Why All Men Should Try Pegging

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In a recent interview, Tom Ford argued that every guy should get penetrated at least once in his life. According to Ford, getting penetrated allows you to empathize with women, and understand how vulnerable they are during sex. While I have to disagree on the latter point (more on why later), even if you never try, it I do agree you should at least understand the possibilities: Your prostate can give you a kind of pleasure that your penis never could.

Why All Men Should Try PeggingTom isn’t alone. More and more men are waking up to the joys of being penetrated. The film Deadpool and more recently Broad City (pictured above) both had scenes in which women shagged men with strap-ons–known colloquially as “pegging.” Perhaps in part thanks to this representation, sex toy website Lovehoney says strap-on searches have increased by 195 percent year on year, with November 2016 being their most popular month for strap-on sales. So if you want to try pegging, know that you’re definitely not alone.

But although it’s tempting to plough straight in (pun very much intended), pegging isn’t quite as easy as they make it look on TV. You only get one shot at your first time, so here are a few tips to make sure it goes smoothly.

The first time I ever pegged someone we made all the classic mistakes: We bought the cheapest strap-on we could find, rushed in too eagerly, and didn’t have a clue which position would be best. But despite that it was a roaring success, as measured by the fact that it made him come so powerfully I had to wipe the wall down afterwards. If you’re intrigued by penetration, the obvious first place to start is with gentle anal exploration–a finger or two, with a lot of lube. You’re hunting for a spot a couple of inches inside you, just behind the base of your penis, and it should feel good when you press it gently.

I’ve had some guys who find anal penetration uncomfortable, but they enjoy the psychological aspect. Others like the sensation of feeling “stretched,” and some just want a short burst of pinpoint prostate stimulation to push them over the edge at the end of a blow job. Our bodies all respond differently to stimulation, so it might be that you try this and discover it’s not for you, but if a finger or two does the trick, then full-on pegging might be next on your bucket list.

The first thing you’ll need is pegging equipment: a solid strap-on harness and a decent dildo. Lovehoney’s most popular item is their unisex strap-on kit, which comes with a slim 7 inch dildo. The golden rule with dildos is to always go for something slightly smaller than you think you’d like. Picking too big a dildo for your first time is like trying to run a marathon before you’ve finished your couch-to-5K, and a bad experience could put you off for life. Some guys aren’t keen on dildos that are too “lifelike,” so dildos are available in a variety of different colors, textures, and patterns. You can even use silicone moulding kits to clone your own penis, creating a fun Inception-style shag. That’s probably an advanced move, though, so I’d recommend a soft silicone dildo for your first time, with a wide flared base. That way it’ll sit snugly in the strap-on harness and you won’t risk it falling out and flopping onto the bed at a crucial moment.

When you get going, use plenty of lube and go slowly. Pegging has one crucial disadvantage over standard anal sex: The person wearing the strap-on has no sensation to guide them. Consider how hard penetration is sometimes for you, then multiply that by a thousand, because your partner can’t feel the end of a dick that’s made of silicone.

When you’re in and ready to go, experiment with a few different positions. Doggy always seems to be the default on TV and in porn, but it’s not the one I’d prefer. From a selfish perspective I want to see my partner’s face at the peak of his orgasmic bliss, and from a practical perspective the angle of entry can be much easier with you lying on your back, knees pulled up to your chest. Even hotter—and easier for a first-time—is to get your strap-on wearing partner to lie on their back, so you can ride them cowboy-style. It puts you firmly in control of both the angle and speed of entry.

The cowboy position, in my opinion, also puts paid to Tom Ford’s theory that being penetrated makes someone “vulnerable.” Perhaps the most common question from straight guys about anal penetration is what enjoyment of it means for their masculinity. They often see penetration as something passive or feminine, because depictions of sex often put the penetrator in the dominant role. As someone who’s been on both the giving and receiving ends, I can tell you that this is nonsense. Power play during sex is all about the atmosphere you create—you can be vulnerable one minute and powerful the next, regardless of who’s inside whom. And personally, I think there are few things more powerful and hot-looking than a guy riding a silicone penis that I’ve chosen, lubed-up, and strapped on myself.

And perhaps that’s why pegging is growing so rapidly in popularity. More people want to experience different kinds of sex than the ones they were taught about in sex ed. Guys are increasingly recognizing that being penetrated doesn’t make you “vulnerable,” it’s just another sex trick to add to your repertoire.

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