Originally published January 28, 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. However, his girlfriend doesn't know he's bisexual, and I'd feel uncomfortable having sex with him behind her back. 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

My response after the jump...

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.