Nov 14, 2007 at 12:00 am
I’m a 24-year-old heterosexual male who’s been in a monogamous relationship with a 26-year-old GGG girl for about a year and a half. During this time, we’ve more or less constantly expanded our sexual boundaries, to the point where we were planning on going to a sex club here in Tokyo (we’re both expatriates) in order to make some group-sex fantasies that we’ve both had and expressed come true.

About six weeks ago, a friend of mine introduced me to a friend of his, who happens to be a pretty cool 22-year-old girl. We hit it off and I introduced her to my girlfriend. Likewise, they immediately click. Fast-forward to a recent get-together that ends with the three of us hanging out at the end of the night. I offer (twice) to set up on the floor so the womenfolk can have my bed, but they both tell me not to worry about it, and so we sleep curled up with my girlfriend in the middle.

The next day, my girlfriend brings up how nice it was to have all three of us in bed together, and asks me if I thought this new girl was bisexual. I tell her that I don’t know, although given how quickly the two of them curled up, I was halfway disappointed that it didn’t end in a three-way. She says that I’ll just have to be in the middle next time so I can make out with both of them and get it started.

The new girl shows up at the party that night, proceeds to get drunk, and is put to bed in my girlfriend’s bed. When everyone else leaves for karaoke, I stay behind to help clean up the place. We finish, and I comment about how I should probably head home and let them have the bed. She says that we slept three across last night, and there’s no reason we can’t do it again. So I borrow some pajama bottoms from her, get set up on the opposite edge of the bed from the passed-out friend, and am told to scoot in to the middle by my girlfriend when she gets in bed. All is well, I tell her I love her, and we go to sleep.

The next morning (that is, this morning), however, I wake up spooning the new girl, with my girlfriend nowhere to be seen. I go into the other room to find her washing dishes and notice something seems a little bit off. She says she’s going for a jog, changes clothes, and takes off, leaving the two of us behind.

The new girl gets up, we talk for a while, and (surprise, surprise!) we kiss. She asks me what I want, telling me that my girlfriend is fantastic and that she doesn’t want to come between us, and I confess that I’m a bit greedy and kind of want to have them both, to which she responds that she’d be fine with this.

After she leaves, my girlfriend comes back and we start talking. She immediately begins crying when I tell her I kissed this new girl. She adds, though, that she loves me and still wants to be with me even though I’ve cheated on her. I’m initially a little taken aback by this reaction, given the relative tameness of the offense and what I perceived as fairly clear go-ahead signs, but I leave after shedding my fair share of tears, apologizing, and telling her that I love her and want to be with her.

So, Dan, after this long and winding story, my question is this: Did I get ahead of myself and misread my girlfriend’s intentions? Or did I read them right, yet break some other statute when I kissed this girl on my own? I’m leaning toward the second one myself, but threesomes are kind of new territory for me, so I’m having trouble figuring this out. —Thither Hetero Ecstasy, Thither Awful Infidelity, Now Torn

"Blessed with a girlfriend who is game for a three-way, you botched it by breaching a cardinal threesome commandment," says Vicki Vantoch. That commandment? Thou shalt communicate. "Your girlfriend gave you a golden opportunity and you screwed up by making assumptions."

"When it comes to threesomes, it’s critical to not leave any room to misread intentions. You can’t know exactly what your girlfriend is cool with unless you ask for specifics. So, before you stick your tongue down your new friend’s throat, ask your girlfriend. You need to ask a lot of questions. If you’re unsure about what’s OK with your girlfriend, pull out the dry-erase board and ask; draw out a game plan; write a checklist of approved behaviors."

But even a nonassumption-making couple with an elaborate game plan may encounter turbulence once the three-way is under way.

"That’s why it’s always a good idea to check in with your girlfriend often during a three-way and get explicit permission for each new move," says Vicki. "Checking in can defuse uncomfortable moments before they erupt into emotional shitstorms. When your girlfriend seemed ‘weird,’ do you really think it was smart to respond by sucking face with a new friend? A response that might have salvaged your three-way (and likely deepened your relationship with your girlfriend): Stop and ask your girlfriend how she’s feeling."

What do you do now?

"Beg for forgiveness," says Vicki. "Listen to your girlfriend talk about why she’s upset, and with the grace of god, she’ll forgive you and you’ll be back on the three-way prowl together."


