About Him · Pegging

Pegging Positions

If you’ve spent any time reading my blog, you’ve undoubtedly seen that Kevin and I truly enjoy pegging. If you haven’t tried pegging, swing over to the pegging for beginners blog that I wrote earlier this year.

Over the last two years, this form of sex has become as frequent as “old school” piv sex in our bedroom. We both love the closeness and connection that pegging allows us to share together. The intimacy and vulnerability that I can see in his eyes are so very sexy. Here is a quick list of ways that we love to peg! I also threw some videos in because I never do videos and they are great for demonstrating positions.

Pre-Pegging Cuddling

After pegging, guys seem to love cuddling and physically reconnecting but we will get to that later. I am talking about cuddling in bed together, with your strap-on. When we first begun pegging, I would strap up, do the deed clean up and enjoy some post-pegging cuddles with my big guy. As we’ve made pegging a bigger part of our relationship, I like to ask him to fetch my harness while I select a toy. Then we may lie in bed and watch TV or just cuddle and talk. While he knows the direction that the evening will be going, it helps him relax and not get so anxious.

I do like to ask lots of directed questions since he is still reluctant to tell me that he wants it. Kevin rarely asks for pegging even though I know that he enjoys it. I will cuddle with him and ask him if he wants to feel me inside of him. The pause before he admits it to me and presumably himself is palpable. “Yes” he whimpers.

We both enjoy pegging but society has made butt play something shameful for guys. My questions are intended to normalize this act within our relationship. We are both consenting adults and pegging is here to stay so he might as well admit that he actually enjoys it.

Spooning

The cuddling most frequently progresses into some dry thrusting and rubbing before we get down to business. We oftentimes straddle the line between spooning and cuddling as we slow and enjoy each other’s touch. We both lie on our sides and I of course get to be the big spoon in this position. This position is very intimate and passionate and you are close enough to hear his moans and feel his breathing. This position is very easy and can be done with any size toy. I tend to prefer a shorter, thicker toy since the larger girth makes for more man-noises and breathing which I so enjoy.

Standing

In contrast to spooning, he standing position feels much more aggressive. The standing position is best done with a longer, thinner toy. Your fella should stand up against a wall, pushing his bottom out toward you with a slightly arched back. Grasp his body with both, slowly insert the tip of your toy and progressively thrust your hips upwards into him. His reactions are priceless, a very lustful position.

If you are shorter, you may want to wear some shoes although I wouldn’t recommend anything with heels since balance is a thing. The longer toy means that a longer thrust is possible so you can get quite the workout. This one is a great way to start and move to another position such as sitting.

Sitting

With the sitting position, you sit on a chair or the corner of the bed and he sits on you. We typically start with him facing away since it tends to be easier to get started that way. Once he is warmed up, I will tell him to turn around and face me. This position is very easy and he does nearly all of the work. Any shape or size toy is ok since he is doing the majority of the work. Remember to find a vibrating toy for yourself, it feels quite good since he is up close and personal.

Missionary

Missionary involves the man laying on his back, with the woman behind him. He will usually lay on his back with his butt on the edge of the bed. I lean forward, into him. We both have access to his penis. I see his facial expressions as I enter him. I like doing this slowly and reminding him to breathe deeply and relax. This one is also quite easy but it can be tiring on the hamstrings and thighs. We use either a larger girth or a ribbed toy that stimulates his prostate. Longer toys can be uncomfortable to him in this position.

Doggy Style

Doggy style is great although it tends to make him the most anxious at first since I am behind him and he has the least control of any of these positions. He is sitting, waiting, accepting me. A level of trust is required and once you feel him finally relax his body, this can be one of the most intimate of pegging positions. Doggy style is probably the easiest of the pegging positions and can work with any size dildo. We typically go with a larger girth toy. Like missionary, this position allows the toy to go very deep and can be uncomfortable to him.

