A Beginners Guide to Safe and Fun Pegg

Pegging, also called "bend over boyfriend" or BOB, may not be everyone’s cup of tea. But for couples who have a foundation of good communication and are looking for a new avenue to explore, pegging offers a new world of stimulation for him and a wonderful opportunity for role play and power exchange for both partners. There’s no one way to peg as long as you follow the basics of safe anal play. But if you’re looking for a place to start, this step-by-step might help.

Talk First

Anal penetration of any kind requires a lot of communication. You can have perfectly safe anal penetration without any pain just as long as you listen to your body and if you’re feeling pain or discomfort you slow down, add more lube, and try a different position or form of stimulation. All this means you need to be able to talk first. If you can’t talk about the idea of pegging you’re probably not ready to peg (or at least not ready to peg safely). Tips on how to talk about new sexual ideas with a partner.

Get Comfortable With Anal Penetration

If you’re a man looking to get pegged it may not be the best idea to make that your first experience with anal penetration - amateur pegging. Start on your own. Before you invest in toys and gear, just start off with your own fingers (be sure to use lots of water-based lubricant and latex or non-latex gloves). You may want to experiment with self-prostate massager to see how it feels and whether you like it or not. Exploring on your own will also make you a better and more receptive partner.

Get to Know His Anatomy

If you’re the female partner make sure you not only understand the basics of safe anal play but also are familiar with male sexual anatomy (particularly the anus and the prostate gland). A great way to get a crash course on what he likes is to ask him to pleasure himself and let you watch. Not everyone is comfortable with this and one way to reduce self-consciousness is to have him wear a blindfold. This makes it easier for him to slip into his imagination and you can feel free to get as up-close as you like.

Get Your Gear

Finding a good quality strap-on and the right dildo is key to a positive pegging experience. The female partner should choose the strap-on. There are several things to consider in choosing the right strap on dildo harness. Just as important is finding a dildo that’s the right size and shape. There are some specific things you need to look for in a dildo for pegging. In addition to a dildo and strap-on, make sure you have plenty of water-based lubricant on hand as well as gloves and, depending on your dildo material, some condoms.

Try It Out Solo

Pegging offers the potential for intense role play and gender bending experiences, and many people are surprised by how much they are turned on by the feeling and how “real” it feels. Still, for most people the first time they try a strap-on on, it feels awkward and strange. Once you’ve got your gear home try it on by yourself. Try it on under your clothing and see what it feels like to undress with your strap-on. Try moving around, dancing, even masturbate all with your strap-on in place. This will help you get used to the feeling and learn how your movements make the dildo move.

Don’t Stampede to the Pegging

Anal penetration can never be rushed so if you’re planning on some pegging, schedule in a lot of warm up time. Make sure you're both really turned on, relaxed, and ready. Some couples will start with penile-vaginal intercourse and then switch to pegging. There’s no one way to do it, just be aware that it’s not like porn.

Let Him Take It In

Once you’ve explored the outside of his anus and got him ready gently put the tip of the dildo up against the anus. Don’t try to push it or force it in, instead, let him relax and take the dildo in. Once the dildo is inside him avoid fast movements at first, pay attention to the movements of his body and move with him. The dildo may slip out but don’t pull it out quickly (unless he asks).

Don’t Forget to Add the Lube

Keep a bottle of lubricant handy and be sure to keep adding more lube to the dildo as your playing. If the dildo is partially inside him you can apply lube to the part that isn’t, and as you're playing, when the dildo is fully out of his body, apply more to the tip and the entire shaft.

Let Him Set the Pace

One way of letting him determine the speed of strokes and the depth that he likes is to get him to move and, at first, you stay relatively still. If you're brand new to pegging this is a safe way to start and it gives you time to watch how he moves on the dildo and what he likes. Remind him that he can always go slower or faster; all he has to do is ask.

Follow His Lead, But Start Slow and Shallow

This doesn’t mean you’re off the hook. Once he’s comfortable with the dildo it’s time to start taking control. Begin with slow and shallow penetration. Here’s where having a smaller dildo can really be a benefit as it means you don’t have to worry as much about going too far. As you both get into it and are more comfortable you can experiment with deeper thrusting, but pay attention to what he says and what his body is telling you.

Don’t Forget About the Other Body Parts

The focus of pegging may be on the bum, but it’s still sex play and if you can bring in other parts of his body, all the better. Depending on your position you may be able to rub his back or legs, or you may be able to give him a handjob at the same time. Be aware that many men lose their erections when they are penetrated anally but this doesn’t mean they aren’t turned on or that they don’t want to be touched more. In terms of the kind of touch, experiment with everything from rubbing and massage to running your fingernails along his skin to slapping.

Experiment With Different Positions

Despite the long association of the rear-entry position with anal sex, there are many sex positions that work equally well for anal sex or pegging. Each position has its benefits and drawbacks, so let your physical comfort be your guide, but try out a few different ones to see which positions give you the flexibility to move how you want.

If you’d like to see a pegging video we highly recommend Bend Over Boyfriend from Fatale Media. If you’re more of a reader, check out the Adventurous Couples Guide to Strap-On Sex.