Pegging: Strap-on anal sex for beginners

So, you’ve heard about “pegging” and want to try it for yourself. Pegging is usually referred to a cis woman penetrating a cis man with a strap-on dildo. You’ve come to the right place; here’s how to have strap-on sex as a straight couple.

A note on the term ‘pegging’

Some people may find the term “pegging” offensive. It was coined back in 2001 by sex educator Dan Savage. He asked readers to vote on what term should describe the act; other choices were “bobbing” and “punting.”

As Quinn Rhodes wrote for Refinery29, calling it “pegging” instead of what it is — anal sex with a strap-on — may reinforce the idea that it’s taboo or somehow “wrong.” It could be used by cishet men trying to distance themselves from sex queer people have because of their fear of being perceived as queer or emasculine. In our society, we’re taught that sex is a man penetrating a woman, and that he has more power/control. The penetrated partner, then, is deemed as weak or submissive. 

Sex is much more than P-in-V, and doesn’t have to adhere to these stereotypical power dynamics. Sex and desires also don’t determine one’s sexual orientation.

Pegging “doesn’t magically change your sexuality,” said nightlife entrepreneur and former professional dominatrix Venus Cuffs. “The goal is to have fun with each other and safety, preparation, and communication allow you to focus on pleasure and enjoying yourselves together.”

Of course, there’s nothing wrong with being queer or submissive, but these ingrained beliefs can take time to unlearn. Before having strap-on anal sex, reflect on and explore your relationship to power and penetration, advised Nicoletta Heidegger, MA, MEd, licensed MFT and sex therapist and host of the Sluts & Scholars podcast. 

Why peg?

Anal sex can feel great, explained Heidegger. There are lots of nerve-endings in one’s anus, especially if you have a prostate. 

Couples interested in pegging may want to expand other creative ways to experience pleasure, she continued, or struggle to feel pleasure on other body parts. Also, if one partner doesn’t want to be or can’t be penetrated, pegging can be another way to connect.

Preparing to peg

Anal sex is different from vaginal sex. While lubricant is a good idea for the latter, it’s absolutely essential for the former. The anus doesn’t naturally lubricate itself like the vagina does, and it’s also not used to anything being inserted in it (quite the opposite!). Therefore, you need to prepare yourself for anal sex. Head over to Mashable’s guide for a full breakdown of how to do so, but here’s some tips from Heidegger and Cuffs.

Talk about your boundaries, said Heidegger. Mashable has a guide to setting sexual boundaries to help out with that, too. You can watch some classes, as well; Heidegger recommends how-to videos at B Vibe and sex educator Luna Matatas’s classes.

Start small. “When you’re preparing for your first anal insertion, start your preparations with smaller butt plugs, beads, and dildos before you try to go for the desired size of your insertable,” said Cuffs. You or your partner’s fingers can also serve as preparation for something bigger, or even thrusting/grinding can get you used to the feeling of something there.

Think about what sensations you’re after when shopping for a dildo. “Some people, for example, love curved insertables and others do not,” Cuffs said. “There’s also a variety of thickness and length to consider.”

If you’re using toys, make sure they either have a large flared base or hold it if it’s not attached to your partner’s harness. “Things can absolutely get sucked into your ass and get stuck. Full stop,” Cuffs warned. “To avoid ending up in the hospital with doctors removing items from your butt, please only use items that have a base or be prepared to hold it the entire time it is inserted.”

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Pegging 101

Go slow and take your time to experiment and see what you like. Don’t try to shove a dildo in there right away — build up to it with fingers and smaller toys. You may not peg your first-ever session; that’s okay.

Decide if you want to clean out the anus (more about that in our guide to preparing for anal sex) or make dietary changes to help with your digestion (@bottomsdigest is a fun TikTok account that discusses this). Be sure to thoroughly clean any toys (and hands) before and after use.

“And of course, use lube!” Cuffs said. “Loads of lube!” It’s a good idea to have other emergency supplies at the ready, too, like wipes and gloves. Heidegger recommends getting a sex blanket as well.

As always, communication is important. Have a safe word, Heidegger said, and make sure you have a way to check-in during sex. Ask each other: what will I see and hear if you are enjoying yourself? What will I see and hear if you’re not?

“Accept that shit can happen!” Heidegger said. We’re only human after all, and we humans have bodily functions. Clean it up and move on.

Heidegger also recommends having an aftercare plan, both for if it goes well and if it brings up feelings. Trying something new in bed can do this, especially if you’re being penetrated for the first time.

With the right preparation, anal strap-on sex can be fun for both partners. Remember to take deep breaths and try to relax — that’ll help your anus relax, too.