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 have been with my boyfriend for about two years. He is 37, and l am 49 (I divorced four years ago). I am so into this guy and enjoy our time together every day—he always makes me smile and makes me laugh most days. I feel very secure and happy with him when we’re together. He is extremely good looking and has a smile and eyes that can light up a room, along with a very athletic strong body. He’s very intelligent, street smart, a good provider, and takes me nice places all the time. We never have sex, but he will orally stimulate me and is so good at that. It’s amazing sometimes.
It has taken me a while to figure out that he is gay. My friends actually pointed out things about him and said he might be gay. I started to put together the signs l was missing. Once l convinced myself that there were some strong signs, I asked him several times over the course of many, many months if he was gay. He always had joking answers, but he finally admitted it to me one night that, yes, he is secretly gay. I love this guy so much. He takes care of me financially, gives me a nice home to live in, and takes me nice places all the time. I find him extremely attractive, as many women do. He is just so good looking and a joy to be with.
I am lost in emotions, but so, so in love. He now says we’re a good couple together and that I am the perfect cover girlfriend for him. But I’m not sure where our future is, what my place is, and he has no answer for that. We never have any sex anymore and never really did. When we first started dating, he could never maintain an erection and was standoffish. Now I know why. l have to almost beg him to go down on me. He tells me to just use my vibrator. I am very scared to leave him because I love him so much. I fear that someday he will find a man to have a relationship with and finally come out of the closet. Sometimes, l wish he would just come out of the closet, but then my selfish self doesn’t want to encourage him to do that. I am not sure what to do.
Well, if there’s one thing that’s clear about this guy it’s that he knows how to treat his beard—he’s slathering you in the lifestyle equivalent of Pasha de Cartier Edition Noire Scented Oil.
While I am willing to take you at your word that your love for a self-proclaimed gay man makes the idea of leaving him so troubling, your financial dependence on him complicates the situation greatly. It is, in fact, inextricable from your love and fear. Would love alone be enough to keep you in this relationship? Be honest with yourself: You’re scared to leave him not just because you love him but also because it would shatter your lifestyle, right?
I’m all about people making their own way. The stock life trajectories prized in our culture (heterosexual relationships that yield 1.9 children, etc.) I think are often adopted because they feel like safer bets, and not necessarily because people are innately inclined to walk in those straight lines. Because your situation so deviates from many of the values that are supposed to underpin the unions of life partners, this ostensibly hetero arrangement between a gay man and a (I’m presuming straight or fairly close to it) woman is, in a funny way, pretty damn queer. And I support pretty-damn-queerness implicitly.
Of course, there’s a but. What I don’t like about the relationship you describe is the blatant disparity in power due to not only the financial setup but also what you represent to each other. To him, you’re the “perfect cover girlfriend.” He sees you as a “good” couple presumably because that is how he figures you appear from the outside. To you, he is a partner; to him, you are a decoy. How could that ever sustain itself? And besides, what is he—the reincarnation of Tab Hunter? Why does he need a cover girlfriend, anyway?
I also can’t condone your sexual dynamic. Now that he has come out to you, he has no real impetus to improve your shared sex life. Having to nearly beg for oral sex that is only occasionally amazing is as good as it’s going to get for you if you stay. You could open the relationship, I suppose but, sigh, that will probably further complicate a situation that already demands mental gymnastics. You’re not sure what to do, but it seems pretty clear that by staying with a gay guy, you’re settling. You have to ask yourself if it’s really worth it to you.
Dear How to Do It,
After three passionate, wonderful years, my girlfriend and I have started seriously talking about bringing another man into our bedroom for the experience and to satisfy a fantasy of ours for the first time. This is more for her, and we are very secure and safe in our relationship and comfortable in pursuing this. Our concern is that she’s very nervous about getting any STDs, and obviously I share that concern. We want to do this safely and anonymously. How can we assure our safety? What steps should we take to make her comfortable? It may be a one-time thing or regular if we’re comfortable with that one guy. Is there a particular sex act that we should avoid altogether? She’s not 100 percent convinced that condoms are the solution, so is there something else we should be using? Thank you in advance for your guidance on this.
Dear Safe Mode,
I hate to pop your condom, but you cannot assure safety. You can only attempt it. HPV is transmittable via skin contact (and nearly all sexually active adults reportedly contract the virus at some point in their lives). Herpes, also transmittable skin-to-skin, is more common than blue eyes. Then there’s the bacterial stuff: Your gonorrhea, your chlamydia, etc. They’re all highly contagious, including via oral sex, so if you’re super worried about those kinds of invaders, condoms and dental dams should be used. Going on PrEP for a single encounter is a bit much, but should you feel worried about HIV transmission after the fact (say a condom breaks or—dramatic gasp—you neglect to use one), know that you can go to a doctor for PEP (post-exposure prophylaxis), in which antiretrovirals are administered for 28 days to prevent HIV transmission after potential exposure. (It’s crucial that this cycle is started within 72 hours of the potential exposure.)
