To Peg or Not to Peg: That is the Question...

May 03, 2016 1 Comment

To Peg or Not to Peg: That is the Question...-Couples Playthings

Pegging is growing more and more popular amongst couples. If you’re not familiar with pegging, we’ll take a quick moment to explain. Simply put, pegging is the sexual practice between couples where a woman anally penetrates a man through the use of wearing a strap-on. In our opinion, pegging is definitely not a spontaneous act nor do we recommend it to anyone with little, or no experience, to anal play. Pegging can be a very enjoyable for both partners if done correctly. If you’ve already read our article The “A” Word!, you’ll be very familiar with the benefits of anal play. Similar to having anal sex with a woman, there are steps that you should take in order to provide the best experience possible. We’d like to break these steps down in greater detail, and give some pointers, to ensure that you and your partner are well prepared. We can attest, it’s a lot of fun!


If you’ve read any of our other articles, you’ll probably notice by now that communication is extremely important to us. It has helped our relationship tremendously and we strongly recommend open communication in your relationship. As for pegging, it’s always a good idea to speak with each other about your feelings, thoughts and especially any hesitation that you or your partner may have. For us, it was Liam’s idea to try pegging. Since we already had some experience and great fun with anal play, he was ready to move to the next step and try full-penetration. For some heterosexual men, there is often hesitation in partaking in pegging. One of the common questions that we’ve heard is: “If I like it, does that make me gay?” The answer to that question is NO! Now please bear with us as we are not trying to offend anyone in the gay community. In fact, we fully support our gay community and we absolutely love and appreciate all of our gay friends and subscribers. To elaborate more on this question, the physical pleasure derived from pegging does not make a man gay. A man having physical and emotional attraction for another man is what helps define someone as gay.

Build Trust

When we first developed curiosity for anal play, we were both very hesitant. Neither of us had any experience. With several open discussions, we finally agreed to give it a try. We first tried anal play on each other with some light stimulation using fingers and very small toys. Both of us ended up enjoying anal play immensely. When it came to full penetrative anal sex, Liam said he would also try it and be on the receiving end first. Liam thought if he was on the receiving end, he’d also learn to be a better ‘giver’ to ensure that Robin’s first time would be as enjoyable as possible. Trust was immediately built between us since Liam was willing and open to receiving. Upon communicating and building some trust, we knew it was right for us and we moved onto the next step: finding the right ‘tools’ to for pegging.

Finding the Right Gear

The three key things for a successful, and enjoyable, pegging experience include: a comfortable harness, dildo, and LOTS of lube.

  • Harness selection: Choosing a comfortable harness can sometimes be tough. You want to ensure that the harness fits snug and does not slip around too much. Harnesses come in various materials, sizes, and features. Upon purchasing our pegging gear, we had a little extra money to spend so we purchased the Joque by SpareParts HardWear. We assumed that we would like pegging therefore we spent a little more coin and the Joque had some very appealing features that would allow us to advance in our pegging play. Robin was very curious about using harness-free dildos and vibrators and the Joque accommodates those types of toys nicely. If you are on a budget, there are some great starter kits that include both a harness and dildo. One item that we have tested is the Bend Over Beginner Kit made by Tantus. This kit includes a harness, bullet vibe, and two dildos: one small and the other a more intermediate size. Couples Playthings offers a wide variety of strap-on harnesses so feel free to check them out. Also, there are harnesses that will allow the wearer to have some stimulation as well. We recommend a remote control bullet vibe, like the Lyla 2, as it can add more pleasure leading to a more enjoyable experience.
  • Dildo selection: We recommend starting with a small dildo and working your way up. When possible, try to find a dildo that has a slight curve at the tip. Having a slight curve allows for greater stimulation of the prostate which can lead to an amazingly intense orgasm. It’s always a good idea to first select a smooth toy versus those with a lot of texture to avoid overstimulation. As you develop more experience with pegging, you can advance to larger, and more textured, dildos. Some great recommendations on a starter dildo include: Silk Small, Silk Medium, and Sport which are all made by Tantus. Feel free to browse the wide selection of strap-on dildos & vibrators offered by Couples Playthings.
  • Lube selection: Due largely on the fact that the anus and rectum lack the ability to produce natural lubrication, it is a MUST to use copious amounts of lube when pegging…or any type of anal play. We strongly recommend using a water-based lube, especially if a silicone dildo is being used. Using silicone-based lubes with a silicone toy can damage the dildo’s silicone material. Water-based lubes can be absorbed into the skin rather quickly so re-application may be necessary. There are many lubes that are designed specifically for anal play as they are slightly thicker which allows for more ‘padding’ during anal sex. Two wonderful lubes that we use are Sliquid Naturals Sassy and JO H2O Anal.

