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I’m a 49-year-old gay man. I’ve become friends with a 21-year-old straight guy. He’s really hot. He’s had to drop out of college and return home. I know he needs money, as he hasn’t found a job yet and has resorted to selling off old music equipment. I would love to have some sweaty clothes of his, namely his underwear, but I’d settle for a sweaty tank top. Is it legal to buy someone’s underwear? He’s a sweet guy, and I don’t want to freak him out by asking something so personal. How do I broach the subject? —Lustfully Obsessed Stink Seeker
It’s perfectly legal to buy and sell used underwear, LOSS, so there’s no legal risk. But you risk losing this guy as a friend if you broach the subject. You can approach it indirectly by saying something like “So sorry to hear you’re selling off your music equipment. You’re young and hot—you could probably make more money selling used underwear or sweaty tanks.” Then follow his lead: If he’s disgusted by the suggestion, drop it. If he’s into the idea, offer to be his first customer. —Dan Savage
I’m a 52-year-old straight guy from Australia, 29 years married. About eight years ago, I met a lady through work and we became friends, with our friendship continuing after she moved on to a different job. We meet up for coffee occasionally, and we share a love of cycling and kayaking, which we also do together on occasion. Both of us are in long-term, committed monogamous relationships. Our friendship is strictly platonic, sharing our love of riding and paddling. Neither of our partners shares our interest in these outdoor pursuits. My friend does not feel safe doing these activities alone, so often depends on my company for safety as well. The problem is that my wife gets jealous of the time we spend together and wants me to cut off contact with my friend. My wife does not trust my friend not to “take advantage” of our friendship. My relationship with my wife is the most important one in my life, so I am prepared to say good-bye to my friend. How do I say good-bye in a respectful, caring, and loving way? If she asks why we cannot be friends, I don’t want to tell her, “Because my wife doesn’t trust you not to try to get inside my pants (or cycling shorts),” as that would be hurtful. I don’t want to lie, but telling the truth would be damaging to my friend. —Paddling And Riding Terminates
Your friend is going to waste a lot of time wondering what she did wrong, PART, if you don’t tell her the real reason you can’t hang out with her anymore. And guess what? This not knowing will cause her more hurt than the truth could. So tell your friend the real reason she’s out of your life: You’re terminating your friendship because your wife is an insecure bag of slop who regards her as a threat. Your friend has a right to know she’s as blameless as you are spineless. Forgive me for being harsh, PART, but I think standing up to your wife, not dropping your friend, is the best approach to this situation. —Dan
Before I got married, I asked husband repeatedly about fantasies and kinks, so that we had full disclosure going in. It led to some fun stuff in the bedroom, but we’re both pretty low-grade kinksters. Now I realize that I do something that I have never told him about: It’s the way that I masturbate. I started when I was 5 or 6, because it felt good. Got chided by parents and teachers for doing it in public and learned to keep it hidden. And so ever since, it’s been my secret thing. I think it has helped me orgasm in that I knew how early on, but it has also made it more difficult to come in positions that don’t mimic the masturbating position. Husband likes the idea of me coming in different positions, and I’ve managed now and again, but he doesn’t know why I’m set in my ways. We’ve been together for 10 years, but I have never shared this. Should I tell him? Part of me is afraid that he will think I’m weird. But more than likely, he’ll just want to watch me do it. Still, it’s kind of nice having this one thing that belongs only to me. —Secret Masturbator Obligated Over Spanking Hotness?
You could hold this back, SMOOSH, and keep it all for yourself. But I don’t see why you would want to. As sexy secrets go, “There’s one particular position I like to masturbate in” is pretty boring. Unless you need to be positioned on top of a cadaver or under your dad or beside a life-size Ted Cruz sex doll to get off when you masturbate, there’s really no reason to keep this secret. —Dan
I am totally with your German friend, who wouldn’t do Nazi role-play “in six million years.” I’ve been in a similar position—not quite Holocaust level, but not far off. I’m a white British guy. A while back, while living in the UK, I was dating a woman from Bangalore. She revealed—after her face lit up when I dressed in a way that made me “look like a colonialist” (her words)—that her deepest fantasy was to be an Indian slave girl raped by an English imperialist. And then, living in the US a few years later, I was dating a black woman. We got to talking about the kinks of exes. I told her about this one, and she revealed that her own fantasy was to be the slave on a 19th-century plantation, raped by her white owner. How about some advice for the human fetish objects in these scenarios, Dan? I didn’t want to stigmatize these women for their sexual desires, and I wanted to be GGG, but it was, frankly, hard (or not, as it were). Being asked to act out roles I feel guilty about, and to use the kind of racial epithets I make every effort to avoid… the guilt is a boner-killer. Any tips on how a GGG partner can get past this kind of mental block and at least act the role enthusiastically enough to fulfill the fantasy? Or was a subsequent girlfriend’s outrage about my willingness to indulge such socially regressive fantasies justified? —I Might Play Every Role I’m Asked Less Ideologically-Scrupulous Motives
Actors play Nazis in hit movies, British colonialists for prestigious BBC miniseries, and serial killers on long-running television shows. I don’t see why playing monsters in entertainments devised for millions wins Oscars (Christoph Waltz for playing a Nazi in Inglourious Basterds), BAFTAs (Tim Pigott-Smith for playing a brutal colonialist in The Jewel in the Crown), and Golden Globes (Michael C. Hall for playing a sociopathic serial killer in Dexter), but playing a monster for an audience of one should outrage “subsequent girlfriends” or anyone else.
My advice for people asked to play monsters in the bedroom mirrors my advice to a gay guy attracted to degrading “antigay” gay porn: “A person can safely explore degrading fantasies—even fantasies rooted in ‘hate ideologies’—so long as he/she is capable of compartmentalizing this stuff. Basically, you have to build a fire wall between your fantasies and your self-esteem. (And between your fantasies and your politics.)”
If you can build a fire wall between their fantasies and your politics and beliefs, IMPERIALISM, go for it. If you can’t, don’t. —Dan