This pegging guide is written for anyone interested in learning more—gender and/or sexual orientation are irrelevant, as is previous experience of pegging. If you’ve never done it before then we’ll help you take the first steps as safely as possible with some pegging advice, and if you’re more experienced you’ll hopefully still get some new hints and ideas for your sexy fun. We’ll look at toys and techniques as well as suggestions for how to make the experience as enjoyable as possible for everyone involved.
What is pegging?
‘Pegging’ is a term originally used to describe a man being anally penetrated with a dildo by a woman. These days it’s generally accepted to mean anyone being anally penetrated with a dildo by a partner of any gender. That said, in order to keep this article reasonably coherent, we’re going to stick with the OG ‘bend over, boyfriend’ combination of a man being penetrated by a woman. Your mileage may—and probably will—vary, but the pegging advice, tips and techniques here can be adapted for pretty much any combination of partners. So strap in, strap-on, and let’s dive in to the FrolicMe guide to pegging!
Beginner’s guide
Are you an absolute beginner when it comes to pegging fun? Nervous about the basics? We got you covered, think of this as a beginner’s guide to pegging—all welcome! You don’t need to have any anal experience before giving pegging a go—it’s perfectly possible to have a fun and sexy time of it regardless of prior adventuring (or not).
Why try pegging?
Let’s start from the bottom up (sorry)—why do some men want to experience pegging, even if their sexual orientation is as straight as a die? There are several reasons for this—some physical and some psychological. The most obvious one is that the anus is incredibly sensitive. The skin around it responds to the lightest touch and the stretching sensation caused by pushing something into it—whether that be a finger or a dildo—also triggers nerve responses. The idea of being penetrated can be an incredible turn-on to someone who would usually be the one doing the penetrating. There’s very good reason why so many role-playing games involve [handing over] control. If a man has only ever had the sort of sex in which he is the one penetrating his partner, then it might well be incredibly exciting for him to think about the idea of being dominated by someone else. Swapping roles so that the woman is—literally—on top, in the ‘giving’ rather than ‘receiving’ position, can be one hell of a power trip for both partners.
It’s also undeniable that anal sex—when done carefully and safely—can be a genuinely physical turn-on for those with a male anatomy. The prostate is a gland, around the same size and shape as a walnut, that sits between the anus and the penis, just a couple of inches inside the anal cavity. As it already plays a large part in the process of ejaculation, it doesn’t take too much effort to learn how to stimulate the prostate enough to cause orgasm, even without penis stimulation. In fact it’s often called the P-spot, because the effects of stimulation are similar to that of the G-spot in those with a vagina.
Many women are fascinated by the idea of reversing the sexual roles with their male partners. In the same way that men might find it exciting to be dominated for a change, women often enjoy the idea of being an active partner. The role of penetrating is a completely different mindset to that of being penetrated. and the control alone can be a huge turn-on. A large proportion of men who are interested in the idea of pegging are cishet males with cishet female partners—wanting to change things up doesn’t denote a desire to change sexual orientation. This activity can be fun for anyone, regardless of sexuality or gender.
How to prepare
PREP-TIME. Whilst it’s a relatively simple technique to learn, pegging does require some advance planning. Although it’s possible to peg with a standard dildo, it’s very difficult to keep a rhythm up whilst holding it in your hand. And you absolutely must either have a flared base, or a very good grip, you do not want a dildo ‘getting ‘lost’. The best option is a strap-on harness, which holds a suitable dildo in roughly the same place a penis would be if the wearer had one. Not all harnesses are the same! Of course it’s fine to look at the lower end of the market if you just want to give it a try and think you’ll maybe never do it again, but regardless of the price-point, take some time to make sure the harness fits properly. Cheaper materials are more likely to chafe the wearer, especially if they don’t fit very well. If you can justify the cost, look for something in the mid-market range. All you need is enough strapping to make the harness fit properly, made of material that won’t stretch, snap or scratch. Many mid-range harnesses are now made in a pleasantly soft faux leather, often with padding behind the dildo attachment. And while we’re talking attachments—learning about pegging is often a lesson in just how different dildos can be. Most harnesses have a metal O-ring, through which the flared base of the dildo is pushed until it pops securely into place. But not all O-rings are the same size, so it’s worth double checking that your chosen harness and dildo will match up, before spending too much money.
