Anal Over Here, Anal Over There (Anal, Anal, Anal Everywhere)

Q. I’m a BBW, how can I fully enjoy and get into anal sex? I’m 47 and have never done this. [NSFW images after the cut]

1892 lithograph by Paul Avril depicting the obvious. Everyone looks like they are having a pretty good time. Image courtesy of Wikipedia.

A. First time for everything! First off, I want congratulate you, BBW, on taking this exciting new leap into the unknown. Anal sex can be an awesomely pleasurable experience for both you and your partner, and with a little practice, you can easily become a pro. Whether you’re interested in straight up anal, pegging, anilingus, fingering, or toy insertion, we are here to offer a few tricks of the trade to keep your butthole in good shape.

First off, a word to the wise: anal sex is considered a high-risk sexual activity, due to the extra vulnerable state of the anal and rectal tissues. Your butt is a sensitive place! Think of it not as some Mission: Impossible danger situation, but just as delicate grounds. Not only is the tissue in the surrounding area more likely to tear than, say, vaginal tissue, there really isn’t any natural self-lubrication, which, depending on your activity level, can cause minor to major tears. This can all be avoided with some proper maneuvering, but I always like to emphasize safe sex, especially of the anal variety. Clean your toys, use a condom or a dental dam, get tested, and make sure to, as the good doctor says, do no harm (play it safe, kittens).

So as far as the getting the technical logistics, there is no one way to go about your journey in anal sex. Some folks begin with fingers or toys, some folks dive in with a full-on dick or strap-on; it’s all up to you and what you are comfortable with. Having a conversation about what you want to try and how slowly or quickly you want to move is a way to set terms. This way, you can always discuss having a safe word if shit gets too real, too quick (“banana cream pie,” I find, is a marvelous safe word). You can also talk about the messier aspects of anal sex, because yes my friend, anal sex does get messy. From potential runny farts, to flappy farts, to full-on out-of-control bowel emptying, knowing these things beforehand can cut down on the potential awkwardness that may be a full-on flappy butt fart. That’s what happens when you stick shit in your ass!

As far as getting to the actual deed goes, ask yourself, am I feeling it? Is my partner feeling it? There’s no reason to be doing what can potentially be an uncomfortable thing if you aren’t feeling it 100% at the time. If you are both turned on, there will be less resistance form your butt (talk about being a literal tight ass). Don’t go straight to the butt; fool around a bit, take your time, and get hot and bothered. This way, you will both be feeling a bit sexy and less likely to be bothered, both mentally and physically by say, an awkward moment. But! If you are fooling around, make sure that whatever goes in the butt, stays only for the butt. There is no quicker way to getting a nasty sort of infection than if you have a toy or a dick that has been in your ass, now going up your snatch. So if you want to play around via mouth or vagina as well, make sure to try and keep butt activity far enough from it.

Now, let’s talk lube. You’re gonna need it. And not just a little lube – you need a lotta lube. Water-based lube that is going to coat both whatever is going up your butt and yes, even around your butt.  Lube is your number one, anal sex having friend. Use it and use it generously. Seriously, there is never enough lube. Coating your hole in lube is actually putting you at an advantage here, mostly because it’s a little taste of what’s to come and it’s helping you out as far as getting anything into your butt. This is the time to just move slowly – think of it as stretching before exercising, a way to loosen up your butt. You can ask your partner to put a clean finger or two into your butt, and if you are feeling adventurous, even use a toy to help you put the lube on. If you do use toys, please remember the importance of a flared base! This shall save in the, let’s call it, awkward recovery department if that trip had to be made. Also, make sure your toys are non-porous, preferable silicon-based. Please also make sure they have been cleaned. Whether it’s butt plugs, vibrators, strap-ons, or dildos, taking the same amount of precaution you would as if it were a penis or a hand is most crucial.

Depiction of anal sex on 510 BC Attic red-figure kylix. Image courtesy of Wikipedia.

