How to Do It

I’ve Been Married for 25 Years. One Night of Flirting, and I’m Ready to Risk It All.

This is the first time it’s happened in over a decade.

Woman looking up pensively with a hall pass sign floating above her head.
Photo illustration by Slate. Photo by Geckophotos/iStock/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,

My husband and I are our only partners. We are in our mid-40s and have been together for 25 years. As in all longer marriages, ours has had ups and downs, but we are each other’s best friends and have worked through our marital issues, sexual and otherwise.

Recently, and unexpectedly, I had an encounter where a man flirted with me. It sounds absurd, but this was the first time this had happened to me in over a decade. And it was intoxicating. I have no way of contacting this person, so there is no possibility of anything further. But I cannot stop thinking about him. I cannot let go of the idea of a sexual encounter with someone else.

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The intensity of my feelings about this suggests to me that either I am incredibly attention-starved (we have two teenage children and my husband, while a wonderful person in many ways, has taken something of a “benign neglect” approach to the entirety of our partnership); or that I am just now realizing what I missed out on by signing up early for a lifetime of monogamy. What do I do? I am absurdly miserable at the thought that maybe I missed an opportunity to have sex with another adult before I die. Yet, I also understand that even mentioning the possibility of anything like an open marriage or “hall pass” poses a risk to a partnership I’ve spent my entire adult life building.

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—Distracted

Dear Distracted,

Given the quarter-decade span of your relationship so far, your friendship and mutual regard, and your two teenage children, the risks you mention at the end of your note are fairly significant. You also don’t know how your husband might react to the idea of opening up—it’s possible he’d be happy for you to have outside interactions and he might want some of his own. Only you can weigh these risks and potential benefits, and make the decision about what action you’re going to take.

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Do you have a close friend you can trust to keep quiet about what you’re considering? If so, schedule some private time to discuss this thoroughly with them. If not, several sessions with a therapist would be another good way to get some outside support as you sort through your thoughts. Making lists of pros and cons, journaling, or thinking while you walk or shower are other ways you can process your emotions and desires.

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If you decide against broaching the subject of opening up, it’s still worth having a conversation with your husband about his “benign neglect” approach. You question whether you’re attention starved. If you aren’t getting the physical interaction you need to feel intimacy and contentment, bring it up with your husband as a problem you’re hoping for his help in troubleshooting.

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Whichever route you go, proceed carefully. I think you’ve got this.

Dear How to Do It,

I’m a woman, married to a man for 11 years. I have realized in the last few years that I am bisexual and we’ve been discussing having a threesome with another woman. We are both very into the idea, but I need some help with logistics. I think I would prefer hiring a sex worker (it seems less complicated emotionally) but I’ll only be ok with it if I know the woman we hire is participating 100% of her own volition. My main concern is that I don’t want to exploit any person’s body for my own pleasure. We live within driving distance of Nevada where sex work is legal so I feel like that would be the best place to start looking. Do you have any advice on how to proceed with this or is hiring a sex worker inherently exploitative and a terrible idea for this?

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—Looking For a Third

Dear Looking For a Third,

Prostitution has been legal in the majority of Nevada—notably excluding the cities of Las Vegas and Reno—since 1971. So, you have several brothel options in Nevada. Wikipedia seems to have a fairly exhaustive list, arranged by county.

Generally speaking, hiring a sex worker is only as inherently exploitative as hiring any other sort of worker—masseuse, therapist, exterminator. The cruelty of capitalism impacts us all, and I doubt any worker in our economic system can truthfully say that they always do their work entirely of their own volition, without systemic coercion in the form of economic need. However, if you meet a sex worker who is telling you that they need help, please believe them and do what you can. Otherwise, it’s best to trust that sex workers are all making their own calculus of what they need versus what they’re willing to do to earn that money. Enjoy the experience that they craft for you.

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You might find this Thrillest essay about the hiring process at Sheri’s Ranch informative .
And this Money Diaries log from Moonlite BunnyRanch worker Alice Little can give you some idea of the economics of working as an independent contractor in a brothel.

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Many of the women who work in Nevada brothels advertise interest in female clients, or even specifically in threesomes with couples or first time experiences, and have contact information listed on their profile pages. Do your research online first—visit the brothel pages and look at the profiles of the workers—while making note of any questions you have about your trip. When you’re ready to reach out to a specific lady, let them know what you’re hoping for, tell her that it’ll be your first threesome, and ask any questions you have. Based on the brevity shown in your letter, I think you’ll have an easy time being concise in communications with your potential courtesan. You’ll want to strike a balance between clarity and respect for her time.

