What Is Pegging? with Ruby Ryder

Ruby Ryder is a sex educator and sex worker based in California… with a special interest in pegging! It’s fair to say that Ruby is an aficionado and an absolute expert in pegging. And she has dedicated herself to teaching people about it for the last 12 years. 

Her journey began when she started a blog called peggingparadise.com which shared lessons that Ruby learned from her personal experiences of pegging. But two years in she realised that her inclusion of BDSM in the blogs was scaring some people away.

The pegging paradise site was filled with excellent information about pegging, but as Ruby identifies as a dominant sensual sadist, it also featured stories about tying men up, impact play and other BDSM practices.

Ruby wanted to spread the word about pegging to everyone who might be interested, so she began a new website called pegging 101 which shared pegging informational articles – with no kink attached. It has become incredibly popular over the years as curiosity about pegging continues to grow.

I was so excited to have an opportunity to chat with Ruby about pegging… and decided to start with the basics. What I learned in this interview changed my perspective on pegging forever.

What is Pegging?

Ruby explained that the word “pegging” came into existence in 2001 in Dan Savage’s column, Savage Love in The Stranger. Somebody wrote in and asked for a word to differentiate between lesbians and heterosexual people having strap-on sex. People offered suggestions and pegging won. Ruby met the person who had suggested pegging by chance on a Reddit forum and interviewed him on her podcast.

It’s an unusual word, with no obvious connection between the word and the activity, but it stuck.

It was originally a gendered term which meant a woman using a strap-on and penetrating a man anally. But over time, with the gender binaries evolving Ruby prefers to describe pegging as anal penetration using a strap-on dildo, with prostate owners as receivers and vagina owners as givers. 

The receiver has or a had prostate and the giver has a vagina and a strap-on. This definition gives respect to all parties regardless of their genders.

What are the common misconceptions about pegging?

Ruby took a deep breath before explaining all of the many misconceptions, fears, concerns, and assumptions around this sexual activity. 

When a couple decides they would like to explore pegging, it is typically the receiver who discovers that there is pleasure to be had with anal stimulation. The prostate can provide the same amount of pleasure as the g spot. That’s what drives receivers to explore pegging – but they are reluctant to share this desire. 

Ruby explained that this is because of the connotation of receptive male anal play and sexual orientation. She laughed as she said, “asses don’t have sexual orientation!” It makes sense, but there’s no denying that this misconception is prevalent.

I want to explore pegging. But isn’t that gay?

It’s very hard to unpack this connection. A study of the sexual activities of gay men, conducted by George Mason University found that only 36% engage in receptive anal intercourse. A lot of people believe it’s more common than it is.

Yet, when the receiver desires anal stimulation, questions about their sexual orientation almost always come up… from the receiver themselves and also the giver. “Oh, I am a man who feels pleasure in my ass, what does that mean about me?” Ruby says it just means you are a man who feels pleasure in your ass! And, she reminds us that there’s no magic button in the butt that makes receivers suddenly crave the same gender!

Sometimes a man may be bicurious, and in this world, it can be easier to hide that fact. So, can pegging bring that desire out into the open? Possibly. But it doesn’t mean that pegging will enhance this, or create desires that weren’t there in the first place.

Do people want to be pegged because they enjoy pain?

Some people think that pegging is all about pain, but that is inaccurate. Ruby thinks this myth exists because so many people learn about sex through porn, considering it to be education and not entertainment. In porn, anal sex is usually depicted as a man giving it to a woman, and they are typically bad at it and have never received penetration themselves – which is why it’s painful. 

Ruby says, if it hurts, you’re doing it wrong. She insists that people must learn about pegging before just going for it. 

Isn’t pegging dirty and gross? 

It’s true that the area penetrated during pegging is the part of the body where bowel movements come through – but it’s not like ploughing through excrement. The anus isn’t where poo hangs out – it’s the exit valve.

Is it only for people who like BDSM?

This is another misconception from porn, which tends to overrepresent other kinks in conjunction with pegging. Pegging is often depicted alongside the feminisation of the receiver, BDSM, CBT, humiliation and degradation.

Ruby says if you’re into these kinks – great. But the takeaway is that these are not inextricably connected to pegging. 

You can do pegging any way you want. You can even use pegging as another way to sensually make love with your partner. 

Is pegging only for feminine men?

Pegging ties into masculinity issues, because men are expected to behave a certain way in our society. It is forbidden to be feminine or gay. And we have been conditioned to believe that male anal penetration is gay. Being receptive can be considered unmanly. 

But receiving isn’t submissive or feminine. It doesn’t mean that the receiver is not a strong capable provider as a man or a wonderful person.

Does pegging require vulnerability?

Pegging allows receivers to experience the feeling of not being in control, to receive, open up and be vulnerable.

