My First Pegging Experience: From Nervous to Confident — A Personal Journey of Taking Control in the Bedroom

I never thought I'd be the kind of woman who could 'dominate' a man. I'm super awkward, have zero confidence when trying new sex things — I tend to fumble and giggle my way through them like a total idiot — and always take on the submissive role if I'm given half the chance. But, being in a relationship with an open and adventurous person, and getting comfortable with them in private, has gradually warmed me to the idea of taking control.

At first, we started off small, and I'd tie his wrists and ankles to the bed. Then we took things up a notch, and I felt brave enough to blindfold him. While these things may come naturally to some, to me, they felt like little wins that helped me build my sexual confidence up to where it is today.

Crossing that initial bridge then led us to broadening our sexual horizons in other ways, and as my boyfriend is quite — how to put this — anally curious (he loves anything up there), next-level butt stuff was very much on the cards. Anal sex had been part of our bedroom routine since we first met, so it wasn't something that felt totally out of my comfort zone. If anything, I was quite experienced in that area. We'd always messed around with butt toys, too — our go-tos being classic anal beads and vibrating butt plugs. So, perhaps unsurprisingly, when I suggested pegging, his instant answer was, "Yeah, I'm so up for that."

What is pegging?

You might have guessed it by now, but pegging doesn't have anything to do with hanging up your washing. But you still might need to wash your sheets after — because pegging is a term used to describe "a woman having penetrative anal sex with a man using a strap-on harness," according to psychosexual and relationship therapist Rachel Seymour.

While 'pegging' is usually used to refer to someone with a vagina penetrating their partner (or peggee, if you will) with a prostate, anal sex is obviously open to anyone of any gender. "Since the term pegging was first coined, the usage has become broader and is no longer as cis and hetero exclusive — anyone can peg if they want to!" Seymour explains.

Often, there is a power dynamic to pegging, though, which is why the term has typically been used to refer to someone with a dick being penetrated by someone without. Switching up power dynamics can be incredibly empowering and can give you and your partner a ton of mental and physical pleasure — plus being in charge of the thrusting (and taking control) can be super hot. Oh, as can watching your partner with a prostate unlock a totally new kind of orgasm. Over… and O-ver.

What equipment do you need for pegging?

Before you even think about pegging, you're going to need to do some shopping (God forbid! Don't make us!) — and you'll need to seriously consider some key features when you're buying the equipment for pegging.

"Most of the time pegging will be done with a strap-on harness and a dildo," says Seymour. "There are a huge variety of harnesses available, from ones made from leather and PVC to ones made from cotton that resemble underwear. All harnesses will have an O-ring at the front to put the dildo in; some of them will have interchangeable O-rings so you can use different girth dildos."

The most important thing to consider, though? "Getting one made of a body-safe material such as 100% platinum-cured silicone — other materials like 'jelly dildos' contain tiny pores in the material and can never be properly cleaned, plus they will often degrade over time," Seymour explains.

"The final thing to look for when it comes to dildos for pegging is looking for a dildo with a flared base — this will sit behind the O-ring of the harness and hold it in place during penetration."

Ahead of my pegging debut, I'd kindly been sent a beginner's strap-on and harness. The dildo was a small five inches, very flexible, and not too girthy. As I took it out of the packaging and saw it could fit comfortably in the palm of my hand, I was, rather arrogantly, thinking, 'I could rock that'.

Still, I did feel some nerves ahead of this new sexual adventure. I was also flooded with my usual feelings of self-doubt: Will I actually do it right? What position should we be in? Will I feel like an absolute buffoon when I see myself with a penis? Will he laugh at me? At the same time, I was trying to balance this with my desire to have new and enjoyable experiences.

Needless to say, that strap-on hung, unworn, on the back of my bedroom door for a full week. Every time I left the room, I saw it swinging there by the harness, gently mocking me. 'Not today, Mr Strap-On,' I'd think. 'I'm not quite ready for whatever you've got in store yet.'

How to prepare for pegging

Then, one average Friday night, it happened. We'd just got home after a post-work drink, when my boyfriend said to me straight-up, eyeing the door, "Are you going to put that on and fuck me, or what?" Whether it was his cavalier attitude or the large glass of Merlot taking effect, I suddenly felt ready. No nerves, no apprehension, just a 'fuck it' mentality served with a side of excitement.

By this point, we'd already mentally prepped ourselves for this moment, but if you've never explored pegging, there's a lot that you'll need to do beforehand. Keep reading for top expert tips on how to get ready for being anally penetrated — or anally penetrating.

