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Dear How to Do It,
I’m from a big, tight-knit family where everyone is in each other’s business. Even though I live alone, my parents, siblings, cousins, etc. have keys to my apartment, and sometimes drop by. About a month ago, my new girlfriend “Becca” and I were having sex on the kitchen floor when my mom walked in unexpectedly. My mom was shocked and called her a rude name in surprise, and Becca pretty much ran for the shower and left me to deal with things.
The conversation was awkward, but things only got more awkward when they left. Becca now is weird about sex at my apartment at all, and if I initiate she will insist it has to be in the bedroom with the door locked. I tried to talk to her about calming down on this since awkward moments happen to everyone. I even told her how my dad walked in on me with an ex a couple of years ago, but she only got more upset and said I needed to start deadbolting the apartment when she was over if I was going to share my keys.
My family has come over multiple times when we’re just watching TV or making dinner when they should have been fine to come in but are locked out and teased me about the deadbolts. Becca has told me she’ll walk away if she doesn’t feel like there’s enough privacy. I feel like I’m caught in the middle between two pushy sides. How do I get them to leave me alone? I’m 35!
—Stuck in the Middle
Dear Stuck in the Middle,
Not to pigeonhole you, but I’m getting hardcore, New York tri-state area Italian from your description of your family dynamic. There’s something very Vinny from Jersey Shore about it. But even if I haven’t figured out your precise cultural background, you are nonetheless in the middle of a culture clash: Your family has one culture and Becca has another. I don’t know how you’re going to set boundaries in a family that seems to have few, save moving a few states over and creating an actual physical one. It’s you against the many, who have ingrained expectations and patterns of behavior.
But I do know that Becca has a right to her privacy. She has a right to have sex with you without being interrupted and called names. What you describe goes beyond “awkward moments,” and Becca is only “pushy” by your family’s invasive standards. I think you are less sympathetic to her requests (that read to me as entirely reasonable) because this is the environment you were raised in. It’s not your fault, but you do have an opportunity in front of you, should you choose to take advantage of it, to learn how other people live. Privacy is actually a fairly commonplace ideal in Western culture. Becca has given you an ultimatum, and now the ball is in your court.
How do you get your family to leave you alone? Well, you can start by asking them to leave you alone. You can tell them that Becca wasn’t raised in the same environment that you were and she values her privacy. Not exactly rocket science, and yet you’re resisting putting on your big boy pants, or are being lulled by your family into never having to. If you genuinely don’t want to change your family dynamic, you’re better off finding someone who has been raised in a similar one and already has experience navigating it or simply doesn’t care when her boyfriend’s mother walks in on her having sex and calls her a rude name (good luck with that one!). Maybe ask your mom if she knows any nice Italian (or whatever it may be) girls?
Dear How to Do It,
I’m a 26-year-old bi (but mostly gay) man. I’m trans. My boyfriend is 30, very gay, and cis. We’re a great couple in many ways and I love him, but my personal baggage is causing some internal struggles. I have had a number of hookups and longer-term friends-with-benefits setups over the years, but for about three years after I moved to my current smaller town, I was totally celibate. There was COVID, I didn’t plan to settle here, and frankly, I deal with a lot of lower dysphoria, and getting rejected by gay dudes can be upsetting for that reason (as a dysphoria trigger). My BF moved here after me and made pretty short work of the gay hookup scene. I’m not saying he’s slept with everyone but… close.
My problem is that I’m jealous. I feel like I can never be an organic part of the gay scene like that. I can never “just” hook up. I have to vet the person, disclose, make sure they “get it,” etc. I’m working on getting gender confirmation surgery, which will help the element of this that is just dysphoria, but we run into men he slept with every time we go shopping and it’s just getting worse. I really don’t think I’m jealous in the traditional possessive way, it’s just extreme FOMO of something that seems very universal for cis gay guys, that I can’t access because of a body I’m already really dysphoric about.
Feeling this way makes it even worse because now it’s a “thing,” and my BF is not good at comforting me about it. (The words “You need to understand: For gay men, what’s dangling between our legs is the first thing that matters!” were said at one point, and I WISH THEY HAD NOT BEEN!) Anyways, help me square this circle, please. I know there are a zillion ways to conceptualize this, and I would love to be sold on a less self-destructive one. I want to stop feeling like I’m living the sad papier mâché version of the life my partners take for granted. I want to stop being the plus-one in the gay community and find my own invitation (wherever it got mailed to by mistake).
—Honorary Member at Best
Dear Honorary Member,
Your boyfriend should be more sensitive about this, and frankly, what he said to you about genitals, presumably knowing well your issues with dysphoria, is pretty galling. There’s a difference between being honest and rubbing something in someone’s face, and he needs to learn it, quickly. With regard to his hookups, perhaps you’re getting too much information for your own good—a don’t-ask-don’t-tell arrangement might work better for you as well as a request for some discretion when you both happen to run into one of his tricks.
