A beginners guide to pegging

It’s a girl with a strap-on and a guy who wants some. But is it domination? And just how do you go about organising such an addition to your love life? Kasumi Archer investigates.

Photography Richard Scholes
Models Angel B Trayer and FZ

Woman and man about to engage in pegging, photograph by Richard ScholesIn 2001 Dan Savage, irreverent sex and relationships advice columnist from Seattle’s The Stranger, ran a competition to name the sexual practice where a woman anally penetrates a man with a strap-on dildo. Other front-runners included bobbing and punting, but it was pegging that crossed the line first in the end. As it were.

Naming gives legitimacy, and perhaps because of this, hetero strap-on sex is becoming more widely talked about, if not more widely practised. Pegging features in a storyline of the television series Weeds and the lyrics of the Peaches song Back it up, boys.

There is no right or wrong way to have sex, and no step-by-step guide will get you where you want to go all the time. It’s always about figuring out what’s right for both of you at the time.

Three common questions

Is pegging about female dominance?

Pegging is as much about domination and submission as any sex is — it depends on what you both want. There are ways to peg where the woman is in control, where the man is in control and where control is shared equally. For example, when the man is on top, he can control the speed and angle of penetration.

Why would a man want to be pegged?

Pure physical sensation is a common reason. Pegging is an excellent way to stimulate the prostate gland, which can be hard to reach with fingers alone. Other men are specifically looking to be dominated, and still others just want to try something new and different. Pegging can also be a compelling exercise of trust and intimacy that couples find communicates more than words.

If a guy wants to be pegged, doesn’t that mean he’s gay?

Being gay means wanting to have an emotional or physical relationship with another man. It has nothing to do with having something up your bottom.
Woman and man about to engage in pegging, photograph by Richard Scholes

Enough of that. Let’s get started.

1. Raise the issue

You’re getting off lightly if he raised it first, and you replied coyly, ‘How about tonight?’ If it’s been kicking around in your head for a while and you don’t quite know how to knock on his back door, there are several great ways to drop the hint without pressuring him.

Appeal to physical pleasure

‘His P-spot is the male equivalent of the G-spot, and by ignoring it, he’s seriously missing out. When stimulated it can lead to really intense orgasms. To find his P-spot, have him lie on his back and insert a well-lubed finger, palm up, almost all the way in, curve the finger in a ‘come hither’ gesture and massage firmly.’
Em & Lo

Talk equality

‘You know how you mentioned fancying anal sex? You’re up for receiving, too, right?’

Tit-for-tat sex rather defeats the purpose of sex, but there is never any harm in pointing out that there’s a very reasonable equivalent of any other stuff that might be going down.

Little white lies

‘I had a dream that I was pegging you — isn’t that crazy? It was kinda hot though.’

I have heard of a woman who produced this line in an instant messaging conversation, to which her boyfriend replied, ‘That would be nice.’ Assuming that he knew what pegging was, or at least had consulted Wikipedia, they discussed this future activity, including her indicating that she’d acquire the necessary kit. It then became evident that he’d assumed pegging was some newfangled word for regular sex. He decided to give it a go all the same, and apparently they both had a nice time.

2. Start simple

Man and woman about to engage in pegging, photography by Richard Scholes

There’s no need to jump right into the strap-on action. Get some water-based lube and a few pairs of rubber gloves, and try a bit of manual prostate stimulation alongside, for example, oral sex or a handjob.

Buying rubber gloves is a science in itself, as most pharmacies only stock ‘one size’, which many women find their hands swim in. If you ask the pharmacist if they stock a smaller size, you invariably get asked just what you want these rubber gloves for. Points for sharing. Several online retailers sell hundred packs in any size if you want to avoid the unnecessary enquiry.

Some people like to try butt plugs or anal beads at this point too, which is entirely according to taste.

3. Acquire your kit

Man and woman engaging in pegging, photography by Richard ScholesIf you then both want to move on to something more exotic, you’ll need to acquire your strap-on. Strap-ons involve two parts: harness and dildo.

Good sex shops should let you try on harnesses, and you should expect to pay £30—£50. Make sure that the harness feels comfortable, sturdy and allows the dildo to point in a direction that’s likely to be useful — cheaper harnesses may point your dildo downward, which makes it harder to control. Some harnesses have a pouch inside to add a vibrating object for extra sensation for you.

Dildos, sometimes called dongs, fall into a similar price range. For first-time pegging choose a smooth-surfaced, modestly-sized number. In the words of one man,

‘The anus is the body’s magnifying glass: everything that goes into it appears to be twice its natural size.’

Silicone is popular for dildos because it is easy to clean, hard to damage and it’s very unlikely that someone will be allergic to it. However, silicone dildos tend to be significantly more expensive. Rubber dongs can be acquired for around £20.

Once again, make sure you’ve got enough water-based lube. You might also find that condoms and anti-bacterial wipes make clean-up easier.

4. Assume the position

Man enjoys being pegged, photograph by Richard ScholesIt can be fun to put your harness on before you get right into the pegging. This makes for a nice promise of something more intense to come as you start with lubing up and the now-familiar anal play.

Many couples find that male-on-top is the best position to start with, as having no sensation in the operative part makes controlling placement more difficult for the woman.

If you do want to go for something where you have complete control, a doggy-style position might be better. Bending him over the side of the bed from kneeling can be good if you’re worried about knocking him over with your enthusiasm.

Make sure the dildo and his arsehole are well lubed, and place the head squarely against his pucker, apply gentle pressure or let him press back against the dildo at his own speed. Once the dildo enters into him about an inch or so, pause and let him get used to the feeling.

From anal play you will have hopefully got a feeling for what kind of sensations your man likes, and should be able to peg in a way that is consistent with that. For example, some people strongly prefer the pushing in over the pulling out sensation, in which case you can just thrust forward continually, rather than pulling out and then pushing in. A ‘reach around’ may be helpful too:

reach around. n. The act of masturbating a sexual partner, usually while simultaneously performing another sexual act from behind, such as doggy-style or anal sex, or spooning.

As with any sexual activity, the key is to communicate continually about what is and isn’t working, as well as paying attention to his reactions, movements and the sounds he makes. Talk, talk and talk some more.

Further information
www.take-it-like-a-man.com
Approaches strap-on sex as if it were an act of domination, but contains useful ‘how to’ advice
Bend over boyfriend
Instructional DVD featuring sex educators Carole Queen and Robert Morgan, US$34.95
bendoverboyfriend.tumblr.com
Inspiring tumblelog of pegging and women wearing strap-ons.

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