In Hump Day, award-winning psychotherapist and TV host Dr. Jenn Mann answers your sexiest questions — unjudged and unfiltered.

By Dr. Jenn Mann
Updated: Apr 03, 2019 @ 5:04 pm
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DEAR DR. JENN,

A guy I have been dating for a few months wants me to try pegging with him. I have to admit, I didn’t even know what it was when he asked! When he explained it, I was intrigued and also kind of confused. Are we really doing this now? If he wants to be penetrated, does that mean he’s gay? What do I need to know and where do I begin? —Miss Peggy

DEAR PEGGY,

Just so we are all on the same page, it is important to define pegging. Pegging is when a woman, or anyone without a penis, wears a strap-on dildo and penetrates her partner anally. If you are a woman, and your partner is a man, pegging is still heterosexual sex. Experimenting with pegging may be a change in how you both give and receive pleasure, but it won’t change your sexual orientation. So, no, pegging, or anal penetration in general, is not “gay.”

While there are many men who feel like their masculinity would be in jeopardy if they were to allow a woman to give it to them up the butt, plenty of others are all for new ways to get off. In a now-famous interview with Taffy Brodesser-Akner for GQTom Ford actually said that every man should be penetrated at least once in his life in order to better understand the invasive and vulnerable nature of sex for women. And some women who have tried pegging say it helped them better understand how hard men work in bed when they’re doing all that thrusting and maneuvering. And who couldn’t stand for a little more bedroom empathy, right?

But that’s probably not why you’re here. You are probably here because pegging is hot and getting more mainstream. The term was coined by Dan Savage, of the Savage Love Podcast. According to Savage so many people were writing to him about the then-nameless sex act that, in the interest of word space, he needed a one-word one-syllable name for it. In 2001 he challenged readers of his column in The Stranger to come up with a good name. The final chosen name was the verb “peg.”

It was an episode of Broad City over a decade later, when Abbi (Abbi Jacobson) is in bed with her neighbor and erstwhile love interest Jeremy for the first time, and he asks her to peg him, that really brought the concept to the masses. Vulture even declared 2015 “the year of the strap on." And sex toy website Lovehoney reported a 195 percent increase in searches for strap-ons in the year following that episode.

Before you strap one on and go at it, there are some things you need to know.

Pegging Means Power

Pegging plays with power and gender roles. As Savage tells me, it is sexual play in a “deliciously wrong space.” In other words, the taboos that surround the act make for more pleasure, as is often the case with great sex. It is important to be mindful that penetration is vulnerable, especially for a hetero dude who is unfamiliar. The fantasy of what it will be like and the reality of the experience may bring up unexpected feelings of violation, shame or anger. As the partner, it is important to be there for him emotionally afterward. Some men may feel sad and cry or even get angry and aggressive. While you must always put your safety first, be prepared for an emotional reaction to such a vulnerable experience.

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Many women enjoy the power of being the one who is controlling the sex. The power of controlling the pace and the pleasure is seductive. To be on the giving end of the rod is a whole other emotional experience. If you get off from giving a great blow job, pegging may be for you.

What You'll Need

This sex act requires some serious equipment. Making sure you get the right stuff is important in order to have a great first experience. Here is what you absolutely need:

1. A solid strap on harness. All the pegging aficionados I spoke with say this is where you want to put your money. Quality is important and most recommend a two strap harness. After all, nobody wants a floppy dildo. Other options are a corset type, or an underwear harness, which is cuter but gets floppy with bigger toys.

2. Dildos. Don’t let your eyes be bigger than your boyfriend’s ass. It is best to start smaller than you would like and then move up. You only have one shot at his first time and you want it to be a positive experience. Many strap-on dildos come in kits, even ones designed for beginners with smaller dildos. Make sure you choose soft silicone with a wide flared base.

3. O rings. You will want a set of O rings in different sizes that can accommodate for different size toys. Like a cock ring, this can give the recipient a little extra sensation.

4. Lube. Lubrication is of the utmost importance since the butt is not self-lubricating. Sliquid Silk Lube, which is a hybrid silicone and water based lubricant, is particularly good for pegging or any other toy play.

If you want to get fancy, there are additional accoutrements you can try. Keep in mind, these are advanced moves. You can add a bullet vibe for your own pleasure. There are even strap-ons that have a special pocket for your bullet. For a beginner, the distraction of the vibrator can be like rubbing your tummy and patting your head at the same time. You may want to get your moves down first. Double-ended dildos are popular with the experienced crowd. They require enormous skill but double the pleasure. 

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Getting Started

Even just having a conversation about pegging shows that your boyfriend trusts you and feels comfortable. Whether you actually end up trying it or not, this should open up other conversations about what you want in bed, which is great. Open communication is the key to a great sex life. You may even want to visit the sex store together as some pre-foreplay.

Before you jump into that ass, I recommend starting with some gentle exploration. Using lube, you will want to explore the area with your finger or fingers before inserting objects. To go straight into pegging with a newbie is the equivalent to expecting a couch potato to run a marathon his first time exercising. Even if, by some stretch of the imagination (or anus) he is able to do it, he is going to be hurting too much to enjoy it. Before you begin, you should also get a little ass 101 by checking out my column on anal stimulation. This will help you know how to prep him, find his prostate and give maximum pleasure while minimizing pain. Keep in mind, studies show that men have orgasms that are 33 percent more intense when their prostate is stimulated. While not all men orgasm from pegging, the ones who do tend to blow hard.

Getting Over the Awkwardness

Your first time pegging may be awkward. Even just putting on the equipment can be complicated. You may want to give it a dry run on your own, so you’re not trying to figure out how to put on your harness and what to do with an o ring right in the heat of the moment. It can take some trial-and-error. Keep in mind that the strap-on should feel like an extension of your body so you can control it better. You want to think of the dildo as an appendage. Make sure that when you feel resistance, you stop so that you don’t hurt your partner. Continually check in with them and ask how things feel. Good communication is the key to good pegging, or any sexual activity.

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As with any form of anal play, people worry about the mess factor when it comes to pegging. There are things you can do to lighten the load, so to speak. Some people are happy to soap up in the shower before while others go all out with an enema to clean themselves out. If you go the enema route, make sure you do it a few hours beforehand so you do not have a water leakage situation. Another easy way to avoid messes is to get a Liberator blanket which can handle all kinds of liquids while keeping your bed (or floor... or dining room table) clean.

Pick Your Position

While television portrayals of pegging seem to be heavy on doggie style, there are many different ways to peg. Some popular positions are: missionary, on your sides, cowboy, reverse cowboy, and a semi-missionary where the receiver is on their back with their knees up. Finding the right position is a combination of anatomy, comfort, and how much intimacy or eye contact you are both comfortable with during the act.

Now, you’re fully prepped for a fun first pegging experience. All that's left to do is strap one on.

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