How to Bend Over Your Boyfriend and Make Him Like It

While it still remains taboo in some circles, heterosexual anal sex seems to be gaining in popularity, and some couples are even exploring male anal penetration by the female partner, a sexual practice known as Bend Over Boyfriend (BOB) or pegging. These days more and more men are becoming interested in anal pleasure and comfortable with the idea of letting their female partners take control in bed.

If you’ve decided to make your boyfriend’s or husband’s strap-on fantasies come true, you need to get the right equipment: a sturdy strap-on dildo and a reliable harness to hold it in place. When starting out, it’s best to choose a dildo on the smaller side, for comfort’s sake. A dildo of 5 to 6 inches in length and 1 to 1.5 inches in diameter should be an adequate size for your first strap-on. Choose a dildo that has a flange at the base that will secure it in a harness, and buy a sturdy harness with adjustable straps, preferably one of leather, vinyl, or other strong material.

Some dildos have an upward curve or special shape designed to stimulate the prostate. The prostate gland is located between the wall of the rectum and the bladder and is about the size of a walnut. It is the male equivalent of a woman’s G-spot, and stimulating it can greatly increase the intensity of the man’s orgasm, and sometimes the force or quantity of his ejaculation. While prostate stimulation can be achieved with a standard dildo, having the angle built in makes it that much easier to hit your man’s hot spot.

Once you have your strap-on firmly in place, apply a generous amount of water-based lubricant to the head and shaft of the dildo and to his anus. You may even want to massage the lube into his hole with a finger or two to help relax his sphincter. If you really want to dominate your boyfriend, make him apply the lube to your dildo and his anus himself.

Once you’re all lubed up, steady the dildo with one hand and place the head squarely against his anus. The most comfortable position for anal sex is with him lying face up with a pillow under the small of his back and his legs pulled up. You then enter him from on top, in a missionary-style position. In this position, you can kiss him, squeeze his nipples or stroke his penis. However, many couples like having the man bend over something that is less than waist height – a table, a chair, the bed, etc. – or take it doggy-style because these are more submissive postures.

Keeping a grip on the shaft of your dildo, guide the head directly into his anus and gently push it inside him. Instruct him to bear down as if going to the bathroom while you do this, to open up his sphincter muscles. Once the head of the dildo disappears (or the dildo enters into him about an inch or two), pause and let him get used to the feeling of having something up there. Then place your hands on his hips and begin pushing forward steadily until the dildo is all the way in. Take a couple of breaths and let his sphincter adjust and relax. Pull part way out slowly and push back in. Pull out, push in. Continue doing this, increasing your speed and force as you go.

Essentially what you are doing is massaging his prostate gland. Not only will he enjoy this, but it will also make his penis start dripping, and he may even ejaculate without direct penile stimulation. You can increase the stimulation by exerting pressure on the dildo in the direction of the prostate so that the shaft rubs more firmly against it. Also, concentrating your thrusting motions in short, rapid movements will provide more stimulation against that area.

Keep a steady rhythm going, but pay attention to the intensity of his moans and groans, the speed of his breathing, and his body’s actions. Communication is important, so be sure he lets you know what he wants and tells you if he feels any discomfort. Though you may be afraid of hurting him, if he’s begging you to pound him and pushing himself back onto your dildo, it’s a sign to let yourself go. You may find yourself surprised at how turned on you get when you allow yourself to enjoy the feeling of being in control.

Beyond male anal pleasure, there is a lot to explore in the area of role reversals with BOB. It’s a chance to explore the ways you feel – masculine and feminine, bottom and top – and a chance to relate to your partner in a completely different way. Bend Over Boyfriend is a sexual practice that comes with deep potential for personal growth and really hot sex!

If you’re a woman who is turned on by the idea of pegging your man, but he’s not so eager, try the tips in my post Bend Over Boyfriend: How to Make HIM Want Anal Sex. You may be shopping together for a strap-on sooner than you think!

My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here.