How to Do It

Neither My Wife Nor My Boyfriend Is Brave Enough to Give Me What I Want in Bed

I wish they’d just go for it.

Woman looking over her shoulder. A peach floats next to her.
Photo illustration/animation by Slate. Photos by Getty Images Plus.

This column is part of Advice Week, Slate’s celebration of all things advice.

Sometimes, all you need is a different perspective. So this week, our columnists have swapped fields of expertise. In this edition, Lillian Karabaic, a Pay Dirt columnist, handles your sex questions.

Dear How to Do It,

I (40F) am married (42F) and we are in an open poly triad with our boyfriend (48M). We all date (and have sex) together and separately. We are also free to have additional relationships, as well. We work hard at communication (and therapy). We have lots of fun and great sex.

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Here’s my question: I really like butt stuff, but I’m not sure how to make it happen. Here’s more context: I’ve done some anal play with previous partners. There has rarely been a lot of conversation about it. It’s always been a thing they just kind of went for and I am really into it. Except for my experience with penis-in-ass sex, which was great and involved really explicit consent.

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Both of my partners are interested in doing things to my ass…but neither of them does. I don’t know how to bridge the gap. The thought of saying, “This is hot, you can stick your finger in my ass if you want to” is terrifying because of a fear of rejection/ruining the moment/things being weird. Is that the only way? Get some gumption or go without?

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Bonus question: Boyfriend has definitely expressed a desire to bottom for some anal play. My initial reaction is averse, but I tend to pride myself on being willing to try nearly anything (and honestly, it feels more like fear of the unknown/lack of confidence than actual aversion). And if I try it, I might love it! (Or I might not hate it and he might love it, which is also a big win). Any pointers on a mental reframe? And how to bridge the gap there?

—Aspiring Anal Aficionado

Dear Aspiring Anal Aficionado,

You’re going to have to woman up and ask for what you want. Hinting will only get you so far. Generally, anal play isn’t exactly a spur-of-the-moment occurrence the first time, and that’s OK—there are some prep and supplies that go into a good butt experience. The logistics aren’t always sexy, but the experiences can be.

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If you don’t want to kill the mood during the deed, try bringing up your interest during a non-sexy time so that it’s less surprising when you mention it in the heat of the moment. I’m not suggesting you say, “I’ve had a great experience with anal play in the past, and I’d love to explore it more with you,” over a linguine dinner with your aunt. But there’s already communication that goes into a successful triad, so mention it during a non-sexual but intimate time, like a Netflix cuddle puddle. You could also consider proposing that each of you write down a list of sexual experiences you’d like to try. This might open your eyes to what your partners are interested in but also afraid of voicing in the moment.

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As for pegging—try it at least once if it’s on your boyfriend’s list. As long as you both prepare appropriately, you might be into it. If you don’t try it, you’ll never know if you like it.

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

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Dear How to Do It,

So, I recently got HSV-1 from someone, orally, and it’s made me really hesitant to date/kiss/etc. again. I know it’s super common and most people I’ve talked to say they’ve never had a problem passing it to someone when they don’t have a cold sore, but I’ve read that it can also shed asymptomatically. This made me think that I could never kiss/perform oral on a future partner again because that risk could still slightly be there. And I feel like the first encounter, knowing I have this, I’ll be super anxious and not be able to enjoy myself because I’ll keep thinking about it. I know it’s highly stigmatized, but is it really not that big of a deal?

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—Anxious Lover

Dear How to Do It,

I’m sorry you had that experience. But it’s important to know that you’re in the majority, not the minority. Herpes infections are common.

The most important thing you can do is disclose your status to potential partners, and use barriers during oral sex. If you have an outbreak, then a break from kissing until your outbreak goes away is a good way to protect your partners. The stigma surrounding STIs causes more harm than the infection does itself. If people are afraid to talk about their status because they risk their partner freaking out, they’re more likely to not take precautions. But you have to take appropriate measures to protect your partners when you know you’re symptomatic.

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Our current pandemic has highlighted that we should be taking precautions to protect others from all infectious diseases, STIs or not. Catching COVID-19 is not shameful, but knowingly going out while infected and coughing all over a stranger without telling them you’re positive should be. Herpes is the same—you can’t 100 percent protect people from it, but you can avoid contact when you have an outbreak and be upfront about your status. That’s all you can do. Don’t stress yourself too much about it.