I’m a 19-year-old female, I’m currently with my boyfriend/soon-to-be husband. He is 30. First off, I just wanted to tell you I love reading your advice and I am hopeful that you can help me out a little. OK, here it goes: We are getting married early next year. We have been together for a year and some-odd months, so we know each other fairly well. We love each other and only have eyes for each other. He was my first boyfriend who I cared about and only my second partner.

He has had more partners than I have, and, from what he says, I am not that bad. Here’s the real problem: He wants to have a threesome with another girl. I do not mind this idea at all, because before we tie the knot both of us would like to experience a threesome for the first time. However, here is where I get all weird: The girl we’ve decided on is, in my opinion, much prettier then I am, and she has had a lot of "experience." I have no idea what I need to do to get this right, but I would like to make it a good experience. She has done other threesomes, while my boyfriend and I have not. I am sure he knows what to do, but I have no bloody clue!

I have watched a couple of pornos to see what they do, but mostly it’s just team blow jobs and rim jobs. Am I expected to do lez action? Am I supposed to lick her anus? Am I supposed to just nibble on her or what? I am really confused. I am kind of scared to do this now, and I already told him I would do it. What should I do? I love him and I want to do this, but I feel insecure. Is there a way to break this promise? Or maybe an instruction manual on having a threesome? I am totally clueless. Please let me know what you think. Thanks. —Confused Lady In Threesome

P.S. We have all been tested for STDs and HIV.

"It sounds like you’ve agreed to have a threesome to satisfy your fiance, CLIT," says Vicki. "I’d like to smack some sense into you. If you’re considering a threesome because your fiance pressured you into it or you’re hoping it will save a deteriorating relationship, you’ll probably regret it and resent your fiance later. A threesome can be really hot if you’re doing it because you want to. You’ve gotta wanna."

This three-way is only going to work if you’re doing it because you want to explore your own sexual curiosities. If you go into it merely to please your fiance, or if you mimic porn in an attempt to "do it right," it’s going to be a disaster.

"Threesomes offer a perfect opportunity for exploring bicuriosity with a nifty hetero safety net," continues Vicki. "But same-sex action isn’t mandatory. There are a million ways to get your three-way kink on. What turns YOU on about a threesome? What’s in it for you? Following your own turn-on is key to having a good threesome experience."

Vicki’s new book, The Threesome Handbook, contains everything you need to know about three-way etiquette, sexual technique for novice bicurious explorers, and tons of advice about communication and expectations. Please buy it and read it before you make another move, CLIT.


First, I want to thank Vicki for her three-way advice — thanks, Vicki. Second, I want to share a letter I received about a three-way success story. It’s about a gay couple’s explorations of three-way sex, but its lessons apply to any couple thinking about opening up their relationship. The letter is a little long — but, hey, this is the Internets, people, and word counts don’t apply here.

My hubby and I started dating about two and a half years ago, and sex was a huge component of our relationship. We were inspired by each other and very much in love with each other for nonsexual reasons, yes, but we were also passionate guys with conflicting opinions and approaches to people — we argued a lot. We both agree that what saved the relationship early on was the sex: Our appetites were perfectly matched, and we couldn’t fuck hard enough and often enough.

We’ve both had a lot of sex in the past, but with the future-hub, I discovered that I was getting off on his ecstasy just as much as I was on my own. The look on his face — deliriously anguished and feverishly overpleasured — whenever I’d fuck the hell out of him was more of a turn-on for me than anything my cock was doing inside of him. In the past, sex had been this sort of one-way experience — sure, I was making sure my partners were having a good time, but I didn’t get off on their pleasure more than I was getting off on mine. Shortly after I made this discovery, the future-hub announced that he’d made the same. And shortly after that, one of his exes — who remains a good friend — came to town.

We went dancing with the friend that night, and while grinding with each other in a playfully sultry little dance-floor three-way, I found myself turned on: I wanted the hub’s ex to kiss the hub, and, what’s more, I wanted to watch my hub get fucked by him. Much to my disappointment, nothing happened that night, but in bed at home, just the two of us, I confessed that I really wanted to see them get it on. This led to a discussion about three-ways, which we both had grown interested in trying, and it turns out for the same reason: Sure, it’d be nice to suck another guy’s cock or fuck his ass or get fucked by him, but what we were really interested in was stepping back and watching the other get it on with someone else.

