I am a 36-year-old straight man, blissfully married to my 34-year-old 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. Two years ago, 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. All bases covered, 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, gone forever (I thought), 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. So at least the dick works. 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.
Heartbroken Dom
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 e-mail 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.
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
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 okay. 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.
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.
Thanks, Dan! Thanks for your column and your positive impact on the sex lives of people around the world.
Satisfied Girl
My pleasure, SG, and thanks for sharing!
Find the Savage Lovecast (my weekly podcast) every Tuesday at thestranger.com/savage.

The way HD talked about planning every move (and reaction?)of the 3-way just reeks of insecurity (as every controlling person exudes, in my experience); all that planning and then something unexpected happens… oops! Maybe he and his wife could do a switch in the D/s roles for a session and see how that works out. All I know is, whenever I try to control my life, it comes back and bites me in the ass (so to speak)… the need to control everything comes from fear. Letting go of all control as a sub to your wife once or twice could be enlightening!
Get to it, Photoshoppers! And send me a t-shirt.
I’ve been involved in group situations where everything up to intercourse is fine, but something about the sight of my partner having full-on straight/hetero intercourse with another person freaks me the fuck out. It’s normal, and it’s ok to stop.
Being a melodramatic bitch isn’t ok.
HD really should have storyboarded everything first. I hear that’s what the Coen brothers do.
Why does it matter that ASS is a rent boy? Three wasn’t paying, and he wasn’t lied to about anything of substance. Just be as friendly as you would otherwise be, ASS, the next time you see him. If he brings up the other night’s sex, you can just agree that was a fun time, without committing to more. Why does someone get to act “hurt or confused” just because a one-time sex partner is not interested in another go at it?
@5: That’s a good point. Fucking someone you just met does not imply a commitment to more fucking in the future.
Random sex is random.
whoops, two-time. But still. What happens at the resort, stays at the resort.
ASS wants to come clean with Three because he doesn’t want to be slick with someone with whom his relationship isn’t his first priority. That’s why I say the persistent principle in Dan’s advice seems to be that you can be slick in your relationship if it’s your first priority, you can make your relationship something other than your first priority if you aren’t slick in it, but you can’t be slick in a relationship that isn’t your first priority.
Omg, I can’t believe I’m just No. 7. And I can’t believe I’m gonna grammar-pick the amazing Dan Savage — and I’m sure I’ll get skewered for it — but … In Dan’s first response, the phrase is actually “champing at the bit,” not chomping. It’s what horses do when they are anxious or excited, and “chomping” is a common misuse of the phrase.
That said, that one incorrect little vowel is about the only thing I have ever found wrong with any of Dan’s column.
Heartbroken Dom sounds like a fake letter to me – but the writing style made me laugh.
ASS’s client sounds like a jerk, but Three must have known something was going on and he fell for it, so there is blame to go all around.
If it ever comes up where Three comes sniffing around for more sex, ASS should just tell Three that he is cockblocked or something. Tell him he thinks fooking (typo, but it works) around again with Three behind the (unbeknownst) client’s back would make things too tricky (unintended pun, I’m on a roll!) with the mutual friend/client.
“Unicorn guy?” Is that something the (20-something year-old) kids are saying these days? ‘Cause I like it.
Um. Before I get jumped on for the very thing I jumped on Dan for, I want to add an “s” to the last word in my comment. 🙂
Can we all please just stop with the candy coated euphemisms (rent boy, escort, companion, luggage lifter, etc) and just call these whores what they are….whores.
If you chose to make your living that way, I couldn’t possibly care less as long as you don’t do it in the street and scare the horses. But please don’t posit yourself as something you’re not. You’re not good conversation. You’re not good company. You don’t move equally as well from a leather jock strap to a tux.
I am so sick of people bringing these mental midgets to dinner or otherwise social settings and expecting the rest of us to ignore the elephant in the room. Mainly, that he’s there only because you’re paying him to be.
How in the world can someone who has a “normal” (for lack of a better word) job and relationships be expected to have anything in common or grounds for conversation with these jokes. I’m sick of it. Everyone that I know who has had to suffer one of these twits is sick of it.