The problem is, that so many people conflate vulnerability with weakness. The expectation is that men don’t show vulnerability or emotions. So, if a giver sees vulnerability in their partner it can be mistaken for weakness. But it’s not that! 

Being open and honest with someone is massively courageous. There is so much for the receiver to let go of, to surrender. They are required to reconcile their own connection to their masculinity… and then let their partner in too. And all just to stimulate a part of the body that feels pleasure.

The work that is required to be vulnerable to that degree can transform the receiver. This can help men to break out of the “man box.”

Is it safe to bring pegging into hook-up sex?

For people who are new to pegging, it is helpful for the giver and receiver to have a connection, although that doesn’t necessarily mean a relationship. There needs to be a degree of trust, as emotional stuff can come up.

How can receivers introduce the idea to their partner?

Communication is key! Communicating openly beforehand clears up so many issues, calms both parties, and starts you off at a great place, where there are no unspoken fears in the background.

Ruby has 2 podcast episodes dedicated to answering this! One from the perspective of the giver and one from the perspective of the receiver. 

What’s the best part of pegging?

Ruby truly believes that pegging can save the world. 

Prostate stimulation can be considered the peak of male pleasure. It can be 10x as pleasurable as penile stimulation alone. No wonder so many people want to explore this.

“It allows you to experience sex from the opposite side of the bed. You have the experience of taking on your partner’s typical usual role. So it’s educational, fascinating and magical. Developing an understanding of and compassion for the partner’s usual role builds a deeper intimacy.”

Ruby also says it is educational for the giver too. “Many women don’t have a clue what it takes to fuck somebody! It requires strength, balance, endurance, grace, and multitasking! You will use muscles that you’ve never used before. And there’s an element that we won’t understand – because we don’t have to worry about having the right amount of arousal to keep hard, while not too much so it ends early. It’s an athletic event!

When you strap it on and “do your partner” it can blow your mind – and you will have so much more respect for the cock owner in your life. Maybe more understanding for those times when they say they’re tired.”

Ruby even has an article on all the exercises that she recommends to keep givers in good shape to help them to build pegging stamina! 

She says that it can feel incredibly empowering for the giver. But, of course, givers are all different kinds of people. Some may be foundational dominant, and some may not.

Is there pleasure for the giver?

There are different kinds of pleasure for givers. Sure, it takes a lot of effort and there is a steep learning curve, so they may need to build up their stamina. But givers enjoy pegging for various reasons.

Running the show and being in control may appeal to some people. 

There can be pleasure in the giving of pleasure – much like giving oral sex. Ruby takes great pride and delight in turning my partner into a trembling pile of speechless flesh!

There’s also a wide array of equipment that is designed to give the giver pleasure too. You can match the equipment with how you usually get off – for example grinding or clitoral vibrations.

Ruby teaches 3 online webinars and one of those is dedicated to the discussion of equipment.

How can I peg my partner without hurting them?

When starting with pegging, receivers suddenly learn that foreplay is more than 20 seconds of can I put it in yet! Here are Ruby’s tips.

• Receivers should try solo play first as this reduces anxiety for all partners. It allows the receiver to direct the giver. If you know you’ve already had something in there of a certain size, then you know you can do it again.
• Lube is critical because the ass is not self-lubricating. 
• Foreplay is the first full act of the play. Spend time playing there and exploring until your partner is literally asking for it. 
• Go slowly and let the receiver’s body relax.
• Communicating is essential. If you’re a couple who don’t talk in bed, you’re not ready to try pegging. Communication is so important, especially when you’re exploring new territory.

Conclusion

It’s clear that Ruby is deeply passionate about dispelling the myths surrounding pegging, and a big part of that is because of the potential that it has for bringing couples closer together. A big takeaway for me was realising the courage required to explore this aspect of pleasure. Pegging is one more tool to put into your pleasure chest of choice, and even if it doesn’t work out, it can still be incredibly bonding. 

If you would like to learn more about pegging, Ruby has many free resources available. 

She teaches webinars for free and is working on recorded versions that will be available to purchase for on-demand viewing. You can find Ruby on the links below.

LINKS

Ruby on TikTok: https://www.tiktok.com/@peggingparadise

Instagram: https://www.instagram.com/rubysworldofnoshame/

Twitter: https://twitter.com/Ruby_Ryder

Reddit: https://www.reddit.com/user/RubyRyder/

Podcast: Ruby Ryder’s Pegging Paradise: https://podcasts.apple.com/us/podcast/ruby-ryder-pegging-paradise/id569410141

Subscribe to my podcast: https://podcasts.apple.com/us/podcast/in-bed-with-lisa/id1607881950

Subscribe to my YouTube Channel: https://www.youtube.com/channel/UCCEWC8f4QcA6PPrTMF-z3fw