I Told My Husband the Spicy Surprise I Want to Get Him for His Birthday. He Was Skeptical—Then Realized I Was Serious.

How to Do It Photo illustration by Slate. Photo by Getty Images Plus. Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. (It’s anonymous!) Dear How to Do It, I’m a 37-year-old woman married to a 58-year-old man. We have been together for a decade, and it has been an incredible relationship and even better marriage. My husband and I met through industry functions and run two businesses together. We came into this relationship fairly evenly matched financially and without a power differential (I only mention this due to the age difference). We have two children together and one 18-year-old daughter from my previous relationship. The sex is great. Best I have ever had and we are very compatible (both pretty vanilla). There is no “but” to that. My question is that my husband recently made a comment that he has had sex with someone in their 20s in every decade of his life except his first one. I thought that a really fun 60th birthday present would be to hire a sex worker to keep that “every decade” streak alive in his seventh decade. I am a very “strictly monogamous” person myself. I am not interested in being with another man and I have no interest at all in a threesome. At first, I worried I would be repulsed by this idea in real life—not the idea of prostitution but the idea of consensual nonmonogamy—but I realized that this sounds more fun than anything else. I sat with the idea for a while and really imagined it, and I still think it sounds like a fun “gift” to give him, so I brought up the idea to see if he had any interest. He was suspect at first but pretty quickly realized I was being genuine. We agreed that the best way for me to dip my toe in would be to take a vacation and arrange this as an out-of-town experience. I feel like using a professional and being out of town leads this to be a fantastic one-time experience vs. something more regular, which I don’t believe either of us are interested in. He told me I am an amazing wife. Can you please share some tips and tricks to make the experience great as well as the aftermath of the experience? Things to consider, conversations to have, etc. —The Gift Dear Gift, I’m obligated to assume that you’ll be taking this vacation to Nevada, Amsterdam, Berlin, or some other place where direct provision of sexual services is legal. I think you’ve already done a great job at having conversations. You’ve talked through how to make this feel as safe and single instance as possible for you (though if it goes well, I wouldn’t be surprised if you decide to make it an every-decade arrangement). You might spend some time listening to your fears and writing them down as a way to see if there’s anything unaddressed that’s bothering you. You’ve got plenty of time to do this, and can go slowly. While your husband is with the escort he’s seeing, assuming you don’t plan to be present, have a friend who you can call if you need to talk or keep a journal nearby. Do something nice for yourself. Maybe that’s ordering your favorite dish, getting a massage, or your favorite exercise. You might also think about how you and your husband will process your feelings and reconnect after the encounter. Rely on reconnection practices that already work for the two of you as much as possible. Set aside time directly after to be alone together—in the hotel room you’ll be sharing is a great place. Maybe you have a big hug when he gets in. Maybe you take a bath together. Whatever works best. Think about whether you’d like the exact provider to be a surprise, and, if so, talk with your husband about his preferences and adhere to them. Contact providers in advance and tell them what your situation is. Some may prefer not to get involved, and others may be excited to fill this role. Start early, especially since it involves travel, so you have plenty of time to find the right sex worker. Good luck. —Jessica Stoya From: I Really Have to Tell My Boyfriend the Embarrassing Truth About Our Sex Life. (December 28th, 2021). Please keep questions short (<150 words), and don‘t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication. Dear How to Do It, I am a woman married to my best friend for over 20 years. We have similar interests in everything from politics to hobbies to movies. We have been through cancer, job loss, family deaths, raising three teenagers, and are now stronger in our 40s than ever before. We have regular, loving sex, and have never gone long without. Although we were young when we started dating, I had a varied sexual history and he didn’t (just a couple people). I also am attracted to women, although generally more to men. Sexual exploration was a part of my identity when we were younger, but then kids, my career, and just being a young couple trying to make ends meet took center stage. After I hit my early 40s, around the time my already pretty easy kids started to become more independent, I started to explore who I was again, and with that, my sex drive and interest in everything sex skyrocketed. Like tenfold. My husband is a great lover, but is rather vanilla. I’ve known that for years and have never been lacking in physical satisfaction. But my increased interest has prompted us to communicate more (we have taken some serious kink/fantasy quizzes, talked through certain things methods/techniques in detail), and that has made things more exciting. He was recently honest that he wasn’t really interested in some of my more kinkier fantasies and doesn’t like lots of dirty talk or sexting. He’s not into porn, is OK with some toys, and doesn’t care if I dress up. He has never really needed anything more than me naked (although he may be open to a