Anal sex tends to be more associated with transmission risk because of how delicate anal tissue is. Meta-analyses have suggested that receptive anal sex carries 18 times the risk of HIV transmission that receptive vaginal sex does. I can’t bring myself to advise against anal (it’s too good!), but if you’re superparanoid, there you go. I also think you should just be less paranoid about STDs, period. Get vaccinated for HPV. Relax about herpes, which became a “sexual boogeyman,” according to an article that ran on this very site this year, as a result of overzealous reporting. Get tested after your encounter to ensure you don’t have a bacterial infection that could lead to complications if untreated. And have fun: Life is worth living, and sex is worth having.
Dear How to Do It,
I’m a late-30s, recently divorced man with children. I’ve lived a pretty vanilla, hetero sex life. With my newfound singlehood, I’d like that to change, but complications ensue. I have a strong attraction to pre-op trans women that I’ve suppressed for years. Unfortunately, pre-op trans women are a terribly small segment of the population where I live, and I have no idea how to discreetly find my way into this community. However, in the near future, I’ll be heading to New York for a work engagement. There’s a thriving trans community there, but I have concerns about how a straight-laced, office-dwelling visitor to this community will be accepted. Sex workers are an option, but I’d like more than just a physical experience, and from my research, this type of date (drinks, dinner, nightcap) seems a bit out of my price range. With that said, how can I better engage the sparse but extant trans community where I live, and what tips do you have for finding a willing participant while in New York?
Many geolocation apps that for years were posited as spaces for men interested in having sex with men have, in recent years, expanded to include a visible trans/chaser demographic. Grindr is one of them. I am not at all suggesting that you give that security-breaching company your money, but if you do, a paid account will yield more precise filtering options. You could also try advertising on Doublelist’s Straight for Gay board, which, despite its name, tends to be populated with self-identified straight guys looking for trans women. (There’s also a Gay for Straight board if you want to try the other way, though that tends to have a lot of cisgender posters.)
I’m not quite sure what your desired sweet spot is here; it seems like you want a bit more than just sex but not quite the tasting menu that a sex worker might require. Nonetheless, you seem more inclined toward the casual type of encounter, so let me remind you not to be a dick. Plenty of trans people are looking for casual sex as well, and in a forum devoted to finding one, such as a hookup app, objectification is the name of the game for many regardless of identity. But know that there is a noted tendency of straight guys to regard trans women as only sex objects. Sensitivity and conscious humanity are crucial here. I’ve given you two very clear pathways to the kinds of connections you’re looking for; do me a solid and behave yourself in these pursuits. Don’t leave my city more messed up than how you found it. Thanks in advance.
Dear How to Do It,
I’ve been dating a great guy for a couple of months. We have great chemistry, and he’s extremely affectionate in bed. The only problem is that he can’t seem to hold an erection at night, so we’ve been having almost exclusively morning sex since we started hooking up. And even though the sex is great for me (I am one of the lucky women who orgasms at the drop of a hat), I’m not sure he’s actually finishing. We’ve been together long enough that I want to address this, but not long enough that I know how he’ll react if I do. Any ideas on solution-oriented approaches?
Dear Morning Person,
Lead with the positives—highlight everything that you did in your letter. Tell him that sex is great for you, you appreciate how affectionate he is, he makes you come consistently. Then ask him what he thinks about your sex. Perhaps he’ll reveal whatever issues he’s experiencing then and there. If he doesn’t, ask him if there’s anything that can be improved. His issue could be standard erectile dysfunction stuff—causes vary but treatments (like meds) are pretty reliable. Or maybe he has a fetish that he has not told you about. Maybe there’s something he wants in bed but doesn’t feel he’s had the opportunity to ask for. Obviously, he knows something is up—he’s attached to that finicky dick of his, and he’s tried to circumvent its issues by scheduling morning sex. You’re not unreasonable for wanting to discuss the elephant in the room that you’ve both named and gazed into the eyes of while thinking, “My, what a complex creature!,” and he’d be unreasonable to interpret you as such. But be willing to accept what he says, and keep the door open for him to reveal more at a later date. He might have a really hard time reaching orgasm to the point of not even wanting to bother. If he’s happy to continue the sex that you’ve been having and you’re coming at the drop of a hat, I don’t see much of a reason to start changing things. Enjoy.
More How to Do It
My girlfriend and I had our first threesome a few nights ago. She felt most comfortable trying it out with a guy first, and I was fine with that. We found a man on an app. I was nervous, but it was actually just comfortable and fun. Then things took a turn about halfway through—he was watching her go down on me, and I got really, really hard, and he asked if he could join her. In the moment, we just kind of went with it, and I came shortly after, possibly harder than I ever have. It was great—except now I feel like I’ve learned something about myself that I don’t really know how to process. Is it just that it was hot in the moment? Or could I be bicurious and not know it?