QUESTION: “When is it okay for a lady to go for the proverbial gold and try to pleasure your prostate?  Should we talk about it first or just do it in the heat of the moment?” 


Frank LeBaron: There are two answers to this question, one if you are a man’s Ms. Right, the other if you’re Ms. Right Now.

To Ms. Right I would counsel you to be gentle, tactful and ONLY pull this move if your man has done the same to you in the past. Call it a double standard, call it chauvinistic, but pulling a shocker without provocation can lead to bad relationship results. Know your man, and please, please, please, please be gentle.

To Ms. Right Now, you obviously are down with the brown, or something like that. You’re probably a little on the freak side to begin with, so go for it. Dead fish need not apply, but if you’re a minx and you know it go for the glory (hole). Don’t worry, the surprise in his eyes will turn to a grin in no time. Think twice about it though if you just got your nails did. 

The Doctor: You don’t need an MD to know that this is a delicate maneuver.  But do you really want to have a sit-down talk about peeking around down there?  I guess it would depend on the type of relationship you’re in, but I offer a more consequence-free alternative.

I propose you and your man get sauced and in the heat of the moment play a little Dora the Explorer.  There’s a fine line between success and failure and you’ll know very quickly whether or not you’ve struck gold.  Note, even though some guys may enjoy this technique, not all of them will be willing to talk about it openly or admit to wanting a repeat performance.  And in the case that your move backfires, at least you have the Drunk Card to play.

Like the great Homer Simpson once said:  “Alcohol, the cause of and solution to all of life’s problems.”  In the world of anal exploration or otherwise, truer words have never been said. 

Jensen: When is it okay for me to stick my finger up your ass? I’m guessing you don’t have a fixed answer (i.e. “2nd date”) — and that’s okay, cause neither do guys. Whose ass do you want your hands in anyway? Boyfriend? Fling? Random one-nighter? These are pertinent questions because each of these personalities might respond differently. If you do it to your boyfriend randomly one night as you’re blowing him, he might appreciate your anal irreverence. But if you do it to your fling and he doesn’t dig, you run the risk of being known as the girl who takes the same liberties as a proctologist. But then, there’s always the flip-side: the guy might love it and you’ve just opened a whirlwind of sexual idiosyncrasies, anatomical nihilism, and bodily hedonism.

So, get drunk one night, start it lightly, see his reaction, and go from there. 

Al Batrosse: If you have to ask, his ass may not be up for grabs. When it comes to the bum a lot of straight guys like to give but they don’t like to get.  Sex is so sexist sometimes. There is one surefire way to please and it is many ways the El Dorado of male sex fantasy life . . . In other words, a rim job, is that out of the question? One good turn will most definitely lead to another. 

Valmont: This ranks right up there with enjoying Sex and the City and wearing pink (it’s not pink, it’s SALMON!) in the vast and wholly irrational pantheon of “Things Many Straight Guys Fear Will Make Them Look Gay”. Chalk it up to having our peers delineate acceptable behaviour by the ubiquitous use of the phrase “that’s so gay” since sometime around the second grade.  So lets talk worst-case scenario. Suggest it outside of a sexual situation and he might get red in the face and storm off all embarrassed because he thinks you’re trying to trick him into admitting that he likes dick. On the other hand, going all the way on the first try with no build-up might lead to more shock than awe. So how bout this: you know how there’s always some crap about applying pressure to the perineum in the sex tips sections of magazines? That’s utter bullshit. Feels like the girl’s hand got lost. It’s just code for touch his ass. Do it gently and then follow up with a) an affirmation that you like doing it (whether you actually do or couldn’t care less is irrelevant), and then b) ask him if he likes it. In that order. 

If you have a question for the Guys Talk forum feel free to send it to, it’s as anonymous as glory holes.

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