How to Do It

I Can’t Get Over What I Learned About My Fiancé’s Real Sexual History

A man and woman in their 15s with a tally between them.
Photo illustration by Slate. Photo 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 am a divorced woman in my 50s happily engaged to a man my own age. We love each other, find each other hot, and have great sex together. I feel incredibly lucky! Here’s a thing, though. After his divorce, he was single for about a decade, and used the time to do what the rest of us did in our 20s—and more. He had young girlfriends; experimented with threesomes; and sometimes paid for sex with several hot sex workers whom he saw regularly. It was revelatory and liberating and fun for him, although in the end, he was ready to settle down.

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I love sex. After my divorce, I was cheered up by having several much younger boyfriends who were into me. But what I experienced was nothing like what my fiancé experienced—he fooled around with his transgressive, exploratory side much more than I did. At heart I’m pretty conventional about what I want.

Here are my questions: One, won’t he get bored with just me? Two, how do I deal with the fact that he did things when he was sleeping around—anal sex, for instance—that he feels weird doing with someone he loves? And three, I find myself fantasizing about him and the hot sex workers. He and I have discussed having a threesome, but the idea of hiring a woman to sleep with both of us feels exploitative. And realistically, it would be more fun to have a young partner—and so how do older women deal with the jealousy and insecurity that might bring up, seeing their partner turned on by a fit young person? Once you have a threesome, does regular sex become dull?

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—Just Asking

Dear Just Asking,

These two sentences—“At heart I’m pretty conventional about what I want,” and “I find myself fantasizing about him and the hot sex workers”—together bring up a couple of questions for me. Presuming your definition of conventional is the, well, conventional one, threesomes and sexual commerce would seem to be at odds with it. What’s going on there?

Are you conservative in practice but exploratory in your fantasies? That’s totally a thing. Sometimes specifics are wonderful to fantasize about, but we don’t want to actually experience them for one reason or another. You and your fiancé could have a robust fantasy life where you describe various scenarios to each other or even role-play them.

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Are you less conservative than you think of yourself as? That’s totally OK too! Not only does sexuality change as we mature and encounter different experiences, hormonal shifts as we age can affect our sexual response. Sometimes it takes a little longer for our self-image to catch up with our new reality. Give yourself time to experience your fantasies and get an idea of which, if any, you’d like to pursue.

Sure, he might get bored with you. You might get bored with him. Uncertainty is a part of romantic relationships. Be yourself, show up and be present, and see how the relationship plays out. Jealousy and insecurity are a part of romantic relationships, too, especially when they’re nonmonogamous. Are you happy with who you are as a person and what you bring to the relationship? If so, focus your thoughts on those positive aspects. If not, well, you now know where to do some work.

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Lastly, I’m a bit concerned by the part where you say “he feels weird doing [certain sexual activities] with someone he loves.” This has a whiff of Madonna/whore complex to it, and is something to keep an eye on. You might initiate a conversation about this, by asking if he understands why or has any insight to offer you.

Dear How to Do It,

I am a woman in my 60s and have never had any trouble orgasming via PIV or external manual stimulation. I’ve been separated from my partner since the pandemic began, and I have had to rely on masturbation for the last 10-plus months. So I decided to give vibrators a try. After researching “quiet” vibrator recommendations, I recently ordered five different vibrators (including one that supposedly mimics oral sex). Only one of the five was actually quiet, and most of its settings were still faster and more intense than what I like—in fact, it made my lady bits go numb. Why can’t I find a vibrator that is less “intense” and more like what one would experience with a human hand? Different strokes for different folks, right? Maybe the vibrator companies will take notice of a request made in your column. Til then, I’ll go back to my own hand!

—Not Vibing

Dear Vibing,

I met a woman who worked for Dame Products one year at a Women of Sex Tech event, and wondered if she might have some insight into why gentler speeds are hard to find. CEO and co-founder Alexandra Fine told me, “For many sex toy companies, the goal is to make their products’ vibrations strong and powerful enough to stimulate the desired sexual response. However, by listening to our customers, we know that pleasure comes in many different forms for many different people.” A PR rep there recommended their Pom and Zee vibes. The Zee has a fairly low setting, while I think the Pom will still be too intense. Others I asked recommended Unbound’s Squish or the Minna Limon Squeezable Couples Massager, a pair of similar toys that respond to being squeezed. The Limon is very responsive to pressure, and with a light enough touch is barely a rumble. I can also vouch for Lelo’s oral sex simulator, the Ora 3, being more of a tease toy. (I should disclose I’ve done an extensive amount of influencer work for them.) The settings with vibration are still pretty strong, so you’d be limited to two patterns where the nubbin moves around mimicking a tongue without vibrating.

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From my research and based on your specific needs, I think the Minna Limon is your best bet. Good luck.

