Strap-on sex isn’t defined by gender, sexuality or who usually does the penetrating.

People of all genders, bodies and relationship types enjoy strap-on play — for pegging, vaginal or anal penetration, power play, gender affirmation, role reversal, or simply because switching things up can feel really, really good.

And at Sh!, we’ve been talking about strap-ons for a very long time.

Back in January 2005, we shared our strap-on expertise with Scarlet Magazine, at a time when the mainstream press still regarded a woman strapping on a dildo to penetrate her male partner as rather revolutionary.

A lot has changed since then — thankfully! Strap-on play is far more openly discussed, our understanding of gender and sexuality has evolved, and pegging has well and truly entered the pleasure mainstream.

But some things haven’t changed at all: choosing the right harness and dildo matters, lube is essential for anal play, communication is everything, and nobody should expect to be a strap-on superstar on their first attempt.

So, we’ve delved into the Sh! archives...

Who Can Enjoy Strap-On Sex?

Anyone who wants to.

Strap-ons have long been associated with lesbian and queer sex, but there has never been a rulebook about who gets to wear one — or who gets to enjoy being penetrated by one.

Today, strap-on play can encompass all sorts of pleasure. You might want to experience being the penetrating partner, explore being penetrated yourself, play with different power dynamics or discover sensations that aren't possible with your usual sexual repertoire.

For people without a penis, wearing a strap-on can provide the experience of penetrating a partner while leaving both hands free for touching, teasing and extra stimulation.

For the receiving partner, a dildo can provide vaginal or anal stimulation — and for people with a prostate, anal penetration can also provide targeted prostate pleasure.

Whatever your bodies or identities, the important question isn't who is supposed to do what?

It's what would you both like to explore?

What Is Pegging?

Pegging is anal penetration using a strap-on dildo.

The term was originally popularised to describe a woman using a strap-on to penetrate a male partner, but today you'll also hear it used more broadly when people talk about strap-on anal play.

For some couples, the appeal is physical. The anus and rectum contain lots of sensitive nerve endings, and people with prostates can enjoy additional stimulation from a suitably shaped dildo.

For others, switching who penetrates whom can be an exciting change in sexual roles or power dynamics.

And for plenty of people, it's simply another way to share pleasure.

From the Sh! Archives: One Couple Tries Pegging

Back in 2005, Scarlet Magazine asked a woman and her male partner to try strap-on sex and report back.

Their language and expectations very much belong to their era, but their experience captures something we still tell first-time peggers today:

Expect experimentation. Communicate. Use plenty of lube. And don't worry if you don't get everything right first time.

She Says...

Her first worry was hygiene. After doing some research, the couple prepared themselves, put down a towel just in case and went looking for a dildo that felt neither too big nor too small.

Her first attempt at wearing a strap-on wasn't exactly the powerful erotic transformation she'd imagined. In fact, she felt decidedly silly.

They initially experimented with a strapless strap-on, hoping the closer body connection would work for them. In practice, keeping the toy securely positioned while also trying to penetrate her partner proved frustrating.

So they stopped.

After a cup of tea, a cuddle and a rethink, they tried again with a conventional harness and dildo.

This time, things clicked.

With her partner lying on his back, she found it much easier to control the dildo, experiment with thrusting and see how he responded. The experience became far more pleasurable once they stopped worrying about performing and found a set-up that actually worked for their bodies.

Her biggest takeaway?

Strap-on sex takes practice. She wanted to move faster and more confidently than her partner was ready for, while he needed her to slow down and give him time to adjust.

Not getting it perfect first time wasn't failure — they were learning how to do something completely new together.

He Says...

For the receiving partner, the prospect of being penetrated with a strap-on brought a mixture of excitement and nerves.

They started gradually with plenty of lube and manual anal play before moving onto the dildo.

Finding a comfortable position took several attempts, and those unsuccessful starts left both partners feeling self-conscious. Eventually, however, they found an angle that worked while also incorporating external stimulation.

The result was an exceptionally intense orgasm and a rather different sexual experience from anything he'd tried before.

His conclusion was refreshingly practical: expect some trial and error, prepare properly, use the right toys and don't be stingy with the lube.

Nearly two decades later, we'd still agree.

Getting Started With Strap-On & Pegging Play

Your first strap-on experience doesn't need to look anything like porn — and you certainly don't need to instinctively know what you're doing.

Operating a dildo attached to your pelvis is a new physical skill. It can take a little time to work out positioning, angles and movement.

Likewise, receiving anal penetration is something the body should be given time to prepare for.

Start with conversation rather than penetration. Talk about what you're curious about, what you'd like to try and anything that's off the table.

If you're exploring anal play for the first time, warm up before reaching for your strap-on. Fingers or smaller anal toys can help you discover what feels comfortable.

Then take your time.

There are no prizes for speed.

1. Choose a Strap-On Harness That Fits

A good strap-on harness should feel snug and secure without digging in or restricting movement.

A well-fitting harness keeps the dildo stable and gives the wearer much better control over its angle and movement.

Adjustable strap-style harnesses are particularly versatile because you can customise the fit and, depending on the design, change the O-ring to accommodate different dildo sizes.

At Sh!, many of our leather harnesses are handmade by our team and designed to be mixed and matched with different dildos.

This means you're not stuck with the dildo that happened to come attached to your harness. Start smaller and change your dildo as your tastes and confidence evolve.

2. Start With a Smaller Dildo

One of the most common mistakes first-time peggers make is choosing a dildo that's too wide.

When it comes to anal play, girth matters.

