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Dr Bears Beginners Guide to Pegging - Dr. Bear Inc

Dr Bears Beginners Guide to Pegging

What is Pegging & Why Do People Do it?

Pegging typically involves a woman, trans man, or non-binary individual without a penis wearing a strap-on dildo and penetrating their partner anally. The term “pegging” is most commonly reserved to describe the act between heterosexual couples, during which the non-penis owner reverses roles and penetrates the person with a penis. 

Access to the prostate (the male G-spot) and all of the sensations that can be felt throughout the pelvic floor provide a next-level, enhanced orgasm you didn’t even know you were missing. On top of that, there are mental, functional, and interpersonal benefits that can be felt by exploring anal play.

Some of the benefits of pegging for heterosexual couples include:

  • Reaching the full potential of one’s orgasms. Prostate orgasms are powerful and can often be felt throughout the body.
  • Becoming closer with your partner and adding new dimensions to your relationships.
  • Learning to be submissive or dominating in submissive positions is typically unnatural and quite difficult to achieve, but when you can master these sensations, it opens the door to new relationship dynamics.
  • Your pelvic floor will thank you. To be able to learn and experience full relaxation during pegging can actually benefit normal defecation and heavy lifting techniques during exercise. 
  • When you’re able to control the anal muscles and decrease the local pressures, hemorrhoids for many people will resolve or diminish in severity. 
  • By being on the receiving end of penetration, you will gain a new level of appreciation and learn what it takes to receive, regardless of the orifice. Suddenly, you become aware and more attuned to what works, what doesn’t, how important open lines of communication are, etc. It’s this kind of experience that will benefit everything you do in the bedroom.

How to Prepare for Pegging

Pegging is no different than any other type of anal play. It all starts with speaking with your partner(s) and getting consent. If all parties agree, then you’ll actually want to start practicing weeks in advance. While it may seem like overkill, I first recommend anal dilating over 4-6 weeks to gradually work the tissues and muscles in the anal canal. When you have a thorough understanding of preparation, play, and aftercare, you’ll be setting yourself up for the ride of your life. Later on, we’ll go through my anal dilation protocol.

Talking about it with your partner

So, you want to explore pegging and anal play with your partner? Before you start, you may feel like you have to endure an awkward conversation with your partner(s). The good news is that it doesn’t have to be awkward. In fact, the more open and honest you are, the better chance you’ll have at actually enjoying it when you finally try it. 

We always find that the happiest couples and the ones who have the best sex are the ones who maintain open lines of communication, regularly sharing their wants, needs, and desires without fear of judgment. Try sharing with your partner(s) why you’re interested in trying pegging and anal play, perhaps including the benefits of stimulating the p-spot, and that you want to try it with them because you trust them and would like to add another activity to your sexual repertoire or gain another level of intimacy with them. 

If you’d like to start introducing the idea of anal play to your partner(s), but aren’t sure where to begin. Try asking some of the following questions to break the ice:

  • What are your feelings about anal sex or anal play?
  • Is anal play something you’re curious about or enjoy doing on your own?
  • How comfortable are you with trying out anal penetration or anal play?
  • How do you feel about pegging? What do you know about it?
  • Is anal play or pegging something we can explore further and try if and when we’re ready to consent?

Getting the right materials

When it comes to pegging, you can never have too much lube. During anal play, you and your partner(s) should have the necessary equipment handy to make sure that it’s pleasurable for all parties involved. Of course, with all the toys and other materials to choose from, gathering the right equipment is easier said than done. If this is your and your partner’s first rodeo, consider learning about how to use anal toys before you get started.

Generally, your pegging starter kit will consist of three components: a harness, a dildo, and a generous amount of lube. Harnesses are usually either underwear-style or strap-on style; they both serve the same purpose, and which one you choose is totally up to which one you find more comfortable (and sexy).

Next, you’ll want to choose a dildo – this is probably best left up to the party on the receiving end. There are many different dildos to choose from and enjoy – just make sure to find one that’s compatible with silicone-based lube. Silicone-based lube is our preference because it works best for anal, thanks to its slickness and endurance. Also, be realistic about size and make sure you find one that you or your partner(s) will be able to handle.

