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The weekly sex advice column that started it all

The Watcher

Joe Newton

I’m a married gay man in Southern California. I also have a boy who has his own partner. Both my boy and his partner used to live nearby. But in August they moved to Seattle. The “why” of their move continues to bother me. They didn’t move for a job, or to be closer to family, or any of the other reasons people normally relocate. My boy said it was a combination of the weather and people. The problem, as I see it, is that both my boy and his partner have introverted tendencies—they don’t go out much—so I don’t see how the weather or people really make a difference.

The bigger issue is that my boy has tried to “pimp” his partner on me throughout our relationship. I usually rebuffed his suggestions, but one night I gave in. His partner and I started to kiss and feel each other up, and it was fine. The weird thing—the thing that troubles me to this day—was how my boy reacted. He watched us with this bizarre look in his eyes, like he was really getting off on watching the two of us go at it, like some creepy voyeur. His expression freaked me out so much that I ended things and gave some dumb excuse. I recently had an encounter with another person who had a similar experience with my boy. He described how he would cam with my boy and how my boy would always bring his partner in.

My boy had expressed to me on multiple occasions how his partner cannot find sexual partners on his own. I think the real reason my boy moved was to find a new dating pool in the hopes of eventually finding a match for his partner. If my thoughts are correct, then my boy did a horrible thing to our relationship. I don’t know much about cuckolds and I’m looking for advice. How do you have a relationship with a boy when that boy’s sole focus is the sexual satisfaction of their partner?

Confused About Lad’s Departure And Deceit

Moving to Seattle for the “weather” seems a little counterintuitive. But I can see why a pair of introverts might prefer gray Seattle, where I live, to sunny Southern California. When it’s nice outside, you feel obligated to go outside. But it’s never nice outside in Seattle. We have a rainy season that stretches from November through July (too wet to go outside) and now, thanks to catastrophic climate change, we have a wildfire season that stretches from August through October (too smokey to go outside). So, looking out a window in Seattle you never think, “I should go for a walk and risk a chance encounter with another human being,” but rather, “I should go back in the basement and keep playing video games.”

As for the people here in Seattle… even the most extroverted newcomers complain about the “Seattle Freeze.” But if your boy and his partner are just looking for fuckbuddies, well, they’re in luck. The dick up here is damp nine months a year and tastes like smoke the other three, but there’s plenty to go around.

As for the host of other issues you raise…

Look, I’m not your boy, CALDAD, so I can’t tell you exactly what’s going on in his head. But I do feel confident saying he’s not your boy anymore. Not only did he move away (with his partner) and leave you all alone in Southern California (with your husband), CALDAD, but you seem to hold him in contempt—contempt for his motives, his kinks, and his partner—and contempt is a hard place to come back from. So, since you aren’t in a relationship with him anymore, you don’t have to worry about making this relationship work. (I’m sorry if that seems harsh, CALDAD, but better to hear that from me than from the commenters.)

So, is your ex-boy a cuckold? He could be. Based on your description of his behavior the night you hooked up with his partner, it certainly sounds like he gets off on watching his partner get fucked by other guys. It’s also possible that he shares the dick he’s getting elsewhere with his primary partner. There’s nothing wrong with being a cuckold, of course, and there’s nothing wrong with “pimping” a partner out… so long as 1. your partner wants to be pimped out and 2. you’re not pressuring other guys to do things with your partner that they don’t wanna do.

But if your ex-boy was only interested in you for his partner, CALDAD, he was certainly playing the long game. Establishing an ongoing D/s relationship with a married man when all you really want is someone to fuck your partner in front of you… that seems like an awful lot of effort when Grindr is full of men who would be up for fucking your ex-boy’s boyfriend while he watched without him having to go through the trouble of entering into a long-term relationship first. Setting you up with his partner may have been an interest, but I don’t think it’s fair to say it was your ex-boy’s sole interest.

And honestly, CALDAD, I find myself wondering what you expected from your ex-boy when you started to fuck his partner in front of him. Did you think he was going sit there impassively, with a look of total indifference on his face, not feeling anything in particular? If so, CALDAD, that wasn’t a very realistic expectation on your part. And I suspect if he had sat there looking bored or indifferent, you would’ve found that just as weird and off-putting. If I was fucking some guy’s boyfriend in front of him, CALDAD, I would hope that guy got off on it. Hell, I would call it off if the guy whose boyfriend I was fucking didn’t react like some creepy voyeur.

