Pegging

Pegging For Beginners

Pegging is new, pegging is exciting, pegging is scary. Read my previous blog about how pegging feels to a woman.

In his newly discovered and highly emotionally aware state, he will likely be very open to trying new things especially things of a sexual nature. This might be a great opportunity to try pegging which will only serve to make you feel empowered and make him feel somewhat more emasculated. This is a great way to assert your relationship dominance and help him understand what it is like for us, being on the receiving end. There is no doubt that a pegging session or two will make him a better and more considerate lover. We resort to pegging at least once a week and I always initiate. Typically I will go into the night stand, grab my strap-on and tell him to roll onto his tummy. I don’t like to overthink it by asking him to do an enema etc. By turning it into an ordeal, it becomes less impactful and less dominant of an act.

You want your tone to come off as “Roll over, I want your ass!” instead of “Tonight I’d like to peg you so please make sure that you clean yourself out after your shower and get dressed for bed”. Pegging loses all of it’s inherent dominance if you don’t make it spontaneous and immediate. One thing I’ve found is that this allows me to be rougher and less delicate with him. I like holding his arm down, his legs back, tell him what position I want, tell him to push back on it when I get tired. Make sure that you be dominant and assert yourself, don’t ask him so many questions about what he wants, how he likes it. He will tell you if he doesn’t like something. I also really enjoy having him suck on my strap-on before we have a session. I find that the the act of him looking up at me while I reassure him and instruct him how best to suck my rubber penis is very arousing and further empowers me and turns me on for the act that is to come. 

If anything in this blog will get him out of his comfort zone, this one is going to be it. Pegging is very exciting for both of you and it requires a great deal of trust from both sides. I can’t write a blog about pegging without including the wonderful Ruby Ryder. Ruby is the absolute best source of information on pegging and truly the best source of sex positive information about the amazing world of pegging. Ruby Ryder has an incredible podcast including this one specifically for the ladies. I highly recommend that you stop and listen to that podcast before you go any further. Ruby also has a website that answers questions and dispels myths about pegging at pegging 101. Also look around for the right “apparatus” because it is important to feel sexy while you are doing such a sexy activity. I’ve found a couple that are incredibly comfortable and aren’t your typical “Strap On Harness”.

I reached out to Ruby for her thoughts on pegging and this is what she said:

Pegging allows couples to experience sex from the opposite side of the bed, where profound adventures await. The role reversal often results in a deeper intimacy through better understanding of their partner’s usual role.


At its essence, pegging offers men an opportunity to revel in their sweet, soft parts; the parts that society typically doesn’t want them to express. They get to take a break from the expectations of being strong, in charge, and in control. Vulnerability and receiving are the order of the day. If that’s not enough, consider that extra-powerful orgasms, multiple orgasms, whole-body orgasms, and prostate health are all potential benefits of pegging, too.


Pegging offers women the chance to take the reins and run the fuck, be the active and in-control partner. Some women find an inner dominance and enthusiastically embrace it. Other women treasure interacting with their partner’s soft, vulnerable parts; the parts they rarely get to see. And while many people think the pleasure flows in only in one direction, and women don’t get much out of pegging, there are exciting equipment choices that can even out the orgasm playing ground. Pegging can be a win-win sexual adventure!

-Ruby Ryder

When we have orgasms, most of us can have vaginal orgasms and clitoral orgasms. Neither type of orgasm is better (in my opinion) but they are entirely different and feel exquisitely different. Men can have orgasms from their penis and also from their prostate but very few men are comfortable enough with themselves to ever try the prostate orgasm. Men that have experienced a prostate orgasm typically describe it as much more intense than the penis orgasm.

Most men will take some time to warm up to the idea of being vulnerable to a woman so this may take some convincing. On the flip side, you may find that your man is ready to go the moment that it comes up in conversation. Your man will need to learn to relax enough to allow you to penetrate him. Women are very familiar with being penetrated during sex but men are not used to that feeling. He will likely go through a roller coaster of emotions from the experience. Once things are said and done, he will likely want your reassurance and will want to talk about the emotions that came up. The submissive feelings typically make him very conversational for about a week after pegging. A man, wanting to talk to you about emotions? I know, right!

The whole thing can be exciting and downright overwhelming so remember to ease into it. Start with using a small toy and work your way up to full blown strap-on play. Don’t try to do everything in one night. Take things slow and use pegging to connect with each other at a deeper (pun intended) level. If he wears a cage, this is a fun sexual experience that you can do without him needing to remove it. When locked, he will have an enormous amount of sexual energy which you’ve experienced first hand with all of the unsolicited massages and gentle touching. Pegging is an excellent outlet for that sexual energy and it plays right into the power dynamic that you are creating for your relationship. Pegging and the submissive emotions that it will undoubtedly bring to the surface will only strengthen his trust for you and the authority that he perceives in you.

Now that we indulge in pegging regularly, I like to set expectations and build anticipation by setting my harness out on the nightstand before getting ready for bed. Since I set the tone of the sexual activity in our relationship, I like to give him plenty of notice in some aspects. This gives him time to ensure that he is clean and ready for the evening’s activities. An anxious or rushed pegging experience isn’t going to be a very successful one.

Talk about it. Set expectations. Set boundaries. Pegging can be one of the most exciting and arousing sexual experiences that either of you has experienced. Make sure that neither of you violates the boundaries that you set forth or pegging may be one of the worst sexual experiences. Remember that as with nearly every aspect of your relationship, communication is key! With any luck you will learn things about yourself, he will learn things about himself and the two of you will make love and connect in ways you never imagined.

