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Miss Information: A threesome of threesome questions.

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Miss Information

Dear Miss Information,

My long-time girlfriend and I picked up a stranger this weekend. One of our fantasies has always been to have a threesome with another man. As luck turned out, this guy was very well hung. She was moaning and writhing like I've never seen before. Hot, yes. But now I'm worried that she's going to be bored with my sub-par equipment. Everything works, but I'm on the small side. Not tiny, but average. I'm not opposed to messing around with this guy again, but I also don't want to set myself up for trouble in the future. Should we find a new partner, one that doesn't make me feel as insecure? My girlfriend said she's okay with whatever I decide. — A Worried Mind

Dear Worried Mind,

I think you're focusing on the wrong thing. You girlfriend experienced a strange cock, a new cock, a not yours cock. Not only that, but, two cocks. At the same time. And all the dirty anatomical possibilities that brings. That's what had confetti and that Kool & The Gang song shooting out of her vagina. Not some stupid size difference. A big wang is nice, don't get me wrong. But a sexually adventurous boyfriend with a serviceable wang is even better. And I trust that yours is serviceable, seeing as you two have been together a while and are still horndog enough to be trying some advanced-level ninja shit like this. Most couples just give up after year two and settle for missionary position between Daily Show commercials and trips to Home Depot.

Ask her what she liked about the experience. I doubt she's going to say, "You know, it was those extra two inches that made it." On the off chance she does, you guys can explore ways to give her that same "Holy-Shiva-I-can-feel-it-bumping-against-my-sternum" kind of feeling — whether it's changing positions and angles for deeper penetration or going all crazy with toys and dildos.

If it still bothers you, find a new third party, and make him send dick photos before your first encounter. Then go shoot the bejesus out of some forest creatures, and commission a car-show model in a thong bikini to do a huge nine-foot sculpture of your cock in bronze leaf. You obviously have something to prove regarding your masculinity.

Finally, remember that when it comes to choosing a threesome partner, dick size is rarely the threat. Much better to have a fella with a twelve-inch schlong who respects boundaries and limits than a three-incher who's trying to schedule dates with your wife on your side.

Dear Miss Information,

My best friend is bisexual and a big flirt. She keeps coming on to my boyfriend and I whenever we're together. She walks around in her panties, touches me and has told me I'm hot while making eyes at my boyfriend. While I find her gorgeous, I'm uncomfortable with the idea of a threesome. My boyfriend is not so opposed. I want to stay friends with her and keep my boyfriend, but I am unsure what to do. — Terribly Confused

Dear Terribly Confused,

Your best friend is chilling in her underpants around you and your man. She's touching you and coming on to you. You're feeling weird about the situation. These are the facts.

Sex Detective #1 would look at the evidence and say, "This chick needs to speak up and set some boundaries." I know you want to appear to be Ms. Open-Minded, especially around your wild-child best friend, but is maintaining that rep more important than feeling secure in your relationship? As Mrs. Bobby Brown would say, "Hell to the no." Talk to your boyfriend and your best friend. Quick.

Sex Detective #2 has a different view. She thinks you might be a little intrigued by going gay for a day, but you're worried about how you and the boy will handle it. Will he like her more than me? Will the two of them run off together? This one doesn't have an easy answer. I will say that there are other ways to explore threesomes that don't involve knocking boots with your best friend. A more neutral third party might be more appropriate.

Whichever coital Columbo you decide to go with, it's vital to stay true to yourself and what you believe. Boyfriends and best friends are powerful influences, and I'd hate to see you compromise what you want just to please them.  

Dear Miss Information,

I found out the girl I'm dating was involved in a threesome with two other guys. I'm not normally a jealous type, but this revelation made me cringe. I decided my retroactive jealousy was irrational and I read up on the subject and talked to friends. I didn't tell her since I considered it "my problem" to get over. A few days ago, she said to me that a person's sexual past is a part of that person's identity. This flew in the face of my coping mechanism, so I pushed back. She could tell something was up, and I eventually told her everything. She became upset that I hadn't told her and said that the discussion we were having was evidence that I hadn't "gotten over it." I immediately regretted having told her anything.

Am I wrong? Shouldn't I have tried to work my irrational jealousy out on my own and not reveal it to my partner? I still don't see what good can come of sharing these sorts of emotions. Isn't that what confidants and therapists are for? Now that I've revealed my initial reaction, I feel that the problem has only gotten worse. I wish there was a way to put the genie back into the bottle. — Potential Oversharer

Dear Potential Oversharer,

Why is jealousy over a threesome irrational? I don't like to think about a guy I care about doing it with someone else, let alone two people. At the same time. In a really erotic act only a small percentage of the population ever gets to experience. Sometimes in our quest to be sexually open, we wind up acting more like the repressed Puritanical-types we're trying so hard to distance ourselves from. In trying to be "mellow" and "understanding" and "free," we sometimes mute our emotions, and that's where we start to fuck up. Saying one emotion is more valid than another is the exact opposite of what all the sexy libertine folk wanted us to do in the first place, which is be super-open and honest with our feelings.

If it bothers the fuck out of you to think about your lady with someone else, then own that. Don't paint yourself into some box because it's how you think you're supposed to feel. Now, while there are no bad feelings, there are bad ways of handling those feelings. Which takes us to your discussion with your girlfriend. You hammered too hard on one element of what your girlfriend thought was an esoteric argument. Then she finds out it's not an esoteric argument. I'm sure she felt defensive and like your tactics were misleading. Which they were. But not on purpose. You were just finding an indirect outlet for your anger and jealousy. It felt safer for you to debate philosophical questions like "Is better to tell or not to tell?" "Should past lives be kept in the past?" "What constitutes a sexual identity?" than go to your girlfriend and ask, "Is our sex life interesting enough?" "Am I too vanilla?" "Are you bored with me?"

Let's end the "I wish I never told you!" "Oh yeah, well I wish I never told YOU!" stalemate. That's not going to get you guys anywhere. I want each of you say your worst fears about the threesome issue out loud. Get that shit out in the open. Let the other person refute them or confirm them or partially confirm them or whatever. Is there anything she can do to make you feel better? Are there any promises you can make re: the next time you're feeling all caveman? What about some new ground rules for discussing your sexual histories? Don't let the most important part — your relationship — get lost in all the intellectualizing and rationalization.