And again, use plenty of lube. Seriously, there’s no such thing as too much. You’ll want to apply it to both the dildo and the anus and keep reapplying throughout. 

Safety precautions

The key is understanding both the anal and pelvic floor anatomy and the functionality/motility of both. The inside of the anus and all of its surrounding structures are like an accordion instrument. The goal is to get the skin to accommodate and the muscles to fully relax. It takes time to orchestrate both correctly. 

    1. Foreplay: Don’t underestimate the power of foreplay. Anal sex can be a lot to handle the first time (or any time), so, taking the time to explore each others’ bodies, without penetration, is a great way to warm up and relax the mind and body. While it’s not for everyone, rimming or analingus is a common form of foreplay because it does such a great job of relaxing the sphincters. Other people enjoy fingering because it’s a stepping stone to larger toys used for pegging. If you choose to do finger play, please just be sure your nails are cut (and there are no jagged edges), clean, and slathered with lube. 

    1. Condoms: For pegging, because you’re using toys rather than an actual penis, condoms aren’t necessary, unless you plan on using the same strap-on for multiple partners or you’re switching back-and-forth between anal and vaginal play. If so, please be sure to use a new condom for each new person or new hole, or thoroughly clean off your toy if you’re not using condoms. 

    1. Lube: Once you’re ready to peg, probably one of the most important things straight couples may not think about is lube. Because the anus doesn’t self-lubricate (unlike the vagina), you’ll need copious amounts of lube for any kind of anal play. I recommend silicone lube due to its lubricity and endurance. Another great tool is a lube shooter or lube applicator, which is like a syringe that you fill up with lube and then insert into your anal canal. The benefit of using something like this is that it ensures thorough dispersion of lube throughout the entire anal canal. Oftentimes, lube doesn’t get deep enough, which can cause discomfort, and sometimes injury.

    1. Communication: Communication is super important. Be honest with your partner(s) about what feels good, what doesn’t, and whether or not you’re experiencing any pain or discomfort. It’s okay to speak up and say you’d like a break or to stop altogether. There’s no shame in calling it quits if you’re just not having fun. On that note, you might want to have a safe word to let your partner(s) know you’re done. 

  1. Start slow: Lastly, start slow and let the receiving partner have all the control, at least to begin with. I always recommend newbies start out riding the top. This allows the one receiving penetration (the bottom) to control the depth and speed of penetration, as well as direct eye contact, which helps with facial cues of how you’re feeling. Once the bottom feels comfortable and fully relaxed, then you can switch things up with different positions, speeds, and depths. 

Aftercare

Aftercare consists of two things: physical and mental.

After you play, I recommend suppositories (like ones with cocoa butter), as well as an anal exfoliant and a soothing cream, like the one by Future Method. These products provide proper hydration, nourishment, and soothing effects of the local tissue, and the scrub helps to remove any residual lube or bodily excrements post-play.

One thing to keep in mind is that for each day you practice dilating and/or pegging, some days we need to do contractions. Whether that’s at-home kegels or squats at the gym, just like our biceps and triceps, they need both stretching and contracting. The anal muscles are no different. We want them to be able to open fully when we want them to and close completely when we are finished. 

Mentally, checking in with your partner(s) is a great way to see how things went – what did you like, what didn’t you like, and where you can improve next time. I know that sounds like homework, but if all parties are honest, it can help nurture your relationship and provide a better experience in the future. If this was your first foray into anal sex and pegging, you may find that you don’t like it after all, or that your strap-on was too big, you’d like more foreplay, etc. It’s not a time for judgment, but rather a heart-to-heart about the experience. And, in the end, who wouldn’t want to have better sex?

Pegging: How To

You’ve made it this far. There are only two things left before the big debut: anal training with anal dilators, and picking the right strap-on toy or device.

Pegging and anal sex aren’t something that someone can just decide one day to try. It takes patience and practice in order to reduce your risk of injury and maximize your chance of receiving pleasure from pegging. Through this process, you will get to know your anatomy and body more intimately (literally and figuratively). You can then use what you learned during self-play with your partner(s)during pegging.

