The following is a piece from one of Volonté’s male contributors who wished to have it published anonymously.
It was her idea, and the confidence with which she told me she wanted to do it to me put me at ease. “Yeah. Sure. Why not?” I replied, when she showed me the picture of a strap-on dildo that she already owned.
I found it quite sexy that: 1) she already owned strap-on sex toys and therefore probably had a lot of trustworthy experience, 2) she had a photos of them on her phone, just in case it came up naturally in conversation, and 3) it actually HAD come up naturally in conversation, on what was probably only our third or fourth date.
To be honest, I’m probably more open to the idea of pegging than most guys. I’m aware I had a bit of a headstart, and had already owned and used anal sex toys in the past. But still, pegging was virgin territory for me, and I knew I wouldn’t know what to feel about it until I was doing it.
And already, this exposes a number of hypocrisies and contradictions in a lot of people’s attitudes to pegging. I was excited to be asked if I wanted to try it, which is great, but also disappointing, because I’d been sexually active for well over a decade when this happened, and no one had ever asked me about it before. I suspect a lot of women would be excited to try it, and men too, but there is undeniably a nervousness or self-consciousness about raising it.
Why is this the case? Well, this is where we get into choppy water. Pegging, between straight couples, inverts the traditional framework of gender and sexual roles. For some, that’s exactly the point, and that subversion of stereotypes alone is enough for both partners to derive pleasure. For other couples, the interesting psychology of it doesn’t matter: the physical sensations are what matter, and the sex act itself is stripped of any politics.
All this complexity, wrapped up in existing taboos surrounding male anal pleasure, and you can start to understand why pegging is a difficult topic to approach early in a relationship.
How to Ask Someone if They Want to Try Pegging
So how DO you talk about pegging? This is simultaneously a thousand times easier than it sounds and a thousand times harder. The hard part is raising it as a desire – a major obstacle for most people. But, as obstacles go, it’s still easier than, say, teaching yourself to fly a crop-duster and asking ‘CAN WE TRY PEGGING?’ in 500ft letters in the sky. It’s just talk, and that’s really easy.
The trick is to ask with confidence, and be excited about it – or at least, hide your nervousness about it. Regardless of your role in the pegging itself, you’re far more likely to get a positive response if you ask in a positive way.
Pick your moment though. If you want to try being pegged, don’t just blurt it out while you’re having an argument with your partner about grocery shopping. “You forgot the milk again, didn’t you?” “PEG ME!”
PROTIP: ask while you’re having sex. Sow the pegging seed in a sexual context. Actually, that applies to just about everything. You’re welcome.
What Does Pegging Feel Like?
Ok, on to the fun stuff. What is pegging really like?
This all depends on the way you’re doing it, and I’m tempted to simply answer ‘it’s like any kind of sex: when it’s good, it’s great.’ But I think you probably want more than that.
Let’s assume for a moment that it’s the inversion of those oldy-worldy relationship dynamics that you want to explore. For that, there’s nothing I can think of that that’s more satisfying. You get to set the tone of it with your partner: if you want to be humiliated, if you want to feel emasculated, pegging can satisfy that desire entirely.
But, that makes pegging seem like it’s a lot kinkier than it really is. And that’s where we encounter one of the many double standards involved in the relationship between male and female sexual pleasure: that because, in this particular dynamic, pegging empowers the woman, it’s automatically “non-conventional” (to use the language of British obscenity laws).
But that’s not always the case, nor is it an issue when it is the case.
Now, let’s assume it’s the sensations you’re interested. Pegging allows for some real, tangible intimacy, especially if it’s done in a face to face sex position. The physical sensations, assuming you’re using something of relative size to BILLY (which, at around 4 inches insertable length and 1 inch diameter, most users would describe as ‘small-to-medium’), are incredibly pleasurable.
Somehow, allowing somebody else to be in complete control of your sensations adds a new dimension of physicality to anal pleasure. Technically everything is the same as if you were performing the same actions solo, but with a partner, everything becomes more… substantial. That’s just the nature of sex, I guess.
Square Pegs, Round Holes
Now, I’m very aware of the ground I’ve failed to cover above. I haven’t talked in any detail about my partner’s experience. Nor have I even touched on less traditional relationship dynamics, or non-linear, non-binary gender and sexual dynamics. Another time, perhaps. This time, I just wanted to try to explain to someone who might be close to trying it what they can expect:
Pegging is as kinky as you want it to be. If you’ve tried it, you probably love it. If you haven’t, you probably will.
Still Curious? You can read more expert articles about anal sex or go back to our Ultimate guide to everything about anal: