How to Do It

A Decadeslong Sexual Secret Has Me Questioning Who I Really Am

Is it time to fess up?

Man looking at a name "Jerry" glowing in neon.
Photo illustration by Slate. Photo by 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 gay male aged 52. As I age, I look back and wonder, “Did I live my life well—or not?” Overall, I feel very good and blessed about my life, but there is one thing that makes me question myself. When I was 21, I was fortunate to meet Rick.” He was 33 and well-established. We became fast friends and soon after that, we became lovers. I felt like I had hit the jackpot. After 10 months, I moved in with him. The relationship was easy, and we never fought. When I was 32, I noticed our sex life was really slowing down, and not because I wanted it to. It seemed Rick was just losing interest in it. My pleas for him to go to a doctor to see what was going on were ignored. By the time I was 33 and he was 45, we only had a platonic relationship. But still, I really liked him. So I was going nowhere.

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Until two years later, when sitting in a dental office waiting room, I looked up from my magazine to see Jerry giving me a broad smile from across the room. Wow! Instant attraction! One of the most handsome men I had ever seen, with a build to match. But he was wearing a wedding ring. After our appointments, we ended up talking in the parking lot for about 20 minutes. He was married and had a 5-year-old and a 6-year-old. Always knew he was bisexual, but never met anyone that made him want to act on it. Until that day. His wife traveled on business a lot. He was a writer and worked from home. His home was only half a mile from my office. Soon we were having nooners while the kids were in school. The sex was mind-blowing! I never told Rick, but Rick was happy that I was no longer pressuring him for sex. And so we were both happy.

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Very unexpectedly, Rick had a heart attack and died at 50. I continued the relationship with Jerry. No one in his life has ever known about me, and no one in my life has ever known about him. And we don’t know any of the same people. About a year later when I was 39, I met Robert. To make a long story shorter, we had a great relationship for six years, until his dad died, and he had to return to his hometown to take over the family business. Jerry knew all about Robert but never the other way around. I wasn’t about to move with Robert (it was a very rural area), and I didn’t want to leave Jerry. Four years ago, I met Jim, who knows nothing about Jerry. When partnered, I have always put Jerry in second place. Any plans with my partner always took precedence, and that meant that sometimes Jerry and I didn’t see each other for five or six weeks. But sometimes it was three times a week! I treated all my partners very well. And Rick, Robert, and Jim always expressed appreciation for my efforts. But … there is Jerry, a man I would have married if he had been available. He tells me often that he cannot imagine his life without me. I feel like I have made the lives of four men better. But, am I a good person? Or a bad person? Should I fess up after all these years?

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— Hanging in the Balance

Dear Hanging in the Balance,

Rick and Robert and Jim and Jerry. Is this an advice column or the premise for an early ‘90s Broadway play that would have, during its relatively short run, accrued a fanatic cult who remembers it fondly to this day?

I don’t know if you’re a good person or a bad person, but you seem to be sensitive and have a decent grasp on your situation. You’ve kept Jerry as a side-piece for nearly 20 years now, so at least he thinks you’re cool. He’s a better authority on your goodness than I am. Certain lapses in communication haven’t been ideal, and a truly ethical approach would have involved giving your partners a heads-up about Jerry. I know that’s daunting, but you’re dealing with queer men, who tend to not live by strict heteronormative standards and are more likely to get it when other people are nonmonogamous.

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I don’t think keeping Jerry in “second place” is an issue—he has his own life. You discuss what could have been, but the relationship only is what it is: A sexual pairing with strong chemistry that you visit when convenient for the two of you. I’m not exactly clear on your feelings beyond that—I know they exist, because you say you would have married him, but I can’t tell if you’re in love, or dickmatized, or swinging between those two poles. (You do, after all, like to swing between poles.) Having a buddy that you can have reliably great sex with is a wonderful thing. There’s nothing wrong with that. Deception can taint a situation that is otherwise pure in its beauty and pleasure, but I don’t know, it seems like you’ve done your best, and if you feel that you’ve made the lives of the men you have loved better, you probably have. (You would know if you didn’t.)

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You should figure out if there are reasons you’ve kept Jerry from your partners beyond assumptions of them not understanding as a result of societal programming. What’s stopping you from talking about it with Jim? If you think he’d actually shut down the relationship as a result of your disclosure and you’re deceiving him anyway for your own selfish purposes that’s … not great. But you can change it. You’re defined by your behavior, not what I have to say about it. Nothing that I can write will absolve you. That’s on you.

Dear How to Do It,

I have a buried penis and have all my life. I didn’t even know it was abnormal until I was a teenager, but once I did realize it, my self-esteem was shot. I was embarrassed being naked regardless because I was a teenager, but I didn’t want anyone to ever see that I had an “innie.” I didn’t date in junior high or high school because I was terrified of sex and that someone might notice and see me as a freak. In college, I avoided hook-up culture as I wanted to have sex in a committed relationship where someone might get to know me and maybe care less about my penis, but I did end up having a brief fling.

