So I got a request from a nice man on fetlife asking me for advice pertaining to pegging. I probably know very little about this compared to Tristan Taormino (the great ass sexpert), but I figured what the hell, I’d throw in my two cents on the matter.

For the uninitiated, Dan Savage popularized the label “pegging” to refer to women fucking men in the ass with strap-ons. However, just as intercourse should never be the be-all end-all of classic heterosexual penetrative sex, there is more to pegging than just strap-ons. For convenience, I’m going to use the term generically here to refer to any anal play done by women to men.

I’m going to tackle this issue in three parts. The first is how to introduce pegging into a sexual repertoire with a partner. The second is the tools of the trade that help for good pegging. And the third is the power-play and fantasy dimension that usually accompanies good pegging.

My now-husband started slowly introducing the idea of pegging into our relationship years before we ever did anything about it. He began by discussing it with me in a context where we were talking about deep dark fantasies (for anyone reading this blog, this strategy is an excellent one to begin confessing your own deep dark fantasies—ask for your partner’s). I was initially pretty skeptical, but he began educating me about the prostate, which if you don’t know, is basically the male G-spot, and can be stimulated indirectly externally behind the testicles, or directly internally in the anus. Hypothetically, men can orgasm just from prostate stimulation, although I confess I’ve never actually managed to pull that one off. For the gents reading this, don’t be discouraged if, upon revealing your pegging fantasy, your lady doesn’t instantly react with, “Why that’s always what I’ve wanted to do!” It may take some warming-up-to. Be warned that I haven’t encountered any subby girls who are really into pegging {although I assume they exist). Ladies, if you’re the one doing the introduction, make sure to tell your man about the prostate, and if he still looks skeptical, try offering to let him fuck you in the ass.

It can take a lot of experimenting to get good at it, though, because high-quality pegging requires an investment in high-quality equipment. The first thing I think is essential is a basic enema kit. Not the kind where you actually use a laxative—just use plain old water until the water comes back clean. If you’re usually clean, well, you probably don’t need an enema, but find out before you try to have sex the first time.  Asses are tricky like that, and everybody’s are messy sometimes, it seems. The second is good lube. I can’t stress this one enough: buy silicone-based lube (Pjur products are particularly good) and pay no heed to the price tag, because it’s worth every costly penny. But be careful, because your glorious silicone lube can damage your next essential tool, which is your handy silicone dildo. Cheap dildos suck and are even sometimes dangerous. Shell out the cash. It’s for your sex life—it’s worth it. I think the best dildos are VixSkin dildos, made by Vixen creations. But if you’re going to use silicone lube with silicone toys, you need to put a condom on your toy. If you despise condoms, then use a water-based lube that’s designed for anal penetration: I recommend Maximus, but it’s not anywhere near as good. Alternatively, you can use glass toys, but they’re pretty intense, and they’re not really good for beginners. Then your lady probably needs a harness to hold the strap-on unless she’s just going to hold it in her hand (which really isn’t a bad idea when you’re just starting out). There are many harnesses out there, and the cheap ones tend to be based on a thong design which I find intolerable. The designs have improved a lot in the last couple of years, and you can get some cool shit at Babeland if you’ve got the money. If you’re cheap and/or have a rope fetish, you can also just tie your own.  And last, but not least, buy some basic vinyl gloves. If you’re like me and hate latex gloves, non-latex gloves still work great. Some women don’t mind sticking their bare hands up boys’ asses, but she never knows until she tries how she’s going to feel about it, so it pays to be cautious.

So you’ve got a clean ass, some great lube, some gloves, and some really pricy new toys. Now what? The answer is up to you and your partners’ imaginations. For many (most?) men who want it, pegging is a submissive fantasy, and they really want to be dommed by their partners. It takes some experimentation to find out just how far that domming can go (How many fingers can he take? How big a dildo can he take? Don’t you want to know?). Boys, be aware that it’s not a coincidence that most women I know who are into pegging are Queer: they often enjoy the gender-bending that comes with strap-on fucking a man, and the sensation of fingering a guy’s ass is somewhat similar to another one of their favorite sexual activities… Conversely, some guys are into pegging as a heteroflexible fantasy. Consequently, a lot of times couples like turning this whole experience into an elaborate cross-dressing fantasy, e.g. with the guy in lingerie and the girl in gent’s attire. Or the lady can be imaginatively transformed into a hot trans boy—whatever the two of you like. You can treat your dildo like a cock—the guy can go down on it, give it a hand job, etc.—or you can just treat it like any old toy. Whatever you do, start small and work your way up. This is just like the first time you had intercourse: it’s better if you start with one finger, work your way up to two and maybe three and then move on to a cock (although personally I like fingering even more than strap-on fucking much of the time; however, the vast majority of men and women I know say that cock-like things are comfier in their asses than fingers and hands). Also, keep in mind that pegging may not be thrilling at first, because it requires a lot of feedback to work right–and a very vivid and kinky imagination doesn’t hurt!

Ladies reading this may be skeptically asking themselves, as I did, how am I supposed to get my kicks here? There isn’t inherently a lot of direct physical stimulation for the wielder of a strap-on generally, unless you invest in one of the Feeldoes or similar devices designed for double penetration, which many people find rather awkward. Of course, if it turns you on enough, there’s nothing stopping you from reaching down and touching yourself, but if your boy is reasonably flexible, there’s a decent chance in fucking doggy style that you can make him do the reaching and touching.

Pegging is complicated and more expensive than vanilla sex. But totally worth it, in my opinion.