How to Do It

I Have Sex With My Best Friend and His Wife. She’s Pregnant.

Does this mean I’ll never get to be “Uncle Danny”?

Collage of a man looking wistfully back at a pregnant couple in front of a neon circle.
Photo illustration by Slate. Photos by simonkr/iStock/Getty Images Plus and Ranta Images/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,

I am a 30-year-old, single man. My best friend since I was a young kid and his fiancée have been my two closest friends for the last decade. Many of their friends party harder than I do, which often involves the use of hard drugs (not my thing). For years, the two of them have talked about opening their relationship. I was never mentioned in the discussion and assumed if they ever did it, it would be with the party crows.

A little less than a year ago, after some drinks, the three of us had sex. They remain my best friends, but we now see each other several times a month and have a threesome about once a month. Despite my initial concerns, the relationship really hasn’t changed that much. The only noticeable difference is that I used to sleep on their couch more often. Now, unless they want to play around, I’m expected to take the subway back home when they’re about to call it a night (which I totally get and doesn’t bother me).

She’s now pregnant with their first child, about two months in. This past weekend, the three of us hooked up again for the first time since the pregnancy. We had a discussion about continuing this arrangement later into the pregnancy (probably, but she has to see how her body feels) and after the pregnancy (probably not, but who knows). Here’s my concern: Since the two of them got pregnant, I have noticed they are starting to write a lot of the harder-partying friends out of their lives. They discuss moving past that and have been noticeably limiting their friend circle. While they swear that they want me involved in their post-child life, I’m worried that much like their hard-partying friends, I may be written off at some point as a relic of their past due to these recent trysts. I don’t want to ruin a 25-year-old relationship and being called “Uncle Danny” over really, really fun threesomes. Do you think I should stop, or do you think my fears are unfounded?

—Three’s Company

Dear Three’s Company,

I think they already think what they think about you, no matter what you do. You’re not going to be judged on the incidents you have moving forward, but on the cumulative impression you’ve left. It seems like you’ve meant way more to their shared life than the “party crows” do, and even without your years of intense friendship, it would be reasonable to assume that as a sex partner you’re in a different class than drug partners. But who really knows? The implications of introducing sex into a previously platonic relationship are most usefully considered before the dick is wet, not after. You crossed a line when you hooked up with them, for better or worse—you’ll have to see which side fate comes down on.

People’s lives change when they have kids, both by design and necessity, so brace yourself for the distinct possibility that they might simply not have time for you for a while, even if you technically haven’t been banished from the harem. In the meantime, I think you’re fine continuing doing what you’re doing. You’re all adults, they want sex with you as you do them, and you’re able to communicate about your dynamic and future as friends. All this bodes well. That said, keep in mind that they’re in the relationship, it’s their kid, and you are a guest. Show up when requested, make yourself available otherwise, and hope that they see you as an asset, not a liability. Besides being the good friend that you have been, hoping is all you can do at this point.

Dear How to Do It,

I am a woman who has been seeing a guy for a couple months. Both of us are very interested in anal. He has more experience, but I have absolutely none and have no idea where to start. We’ve tried some touching but nothing more—where do we start? I’m also wondering about hygiene. He doesn’t smell the best below the belt. I don’t mind going down on him, but he usually wants me to go lower with fingers and my mouth. I honestly have difficulty getting past the smell. It truly seems like he doesn’t scrub that well in the shower, and it grosses me out to put my fingers down there. How do I broach this with him, and what do you recommend for my own personal hygiene before anal? I have smell/sound related hypersensitivity, so any mitigation tips for both of us are very helpful.

—Wary of Whiffs

Dear Wary of Whiffs,

If you’re going to be near someone’s ass, it’s reasonable to ask them to wash it. There is really no point in beating around the bush or, in this case, asshole, here. I believe it is one’s job to tell their partner about certain superficial, changeable things about themselves that they cannot detect (and that might seem rude coming from a less involved party): food in teeth, toilet paper on shoe, bad breath, butt stink. Unless this guy is under the illusion that he’s been cultivating a rose garden down there, it will hardly be breaking news that his ass smells like ass.

Fortunately for both of you, this is a problem that can be remedied with something as easy as a shower. Call me “old-fashioned,” but I think it’s rude for a guy to neglect to wash his ass before he gets head, even if the giver has no designs to eat his butt. Just having to be down there at all should be as pleasant an olfactory experience as possible. He probably could use a trim of the hair around his butthole, which is a veritable Venus feces trap. I know it might feel weird to ask him about this, but dried poop on your tongue will feel far weirder. As for you, wash your ass, too. Everyone reading this: Please wash your ass before sex. Wash it right now for practice.