Communicate

For newbies, pegging is likely going to be a new sensation for you and your partner. Just as when you're considering trying anything new out sexually, having a good chat about what you might and might not like should be the first port of call on the butt stuff boat.

"The most important step to prepare for pegging (both giving and receiving) is to communicate — both with yourself (knowing what you want and what feels good for you) and with one another (sharing your desires and your boundaries)," suggests Seymour.

Explore solo

You're the only person who can truly know what kinds of sensations will feel good to you — so explore anal play by yourself before letting your partner take the reins, as power play can cause emotions to run high.

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"The receiver can explore solo with fingers or toys beforehand," Seymour says. "Many people like to explore solo in the shower — if you decide to do this, you should still use lube when exploring (it's something many people forget! And lube will make any sort of anal play significantly more enjoyable)."

But it's not just the receiver who can benefit from some pegging prep, according to Glickman. "Wearing a strap-on is a different experience for people who didn't grow up with penises, so I recommend they practice wearing it and moving with it by themselves first," Glickman says. "That way, you'll look much more suave."

As for the motion used during pegging, Glickman recommends that the giver steers clear of their natural inclination toward rotating their hips and focus strictly on thrusting in and out. "It's all about the butt and core strength," he said.

Hygiene

Once you're ready to delve into the world of partnered play, it's time to think about prep. Now, don't be freaked out by what we're about to say, but: where there's an asshole, there's a chance of poo. "Regardless of what you do to ready yourself, there is always a (slim) chance of mess, so you should prepare yourself for this possibility and be considerate if it does happen," Seymour advises.

But, if you're worried about that happening, you can clean the area before going in to reduce the chances. "Some people like to douche to feel a sense of security in terms of mess, whilst other people don't feel the need to," Seymour adds. "It all comes down to personal preference."

Either way — hygiene is arguably more important when it comes to anal sex than other kinds of sex, as the skin around the anus is thinner and more prone to tearing (and therefore transmitting diseases) than other areas of the body.

Adding condoms on top of any sex toys you use could prevent spreading unwanted bacteria to the area, and also reduce the need for a clean up afterwards.

Lube up

We've said it a million times; we'll say it again: add lube, and more lube — and after that, add some more. TL;DR: you can never have enough lube, even when you think you do — especially when it comes to anal play.

While water-based formulas are the best option for silicone sex toys, if you're using a condom on top of a sex toy, you could opt for a silicone-based lube, which is compatible with condoms. Silicone lube not only lasts for longer, but is more slippery (AKA ideal for anal sex).

However, some hybrid formulas could give you the best of both worlds, without degrading your sex toys — because (quick lesson, we promise!) silicone lube degrades the silicone in sex toys, making them less safe and hygienic to use over time).

Start slow

Not to be crude, but if you're not the one having something stuck up your ass, you don't get to call the shots. There is often an assumption with power play that the 'dominant' partner gets full, unrestrained power in sexual scenarios — but we're here to break that myth.

Think of boundaries as the key to open the door to exploring power play: the 'submissive' partner, or 'receiver' is the keyholder (though of course both partners can give and withdraw consent at any time), and safewords close the door.

"Make sure to always go at the pace of the receiver, and start small," Seymour suggests. There's no need to go all-in with the dildo straight off the bat.

Don't start with the butt

Before you advance into penetration, you need to get aroused, people! If you've ever had someone penetrate you before you were quite ready, you'll know it's kinda traumatic.

The lesson here is that penetration — of any kind — requires adequate arousal (and your partner's consent!). This is part of the reason why pegging is such a great role reversal; the receiver will truly understand what it's like to be the one on the receiving end. So, before you go anywhere near the butt, get your partner turned on first.

Get warmed up, make sure your partner's feeling ready, and even do some external massage around the whole body (may we suggest a massage oil?) and anus before going inside.

Be patient

It's important to not put pressure on the situation, as this can lead to strain and even injury. "One of the ways you can help your partner is by going into the experience without pushing for a particular outcome," Glickman says.

"If you've been stuck in rush hour traffic or if you're stressed out, your body is going to tighten up and anal play will be more uncomfortable and then it can hurt. The trick is to not create an atmosphere of pressure. Let their body guide the experience so they can relax and be open to it," he adds.

