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“If there is one thing I hate, as a man, it is experiencing new sexual pleasure and being brought to new orgasmic heights.”
-Completely Made Up
So, there’s a reason I had to make up that quote: it has literally never been said, even by accident. I know I’ve never heard a man say that, and none of my lady friends have, either. I’m guessing none of the men reading this have ever said that.
And yet, I’ve had a variant on this conversation several times.
Pegging, as we discussed in our Ladies’ Guide to Pegging, is where a woman using a strap-on dildo anally penetrates her man. This can also be done with a handheld dildo, but true pegging involves the woman essentially imitating the traditional male sex moves. She gives; he receives.
But for a huge number of you fellows, even ones who are sexually adventurous, pegging seems beyond the pale. It is taboo, and there are a lot of objections to it. Some are rooted in traditional notions of masculinity; others are in physical squickiness, though really, the two are largely related.
When that is overcome, though, more and more men discover they love being pegged. Doing so stimulates their prostate, which contains millions of nerve endings, and is known as the “g-spot for men.” To make a long story short, it results in an amazing ejaculation.
So why is it people object to pegging? Why is it that men who try it find pegging to be amazing, an incredible part of a mutually-respectful relationship? And if you are curious about it, how do you get from instinctive objections to, well, being pegged?
Like everything else, it starts with communication. There is an enormous need for communication in all sexual relationships, especially if you are trying something new. But when it comes to pegging, the first conversation may need to be with yourself.
Understanding and Overcoming a Guy’s Objections to Pegging
Before I get into this section, I should make a couple things clear. If you simply are not into pegging at all, and not curious, there is nothing wrong with you. Not every sex act is for everyone. Some guys grow faint when they hear about a toy called a “ball stretcher” and some, well, just grow.
But if you are curious about it, are interested in trying it, but are letting these common objections hold you back? Well, let’s talk about it. Some (maybe most) of you reading this won’t have these objections, or will have already talked about them, but I think it is good to go over them.
Does liking anal pleasure, especially when there is a penis-like object thrusting into me, mean I’m gay?
Okay, this is a simple one: no. It just means you like having a sexually pleasing sensation. Which… you do. For obvious reasons of anatomy, anal sex is associated almost entirely with homosexual men, and because of that, and because of pernicious homophobia, the enjoyment of it is seen as “unmanly.”
Well, there are two obvious objections to that. One is that there is nothing “unmanly” about being gay, and obviously absolutely nothing at all wrong with it. And two, I think enjoying a great ejaculation is pretty darn manly indeed.
Will it hurt?
Then there is the physical objection. Many men think that they will just be in massive discomfort from anal sex, partly based on dumb cultural stereotypes.
Now, the first time is always interesting, to be sure. It’s the same for a woman’s first (and many women enjoy anal sex, so they have managed to overcome this objection). But there are ways to mitigate that.
- Start with toys. You don’t have to go from Zero to Jackhammer Sex. Start with anal beads or butt plugs.
- Use smaller dildos. No matter how open-minded, a lot of men will blanch when they see a giant dildo coming at them. Until you are used to it, start with a smaller dildo. Get comfortable. Don’t go bigger than you want.
- LUBE. Yup, we capitalized that, and for a good reason, too. You’ll be using lots of lube: on your cheeks, on and around the hole, and on the dildo. Lube is your friend.
Does it mean I’m not in charge?
Well, to an extent… yes. But guess what? Sometimes that is great! The man doesn’t always have to be “in charge.” In a loving and mutually-satisfying, respectful relationship, both sides can take turns being dominant or submissive, and both partners can please the other, or control them, or both.
(Obviously, some BDSM relationships are, by choice, one-sided, but that is the point: by choice.)
Giving up control sometimes is part of a healthy relationship, and that is one of the joys of pegging. Let’s look at some more.
Quick Aside for a Pegging How-To:
We’re a little brief here on how pegging actually works and what you need to do to be successful, but that was all covered in our “Woman’s Guide To Pegging.” Be sure that at least one of you reads it.
Why Pegging Is Amazing for Men
We’ve touched on it, but here are three reasons why pegging is amazing for men and great for relationships.
You’re More In Tune With Your Partner
The second time my husband and I tried pegging, he said something really interesting (the first time he wasn’t much for talking). He said he understood what it meant to be penetrated, both emotionally and physically. He understood what it meant to let yourself go and open your body. He said that although there were so many cultural and physical differences, and it wasn’t the same, he understood a little more what it was like to be a woman.
That was cool, and I think you’ll have a similar reaction. Men and women have different experiences with sex, and experiencing it partially from a new perspective is always a good thing. It might make traditional sex better as well. And bonus: she’ll understand it better, too. I now have first-hand knowledge that it isn’t always easy to keep thrusting—and I didn’t even have to worry about holding back my orgasm.
Role Reversal Is Hot
One thing we really like to talk about here is the power of role-playing. You can sort of shed your skin and don a different mask (sometimes a literal mask), and that lets you be freer. Role reversal is like role-playing, only you also get to be yourself, with your partner.
And as weird as this sounds, I know that I love sometimes the thrill of strapping on a fake penis and being on top. And my husband loves being on bottom. It feels slightly transgressive, with all the naughty thrills. It’s like we’re not just doing a masquerade, but a full biological costume party.
But let me say it again: pegging isn’t anti-biology; if it were, it wouldn’t feel so damn good. But given cultural weight, it can feel rebellious, and that is super hot.
Did I Mention the Orgasm?
Throw off the cultural weight! Reverse expectations! Be more in touch with your partner. Be more in touch with yourself.
But at the end of the day? What you’ll really be thinking about is the shudderingly intense orgasm you’re having.
Whether your partner is reaching around and stroking you, or you are going to town on yourself while she thrusts into you, or whether the novelty and intensity of your prostate being played with is enough on its own, you’re going to have a good time.
It’s all about feeling comfortable. Comfortable with yourself, comfortable with your partner, and physically comfortable. So talk about it. Use the right toys. Work your way up to it. Explore and converse. Have fun.
When you are comfortable, you are ready for her to be inside you. When you’re comfortable, you’re ready to experience things you’ve never felt. When you allow yourself to be comfortable, and to fully explore the world of pegging, you’ll feel those old objections and outdated ideas spurt away, drowned out by your moans of pleasure, and the shared sweat of lovers.