My best friend and I are both married (to women) and have families. We admitted to each other a few years ago how frequently we still masturbate and love to watch gay porn. We have managed to get together alone a few times to play out our gay fantasies with each other, which has been great. We jack each other off, do a lot of frottage, and suck each other to completion, I want to go further and have asked if we could rim and fuck but he doesn't want to do anything anal. I'd be happy to rim him and for him to do me if that would make it easier for him. But he says while he hates to disappoint me, he just can't do it. I've offered to make sure I'm really clean and told him he could wear a condom but still no luck. I know not all men who have sex with other men do anal for various reasons, but I still feel it would be the ultimate in our intimacy together if we at least tried it. Any suggestions on convincing my buddy?

Clear Anal Needs Affront Lover

P.S. If we both took a sexuality spectrum test he would come out bisexual and I would be definitely homosexual, so maybe that has something to do with it?

You asked, he said no. You might not like his answer, it might not be the answer you hoped to get, but it's the answer you got. He said no to rimming and/or being rimmed, CANAL, and he said no to fucking your ass and/or having his ass fucked. Spotless after douching or take your chances after curry, condom or no condom, your fuckbuddy said no. And you're just going to have to accept that, CANAL, because no means no means no means no.

I should probably stop right there. If this was a live show—and, hey, we've got some live shows coming up—that would've earned me a nice little round of applause... which would've provided me with just enough time to contemplate leaving it at that... but sex and desire are more complicated than applause lines... and I'm constitutionally incapable of leaving anything at that... so here we go...

There are lots of people out there who initially said no to anal/bondage/piss/whatever and who now happily engage in anal/bondage/piss/whatever. (Let's go with ABPW for short, shall we?) But you gotta trust me on this, CANAL: people who initially said no to ABPW and who now enjoy ABPW didn't give in to pressure. No one doing ABPW under duress and/or to avoid disappointing their partners ever truly comes to enjoy ABPW. (Certainly not with the partner who coerced them into trying it.) What these people all have in common is 1. their initial "no" was respected and 2. their lovers backed the fuck off.

Now sometimes a "no" to a sexual request a knee-jerk, sex-negative response.

BUT! BUT! BUT! Not only are we morally obligated to respect the initial "no," CANAL, even if we suspect it came from a knee-jerk, sex-negative place, it's in the kinkier partner's best interest to do so. ONCE MORE AND WITH FEELING: that initial "no" must be respected—and respecting the "no" means dropping the subject without pathologizing or vanilla-shaming or not-gay-enough'ing your partner. Because, hey, it's entirely possible their "no" isn't coming from a knee-jerk, sex-negative place; some folks are legit vanilla and/or not into anal and that's fine.

BUT! BUT! BUT! If that initial "no" did come from a knee-jerk, sex-negative place... well, here's what can happen: the less kinky partner, not feeling pressured to do anything that makes them uncomfortable, will think about ABPW. A seed was planted. And since the partner who's into ABPW doesn't have to pretend they aren't into it—they can watch ABPW porn—and since ABPW will sometimes come up on its own (on TV, in movies, in convos with friends), the seed will get replanted. Or watered or whatever. And if turns out the less kinky partner is actually more sexually adventurous than even they might've realized—if they're one of the millions of people who needed permission to even think about kinks—they'll gradually go from thinking, "ABPW is something my lover wants to do," to, "ABPW is something I might wanna do for my lover," to, "ABPW is something I wanna do for me." And that's when the partner who initially said "no" to ABPW will suddenly raise the subject. ("Hey, remember when you said you wanted to try ABPW? Well, I've been thinking about it and...")

BUT! BUT! BUT! Your lover might never get there. Some people just aren't into anal—or bondage or piss or whatever—so you'll just have to be zen about it, CANAL. Your lover knows you'd like to do anal. If it happens, it happens. If it doesn't, it doesn't. But if it does happen, CANAL, you want it top happen for the right reasons. You want it to happen because your partner wants to do it for you and for themselves too.

P.S. There are bi guys who are into anal and a lot of gay guys who aren't; where someone falls on the sexuality spectrum is neither relevant nor determinative where anal is concerned.

P.P.S. I realize anal isn't all that kinky, particularly for queer men; I lumped it in with actual kinks like bondage and piss and whatever for sake of argument.

P.P.P.S. I didn't get into the fact that CANAL and his lover are cheating on their wives. I leave that to you, commenters.