How to Do It

I Have a Wild Plan for My Fiancé on Our Wedding Night. It Involves His Ex-Girlfriend.

A man and woman being intimate, with a female figure hovering over them.
Photo illustration by Slate. Photos by Getty Images Plus.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

I know this sounds insane and probably fake, but I can’t get it out of my head and need some kind of reality check, if not your guarded approval to move forward.

My fiancé (straight man) and I (newly out bi woman) are getting married near the end of this year. We’ve been together for almost two years, and it’s been an incredible sexual awakening for me. Basically, I was raised in a very conservative, sex-negative home and felt so much shame about sex as a young teen (my mother caught me masturbating and told not only my father and siblings, but also extended family, friends, and members of our church) that I totally repressed my desires and actually thought I might be asexual for several years. I was also on high doses of a couple of medications known to lower libido. Shortly before I met my fiancé, I switched meds under the guidance of my therapist and doctor—and learned I’m definitely not asexual. Then I got together with my fiancé, who has been a pretty much perfect match sexually for me in terms of our fantasies, turn-ons, boundaries, etc. When I finally admitted to myself that I was bi, he was super supportive and gave me space to explore without acting threatened or creepy. We’ve had a couple of threesomes with women I met, which were fun for everyone involved.

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Here’s the deal: I’ve known since almost the start about his ex, “Anne.” She was his “once-in-a-lifetime sex” relationship before I came along and gets a lot of credit for helping him become the guy who now rocks my world in bed. They broke up amicably and have remained friends—not close-close, but they’ll like each other’s posts. I am not jealous; that’s not what this is about.

On the contrary, after having heard about some of their sexual escapades and checking out her pics on Instagram, I’ve been fantasizing about her. A LOT. (She’s bi too.) I’ve hinted about it to my fiancé, but he has no idea that she’s at the center of what’s been my go-to fantasy for a few months now. Basically, it started out as a threesome fantasy, became a cuckquean fantasy, and has evolved into a full-blown scenario in which she attends our wedding and essentially steals my fiancé/husband from me in front of everyone at the reception (taking the first dance with him before dragging him off to bed, me following behind like a puppy). It gets weirder from there, but you get the gist.

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Obviously, I don’t want this to come true. But I do want to invite Anne to our wedding. If we did, I would want to float the idea of her joining my fiancé and me in our “marital bed” on our wedding night. I feel very sure I wouldn’t be jealous, and it feels like it would be a way to make the night memorable and fun. (Since we’re not very “romantic” as a couple, I’m not expecting our wedding-night sex to be all fireworks and flowers; I’m pretty sure it will be just like the sex we usually have, which is wonderful, but not “special.”) Assuming she was up for that, I would raise the idea of her lightly cucking me too. Can I bring this up? If so … how?

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—Red Wedding

Dear Red Wedding,

Thank you for the disclaimer, but this is hardly the most out-there letter I’ve seen sent in to this column. It’s practically quaint compared to some. No offense! You transgress great, I promise.

My immediate reaction is less to the uniqueness of your scenario and more to the clarity with which you describe it and the confidence I feel that you are pointed in the right direction. I see no reason to avoid bringing this up with your fiancé. You broke tradition when you agreed to nonmonogamy, and there is no need to bust out the Scotch tape to put it back together for the sake of having a “proper” wedding night. Float it by him cautiously. Keep in mind that because the wedding night is such a momentous occasion in our culture (and many others), even he could be freaked out or otherwise not interested. Be prepared to accept that.

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The same goes, doubly, for “Anne.” Your fiancé knows her better than you and can advise on proceeding, if he’s down. Depending on her sensitivity, just asking her might be too much of an imposition and dash any chances of her joining you in a less-storied scenario. Making this request amounts to playing with fire, which means the payoff will be that much sweeter. And even in the worst-case scenario, in which you offend her and turn her off permanently, you still have the option to meet more women and play with them. It might not be on your wedding bed, but I’m sure that there’s a nice girl out there to cuck you yet.

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Dear How to Do It, 

Do men take Viagra for masturbation? My boyfriend, who’s in his early 50s, bought some from an online company late last year. I was surprised because he’s never had ED issues before, but I didn’t press the issue because he is getting older and maybe he’s feeling like he needs some help, or maybe he just thought it would be fun. We’ve had sex occasionally with it and it’s fine—he gets a lot harder than usual—but it doesn’t really make it noticeably better for me. If he likes it, though, I have no problem. We also have sex without it with no problem.

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Here is my quandary: He says he only takes them with me. But I was out of town this weekend visiting friends and came back to find in the medicine cabinet that one of the pill packs was ripped open and one pill was missing. This was not the case in the cabinet before I left. I don’t know what to think. He says he would never cheat on me. But why the heck would he take Viagra while I was out of town except if he was sleeping with someone else? Do men use it to masturbate? Is that like an actual thing? I don’t want to accuse him of anything and pick a fight that may destroy our relationship but I just don’t get why he’d take a Viagra when there was no chance of having sex with me because I was out of town. He doesn’t behave in other ways that indicate cheating (no secret phone behavior, and obviously he didn’t care that I might notice that the pill pack was open if he left it there in the medicine cabinet that we share.)  Am I an idiot? What am I supposed to think?

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—Dick Pill Confusion

Dear DPC,

It is conceivable that someone might take an ED pill to jerk off (perhaps for no other real purpose than to try it out), but I did run your letter by my go-to urologist source, Charles Welliver, director of men’s health at Albany Medical College, and he told me he’d never heard of someone doing such a thing.

