Blog · Pegging & Role Reversal

Pegging Proficiently

The physical side of pegging is pretty simple, I spelled it out in this blog about pegging for beginners. Girl puts on strap-on harness, boy bends over, girl puts fake willy into boy. With this blog I’d like to get into a deeper conversation about how to understand each other and the right questions to ask. If you are reading this, I’ll assume that you’ve pegged your partner at least a few times. If not, start slow and come back to this one later.

It is nowhere near that easy and over the course of the last few years we’ve learned what we like and dislike about this complex nuance to our sex lives. Together we communicate those likes and dislikes to bring a playful love to our bedroom. As with any intimate experience, pegging is a journey of understanding and communication. The physical act can build an intense connection and bring us much closer together. If done improperly, it has the potential to do the opposite.

If communication in relationships is key, communication about pegging is essential. You will even find that communication about pegging before, during and after may elicit different responses due to social stigmas. Pegging is more popular than ever and is consistently ranked as one of the most popular sexual fantasies among women.

Pegging may even be considered trendy amid today’s sexual revolution. Trendy or not, there’s still something taboo about it. Something about swapping traditional gender roles and engaging in a dominant/submissive power exchange makes pegging excessively erotic and provocative.

Reminder About Pegging

Since the strap-on itself is made of plastic or some sort of material that isn’t biologically attached to you, many women feel like pegging is something that they do for their husbands. I’ll be the first to tell you that I am psychologically aroused by pegging in a way that I am never aroused by PIV sex.

The Mental Aspect

I’ll also be the first to say that pegging is my preferred type of sex, I love the sounds, the movements the post-sex cuddles. I love how he quivers, how he relaxes, how he spasms. I love how he opens his body and makes himself vulnerable to me. Pegging isn’t something that you do for him, pegging is something that you do with him. Admittedly, the first time I tried it I wasn’t aroused but it was compelling on a psychological level. It lit a spark and completely changed my perspective on sexuality. Pegging makes you feels so powerful and in control.

For men, the other side of that coin can be difficult since he may not be prepared for sex to be such an emotional experience. In opening himself up and trusting, he may feel like he is giving something up in the process. Men can go through a roller-coaster of emotions from regretful to ashamed to belittled. This is interesting because women allow men to fuck them all the time and don’t feel so subjugated. I think this gender equalization is part of the allure of the act to me. A man opening himself up to you in such a way is an intensely powerful experience.

Shifting Perspective

Pegging is all about shifting perspective. His perspective, your perspective and the sexual dynamic of your relationship. Wear the strap-on around the house for a while. Cuddle with the him in bed while wearing the strap-on. This will clue him in to the plans that you’ve got for the evening and it helps him mentally prepare. The strap-on doesn’t always need to mean that pegging will happen. Sometimes I just want to wear the strap-on. When he sees me remove the harness to get ready for bed knowing that pegging won’t be happening, you can see the disappointment on his face. His disappointment can be exhilarating in a dark kind of way.

Pegging is an incredibly taboo act… the first couple times. Then it becomes part of your sexual arsenal and just another one of the ways that you make love and share affection with each other.

When communicating before your pegging adventure, he will probably be much less communicative. Most guys are going to be somewhat shy and reserved with answers during this time due to taboo, stigma and society’s gender rules. I personally reject those rules and the cultural script that goes along with it. Attempting to equate gender identity with a sexual act is just totally incorrect. If a couple can get pleasure and intimacy by shedding their gender’s stereotypical roles to let the woman drive from time to time. So gender roles aside, conversation before an experience will need to be a bit more discrete and conversational since those gender role walls are up.

So let’s get strapped up and into the action. Before we start, sometimes I will instruct him to get on his knees to suck my dildo to “get it ready”. I obviously don’t physically feel anything during this blowjob but the emotional side of a blowjob is not to be underrated. Standing, while he kneels before you and you insert yourself into him. This isn’t a feeling that is easily dismissed and I can honestly understand the mental appeal of a blowjob. Beginners will choke or tense up, talk him through the blowjob and remind him to relax and swallow more of it. Push the top of his head down on it once in a while to make him gag, even if just a little. There is really nothing like uttering those three magical words “suck my dick”, it is truly empowering to see him get on his knees and comply.

