I've talked to this one guy in the Army off and on for about six years. He's been in and out of the country over those six years, and is in town for now. Long story short, we had sex a couple weeks ago. Finally! It was the best sex I've ever had. Since that night he's been asking me about having a threesome. He is also asking what kind of threesome I would like to have—me/him/guy or me/him/girl). I'm young and this is an opportunity, so I'm up for either one as long as I'm attracted to the other person. But here's the problem... I have feelings for the Army guy. They're not full blown feelings, but I have carried a torch for this guy for six years. Yes, I told him I have feelings for him but he doesn't return them. In fact, he's said he'd like to have this threesome with someone who he cares about but who he isn't in a relationship with. I'm that person for him, and pretty sure that means he doesn't and won't ever want to be in a relationship with me. Also, I've had a foursome before with someone I was in a relationship with and it was not a good experience. I realize that that doesn't mean I'll have a bad experience in this threesome, but I need to get over this mental block. I feel like I can't talk to my friends about this because they'll tell me not to do it and I really want to do it.

Should I have a threesome with my Army guy despite my feelings for him and my past negative experience?

Should I Have A Threesome?

My response after the jump...


I wanna tell you to have the threeway—I've advised readers in the past to err on the side of threeways—and I'm probably gonna tell you to have the threeway before I'm through writing this response. But I have to say that I'm a little concerned about 1. your feelings for this guy and 2. the way this guy seems to be making a distinction between things he'll do with a girl he's in a relationship with and things he'll do with a girl he isn't in a relationship with.

In my experience, SIHAT, people who only do kinky shit with strangers or FWBs or fuckbuddies—never with actual girlfriends/boyfriends/husband/wives—don't always treat those strangers, FWBs, and fuckbuddies very well. They seem to see their kinks as somehow degrading, something they couldn't do with and/or to someone they actually loved and respected, and consciously or subconsciously they hold the strangers/FWBs/fuckbuddies they do that shit with in certain degree of contempt.

You're probably a little heartsore already, SIHAT. You have feelings for this guy, you told him about those feelings, and he made it clear he doesn't feel the same way about you. So how will you feel if you get the impression after you've had this threeway—or while you're having this threeway (God forbid)—that this guy regards you as unworthy of his love and affection precisely because you had (or you're having) this threeway with him? If the answer is "much, much worse," SIHAT, you might want to pass on this threeway.

Wow—it looks like I'm not gonna tell you to err on the side of this threeway. That's unlike me. But I do think you should have a threeway sometime. Just with someone else. Or a pair of someone elses.