Q. My boyfriend casually mentioned the other day that he'd like to try pegging. At first I was shocked, does it mean he's not sexually satisfied with me? But then I started to quite like the idea of it. The problem is that I have absolutely no idea where to begin. What do I need? How do I do it? And erm, what does it all mean?

To peg or not to peg? That is the question. And what better way to kickstart this new column? For the purposes of giving you advice with as much colour and detail as possible, I called upon a pal, Ruby Rare, sex educator extraordinaire, author and pegging enthusiast, for some back-up.

What is pegging? 

For the uninitiated, pegging is a sexual act that usually involves a cis woman donning a strap-on dildo and making sweet, sweet love to the anus of her partner, who is more often than not a cis male. There are of course variations when it comes to the gender expression and sexuality of participants, though. In Ruby's words: “all are welcome here!” 

At its heart, this sexual practice is about subverting traditional power dynamics and, in particular, challenging the prevailing heteronormative notion that a man is a penetrator and a woman is penetrated. If TikTok is anything to go by, pegging is certainly having a moment right now.

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Now that’s out of the way, I want to preface my advice by saying that the most important factors in sexual experimentation should be clear communication and enthusiastic consent; that is to say, please do be sure to dig into your own feelings about this before diving straight in, so to speak. 

In romantic relationships, it can often be difficult to disentangle your own basic emotions from a desire to satisfy your sexual partner – this is of course extremely normal, but is also something to be conscious of as you work through this idea. And then and only then, proceed only if you are completely comfortable.

As for what pegging might symbolise, there’s a few things to unpack here. But first I’d like to address your concern that your boyfriend wanting to experiment with butt play is a signal that he is in some was dissatisfied with your sex life with some reassurance: I think it is actually quite the opposite. 

For many cis men that have sex with women, anal play is still very much a taboo. And while it may be easy to disregard the reasons behind this – which are most often homophobic and/or misogynistic in nature – the shame that comes with it can be much, much harder to shrug off. So I think it’s important to say that the fact your partner is willing to talk to you openly about his desires without fear of repudiation speaks volumes about the overall health of your relationship. It means he trusts you.

In terms of what it all means, there is no straightforward answer without access to your boyfriend’s thoughts. That said, I would caution against falling down the rabbit hole of trying to ascribe any sort of meaning to it, or to “understand” it, because the likelihood is it that it means very little at all! 

Within the rigid structures of our prudish society, where both gender and sexual roles are fairly narrow and prescriptive, it’s understandable that it might take you some time to digest this idea, if you’ve never come across it before. So go easy on yourself – you’re unearthing some pretty deep mental programming here. 

“Pegging subverts [some traditional ideas around sex], which can be hugely rewarding, allowing women to take ownership of their sexuality, but there can still be shame we have to work through before the fun begins,” explains Ruby.

Though popular for centuries among people of all gender expressions and sexual orientations, it’s a practice that has for a long time been stigmatised and relegated to the shadows. Put plainly, for as long as humans have existed, someone, somewhere has been shoving something resembling a dildo up their bum. 

Why do people enjoy pegging so much? 

So what makes it so pleasurable, I hear you ask? “The glorious prostate!” Ruby exclaims. “It’s a small gland that produces ejaculatory fluid, and is a source of great pleasure. It sits inside the body of men and AMAB folks, and can be stimulated externally through the perineum, or internally through the wall of the rectum.” Sounds great, I say. Ruby agrees. “I genuinely wish I had a prostate several times a day!”

But to reduce pegging to a sex act focused purely on the pleasure of the prostate bearer would be a mistake, says Ruby. “If you’re the pegger, and you don’t have a penis, wearing one is SO MUCH FUN!” And something from which you can learn a great deal too, she explains. “It’s such an interesting experience to get a new perspective on sex.”

Pegging: a how-to

So now onto the (ahem) nuts and bolts of your question. Let’s start at the very beginning: the equipment. You’ll need a dildo that can either be attached to a harness you wear or inserted by hand, depending on how you feel most comfortable.

For the more adventurous, there are double-ended dildos, but let’s start small. If your boyfriend has no previous experience, ”it may be worth focusing on using fingers, butt plugs and smaller toys before working up to a dildo,” says Ruby. 

I’d also recommend looking into anal douching for a potentially less embarrassing first time – depending on what you’re both into – although it’s worth caveating this by saying that the risk of leakages is lower than you might think.

Another thing I would stock up on is lube –  get loads of it. And then get more. However much you think you might need, double it! You can never have too much, in my opinion. Ruby recommends using condoms or gloves on anything going in the anus, as well as stocking up on wipes.

When it comes to positions, Ruby has a recommendation. “I like to start with whoever’s getting pegged on top – that way they can control the depth and movement,” she explains, “plus, it’s really fucking hot watching someone ride you.”

Communication is so important both during sex and afterwards. Many people can feel vulnerable after such an experience, especially those who have never experienced being penetrated before. 

Aftercare (a term from the BDSM community to describe the time and attention you give a partner after an intense sexual experience) can help to ensure everyone feels safe and comfortable; ask your partner what they need, and plan to have enough time afterwards so you don’t need to rush back to anything.

Also, be sure to clean any instruments you use thoroughly, especially if you’re planning to use them with anyone else. Regular soap will do, just don’t put your dildo in a dishwasher like Abby’s character does in Broad City, because that really did not end well.

Most of all, enjoy it! Pegging can be a really fun and empowering way of interacting with your partner that may shift the way you view sex altogether – and the way you view yourself. Better still, being able to share vulnerability with a sexual partner who is non-judgemental, compassionate and communicative can increase intimacy levels, as well as improving your understanding of your own pleasure, and theirs. 

It’s not meant to be scary… just don’t forget the lube!

Ruby Rare’s awesome debut book, Sex Ed: A Guide for Adults, published by Bloomsbury is out now!