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Em & Lo:
Advice From Near Experts

by Emma Taylor & Lorelei Sharkey

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Write to Em & Lo for advice, tips, words of wisdom, recipes (or just to tell us nice things) — once a week, we'll answer your cries for help here. We won't publish your email address or send you spam.
May 15, 2003
Baby Got Back (Part II of II)
I've convinced my boyfriend to let me in his back door. Now what?

Dear Em & Lo,

After months of gentle prodding in my boyfriend's butt (first with just a pinkie and then a few fingers), I have finally convinced him we should upgrade to a strap-on. Where do we start?

Knockin' on Heaven's Door
Dear Knockin',

Last week, we discussed the reasons why a woman's boyfriend might be less than stoked to get poked (or "pegged," as Dan Savage likes to call it). In response, we got a lot of emails from women's boyfriends asking us how they might convince their girlfriends to get stoked about doing the poking. Basically, many women have the same fears and prejudices as men when it comes to this orifice, so approach the situation in the same way: If you go in armed with a good argument and even better information, you might be on the slow, gradual climb towards the strap-on summit. We also got a few emails from gentlemen reaming us out, if you will, for giving last week's reader's boyfriend a hard time for being such a tight ass. To this we say: If he's happy to dish it, then he should be courteous enough to offer up his own caboose (at least once). That's the beauty of the asshole: It's the great equalizer. Of course, he doesn't have to like it, but he can't say he doesn't like it until he's made like Mikey and tried it. And if he won't try it, then he shouldn't be surprised when his girlfriend posts a "Road Closed" sign on her butt.

Fortunately, you, Knockin', have moved beyond these issues and are ready to make a beeline for your boyfriend's G-spot. To better address the ins and outs of strap-on sex, we went straight to the lady "behind" the instructional video Bend Over Boyfriend, Dr. Carol Queen. (Hey, even advice columnists need advice sometimes.) According to Queen, it's all about the right kind of equipment: "Strap-on play is a desire many people have, but because it often goes against what they've been taught about sex, they're nervous. The last thing they want is insecurity over, or confusion about, the props adding to that nervousness." How many times has a dildo slipped out of an ill-fitting harness, just to stay lodged in the boy's butt like an obscene turkey timer? One too many. "They think, 'My technology's failed me. Oh, just forget it!'" says Queen. "It's all about staying in the moment and suspending disbelief, so you want to avoid anything that will distract you from that." Like accidental turkey impersonations.

So, first you've got to get the goods. Go shopping together, either online (if you live in Buttfuck) or at your friendly neighborhood sex shop (if your town is that cool). Both Good Vibrations (Carol Queen's second home) and Toys in Babeland have great online services as well as in-the-flesh stores with a wide selection. If you want to keep it simple, stick with the Terra Firma harness. It fits around both thighs, kind of like a jock strap (it's sexier than it sounds). The vinyl version of the Terra Firma is easy to adjust and control, fits snugly but comfortably, and is machine washable! (It comes in leather, too, but we find that too, well, leather.) Get the kind with the adjustable ring size — this will let you can work your way up in dildo sizes while avoiding the dreaded "wobbly dick."

Now it's time to pick your penis! You can pick the color and pattern (they make 'em in tie-dye, leopard spots, even camo!), but he gets final veto on size. Aim low at first: You can always upgrade later. Butt plugs may look like a more friendly size, but they're designed to go in and stay in, not in slowly and out ever so delicately, in again and then out, aw yeah...Get a dildo specifically designed for the tush (long and curved rather than straight and stubby), with a flared base that fits the ring of the harness.

Dr. Queen recommends the following silicone dildos: The Bobbi Sue (as seen in Bend Over Boyfriend 2!), The Techno (smallest), The Cosmo (medium), and The Buzz (the largest of the group, though by no means a monster dong). The Techno is especially recommended for beginners. All four of these dildos have a hollowed out base, which means that — yes, Virginia! — there's room for a teeny-tiny vibrator as a carry-on. (See? The miniaturizing technology revolution didn't just improve laptops.) This will cause the dildo (sorry, your penis) to vibrate at the base, i.e. it's rippling for her pleasure. But chances are, he'll feel a little sumthin-sumthin, too (wouldn't you notice if your boyfriend's penis suddenly started shimmying?). But you may not even need battery-powered help: Sometimes the pressure of the dildo on your clitoris as you thrust is all the buzz you need.

If you're a gadget whore, some harnesses come equipped with little vibe-sized pockets in the wearer's pubic area, for some personalized clitoral attention — but there's more room for error here (too low and you're just stimulating the vulva, too high and it might be pushing uncomfortably on the pubic bone). If you're more into being penetrated while doing your boyfriend, then you can get a double dildo like the Nexus, Nexus Junior, or the Feeldoe — these aren't the straight kind you usually see in porn, but the curved kind made specifically for strap-on sex. Slipping one of these into a harness (if you've got a Terra Firma, you'll just need to remove the back flap) tends to be more manageable than getting a harness designed to hold two separate dildos, one for the giver and one for the receiver. And you thought assembling a desk from IKEA was tricky.

When it comes to the big night — assuming you've worked up to the big night, as we insisted last week — don't even think of whipping out your silicone schlong without lube. (And as with any body part, make sure it's clean and wrap it in latex if you plan on sharing it with any other orifices — or ask your sales rep the proper sterilizing instructions for your particular toy.) Just stay away from silicone lubes, as they cause this bizarro chemical reaction with silicone toys — stick with the water-based varieties, like Probe or Eros Water. Let him ease onto your dildo at his own pace, so he can guide you in at the most comfortable angle. Though you may feel all macho with your shiny new penis, don't get carried away and start thrusting like a frat boy, yelling "Who's your daddy?" Okay, you can yell "Who's your daddy?" but no jack-hammering. And always exit in a calm and orderly fashion, even if he swears there's a fire in his cabin.

Finally, when it's all over, give him a nice blowjob or a cuddle (his choice) and tell him he's been a very good/bad boy (again, his choice).

Who's your mommy?
Em & Lo


About Em & Lo
Em and Lo (Emma Taylor and Lorelei Sharkey) are contributing editors at hooksexup.com, where they created the weekly sex and relationships column, "The Em & Lo Down: Advice from Near-Experts." Launched almost four years ago, it's one of the most popular features among the site's two million readers and is now syndicated nationally. In addition, they write weekly horoscopes for Hooksexup and a monthly advice column for Men's Journal magazine. Their first book, The Big Bang: Hooksexup's Guide to the New Sexual Universe, is now available wherever books are sold (click here to order your copy today). Em & Lo both live in New York City where they spend far too much time together. For more information, visit EmandLo.com.