Interested in reading more? Check out Pegging My Boyfriend For the First Time on peggingtoys.com. If you like any of their products, remember to use the code “EVOLVED” and get 10% off.

8 thoughts on “Pegging For Beginners

  1. Excellent write up! I wanted to add that as a guy my mindset on this topic changed after my first prostate orgasm. It took practice and time to achieve that first orgasm. I think it would be hard to have the first one from pegging. I discovered it solo with a prostate massager and about 45 minutes of relaxation. The more you have, the more you learn about your body and how to help it get there through relaxation, breathing, and muscle control and eventually you get to a point where you can have one during pegging. So if a lady finds her man is resistant to pegging, a prostate massager might help him get over his hang ups and discover a whole new world of pleasure in the last place he would think to look.

    1. Do you have any suggestions or articles about how a man can experience a prostate orgasm? Kevin hasn’t been able to experience one and I’m not equipped to tell him how to get there.

  2. I think the angle of penetration has a lot to do with it. It’s very difficult using just a harness because the angle is oftentimes more straight ahead rather than downward. That can be painful. I’m taller with longer legs than my gf. Our best results are when she holds it and adjusts the angle just right. Usually starts higher up and pointing downward to where it’s hitting the prostate more firmly. Not too steep and not too firm…takes a lot of feedback and adjustment for us.

  3. So I learned how to do it year ago with the Aneros prostate massager and their website. I just looked and did not see the instruction that was there earlier. I did some searching and found this –> http://wiki.malegspot.com/index.php?title=Getting_Started#Let.27s_have_Fun.21

    I think solo is the best way to learn this and once you have it down bring in your partner. Otherwise they will get board while you are trying to figure this out. It will likely not happen the first attempt, but keep trying and you will not be disappointed.

    I would recommend the Aneros Helix Syn if “butt stuff” is new to you or the Progasm Jr if you are comfortable with pegging. If you do “butt stuff” on the reg then go for the Progasm. In my experience bigger is not better and can make it hard to relax to the point you can’t trigger p-waves. There is a lot of detail in the link above, but in short it works like this for me.

    1) Get comfy on your back and apply lube to yourself and the massager
    2) Make sure you insert the massager so that it pushes against the prostate rather than pushing away.
    3) Relax and breath deeply until you no longer feel the massager inside you. This can take a while. At least 20 minutes for me. Don’t short cut this step, as it is critical. Read a book if you get bored.
    4) So now you are bored and can’t feel the massager. Now you can edge yourself a little to get aroused, but for the most part keep your hands off your penis from this point forward.
    5) Now flex your pelvic muscles and hold for as long as you can while taking full breaths in and full breaths out. Keep repeating this for 5 minutes.
    6) Now start timing your pelvic muscle contractions with your slow deep breathing. Contract as you breath in and relax as you breath out. Do this again for about 5 minutes. Nice slow, deep breaths.
    7) It will start to feel good and you will start leak precum. This is prostate milking. You will feel like you have to pee, and that is the queue to start shortening your breath to be very rapid. Keep your pelvic muscle contractions in sync with your rapid breathing. Contract as you breath in and relax as you breath out. Fast, but not to the point you are hyper ventilating.
    8) Eventually you start to feel waves of pleasure from your head to toes called p-waves. I swear I can even hear it in my ears like a low buzz getting louder and quieter. At this point keep up with the rapid breathing and contractions to keep layering the waves and building up the orgasm. The waves become the orgasm, and keep getting more intense. This bliss can last several minutes, and if you lose it just start back with the slow deep breaths/contractions and work your way backup to short rapid breaths/contractions. This can go on an on with orgasm after orgasm until you are too exhausted to continue.

    Once you have this down and can repeat it, then your girlfriend can join you and use the come hither or push button finger technique. The man sets the pace with the breathing and contractions and she times her stimulation to match.

    This works for me to get a Super O, and I hope it works for others as well. Once your man has had one, there is no putting this back in the box and forgetting about it.

    1. I wanted to add that on the contractions you want to start off light and resist the urge for strong contractions until the end of the session. The stronger the contraction the more pressure is applied to the prostate. You want the contraction to feel full and pleasurable and let the pleasure slowly build with stronger contractions, and if you feel pressure and mild pain you are contracting to hard to fast. Give yourself plenty of time adjust to stronger contractions. Any feeling of pain or discomfort or anything that takes you from that relaxed state and you will likely not get to a prostate orgasm. From other instructions on the internet, I would discard this as mystical nonsense if I had not experienced it. The instructions from others have slightly different approaches, but they all seem consistent on some combination and order of relaxation, breathing, and pelvic contractions, so if my steps don’t work play around with the breathing and contractions. Just go slow and don’t try to force it.

      1. I also wanted to add that for me I have never ejaculated from a prostate orgasm. There is a bit of cum that leaks from the prostate milking that occurs, but not your typical ejaculation. It is great for getting pleasure when caged without the drop or refectory period that follows a traditional orgasm.

        And on the topic of pegging, I was watching a new Netflix show called the Russian Doll and there was a scene where there was an orgy pile of people waking up and one guy stood up with a strap-on attached reversed with the dildo pointing out of his butt like a horn. I burst out laughing, because only a dominant woman would have thought to write that into the script.

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