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Bend Over, Boyfriend

Women, Men, and Male Anal Play

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Updated June 18, 2014

While it still remains taboo in some circles, heterosexual anal sex, seems to be gaining in popularity, and more and more male/female couples are turning the tables, exploring male anal penetration by a female partner, a kind of play that’s affectionately been nicknamed BOB, or bend over boyfriend.

Carol Queen, sexologist and sex activist, refers to anal play as the great equalizer. She points out that the bum, the anus, the rectum, even the sphincter muscles, can be sites of immense physical and psychological pleasure, and that this pleasure is open to all, regardless of gender or sexual orientation.

When I first started working in sex stores, there were straight couples who would come in to buy dildos and harnesses to explore male anal penetration. But they were few and far between, and the guy would stand in the opposite corner, nervously watching to see what his partner was buying for him. These days there are books, educational videos, and even toy kits devoted to BOB, and while it can still be nerve wracking at first, guys are warming up to it.

Being penetrated can be a profound emotional, psychological, and spiritual experience. It can also be a lot of breezy fun without deeper meaning. It is what you make it, and you need to find out how it feels best for you if you are interested in giving it a try. Here are some tips for safe and fun exploration of male anal play:

Get Used to Talking About Sex, You’ll Be Doing Lots More Talking

Any sort of anal play requires tremendous trust and a lot of sexual communication. If you’re interested in checking this out, bring it up and see how your partner feels about it. Choose your time wisely, and be prepared for some hesitation at first. There is an element of role reversal and gender play with BOB, and people can have unexpected reactions at first.

Bend Yourself Over First: Exploring on your own

If you’re a guy who wants to be penetrated, get comfortable with anal play on your own. You don’t need months of practice before you get a partner involved, but if you’ve never been down that road, check out what’s going on. Learn about male genital anatomy, and start to incorporate anal pleasure into your masturbation. You’ll be in a better position (no pun intended) to tell your partner what you like and what you don’t if you’ve done a bit of homework beforehand.

Bend Over Boyfriend, without the accoutrements: Playing together without toys

Generally when people talk about BOB they think of a woman strapping on a dildo and lovingly giving it to her fella. Strap on sex can be awesome. But start slow, and with your own body (fingers, etc…). Get some latex gloves and a good quality personal lubricant and explore with your and your partners fingers. There can be a lot of mystery around anal play, particularly for men, so take some time to get comfortable before you introduce toys.

Go Bend Over Boyfriend Shopping!

For some of us, this is almost as much fun as the play. Make sure you find a good sex shop one that will accurately answer your questions. There are several things to consider when buying a harness and dildo. If you don’t have a store near you, there are plenty of excellent online sex shops that carry hundreds of different dildos and harnesses to suit everyone’s tastes.

You may also want to check out the highly recommended educational title Bend Over Boyfriend. The video is available at most good quality sex shops, and you can purchase it directly from Fatale Media on their website.

Strap It On

If you’re doing the penetrating, make sure you feel comfortable and in control with your harness and dildo. Practice putting it on and taking it off on your own. You might want to wear your harness and dildo around the house for a while to get a feel for it. Learning to use your hips and/or lower back, your upper legs, and other parts of your body to penetrate your partner can take some time, but the practice can sometimes be the best part.

Bend Over Safely: Safer strap-on sex

As with every kind of sex play, give some thought to how BOB play can be safe and fun for both of you. All the regular rules about anal safety apply here. Make sure you clean your toys properly, and most importantly keep talking before, after, and during sex, to make sure that what you’re doing feels good for both of you.

Taking it Deeper with Gender and Role Play

Beyond male anal pleasure, there is a lot to explore in the area of role reversals with BOB. For both partners turning the tables can be a whole new world. It’s a chance to explore the ways you feel masculine and feminine, bottom and top. It’s a chance to attend to your partner in a completely different way. The fact is that in mainstream Western culture “sex” still means man-on-top-penis-in-vagina-over-in-four-and-a-half-minutes sex. Bend Over Boyfriend is a radical sex act, and it comes with deep potential for growth and really hot sex!
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