Still, look: Your boyfriend removed a pill from the blister pack in your absence. That’s traceable behavior and yet it seems he made no move to conceal it. A smarter move would have been to remove a pill or two from the previous blister pack as he cycled through to create a secret stash. Then the absence of a single pill would have been more difficult to detect. But instead, he was practically blatant about it, which makes me think he deserves the benefit of the doubt.

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Still, look again: I’ve been wrong before when I’ve advised giving a man the benefit of the doubt. He could be assuming that you aren’t paying that close of attention, or he may not be considering your attention at all. You’re closer to his mind than I am, so I think you can assess his potential motivation and likely course of action here better than I could. If he’s otherwise not being sneaky, just ask him about it. I don’t think you have to pretend you didn’t notice and if there is a reasonable explanation, he will be able to convey it without flinching. Good luck.

Dear How to Do It, 

My boyfriend of three years broke up with me a year ago. It was both unexpected and not—things had been rocky, but I was also deeply in love with him, and he was still in love with me when he ended it. We had an amazing sex life: frequent, creative, and with space to be sweet or nasty depending on our moods, with shared mild kinks and interests. And from a purely physical standpoint, he had the perfect dick for my body. He told me on multiple occasions that I was “the best sex he’d ever had,” so I thought it was going OK. I slept with a wide range of people before we met (and since the breakup), but no one yet pushes my buttons like him.

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I find myself thinking a lot about something he said in the last month of our relationship: “You’re a lot of work to have sex with.” I worry constantly now that my preferred sex is secretly hard labor for partners, or that my body is too hard to make come, or not desirable. This has been surging in tandem with a huge downswing in my body image, and I don’t know how to tell if I’m being unreasonable with sex partners, or how to stop thinking about it in bed. How do I figure out if I’m treating my partners selfishly, and how do I start having great sex again?

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—High Maintenance

Dear High Maintenance,

Try not to let one comment that came late in a relationship revise what you knew to be true for years. Language is imprecise, especially when it comes to sex, which is communication that often transcends the spoken word. The experience and what you felt is, I think, far more definitive than some tossed-off critique that a dude said as he was (presumably) preparing to break it off with you. He may have said it, in fact, to hurt you as a primer to the imminent fall of your relationship or even to turn you against him so that you’d call it off or at least become so reactionary and upset as to be easier to break up with. You just don’t know.

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There is also absolutely nothing wrong with being “a lot of work to have sex with.” Any generous partner understands that different people have different interests and needs. Some people orgasm more easily than others, and some never do. Some people require more attention and care. That work becomes untenable, though, when someone realizes their heart isn’t in it. Perhaps whatever effort went into your sex didn’t feel like work at all for the first 35 months of your relationship, but then when your ex had checked out, it did.

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Even if none of the scenarios that I presented accurately reflect the situation, the fact is that comment that’s vexing you so much is one man’s opinion. Nothing more, nothing less. You’re better off not putting stock into it. As far as selfishness goes, just make sure you’re being considerate and putting in the work as well. If you’re really so in the dark about what you’re bringing to the table, think of it in terms of division of labor: Are you pulling your weight? Are you actively focused on your partner’s pleasure and doing roughly the same amount of work to achieve it? If yes, then you’re fine. If you hear from a range of partners that your demands are unreasonable or overly particular, OK, maybe it’s time to reassess. But if you had amazing sex with one person, you can have amazing sex with another. Try to stay out of your own way and approach sex as you did in your peak period with your ex.

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Dear How to Do It, 

My wife and I (both straight) have a wonderful marriage. We have great communication and regular, great sex. Over the last year, we’ve been talking about opening the marriage just for fun. I’ve been her only lover, and I like the idea of her exploring what it’s like to be with other men. Meanwhile, I have a strong sex drive and simply like the idea of having more sexual interactions with others. Recently, my wife suggested to a mutual friend, “Julia,” with similar views about open marriages, that she would be her choice for me, should we decide to proceed with our plans.  I’m perfectly fine with that; Julia is attractive, a trusted friend, has a strong sex drive, and we have great chemistry. Julia’s husband isn’t interested in sex as often as Julia would like, so she has been proposing to open their marriage for some time.

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However, there’s one issue: Her husband remains mildly open at best but mostly hesitant to the idea of his wife being with someone else.  He isn’t interested in seeing other women either. Of note, he doesn’t know about our chemistry. Any tips to help Julia educate her husband in a way that would help build trust in her own marriage?

—Hopeful

Dear Hopeful,

The hesitancy of Julia’s husband is not necessarily a product of ignorance. It’s true that the more a person thinks about an idea, the greater the opportunity is to spend time understanding it, and consequently, the less scary it may be. But that’s just one of several potential outcomes. It would be foolish to invest in the notion that all he needs to be cured of his wariness is The Ethical Slut. He just might not be cut out for an open relationship, and any pressure there is only going to make the situation more fraught.

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Julia should respect her husband’s sensitivity, because it will dictate boundaries if their relationship is to remain harmonious. The most you can do is to ingratiate yourself to the husband. In the event that he turns more open-minded on opening up, you want to set yourself up as a good guy who won’t harm his relationship. But the process may be painstaking, and the effort may prove to be in vain. Pursuing someone who is actually available at the moment would likely be a way better use of your time.

More How to Do It

My husband and I have an amazing relationship, and I love him deeply. A few months ago, at my suggestion, we started trying threesomes (with another woman) and have really enjoyed it so far. It’s brought us even closer—it’s given me a chance to explore that side of my sexuality—and it’s been a really fun and positive experience. That is, until recently—when he broke one of our rules suddenly, right in front of me.

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