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.
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.
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. …
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.
Does she allow you orgasms when you peg? How do orgasms play into your tender or aggressive play sessions?
Don’t you feel emotional and vulnerable during normal sex?
That may also be tender or aggresive.
Pegging is just the same as normal sex, its an act between 2 people that opens you up to the pleasure of emotion and closeness.
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.
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.
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.
The 10 second countdown is great. I can only imagine the pressure that he puts on himself to cum.
Oh, don’t think that the count down means I can cum. It just means I have to get to the absolute edge by the time My Love gets to 1 and then immediately STOP!
Delicious torment ;).
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? 🙂
This article was half helpful.
Couple of mistakes, after pegging men won’t or are unlikely to feel anymore emotional or vulnerable than after normal sex. This is just something women think. Its not true.
On the topic of cumming, YES he should cum. Be prepared for more than normal, if the position you choose is him on top facing you, you might want to cover your face, its more explosive than normal too. Cumming does not end post-peg cuddles. That’s a sexist view of men put about by women who have little real experience of men. Its quite likely teens will feel less cuddly after any type of sex.
Pegging sex is much the same aa normal sex except the woman does the penetrating, would you have sex and not want to cum for a day or 2? Just an odd, inexperienced thing to think.
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