Hi! My name is Alex, and I just wanted to start off saying that my wife and I are big fans of your site. You may remember my wife (Sam) asking about the use of prostate massagers. We tried one that my wife picked up at the local romance store and I liked it a little bit. I think we may have gotten a cheap one, but it seamed to big. But my question today is different. My wife and I absolutely love eachother, but we like having threesomes from time to time. I know you two are a monogamous couple, but thought you might be able to help me decide. My wife was kind enough to invite another girl into the bedroom with us and we had an amazing time. Do you think its fair to invite another male into the room for a little guy on guy on girl action? My wife would find it interesting and I’d do anything to please her, but I’m not gay. I figured since I wanted my wife to try pegging with me, would the real thing be different? Is there anything I can do to prepare myself for taking it in the rear, but also being able to enjoy it? I’m lost and confused and I trust you guys with smart sexual decisions. Please help.

Mark A. Michaels and Patricia Johnson
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Dear Alex,We suggest that it’s better not to think of your sexual adventures with your wife (or indeed any of your sexual activities with her) in terms of a quid pro quo. Saying “would it be fair. . . ” indicates that you may see having a MMF threesome as a way to even some sort of score. If that’s the case, you should probably think twice. In sex and relationships, it’s generally not a good idea to think in terms of – “If I do this for you now, next time, you have to do things my way.” Rather, mutuality is the key, and that’s the case whether you’re monogamous or non-monogamous.There are countless ways for people to be sexual together (regardless of the numbers involved), so having a MMF encounter doesn’t mean you have to engage in sexual activity for which you feel even a little physically or emotionally unprepared. This is true regardless of whether you identify as gay, straight or bisexual.

Patricia Johnson & Mark Michaels
Co-authors of The Essence of Tantric Sexuality and Tantra for Erotic Empowerment

Dr. Charlie Glickman
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I think that there are a few different ways to answer this question. First, I think it’s totally fair to give your partner an experience she’d like, especially after she gave you one. But I also think it’s important to be sure that whatever happens, you’re doing it out of a desire to have fun rather than because you think you have to. That can lead to resenting the situation or your partner and in my experience, resentment is one of the biggest problems for relationships.So if you’re on board with a MMF threesome, great! But if you’re not sure about it, or if you’re not into it, you might want to find some other ways to give your wife a fun time.OK, so if you decide to go for it, you still get to decide what that means. Lots of people have threesomes where two people focus on the third instead of having much contact between them. Think of it as a V rather than a triangle. that’s important because you get to have your boundaries, too. For that matter, the other guy might want to focus on her instead of you, too.

Even if both of you guys do decide to give each other a little attention, that doesn’t necessarily have to mean anal intercourse. Oral sex, hand jobs, kissing, massage- those are all possibilities and they can be lots of fun. So don’t get stuck on the idea that you have to do anything you don’t want to do. For lots of excellent tips and sexy inspiration, check out The Expert Guide to Threesomes or The Threesome Handbook: A Practical Guide to Sleeping With Three.

If you decide to give anal intercourse a try, it’s not a lot different from pegging, at least in terms of the mechanics. However, it’s worth knowing that the ability to experience and enjoy anal penetration is strongly connected to your level of relaxation and arousal. If you aren’t turned on or if you’re feeling nervous, you might tighten up or you might not enjoy it as much as you could when you’re more excited. If that happens, don’t stress about it. It could be nothing more than first-time jitters. Or it could be that you’re simply not attracted to men in general or this guy in particular. But the more you try to force it, the less likely you are to succeed, so keep the focus on having fun instead of engaging in a particular activity.

There are some great guides to anal play and they’re definitely worth checking out. Tristan Taormino’s Expert Guide to Anal Pleasure for Men covers all the important stuff and while it focuses on pegging rather than sex with another guy, the info is pretty much the same. I also like The Ultimate Guide To Anal Sex For Men. And there’s a lot of great info on the Good Vibrations website on anal sex and prostate play.

I can also recommend a few toys to get you started with anal and prostate play, like the Aneros Prostate Massager and the Naughty Boy Anal Toy. And don’t forget the lube and condoms.

Remember- the whole point is to have fun, so whatever you do, enjoy!

Cassie Wolfe LSW, MEd
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Dear AlexTotally digging your ability to keep an open mind. So rescue me if I’m not reading you correctly, but it sounds like you actually haven’t had the conversation with your wife about inviting another guy into your bedroom. While compromise and equality is sexy, fantasies are not created equally and cannot be universally applied. What I mean is, if your wife was cool fulfilling your (and maybe even her own) fantasy of having a lady person join, that does not mean that she has a fantasy of having another guy join. I’m also sensing that this request is perhaps coming from your own curiosity about having the “real deal” versus being pegged by your wife. Either way, whether it’s your fantasy, your wife’s or both of yours…communication is key!Sexual orientation and sexual identity also cannot be applied universally. Many folks are attracted to same-sex people’s fun parts but never actually play with them. Some are attracted and also play, but do not identify as gay, lesbian, bi or otherwise. What I’d offer is being less concerned with labels and more concerned about discussing ways to protect yourself from unwanted STDs (condoms!) and ways to have an awesome time trying something new. That being said, same rules apply to the real deal as compared to when your wife pegs…lubrication, lubrication, lubrication!!!! Start small (fingers) first…relax…and go slowly. If something doesn’t feel kosher, communicate that. If things feel amazing and you’re ready for 1 finger to go to 2…or ready to be penetrated by one of your playmates, communicate that and game on.

Dick of Dick-n-Jane.com
(layman with a website)
Alex – Let’s put the non-monogamy topic aside, it’s clear you and Sam already have an agreement that works. It’s also appears that you would like to leverage this agreement to explore new territory… specifically sex with another man. An MMF threesome present a wide array of possibilities, only one of which is male on male anal sex, and I get the impression this new activity was your idea not hers.From your description it sounds like you have limited experience with anal play but are ready to jump into a not-totally-hetero relationship with another man (for your wife’s sake and with her present so it’s not gay) for the purpose of taking it up the bum. You should consider the health risks for both you and Sam and that the man attached to the guest penis will have his own agenda and needs. By introducing another person to your sexual relationship you are inviting in much more than just an extra set of genitals… but you knew that already.My first experience with pegging (having Jane fuck my ass with a lifeless dildo) was a surprisingly profound and bonding experience. Sexual climax on the receiving end of penetrative sex is known to unleash unexpected emotional responses (something about connected neural pathways) and in my case it did just that. Sharing that experience with Jane, my primary [and only] partner, required both vulnerability and great trust on my part. I can’t imagine trying to fully experience the joys of receptive anal sex for the first time while also exploring with a new partner (be they male or female).

To be clear… pegging and sex with another man are not equivalent. My advice is to explore your prostate and anal curiosities with Sam, you will get more out of it. Buy some basic equipment if necessary and tread new ground with your trusted partner. If you still have the desire to receive anal sex from another man during an MMF threesome then do it, at least you will have already learned some things about your own sexual response beforehand.

If I were to slap a label on you, Alex, it would be “heteroflexible-curious” and there’s nothing wrong with that. If so, I would encourage you to be true to yourself and forthcoming with Sam. An MMF may be your fantasy as much as hers for reasons she should be aware of before the big date.