I’m a straight woman and I’ve been with my boyfriend for four years. The sex is great, but we recently began to experiment with anal. He enjoys it, he takes his time and warms/lubes me up, but it is still painful. I don’t let on because I know how much he gets off. Any tips for a beginner? —Silently Whimpering
Smoke pot, SW. Don’t break any laws, of course, but if you’re using lots of lube, if he’s going very, very, very slowly at the start, and if you’ve read Tristan Taormino’s The Ultimate Guide to Anal Sex for Women (twice), you might want to smoke a little bit of pot—just a little bit—before you give it another go.
And pot or no pot, SW, you MUST tell your boyfriend that, whatever he’s doing back there, it’s not working for you. THAT’S AN ORDER. Read or reread Taormino’s book, and then try some other positions, more or different lube, longer warm-up sessions, anal-play sessions without any expectations of penetration, and, of course, a consciousness-raising session that involves you doing the boyfriend’s ass with a dildo that’s roughly the same size as his dick.
I’ve been reading your column for a few months, Dan, and I’m wondering a few things. What are your academic credentials (if any) that qualify you as some kind of sexpert? I suspect you have none. Are you a guy or a girl? Judging by the bias of your answers, my guess is that you’re a woman. Are you straight, gay, or bi? Single, married, or divorced? I’m sure your readers would love to know the answers to all of these questions. However, I suspect you haven’t got the balls to print this letter. —Chaz The Spaz
P.S.: The Playboy Advisor replies to ALL questions submitted (even those he doesn’t print). Do you?
Look up “advice” in the dictionary, CTS, and it says, “opinion about what could or should be done.” The only qualification you need to offer someone your opinion, of course, is having been asked for it. As my mail comes addressed to me, I am uniquely qualified to offer advice in this space.
Look my ass up on Google, CTS, and it says that I’m a fag. I’ve been with the same guy for 13-plus years, we’re husbands in Canada, boyfriends in the United States, and our young son’s loving parents wherever the fuck we go. I have never claimed to be a “sexpert,” whatever that is, and while I do not doubt that the Playboy Advisor is a better man than I in every respect, the volume of mail I get prevents me from answering everyone personally.
I am a 23-year-old female whose boyfriend has a piss fetish. By this I mean that he enjoys it when I urinate into his mouth. While this is not something I find erotic, I have no issue with indulging him. My only problem with it is that I don’t like to kiss him afterward because of the taste. I can’t stand it. Is there a tactful way to ask him to brush his teeth afterward without COMPLETELY ruining the mood? Thank you very much for your help. —Embarrassed Non-Urine Fan
Seeing as there’s no tactful way to ask someone to piss in your mouth, ENUF, you’re under no obligation to be tactful about asking your boyfriend to brush his damn teeth. Saying, “Go brush your damn teeth, piss-boy, and you better be back here before I decide to eat asparagus at every meal for the rest of my fucking life,” in a low and sexy voice should not only do the trick, it will ensure that his dick is still hard when he gets back.
Hey, everybody: Thank you so much for all the thoughtful condolence e-mails after the death of my mother. Your good wishes, to say nothing of the many pictures of your boyfriends’ butts, lifted my spirits. My tickets to the Friday night performance of The Drowsy Chaperone in Chicago—they were supposed to be mother’s birthday present—wound up going to a lovely and very deserving mom. And I got to see the show, too—thanks to Ted at Broadway in Chicago—at Sunday’s matinee.