
Recently, I received an e-mail of, ahem, a personal nature. A friend and her boyfriend were planning on having anal sex for the first time, and she needed some down-and-dirty lady advice.

I was both honored and delighted by her request. Am I an expert? I mean, I'm no doctor. But I am an enthusiast, and that, friends, makes all the difference.


A couple notes/disclaimers to start:

My advice-seeking friend is a lady who likes dudes, so in the original e-mail, I use boy/girl language not out of heterocentrism, but out of situational specificity. That said, I'm pretty sure the principles listed below apply to dicks and dildos alike. So to queer things up a bit, any time you read a word like "dude" or "cock," please replace it with whichever epithet or insertable object applies to you!

Speaking of insertables! As someone who has engaged in pegging, I have one piece of advice for first timers: BEWARE OF GIANT, PORN-SIZED DILDOS. They might look shiny and enticing in the store, but their luster will fade in the bedroom. Trust me. My ex and I learned that one the hard way. In other words, your first car should not be a Cadillac; a sensible midsize or cute compact will do you just fine. (Incidentally, my first car was a Cadillac—my great-grandmother's. It clearly effed up my entire sense of proportion.)

Truth: Anal isn't for everyone. If you try it (following the guidelines below, natch) and hate it, you never have to do it again. That is my solemn vow.

Now without further ado, humble advice from one lady to another. And hey, if it's your first time, or if you want to rekindle an old flame, or if you're just sorta intrigued by the whole thing, congratulations! Curiosity is the first step on the road to satisfaction.

Dear A.,

Let's get right down to it, shall we? Butt sex. AKA, nature's birth control. AKA, awesome if done correctly. AKA, I'm so happy for you!


Here's how I like to roll when I'm doin' it. (I'm sure there are other ways, but this is what works for me and my booty.)

1. Make time. LOTS of time. You don't want to feel even remotely rushed, so give yourself like a 3-hour window (especially the first time). Or just do it at night before bed!


2. Washin' up. I prefer to shower beforehand, just to make sure everything's cleaned up down there. I mean, impeccable hygiene or no, some amount of fecal matter is inevitably floating around at any given moment, but a good scrub can't hurt. Also, if you know you're fresh, you're more likely to relax during the deed.

3. The joy of rimming. Boy, do I love a good rim job. Hopefully, you and your b/f do too. 'Cause like, if boy can't get a tongue in your butt, ain't no way his dick's going up there, youfeelme? SO. Duder needs to spend a good long time eating and massaging your tush to get you relaxed and aroused. [Note: If you wanna reciprocate, that's fun too. Anal 69 is an option. Or just taking turns. In the immortal words of High School Musical, "We're all in this together."]


4. LUBE. USE IT. LIBERALLY. I CANNOT STRESS THIS ENOUGH. (KY is both totally effective and totally cheap! Oh, and the CVS knock-off works like a charm.)

5. Fingers. Dude should start with one. Then two. Then maybe a vibe or other toy, something smooth and phallic is always nice. (Something Smooth and Phallic is also the name of my indie band.) Meanwhile, don't forget that lube.


6. Dick time. Start with the tip. And JUST THE TIP. A friend of a friend's boyfriend just shoved the whole muhfucker in there, and the lady PASSED OUT. So don't let your boy make the same mistake that guy did. So anyway, get the tip in there and just let your ole sphincter get used to it. Again: you have all the time in the world. When you're ready, dude can start going deeper, but SLOWNESS IS KEY. As the Bible says, "love is patient." And keep that lube comin'!

7. So eventually he'll get the whole D in there (probably*). At that point, you'll be good and relaxed, and he can start the good old-fashioned ass fucking. If it hurts, you're not relaxed enough, and you should go back to step 6 (or 5, or 3, depending). Also, say it with me now, don't be stingy with the lube!


*Sometimes cocks feel too big, or butts feel too tense, or (most likely) a combination thereof. Even the most enthusiastic and patient among us will run into these perfectly normal complications. Point is: if you don't have Full-Fledged Anal Sex the first time, whatevs! Don't force it; there's so much more to do with the caboose than just peen-in-ane.

8. Clean up. Probs not a great idea to put a poopy wiener in your vadge or mouth. I mean, some people get off on that and are willing to take the risk, and that's cool. But if you're not one of those people, have your dude clean his junk before he does anything else with it.


9. Gettin' off. Personally, I've never come during anal sex. I suspect that's because I don't have a prostate. IRREGARDLESS. One of the reasons I'm a fan of A.S. is that it gets me SUPER aroused. So post-anal oral is always a LOT of fun. And the Shocker? Once your pink and your stink are both ready for action, that shit is awesome.

10. Odds and ends. (Ends, get it?)

Getting poo smell off fingers (and wien). If soap doesn't work, toothpaste will do the trick.

Y'all read Savage Love, right? Santorum

It is a fact that your butt might feel weird, and you might have some not-so-solid poops for a few hours after.


I think that's all. Oh wait. One more thing:

11. HAVE FUN. Because you're worth it.

Lady advice! Fuck yeah!

Good night and good luck,

Diana

Update: Condoms, condoms, condoms. Even if you and your partner have been tested, they make it less messy. Also, "nature's birth control" is a light-hearted quip. It is theoretically possible to get pregnant from anal sex if ejaculate gets in the right place by accident.


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