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The first time we were intimate and doing some foreplay, she asked me where my penis was. We were cramped in a twin bed and, even when erect, my penis was almost entirely hidden. I discovered later that if I was on my back I’d have a better (albeit small) showing but not on my side as we were at the time. She was sweet about it, saying that it was okay if I was trans or intersex. This was quite progressive and made the experience less mortifying when I said I wasn’t, but being asked where your penis is from the woman you are about to lose your virginity to is brutal. At the time I thought that this was going to be a prolonged relationship and that we’d figure it out together but alas she shut it down after two nights, and I don’t blame her.

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A few years later, after avoiding sex and intimacy, I was in my first and only committed relationship and had penetrative sex for the first time. I hated it. She hated it. Eventually, we made it sorta work but it was always awful and stressful and if I shifted the condom would fall off. She’d never slept with another person but I’m sure she knew that most men aren’t like me and can physically have sex in more than one position as it only kinda worked if she was on top.

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When we broke up after a few months for various reasons, I decided to give up having sex again, and I’ve been single and celibate for 12 years with little or no hope of changing that. I didn’t care all that much for most of that time, but I’m in my mid-30s now and I’m at a place where I’m either looking for a life partner or resigning to being alone forever. I want to be able to provide a satisfactory sex life to a potential partner, but I fear that I may never be able to.

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I don’t really care about my own experience because I don’t get much pleasure from my own orgasms, but I would like to please someone else and I don’t want to disappoint someone if they want or need penetrative sex. I also don’t know how to prepare for a date or something. Do I need to have a toy on hand or attempt terrible oral having never tried? I’m just kind of lost and I feel like avoiding sex for most of my young adulthood on top of having this problem has really hindered my ability to start again now. Also, the thought of going through the rather barbaric and likely way too expensive surgery to repair my penis is enough to make me want to go the way of being alone forever. Any tips?

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— Buried Alive

Dear Buried Alive,

You’re writing from a limbo that you remain in as a result of inactivity. It’s clear that you’ve neither accepted your buried penis, nor are you willing to take the steps to do something about it. I highly recommend reconsidering the surgery. While the sample size is small, this study of people with adult-acquired buried penis found clinical depression in seven out of eleven participants pre-op, but that number shrank to two after reconstructive surgery. Your letter reminded me of a comment made by Dr. Charles Welliver, director of men’s health at Albany Medical College, whom I regularly hit up for questions about urological issues. Responding to my query regarding Peyronie’s, Welliver wrote me that “super high rates of depression” have been observed in people with Peyronie’s, which can cause sharp curvature of the penis and make intercourse difficult. “Shows how much of guys’ self-image is below the belt,” Welliver concluded. That’s spot on, and I think it describes your situation well.

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I understand why you are frustrated and your inaction does make an unfortunate kind of sense. But even if you are set on forgoing surgical intervention, you must do something or you’ll remain this way. Your letter is dripping with negativity. You assume, for example, that your attempt at oral will be “terrible” since you’ve never tried it. With that attitude, it probably will be! Certainly, you can research. My HTDI partner Jessica Stoya recommends Jessica Drake’s Guides to Wicked Sex, which includes a Satisfy Her entry (that link is NSFW). But the best research will come directly from your partner. No media source beats open communication.

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But that would require, of course, having someone to communicate with. That’s not just going to happen magically. Point yourself in the right direction by putting in the work to process what it means to have a body that defies outside expectations. A therapist might be useful.
Community is another option—something like the subreddit /smalldickproblems may at least remind you that you’re not the only one going through this and give you tips for managing via people who have lived similar experiences.

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The other major issue here is your sexual response, which includes hating the penetrative sex you have had and not getting pleasure from your own orgasms. I think it’d be practically impossible to unravel these feelings about sex from your relationship to your body, but there are people who have similar aversions to the act and identify somewhere in the asexual spectrum. Have you considered that such an identity might apply to you? For some, a lack of interest in sex isn’t a problem to overcome—it’s just their reality. You want to want sex, but do you actually want sex? Is your desire to please someone else a function of lust or a sense of obligation to act as you think you should? Societal imperatives and striving for “normalcy” can cloud our senses of self.

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Taking sex off the table entirely, at least for a time, might help you achieve what I see as a greater goal: Connecting with people. Try relieving pressure by deciding that you’re going to meet people and talk to them (on, say, dates) with no set expectations of things turning sexual. It could be that a lot of the anxiety you have about sex dissipates when you find someone you actually want to have it with—an actual human out there, instead of the big scary idea that’s haunting you from within. If those feelings of sexual attraction should never surface in these interactions, that’s OK, too.

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Dear Scared,

Im a 30-year-old pan guy. My first serious girlfriend Alison” in college was also my first experience with sex, and its left me with some baggage I dont know how to unpack. I didnt know it when we started dating, but Alison had a serious eating disorder and was very sick.