If the receiving partner is new to pegging, start small. Many manufacturers make ‘beginners’ dildos these days, often tapered for easier insertion. If your harness has a standard-sized O-ring you can always size up later if both parties are keen. And don’t forget the lube! Lubrication is essential for pegging, in the same way it’s always needed for anal sex, regardless of who’s doing the giving and receiving. The anus doesn’t lubricate itself and the skin around the sphincter muscle is delicate and very easy to tear. Water-based lubricants are safe with pretty much any dildo and unlikely to cause allergic reactions.
If you’re going to be the person wearing the harness, don’t rush things when putting it on. It often takes some wriggling around to get a harness to fit comfortably. Adjust the straps so the dildo won’t drop away from your body, but don’t pull them so tight that you struggle to move! Time taken now will be well worth it in the long run. Pegging should be enjoyable for both parties, and that means making sure you’re both comfortable from the start.
Because pegging involves inserting a dildo into the man’s anus, he should prepare in the same way anyone would for anal sex. Whether you’re male or female, your digestive system ends with not one but two sphincter muscles—the external one at the rectum, and a second a little way up inside. These two muscles create the ‘anal cavity’. The anal cavity is empty, apart from those times you feel the urge to go to the toilet. That feeling of pressure is caused by body waste moving down into the cavity, ready to be expelled. So unless you have a stomach upset (in which case anal sex isn’t advisable anyway), the likelihood of making a mess is minimal. That said, all humans have bodies and those bodies have bodily functions, some of which get messy with little warning. You might feel more relaxed if you cover the bed with an old sheet or towel. Even if no accidents happen, it’ll save you having to wash lube out of your best bedsheets (we’re not kidding about this—if you want to try pegging then lube is about to become an integral part of your sex life, whether you like it or not). If you’d rather go for the super-safe option and clean things out a bit first, then buy a simple anal douching kit and read the instructions before using it. Such kits are perfectly safe if you’re careful with how you use them, but you don’t want to risk either upsetting your body’s delicate internal bacteria, or damaging fragile mucus membranes.
How to peg someone for the first time
The main thing to remember from this first time pegging guide, is to relax. As with any more advanced sexual technique, if one partner has previous experience and the other doesn’t, then everything needs to proceed at the beginner’s pace. Foreplay is still important—both of you will get far more enjoyment out of the experience if you’re feeling turned-on and ready to go. If you’re the person doing the pegging, try teasing your partner’s anus with a well-lubricated finger, swirling around the rectum and sliding down along the perineum slightly. You can then try sliding a finger gently inside, to encourage your partner to relax into what is likely to be an unusual sensation for them. Consider agreeing a safe word—something completely unrelated to sex, such as ‘banana’—so your partner feels secure in the knowledge they can stop at any time. And think about what position you both prefer. The obvious option is for the man to get onto his knees and lean forward down onto the bed, with the woman kneeling behind him in a role-reversed doggy-style. This often works well, but because of physical size differences, it can be difficult to achieve the correct angle for penetration. If this happens, the man can help by lowering himself down so that his bottom is sticking out over his heels. Some people prefer to try new sex techniques on the floor with cushions or blankets as padding, because there’s less chance of wobbling.
If you’d prefer more intimate connection, then the man can lie down on his back and pull his knees up towards his chest, with the woman kneeling between his legs. This position allows for eye contact as well as kissing, both of which can help increase the feeling of closeness.
When you’re both feeling comfortable and ready, apply plenty of lube to both the dildo and the man’s anus. As before, you can use your fingers to tease his anus before slowly inserting just the tip of the dildo. Ask him how he feels before pushing any further in. Some people like the feeling of the dildo pushing fractionally in and out for a while, just to get used to the sensation of being stretched. Others find this uncomfortable and prefer continuing gradual insertion. So long as it works for you both and everyone’s happy, there is no set way of doing this—personal experimentation is everything. Remember—no matter how turned-on the receiving partner might be, the anus does not self-lubricate! So keep that lube tube handy and reapply regularly. This is definitely a time when there is no such thing as ‘too much’ lube.
