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.

Peter: What would you do if you had a million dollars?
Lawrence: I’ll tell you what I’d do: two chicks at the same time.
Peter: That’s it, two chicks at the same time?
Lawrence: Yeah, I always wanted to do that, and if I had a million dollars I think I could hook that up too. Chicks dig dudes with money.
Peter: Well not all chicks.
Lawrence: The kind of chicks that would double up on a guy like me do.
From Office Space

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I’m going to say this at the beginning, and I’m going to say this again at the end: guys, you don’t need a million dollars to get threesomes.  I mean, a million dollars will almost certainly get you a threesome with a certain kind of girl, but you can get regular threesomes for a whole lot less if you have something cheaper but possibly just as rare: a slut fetish. Allow me to explain.

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Neither kink culture nor vanilla world often let me forget just how much straight men (and apparently many bi men too) fantasize about the idea of having sex with two women at once.  I’ve spent the last six months or more playing a lot in a crazy triad with my partners, Capt (a man) and VirginSlut (a woman), and being hopeless exhibitionists, we tend to play a lot in public.  I’m regularly amused, a little flattered, and occasionally slightly annoyed by how often guys comment to Capt that he’s “winning” or how lucky he is to be playing with both of us.  The annoyance arises because (1) the reverse is pretty much never true–neither women nor men come up to me and VirginSlut and tell us how lucky we are.  (This is especially funny since women and men both hit on Capt constantly).  And (2) because it feels like there’s an implicit belief that this is somehow all for his benefit–like VirginSlut and I aren’t getting something out of this.  I think both of these points get to the heart of why most straight men never get what they seem to spend a spectacular amount of energy fantasizing about: regular threesomes with two women.

So, guys, I’m going to let you in on three really important secrets.  Okay, are you paying attention?

1. If you want regular threesomes with two women, you have to not think that it’s all about you.  Oooooh, I’m sorry.  Did you think that girls just had sex to please you?  That’s what subs and sluts do, right?  Maybe some of them do; I don’t.  Sure, we create scenes where it looks like that’s the case.  Actually, we stage scenes like that all the time.  We dirty talk that way.  But it’s not really true; it’s not really true at all.  As it happens, we sluts still like to cum.  A lot.  And you have to be willing to put effort into that.  A lot.

And you have to realize that two girls fucking each other on top of you might actually–goddess forbid–enjoy fucking each other when you’re not there too, and that they might not be doing it just so you can get a good view.  Something about straight male culture tends to freak the fuck out when women enjoy fucking each other because… they enjoy fucking each other.  Yup, sorry, both of my girlfriends’ hands are bigger than your cock.  Get. Over. It.

Connected with that, you’ll get better at threesomes with women if you think outside the box, as it were.  Spending all your time trying to figure out how to get your dick into two women’s pussies may be a fun exercise for jerking off, but it’s often a very impractical reality.  You make a much better impression if you’re willing to use all your assets–hands, tongue, and dick (and even better if you add your ass to that)–to please us.  “My ass???” the stereotypical straight male dom says in panic.  Oh, yes, I said your ass; we’d love to peg it.  This is all related to the second secret.

2. Sometimes, your best bet is to offer yourself up as a sacrifice for our pleasure.  Good luck finding your idyllic threesome arrangement if you don’t find the idea of two women using you for their pleasure to be wicked hot.  Remember I said that we want something out of this too?  The sacrifice of your body is a rare and precious thing you can provide us with.  I’ve actually used my husband’s cock to fuck women with on several occasions, always to great effect, earning him the nickname “the human dildo.”  (We described the scene to a vanillaish friend who said seriously to my husband, “That sounds traumatizing!” [To be used like that]. He quipped, “I know. It was so traumatizing that I’ve been fantasizing about it ever since.”).

You want to drown in pussy?  Then beg for a girl to sit on your face while another one sits on your dick and they make out.  Let us gangbang your willing ass.  Put a hand in each of us while we grind against each other.  Then maybe you’ll get that two-girl blowjob you’ve been fantasizing about… some of us having actually been trying to really work on the fine art of giving one.

3. Get a slut fetish. This one’s really the heart of the thing.  Other than the simple reason that triads are incredibly unstable relationship dynamics, the real reason most guys can’t get a threesome lasting longer than a night (if that long) is because they don’t have what it really takes to get and keep two women: a slut fetish.  Yes, it’ll do if you don’t mind the fact that we’re going to fuck other guys too, but if you’re actually into it, then your chances of keeping us go way up.  Ahh, now I really heard the straight male dom panic sputtering again in the background.  “But, but, my cock isn’t good enough for you?  You want other guys too??”  Um, yes.

The thing that neither vanilla culture, nor kink culture (to a lesser degree) seems to fully appreciate is that the “kind of girls” who will gleefully threesome a guy tend to be 1. prostitutes 2. sluts and 3. not straight.  If you’ve nixed the prostitute part of that equation, you’re left with “greedy sluts who like to have their holes filled by an array of genitalia, random body parts, and other assorted objects.”  We’re sluts.  Which means that we probably have (or at least could have) a number of guys with a variety of impressive sexual assets in our contacts list, under our skirts, on a leash, or in a cage in our house.  But we’ll keep coming back to you in pairs or more because you accept us for who and what we are and are turned on by it.  And if you don’t freak out at the idea of us sleeping with other guys.  And girls.  And assorted other genders.  And if you’re actively turned on by it, then you get major bonus points.

Oh shit!  It turns out that sluts are also people, not just a greedy collection of holes (even if we like to be dirty-talked like that’s all we are)!  

The thing is, it’s not hard for two girls who really want to fuck a guy together to go out and find a guy to screw.  In reality, even if the girls in question are only moderately attractive, there will probably be a long line of men volunteering for the position.  So women who want that can afford to be pretty picky about the guys they take, even if their slutty dispositions disincline them towards selectivity.  Which in turn means that if it’s something you really want, you really have to stand out from the crowd.  Real, live, socially well-adjusted, slut-fetishizing men are about as common as… well, they’re not common.  So if you can condition yourself to get a slut fetish, you can vastly improve your chances of making your fantasy a reality (no promises, though).

The point is, you don’t need a million dollars.  You just need a slut fetish (which is probably even harder to come by for some people).

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For my birthday, a dear friend SteelZombie searched for “slut” on etsy.  She found a woman who makes cute matching necklaces that are usually sold in pairs, with one saying “slut” and the other “master.”  Knowing VirginSlut’s and my relationship dynamic, she wrote to the woman and asked, “Can I get two sluts?”  The woman said “Sure!”  It usually isn’t that easy.  Sorry, guys.