The Post Peg Cuddles

This is one of my favorite parts! After pegging, he very clearly feels vulnerable, emotionally drained, unsure of himself. Seeing him get sweet and needy and slutty. The feelings go right to my crotch and my heart. Watching him gasp for breath as you enter him and feel so full is like nothing else. You will find him naturally wanting to touch your body and cuddle with you. Prepare for the fact that he will be more verbal about his feelings since pegging is such an emotionally overwhelming experience. Guys aren’t used to being dominated and he will be expressive about his feelings and emotions that range from shame to excitement. Comfort him and enjoy watching him ride his rollercoaster of emotions. The dopey expression of tender submission on his face will say it all.

This is the best time to get him to talk about what he liked and what he didn’t like about the experience. Ask him directed questions about his favorite and least favorite parts. Ask him how it made him feel to allow you inside of him. Use your words to remind him that you did in fact dominate him sexually but allow him to appreciate and accept that reality together, with you.

Snuggle with him and indulge his feelings. Give him compliments and tell him that he did a good job. Give him some specifics that you particularly enjoyed. You will see a very clear reaction to your reassurance, it is almost cute. The more that you give in to this side of his vulnerability, the more intimate your pegging sessions can become. Let him know how much you enjoy these sessions since it can seem one-sided from the male perspective. We enjoy it for much of the same reasons that he does, it is an intensely emotional experience to take him in this way. He will be physically and emotionally exhausted to the point that he can barely move his legs and is just drained from all of the excitement.

It’s also a perfect bonding opportunity, because he has to open himself up and allow himself to become vulnerable just as I have to. It gives him a better understanding of sex, and we really bond over the shared experience of vulnerability and newness.

You’ve made a huge step by trying pegging together and he has too by allowing himself to be vulnerable for you! In our culture, guys are taught that vulnerability makes them weak but the feelings that you share together will give you a strength like no other. We’ve come to accept penetration and dominance as part of sex but for men, it can be quite a mind blowing experience.

Should He Cum?

If you let him cum, be prepared to put an immediate end to your cuddles. If you forbid an orgasm for a day or two, you will get a more emotional and nurturing man. Separating pegging from orgasm helps him enjoy the act of pegging rather than focusing on the expected release after your session.

If you let him cum, he will be back to his normal self nearly immediately. Give it a try both ways and see what works for your relationship. The orgasm should always be his reward, never a guarantee so I would recommend that you treat it like dessert. You don’t have dessert after every meal but that doesn’t mean that each meal wasn’t good. Denying the orgasm helps give him a greater enjoyment for everything else.

If he hasn’t experienced an orgasm in some time, his prostate is much more swollen and sensitive. After a session or two where he wasn’t permitted a release, his moans are noticeably different and he moves more. Slutty is the best word to describe it, grinding himself on me and doing more of the work. Not just

How Frequently Do You Peg?

I get this question quite a bit. For the last year, pegging has also been on the uptick for us. If I was to look at the last couple months, we peg twice as often as we have PIV sex. This has increased and decreased over time but we really enjoy it. The feelings of closeness that it allows us to experience together are unlike anything that we can get from PIV sex. If we are being real, the truth is that I desire it more so we do it more.

Other Comments

Remember if you have him suck on the toy that it should be cleaned thoroughly with antibacterial soap prior to it being in his mouth. It is an intensely pleasurable experience to look down at him and see your toy in his mouth. Just take the right precautions to ensure that nobody gets sick.

Never use the same toy for vaginal play. Keep the brown toys and the pink toys separate. The vagina is very sensitive to infection so we have two separate toy boxes just to prevent any possible confusion.

An light anal cleaning is recommended to ensure that you don’t have any surprises during your play. Remember that he is only cleaning the last little bit of his bum and not his whole intestinal tract so this isn’t some crazy ordeal. Just a quick cleaning in the shower. This is optional if he feels clean or if you are ok with a possible slight mess.

Come on ladies, it is 2019!
Let’s start PEGGING!

Do you have other suggestions or positions that you enjoy? Leave your feedback in the comments below and I’ll either update this blog or create a follow-up. Thanks for reading!