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Dear How to Do It,

I’m a 31-year-old woman and I’ve never had sex, which causes me an intense feeling of shame. I think I missed that time period in college and high school when everyone was fooling around and there was a distinct lack of judgment that I feel as an adult. The thing is, it’s not like I’m abhorrently ugly or off-putting in some way; rather, I always wanted it to be with someone I trusted and/or loved and that relationship has never happened. So now, at 31, I’m looking to move past the “someone I love/trust” requirement and just get it over with a nice stranger. My question is, what is the best way to do this, especially at my age? I’ve tried dating apps but everyone who’s on there solely for hooking up acts aggressive at worst, and slightly creepy at best. I’m struggling to figure out a safe and comfortable way to make this happen and to finally open that sexual chapter of my life, which I would really like to do.

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—Feeling Frustrated

Dear Feeling Frustrated,

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While writing this response, I searched YouTube for compilations of Emma from Glee talking about her experience of losing her virginity in her 30s. Even though she’s a fictional character, she illustrates that there are all sorts of different ages and reasons for someone’s first sexual experience. I hope you can discard your intense shame about sexual inexperience—everyone is on different paths, and there’s nothing wrong with being a late bloomer. But please don’t try to conceal your inexperience from potential partners out of fear. If a potential partner reacts badly to your inexperience, they have eliminated themselves from the pool of candidates and revealed themselves as a bad match.

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Since you’ve already waited until you’re 31 to have your first sexual experience, you can afford to take a bit longer to find the right person. Because you only need one to cross it off the list. If you are honest with the people you pursue about your situation, you’re more likely to find the right fit that is willing to consider your needs.

The apps can be overwhelming, no matter your experience level. You might try an app like Bumble, where the woman messages first to avoid some of the hookup-hungry message deluges. Also, consider social groups for singles focused on something other than bar or hookup culture, like walking or book clubs.

Consider if you have a friend, who’s expressed interest, that you trust but aren’t likely to get emotionally attached to after the deed. A friend can be an excellent way to rip off the sexual bandaid without having to assess the safety of a whole new person. And don’t give up if the first experience is lackluster. It probably won’t be bodice-ripper amazing because sex, like anything else, takes some practice. But you should be able to ensure your first time feels safe if you choose the right person.

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Dear How to Do It,

I’ve always been curious about casual sex, but I’ve never had the mental/emotional/physical resources together to feel secure about experimenting outside of more committed relationships. I finally have a really good therapist, I have a rock-solid open marriage, and I currently don’t have any other partners than my wife so I have a lot of free energy for casual encounters. My wife is very supportive of me exploring and figuring out what I like!

Do you have any advice for someone who’s newly dipping their toes into the hookup world? For context, I’m a queer, 33-year-old, femme-ish person who’s mostly but not exclusively attracted to women. I’m autistic and chronically ill, and I worry a bit that my imperfect grasp of non-literal conversation and my physical limits due to pain/unexpected flare-ups will cause stumbling blocks. I plan to get a full sexual health checkup before I sign up for apps. But I also just have very little idea what to expect, as I don’t know anyone personally who’s seriously gone for lots of hookups. So I don’t have any models for how it works in my own life. On the bright side, we do live in a bigger city now that’s a bluer spot in our otherwise red state, and my best friend does have at least one club she’s willing to take me to when I’m ready. Do you have any encouragement or tips for me to keep in mind before I take the plunge?

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—Let’s Get Wild

Dear Let’s Get Wild,

If you haven’t already, establish boundaries (I recommend The Ethical Slut) about what is and isn’t OK with your wife. Some things to consider: Are you allowed to repeat the same partners? Does all casual sex have to happen at the other person’s place? Can you spend the night, or do you always have to come home? Does your wife want to know all the details of your conquest or never hear about them? Can you hook up with a mutual acquaintance or friend, or do they have to be strangers?

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You’ve thought of the critical things: testing, pursuing your first swingers club with a safe person, and security in your primary relationship. When seeking casual sex, being upfront about your relationship status with folks from the beginning is important. Better to be forewarned than forlorn. Mismatched expectations are the enemy of a good time. Be clear and forthright with anyone you meet on an app or in person: “I’m only looking for casual sex outside my open marriage.” or “Just so you know, I have a wife who is OK with me having sex as long as it’s casual.” This will save you from heartaches. If someone isn’t interested in your terms, move on to the next person. And good luck: Go forth and screw!

—Lillian

More Advice From Slate

I’m a man in my 20s. I’m currently dating a great girl, and I’m confident in my sexuality. However, ever since I was a preteen, I’ve had a fetish that seems to only be getting stronger. I get really turned on by being naked in locker rooms.

Correction, Jan. 23, 2023: This piece originally conflated HSV and HPV. These are two different viruses.

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