If you’re the giving partner and this is your first time pegging, don’t worry too much about technique. Men have been learning to thrust since pretty much the minute they discovered what an erection was—it’s likely to take you a while to figure it out for yourself. Try pushing steadily until your bodies are against each other. If the man is on his back, you could try stimulating his penis at the same time—many men report having incredibly intense orgasms from masturbation whilst being pegged at the same time. If you’re going with the doggy-style position—the angle of penetration means this is often a really good way of stimulating the prostate gland. The man can alter the angle of penetration slightly by moving his knees up (deeper) or down (more shallow) if he’s on his back, or do the same by changing the arch/height of his bottom if he’s on his knees.
Pegging tips and tricks
Let’s take a minute to remind ourselves of the tips for first time pegging. Comfort, communication and lubrication are the keywords, and they really are all as important as each other. Take things slowly and remember to tell each other what you’re enjoying about the whole experience. Lubrication is everything, and with lubrication comes comfort. And don’t fret at this stage if things don’t go entirely to plan! It takes a while to get the hang of new techniques, whether in or outside of the bedroom. One or both of you might decide you’re really not keen after all, and that’s absolutely fine. Healthy attitudes towards sex include accepting that not every sexy variation suits everyone. If you try any of these pegging tips and tricks and don’t like it, then hey—at least you tried it! And now you know what you don’t like, you can get on with discovering what you do.
Expert’s guide
But what if you try it, both like it, and want to explore some more? Let’s move on to the expert guide to pegging, for those looking to take things that bit further.
Pegging more often
Practice makes perfect. The more you indulge in pegging, the more you’ll get to know what both partners prefer, from dildos to positions and everything in-between. The person being pegged can practice anal training—whether alone, or with a partner—with butt plugs and other anal toys. This helps them get used to the sensation of the sphincter stretching, and can help make pegging sexier than ever. It is perfectly okay to use standard dildos for this if you fancy, but make sure you only use toys that have enough flare at the base to prevent them sliding completely inside. There’s nothing sexy about spending an evening in an emergency room with several amused medics looking at your naked rear end. And never use toys vaginally after they’ve been inside the anus. Unsurprisingly, the anus contains bacteria that can cause really nasty vaginal infections, so always keep toys separate. It’s generally better to buy dildos made specifically for anal use. Many manufacturers now produce boxed sets of several dildos, which start at a relatively small diameter and build in size as you work through them.
Trying different dildos
Once you’re used to the feeling of anal toys, think about how you might change the sensation. Increased circumference will have more effect than extra length—it’s the area around the sphincter muscle that has the most nerve-endings. Dildos come in all shapes and sizes these days and different textures will give different sensations. Harder surfaces will give a more intense sensation than those with more ‘give’ in them, as will rippled textures. You can even buy dildos made from glass—and no, they won’t break inside you—so long as you buy from a reputable source, all glass used in sex toy manufacturing is fully toughened.
Advanced strap-on harnesses
Although most strap-on harnesses are fairly similar, some offer added extras. One of the most common additions to a harness is a pocket for a bullet vibrator. Although these are usually positioned to stimulate the wearer rather than the receiver, the vibrations are often strong enough to be felt by both. Try pushing deep inside whilst wearing a bullet-vibe harness and holding still, pressed against each other.
Other harnesses might have a dildo attachment for both partners, one for the female partner and another for pegging. These can be slightly complicated to figure out, but you’ll definitely have fun trying!
There are grinding attachments available to allow for clitoral stimulation while pegging—these are placed on the base of the dildo within the harness and can really enhance pleasure for the wearer.
Pegging FAQs
Does pegging hurt?
Does pegging hurt? Not if you’re doing it carefully and thoughtfully. But there’s no denying that anal penetration can be a very strange feeling for the receiver if they’re not used to it. This is why we always recommended starting slow and building things up gradually. Similarly, harnesses can feel awkward to begin with. Make sure yours fits properly and is adjusted so it doesn’t pinch in places it shouldn’t. It can also take some time to adapt to having an appendage on your body that you’re not used to! Many women find it enjoyable to take some time getting used to wearing the harness, lubricating the dildo and using a hand to caress it and get to know how it feels.