When it comes to oral, remember that it is important that you thoroughly clean your toys before and after each experience. If you are ever in doubt, you can always put a condom on it.

When preparing to give him a pounding, I like to make him wait. I’ll take an extra few minutes getting ready and will instruct him to lie in position while he waits. I may spend extra time trying on a few different harnesses and dildos, modeling them in the mirror. During our time getting ready, he can be over the side of the bed or on his back or holding his legs. Either way, it is important to me that he can watch me get ready for him. This allows him to get into the right head space for our playtime and helps him realize that I am taking our time seriously, making him important to me.

We don’t do spankings and punishment really anymore but I do sometimes spank him prior to pegging especially if I feel like he might be distracted by other thoughts. When we’ve got things on our mind, sometimes an external stimuli is all it takes to snap us into the “here and now”. In this case, the physical feeling itself helps get him into the head space. A freshly tender bum only increase the sensations that he feels.

I do sometimes tell/tease Kevin by telling him that he is going to be my “girlfriend” or “bitch” tonight. This is purely sexual play and I imply this as him taking the role of being penetrated and not penetrating me. This is as far as our discussion of feminization goes, I don’t actually want to see him dress in women’s clothing. Our discussion of roles is purely related to the stereotypical physical act of who is taking the more passive sexual role. My implication is also not intended to be derogatory to women, it is just my way of trying to make him visualize being bent over the side of the bed with his head buried in a pillow. Yeah, you’ve got that visual image now too.

On the flip side, I am not interested in replicating the masculinity that comes along with penetration. I love my feminine form and I think a snug fitting strap-on harness can be an extremely feminine accessory. I’ve certainly had Kevin take pictures of me and I’ve absolutely admired my profile in the mirror.

That passive sexual role is interesting and he may not know what to do with himself at first. In the next section I will get into communication. In the dominant/male sexual role, he hasn’t needed to communicate to you much. As he will undoubtedly find, the passive role isn’t simply a subordinate and receptive force if he wants something, he needs to communicate it.

Initiating

If you find that your guy simply isn’t very good at communicating what he wants, he may be ashamed to admit that he actually enjoys pegging. He may be ashamed to admit this to you and he may be ashamed to admit it to himself. Reassure him that enjoying himself is completely fine and you want him to enjoy himself. I find that it works well to ask him to tell me when he wants to be pegged rather than initiating it myself every-time.

When he is forced to initiate, he is admitting to you and to himself that he wants you to stimulate him in this way and he accepts you in the sexually dominant position. You can even come out and ask him to initiate pegging more frequently. The initiating can be a playful extension of your role reversal.

Here are some ideas to get you started:

  • I want you to fuck me tonight.
    This one gets right to the point.
  • Can I be the girl next time we make love?
    I like this one because it admits the desire to be submissive and he is requesting to be penetrated instead of doing the penetrating. The gender reference is kind of kinky too.
  • I’m feeling like being a slutty boyfriend for you. Busy later?
    Husband, boyfriend, you get the point.
  • Do you feel like using your strap-on later?
    You can also come up with a code or pet name for your strap-on. We have pinky & big blue but you can pick your own.

Some of these may sound submissive or even feminine and that may feel uncomfortable for him, perhaps both of you. It will come more naturally with time, practice makes perfect. Make sure your responses are positive, encouraging and enthusiastic. Even if your answer is “no” or “not tonight”, make it playful and fun.

It is also important to initiate things with him in a way that will make him feel sexy and confident. Remember that the sexually submissive role is probably new to him. Notice that all of my advances towards him assume that he will be interested. Presupposing that he will be interested is more assertive and will be seen as a mixture of a compliment and a sexual advance.

