A hole new world: An absolute beginner's guide to pegging

Pegging is trending once again. While heterosexual men have been taking it in the butt for hundreds of years, in 2020, we saw a new uptick in the Bend Over, Boyfriend phenomenon. It’s not clear why this actually not new practice is hot right now, but before you say, “Sounds gay, I’m in,” and start pegging away, there are a few things you should know. I talked to some anal experts about what beginners need to know about pegging.

First of all, pegging as we know it is not actually gay. But it does have kind of gay roots. The term was suggested by a reader of Dan Savage’s Savage Love column in 2001 as a way to describe heterosexual women fucking heterosexual men in the ass. “Boy prostitutes were sometimes called peg boys because they would sit on pegs to keep their assholes open between clients, so I suggest the word ‘peg,’” wrote contributor Paris P.

Savage initially brushed off the term, but it stuck around in the Savage Love community and eventually made its way into mainstream usage. Now it’s used to describe basically any instance of someone of any gender penetrating someone else in the ass with a dildo. Regardless of who’s fucking whom, here’s what you need before you start experimenting.

Have a conversation beforehand

“It's ideal to have a partner in mind who wants to explore pegging too — as with any kind of anal play in partners of any gender combinations, anal isn't for everyone and that's okay.” says Carol Queen, Carol Queen, co-founder of the Center for Sex & Culture in San Francisco and co-creator of the anal instructional series Bend Over Boyfriend.

“Being penetrated might be — or evoke — a form of gender play. It doesn't do that for everyone, but it definitely does for some,” Queen explains. This can be true for both the person penetrating, and the one being penetrated.” Because these acts have gender coding in our culture, they may affect our sense of identity as much as our bodies and that needs to be thought of and discussed in advance.

Yes, agrees Taylor Sparks, a sex educator in Hollywood and Founder of Organic Loven, one of the largest BIPOC-owned online intimacy shops. “This is one of those times that you really do have to use your words.” Because you may have had the initial, “Wanna try this?” conversation hours, days, or weeks in advance of the act, you need to make sure that your partner is still excited to try it, Sparks says. And, Sparks emphasizes, the pegger and the peggee need to participate equally in the conversation and proclaim their enthusiastic consent before anyone gets out the lube.

Get yourself a dildo (and a harness)

It’s probably obvious, but you’re going to need a dildo. What’s not obvious is which dildo. That’s because this is largely a very personal choice. “It's especially good to choose your dildo in consultation with said partner, since people will have very different size preferences depending on their experience and comfort level,” says Queen. She recommends using a dildo made of a flexible material — like silicone, starting small, and working your way up to larger sizes if it and when it feels good.

People ask me all the time for dildo and strap-on harness recommendations, and while I do think that these are entirely personal choices, I also have some #protips. People with vaginas, for example, may get some extra pleasure from using a strapless strap-on — a dildo that is held in the vagina with what is essentially another dildo attached.

If you want to be penetrated while you are pegging, strapless dildos are a great option, but I don’t recommend using a strapless dildo without a harness. You can, but it can be a little distracting to try to hold it steady in place while you’re thrusting. I like to use a strapless dildo in conjunction with a harness — the strap in “strap-on.”

When it comes to harnesses, I think you really get what you pay for. If you’re just experimenting, you may not want to spend a lot of money, but personally I think making that investment up front — ha — pays off in terms of both leisure and longevity. I’ve had the same harness — the Spareparts Joque ($125) — for actual decades. It has a lot of adjustment options and no metal parts, so you get all the control you need without worrying about it rusting when you wash it — which you should definitely do.

Get good lube

I don’t know who still needs to hear this, but you need to be using lube, especially when it comes to anal. Make sure you use a lube that works with the toy you’ve chosen — don’t use a silicone-based lube with silicone dildos — and use a lot of it! Despite rumors in the culture mill, the anus is not self-lubricating, full stop. Lube can make the difference between a pegging experience that gets you off and pegging that makes you tell someone to get lost.

It may be tempting for newbies to use a numbing cream, but please resist the urge. “The one place you want to feel pain is during anal sex so you know when to stop. The anus is very susceptible to microtears. You don’t want to discover that you/they have been hurt after the numbing cream wears off,” says Sparks. “If you are feeling pain, that is a sign to stop.” This is another opportunity for good communication. Make sure you are talking to your pegging partner and asking them if they need more lube. Personally, I find experimenting with lube to be part of the fun, and buying lubes that are organic from BIPOC-owned companies is a good way to make your politics personal. Like really really personal.

Experiment with positions

As with every other sex act, there is no one best position for pegging. Two really good positions are a lifted missionary or doggy style, says Sparks. You can get just the right lift by using sex pillows that are firm, will hold the person's weight and give good height, angle and depth — Sparks’ recommends a pillow called Liberator ($70). If you need positional inspo, Queen’s Bend Over Boyfriend is a series of instructional videos that is both informative and hot af.

Both Sparks and Queen recommend getting a little anal education before you experiment with pegging. That means knowing a little something about anal play and a lot about your body. Having some backend knowledge — yes, I said that — will maximize pleasure and minimize risk.