How do you flirt with a couple/ escalate things into a threesome? (NSFW?)

Asked by Theory (82

) March 26th, 2011

I’m cautious by nature. I’m also openly bi. There have been times when I thought a threesome could happen, but I didn’t/ couldn’t go through with it, because I sensed that the attraction wasn’t equal all around or I sensed jealousy or reluctance from one of the partners. And just FYI, I’ve had plenty of one-on-one dating and relationships, and sometimes potential threesomes came up then, as well. Right now I just want to explore.

I want to make a good faith effort to make sure nobody’s feelings get hurt- if I get together with a couple, I don’t want to be part of the emotional life of their relationship. I want it to just be about the sex, I want it to be temporary/ occasional, and I want the relationship to be just as strong when I leave as it was before I got there. Like the campsite rule- leave it in better condition than the way you found it.

I know a couple now where it seems like it could work. I’m equally attracted to both of them, and they seem really solid. They’re gracious and affectionate toward each other. I’ve been friends with them for three years and I haven’t seen any weird emotional issues. In fact, they’re all-around awesome.

When we get together, they’re a little touchy-feely toward me. She’ll hold my hand or he’ll put an arm around both of us and stay like that for a while. Nothing happens that’s overtly flirtatious or over the line of regular friendliness, but they do touch me quite a bit. It’s affectionate, but I have no clear grounds to think that it’s attraction.

Of course, it’s very likely that they think of me only as a friend and that they aren’t interested at all. So what’s the best way to politely let them know:

1) I think they’re both hot and I want to have sex with them.
2) I don’t want to break them up, cheat with either of them, or stir things up between them. I’m only willing to go through with it if they’re both enthusiastically on board.
3) I want to be an occasional (or even just one-time) guest in their bed and that’s it. I don’t want to be a third party in their relationship relationship.
4) If they’re not interested, it’s cool.

I’ve done a lot of soul-searching about it and I can honestly say that all those statements are true. I’m single, I’m having fun, and I’m a free agent right now. Feelings can change and intensify after sex, but emotionally, I think we’re all in a pretty levelheaded, lighthearted place right now.

What’s the etiquette for graciously letting them know that I’m interested, and maybe someday being a guest in their bed? If it matters, I’m a girl. She’s bi and he’s straight. We’re all in our mid 20s.

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8 Answers

Option 1: open and honest conversation.
Option 2: tequila and truth or dare.

nikipedia (28095

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I have no idea what might be standard procedure, and unless they do know, I don’t think it matters that you don’t. What seems more to the point is a gentle, respectful, and yet clearly communicative approach.

Going on nothing but my own imagination and intuition here, I would think perhaps a discreet exploratory conversation with the female member of the pair would be the way to go.

I would also be prepared for a permanent change in my relationship with them if I had misread the situation and offered an unwanted invitation.

Jeruba (56064

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I have no experience with this topic, but my guess as a method to save face if the question fails is just to pose it as a joke. Like one day if you guys are laughing and horsing around, say (with a lot of laughter) “yeah, let’s have a threesome!” Then see how they take it. If it falls flat, then don’t bring it up again. If they say (and maybe they may sound joking) “Yes, lets.” then you can kind of get serious like “Seriously?” and then continue in that vein.

I think the worse that can happen with my idea is that they think your jokes are becoming a tad inappropriate (not knowing, then, that it’s not really a joke).

jca (36062

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@nikipedia How about a thoughtful and honest conversation, while under the influence of tequila? Just kidding :)
@Jeruba That might work, actually. You bring up a good point.
@jca Testing the waters first is definitely a good idea.

Okay, how about this. Say you’re in a relationship, and a friend starts flirting with you. What could she do that would make you consider/ not consider the idea? What’s attractive, and what’s over the line? I really want to get into their pants.

Theory (82

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I think the fact that the female partner is bi makes this a special case and should work to your advantage in several ways. How a straight person might react probably won’t help you much.

Jeruba (56064

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I think @Jeruba is on the right track. Before getting into specifics, I might talk to the other woman and get her input on the concepts of threesomes in general. That way, if she seems uncomfortable with the topic, you can back away gracefully without it making things awkward between the three of you. However, if she seems receptive to the concept of threesomes, you can mention your personal interest and see how she reacts.

The big thing to remember in situations like these is to take things slowly and have a lot of communication and compassion for everyone involved.

Raven_Rising (2215

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I think I’d approach the female first, too. If she’s open to the idea, she’ll take care of bringing her partner into the fold. A little tequila certainly couldn’t hurt, either. ;)

augustlan (47745

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And if she’s not open to the idea, she won’t be pleased if her partner is.

Jeruba (56064

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