  • Your butt looks great in those jeans. I know what I’ll be doing with it later.
  • I have a sexy idea that doesn’t involve unlocking you.
  • I keep having a fantasy of you bent over the bed tonight. What do you think?
  • Gently grab him by the hips and make thrusting motion. (my favorite).

Encouraging His Communication

I’ve found that I get the most honest answers during the experience and asking certain questions can be arousing as well since they can be asked more forcefully and dominant. I usually like to be verbal when I fuck him and it encourages him to be verbal as well. I don’t accept one word or yes or no answers when I ask these sorts of questions and he knows it. If he isn’t responding to your questions or isn’t giving satisfactory responses, stop the session until he responds properly. This will ensure that he understands your expectations next time.

Here are some examples:

  • I want to hear you moan when it goes in
    This sets a tone that I want him to be free with his noises and as an extension, that I want him to be comfortable and open with his emotions.
  • Tell me how it feels
    Regardless of the response, this question encourages him to be present and actually think about how his body feels. Responses to this question can give you a better understanding of how properly sized your “instrument” is.
  • Do you want more or are you ready to stop?
    This works well for guys who are having trouble admitting that they enjoy pegging.
  • Do you like it when I ____________?
    Describe something that you are doing to see if he likes it. This helps to open the doors of communication especially when he has trouble admitting that he enjoys it in the first place. After sex you can also ask him his favorite position.
  • When I pull it out, wiggle your hips and tell me to put it back in
    This may seem silly but it has an emotional impact on both of us. I like to tease him with it, pulling it out a few times during our experience. This give me an opportunity to stand up straight and rest for a moment. I also like hearing him and seeing him wanting me in such a carnal way.
  • Name calling
    I am usually not a big fan of name calling but it works for us. Words like “little bitch” or “slut” work well for us. He reacts and we both enjoy the extension of the role reversal. These can be either outright name calling or they can be questions like “do you like being my little slut?” or “how does it feel to be my little bitch?” Name calling is also fun to combine with some of the others in this list.

Communicate With Him

It’s not all about his communication to you. You can communicate to him as well. Here are some examples:

  • Say something when you first slide into him.
    This can be as simple as a sigh of relief or this can be as a guttural “oh yes”. This makes him feel good and shows him that you are as excited in this experience as he is.
  • Oh yeah, that’s it
    Using positive words like this help validate him and associate positivity with your experience together.
  • Remind him to relax
    Verbally remind him to take deep breaths and relax. Slide your hands down his back, put your weight on the small of his back to push his butt up and toward you. If his body is tensed up, he won’t be enjoying himself and isn’t in the right head space.
  • I love when…
    Pick something that you like it and describe it. I love it when you arch your back. I love it when you push yourself back on me. I love it when your body goes limp. Feel free to include a compliment or words of affirmation when doing this – Your hips are so sexy, I love holding them when I fuck you.
  • Sexual commands
    Put your legs up, roll over, put your head in the pillow, get on your side. Very brief commands instructing the action. Rather than receiving those commands, give them. Are your legs getting tired? Change the position and dictate that he make changes to his position to accommodate whatever is coming next.
  • Threaten to stop
    I’m going to stop if you don’t push back on it. I want to fee like you are into it as much as I am.
  • Remind him why
    Give him a verbal reminder of why you enjoy pegging him. If you use pegging as a punishment, remind him of his transgressions. If you do it because you like to see his little tight booty, tell him. If you like pegging and can’t get enough, communicate that to him as well.

His Pegging Technique

There are dozens of pegging positions but our favorite is doggystyle. One of the things that took him some time was his body position. He kept wanting to arch his back like the beginner image below. The lower body position with the steep angle between the hips and lower back makes penetration easier and more pleasurable since it gives better contact with the prostate. Expert may not be possible for his body type but we try to stay conscious of the position and keep it somewhere between intermediate and advanced. If I notice his body start to arch, I correct him and push down gently on his lower back.

When doing other positions, make sure that his body language shows trust, relaxation and he is fully committed. If his body is tense, adjust his body positioning accordingly, rub his skin with your hands or stop for the evening.

