Around Christmas, my male best friend from college and I decided to try to take our friendship of five years to the "next level." Shortly after we started having sex, he told me that he had lost his virginity at age 13 to a guy (and didn't date anyone else until he was 21). That relationship was with a girl and he was in a LTR with another girl after that. He shared with me lots of fantasies involving men (and humiliation), compared my blowjob-giving techniques to his own, has a plethora of anal toys and still keeps in touch with the guy he lost his virginity to. All the while he insists he isn't bi—being with guys is just a "kink" of his. The other side of all this is his love of BDSM. He prefers to be very submissive and has me tie him up, use whips and crops, and control how often and when he can masturbate. The key themes in his fantasies are definitely being used, humiliation, and anal play.

All of this is well and good and I consider myself to be very GGG. I've jumped into the BDSM with interest and enthusiasm and have tried to indulge and even arrange his fantasies with men. Despite all this, I still can't seem to make him happy. He's an overall very negative person, is diagnosed with depression and an anxiety disorder and it seems like I just can't do enough to please him (even though I never thought I would have a dominatrix outfit, weild a whip so professionally, or so happily play with a guy's butt). With all of these factors combined, I can't help but wonder if he is completely denying he is gay. The field he is in would in no way be accepting of an openly gay man and he is very passionate about his work. But he has three immediate family members who are gay. I'm worried that he's in denial and is never going to be happy, in a healthy relationship, or content unless he accepts this about himself. I'd rather have a happy, openly-gay friend than a confused and seemingly un-pleasable friend-with-benefits. How should I deal with this?

Friend With Benefits Beard

My response after the jump...

Gay or straight—does it matter?

Unless you're having a good time exploring this shit with him, FWBB, you should stop seeing/indulging/putting up with his shit because he's proven himself to be a thoroughly unpleasant, messy ingrate. He may be gay, he may be bi, he may be into same-sex-play as a humiliation/domination thing, or be into it as excuse, and he may be from outer space. But yuo know for sure that he's an asshole. DTMFA.

But hang on to that outfit—and the whips, if they gifts—because there are lots of guys into BDSM out there, most of them 100% straight, and most of them are very nice and appreciative when they encounter an indulgent, GGG girl with a flair for BDSM.