I’m a 45-year-old single gay cis man out there in the world. I met a 50-year-old cis married man on Grindr. We had hot sex and have been hitting it off ever since. Here’s the problem: I was under the impression at first that he and his wife practiced some form of ENM or had some version of a “Don’t Ask, Don’t Tell” agreement. At this point, however, I know that all the man-on-man sex he’s having with me and others is just old-fashioned cheating. Among other pieces of evidence that he’s cheating: He’s having his PrEP and DoxyPEP mailed to my address (good on him for being proactive about this) and he goes out of his way to cover his tracks in other ways. More context: His spouse is the breadwinner and he stays at home. Housework is work, of course, and he does the housework, but he has no income. They’ve been married for more than 25 years and they haven’t had sex of any kind in at least eighteen years. He jokes about maybe having a sex addiction and is also a little smug about getting away with fucking whoever he wants, whenever he wants. Do you think the wife should be tipped off to what he’s doing? She is going to find out eventually… I’m certain of that. Also, he’s got a teenage son who is gay and out and he can’t seem to see the problem of his being in the closet while his son is out.
Is this guy a lost cause? Should I cut ties? Or is there a way forward?
Couldn’t He Enjoy And Tell
You clearly wanna tell this guy’s wife he’s been cheating on her — I’m getting subtle “aggrieved mistress” vibes from your question — but I don’t think you’ll be telling his wife anything she doesn’t already know. She may not know her husband is bisexual and fucking you and God only knows how many other men, CHEAT, but she most likely assumes he hasn’t been celibate for the last eighteen years.
That said, being confronted with the proof — of his cheating and his bisexuality — could cause this woman pain, CHEAT. For all you know, he’s the reason their marriage is sexless and she has lived every day for nearly two decades with the sting of her husband’s sexual rejection. So, why does she stay? Well, sometimes a person is able to limp along in a sexless marriage because they believe the sexual deprivation is mutual — they believe this misery is a load they share — but finding out your spouse is out there taking loads while you read the books and make the appointments… yeah, this guy’s wife could go from resigned and content to wounded and devastated before she finishes reading your email.
But maybe everything this guy has told you about his marriage is true — always a big leap when a married person wants to get into your pants — and his wife is one of those women who doesn’t wanna fuck her husband but won’t give her husband permission to fuck anyone else. If that’s the case, then your lover is only guilty of doing what he needs to do to stay married and stay sane. And if there are good reasons why they stay together — financial dependence is one reason people stay, CHEAT, but so is emotional/social dependence — then your email could wind up doing more harm than good.
Look, you’re free to find it sad that this man isn’t out to his wife or his gay kid, CHEAT, but I don’t think you have a right to blow up his life — his thoroughly compromised life — because you think it would be better for all involved (presumably yourself included) if he was out. It sounds like this guy is a bit of an asshole… and it sounds like you caught feelings for him at some point… and now you feel like you’ve been used. But outing a cheater for cheating when you’re done cheating with him (or he’s done cheating with you) is always a bad look.
P.S. If the “way forward” you’re imagining is some sort of future where you’re with this guy… yeah, maybe you tell him what you’re feeling instead of telling his wife what he’s been doing.
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I am a 40-year-old cisgender bi woman living in the Midwest. I have a question about one of my best friends, a trans woman. I’ve known this person for over fifteen years, most of that before their transition. They grew up as a white man, middle class, and didn’t deal with any of the things that women deal with growing up. I’m referencing harassment and assault, especially with the recent case in the news of the students at Cornell University. This individual grew up to be a relatively successful man with a six-figure income, nice house, and a pretty average life. They came out as trans a few years ago and I’ve been incredibly supportive during their transition. The thing that I’m having trouble with is their newfound “feminism.” When we talk about the struggles women face, they speak as someone who has been through and lived through those experiences. As an AFAB woman who grew up in the 1990s and 2000s and has dealt with harassment and sexual assault, this is really upsetting to me. I absolutely love my friend, but it really hurts me when they claim to understand the plight of women in America when they have identified as a woman for less than three years. How can I bring this topic up without turning it into a major argument? Am I being too sensitive? Should I just agree with them and move on? I need help here.
That’s Really Annoying
I’m not a woman, TRA, but I do listen to women (when I remember to close my mouth) and I try not to talk over women (which is easier to do with my mouth closed). I like to think that all that listening has given me — a cis man — some understanding, however imperfect and incomplete, of what women face. So, it’s possible your friend… if she was listening before her transition… has some understanding herself.
But your annoyance with your friend, this recently hatched egg, is likewise understandable.
I’ve been out and gay for — OMG — more than forty years, TRA, and nothing annoys me more than having gayness explained to me by someone who has been out and gay for forty minutes. In some cases, these newly out guys are being thoughtless. But in others, TRA, the newly out guy isn’t talking to me. They’re not saying things I need to hear… they’re saying things they need to hear. But my M.O. is the same in both cases: I let them talk. Even if it means having to listen to someone who was born in 2002 explain to me just how bad things were for gay people in the 1980s, I let them talk. They either realize they’re being ridiculous (“I mean, I don’t need to tell you this!”) or they hear what they needed to hear and the conversation moves on to other things. (I do reserve the right to blow up when a newly out cis gay man tries to tell me that cis gay men played no role in the struggle for gay rights — we just partied, fucked, and died while nonbinary asexuals did the heavy lifting — or that the gay rights movement was hijacked in the 1990s by gay men who wanted to throw themselves wedding showers. Those are fighting words.)
So, my advice: Let your old friend run her mouth. Don’t argue, stare blankly, and change the subject when there’s a lull. Here’s hoping your friend, like those newly out gay boys, eventually gets this shit out of her system. But if she doesn’t — if she literally can’t stop explaining womanhood to you — feel free to spend less time with her.
I’m a gay twunk in a “one-sided” open relationship: I fuck other guys and my fiancé does not. (It was his idea!) When I have a Grindr date, I tell them him my fiancé is my roommate to keep it simple. My fiancé likes listening to me get railed by another man in our bedroom and the sex after the other guy leaves is so great that my hookups sometimes feel like foreplay. My question: One very annoying guy in my extended gay friend group constantly accuses me of violating my hookups’ consent by using them as “bulls” in cuckold scenes they didn’t agree to participate in. Am I ethically obligated to tell these guys before they come over that my roommate is actually my fiancé and that he’s not playing video games with his headphones on (what he pretends to do when I walk a guy past him) but actually listening? (So, the louder we are, the better?) Or is this annoying gay friend just jealous and annoying?
Hot Future Husband
P.S. The joke is on my annoying gay friend: Not only does my fiancé get off on me cucking him with other guys, he gets off on knowing some of our friends know. So, if I’m going to be scrupulous about disclosure and consent, I should probably tell my annoying gay friend that my fiancé’s favorite kind dirty talk during sex is listening to me list off the names of my friends who know he’s a pathetic cuckold that I cheat on whenever I want?
P.P.S. Seeing this letter in your column— if you choose to respond — is going to turn my fiancé on, Dan, so don’t use my letter if you don’t consent to that!
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