A lot of our friends have had "open relationships," and we admitted that we couldn’t think of one open relationship that had worked. We thought about those relationships and determined that what had screwed up the open thing was a lack of mutual respect: One or both guys in the couple thought they were entitled to their thirds, their one-offs, whatever, and fought for their perceived right to fuck whomever they wanted, even when the partner they were supposed to be in love with was telling them, "Hey, this isn’t working for me anymore. Can we stop and re-evaluate?" We really didn’t want this to happen to us, but we were still turned on by the idea of thirds, so we set some ground rules: 1) We both have to be interested in the guy. 2) He has to be equally interested in both of us. 3) We can’t have a third when we’re not happy with and desirous of each other. 4) If either of us stops the encounter for any reason at all, it’s over and we send the guy home — nobody is in any trouble.

Our first three-way was pretty awesome in that it confirmed our suspicions: We did, in fact, like watching the other get pleasured by and pleasure another guy. The look on my lover’s face when he came in this guy’s mouth was just incredible, and even though I’d come a few minutes earlier, I was hard all over again. The guy thanked us for the fun, left, and we spent the rest of the afternoon fucking each other’s brains out to celebrate. Subsequent three-ways have had pretty much the same result: We have an awesome time fucking the guest, he leaves, and then we fuck each other all over again.

Now, we haven’t had a ton of three-ways in the two years since then — maybe five or six? — because we believe in quality over quantity. And twice we’ve each had sex with another person on our own. Our rule for "one-offs": We have to have guilt-free fun with the guy — otherwise, what’s the point? Also, one-offs are fascinating for us because not only are we enjoying the thought of our partner having sex with another guy (we tell each other in advance), and later enjoying the news about how it went, but we’re also turned on by our feelings of jealousy — so yay for cuckolding!

Sometimes we do feel a little threatened. I think that’s normal, especially when some guy walks into the room with something you don’t have that your lover frankly lusts after (great pecs, a beer-can cock, Jake Gyllenhaal’s come-fuck-me eyes). A hint of jealousy is a normal part of any relationship, I think, and in the "open" sexual arena, it can be really scary to try to manage because it’s there that one of the biggest reasons, if not the biggest reason, for jealousy in a relationship gets thrown right out into the open. In order to manage jealousy, you have to trust that your lover is telling you the truth about his feelings and actions, and you have to give your lover the same respect. What works for us in that department is that we don’t do it often, and that we really understand what happened and how we felt about it when it did, and we know that we don’t have to lie to each other about anything. My hub visited his family in Kentucky last week and I’ve got to admit that I was a little antsy about his absence — I thought he might’ve fucked somebody, and it made me a bit anxious to do the same. But I didn’t, and I trust him when he told me that he didn’t either. Though I have to admit that I was a little disappointed that he hadn’t!

Honestly, and the Christian Right would probably rapturously shit themselves with joy to hear a faggot say this about his somewhat open relationship (hey, as though we weren’t already sinning enough for them), but here goes: Three-ways and one-offs, in moderation, have helped strengthen our relationship. Sexually, we learn new tricks from these other guys. What we’ve learned being with other guys has played a big part in keeping our sexual relationship with each other hot. It’s crazy, but sexually we just keep growing. The occasional three-way, and the one-offs especially, add fuel to our fantasy life: We often reminisce about our hot encounters and relive the blow-by-blows together, and part of the turn-on involves our admitting jealous feelings as much as admitting to aroused feelings. It’s also strengthened our communication with and trust in one another: I know that he’s totally up front with me about his feelings, and he knows the same of me — about sex, and about other things, too. Staring down this big devil of trust has helped us manage the little things better. Having occasional sex with others also puts our relationship in perspective: Yeah, my hub might’ve gone out and had some nine-inch dick up his ass a week ago, and I’m definitely really turned on when he tells me about it and maybe a little more threatened by it than I’m letting on (as he is the hungriest bottom I’ve ever met in my life and I worry that I’m just not enough for him when he talks about wanting a monster dick up his ass), but there’s something really awesome that happens to me when he says to me, with my dick freshly up his ass, "Those other guys? A lot of fun. But what you do to me with your cock is fucking brilliant and I am so happy that I get to ride it for the rest of my life."

Love is about communication and trust, right? We argued a lot about social and political stuff early on, but we worked through that stuff, and managed to build something strong and resilient. We don’t fuck around often, but when we do, it actually has a constructive role in our lives, it’s something we really enjoy together, and we sincerely feel like it brings us closer.

Is that cheesy or what? —Two Chicago Boys Send letters to