Once you’ve purchased your pegging gear and have tested the harnesses’ fit, it’s now time to have some fun! Before our first time, we were both really nervous. So, as always, we had a brief discussion before beginning. We mentally prepared ourselves and Liam made sure he was physically prepared. Before proceeding with anal penetration, we recommend going to the bathroom to empty the bowels, or using an enema a couple of hours before play. Some people can get grossed out at the sight of, or making contact with, poop. Rest assured, at some point it will probably happen and it’s best not to make a big deal of it. Remember, if you’re playing in poop’s home, you’re bound to meet poop. Once all mental and physical preparations have been completed…time to get busy!

We’ve included some tips below to help your first time experience to be as enjoyable as possible. Pegging is very fun, exciting and enjoyable and we want your experience to be as fun as it is for us.

Find the right position: We recommend first-timers to either try cowboy, doggy-style, face-down or missionary.

  • Cowboy (the same as cowgirl) is when the woman lies flat on her back. The man straddles the woman’s hips and slides down on the dildo. For beginners, this can allow for the man to have better control of depth and movements.
  • Doggy-style is also very popular. With doggy-style, the man simply rests on all fours allowing the woman to enter from behind. This position can be modified by having the man’s legs spread open or kept closed. It can also be modified by keeping the butt up in the air, but the man’s head, elbows and arms can be lowered towards the bed. We recommend doggy-style to women who love watching penetration as it happens.
  • Face-down is also a great option. The man simply lies on his stomach and the woman straddles, or spreads, the man’s legs, and enters from behind. This position gives all the control to the woman. Many people, including ourselves, often keep the man’s backside propped up with a pillow. Or, the Ramp and Wedge made by Liberator are also great props.
  • Modified Missionary happens to be one of our favorite positions. With the man lying on his back, the woman lays on top or enters from a kneeling position. With the woman kneeling, the man can either lift his legs and feet in the air, or, rest them on the woman’s shoulders. We especially like this position because we can make eye-to-eye contact and we love watching and reading each other’s facial expressions. Additionally, the man’s penis is accessible allowing for some stroking action while simultaneously being penetrated. 

Apply plenty of lube: Be sure to apply lots of lube directly to the anus and to the dildo before beginning. For those that want to ensure that the rectum is well-prepared, you can also use a lube applicator. A lube applicator allows for plenty of lube to be applied deep inside the anal canal. This may allow for extended play without the need to reapply lube. As stated earlier, water-based lubes can sometimes dry quickly so keep your lube nearby.

Relax & take it slow: Once lube has been applied generously, the time has finally arrived…penetration! When receiving, be sure to control your breathing. Take deep relaxing breaths as it will help to keep you calm. Not only does breathing help calm you, but it also helps relax the muscles in the anus allowing for easier penetration. Once the dildo has made its way in, take a moment to stop all movement. By doing so, this will allow for the receiver, and the muscles in the anal canal, to get used to the fullness of the dildo. Once comfortable, start moving in and out slowly and work your way up to whatever is comfortable for both of you.

Communicate and make eye contact: To make the best experience possible, be sure to communicate during your play. If you want it faster or slower, tell your partner. If you want it hard…say to your partner, “give it to me!” Also, be sure to communicate by complementing each other during play. If you are receiving, let your partner know that she’s sexy and she’s really good at pleasing you. If you are the giver, tell your partner how hot he is and how much fun you are having. Have fun, talk dirty or whatever the two of you are into. For positions that allow eye-to-eye contact, please look at each other as often as possible. From our own experience, we’ve had some very meaningful experiences gazing into each other’s eyes. It can really add some spark to your play time. Additionally, when able to look at each other, play close attention to facial expressions. This can be a great indicator for knowing if you or your partner is enjoying what’s happening. Lastly, and most important, if you feel pain…stop immediately! Communicate to your partner what you are feeling and completely stop your play, or, find a new position or dildo that will lead to a more comfortable and enjoyable experience.

When play is over: Be sure to thoroughly clean your harness and dildo when finished. The last thing you want is to have bacteria crawling all over your new pegging gear. Without proper cleaning, you and your partner are at a greater risk of infection. Also, have a nice follow-up conversation afterwards. Discuss what you liked and what you didn’t. Talk about future play and if both of you want to continue down the pegging path. Your first time might not be perfect, but with good communication, the two of you will be able to find ways to make future pegging play more fun and enjoyable.


We hope you have enjoyed this post. Please feel free to comment if you have any questions, concerns or information you'd like to share. Be sure to check back for more blogs and product reviews or subscribe to our newsletter for automatic updates. We can also be reached directly via email at

Thanks again,
Robin & Liam

1 Response


April 19, 2017

Lots of good advice on this increasingly popular practice! Couple of personal observations: starting with a slim dildo (Tantus offer such a thing) helps remove the intimidation factor. Also, for lube my preference is Sliquid Silk, as recommended by Ruby Ryder, the leading authority on pegging. As mentioned, a “debriefing” afterwards is wonderful for all sexual activity. Freely discuss what worked and what didn’t!

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