Q: I am a 36-year-old straight man, blissfully married to my soul mate. We have explored and enjoyed each other for a decade now, and we recently started exploring BDSM and D/s fantasies. Everything was going great sexually—until last night. My wife expressed an interest in an MMF three-way, where I was the Dom guiding the action between all three of us. I planned this event, play by play, reviewing in my mind everything that was to take place. There were many conversations about expectations, stipulations, etc. I went into the event mentally prepared and gleefully excited. Magic happened for about two hours—passion, love, and dirty, dirty sex. Almost every kinky kind was being had and enjoyed save vaginal intercourse.
Then my wife was vaginally penetrated by our friend.
It was as if all the air in the room was sucked out through my soul. I instantly lost my bone, and I felt angry and nauseated. I had to stop the scene. My friend and my wife instantly tended to me during my breakdown. The sorrow of disappointing my wife hurts the most, even though she calls me brave for this. I don’t feel brave. I feel confused. I had planned how everything was going to happen. I even gave the fucking command (literally) for my friend to enter my wife. Crushing emotional pain followed.
In the morning, my wife woke me and made love to me, tenderly and healingly. I am still beset by all manner of doubts and insecurities. Is my dick big enough? Am I good enough for her sexually? I feel scared and trapped in a land that I have never visited before, a land called Insecurity.
A: You’re clearly in pain, and I want to be sensitive to your pain … but … your overwrought prose style has me wondering if you’re enjoying this drama a bit. Maybe that’s just the way you talk—maybe you always sound like a Brontë sister after a three-day bender—but there’s a self-dramatizing, self-aggrandizing tone to your email that gives me pause.
I’m not saying that your distress is an act or your pain isn’t sincerely felt, HD, but your meltdown effectively ended a scene in which all attention was focused on your wife and started a new scene in which all attention was focused on you. As you wander the heaths of Insecurity, I’d encourage you to examine your own subconscious for evidence of drama queendom.
That said, HD, sometimes three-way reality is a lot more emotionally charged and challenging than three-way fantasy. Let your experience be a lesson for others: If there’s a sex act—say, vaginal intercourse—that holds huge symbolic importance for you or your partner, it might be best to take that act off the menu. Take things slow the first, second and third time, invite your guest star to participate in some lower-stake/lower-significance sex acts, but reserve the main event for yourself.
Perhaps you didn’t realize how shattering it would be to watch this man bone your wife until the moment that he—at your command—boned your wife. Like they say: Hindsight/sex-advice columnists is/are 20/20/a bitch.
How do you get past this, HD? Only the passage of time will lead you out of Insecurity. You’ll come to believe that, yes, you are good enough for the wife sexually because you’re going to keep having great sex. You’ll come to believe that she’s content with you when you close your relationship and she isn’t chomping at the bit to fuck other guys.
Q: I have a rent-boy etiquette question. Recently, a client of mine, who lives in another state, invited me to join him at a resort where he was meeting up with friends. This included a nice-looking man who lives near me, whom I will call “Three.” My client has been lusting after Three for a long time, and my job was to act as bait to lure Three into a three-way with my client and me. Things went really well, and the desired three-way happened on Saturday night and again on Sunday morning.
Here is the problem: I don’t think my client informed Three that I was there in a professional capacity. So from Three’s perspective, I sought him out, flirted shamelessly, and had really hot sex with him—twice. So it would be pretty jarring to him that, the very next day, I’m suddenly not interested in him. It goes against whore protocol to “out” a client, and I suspect my client did not want Three to know I am a rent boy because that might have been a deal breaker.
I would feel pretty stupid if I thought a man was really into me, only to later find out he was just doing his job. Three’s feelings are bound to be bruised. I don’t know what to do. I want to be respectful of my client’s confidence, but I don’t feel comfortable tossing Three aside like a used tissue. There is a real possibility that I will be seeing him in the future, since we move in similar circles or the next time my client comes to town. Is this my client’s faux pas, or is there some rent-boy protocol I should have followed?
Awkwardly Socializing Soon
A: If Three didn’t know you were a rent boy, ASS, and that you were being used as bait, then Three’s consent was obtained under false pretenses. That’s not OK. And as you knew going in that you were being used as bait—that it was your “job” to get Three into bed—you were an active participant in this deception.
You’re a rent boy, ASS, not a rent bot—you don’t have to do everything a client asks. You could have agreed to flirt with Three, but you should have insisted to your client that your employment status be revealed to Three at some point between flirtation and fellatio.
Considering the circumstances, ASS, I think you can be released from the bonds of strict client confidentiality on this occasion. If you run into Three, and he seems hurt or confused, let him down gently. Tell him he’s an attractive guy, tell him you enjoyed the hell out of those three-ways—then tell him you were on a job and you’re sorry for not telling him sooner, i.e., for not telling him that weekend, before anything happened.
Q: I’m a straight girl who made a resolution to seek out a couple for a three-way. With my boyfriend’s full support—he’s the kind of unicorn guy who thinks three’s a crowd—I perused options online. One gentleman caught my eye because he proclaimed on his OkCupid profile “Dan Savage is my rabbi,” he described himself as “GGG,” and his lady friend was also a Savage lover.
We met up last night, and it was a beautiful, well-orchestrated event. Boundaries and excitements had been discussed beforehand, and three fun, sexy, fit twentysomethings had awesome sex. It was a perfect girl-girl-guy three-way. Great communication up front, great communication during, great communication after.
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