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I have a kind of above-average sized dick, and Alison was very, very skinny, so I could sometimes see it moving inside her during sex, which I thought was super-hot, and is still something I fantasize about, and cum immediately if I see it in porn. Then I immediately feel sick and guilty, because Alisons illness was terrible.

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Ive been exclusively dating and hooking up with men for years because I find myself freaking out about health and whether theyre eating whenever Ive tried to date women. Im not even sure if its possible for me to have the type of sex that turns me on with a healthy woman. I have a crush on an acquaintance right now that I know is reciprocated, but Im terrified that either shes going to turn out to have an eating disorder or Im going to drive her away focusing on whether shes underweight. How do I untangle this?

— Scared

Dear Scared,

I think the first thing to be cognizant of is that you aren’t necessarily eroticizing Alison’s eating disorder. You had hot sex and something that occurred as a result during it turned you on. The eating disorder may have been what made the image you fetishize possible, and certainly no sex act exists outside of the context of the life that it’s a part of, but I think you can go easier on yourself. Sometimes the images we see during sex leave a lasting impression because the sex was good (or, perhaps in this case, because it was a new, tangible illustration of your endowment)—titillation by association.

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Given the magnitude of your unwanted thoughts, I wonder if you have ever been diagnosed with OCD. It might be worth looking into, especially if you have recurring and unshakable unwanted thoughts about things having nothing to do with sex. It’s irrational for you to assume that your crush has an eating disorder. You won’t drive her away by focusing on her weight unless you actively do so. You theoretically have the ability to control that, and if you feel like you don’t, it’s time to talk to someone who can help.

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Dear How to Do It,

I’m really struggling with letting go of a long-term crush and need some advice on how to shut it down. Basically, I’ve had what I thought were unrequited feelings for my best friend for seven years. From the moment I met him, I wanted to be more than friends, but life circumstances kept getting in the way. I resigned myself to being grateful to have someone like him as a best friend and privately dealing with the pain of his romantic obliviousness to me for the rest of my life. The feelings haven’t stopped me from having other meaningful romantic relationships, but they were always there in the background as something I hoped I’d either grow out of or would finally come to some kind of resolution.

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Well, the resolution seems like it’s on my doorstep and I’m feeling paralyzed. During these pandemic years, we’ve finally acknowledged our feelings for each other. Recently, we’ve both said “I love you” and “I can’t imagine my life without you in it” to each other, speaking freely about what prevented us for so long from acknowledging or voicing our feelings. The problem is, I’m with someone else who has been extremely good to and for me, and would be devastated to know the truth of how I’m feeling toward my friend. My friend, meanwhile, isn’t exactly in a datable situation (lives five hours away, takes care of an alcoholic parent, works a full-time dead-end job, is very involved with his band, very depressed). I’m willing to risk my pride by confessing my feelings, but I’m not willing to risk my stable life and happiness for him without knowing he’s willing to go all in with me. He’s made it clear that he’s not willing to do anything chaotic right now, even though he regrets his own self-control.

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I don’t want to let my feelings for my friend or the fantasies of us one day together go, but I can see that continuing to let them grow in secret is only going to sow disaster. I also don’t want to go no-contact with him because he needs friends in his life right now. Ultimately, though, I acknowledge this situation is untenable. I just don’t know how to resolve it in the least painful way possible.

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— Seven-Year Sitch

Dear Seven-Year Sitch,

You have gone this long knowing and loving him without making things any kind of official—you can go a bit longer. This is provided that his unwillingness to do “anything chaotic right now” is sincere and that he’ll be down to do so in the future. I should warn you that the idea that entering a relationship with you will be “chaotic” doesn’t bode well—perhaps your language is imprecise, but stated, it sounds like something that could crash and burn ultimately and then you would have upended your life for nothing. You should proceed with caution.

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I know you want to be with him, but the situation is OK as it stands, really. There’s a spectrum of affection on which our feelings for our friends reside, and you’re sitting on an extreme end. In the meantime, you’re in a stable situation that makes sense and doesn’t involve regularly driving five hours to see this guy who was oblivious about your love about him for a really long time. You learned to let these feelings play in the background, which is actually an impressive skill. You’ve honed it, keep using it. As long as you aren’t just biding time with your current partner and are capable of loving them as well (and your previous meaningful relationships while feeling the way you do about your crush suggests that this is at least possible), I think you’re already making the right choices. It’s not easy. Sometimes every option will suck a little, and the trick is to pick the one that is the most manageable. That’s called being an adult. You’re doing that. Stay friends with your crush, understand why you’ve made the choices that you have, and remain open to pursuing something if and when it makes sense. There are worst things than having multiple people at once that you care about.

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Rich

More Advice From Slate

My partner and I have been together for about six years now, and although the sex we have is great, we’ve never really discussed what things we might want to explore or try. I know about a few things my partner has done in the past, including a threesome with two men—and while if for some reason kind of bothered me in the beginning, I’ve begun to think about it in a sexual way a bit and it fuels some fantasies that I have had. Something about her being the object of desire in that way really turns me on…

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