So lets say you have reached maximum impact and the object has landed within the butt. Groovy! Take it slow until you are at a pace you feel good with. Anal sex can go in between feeling good to feeling extremely uncomfortable, depending on how quickly you are moving or how long you are having it. Position also matters! Doggy style is said to be the most comfortable, but laying on your side with your partner behind you, or missionary style can be super comfy. Work with these to see which is best – depending on how you are situated, it can feel like way too much all at once, or just right.  When you find the way that works best, start playing around with everything else.

Once you feel like you have a grip on anal sex, I would suggest Pucker Up, the sex positive salon run by the amazing Tristan Taormino. Taormino is a renaissance woman, equal parts writer, activist, sex educator, and porn film director. I was first introduced to her through her weekly column in NYC’s The Villgae Voice, where the following resonated with me: “Our asses carry with them so much cultural baggage”¦ Most of us are taught at a young age that our butts are dirty, that they shouldn’t be shared with others, that they are not a source of pleasure – all of which aren’t true.”

Pucker Up offers more specific advice for anal play (like what to do about post sex “runs,” anal fisting, different toys,  and so much more) once you have gotten the swing of things. However, I also recommend her book, The Ultimate Guide to Anal Sex for Women, as a great starting place if you are new to butt fun. Part self-help and how-to manual, and part history, the book is super accessible, as well as up front about safety, preparation, hygiene, and communication. While most tips on having good anal sex float around the Internet like white on rice, Taormino is an expert on all things anal and her words of wisdom can apply to almost any situation.

Before we part, there is more one thing I want to point out. Even with these tips or someone else’s, remember, you don’t have to like anal sex. It is awesome you want to give it a whirl and I am excited for your quest for anal pleasure, but if all goes the way it does and you still aren’t feeling it, cut your losses and focus on the stuff that does make you feel good. Or try other things if you are feeling adventurous. While anal sex can be really awesome, it also doesn’t have to be something you have to whip out in your sexy time cards, like some poker chip. Do what feels good for you – ain’t nothing more to it than that.

Until then, happy anal sexing, BBW !  Make your journey be pleasurable and please – do let us know how your adventure goes.


Got a ques­tion to ask, subject you’d like us to dis­cuss, or myth you’d like us to bust? Keep “˜em com­ing! (Lord.Have.And.Mercy.) You can send us an anony­mous mes­sage via the Ask Us! fea­ture here. We promise we don’t bite (unless you’re into that type of thing”¦).

2 replies on “Anal Over Here, Anal Over There (Anal, Anal, Anal Everywhere)”

My two cents, also serious TMI/you are about to know much you may not have wanted to about me warning:

Preferred anal lube: Ride H2O aka Dude Lube by Sliquid. Its a thicker water based lube (yes, silicone is better for anal but for sensitive ladies this is a quality long lasting, glycerin free lube that does the job).

Preparation: some days you are just not feeling it. Those are the gurgly angry stomach, my shits have been a walk through hell days. Good days are the ones with no indigestion, and you just took a huge colon cleansing dump that left minimal particles behind in your rectum. I have a douche I use for squeamish partners just to make sure the area is fully cleared out (after douching wait a minimum of two hours before engaging in any play though). I also have a series of butt plugs that range in 3/.4″  to 2.5″ diameter (depending on what we’re going for that evening) to help myself stretch out and relax a bit on my own time which I think is important because I’ve been known to be the impatient one who rips myself open not wanting to take the time to go slowly.

As far as play goes, I prefer to start with PinV or oral while using toys to further stretch and relax the area. I actually prefer double penetration with vibrating toys than full on anal sex. Then as soon as I’m ready, I work the guy/toy in myself at my own pace and proceed to go wild. Anal sex isn’t something I do for extended periods of time, so it’s usually a grand finale, though anal play I can handle for a whole session.

Is it just me or is ‘safe word’ the best safe word ever?  Why would you ever say ‘safe word’ unless you were using it as a safe word? My ex disagreed with me saying it was too unoriginal but considering we only needed it during tickle fights (we’re a bit tame…) it wasn’t a huge deal.  But I still think there is no better safe word.

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