And from this letter, both the whore and the john sound like complete and total creeps. The day after, when he’s betrayed someone’s trust in one of the worst ways possible, he develops an attack of conscious. How fucking convenient.
Hopefully Three didn’t catch something from this shore ditch that can’t be treated.
Word usage nazi @9: As a fellow word usage nazi, I must beg to differ. “Chomping” is just fine too. It’s a matter of dialect. “Champing” and “chomping” are both onomatopoeic and mean the same thing.
HD – sorry, but no sympathy here. You and your wife had something really good, but then you decided that no matter how good it was, it wasn’t good enough. You basically got greedy and overreached, and now you can’t un-ring the bell and go back to the way things were. That’s what happens when you play grown-up games: sometimes they take us by surprise and show us that we don’t know ourselves as well as we thought. You literally made your own bed, so now lie in it and stop complaining.
@15 I call sex workers whatever they want to be called. And I have enjoyed having dinner with the ones I have met, at least as much as I enjoy dinner with the lawyers I dine with more frequently. That’s not a high bar to pass, of course.
@15: Anyone can have something in common with anyone else, regardless of how either party makes their living. Does getting paid to fuck preclude good taste in music or art or a genuinely kind personality or sense of humour? No. But whatever the hell you do apparently does.
amen.
@15: When friends bring sex workers to important social events and expect you to make awkward conversation, that’s a reflection on your friends, not sex workers in general. Do not hate on the sex workers who are just doing their job. Hate on the “friends” who have the poor taste to subject sex workers to awkward conversations with stuck-up trolls like you.
@10: Heart-broken Dom in not a fake letter. Sad to say, I have Dom friends who talk just like that 🙂
p.s. I’d like a ‘Dan Savage is my rabbi’ t-shirt.
@15: Actually, the whores/rent boys/escorts/etc. I’ve met are pretty interesting people. When your job is to be interesting, it’s unsurprising that you become good at it. My sense is that the ones you meet are keen to your overwhelming sense of moral superiority, and don’t waste their time trying to charm you.
You want mental midgets? Try going to any function that involves inherited wealth. Those fuckers not only don’t know shit, but they’re too stupid to know that they don’t know shit. When everyone around you is kissing your ass, you don’t realize that you’re a twit.
I figured that my comment would bring on a shit storm of criticism, and I’m prepared for that. But until you’ve been forced by work politics to have dinner and interact with people who should aspire to vapid, you’re really in no position to criticize.
Personally I believe in the sovereignty of the individual and I think prostitution should be legal. But let’s be honest. As a rule, they’re not the “hooker with a heart” that you see in movies, or the educated socially graceful geisha of times past. If you seek the company of a “sex worker” (is that better?) good for you both, but just keep it behind closed doors.
@ 15, I think what we’re sick of is airheads. sex workers aren’t necessarily airheads. I actually find it”s hair extensions and constant gum chewing that are usually the better indicators of intolerable people.
@1 Penetration WAS planned. He was just freaked out a bit. Whatever. He wasn’t built for 3-ways. He needs to get over it.
But, I have this amusing image in my head of his wife petting him saying he was a brave boy…like a parent to their kid getting a shot from the doctor.
@15 Most idiotic comment ever. OK, not really…but, it was truly pointlessly self-aggrandizing to the point that nobody should want to meet you.
@15 Your mistake, of course, is to generalize – painting a whole category of people with the same brush. I suspect you know better and that you’re yanking this thread. But since I started, I’ll finish: I used to be a hooker. I’ve been paid to piss on people and masturbate in public. I also have a college degree and have had other careers. I have enjoyed conversations with a Senator, a 4-star General, and world-famous conductor. I once rode in an ambulance to the hospital with a complete stranger because she was scared and had nobody to comfort her. I have had my letters published in the New Yorker and the New York Times. I have spent days in the museums in Paris, Madrid, Florence, and Amsterdam. I have spent nights in jail for protesting against the government. I’m neither a genius nor a neurosurgeon. I’m just a human being with a point of view. And I really enjoyed being a hooker.
Geez, you all are being so effing hard on HD. Can’t a twentieth century dude express fear and anxiety at this point? So maybe he’s got some insecurity issues. So maybe his trio should have started smaller, and worked their way up to full intercourse.