For positions that allow for eye contact, you can demand that he maintain eye contact with you. Extended eye contact can make for a very sensual and connected experience together.

Your Pegging Technique

This part is important and it took us quite some time to learn the proper technique. Kev was very poor with his communication at the beginning and that made it nearly impossible for me to understand his likes and dislikes. He has gotten better but I usually have to ask very pointed questions to get worthwhile answers.

One of the biggest misconceptions that I has was with the actual fucking motion. When you are thrusting into him, use long strokes, sliding all the way in and out of his body completely with the tip of your toy coming completely out of him every once in a while. This maximizes the friction on his prostate and nerve endings. If you simply slide it into him and gyrate your body, he can feel you on him but the pegging feelings are minimal since the majority of nerve endings are in the first inch or two of his bottom and there is virtually no contact with his prostate. After you begin, his bum will adjust to the size of the toy that you are using and sliding in and out won’t be a problem.

One of the benefits of having a removable penis is the different shapes and sizes that you can try. Your guy is equipped with only one penis. Despite the fact that it might be a very nice penis, I think can all agree that sometimes it might be nice to feel something just a little bit different.

With pegging, you have the benefit of trying different shapes and sizes to see how he reacts. Longer, wider, thinner, try them all to see which ones invoke the best reaction. Once you find a dildo size that works well, you don’t need to keep going larger. In fact, a six inch dildo with a nicely defined head is what we like best. I don’t recommend stretching the bum out too much. The anus doesn’t have the same elasticity that the vagina has so you need to go slow and gradual.

Another way to open communication is to watch some pegging porn together with him and discuss what you do and don’t like. This can be great foreplay and you can both learn some new tricks together. For bonus points, put your cock and harness on and cuddle with him while you watch your porn.

Here are a couple of our favorites:

Warming Up

Start slow, with plenty of lube slide in and out of him a few times. Wait for the lube to spread evenly and for his body to adjust to accept you inside of him. This wont take more than a minute or two and his body language will dictate when he is feeling comfortable to move more quickly.

Slow and Sensual

Pegging can be a very intimate experience if you lay on your side in bed or on the couch with his bum facing you, spooning. Wrap an arm around his stomach or chest and use that as leverage to slide in and out of him. Your bodies together will feel an incredible level of closeness.

Fast and Furious

Once you get him warmed up, you are free to move more quickly. I recommend a fast rhythmic pace. Assuming your harness fits well, grind your pelvis upwards as you thrust for a wonderful ab workout. Hold on and go for a ride but don’t get too reckless. The bum is a delicate spot and you don’t want to hurt him.

Chastity

We use chastity and pegging hand in hand. If he is locked for a few days prior to pegging, he is much more prone to arousal and relaxation. It will feel better to him and he is capable of much better verbal and non-verbal communication. I thoroughly enjoy the head space that he is in after a pegging session so I very rarely allow him to orgasm after pegging.

Leave him locked through the entire session so he isn’t reaching for his penis. While locked, he is focusing on the stimulation I am giving him rather than trying to stimulate himself. We’ve not yet experienced the prostate orgasm together but all of the how-to guides recommend staying clear of penile stimulation.

Restraints

Have you tried using handcuffs or any sort of restraints? If you struggle with getting him into a certain head space, try tying his arms to his sides with velcro restraints. Perhaps some pink fuzzy handcuffs beneath him. Taking the dominant role may be more than strapping on a big pickle. It might be fun to try being more assertive and dominant. Give it a try?

Prostate Orgasm

The prostate orgasm is an elusive beast that seems to be possible for some men and impossible for others. There are some tips and tricks to try and give one to your guy. Don’t be discouraged, it will take a level of comfort with you and with pegging and butt play. Some guys will never experience it while others will experience it quickly and with very little practice.

Here is a great description of the prostate orgasm from lockthecock.com:

Prostate Orgasm is a completely different ball game, and it’s not something easily achieved by most men. Sometimes referred to as anal orgasm, a prostate orgasm is the pinnacle of male pleasure.

