How to Approach the Sensitive Question: Anal?

Gentlemen, this is a problem so many of us have experienced: How to ask a young lady if she likes it in the pooper. From my personal experience, if you simply ask your date (particularly if it's a first date), you're most likely going to be met with, at best, nervous giggles, and at worst, a steely gaze followed by a request to be let off the back of your bicycle.

Why is this? I believe it's because "society" frowns upon this form of intercourse, even though 9 out of 10 women prefer it. (Like most other facts in my book, I just made that up.) Why do I put "society" in quotation marks? Because what is "society?" It's you and me, and the only way we are going to change "society" is by taking an active role in dispensing with the embarrassment and shame of putting your wiener in some chick's butt.

How do we do this? As loving men, how do we approach the sensitive question: Anal?

There are a couple of different methods. The most common is what I call "the accidental method." Simply put, you wait until you are about to have intercourse. Then, you "accidentally" put it in her rear end. When she says, "That's the wrong hole," you say, "There's nothing wrong about it." From that point, it should be obvious how she wants you to proceed.

I don't recommend this approach because it catches the lady off guard and, if for some reason, she does not want to proceed in the prescribed manner, it necessitates you either cleaning yourself off or "double dipping," which is not a good idea for hygienic reasons.

Another approach is the "finger twaddle." I call it that because "twaddle" is a very funny word. This is a multi-stage process. First, during foreplay, spend some time fondling her tush. If she responds positively, insert your pointer finger, a maneuver I call "the twaddle." Twaddle around in there a little. She likey? Great. Now, as you twaddle, whisper the following in her ear. "Roll over, baby." The rest should take care of itself.

Maybe you're one of those guys who likes to lay down the rules of the road before the evening progresses to coitus. As I mentioned before, simply posing the question in a straightforward manner rarely achieves the desired result. Instead, try asking in an indirect way.

Perhaps you've just enjoyed a romantic dinner together (I suggest Red Lobster). The evening is going well, and you suspect the two of you might end up in bed together later in the evening. Great. Here's what you do: Order dessert. (If you take my suggestion of Red Lobster, I further suggest "The Chocolate Wave.") When your Chocolate Wave arrives, spoon some of that gooey concoction into her mouth, and say, "I wish this gooey concoction was my wang, and I wish your mouth was your butt." If she says, "I wish that, too," you'll know where you stand. If she says, "That's disgusting," you can easily say, "I was just kidding." Or, less convincingly, you could try, "I think you misunderstood me." But that's not the kind of thing that's easily misunderstood.

If this is still too direct, take her on a long walk through a nature conservancy or arboretum. While strolling among the flora and fauna, take her hand in yours and say something like, "I'm having a great time. I'd like to know everything about you." Women love to hear that. Next, ask her a series of utterly meaningless questions: "What are your hopes and dreams?" "Have you ever been in love?" "What's the worst tragedy that's ever befallen you?" Etc., etc. As you are "listening," slowly wrap your arm around her waist, and slide your hand down to the small of her back. Continue talking until you decide the moment is right for an "over-the-pant finger twaddle." This is accomplished by lightly caressing her anus in a "sympathetic manner." How do you caress somebody's anus sympathetically? Brother, if I have to tell you that, you need more help than I can offer.

Another tactic I have found helpful in the past is the tried and true, "I have a friend who ... " scenario. The way this works is pretty self-explanatory. While talking, mention that you have a friend who would like to fuck her in the ass. If she asks who, say "You don't know him," then quickly follow up with, "Isn't that so funny?" If she says anything other than, "That's disgusting," then I think you can safely assume that she will respond positively to those three magic words, "Roll over, baby."

As you can see, there is no one way to deal with this perpetually vexing situation. Instead, try a variety of the techniques outlined above. Trust your intuition. And if, by chance, you find yourself with a woman who doesn't like it in the rear, don't despair. While anal sex is an important consideration when considering a mate, it's important to remember that it's not the only consideration. Remember, over time, even the tightest tush will wear out, but a warm heart never will.

*I confined this essay to the heterosexual community, as I don't know the protocols for the other half, although I suspect the conversation usually goes something like this:
"Wanna ass fuck?"
"Yes, I do."

Michael has a book coming out featuring this essay, and 49 more that are equally funny and far less freely available on the internet. It's called My Custom Van: And 50 Other Mind-Blowing Essays that Will Blow Your Mind All Over Your Face and you can order a copy here.

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