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. 

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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:

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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

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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!

Pegging Couple

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.

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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.

Don’t forget to make pegging fun, you can find some incredibly sexy harnesses and some fun and kinky dildos to make life exciting. Snake dildo anyone? Listen to each other, understand what makes him tick and what sends him over the edge and you won’t regret pegging your fella.

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.

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