A dildo may look relatively modest in your hand but feel considerably larger during anal penetration, so there's absolutely nothing wrong with starting slim.

Length is more flexible because you control how deeply a dildo is inserted. Bear in mind that some usable length is also lost when the dildo is fitted into a harness.

Our Sh! silicone dildos come in a wide range of lengths, widths, shapes and textures, and their wide heart-shaped bases make them compatible with our strap-on harnesses.

You can start small and switch things up later.

3. Choose Body-Safe, Anal-Safe Toys

Anything inserted anally needs a secure flared base or handle to prevent the toy travelling further inside the rectum than intended.

Our handmade Sh! dildos have wide heart-shaped bases, making them suitable for both harness use and anal play.

We're particularly fond of silicone for dildos. It's smooth, non-porous, easy to clean and has enough flexibility to make it comfortable for intimate play.

For pegging, that combination of body safety, flexibility and cleanability makes silicone an excellent choice.

4. Lube, Lube & More Lube

The rectum doesn't self-lubricate, which means lube is essential for pegging and anal strap-on sex.

Apply a generous amount to the dildo and receiving partner before penetration, and keep the bottle within reach so you can add more whenever you need it.

If you're using one of our silicone dildos, we recommend a good water-based lubricant. It's compatible with silicone toys and easy to reapply throughout play.

And skip numbing products.

Being able to feel what's happening helps the receiving partner communicate when something feels great, when they want to slow down — or when they want to stop.

5. Let the Receiving Partner Set the Pace

Especially during first-time pegging, giving the receiving partner plenty of control over depth and pace can make the experience feel much more comfortable.

A receiver-on-top position is particularly useful because they can lower themselves onto the dildo at their own speed.

If you're using another position, guide the dildo into place with your hand rather than enthusiastically thrusting around and hoping for the best.

Once you're comfortably connected, start with small movements.

You can always build from there.

6. Get Your Dildo Angle Right

If you're using a curved dildo for pegging, pay attention to its orientation in the harness.

The aim is for the curve to follow the receiving partner's anatomy comfortably and, if they have a prostate, potentially provide more targeted stimulation towards the front of their body.

For face-to-face positions, a curved dildo will generally point upwards towards the receiver's front.

For penetration from behind, turn the dildo so its curve points downwards towards the receiver's front.

It sounds like a small detail, but getting the angle right can make a considerable difference to how the dildo feels.

7. Don't Forget Pleasure for the Wearer

Wearing a strap-on doesn't mean your only role is providing pleasure for somebody else.

Some wearers find that the base of the dildo or harness provides enjoyable pressure as they move. You can also add grinders, dildo bases, panty vibrators or other strap-on accessories to bring extra external stimulation into the experience.

A vibrating dildo is another option. Vibrations can travel through the dildo and its base, potentially adding sensation for both partners.

And, of course, hands remain free.

Use them.

What About Strapless Strap-Ons?

If straps aren't your thing, you might be curious about a strapless strap-on.

Rather than being attached to a harness, one end of the toy is worn internally while the other penetrates the receiving partner.

This can create wonderfully close body-to-body contact, but don't be fooled by the apparent simplicity. Using a strapless strap-on without additional support generally requires more pelvic control and experience than using a conventional harness.

Movements tend to work better when they're smaller and closer — think sensual grinding rather than enthusiastic long-range thrusting.

Some people use a strapless strap-on with a harness, giving them the internal sensation and close-body design while adding extra stability and control.

Experiment and find the set-up that works for your bodies.

8. Keep Communicating

Perhaps the most important piece of strap-on advice we can give you has nothing to do with equipment.

Talk to each other.

Ask what feels good. Say when you'd like something slower, deeper, shallower or different. Laugh if the dildo slips out. Change position if your knees are complaining. Stop if something hurts.

If power play or role reversal is part of the fantasy, discuss that beforehand too. Being the penetrating partner doesn't automatically make someone dominant, and receiving penetration doesn't automatically make somebody submissive.

You get to decide what the experience means to you.

Consent isn't something you establish once before you start. Keep it enthusiastic and ongoing throughout your play.

9. Clean & Care for Your Strap-On

Once the fun is over, separate your dildo from the harness so both can be cleaned properly.

Sh! silicone dildos can be washed thoroughly with warm water and a suitable sex toy cleaner, then rinsed and allowed to air dry.

Our leather harnesses need a little different TLC. Wipe them clean rather than soaking them and allow the leather to dry naturally before storing.

Make sure everything is completely dry before putting your strap-on away somewhere clean and fluff-free.

Look after a quality harness and dildo and they can accompany you on many years of adventures.

Strap-On Sex Doesn't Have a Rulebook

Perhaps that's the biggest difference between how we talked about strap-ons in 2005 and how we talk about them today.

Strap-on sex doesn't belong to one gender, one sexuality or one type of couple.

You can wear. Receive. Switch. Explore pegging. Enjoy vaginal penetration. Add vibration. Play with power. Keep things intimate and tender. Get the giggles when your dildo points in completely the wrong direction.

Your strap-on doesn't determine your role — you do.

More than twenty years after that Scarlet Magazine article, we're still helping people find harnesses and dildos that work for their bodies, answering first-time questions and encouraging people to explore pleasure on their own terms.

Some things really don't go out of fashion.

Ready to Explore?

Browse our Pegging Toys for harnesses, dildos, kits and pleasure-boosting extras, explore our Strap-Ons collection, or head to our Pegging Advice guides for more help getting started.

And if you're still not sure which harness or dildo is right for you, ask us. We've been helping people figure this stuff out for decades — including on TV.