threesome with another woman, but isn’t sure yet, which is fine—no rush!). Recently, we have rekindled some friendships with an online group, which was a saving grace for me as an extrovert and was something akin to a “date” for me and him during COVID. The group is comprised of married men, some are friends of ours for decades and some are newer. With my husband’s knowledge, I have initiated flirting/sexting with two of them. He is very cool with this because he likes to see me happy, I am not hiding anything, and it has made our sex hotter. He has been clear there is to be no physical contact, which is 100 percent fine with me. I dig fantasy, anticipation, and novelty. I’m loving it! One guy I’ve known forever has told me he and his wife have a similar arrangement (I know them both so I believe it) and that he “likes being married and never plans not to be.” Spousal boundaries are important to me. The other guy is the newest member of our group, and while the flirting has been more tentative and only via voice, has the potential to be more intense. Here’s the problem: My girlfriends, who are an important part of my life and are usually supportive and sex positive, are not only sure the sexting/flirting will lead to an affair that will ruin my marriage (??), but that if I must continue down this path of “self-destruction” I need to be sure this new guy’s wife that is OK with our discussions. They are also worried I am in love with him (sure I am high-school crushing on him, but I ONLY love my husband). I don’t know his wife at all, and so far, it has just been innuendo and flirting, so it feels mega awkward to say “in case this might turn into something hotter, I need your wife’s permission.” I finally feel like I have reached this great point of sexual self-actualization and my husband is super supportive, but my girlfriends are making me wonder if I am being naive. Can this work? Is this all too good to be true? —Wanting All the Good to Be True Dear True, You’ve found something that revitalizes your sexuality, and I think that’s wonderful. I’m glad you’ve had conversations with your husband about this and are proceeding with his blessing. There is absolutely a chance that he will be less comfortable with your sexting in the long run, so that’s something to keep communicating about. I think your girlfriends, supportive and sex positive as they usually are, may be less familiar with non-monogamy. We’ve got a deeply entrenched two-partner ideal, and configurations beyond that can be alarming at first. Dating, if you’ll remember a couple of decades back, is frequently awkward. And there’s no guarantee that our boundaries will be adhered to. Still, we continue to make connections, feel out possibilities, and navigate these issues. You’ll work out the most comfortable ways of describing your parameters. Maybe that’s “I want to flirt with you more explicitly. My husband is OK with that, and I need a similar permission from your wife to feel comfortable.” Or more of a direct, “How would your wife feel about a sexting relationship between us?” You’ll want to be prepared for a variety of reactions. They might be completely on board, to a degree that surpasses your desired level of involvement. They might be concerned or judgemental like your girlfriends currently are. They might not know what to say and need time to process what you’ve suggested. Listen closely and proceed. —J.S. From: I Told My Ex the Truth About Our Sex Life—and He’s Livid. (May 6th, 2021). Dear How to Do It, I’m a 34-year-old cis man, and the term hetero-flexible might apply to me. I don’t have any particular hang-up about men and their bodies, but am very rarely attracted to cis men.There have been times when I hooked up with guys, mostly in my wild 20s—with mixed results. Once (that I can remember) I’ve been romanced by a man who spoke my language. That led to fun and consensual one-nighter that included receiving anal. More frequently, however, encounters have felt a little gross. There were times someone got me drunk and had their way with me when I didn’t bother objecting. There were otherwise sweet dudes who got a kick out of leaving their fluids in places I didn’t want them. There were times I inadvertently led someone on and got chastised for it. There were times that clear and explicit “I’m not interested in anything romantic or sexual here” were ignored. There was some awkward gay-for-pay stuff when I was broke in San Francisco for a few months. I don’t harbor any resentments—we’ve all had good hookups and bad ones. However, the dominant theme was being objectified, which at this point in my life is a major turn-off. If I’m going to be someone’s drunk subby boy toy we better have a rock-solid foundation of respect first. (To be fair, I’ve also had some really great times partying it up at gay nightclubs and at LGBTQ-hosted events where I felt safe and welcome and included.) In the last 10 years, I’ve had fulfilling, monogamous, hetero relationships and dated women and haven’t given that stuff a second thought. Fast forward to today—I recently broke off a four-year partnership with my girlfriend and have been dating around again. In the last year of our relationship, we were getting more open about butt play (among other things). I had received but never given anal, and we worked up to that and we both had an amazing time. My endowment (generous) means that it took a decent amount of time and trust and work together to get it right—and it’s not something I want to get wrong and leave someone averse in the future. It would be cool to learn more about both the giving and receiving and how that can be fun for both parties. I’ve also recently become really interested in dicks and balls. I want to handle some. I’m turned on by the