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I’m a 33-year-old woman in a relationship with a 43-year-old man. My boyfriend’s fantasy is to have a threesome with another man. He enjoys watching me have sex with other men and then intermittently fucking me. But he mostly likes to watch me get fucked. For a long time, my boyfriend would send nudes or videos of him fucking me to men we met on dating apps. We would talk dirty about it during sex. Recently, we met up with a man for the first time. I don’t think it went well.
My boyfriend and I have had conversations about my fear of contracting an STI. So before the threesome started, I explained to my boyfriend and the other guy that condoms were required. They both agreed. This guy was really nervous and when he put a condom on, he went flaccid. He would try to fuck me with his flaccid, condom-covered penis, but it just didn’t work. He would take the condom off, jerk off, get semi-hard, put a condom back on, go completely soft again. Even when I sucked the guy’s dick: nothing. (He actually told me to stop trying!) So my boyfriend, who was observing and jerking off, suggested we forget the condoms in the hopes this guy could stay hard. I said no and restated my boundary. The guy still couldn’t get it up, hopped out of bed, and started getting dressed. My boyfriend offered to let the guy cream pie me if he would stay. I said fuck no and the guy left. He didn’t even say bye.
I don’t know why the guy couldn’t get hard. But I certainly don’t think my boundary should be compromised because a stranger can’t get it up. My boyfriend keeps suggesting we meet up with this guy again so he can “get closure.” He really wants to watch this guy at least come on me. My boyfriend and this guy have since texted about him fucking me again. I’m all for being GGG, but … what the fuck?
I thought this guy was kind of an asshole. My boyfriend was definitely an asshole. My questions are: If I’m uncomfortable during a threesome, how do I politely call it off? I don’t want to embarrass anyone, but this went on for two hours and the guy never got it up. How do I terminate a threesome without sounding like a bitch? —Threesome Obviously Dried Up My Pussy
To politely call off a threesome, TODUMP, all you gotta say is, “Hey, this isn’t working for me—let’s take a rain check.” Say it while pulling up your pants and use your “final answer” voice.
And the “rain check” thing doesn’t have to be sincere. It can be, of course, if you’re interested in trying again sometime, but it doesn’t have to be. The “rain check” thing is mostly a nice, polite, face-saving, ego-sparing way to ease someone out of your pants/bed/playroom/apartment/whatever. And if anyone starts arguing with you—if your third or your primary partner starts arguing with you—don’t worry about being polite, TODUMP. Go ahead and be a bitch: “This is over, you/they need to go, rain check rescinded, asshole/assholes.”
And while we’re on the subject of terminating things with assholes, TODUMP, you need dump your incredibly shitty fucking boyfriend immediately—and there’s no need to be polite about it. Fuck him. Your boyfriend tried to coerce you into having sex without condoms when he knew you didn’t want to; you consented to having a threesome on the condition that condoms be used. Attempting to reopen negotiations about your stated boundaries once the threesome was underway was a violation of your consent. And your boyfriend knew you wouldn’t want to embarrass anyone and maliciously attempted to weaponize your consideration for other people’s feelings against you! Can’t you see that? He was hoping you wouldn’t embarrass him by refusing to have sex without condoms after he “offered” to let this guy cream pie you (come inside you) to get him to stay! He was hoping you’d rather risk an STI than risk embarrassing or contradicting him! And on top of that, he spoke to this guy like it was up to him—up to them—what happened next, like you were a Fleshlight or tube sock or something!
And now your asshole boyfriend is pressuring you to get back together with a guy who couldn’t get it up with a condom on when he knows you don’t want to have sex without condoms? A guy who couldn’t be bothered to say goodbye after you sucked his fucking dick? And your boyfriend is claiming you owe him (or them) closure?
This relationship should have been over the moment your boyfriend made it clear some stranger’s dick was more important to him than your health, safety, and boundaries. In that moment—that moment he attempted to barter away your boundaries—he proved he can’t be trusted and you aren’t safe with him, TODUMP, alone or with a third.
This is every woman’s nightmare scenario when it comes to cuckolding or hotwifing—that her boyfriend or husband will pressure her to do things she doesn’t want to do during a sexual encounter with another man. Guys like your boyfriend not only don’t deserve to have GGG girlfriends or their fantasies fulfilled, they ruin things for other wannabe cucks, stags, and hot husbands. He not only deserves to be alone forever, TODUMP, he deserves to be kicked in the balls forever. —Dan Savage
One of my closest friends kissed me while very drunk, told his female partner, and now he’s not allowed to see me anymore, even in group settings. (I am also female.) I understand that cutting off contact is the universally recommended first step after someone cheats, but considering how close we are as friends, it is heartbreaking to think I might lose him over this one incident. We are former coworkers and we’ve been close friends and regular drinking buddies for 12 years. Nothing has EVER happened between us before this one very drunk night. We ended up making out on the sidewalk outside of a bar and exchanged a few semi-dirty text messages later that night, which—unfortunately for all of us—his partner saw. He thinks we just need to be patient and one day we’ll be able to pick up our friendship where we left off. And while I know he needs to prioritize his partner now, I’m scared that we actually won’t be able to stay friends after this. Do I just swallow my sadness about the likelihood of losing a best friend over a relatively minor infidelity? Or is there anything I can do to help the situation? FWIW: I’m in a happy open marriage and have never once tried to initiate anything with him. I’ve never been attracted to him before and wouldn’t want anything to happen between us again, anyway, even if the kiss was hot. Complicating matters, my friend wanted to re-raise the possibility of opening up his relationship with his partner, which he insists has nothing to do with me. (My friend is male and his partner and I are both female.) —Friend With No Benefits
Hmm … I have a hunch you were something of a sore subject before this incident, FWNB, however isolated. If the text messages your friend’s partner saw confirmed fears she’d already been told were irrational, your exile is likely to last as long as their relationship does. But take heart: If your friend decides to reopen discussions about opening up their relationship in the wake of this incident, your friend will likely be single again soon. If they do manage to stay together, FWNB, the only way to get back into her good graces—and back in your friend’s life—is to gracefully accept your exile. (Going to her and saying, “It only happened because we were so drunk!” isn’t quite the slam-dunk you think it is, seeing as you and her boyfriend are drinking buddies.) It’s a paradox, I realize, but if she sees that her boyfriend is willing to cut off all contact with you to set her mind at ease, FWNB, she may be willing to give your friendship her blessing down the road. —DS
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