January 27, 2010

I’m a single (mostly) gay guy who is curious about women. A hot bisexual mate is interested in a friends-with-benefits arrangement. I’m not looking for an LTR just now, so regular, no-strings sex sounds great. However, his girlfriend doesn’t know he’s bisexual, and I’d feel uncomfortable having sex with him behind her back. I’ve said no to guys in the past, bi and gay, because they wanted to go behind their partners’ backs. My mate would like his girlfriend to know about him because he’d really like to have threesomes with her (something I’m up for), but he’s worried about how she’ll react.

Personally, I’d be more concerned about how she might react if she found out about his sexuality some other way. That’s one reason why I always err on the side of honesty. However, I’m not exactly unbiased: I’d prefer threesomes to dicks-only sessions. What should I do?
Horny Homo

How about a little honesty mixed with a little dishonesty?

Your mate should offer his girlfriend the boy-girl-boy threesome that all of today’s modern young women fantasize about. (Blame Twilight—why can’t Bella have it all?) If your mate is worried that she’ll react negatively to the suggestion, he can open by telling her that what he’s about to propose was all your idea. She’ll want to know if his gay-but-bi-curious mate—that’s you—is going to want to get into his presumed-to-be-straight pants. Your mate should shrug and say, “Maybe…” and depending on the look on her face when the possibility of Edward-on-Jacob action is raised—disgusted or intrigued?—end with either “…but I don’t think I’m interested in going there” (leaving open the possibility of “getting carried away” and “going there” during the threesome) or “…and I might go there if that would turn you on” (making any boy-on-boy action at the threesome something he did for her).

If the threesome is a success and you two wind up playing with and in front of her, HH, your mate can come to the sudden and shocking realization that he’s bisexual. This will hopefully lead to future threesomes and, perhaps, at some point, her blessing for some boys-only time. If she objects, HH, your mate can blame her for “making” him bisexual—or making him realize it—because he fell on your sword that first time because it was what she wanted.

Do you think he is bisexual or bi-curious? We intend to enact this fantasy, and I wonder if it could shift the dynamic of our relationship.
Threesome Curious

It can be hard to predict whether a man will have an epiphany during an m-m-f threesome and come to the sudden and shocking realization that he’s bisexual. (Um… does your boyfriend refer to his male friends as “mate,” by any chance? Is he a fan of the Twilight series?) He’s obviously more aroused by male-male contact than he’s capable of admitting when he isn’t about to blow a load, TC. This fantasy of his isn’t about, or isn’t just about, wanting to gangbang a girl with a buddy. Your boyfriend wants to bump penises with another dude—but with your, um, lady “innards” providing the “no homo” absolution.

But I don’t think you need to extract a full confession of bi-curiousness or even heteroflexibility before you realize this fantasy. He may not be in denial about what his desires add up to, TC. He just may want to check his fantasies about male-male contact against the reality of male-male contact before he tells you what he suspects: He’s the tiniest bit bisexual.

Your uncle is hitting on you, UNCLE, in his fashion—that is, the fashion of the tormented, self-hating, conservative/religious closet case. If you don’t wanna find yourself standing there with your uncle’s tongue stuffed in your mouth someday—you’d be surprised how quickly someone can stuff his tongue in your mouth—I would advise you not to spend another moment alone with your asshole uncle. And, yes, tell your parents what he’s been doing. Because, UNCLE, if he ever makes a pass at you and a scene ensues—you scream, you yell, you bite his tongue off and spit it out the window—your uncle is going to insist that you made the pass at him.

I am not questioning my sexuality, I’m not “bi,” I have zero desire to date women. But my boyfriend immediately accused me of having issues with my sexuality, and after a two-week fight, I dropped it. Fast-forward to just before Christmas: I received a promotion, moved to a new floor, and have my own office now—and one of my new female coworkers has been coming on to me. First problem: She’s married, so that would be crossing a line. Second, we’re coworkers, and she has even more to lose than I do.

Is there some other way—I already tried the direct approach—to bring this fantasy up to my boyfriend again, or should I just let it go?
Flirting With Danger

I’m shocked that your boyfriend—a man who’s willing to share his boyfriend’s ass with other men—would react so violently to your curiosity about lady innards. But seeing as the direct approach prompted a two-week-long fight, FWD, I can’t imagine you would have much more success with the indirect approach. (I can’t imagine what the indirect approach would be.)

Since you’re not strictly monogamous and the boyfriend’s not strictly rational about this, FWD, a case could be made for satisfying your lady-innards curiosity on the sly and filing the affair under “what he doesn’t know won’t hurt him.” But I can’t think of a worse set of lady-innards to satisfy your curiosity with than this woman’s. You could wind up losing your job and your boyfriend if the affair got ugly and got out.

Wait, FWD, wait. In time, some other gay-outards-curious lady will come along, and perhaps by then, your boyfriend will have come around.