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

BOB Kit + Bend Over
Boyfriend DVD Combo

Joque Harness
(dildo sold separately)

Sliquid Sassy Booty Lube

Deluxe Anal Douche

Aneros Prostate Stimulator

Little Flirt

Pop Plugs

Silk Dildos

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 So Great About 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 most direct way to stimulate the prostate, the male equivalent of the G-spot. To find it, insert a well-lubed finger anally and feel along the front wall of the rectum (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 a walnut. 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!" Generally, anal sex hurts if you're going too fast or without lube. 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 or Sliquid Sassy Booty Lube for anal play. (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 at some point in your anal sexplorations, 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. Many people find that a thorough wash in the shower does the trick for removing any surface grime. If you're fastidious about cleaning, try a Deluxe Anal Douche; douche with regular room-temperature tap water (no soap!) a few hours before you play.
"It means you're gay!" People of all genders and orientations enjoy anal play. We all have butts, after all! 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 a well-lubed finger into the anus. Ask your partner to push out gently 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, Ripple Plug, and Pop Plugs.
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 self-lubricate, so add even more lube than you think you need. Generously lube the anus and your toy, and reapply often. A thick lube like Sliquid Sassy Booty Lube stays where you put it, and can protect delicate anal tissues.
Go slow. Especially at first, when your toy or finger 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.

Harnesses. The Jaguar harness is very stable and comfortable. It is also extremely versatile with interchangeable O-rings which can accommodate different sized dildos. The Joque 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 sleek as their name suggests. The smallest one is about the size of a large finger. If you're using a dildo in a harness, choose one with a slight curve and strap it in so the curve points toward his prostate (up or down, depending on the positioning of your bodies). The G-Curve is a great choice for boys who like prostate action, while the long, slim Vibrating Mistress is the answer for people who have trouble with shorter dildos popping out during use.
"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. or Share allow for both partners to be penetrated at once. The ingenious Buzz Me Tender harness has strategically-placed pockets for vibrators. The Bend Over Beginner kit has it all: a plush harness with an included vibe, and two silicone dildos, in different sizes.