How to Bend Over Your Boyfriend (anal penetration)

Find out why "bending over your boyfriend" is all the rage. A how-to for people who want to strap on dildos and anally penetrate their partners!

How To Bend Over Your Boyfriend

by Alicia Guinn

Bend Over
Boyfriend 1 DVD

Bend Over Beginner Kit

BOB Kit + Bend Over
Boyfriend DVD Combo

Velvet Harness
(dildos sold separately)

Maximus Lube

Anal Douche

Little Flirt

Tulip Plug

The Ultimate Guide
to Strap-On Sex

Silk Dildos

Raquel Dildo

We love anal play here at Babeland! Over the years we’ve been thrilled to see an amazing increase in the number of couples wanting to explore anal pleasure. It’s heartwarming to see all sorts of people--from punk kids to grandparents-- shopping for dildos and harnesses and exploring an often overlooked center of sexual pleasure. The phenomenon of women penetrating their male partners (also called pegging) has spawned a successful video series called Bend Over Boyfriend, a great resource worth checking out.

What’s with Anal Sex Anyway?

People love anal play because it feels great. While our society is rife with rumors that anal play is painful and damaging to our bodies, the truth is that butt sex can be healthy and extremely pleasurable. Our assholes are packed with nerve endings, and they’re the same kind of nerve endings found throughout our genitals: the ones that make other types of sex pleasurable. Anal penetration is also the only way to stimulate the prostate, the male equivalent of the G-spot. To find it, feel the front wall of the anus (toward your partner’s belly button). It’s about two to three inches inside, and it has a slightly crinkled texture that people compare to the surface of an almond. Some men can have orgasms from having their prostates stimulated.

If your partner is hesitant to explore their butt, you may have to dispel some of the rumors they've heard about anal sex. Let’s just address some of the common myths upfront:

"It hurts!" Anal sex only hurts if you’re doing it incorrectly. The majority of us carry a lot of tension in our assholes--the same way we carry stress in our shoulders. Pain results when an object is forced through tight sphincter muscles, damaging the delicate anal tissues. If anal sex ever hurts, you should stop or take the stimulation back a notch. Remember--the key to anal pleasure is relaxation and lubrication! We highly recommend Maximus for anal. (Please don’t ever use numbing creams for anal sex. Pain is a warning signal from our bodies that we should take seriously.)
"It gives you hemorrhoids (and/or uncontrollable bowels)!" Most people find that when they start exploring butt play, their anal health improves. All muscles benefit from the increased circulation that results from exercise and relaxation.
"It’s messy!" Although you’re likely to encounter some poop in your anal sex career, it’s probably going to be a lot less than you imagined. Most anal play engages only the first few inches of the anus and rectum, which do not store feces. Most people find that a thorough wash in the shower does the trick for removing any surface grime. If you’re fastidious about cleaning, try an Anal Douche with regular room temperature tap water a couple hours before you play.
"It means you’re gay!" People of all genders and orientations enjoy anal play. We all have butts! Besides, it’s a myth that all gay men only have anal sex. In fact, the majority of gay men report that oral sex is their favorite sexual activity.

The Right Stuff

So what’s the "right way" to do anal sex? Each of these steps is crucial to happy butt sex.

Relax. Bend-over beginners need to learn to relax the sphincter muscles that ring the anal opening. Learning to relax these muscles can take time--especially after years of neglect or tension. Run your finger along the anus to relax it first. Gently insert lubed finger into the anus. Ask your partner to push out as if trying to have a bowel movement, and that will relax the outer sphincter enough to slip in a finger or butt toy. Good beginner butt plugs are Little Flirt and Tulip Plug.
Communicate.It’s important that the person being penetrated control the pace of play. Nothing should ever be forced or hurried in anal play, and partners should stay in close communication about what feels good--and what doesn’t.
Use lots of lube. Don’t skimp on lube! The fragile lining of the anus does not lubricate sufficiently for pleasurable anal sex. Add more lube than you think you need. Generously lube the anus and your toy, and reapply often. A thick lube like Maximus stays where you put it and can protect delicate anal tissues if you use enough.
Go slow. Especially at first, when your toy or finger first enters the anus, your partner will need some time to adjust to the sensation. Check in about what feels good. As he learns to relax his sphincter muscle he'll probably request more vigorous thrusting.

Saddle Up, Cowgirl!

Once you’ve both mastered the "ins and outs" of anal play, it’s time for action! Here’s a quick guide to harnesses, dildos, and other anal accoutrements. For a more thorough guide, pick up The Ultimate Guide to Strap-On Sex by Karlyn Lotney.

Harnesses. The Terra Firma harness is very stable and comfortable. It is also extremely versatile with interchangeable O-rings which can accommodate different sized dildos. The Jaguar Harness is another top notch, extremely comfortable harness.
Dildos. Many people prefer to start small with dildos for anal play. If you’re using a dildo by hand, make sure that it has a large base to keep it from disappearing into your honey’s butt. That same base allows you to use the dildo in a harness. Silk dildos are as smooth and silky as their name suggests. The smallest one is about the size of a finger. If you're using a dildo in a harness, choose one with a slight curve and strap it in so the curve points up, so it'll better stimulate his prostate. Bond's curve makes it a great choice for boys who like prostate action, while the slightly larger and longer Mistress is the answer for people who have trouble with smaller dildos popping out. In addition, the Raquel, Leo, and G-Force dildos can be great additions to your anal sex toy chest.
"What’s in it for me?" Besides seeing your sweetie writhing in ecstasy, you can double your own pleasure while wearing a harness by following one of these tips. Double dildos like the Nexus Jr allow for both partners to be penetrated at once. The ingenious Buzz Me Tender harness has pockets for vibrators near both the clit and the crotch. The Bend Over Beginner kit has it all: a plush harness with an included Zippy vibe, and two Silk dildos, in different sizes.