Does getting pegged hurt?
If you follow our hints and tips then no, getting pegged shouldn’t hurt. As we’ve already said it might be uncomfortable until you’re used to it, but it shouldn’t cause actual pain. If it does, then something needs adjusting—maybe more lube, or a smaller dildo. You might just need longer to get ready, both mentally and physically. Make sure you tell your partner how you’re feeling and what you’d like them to do. This is supposed to be enjoyable—if it isn’t at any point, then stop. You can always try again another time, if necessary. And you might simply decide you’re not keen at all! It’s fine to try something once and then decide not to do it again.
How to peg a guy safely
If you want to know how to peg a guy and you’re the one doing the pegging, always listen to your partner and (if your position makes it possible), watch their facial expressions. This will help you both feel confident in the knowledge you’re pegging safely. Ideally you’ll have already agreed a safe word so you’ll know when to stop, but if you haven’t then be aware of your partner’s reactions. If they look uncomfortable at any point, stop what you’re doing and ask them how they’re feeling. They might need you to change position slightly, or just not push in so deeply. Take a break, if needs be—withdraw slowly and ask your partner how they’re feeling. Don’t be tempted to just hammer away—never forget that the anus isn’t the same as a vagina and won’t lubricate itself. If in doubt, the answer is almost always: apply more lube!
Starter kit
Compiling a pegging starter kit: The absolute basics are a suitable dildo and plenty of lube, but for fun and safe pegging it’s best to go with a harness attachment.
Strap-on harness
A strap-on harness is literally what it sounds like—a body harness made from strapping that holds a dildo onto a woman’s body in approximately the place a penis would be if she was a man. Many come with dildos included, but they tend to be a standard middle size—you may need to swap this out for one with a smaller diameter, at least to start with. If the harness doesn’t come with a dildo then check the size of the O-ring before buying one to ensure compatibility.
Strap-on dildo
Check the size of the O-ring (it should be on the packaging) and make a note—you’ll need it for dildo-shopping. If you buy a dildo with a too-small base diameter, it will slide out of the harness (usually at the most inconvenient moments)—too large, and you won’t be able to attach it in the first place. Suction-cup dildos often fit into harnesses, but it can be trial and error to find ones that are compatible. Keep an eye out for more slender dildos, at least to start with. For fairly obvious reasons, the final choice should always lie with the person who’ll be on the receiving end!
Lube
Lubrication is the key when it comes to safe pegging. The sphincter is a tight muscle that takes persuading to relax and open up—the more lubricant you use, the easier this will be. Friction isn’t fun in this case. Lubricate both the dildo and the anus before starting, and keep the lube handy so you can add more as and when needed.
Anal training kit
If you’re the receiver and you’re not sure how you’ll get used to the sensation of being pegged, you might want to think about purchasing an anal training kit. These contain a range of different-sized butt plugs, from slender upwards. That way you can practise with the smallest one—perhaps even alone, until you’re feeling more confident—and gradually build your way up. If, when you’re more experienced, you feel you’d like to train yourself to accept larger dildos, you can keep increasing the size. And for those who really want to push themselves, anal dilators—think ‘butt plugs with attitude’—are sold in similar graduated sets.
Prostate vibrator
Whilst not technically used for pegging, those men who find they enjoy internal stimulation might want to try out prostate massage. There is now a wide range of ‘P-spot’ insertable vibrators on the market and they come in various sizes to suit all requirements. The advantage of these toys is that they can be used either alone or with a partner and can help men locate their prostate and learn how to stimulate it. Such vibrators can, with practice, be used to trigger orgasm without even touching the penis.
Advanced pegging advice
Enjoying pegging your man but looking to step things up a notch? Let’s look at how you can continue your anal adventures whilst making sure it stays enjoyable for all concerned.
Anal training progress
The most obvious change you can make to your pegging fun is to mix up the type of toys you use. As already mentioned, dildos give different sensations depending on how they’re designed and what material they’re made from. Practising with butt plugs will help train ‘muscle memory’ and allow for easier insertion of dildos, but as they stay in one place once inserted, they’re going to feel very different from a strap-on dildo that’s being used for anal sex during pegging. Look for butt plugs with different dimensions—some even have bullet vibrators inside them to add extra stimulation—and try dildos with different textures. After all, variety is the spice of life! The main thing to remember is lube, lube, lube—make sure it’s good quality and use plenty of it.
