Thomas Roche: Memo to the Pegged

So it's happening. You're a guy; you've got a lady; any minute now, she's gonna have a dick. She's talked you into it; you've talked her into it; you've talked each other into it, or maybe you've high-fived each other and chest-bumped while she reaches for her strap-on. You're about to be pegged for the very first time.

Now comes the easy part, right? Because if you're a guy, getting pegged by a woman with a strap-on consists of one simple thing, right? You just, you know, bend over.


Wrong. If you're about to play with a a hot woman with a strap-on for your very first time, learn one simple fact before you ever drop trou: getting pegged is not about "taking" "it" "in" "the" "ass" -- it's about sex, with a woman with a dick (in this case, of the strap-on variety).

So much of the propaganda in favor of chicks wearing strap-ons with dudes is about her doing him in the butt. Which is awesome. But it's far from the whole story.

I'm here to tell you something important: the more you take the lead, the more fun you'll both have.

Are You a Do Me Queen?

Look, don't get me wrong. There are a couple of reasons why you could want to be totally passive in an anal-receptivity adventure. Strap-on sex can be a profound expression of dominance for her, a a wonderful manifestation of submission for you. You might want to be totally submissive and receptive; you might have no choice, as she could conceivably have ordered her cat-suited minions to dress you like a tart and place you in suspension bondage with your ankles stuffed into your ears.

But that's not what we're talking about here: If she's just an average girl in an average world, and you're just an average guy looking to spread his thighs, and this is the first time the two of you have played with strap-on sex together, then this'll be important advice.

One thing's for sure; if she's looking for a Do Me Queen -- that's BDSM or queer slang for a person, man or woman, who just lies there with his or her ankles or ass in the air -- she'll assuredly let you know. If she's an experienced strap-on expert and has fucked lots of guys, maybe she wants you to lie there and take it.

If that's the case, chances are damn good that, even so, she'll be stoked to get the chance to exert a little dominance. If she's the type to want a passive partner, and she needs to wrestle you to the bed and pin you with your ankles behind your ears, it's a good bet she'll figure that out.

But given how many women fantasize about strapping one on with men but never get to do it, or get to do it only infrequently, it's a much more common scenario that either 1) she's a beginner, too, or 2) she's done this before, but is still a bit shy about doing it with a new partner. That's where you come in -- seriously, don't just lie there. Don't just shrug and say "Okay." You're about to be fucked in the ass, man! Show some fucking balls!

Your confidence will encourage her confidence, and you'll both have a hell of lot better time.

What does that mean? It means engaging all her five senses.

Cock Gobbling In Five Senses

Look at it. Know how great those eyes of hers look when she's happy? Give 'em a feast.

Not just the sight of your sweet pansy ass getting plowed; it's too hard to count on that being a turn-on for her. It probably will, but why start there, when the experience of strap-on sex is half over? Don't sit there and stare aghast at her dick like it's an onrushing semi at 4am on the Interstate and you're a very small gopher who just had to have that dandelion on the other side of the freeway. Let her see that you dig that funky dong between her legs -- or if you don't, either start to dig that funky dong, or change your plans. Nobody wants a half-assed butt-fuck, now, do they?

Let her eyes see your eyes -- looking at her dick. When she shows up in the bedroom door wearing that mammoth silicone dong with her sexiest nightie and six-inch fuck-me pumps -- or skintight boyshorts and knee-high cowboy boots, or false moustache and lime green sombrero, or fright wig and clown makeup, or nothing but a bend-over-bitch grin -- look at her, and in particular look at it. Look at your lady's dick.

Look sexy; look hungry. Make eye contact, then look at her dick. Look at her dick, then make eye contact. Lick your lips. Open your eyes wide.

Meanwhile, see the point below about dirty talk -- mix up eye contact, inspired dirty talk, audible horny panting and visibly ravenous dick-checks and you'll engage her fully.

Extra bonus points if she can see you drooling. Extra-extra bonus points if she can see you drooling, looking at her dick, looking at your dick, looking at her dick, and thinking to yourself "Guess you're the superior stud, baby."

Coo for it. That's right -- make love to those ears of hers. Don't just moan and whimper. Involve every communication tool from the get-go to tell her how hot she looks; talk dirty, and if you can't talk dirty, learn. When you get that first glimpse of your fine lady's prong, you don't say "Um, it doesn't look that bad," or "Uh, [shrug] it's okay," or "Was it always brown?" You say "Holy fucking shit that looks fucking hot, baby." Or, better yet, "Daddy." Say, "Oh fuck, I can't fucking wait for you to put that thing where it belongs, you hot fucking stud--right up my tight virgin--" you get the idea.

Once the action gets going, you can keep up the talk if you're down with that (and you should absolutely stay in verbal contact about what feels good and all that), but the critical point for verbal engagement and encouragement with a new experience is when -- if you'll forgive me -- your baby whips it out.