But have some sympathy for the guy. You can plan your actions and even the actions of consenting others but you can’t plan your own reactions, especially your own emotional reactions. I’m sure we all know the feeling of “the air being sucked out of the room through your soul,” like when you see your ex, whom you’re still trying to get over, with their new lover.
What I would say to HD is to be eternally grateful that your friend and especially your wife were so sensitive to your needs during this fiasco. Your wife knew that you needed to feel sexually adequate so she made love to you the next morning. So thank her by trying again, with baby steps.
Based on all the words like “many conversations,” “expectations,” “stipulations,” “mentally prepared,” et cetera, I’m guessing that HD was never really into the idea of involving another man in his wife’s sex life in the first place. Rather, he got talked into it over the course of the last two years, and all those “stipulations” were around making him “comfortable” (interesting that that particular word was absent) with something he didn’t want. Chances are pretty good that the idea was sold to him under the banner of being the Dom, to persuade him that he would at least be in full control — hell, it would be happening at his command, so he could hardly claim it was against his will. Likewise his wife calling him “brave” tells me he probably had reservations the whoe time, and everybody knew it. (@26: that was just mean.)
Wonder of wonders, when it actually happened, he couldn’t deal with watching it happen. Gee, who could have predicted?
First, the lesson: don’t agree to something that you are deeply uncomfortable with. GGG does not translate to violating your own boundaries for the sake of the other person. Push the envelope, yes; rip it in pieces and toss it in the trash, no. If anything, if the last two years played out the way I’m guessing, his wife should have concluded that his feelings on this subject indicated a likely unhappy ending, and not pursued it. Instead, he’s had two years of wondering “Why does she want this so much? Why am I not enough?” and the act itself merely confirmed every one of his fears.
@5: You really don’t see any difference between thinking you’re fucking someone based on your own merits and fucking a professional sex worker because they’re being paid?
Seattle just seems weirder and weirder every time I visit this site.
I’m not sure what to suggest going forward. I don’t see those insecurities going away meekly and gently of their own accord at this point, whether or not they close the relationship back down.
I’m inclined to say that his wife owes him a MFF with another woman friend who displays at least as much interest in fucking him as his wife displays in fucking someone else.
(I have to admit, part of me wants to call the letter a fake, purely on the detail about not being big enough. Isn’t that a classic cuckold fantasy fetish detail?)
Ok, I give up. What’s a unicorn guy?
i’m super glad dan called HD out on the super DRAMA. sounds more like a whiny 18 year old boy rather than a 36 year old man.
at 33, i wanted to know that, too–thanks for asking
i’m guessing “unicorn guy” means he’s such a rare type that most people don’t believe he exists.
not to be confused with “Unicron guy”, a guy whose drama and issues literally consume your entire world.
Now I know what I need to add to my OkCupid keywords…
@24 I’ve been forced by work politics to have dinner and interact with people who should aspire to vapid. I’m talking about the sort of people who make sure you know they are global travelers and go to the sort of parties you wear tuxedos to.
To me, the very definition of a vapid person is someone who can’t figure out how to have an interesting conversation with a sex worker. That’s just how I define that term.
We all have people we find insufferably boring. You are on a lot of lists yourself. Do not be deluded.
I think in this context, “Unicorn Guy” was used ironically as the male who was not interested in a MFF 3-way.
@38 yes, we’re all on lists. Most of which we didn’t even do anything to get ourselves put onto.
@38: “To me, the very definition of a vapid person is someone who can’t figure out how to have an interesting conversation with a sex worker.”
I think I’m in love.
ASS as a Rent-Boy you were contracted to lure and bait Three into the threesome with your Client. I only see that Full Disclosure after the fact is what would ease your conscience of guilt or remorse that you may feel, having deceived Three. It’s either that or you would prefer that any future encounters that you may have with Three requires some type of Remuneration on his part as you’ve established that you are a Rent-Boy and that when you’ve received payment to play you don’t ever play in the future without pay.
