A Hole New World — How To Take The Next Step In Anal Play To Pegging

Butt stuff. Whether it comes in the form of fingering, using anal toys like butt plugs, or using your tongue to ‘rim’ the anus, it’s an area of sex that has a tantalising air of taboo around it. This is particularly the case when hetero and hetero-passing couples decide to try spicing up anal sex for the first time by swapping the penetration dynamic between partners!

The term ‘pegging’ was first coined in 2001 by sex advice columnist Dan Savage, and at the time, it was used to refer to the act of a cisgender woman using a strap-on dido to penetrate the anus of her cis male partner. These days, the definition of pegging is more inclusive and covers all vagina-having folk penetrating all penis-having people too.

The main ‘stigma’ around pegging comes from the fact that it subverts gender norms and flips the script of penetrative sex by putting the traditionally penetrating partner (the one with the penis) in the penetratee’s position. Many vagina-owners get aroused by the idea of being the dominant one over their partner, and vice versa for the receiver — not only is this emotionally and mentally hot AF for some, it’s also a great way to unlock a prostate orgasm for the receiver! During pegging, a dildo has the ability to reach and massage this walnut-sized gland, which sits between the base of the penis and rectum and is sometimes referred to as ‘the male G-spot’. A prostate orgasm is usually more intense than a regular penile orgasm thanks to the massive density of sensitive nerves that are packed into the anus, so it’s safe to say that the physical sensations of pegging are also a huge draw for the pro-pegging crowd!

How to prepare for anal sex if you’ve never tried pegging before

Of course, you can’t just jump into pegging without proper preparation. As always, informed consent and open communication will help you and your partner better understand what you’re hoping to get out of the experience and what your boundaries are. Safety should always be your top priority as well, especially since the anus is naturally full of bacteria and is not a self-lubricating canal like the vagina. This means it’s easier to injure during sex without proper prep and care. Keep condoms, toy cleaner, and lubricant on hand to ensure your equipment is always ready to rock and roll.

Keep things slippin’ ‘n’ slidin’

At a minimum, a good-quality anal lubricant is an absolute must. Something with a thicker, more viscous texture like the Wicked Jelle Water-Based Lubricant will provide a cushioning effect and a long-lasting glide for maximum comfort during play. Sexyland recommends anal lubricants without numbing ingredients so you can check in with each other that the receiver is not in pain, as this is indicative of the dildo being too big, things moving too fast, or not having enough lubricant. When performed correctly, anal sex should not hurt if everything is going at a suitable pace with an appropriately-sized toy and the right amount of lubricant.

Clean up before having company over

The person being penetrated may want to cleanse themselves internally beforehand to ensure a hygienic experience that’s also free from any awkward moments for themselves and their partner. An anal douche is perfect for standard cleansing and is easy to use shortly before beginner-friendly backdoor play, whereas an enema is better for intensive cleaning before more hardcore play.

Start small before going big

Going slow and starting small is important when it comes to anal play, so don’t skip the foreplay! A lubricated finger or enthusiastic tongue for some rimming fun will help the receiving partner relax and get ready for penetration. Anal training is also something the receiver may want to consider to work their way up to being able to accommodate a dildo — anal training kits come with a series of butt plugs and anal probes in graduating sizes so you can make progress at your own pace and be comfortable every step of the way.

Have the right gear ready to go

For the penetrating partner, there are several types of strap-on and accessories to consider to find the one that suits you and your playmate best:

Strap-on harness

This is the classic set-up that comes to mind first for most people when they think of strap-on sex. The straps can be a little fiddly if you haven’t worn one before, but this style of harness makes up for it with the fact that the waist, hip, and thigh straps are adjustable so you can always customise the fit to your body perfectly!

Underwear-style harness

For something that’s easy to just put on and play, an underwear-style harness is the perfect choice. Just slip it on, slot the dildo into the O-ring, and away you go! You can also get an underwear harness with a dildo included, like this Scandal® Pegging Panty Set.

Strapless strap-on (double-ended dildo)

If the penetrating partner has strong kegel muscles, this toy offers double the fun if both people want to be penetrated! The short end goes inside the wearer’s vagina where they use their pelvic floor muscles to hold onto the bulb while thrusting the longer end in and out of their partner. There are vibrating options, options with clitoral suction for the wearer, and many more, so there’s always something to ensure you can play your way!

Anal dildos/probes

Dildos come in all sorts of shapes, sizes, and textures, and with enough experience, you can feel free to experiment with plenty of interesting designs when you’re ready. For beginners though, Sexyland recommends anal toys on the smaller end, with a slim, tapered shape that’s easy to insert. A curved shaft can also help target the prostate better, such as these petite beauties from the Malesation pegging dildo range. As long as the toy has an appropriately-sized suction cup at its base, it will be compatible with strap-on harnesses and underwear-style harnesses so you can explore the wide range of dildos together!

Ready to take the next step in anal play with your partner? Check out strap-on harnesses, dildos, butt plugs and more at Sexyland’s adult stores or shop our range of anal toys for beginners online! You can always chat to our friendly Fun Specialists for personalised advice on how to live your best sex life.