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Wear something that makes you feel comfortable. Have fun, call a stop to the action if it stops being fun, and bring enough cash for a tip. Enjoy.

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Dear How to Do It,

When my partner cums, it is a large amount, and it’s very watery. It’s to the point where we have had to research water sports gear because it’s basically the equivalent of peeing, and it was making a huge mess everywhere. I have been assured that he has been checked out medically, and there’s nothing to be done there… I have been with many other people before him, and I’ve never experienced such watery cum before.

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I can handle this in pretty much every way, except for oral sex. It literally feels like he is peeing in my mouth when he cums, and I’m just not into that. It’s also such a large amount that I have trouble swallowing it all. If I’m not ready, it can also feel like I’m drowning or choking.
This has really turned me off on going down on him, which I know disappoints us both because it’s something we both enjoy.

So what do I do to make this more manageable? I don’t want to take oral off of our sex menu, but I just can’t stand this feeling. Yes, we’ve done the obvious like him just pulling out and finishing on me, but I know he’d like me to swallow. I just can’t do it. Please help!

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—I Thought Drowning In Cum Would Be a Good Thing…

Dear Drowning,

I’m impressed by how thorough the two of you have been in taking action to rule out medical interventions and finding ways for him to ejaculate without overwhelming you with the volume of his semen. You say you know your partner would like you to swallow more often, and I’m wondering if you have more detail about that desire—what works for him about swallowing?

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If your partner’s enjoyment stems from ejaculating in a warm mouth, with little regard for what happens to the semen afterwards, you might consider if experiencing the peeing feeling is worth it every once in a while if you give up on swallowing and let it drool out of your mouth instead. If that idea is intolerable, proceed to the next paragraph.

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Is it knowing his sexual fluids are flowing down your throat? If that’s the case, focus on all the other stuff that both of you do find enjoyable. Sometimes our desires aren’t possible with a particular partner. Other times they aren’t feasible in reality at all. Your boundary is your boundary—you said it yourself, you “can’t stand this feeling.”

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It’s also worth having a conversation with your partner to make sure that your perception of his desires is accurate. It’d be a shame to spend all this time stressing, only to find out it isn’t that big of a deal to him.

Did you write this or another letter we answered? Tell us what happened at howtodoit@slate.com.

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Dear How to Do It,

I am a woman who got divorced two years ago from the only man I ever had sex with. About six months ago, I met “John” and we have developed a wonderful dating and sex life. However, I am encountering an unexpected problem. I have always been able to achieve orgasm through PIV sex, and it usually involved a “traditional” build-up and release—often multiple times. However, with John I find that many times I am orgasming very quickly and intensely. And when I am done, I have this sensation that I need to get him out of me as soon as possible. This is happening long before he is ready to cum, leading me to finish him with my hand or mouth.

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He isn’t bigger than my ex-husband, nor are we doing anything I haven’t done already. I just find that suddenly, I am the one that leaves my partner unsatisfied. For the record, he is completely understanding but somewhat baffled himself. What is going on here?

—Cumming Too Soon

Dear Cumming Too Soon,

Since you mention the intensity of your orgasms with John, I’m wondering if your climaxes are more intense than they were with previous partners. Sometimes harder orgasms lead to a more significant refractory period, which can absolutely manifest as tiredness, overstimulation, or general desire to stop the sex.

If you have enough foreknowledge of impending orgasm to slow or stop the stimulation—freeze in place, slow down, or completely break physical contact with your erogenous zones—you might be able to last longer by delaying the moment until he’s had his own climax.

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And if oral sex is something you’re both into, you might get him close with your mouth and then switch to penetration. Or alternate sessions involving as much penetration as you can handle and sessions with lots of oral stimulation for him. Good luck.

—Stoya

More Advice From Slate

I’m a 60-year-old woman who still attracts attention from others, which I desire. But I always say no, because of STDs. I do not trust men to answer me honestly about their status, and I know some men may not even know if they have an STD. My motto is better safe than sorry, so I stay at home, alone. I get by with sex toys, but I so wish for physical contact. So sad when the skin craves love. Is there any way out of this box?

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