I often wonder about Sex-Worker’s Protocol. Does the fact that you are getting paid give you and erection? Does sexual excitement only occur when you know that you are getting paid? If the sex is good enough do you consider freebies for any future sexual encounters? Can your economic needs be tossed aside by finding someone to aid in your emotional comfort? Is there ever a “Pretty Woman” Moment when the guy that you are with becomes your “Prince Charming”? Do you hold to strict categories for those who pay to play and those who are free or “freebie-d” and never betwixt the two shall meet? I don’t seem to understand at all because obviously there is sexual excitement and some type of sexual attraction or chemistry to one another. So the fact that the first and second sexual encounters had payment; one can only preclude that all future encounter must be paid for?
I think that you should do what you were contracted to do and keep your mouth shout! Be a good little Rent-boy and keep silent after all you don’t want to ruin any future potential clients that would hear that you were Loose with you tongue and not in a good way!
So, letter number one essentially boils down to “I freaked out when I saw my friend fucking my wife.”
Contrary to the people here who act like you have a problem, your reaction makes you like 99.9% of the straight, married guys out there. Maybe, just maybe, you got into something that your wife wanted, but you didn’t?
If you don’t want your wife fucking your friends, or if you merely don’t want to see it, don’t pretend you do. Tell her you are not into whatever it is you are not into.
HD is such an entertaining letter writer that in part one wants to pat him on the head and lead him gently to the Kiddie Pool. Then again, it might be great fun to see how he’d be received by an anti-patriarchy set.
But mainly I wonder about the friend. What sort of person would be able to get through agreeing to that overproduced scene and being dominated and directed by HD for more than ten minutes without yielding to an irresistible urge to tie and gag HD and then place him in the corner in order to get on with the matter at hand without further blathering?
I don’t wish the couple ill, but, unless the friend is as much a piece of work as HD, the friend and the wife seem much the better match. It would be helpful to know if the wife would call HD her soulmate; I can’t get a convincing picture of HD’s soulmate having brought the threesome about in the first place.
41 😀
Maybe I should have been more clear. I wasn’t saying that escorts (I’ll use the kindest term) aren’t good people and aren’t worth knowing. Everyone is worth knowing.
When they’re off the clock.
I”m sure that @27 could probably talk circles around me regarding many topics.
@38 might be right. There might be people who find me a bore. No worries. No one is for everyone. It’s not that I’m incapable of finding some common ground for discussion with nearly anyone. I just choose not to. My right. Just like escorts can chose to not speak with me if I’m unwilling to open my wallet.
I do find it interesting that so many people are so eager to jump down my throat for expressing an opinion. I didn’t criticize a characteristic that’s beyond someone’s control. I’m sure there are people who are in this line of work because they simply feel they have no other choice. But every one that I’ve ever met did it because of pretty shallow, vapid and lazy reasons. And if you’re going to be a hooker, then you better be prepared to have people think of you as such.
“sounds more like a whiny 18 year old boy rather than a 36 year old man.”
Yeah, because if he doesn’t behave as you prefer, his manhood is void, right?
God, I hate that sort of name-calling: A woman likes sex? She is not a woman, she is a WHORE! A man acts in ways I don’t like? He is not a man, he is a BOY! You don’t agree with politician X? You are not a decent person, you are a nazi/socialist/bee-keeper/etc!
Stop denying people’s basic human status as a man or woman just because they don’t toe your utterly immaterial, wholly subjective lines.
@36 Thanks for the Transformers reference!
@30, people get into bed together for a million million reasons. Once I’m in bed with someone, I enjoy myself and try to show the person a good time, regardless of who is paying whom in what kind of currency.
If I have a gourmet dinner at a friend’s house cooked by a chef, I don’t care if the chef did it for friendship or for money. I respect their craft and enjoy myself.
Global Traveller….I know you retracted…but I had to chime in here as another woman with a “past”. Although you would never know it know (just a bit of suburbia these days, along with my two, yes count them TWO graduate degrees), I used to do sex work as well in my youth.
But, I assure you, with a client, I doubt you would have even been able to spot me as such. I blended.
Perhaps I was your hooker (or S/M worker, lol) with a heart of gold? Or very intelligent, well educated one at least, able to converse on many a topic….and yes, I will agree with the above poster…I would bet sex workers can tell some *amazing* stories….much more so then the typical “how big is your bankroll” bragging of corporate yawners.
@16 I don’t think nazi means what you think it means.