There are two important things about a prostate orgasm. One, is that it can be a full-body experience that a man cannot achieve through simple penile stimulation. These orgasms can be like waves of pleasure, emanating deep from the core of your body and washing over every extremity.

The second important thing about a prostate orgasm is that you can have one without triggering ejaculation. This is important because of the refractory period. When a man ejaculates his body enters a state of recovery, where he will be unable to have another orgasm for a short period of time. With a prostate orgasm this isn’t the case, so you can cum again and again.

Actually reaching prostate orgasm isn’t an easy process. Many men will need to practice prostate stimulation for months or even years before they can reach it. If this is your goal, you’ll need to be completely calm and comfortable with your own body, and commit to following the feelings and fully losing yourself in the process!

lockthecock.com

Kev isn’t yet capable of hands-free prostate orgasms yet although we’ve certainly tried. Men who are able to locate this fabled pinnacle of male sexual pleasure experience it in one of two ways. The first way is a dry orgasm and the second is a wet orgasm. The only difference between the two is the dry orgasm lacks a full ejaculation.

The wet orgasm does provide sexual relief and a similar refractory period that accompanies a typical orgasm. In most ways, the wet orgasm seems very similar to a normal ejaculatory orgasm although it can feel more intense radiating from inside the body rather than radiating from the penis like a typical orgasm.

A dry orgasm produces no ejaculation although it may be accompanied by some dripping or leaking. The wet orgasm is a full ejaculation. Some men experience both when stimulated in different ways and for some men, only one type is stimulated by the prostate orgasm. The dry orgasm typically amplifies the desire or need to have a wet orgasm shortly thereafter since it does not expel an ejaculation like a typical orgasm does. Another interesting thing about the dry orgasm is the fact that it isn’t accompanied by a refractory period. This means that it is possible for some men to experience multiple orgasms back to back if prostate stimulation continues. The prostate can become ultra-sensitive after the first orgasm occurs so it may be uncomfortable for him to continue.

If your guy hasn’t been able to experience a prostate orgasm, keep trying. The prostate is a walnut sized gland on the front side of the body (toward his penis). With lots of lube, relaxation and directed stimulation of the prostate gland you can hopefully get there.

Don’t Make It Something That It Isn’t

Despite the fact that we all agree pegging doesn’t make a guy gay and doesn’t mean anything about his sexuality. Steer clear of saying anything that would take his mind to that spot. Steer clear of anything that would make his mind go anywhere that doesn’t involve the two of you. For the same reason, don’t discuss cross dressing unless it has been brought up before. Despite what you see in porn, pegging is rarely about homosexuality, cross dressing or femininization.

If you want to do any of the above things or think your guy might be bisexual, this is a bigger conversation which should be discussed outside of the bedroom or at least not in an intimate setting. Pegging should be a wonderful way to escape from the gendered body that society has imposed and give you the opportunity to enjoy the other aspect of sex for what it is. Just sex.

Friends

Is pegging something that can be discussed openly with your friends? If so, bring it up in conversation. This is something that the two of you should discuss first and ensure that you are both on the same page. Normalizing pegging among your friend group will make this practice feel less taboo to both of you. There is nothing to be ashamed of, pegging is gaining cultural acceptance as we gain greater understanding of our bodies and gender roles.

Just for fun

I would like to again recommend Ruby Ryder’s Pegging Paradise website and podcast. I’ve learned a tremendous amount of information about pegging from her podcast and can’t recommend her enough in her stated quest to change the world, one ass at a time.

Did you know that pegging has its own holiday, mark your calendar for October 13th!

Frequency

How frequently should you peg? It really doesn’t matter! Some couples choose pegging as their primary method of lovemaking. Some couples do it a few times a year and still others mix pegging and PIV sex equally. There really isn’t a right answer so pick what is best for you.

Aftercare

Pegging gets me very horny, I think it is the power exchange. After a session, he will either perform oral sex on me until I get off or I will lay beside him and masturbate. Usually the latter since he is normally quite exhausted and submissive after a pegging session (applause please).

