Getting Started With Pegging

Pegging is a sexual act between a man and woman, in which the woman penetrates the man’s anus with a strap on dildo. The term pegging was coined and popularised by Dan Savage’s “Savage Love” advice column in 2001 - however there are references to pegging in the Marquis de Sade’s Philosophy of The Bedroom, which was published in 1795.

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Pegging Equipment

Whenever folks start out on their first pegging adventure, there’s always a question - how much should I spend on this stuff, which we might end up not liking and will then spend the next 5 years sitting in the back of the closet before finally being chucked out?

It’s a big question and obviously you should spend within your means, however, you and your partners enjoyment of pegging will be strongly influenced by the hardware you’re using. Cheap dildos are usually toxic and porous. Cheap harnesses are typically low quality, uncomfortable and can be rather ugly.

By investing in gear that feels good and looks great, you are much, much more likely to start out in a positive direction. Further, if it doesn’t pan out for you and you have used good quality, body safe, you can sell or trade them.

/r/StraightPegging has a great wiki for quality pegging equipment and /r/sextoys also has lots of really helpful information on how to buy and care for good quality sex toys. Buy or sell your body safe sex toys at /r/usedsextoys

Dildos

There are so many out there it can feel a bit bewildering when you’re starting out. If this is your first try at pegging, a smooth, medium to soft, modestly sized toy (less than 1-1/2” diameter and less than 7” in insertable length) is a good start.

Some reputable manufacturers:

Some occasionally controversial manufacturers:

Fun Factory some of their toys are not 100% body safe and may contain ABS plastics, which can be slightly porous.
Doc Johnson - platinum premium line not all of Doc Johnsons toys are body safe, so please check the materials before purchasing.

Harnesses

The right harness can make or break the pegging experience for the giver, so it’s important that you choose something that looks and feels sexy, is properly designed and well constructed. There are two main types of strap on harness; panty style harnesses which are designed to look like underwear and the more traditional strap style harnesses. Panty style harnesses are very pretty, however they are more likely to have a flexible fit and are restricted by the maximum o-ring size. Strap style harnesses are the most secure and I personally find them easier to use, although they can sometimes feel unfeminine.

A good strap on harness will fit securely, comfortably, and also be designed and constructed to take the weight of the dildo without the giver having to hold it.

Lower cost, but still pretty good:

Nastoys Revolt and Revolution
Sportsheets

Higher cost, but better value:

Spare Parts - Particularly the Joque.
RodeoH
Aslan Leather - vegan options are also available
Tantus Black Widow and Nevada

Another great place to look for strap on harnesses is Etsy!

Strapless Strapons

Strapless Strapons are double ended sex toys in which one end is inserted into the giver’s vagina, thus negating the need for a harness. The benefit of them is that (in theory) they don’t need a harness and so there is more opportunity for skin to skin contact during pegging, and they can also physically stimulate the giver.

Sounds awesome, I know, but a lot of pegging couples - including folks who have been doing it for years - struggle with them. When vaginas get excited they relax and self lubricate, which can make it hard to keep a silicone bulb in place, so you end up either using your hands to steady it which is really distracting or using a harness. Having a lump of silicon wiggling around in your vagina can feel good if it’s wiggling in the right places, but usually it just feels like a lump of something in your vagina. The size and the shape of the bulb does vary a lot and some women find them distractingly uncomfortable or just painful. Also, because they tend not to be particularly secure, they’re hard to fuck with in certain positions, which can be really limiting.

Overall, I personally would not recommend using a strapless strap on as a starter toy. If you’re more experienced and looking to try something different, then by all means give a few a try.

Best of the bunch

Shopping tips

So, as we’ve discussed, some of this stuff can be super expensive. Used, body safe, sex toys are an option as you can sterilise them before you use them. Tantus sell grab bags of some of their toys, in which you cannot choose the colour or texture of the toy, but in return you get a significant mark down of the cost. Bad Dragon always have toys on clearance and also “Drop” larger selections of toys that are reduced cost periodically.

Many, many sex toy reviewer blogs also have discount or coupon codes with retailers, so when considering a sex toy and checking through the reviews, check to see if they also have an offer code. Retailers will also routinely have sales, so it’s good to check through your favourite stores to see what’s on offer.

How do I get started with Pegging?

The first thing that I would recommend is that you listen to this podcast which is hugely informative and specifically aimed at women who are starting out and this one which is made up of the stories of women who peg - it’s by a lady called Ruby Ryder. Ruby runs two blogs, Pegging101 which is full of technical information and help and Pegging Paradise where you can find more of her podcasts and the kinkier side of things. They are excellent resources from a knowledgeable, welcoming and passionate woman. I recommend them wholeheartedly.

Don’t worry too much about the porn. Pornography is to sex as Disney is to relationships. Authentic, real life experiences are much hotter and you can choose better background music.

Next, the key to good butt stuff is to start small and go slow. I cannot stress this enough. If this is your partner’s first foray into butt stuff, you are not going to be able to pound them into the mattress with a 9” rubber cock on the first attempt. Indeed, if this is your partner’s first foray into butt stuff, I wouldn’t recommend that you use anything more than your fingers.

