Dear Hardy Brothers,

My gf and I have gr8 sex, but I want to try new things, especially anal. I’m scared to ask because I think she’ll say no. Should I just try to sneak it in?

Yours,

Dangerously Curious (via text message)

Joe: Let me say first that while I appreciate your Hardy impulses, D.C., you should never sneak anything in, anywhere. Not only does sneaking it in constitute rape, but it would also mean the almost certain end to your relationship—which seems to be a promising platform for you to explore the final frontier.

For men that have sex with women, anal sex has become, like threesomes, a mythical beast just waiting to be conquered—and for good reason (for men that have sex with men, anal sex has largely become the equivalent of “regular” vaginal sex, and is therefore not as exciting as the holy grail you seek). The stakes for your partner, however, are exceedingly high. If performed incorrectly, anal sex can leave your partner permanently damaged, with pustule hemorrhoids, even incontinence. That’s right D.C.: stick it in there with reckless abandon, and your partner may literally shit on you, uncontrollably, forever.

But, having hopefully offered a sufficient disclaimer, anal sex can be a supremely intimate and lustfully hot way for you to have sex. Believe us. We’ve enjoyed it a whole ¼ of a time.

To initiate the conversation, don’t put all your cards on the table at once. Instead, begin by asking if she would be interested in lighter ass-play. Fingering is an ideal alternative to the high-stakes exchange that Dan Savage prescribed at least once for this very situation: whereas he suggests that you let your woman peg you (penetrate you with a strap-on), before you have anal sex with her, we merely ask that you let her lightly poke your insides first. She will feel that your sexperimentation is not selfishly one-sided, and you will have the benefit of more explosive, anally stimulated orgasms.

You must know, though, that you should never be afraid to ask your partner anything. So long as you’re open, honest, and respectful, your relationship shouldn’t be shitty.

Frank: Joe, Joe—please, calm down. You’ll scare the poor boy away! While he may be rustic enough to think that even if he gets through the back door to enter into some non(explicitly)consensual anal, he won’t be “sneaking” it past anyone. She’s gonna fucking know.

Listen to me, D.C. Unless you’re really, really wrong about your girlfriend and she’s just been dying to give you the ass (there’s probably less than a 0.01% chance that your GF or anyone else will withhold this information from you if they’re DFA), it brings a smile to my face to imagine the ensuing conversation you two will have, coitus interruptus and all.

I realize it probably doesn’t bring much of a smile to your face, though, D.C. If you start thinking about all the disaster scenarios Joe described too, it might just put you off the ass forever, and from what I’ve read, this might be the most tragic disaster of all.

You should heed Joe’s warning, but also know that performing anal safely isn’t difficult. More detailed explanations of proper techniques and equipment are amply available elsewhere, but for our purposes, you probably all know the drill: condoms; lube; proceeding slowly; making sure both partners, especially the one being penetrated, are relaxed; stopping if it’s uncomfortable or painful for either partner; and finally, better to skip it that week if hemorrhoids or other sores or lesions are in evidence, etc. etc.

On the hilarious Showtime show “Californication,” the character Marcy gives her best friend the following advice on her wedding day after asking whether the friend’s soon-to-be spouse has “requested the ass” yet:

“You don’t deny your man the ass,” she exclaims emphatically. “You give it to him! Because once he knows he can have that, he ain’t gonna want that shit anymore. Believe that…the ass is always greener.” Marcy perfectly and accurately describes in action the mythical anal beast Joe mentioned earlier —never mind the fact that she’s stoned in that scene.

So. Bearing all this in mind, before you pop the question, D.C., you might want to make sure that you’re as enthusiastic about the ass as you think you are. Many obstacles await on the path to anal bliss—just ask Morrissey. It’s true you certainly don’t have to spend the rest of your life with the decision, or the ass, but they’re sure gonna spend the rest of its life with you. Penetrate wisely.

—xo xo The Hardy Brothers