idea of giving pleasure and also the (imagined) sensual joy of interacting with them. I’m curious about that experience. I might even consider putting my mouth on some, if it felt right. Regarding anal sex, I don’t want to rush into it, and certainly don’t want there to be any expectation I’ll take it. I already know how to get fucked. I’m just craving some hands-on time and an idea of what is out there. I’ve seen probably 50 or 100 vulvas in my life, all different and unique. How come I only get to see my own junk? I am pretty well-endowed myself, fit, and have been appraised as an attractive partner. Definitely not a charity case. I understand that frequently, dicks and balls are attached to male presenting bodies, which is … fine. It’s not the masc vibe that turns me on particularly. I just want to get up close with some low hanging fruit in a way that is open-minded, fun, and safe and doesn’t involve sleezy bars or playing out some stud’s fantasy about converting/railing a straight boy. I’d like to give some attention and receive some feedback. This is a sensitive area (no pun intended). Communication, empathy, and respect are basic criteria for all my connections, particularly here. I live in a midsize college town that is progressive but has a pretty limited dating scene. 50/50 chance any given barista or work colleague has seen what’s on my Tinder profile. I know a few folks in poly lifestyles, but I’m not sure I’m comfortable texting them and asking if I can borrow some dick—especially in this smallish town. How do I proceed here? It seems like maybe what I’m looking for is another hetero-flexible or bi guy with whom I can have a good conversation, and also wants to experiment. Too bad I find about one-in-a-million attractive. Or maybe I’m looking for an individual with male parts and some experience who is willing to meet me where I’m at and would tolerate (enjoy?) me bumbling around their nooks and crannies for an hour with no guaranteed outcome. I’ve entertained the idea of hiring a sex worker but I’d prefer to start with options that don’t require a lot of travel or expense. Any pointers? —Is There an App for This? Dear I.T.A.T., I’m having a hard time pinning down what it is exactly that you want, and given all the words about yourself that you have shared, I suspect you are as well. Just how important is attraction to you? Do you need a nice face to go with the dick, or can you just focus on the dick? Another way to look at this: Can you really say that someone with whom you have a connection based on “communication, empathy, and respect” is someone you aren’t attracted to? Intellectually or emotionally, at least, that level of chemistry would qualify as attraction by many standards. There are several different types of attraction, and just because you seek certain qualities in men that you might not in women (and vice versa) doesn’t mean that you aren’t attracted to them, per se. I suspect that in order to preserve your masculinity/hetero status, you are taking pains to distance yourself from certain hallmarks of queerness. However, I’m not saying that you should immediately reframe your desires or work actively to understand them differently; you may find that your somewhat rigid criteria of what this all means may dissipate with the comfort that comes from experience. Keep in mind, too, there are many ways to objectify, and I don’t believe that all of them are necessarily toxic. You were taken advantage of because, indeed, partners did not recognize or respect your humanity. However, hooking up with someone for his dick is its own form of objectification. Luckily, you will find guys who are into being objectified for their dicks, and that kind of consent can foster connection, even if it’s ultimately fleeting and superficial. I think you can spell all of this out on an app that allows for detailed profiles, like Scruff, or even via the Craigslist personals replacement Doublelist. What you are looking for is highly specific, and you carefully map it out. It is completely reasonable to seek connected, casual sex. Will you find other “hetero-flexible” guys who are looking for that as well? It might be tough. Masculinity’s grip on queer culture (and beyond) means that you’ll have to get in line behind everyone else who’s looking for a straight-ish guy who’s happy to sit back and be serviced. Will labeling yourself as “hetero-flexible” or even bi prove to be an asset in online cruising? It may, but of course, it opens you up to being objectified for it yourself. It seems most people are looking for some highly specific configuration of parts in these no-strings contexts. It’s the nature of the game. If you’re attracted to dicks, but not the people attached to them, a gloryhole might be right for you. The caveat is the person on the other side of the wall is almost certainly expecting you to put your mouth on it and minimal discussion will take place. But I think that what you’ll soon find is that you can’t have everything, and so you should be open to something that scratches the general area of your itch rather than gets at it entirely. Few things ever will, and those are the real keepers. —Rich Juzwiak From: I Told My Ex the Truth About Our Sex Life—and He’s Livid. (May 6th, 2021). More Sex Advice From Slate My wife and I have good sex—great sex, even—about three times a week. But for most of our relationship, I was the only one to initiate, and then she would enthusiastically say yes. It’s rare that she starts anything. When I asked her to initiate more, I had no idea it would turn out the way it did. Never miss new Slate Advice columns Get the latest from Prudie and our columnists in your inbox each weekday, plus special bonus letters on Saturdays. Advice Dating and Relationships Sex