Dear How to Do It,

I’m a queer woman with a nonbinary partner, and we have a deeply loving, engaged relationship. Generally all is well. Onto our one problem: My partner usually has a fairly masculine, though bordering on androgynous, presentation. We’ve known each other for a long time, and I’m used to that presentation. In the past few years, however, they have days where they adopt a very, very femme presentation: Their voice is distinctly and deliberately higher, they dress in a very feminine style, use floral fragrances, and even seem to have somewhat different interests. It’s a dramatic change. On these days, we hang out and do our usual routines, but I feel so differently toward them. I am wildly attracted to the “usual” way they look, behave, sound, and even smell, and it’s like all my cues are missing when they are presenting in this super-femme way.

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I have had relationships with various people who identified as male, female, trans, gender-fluid, etc., and I am attracted to a range of gender expressions, but I’ve never really been attracted to anyone very femme before—my attraction skews toward androgynous people, never toward very conventionally masculine or feminine people. On days where my partner is so femme, I find myself behaving differently toward them, still with respect and care, but like I would behave with someone who is attracted to me but to whom I don’t want to give the wrong signals— just very platonically. I don’t know what to do, or how to talk with them about this in a way that is loving and supportive of their gender expression, but also conveys how differently I feel about them when they seem almost like a different person. I wish I could make my attraction to them consistent no matter their presentation, but I just haven’t found a way to do so. I would love to hear your perspective on how I can respectfully communicate these feelings to them, or change my approach to these femme days, or to figure out a way to reconcile my usual intense attraction with the sexual disinterest I feel toward their very femme presentation. They say they feel most sexually awake when they’re presenting in this mode, and unfortunately that’s when I feel least sexually connected to them.

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I am also not sure what to think about their new (or newly shared) interest in pursuing therapies that minimize masculine body hair (such as finasteride) or will possibly alleviate some dysphoria (such as a low dose of estradiol). My previous partner was trans, female to male, and transitioned while we were together. It was … not a great experience for me, and we parted ways after he transformed so completely into someone I didn’t recognize anymore (intensely masculine, not my thing). I understand that transformation is fairly the point with hormonal therapy, but from that experience, I have lingering concerns about again being with someone going through that type of change. Any help you could give in navigating this would be much appreciated.

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—Attraction Whiplash

Dear Attraction Whiplash,

Your desire to be empathetic and caring toward your partner is palpable. To support them, you need to take care of yourself, too.

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Based on a prior relationship, you’re concerned that as your partner continues their apparent experimentation, you won’t want to be with them in the same way. That’s valid. It might happen. You’re dealing with some uncertainty because you aren’t sure whether their femme expression is going to become the default, and they may not know themselves—or be ready to share that inclination with you.

Communication is the way forward. You’ve known each other for at least a few years, so you’ll have knowledge of where they’re likely to be sensitive, and how to best broach things. Think back on issues you’ve tackled together successfully for ideas on how to proceed. Be prepared to have these talks in stages, so you have time to process your emotion and space to think from various angles, and they do as well. Pick a time when you’re both calm and relatively unstressed, have eaten, had enough sleep, and have plenty of time to talk.

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Start with your feelings. Establish that you love them. Tell them your sexual attraction is usually oriented toward certain presentations and not toward others, as clearly neutrally as possible. It might help to think through your phrasing beforehand. Give them time to absorb what you’ve said. You might bumble and need to provide reassurance or apology. Go slow and pay attention to body language and facial expressions. If your partner seems like they’ll be receptive, try to talk about their presentation, and how they are feeling about it. From there, hopefully the conversation can proceed to how this can work in your relationship, or not. I think you’ve got this.

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Dear How to Do It,

I’m a woman and my boyfriend wants to have anal sex. I searched online how best to get that area clean as a whistle with no viable results. Can you provide some different options? And how long the treatments take? I do not wish to have the trots from magnesium citrate. Thank you!

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—Hesitant on the Hershey Highway

Dear Hershey Highway,

Your rectum has a purpose. There’s no way around it. Sure, it’s cool that fingers, penises, and dildos in your anus can make you feel good, but its main job is poop. You cannot fully sanitize your asshole. Anything strong enough to do so would be harmful to your delicate mucous membranes. I’m hoping nobody needs to hear this, but just in case—under no circumstances should you ever put anything like Lysol in your butthole.

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You are correct that magnesium citrate makes bowels move. So do the sodium phosphates in Fleet enemas. My co-columnist Rich Juzwiak has shared his own routine a number of times in these pages. The short of it is psyllium husk taken orally, which makes stool firmer. Time your anal sessions for after a solid poop and a shower, and keep a couple of paper towels on hand just in case.

—Stoya

More How to Do It

I’ve been dating a guy for nine months and totally fell for him. Through a conversation, I found out his “ideal” life is to have a main and two side women. What he previously “forgot” to mention is that he’s already doing this and has been having sex with others—but I’m the “main” and he just wants variety in his sex life. Should I be proud I’m the main or hurt that he isn’t happy with just me?

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