Frankly, CALDAD, I don’t think your ex-boy did a terrible thing. He was honestly into you, that’s why he was your boy, and he wanted to share his partner with you. If you didn’t want to fuck his partner, you should’ve continued to say no. Once you started to fuck his partner, you should’ve wanted (and expected) your ex-boy to enjoy the show.

P.S. On the off chance that CALDAD’s ex-boy is reading this: Welcome to Seattle! Cuckold or pimp, both or neither, you need to be clearer with your sex partners (in person, online, wherever) about what you’re doing, what you want them to do, and why you want them to do it. There are plenty of guys out there into threesomes, cuckolding, and guys who are pimping out their partners, so there’s no need to be a manipulative-by-default creep, which is how you risk coming across when you aren’t clear about what you’re doing (sharing your partner) and why (you’re a cuck or your partner has no game or both).


I read your column a lot and there’s a pattern I’ve been noticing. A straight guy writes in and says he’s straight and likes pussy, but he’s recently discovered that he’s also attracted to trans women. And then they ask something like, “How should I describe my sexual orientation now?” To which you reply with something like, “You are straight. Trans women are women, they just happen to have dicks.” Great answer! I don’t disagree, but if I were responding I’d write, “You’re not gay, because trans women aren’t men. Trans women are women with dicks. Since you are attracted to women, you can keep on identifying as straight if that’s what feels right. Or you can identify as queer.” Queerness, as I understand it, is an expansive term that refers to anyone whose sexuality or gender expression falls outside of conventional expectations. To me it seems appropriate for these straight men to embrace the term “queer.”

Mulling Over Labels

While you might think it’s appropriate for straight men who sleep with trans women to identify as queer, MOL, lots of trans women disagree.

“It’s deeply problematic when people hear that a famous man is with a trans woman and they automatically think that he’s gay, because that is disavowing the womanhood of trans women,” Laverne Cox said during a conversation with Angelica Ross about the struggles of dating as a trans woman. “You can be into a trans woman and be completely straight.” (Cox and Ross spoke on an episode of Cox’s talk show If We’re Being Honest.)

So, any straight man who thought of himself as queer because he was into and/or fucking and/or with a trans woman would be guilty of disavowing the womanhood of his own partner. And any gay sex-advice columnist who urged straight men who were into/fucking/with trans women to think of themselves as queer would be pretty quickly terfed out of the advice racket. But it does seem to me that a straight man who openly dates trans women, while no less straight than any other straight man, is definitely something more than most straight men—more confident, more secure in his own sexuality, more likely to be a good partner to any woman he winds up with, cis or trans.

Now, some cis men who date trans women aren’t straight; some cis men are bisexual or pansexual or omnisexual, as Cox pointed out on her show. And there are trans women out there who are queer and straight. Which is where it really gets complicated. A straight cis guy dating a trans woman is definitely in a relationship with a queer person; he’s arguably in a queer relationship himself. But being in a queer relationship—being the cis straight boyfriend of a trans woman or the cis straight wife of a bi guy or the allosexual partner of an asexual—doesn’t make a cis straight person queer themselves.

But you know what? The fucking world is on fire and if a cis straight guy who’s with a trans woman wants to identify as queer—if he wants to round himself up to queer—and the woman he’s with is okay with him embracing the term “queer” for himself, he can call himself queer.

P.S. Not all trans women have dicks.

I’m a married gay man in Southern California. I also have a boy who has his own partner. Both my boy and his partner used to live nearby. But in August they moved to Seattle. The “why” of their move continues to bother me. They didn’t move for a job, or to be closer to family, or any of the other reasons people normally relocate. My boy said it was a combination of the weather and people. The problem, as I s

Subscribe now for only $25/year to continue reading! Does Dan agree with MOL, or is the str8-men-who-sleep-with-trans-women-are-actually-queer issue more complicated than that? (And Dan cites Laverne Cox, who helps illuminate how some trans women feel about it.)

ee it, is that both my boy and his partner have introverted tendencies—they don’t go out much—so I don’t see how the weather or people really make a difference. The bigger issue is that my boy has tried to “pimp” his partner on me throughout our relationship. I usually rebuffed his suggestions, but one night I gave in. His partner and I started to kiss and feel each other up, and it was fine. The weird thing—the thing that troubles me to this day—was how my boy reacted. He watched us with this bizarre look in his eyes, like he was really getting off on watching the two of us go at it, like some creepy voyeur. His expression freaked me out so much that I ended things and gave some dumb excuse. I recently had an encounter with another person who had a similar experience with my boy. He described how he would cam with my boy and ho

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