Fingers is a good start for the following reasons: you will be able to feel your partners response to what you’re doing much more keenly, fingers are small, you will be able to feel inside your partners rectum, including their prostate - it will help you to develop a sense of their anatomy, you don’t have to order your fingers off the internet.

Starting Out

It’s smart to get them to clean their butt with a small enema bulb first. Pop them in the shower. Make sure they are clean, fresh and comfortable. Meanwhile clip and file your nails, get some nitrile gloves handy, a towel, some body lotion, some lube and set yourself up somewhere where you guys can be comfortable - like a bed.

Maneuver your partner to the bed, have them lay down on their belly and give them a butt massage with your body lotion. Massage their cheeks, the tops of their legs and the inside of their thighs. Next have them get on their hands and knees and spend a good long while rimming them. Be gentle, you do not need to force your tongue into their butthole, hold onto their hips, touch their thighs, run your hands over their butt - the object of the exercise here is to tease. If you’re concerned about something smelling or tasting swampy - please trust me that as long as they’ve prepped and showered, it will not. Butt tastes like regular skin. They’re ready for some penetration when their asshole is clenching and relaxing and they’re making some sounds.

Put on your glove and lube up. I prefer to wear two gloves as this makes my fingers smoother. Use plenty of lube, mostly on the tip of your finger (it’ll work it’s way down), be sure to also make sure there’s some on your knuckles as you want their butt cheeks a bit lubed too - this will reduce drag and be easier for your both.

Slowly insert your finger into their anus, with your palm facing downwards. Stroke with your finger, starting out gently and slowly increase pressure. Check in with them regularly, make sure they’re okay, ask them what feels good - more/less pressure, faster/slower, deeper/shallower, more/less fingers, etc - reapply lube frequently, explore, keep talking and have some fun.

They may not be able to cum from prostate stimulation alone on the first, tenth or hundredth try at this. Don’t worry about that, they’ll be having lots of fun. Once you’re comfortable and you’ve figured out their butt, flip them onto their back and blow them while you’re massaging their prostate. They probably will be able to orgasm from that. When they do start to orgasm (you’ll feel it with your fingers first), keep their cock in your mouth but focus your efforts on their prostate - so they can get a feel for what a butt driven orgasm feels like.

Moving on

Maintain your warm up routine of his enema prep, butt massage and rimming. Start introducing butt plugs. You can get butt plug starter kits which contain 3-4 sizes of plug.

Again, start small and work your way up in size slowly. Don’t use metal plugs when you’re starting out. Experiment with the materials they’re made of, some butts like silicon, some like PVC, some like rubber (please read up on the safety of sex toys and use a condom on them if you’re using a toy that may be toxic or porous). Make sure that your plugs have a good sized flared base, to stop them disappearing into your bottoms rectum.

While they’re wearing their butt plugs, have regular PIV sex, do some oral - get them used to the feeling of having something in his butt.

Pegging

After a few weeks of all that they’ll be pretty much begging you to fuck them. Hooray!! Start with a dildo that is approximately 1” to 1 1/2” in diameter and around 6”in insertable length. During your butt plug experiments you should have figured out which toy materials they work best with, stick with what works. Select your harness and toy and strap up while he’s not around. Get used to the feel and weight of it. Have a dance around in it. Get used to moving with it.

Cheaper harnesses with polyester straps can be uncomfortable, so wear panties underneath. I’ll be honest, there are a lot of ugly and unfeminine harnesses out there - choose something that looks good and makes you feel good when you’re wearing it.

Start out with your prep, pop in their favourite buttplug, give them a massage while it settles and then, when you’re ready and he is put them on their hands and knees, take out the plug and insert your dildo.

Hold on to their hips for support and fuck them slowly.
Work the dildo into their body slowly, start with the tip, then work deeper.
Reapply your lube regularly. Use more lube than you think you need.
It may take a bit of figuring out to get your position right in terms of height. Adjust and experiment. You may find it easier to have them on their belly with a pillow tucked under their hips.
Roll your hips to fuck them, rather than using a straight in/out motion. If you can deadlift, use that motion.
Embrace your awkwardness and have fun. Getting used to fucking is going to include a few mishaps; own them. You might lose your balance. Your cock might accidentally slip out. Your harness might come loose. It’s all good, we’ve all been there.

Lube

All butts are different and so finding a lube that works for the butt in question can be a bit of a process. Shop around and experiment. Lubes can be oil, water or silicone based - be advised that silicon based lubes can damage silicone toys. Under absolutely no circumstance whatsoever should you use a lube that contains a numbing agent like lidocaine. I personally prefer water based anal lubes with no scents, flavors or added nonsense - as this reduces the risk of irritation and is easy to clean, but what works for one butt won’t work for them all, so purchase your lube in small quantities and find what works for you.

More great resources on the basics of anal sex

Citations

Original: Getting Started With Pegging. (2023, September 23). In [r/FemdomCommunity/wiki]. https://www.reddit.com/r/FemdomCommunity/wiki/index/zkinkguides/pegging/