8 thoughts on “Pegging Positions

  1. Thank you Emma, your experiences are similar to ours.

    For us pegging is a natural part of our relationship. And while general society sees it as ‘taboo’, in our relationship I am as comfortable asking My Love to fuck me as she is telling me to lick her (yes, I have to ask and she gets to tell).

    We have talked about how we feel in both situations, and while the physical sensations are different (obviously her cock isn’t real :)), the emotional ones are very similar for us – that is to say, we both feel vulnerable and open while being penetrated and powerful and giving when doing the penetrating. The act may be tender or aggressive, but always intimate.

  2. Hello Emma, first allow me to thank you for a wonderful site! Although my wife and I have been in the chastity lifestyle many years (I gave her control of my orgasms 8 years ago), I just came across this site and your approach to chastity fits beautifully with ours. We aren’t into humiliation or strict submission (not that there is anything wrong with those if that is what others are into), but rather the control of the intimacy energy between us which depletes when I cum. It is our version of Karezza. My orgasms are at the whim of my wife depending on her need to see or feel me cum. This is because, while I like the feeling of being horny and what is does for our relationship, in the moment I don’t always have the will power to stop from going over the edge.

    The longest I have gone without some sort of release (ooze or ruined) is a month. Three months is the longest I have gone between full orgasms. Typically though, her need for me to cum is 3-4 times a month.

    Back to your questions. Sometimes she lets me cum during pegging and sometimes not. Sometimes it is just a little ooze or a ruined orgasm, occasionally a full orgasm, but quite often it is nothing at all. Sometimes I am in a cage and others not. Sometimes my cock is ignored completely and sometimes it is teased mercilessly. The tenderness or aggressiveness of the pegging does not correlate with her need to have me cum.

    What has been a surprise to us is that even if I am not allowed to cum, I feel satisfied at the end of a session and not as horny as at the start.

    1. Thanks and welcome! It is interesting how quickly you are able to separate orgasm from sex. It only took a few weeks before orgasm and sex are two very separate things. For the first couple months, there is a bit of resentment and he would bother me for an orgasm. I had to learn to be more stern before he would get the point. Giving him warnings was not doing him a favor. He would try and “top from the bottom” and determine how many warnings he could get before I would threaten him with an extended lockup. Now he rarely receives a warning, I go straight to an extended lockup by holding up one or two fingers (indicating days).

      Welcome to the site, come visit us in the forum. We have quite a few interesting side-conversations happening in there.

      1. Hi Emma,
        Early in this journey it actually took awhile for me to separate orgasm from sex. But once I was able to, it opened up so many new options for pleasure. MyPlaything has done some “topping from the bottom”, particularly early on when I wasn’t feeling fully empowered and he was trying to get what he wanted/needed. What I know now is that without him doing this, we wouldn’t have learned so much, had such honest conversations and gotten to the great place we’re in today. It rarely happens now as I feel fully in control.

        One example of this control is him asking to masturbate. In the past he would beg, plead, pressure, or sometimes just do it without asking and then tell me later. Some of this was him trying to get my attention as early on I often approached this a role play vs an integral part of our relationship.
        But now that I feel fully empowered and engaged, he always asks and this has become a sort of “reward” for him. I allow him to play with himself but he is not allowed to cum. I’ll vary the time, sometimes 5 min., sometimes 30, and he never knows when I’ll start the 10 second countdown to when he must stop, which he always does – now. He knows from experience that if he doesn’t stop, the next time he asks it will be denied.
        The shift has taken time, and lots of conversations and experimentation to understand both our needs.

  3. Really nice article. Thanks, Emma.

    My keyholder and I don’t get to see each other many times during the month. We do a variety of things, both traditional and non-traditional, for the times we have together. But I have (we’ve?) definitely become a fan of different ways of pegging. Sometimes it works great, other times not so much. So funny (frustrating?) how things like that work.

    Interestingly, I have a much better understanding of how my lover might enjoy something one time but not the next. Angle of entry, stress, mood… Ooooooh! Got it. Tongue, my sweet? 🙂

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