More generally, I’m sorry to read about how challenging casual sex can be as a trans dude. There’s not a ton you can do about how other people receive you, and many people have features that are not going to be everyone’s thing. But you’ve proven to yourself already that you are appealing to dudes—it’s just about finding the right ones. Yes, it requires explanation, and the extra work that goes into something that comes as second nature to some guys is a cross to bear, but it’s worth it when it works out, right? We’re all vulnerable to rejection when laying our desires bare, and despite the momentary sting when we aren’t chosen, we keep going because the moments of acceptance (and ensuing pleasure) make up for it.
Your partner should be helping with this. He’s not going to solve your problems, but he can support you; help you out; and show you that he, for one, finds you worthy of attention. If he’s not doing any work there, it’s worth asking for him to step it up. If he refuses or otherwise doesn’t, it’s worth rethinking the relationship.
I realize that I only have so much expertise to offer you, as a cis gay guy, so I showed your letter to porn performer Stevie Trixx (site NSFW), who is trans. I figured that, as someone who has sex for work, Trixx may have had similar experiences with stigma, and that his continuing employment suggests some degree of overcoming it. He’s also written about (again: site NSFW) changing ideals within the gay community as they relate to phallocentrism. I’m printing his email back to me (addressed to you) in full below:
This feels like a common experience among trans men, so I’m happy to take a crack at your question! I think there are some things that you and your boyfriend should discuss about your relationship more broadly, but let me speak to the specific piece about being trans. I’d encourage you to accept rejection as an inevitable part of life. As a trans porn star, rejection is an everyday part of my work in the industry. Some studios work with trans men, some don’t. Some creators are into us and some aren’t. It can feel really sensitive when we feel like the source of that rejection is our transness, the very immutable thing that makes us who we are.
But there are all sorts of different gay men out there, many of whom also fear rejection for their own reasons. Some are worried about the size of their penis or how much body hair they have or what they weigh. Hell, some of the hottest guys I’ve ever worked with have expressed some little thing that they worry makes them undesirable. If you can see that you’re not alone in these feelings and that we all face them, some of the sting dissipates.
Of course, I’ve had my share of disappointments. But, I find it helpful to remember that someone not wanting to be with me isn’t a comment on me personally. It’s just a true expression of how they’re feeling about our vibe. As much as possible, it’s best not to dwell on the reasons why.
But, here’s the flip side: From one trans guy to another, I know that being trans is hot and desirable, and special. We’re not everyone’s cup of tea, but there are people out there who love us and get it and understand what a gift it is. Maybe your boyfriend could even tell you some of the things that he finds especially desirable about you? If it’s a numbers game you’re interested in, that might just mean putting in some extra leg work. I know that some number of the people I contact to work with me are going to say no, but I have a much better chance at getting a yes if I send out 20 DMs than if I send out two. You miss all the shots you don’t take or something like that.
And yeah, cruising isn’t as easy for us as it is for cis men. Trans men are treading new(ish) ground in the gay community, and there’s still a lot of awareness-raising to be done. When it comes to meeting people in person, confidence is key. Figure out what it is that’s sexy and unique about you and then put that on blast. Self-assuredness is a magnetic quality in anyone, cis or trans. My most practical advice is probably just to try out the apps. I’ve found that the apps where you can pre-disclose that you’re trans are usually the simplest way to find and meet people who are into trans men. Trust me, they’re out there! Wishing you the best of luck and lots of hot hookups!
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Dear How to Do It,
Please help, I am a mid-50s, recently divorced male with three grown children that was in a nonsexual marriage for 15-plus years. I was faithful to my wife but now that I am single I am feeling overwhelmed with the dating scene and the possibility of sexual activity. I was very sexually active in my 20s and early 30s but feel incredibly out of practice now. My biggest concern is immediate premature ejaculation with any perspective partner and the ensuing embarrassment. I also have no idea about post-50 grooming habits. I haven’t tidied up down there for almost 20 years. I did a light mow but now I’m worried that it’s either too much or too little. I am also concerned about how to even bring up topics of STDs or protection from potential dates for fear of immediate rejection. I have gone on several nonintimate dates but there is someone that I think is ready to progress but I’m honestly scared to even begin. Do people still french kiss? Do I ask for consent before certain acts? It just feels so different now.
—Post 50 and Scared to Death
Dear Post 50,
Relax, this is supposed to be fun, and it probably will be once you get over the hump and back to humping. Some of what you’re worried about—discussing sex beforehand, for example—is actually a potential buffer that could help you ease back in. These conversations don’t have to be fraught. They could actually give you the kind of direction that you currently feel you are without. Asking for consent doesn’t have to be accompanied by formalities or be written in calligraphy on heavy card stock. You can certainly ask, “Can I kiss you?” but you can also say something to the effect of, “I’d like to kiss you,” and proceed after an affirmative response. Another example: “Do you want to try getting on top?”