As far as where to start, the general trajectory is fingers, tongue, and then … something bigger than fingers, like a dick or dildo. Pretty standard blueprint, saturated in lube. Let sensitivity and curiosity dictate your pace. Anal seems like a much bigger deal when you haven’t done it.

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Dear How to Do It,

I’m a 29-year-old gay man—I knew I was gay since probably 14 but came out officially at 21. Since coming out, I’ve dated one guy my age, but all the other more serious boyfriends have been older—ranging from three years to my newest interest who is a whole 10 years older. I guess I’ve always had a thing for older guys. They just seem to offer, in my experience, more security and calmness in a relationship, which is very important and sexy to me.

When it comes to sleeping with these boyfriends (and hookups), I usually bottom and can’t help but call them “daddy” when things really get going. I realized early on if I hold in that word, I get all up in my head and lose my erection, but once I can say it, the sex is so much more satisfying.

My last boyfriend was three years older, but didn’t seem to really like being called daddy. This was strange, I thought, since he was 6’1”, a tad bigger, and extremely hairy—literally a dad bod. We discussed it a couple times, and he always landed on the word being OK for me to say but he wasn’t necessarily into it. This led me to be self-conscious during sex, and thus our sex life was not great.

I guess this is a long-winded way to ask this question: With my new interest who is 10 years older and also has a pretty clear dad bod, is there a way to figure out if he’s OK with me using “daddy” during sex? It’s very important to me in terms of getting off, but what if he’s self-conscious about his age? His looks? Do I just yell it out in ecstasy the first time we do it and talk about it after? Or do I bring it up before? Do you have any advice on how I could share the importance of the word “daddy” during sex?

—Daddy, May I?

Dear Daddy, May I,

I think your best bet is to find partners who actually identify (on apps or what have you) as daddies. Then there will be no ambiguity in appropriate terms of endearment. Otherwise, I think doing it first and then talking about it after is the best way, as calling someone “daddy” in all likelihood will not be met with out-and-out offense but indifference or moderate disdain, at worst. Most daddy-type guys get it, whether they like it or not. Any daddy who balks at being called daddy is hardly the kind of daddy you want, anyway, so actually your ecstatic crying of “daddy” is not just what you need to get off but a good litmus test. Also, sex brain makes some stuff that sounds odd in theory actually work for some people, so bet on that. Call your daddy “daddy” and if he disagrees, you’ll know he isn’t. Simple.

Dear How to Do It,

My spouse and I recently found out that our 18-year-old daughter is selling sex tapes online. We’re obviously not happy, but she’s an adult now, and we feel like if we try to stop her it’ll just push her away even more. We’ve cut off all financial support. Her face is clearly visible in these videos and photos, and we’re worried this is going to affect her future (the videos were very easy to find). How do we talk to her about this?

—Camera Cringe

Dear Camera Cringe,

You have to understand that the world that you lived in as an 18-year-old is different than that in which your daughter lives. For some, doing porn remains taboo, but the democratization of communication has meant that so many more people have made publicly available pictures of themselves that once would have considered “compromising.” Tube sites, cam sites, OnlyFans … hell, quarantine Twitter has made the sharing of intimate material not only easier but more socially acceptable. Your daughter may have forfeited her chance to become president, but there was only the slimmest of chances of that happening anyway. Her laissez-faire attitude may pan out to be on the right side of history. I certainly think it is.

Besides, she knows the risks (including that her very parents might see the material she’s posting), and she did it anyway, so what can you say? No words will unpost her nudes. You can tell her you saw her pictures, but know that such a conversation may be awkward and could turn out to be the worst consequence of her sharing them. If you decide to tell her about your worries about her future, be compassionate and ask questions. Don’t accuse. Be prepared for her to shut down the conversation and be prepared in the long term for her to be right. And consider opening back up the financial support. She’s still your daughter and we’re staring down an economic depression as a society. Would you be OK with her starving? Didn’t think so.

— Rich

More How to Do It

Is anxiety making us come faster? I’ve been dating a wonderful woman for eight months. We’ve had a really enjoyable sex life. With the pandemic, we’ve basically been together nonstop since early March. What’s changed in the bedroom? The sex is even hotter, but strangely, we are climaxing within five to 10 minutes. Normally we spend about 45 minutes making love. We both are dealing with added anxiety due to COVID-19. Is that why we’re coming so fast? We’ve laughed together about how fast we’re coming, but it seems kinda weird to me. Is it my fragile male ego? Should we just keep having fast orgasms?