Touch it and reach for it. That's right, reach for that dong. Don't extend two nervous fingers and poke the thing like it's a dead whale carcass. Don't turn it over and peer at it, frowning intently, the way you would if you were examining the very same dildo on the shelf in some high-class sleaze shop, deciding whether to buy this one or that one or maybe the Mark VII Mister Throb Butt Blasting Power Reamer. This is your lady's dick, man, get a grip on it!

Reach for her dick the second you're in reaching range; touch it like it's part of her, because it is. Or if it's not, then with the right amount of encouragement, maybe soon she'll feel like it is.

Treat it like it's a real dick; stroke it, fondle it, caress it, jerk it off, point it where you want it to go. If you're not a man who regularly fondles other men's Johnsons, this may prove a new and even challenging experience for you. More importantly, it may feel bizarre and awkward to treat what is for all intents and purposes a prosthesis as if it were human flesh -- but ain't it worth it to try? On some level this is role playing; the more you believe it the realer it is. Make it worth your lady's dick's while, and it'll make it worth your while.

Speaking of which, now is probably the time to mention that depending on a lot of factors, there is every possibility that she could feel a certain amount -- from a little to a shitload! -- of physical pleasure from your handling of her pene. The thing is, the base of that dildo is sitting right on her pubic bone; some women are constructed that that means, given the right angle and pressure, something pretty damn cool -- clit, clit, clit.

What's more, some strap-ons allow the user to enjoy herself with a second dildo inside her, so the jostling of her package may, you know, jostle her package. Then, of course, there's always the possibility that she's got a vibrator tucked between dildo and clit; there may be a telltale buzzing, but if you're taking my advice you could be too busy saying "Yes, Daddy, please, Daddy, may I have your cock, Daddy" to really hear whether she's buzzing her clit to death. Don't bother to ask; just assume any moans you elicit when you run your thumb across the ridged underside of her prodigious member are 100% real.

Some women, by the way, are not constructed so that clit stimulation or other physical pleasure are really easy to get from wearing a strap-on. Women are so individual, and dildos and harnesses so varied, that it's hard to predict what the sensations of wearing a strap-on are for her, which is why you should be caressing her dick like it's the greatest treasure on Earth, rather than staring at it blankly; it'll help you find out what she likes. Believe it or not, touching her when she's wearing a strap-on will tell you scads about her body.

Even if the turn-on is entirely psychological for her, remember -- this is on some level role play, in which context that dick is part of her. The more affection you lavish on it, the more genuine you're helping make the experience.

Incidentally, while you're at it? Feel free to touch the rest of her, too -- touch her tits and her ass and her thighs and her belly; kiss her and caress her and blah blah blah blah. All the stuff you'd usually do, but more of it -- no reason to skimp on physical affection now that she's got a dick. Unless -- and it's a big unless -- she's really getting into the whole idea that she's male, or a Daddy, or a stud or a fag boy or just a stone butch plowing you, or whatever. In that event, she may not necessarily want you fondling her girl-tits or tracing her womanly curves with your fingers -- if that's the case, surely she'll let you know. Read her body language, which is a great suggestion on all fronts.

Smell and Taste. If you don't already get aroused by the faint smell of silicone, lube or leather, don’t worry -- if you become a regular practitioner of this kind of pervery, you probably will. But in the meantime, just because your woman's wearing a dick doesn't mean she doesn't smell as good as ever; enjoy it.

More importantly, taste her. I don't mean eat her out -- though a rim job while she's wearing a strap-on may be a delightfully playful pleasure. I mean be a cocksucker, cocksucker.

Why You Really (Really!) Need to Suck Her Cock

I have often heard viewers of strap-on porn bemoaning the very idea that anyone would want to suck a strap-on, or be sucked while sucking a strap-on. I mean, the wearer doesn't feel any pleasure, right?

Wrong. Even apart from the notes above about the physical pleasure some women can feel while having their strap-ons enthusiastically manipulated, the erotic charge that strap-on wearing females can feel is intensely augmented by ritual. This may have to do with her dominance, your submission, with her power -- it's all kinda complicated, and individual to each person.

But people who like to spend time around flesh-and-blood dicks in that special way people like to spend time around flesh-and-blood dicks almost always want to suck said flesh-and-blood dicks. Sucking cock is one of the most powerful rituals around; at risk of sounding like a sociologist, I'll say that it's an important -- for many the important reifier of heterosexuality, homosexuality, bisexuality, whateverthefuckasexuality, queerness, perviness, trans identity, cisgender identity, submission, and about a million other things. It can even be a profound expression of lesbian identity. Cocksucking is important; all forms of sex are important, but for many people cocksucking is uniquely powerful.

How can cocksucking be so many things to so many people? Fuck if I know, and who cares? Just do it. Engage in that ritual, cocksucker: Cocksuck!.

Cock Gobble, Don't Cock Suckle

And I don't mean put it in your mouth and look up at her blankly. I mean really go to town on that shit. Seriously.