It really will all come down to the comfort levels of your partner, which is why a lot of your anxiety is hard to mitigate from where I’m sitting. Too many variables! I have no idea how much pubic hair your potential partner likes, or how much tongue she enjoys in her mouth, but from my gay experience, yes people still French kiss (a lot!), and I’m right there with you on the pubes. Doing a light mow and being worried about it being too much or too little is the story of my life. I haven’t had any complaints, regardless, and I doubt you will (if you do get some feedback, that’s all it has to be—people expressing their personal taste about such things doesn’t have to be a cataclysm—and if you happen upon someone so particular that your level of pubage is a dealbreaker, do you really want to be with her anyway?). I know the potential for premature ejaculation can be daunting, but you’ll just have to feel your way through—making a joke out of it (“You can tell I haven’t done this in a while”), casting it as a compliment (“Look at how excited you got me”), and offering to help get your partner off by means of her choice that don’t involve your hard dick should sail you through. You can refer to the suggestions in this recent column regarding PE for more, but cross that bridge when you get there.
Dear How to Do It,
I am a 32-year-old, cis gay man and have been with my husband “Marc” (34) basically monogamously for nearly 14 years We’ve always been very open about our attraction to other men and have each hooked up once or twice under varying circumstances. Eventually, we discovered mutual interests in sexual compersion and cuckolding but have yet to invite a third into our bed for real. We were essentially ready before the pandemic forced a pause, and my fragile immune system continues to require excess caution.
Here’s the thing. I met “Jeff” online six years ago now. He is married and polyamorous and our relationship began with us having long, detailed roleplays about him railing Marc while I watched. Jeff lives across the country so we have not met in person yet. Despite this, after all these years and post-pandemic, he has become my closest male friend. We text constantly and talk about our lives and families. Sex and kinks come up frequently and we get off occasionally (with consent from Marc and Jeff’s wife). We FaceTime while watching big UFC matches, shoot the shit, and game together. This is not how I usually bond with other men and I’ve been loving every second of it. I think our spouses saw even before Jeff and I did that we have been connecting a little more deeply than just friends. We are starting to plan a visit.
Marc has been wonderfully accommodating about this and if anything, we feel especially close to each other lately, even as he has explicitly given me space to explore my building intimacy with Jeff. However, this is all new for us, and Marc also understandably feels a bit jealous and left out of the fun sometimes. Jeff is still interested in Marc and we are happy to include him in most activities, but Jeff and I absolutely have our own dynamic that Marc is simply not a part of. Ultimately, Marc falls much more on the side of being happy that I have connected so strongly with somebody I value so deeply, but it’s very complex. We are planning on going to couples’ counseling and getting ourselves a copy of The Ethical Slut ASAP, plus I’ve been reading what I can online, but in the meantime, what else can I do to help make this situation easier for Marc? Our communication has been extremely open, all parties are discussing boundaries, and Marc and I have talked about it a lot because this situation is so complicated, but it’s also a ton of fun. I feel showered with love and almost like I’m getting away with something, but Marc insists he is basically happy and just needs space to discuss his feelings. Am I… doing it right?
—Embarrassment of Riches
Dear Embarrassment of Riches,
Sounds to me like you are! With ethical nonmonogamy, it’s important to defer to the most sensitive person in the relationship. You’re doing that. There might always be some jealousy on Marc’s part, and he may always feel left out of a dynamic that you admit only intermittently involves him. But he’s a big boy, and as long as these negative feelings don’t overwhelm him and he can mostly pull through via the positive ones, you’re fine. Open situations are complicated, and negative/positive feelings don’t have to cancel each other out. They can just co-exist—that’s where logic does some heavy lifting. One may say to himself, “I’m not 100 percent happy about this, but my partner’s happiness makes it worth it.” Acknowledge this explicitly and let him know that if it ever gets to the point where Marc cannot tolerate your relationship with Jeff, you’ll talk about it and be open to reevaluation.
But so far, so good. That you’re concerned at all with Marc’s relatively minor complaints suggests that your heart is in the right place and that you know what you’re doing with it. Keep talking. Be aware of his comfort levels regarding what you share with him about Jeff—some partners prefer a don’t-ask-don’t-tell arrangement, some want to hear everything, and some feel differently depending on the day. I’d recommend not spending all your time with Jeff alone. If Marc is down, try to hang, just the three of you (even if it’s in a non-sexual context) so that Marc can see firsthand that Jeff poses no real threat to what you have with him— that the relationship with Jeff is additive, not divisive. Also, The Ethical Slut is a classic for a reason, but I always recommend Tristan Taormino’s Opening Up, as it’s very practical. So check it out.
More Advice From Slate
This is probably going to sound crazy but here goes. I am 67 and I’ve been married to the same woman for 43 years. I know that before we married, she had been with about 10 other men sexually. I am only about 5.8 inches when fully erect, and for some reason that I can’t explain, I have been bothered lately wondering how many of the men that she had been with were bigger or even much bigger than me.