If he is locked while he is watching me masturbate, and gets aroused, his cage may become uncomfortable and tight due to his erection. If he complains about being caged, you can suggest that he go to the other room until you are done. This has only happened one time with us and he learned his lesson.

If he isn’t locked, I recommend that you not allow an orgasm. For a male, an orgasm will remove the state of mental submission and close his lines of communication. If you do want to allow an orgasm, give it an hour or two so you can enjoy who he is when he is in this state. He has accepted your dominance and a level of incredible intimacy. This is a time for some wonderfully open conversation with an attentive and genuinely interested man.

Another idea is to get into the habit of having him thank you after your lovemaking together. This will help reinforce the submissive role and help him acknowledge to himself that this is a type of sex that he can admit to enjoying. It wouldn’t hurt to throw in a compliment of your own such as “It was very sexy when you __________”. Together, you can make pegging a wonderful physical extension of your relationship.

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Bluesboy

Wonderful post. Wish she would try it and we could try out the experience..maybe I’ll discuss it again with her

Tmo52nv

Great post! I truly wish that there were more woman who really like pegging there man like you. Talking communications, when I expressed my enjoyment of pegging to my girlfriend, she became cold, like she was disgusted? And she would avoid the topic? That relationship faded out I’m glad to say. But it can be difficult trying to broach the subject with my present girlfriend. I want explore it with her, but don’t want to repeat the same experience?

Fan of pegging

khorina5

Great post! i have little experience, but it profoundly marked me. As a youngster, the first Domina i met had a fem sub pegging me on the first session, and afterwards. It’s crazy, but the connection was SUPER intense, as was the submission. In a twist, my whole image was transformed into that of a slave to the Domina as i paid attention to Her while i was being pegged. i was even super careful/respectful to the fem sub that pegged me. It’s such a very special connection.

subhubphx

Spectacular post Emma. Thank you. I have sent so many of your marvelous collection of words to my Mistress Wife because of the real-life, realistic, non porn-fueled perspective from a modern woman. She loves that and so do I

Vikter

Additional suggestion, once he is comfortable push the head in until he can feel the pressure on his prostate, push past by the length of the head. Take your finger and circle the shaft right where it meets his anus. That is your depth marker, short aggressive strokes almost all the way out and back in to your marker. If he was getting close to orgasm that might be enough to push him over.

Also do not underestimate the importance of orientation, the top of the head should be towards his prostate. Especially important if your dildo has a curve to it.

mrbillsails

Wow! What a great, thorough and extremely informative article.
My wife has pegged me a few times and I loved it. Unfortunately it has not become a regular activity as I had hoped. Perhaps by sharing this article with her it will at least get us started on communicating about it.
Thank you!

Saturnalia

This post resonates with me. Pegging is so very essential in our relationship. We have sex 3 or 4 times per week and the majority of that is pegging. I have endometriosis and vaginal sex can be very painful. We started pegging during an especially painful episode. My sexual confidense came slowly. I was timidly cuddling at first. Slowly I gained more confidense he enjoyed it more. Now I wear my strapon to bed sometimes and cuddle with him while we watch tv in bed just to feel myself as the big spoon presed up against his bum. The biggest thing for me is the technique of sliding it all the way in and all the way out, from this technique he had his first prostate orgasm which was incredible and unexpected for both of us.

Holding his hips tightly and doing from behind is our position for sure. I love the movements of his body that I can feel. Pegging is wonderful. Thank you for posting this.

RandiWithAnI

This is true to me also. The mental aspect for both of us is fucking outstanding.On days where I want to get down and dirty I always text my husband through the day with overtly sexual demands for it.I’m going to fuck you tonight, you’re ass is going to be sore tomorrow. I wonder if you are going to be able to walk after what im going to do to you tonite.

It sounds overly sexual but he responds very well to it. It also sets expectations of what kind of sex we are having so he can prep himself for the fun.