There are various options for anal toys to use during pegging – a strap-on that’s in the form of a dildo, prostate toy, or vibrator – and each of them has different shapes and sizes. When the receiving partner has a prostate, I would recommend using a prostate toy, as these are designed specifically for stimulating the prostate, which is the G-spot equivalent. The anus has so many nerve endings, which all deliver satisfying sensations up and down your spine, but the prostate, or P-spot, will provide the most pleasure and these toys take the guesswork out of finding the right angle for proper stimulation. Dildos can be found in straight or curved designs and are the most universal for pegging and self-pleasure. Vibrators are another fun option as the sensations they provide will no doubt make your eyes roll back in ecstasy. For some people, they may be too intense, especially for first-timers. They offer ones with various types of vibrations – speeds, intensities, and cadences – to help meet everyone’s needs.

Once you have trained yourself and chosen your pegging device of choice, it’s time to pick out a position that’s right for you and your partner. We recommend starting with cowboy, cowgirl, or cowpoke if you’re new to pegging, but there are many other positions that are comfortable for both partners. Learn more about what they are below!

Best Pegging Positions for Beginners

Cowboy, Cowgirl, or Cowpoke

This is the position you'll want to start with if you're new to pegging. Since this position gives the power back to the receiving partner, they can control things like the angle, depth, and speed at which they receive it. The position itself is straightforward; it involves the receiving partner hopping atop the giving partner and riding them.

Doggy Style

No pegging position list would be complete without doggy style. In the realm of regular (and wild) vaginal and anal sex, doggy style is a classic. While it can be challenging if the partner wearing the strap-on is at a height disadvantage (that is, shorter than their partner), it's still possible. For those of you who are vertically challenged, try having a pillow or cushion handy to kneel on to give you a few more inches (of height).

Butterfly

In the Butterfly position, the receiving party will lay on the bed (or surface of your choosing) with their legs bent at the waist and straight up. The person doing the pegging will stand at the edge of the bed with their partner's legs resting against their shoulders. In this position, the legs on the shoulders are essential because it lifts the hips upward, making the pegging possible.

Spooning

Another classic position on our list is spooning. We all know spooning as the go-to position for wake-up sex during a lazy morning, but it can be a great way to peg as well. In this position, the usual bottoming partner is typically the little spoon, so this gives them a chance to trade places. This position is also great for giving massages and providing comfort during anal play. 

Amazon

The Amazon position is a little trickier than some, so I recommend trying this one once you have some experience under your belt (or harness). In this position, the receiving partner will lie on their back with their knees pulled into their chest. This will enable the giving partner to penetrate the receiving partner from beneath. Make sure to do your stretches before taking this one for a spin!

Turtle

For people who want to get up close and personal with their partners while pegging, this position is for you. In the turtle position, the receiver kneels on the bed (or other surfaces) while using their arms to reach around their legs. The giving partner will then kneel behind them with their knees on the outside. Tip: I suggest letting the receiving partner use a pillow beneath their chest or head for comfort.

Leapfrog

The Leapfrog is another great position that's comfortable for both partners. It is similar to the Turtle; however, the receiver reaches out in front of them instead of behind their legs. The receiving party's knees are also on the outside instead of in. The Leapfrog position enables the receiving partner to adjust their hip height to make entry easier.

Lap Dance

If the receiving partner has longer legs, the Lap Dance position might be easier for them as it lets them rest their feet on the floor. In this position, the receiving partner will straddle the giver with their back toward them. The actual Lap Dance itself is totally optional, but this position is a fun way to incorporate foreplay before getting to the main event.

Sandwich

The Sandwich pegging position was made for anal sex. Seriously, it's perfect for it. In this position, the receiving partner lies back and positions their knees up to their chest. Next, the giver will slide between their partner's legs with the strap-on and grab the back of their thighs. The giver can use their grip on their partner's thighs to help them control the tempo while thrusting. Plus, the eye contact makes it sexy and intimate!

Missionary

You might already know about good ol’ Missionary, but did you know it could be used in pegging too? The only changes needed to make it work for pegging include having the receiving partner lift their legs and bend their knees so the giver can scoot closer during the action.

Conclusion

Now that you know how to prepare and what to do, it’s time for you and your partner to have a serious conversation and see if pegging is right for you. For many couples, pegging can be a great way to change the power dynamic and switch things up, but you must prepare. Ensure you have the proper equipment and take the time to prepare yourself to avoid any mishaps during anal play.

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