Different dildos
If you’ve bought a strap-on ‘kit’, then it probably came with a generic dildo in the shape of a fairly average penis. With luck, the O-ring on your harness will be compatible with many of the endless range of dildos on the market, so feel free to try different types. If the receiving partner would like a more intense experience, try bigger dildos, perhaps made from harder materials. The less ‘give’ in the surface of the dildo, the more intense it will feel to the recipient. If they’re not keen on the bumps and ridges designed into most penis-style dildos, look for a smoothly tapered replacement. And think about trying one that bends at a slight angle towards the tip, in order to more easily stimulate the prostate.
When you’re pegging someone, you don’t have to just keep doing the same thing all the time. Once you’ve had time to establish your favourite attachments—and how to get them on and off without too much wrangling—try swapping to different dildos throughout your session, in order to change the sensation for the receiving partner.
Add vibration
Adding vibration really is one of the easiest ways of making sexperimentation more intense. As mentioned earlier, many butt plugs now come with vibrating options. Or use a standard vibrator around the man’s anus and perineum in order to stimulate the nerves ahead of pegging.
Top Tip: put a condom on it if you’re going to be using the vibrator vaginally afterwards, to avoid cross-contamination—that way you can dispose of the condom afterwards and not worry about bacteria.
We’ve already talked about stimulating the penis during pegging, but how about adding a vibrating cock ring? Anything that increases sensation will add to everyone’s fun. In the same way, if the person doing the pegging has a vagina, they might like to try ‘double’ strap-ons that penetrate the giver as well as the receiver. It’s even possible to buy pegging dildos that look similar to standard double-ended dildos, but which have one end angled to slide inside the vagina in order to ‘hold’ the pegging end. Some harnesses have pockets for bullet vibes to give clitoral stimulation to the ‘giving’ partner. Or maybe try wearing a butterfly-style vibrator underneath the harness. Suction base dildos can allow for a grinder attachment for the wearer to rub against for direct clitoral stimulation while they penetrate. Doubled up with some bullet vibrations, this can really be an intense and very exciting experience.
Types of lube
We keep going on about the importance of using lube, but which type is best? Although silicone-based lubricant is one of the most commonly available lubes on the market, it can and will damage sex toys (which are mostly made of silicone). It might sound counterintuitive, but putting two silicone-based products together causes a molecular reaction that almost always ends in disaster for the sex-toy involved. Water-based lube is almost always the best option for most sexual activity, including pegging. Yes it sometimes feels overly sticky to the touch, but it won’t react with anything (and will easily wash out of your sheets). More and more manufacturers are bringing out ‘natural’ lubricants these days, as well as hypoallergenic and organic options. Be careful when using fully natural products such as coconut oil, which can damage both sex toys and condoms. Go water-based and you won’t regret it, you just might have to re-apply more often.
Confidence & communication
The most important thing when approaching any new sexual activity for the first time is communication. Talk to each other and say what you each like and don’t like. Don’t rush into anything, and definitely never try to rush your partner into something if they’re not absolutely sure they want to try it. But if you’re the person being pegged and you realise you really do enjoy it, let your partner know! There are endless variations of the pegging technique to explore. Or think about other types of anal and/or prostate play you might enjoy, and discuss it with your partner.
Making progress together
If you’ve got this far, then hopefully you’re now reasonably confident with the idea of trying pegging—or expanding your repertoire, if you’re starting from a position of more experience. Pegging is a fairly advanced sexual activity that can take quite a bit of practice to get right for both partners, but it isn’t a race. The active partner will develop their technique as time goes on, and also hopefully find ways of stimulating themselves at the same time. The receiving partner can enjoy the change of sexual dynamic and learn which equipment and techniques give them the most pleasure.
Most importantly, pegging is something that has to be done in partnership, in order for it to work. Remember to keep talking and exploring and finding out what both of you enjoy, and you can’t go wrong!