What pegging is really like

So, the time had come to peg my boyfriend. We made out before I steered him to sit on a chair and sucked his cock until he was just about to come. I very cautiously unhooked the strap-on from the door of shame and slipped my legs into it. Reminder for anyone pegging the first time: try that baby on beforehand. Having been helped into it by my colleagues a week before, much to their amusement and horror, I knew what leg to put through which strap. It minimised any potential cringe that could have instantly ruined the moment.

I asked which position he thought would be most comfortable for him, and he laid down on his back with his knees bent, while I positioned myself in between. Not wanting to go straight in there with the strap-on, we fooled around for a bit with a lot of lube and a small butt plug. And when he was ready, he let me know.

Holding the end of the strap-on, I guided it very slowly into his butt with my hand. But then it hit me that the incredibly obvious thing I didn't consider was that this penis was not my legit anatomy, meaning I wouldn't be able to feel a thing. I wouldn't know how deep I was going or whether I was keeping it at the right angle. At first, there was some very on-brand fumbling and a few "oops, soz" moments from me as I entered him. But once he gave me the nod and said it all felt good and comfortable, I finally relaxed.

During our first pegging session, I thought the best thing to do would be to kind of copy my boyfriend when he's on top. I also made a mental note to think about what I knew felt good to receive in that position. Taking it super slow, I thrusted in and out. And from the look on his face, I knew he didn't want me to stop. Next, I tried leaning back on my heels so I could fully see the strap-on gliding in and out. He let out a low moan and I could feel him moving into me, pulling me closer so I was fucking him deeper. It made me instantly wet.

As I quickened my thrusting, I leant forward, leaving enough room between us for him to gently stroke his penis. At this angle, the harness was rubbing against my clit, and with each forward motion, things just felt more intense. He began masturbating quicker, and harder, and I felt myself nearing the edge of an orgasm. "I'm gonna come," he panted.

Lying there afterwards, I snuggled up to him. It's important to get the aftercare down whenever you try something new, especially something that puts your partner in an incredibly vulnerable position. I made sure to ask him how he found it, how it felt, and if he was okay. But he didn't need to say anything — the dopey post-orgasm grin on his face spoke volumes.

I hadn't come. When he'd said he was close, I instantly became so self-aware that my mind was very much not on my orgasm. But that didn't matter at all. We're all so obsessed with orgasm and often make it the 'end goal' of sex when really it's the getting there that's the most fun.

Cringe as it sounds, something as intimate as pegging — if you communicate properly and it's consensual — can really make you closer. He was put in a position of extreme vulnerability and trusted me fully to take control. Plus, watching him masturbate as I fucked him was really, really hot...

Myths about pegging, debunked

After all of that, if you're still left unsure about pegging, or being pegged, we asked the experts to answer your FAQs to dispel some myths and misconceptions around pegging.

Pegging isn't pleasurable for the giver
Wrong! Aside from the mental benefits of role reversal already mentioned, pegging can also be physically pleasurable for the pegger.

A well-fitting harness and a toy that grinds you in just the right spot (i.e. the clitoris), can be very pleasurable.

A good-quality, properly fitted harness has an added benefit as well, according to Ducky Doolittle, sex educator and marketing manager at Blush Novelties. "One of the hardest things about strapping on is that you can't feel your pegging toy like a person could feel if they were penetrating with a penis or even fingers," she says. "You miss out on your partner's signals like muscular contractions. I recommend finding a quality harness that fits well, and harnesses your toy tight against your body. The better the harness fit, the more organic signals you will be able to feel from your partner," Doolittle explains.

Bottom (couldn't help it) line: the more in sync you are with your partner, the hotter your play will be.

Pegging makes you gay

No! One common apprehension about pegging — for both partners, regardless of whether they're giving or receiving — is that wanting to receive anal pleasure means your partner will want anal sex with an IRL penis. But while this train of thought is certainly common, it's totally off-base.

"Who you want to have sex with is your sexual orientation. What feels good to you — that's your body and nerve endings. The two are not related," Glickman says.

It's all about power

Pegging can be fun, sexy, and a little kinky. But it's also much more than that: it can improve the level of connection and empathy between you and your partner.

"A lot of guys say that now they've been on the receiving end, they understand how you can be turned on, super into your partner, and still needs lots of warm up," Glickman explains. "And vagina-owning givers have said, 'Wow, now I understand why my boyfriend gets excited and starts going faster — I did the same thing!'"

"I think the world will be a better place when more men take it up the ass. Once a guy has been on the receiving side of penetration, suddenly he really gets it."