Because strap-on cocks don't actually possess nerves -- give those scientists time -- meek, half-hearted cocksucking that might feel pretty good on a flesh cock will likely be less exciting on a strap-on cock. You need to get excited, here; get energetic. Wrap your hand around the shaft and your lips around the head. Slurp up and down. Bob your head like you're at an Iron Maiden concert. Jerk your lady's dick like you own it. Drool everywhere -- I mean everywhere. Bonus points if she has to wipe her boots afterwards (or make you lick your own spit off them, pervert).

Extra-extra-extra bonus points if you deep-throat, by the way. Getting her cock all the way down your throat is an even more profound expression of the cocksucking dynamic than just plain going garden-variety wild thing on it. As to how to deep throat, that'll have to wait until later -- but rest assured, it's easier than it looks.

And Now, The Anal Sex

As I mentioned above, to read about female-on-male strap-on interactions, you'd think every strap-on dildo rolls off the assembly line already up some guy's ass. The preceding paragraphs will, hopefully, encourage you to think of the interaction less as a female-on-male buttfuck and more as a male-on-female-with-a-strap-on par-tay.

But there's a lot to be said for pegging -- and lots will be surely said for it in many places on this site. For the purposes of this article, the important point is that even if you do get pegged -- before, after, or during your many other satisfying strap-on interactions -- it's not a simple matter of bending over.

It should go without saying that during receptive anal sex, your safety and comfort is your partner's concern sure -- but she doesn't know what you're feeling. The anus is a sensitive little pucker, there -- take an active role by communicating, whether or not your fantasy includes you being passive. Don't just lie there and expect her to do you -- even if you're a submissive little butt boy, at the very least make sure she knows what you're feeling and, ideally, just how damn much you enjoy yourself.

And if your getting-buttfucked fantasy isn't about being passively plowed, then there's room for even more kinds of fun. You can take as much of an active role as you want in your own defloration -- and, if you're being deflowered, it's a good idea if you do. When the "passive" partner -- the one being penetrated -- takes an active role, he can control the angle of penetration, speed of penetration, amount of lube, rate of thrust, depth of thrust, etc -- all those things that can cause, alternately, discomfort or pleasure.

The more in-control you are, especially for your first time, the safer, physically, your butthole will be. If you want her to lay you down and do you, that's awesome, too, but for your first time, it's a great idea to transition all that eager, man-eater cocksucking into a leadership role for your own plowing.

First, don't be afraid to use your hands to guide her cock into you. The more manual control you take over it, the more you'll be in charge of what you're feeling.

Second -- did we mention lube? We should be mentioning it all the time. The anus is not a self-lubricating mechanism like the vagina; you need lube, and spit is not enough -- especially for your first time. If you're using a condom to keep her toy clean, it's even more important to use lube; many people find that for anal play, a thicker lube (more like KY jelly than like Astroglide) is a big plus. You're likely to want a lot of lube. It's not a bad idea to put down a towel or two so you won't be inhibited in applying the stuff.

Last, and most important, pick a position that allows you to control the penetration. This will take some experimentation, because every pair of bodies is constructed differently, and fits together differently. If you straddle her reverse-missionary position -- called the "female superior" position when it's you penetrating her -- it's often said to be reasonably easy to control things. But if you're less physically fit, that's not going to be true.

In that case, "doggy style" can be a very good position to give you control -- even if you're not muscular, a guy's thighs tend to be his most powerful muscles. In that case, if you're in control, have her remain relatively still and push yourself back onto her. You won't be able to see what you're doing, so don't be shy -- use your hands.

Another preferred position for giving you some control is to do it "spoons" style -- both of you turned to the side, facing the same direction. It's a bit easier to see what you're doing than it is doggy style, but you'll still need to use your hands a lot.

A Few Last Words About Shyness

One or both of you have presumably been fantasizing about this moment for quite a long time; ideally, both of you have. But one of the reasons people don't get active and have fun during strap-on sex -- as with any kind of new sexual adventure -- is shyness.

If you feel shy about being sexual with a girl wearing a strap-on for the first time, I don't blame you -- it's new and different.

You're probably used to being with women without dicks, to reaching down and finding an irresistibly delectable womanly hoo-hah. Now you reach down and find a phallic device with one primary Earthly purpose -- to invade human orifices. (Okay -- strap-on dildos also look awesome, but that's probably not their primary purpose.) Sure, okay, W00t! But it can throw you for a loop.

If you're feeling shy about getting up close and personal with that dick, then there's only one thing to do -- get over it. Dive right in and be active, and let her take the lead when and if she feels confident enough to do that.

And if she's the type who wants to pin you down and take you -- well, you'll get that message pretty quick.

But even then, she'll probably enjoy herself more knowing how bad you want it!

Thomas Roche has been a training instructor at sex-ed nonprofit San Francisco Sex Information, where he lectures on a variety of human sexuality topics, since 1997. He has also written hundreds of articles on human sexuality and has served as Web Magazine Editor and Marketing Manager at Good Vibrations, as Content Release Lead at, and as Director of Customer Service at His erotica has appeared in more than 200 publications, including several volumes of the Best American Erotica series and the Best New Erotica series, as well as many other anthologies and websites. Find him at