When we started to write our guide to pegging and chastity we knew that describing the best beginner and advanced pegging positions wouldn't be enough. We wanted to show you what they look like.
Position can have a huge impact on the pleasure of you and your partner during journeys to bone town. (BONE?!) Just because a certain position works well during vaginal penetration, it doesn’t necessarily mean that it will work for anal penetration, too. There are some variables at play, such as potential height differences between partners, experience levels and the size of the strap-on dildo. Some positions will allow for relatively shallow penetration, while others will let you go nice and deep.
Sorry to break it to you, but we didn't set up our camera, light some candles and I didn't get balls deep into slave D - sadly. Not on this occasion anyway.
Instead we got in touch with our favourite illustrator Soushiyo, who also drew our chastity measurement comic, to create the wonderful pictures you'll find within this post. Ambassador, you are spoiling us, I hear you say. No thanks needed, my pegging pals. My pleasure.
So without further ado, here is our illustrated guide to help you enjoy what we would consider to be our favourite sex positions for pegging. I'm going to add a caveat to this and say currently, because until we've tried them all how will we truly know what the best ones are?! For science, we'll keep experimenting and report back if we find some new ones to add to this list. You're welcome.
Positions for Beginners
Your level of experience (both the giver and receiver) will play a determining factor in what positions work best for you. If you’re still relatively new to pegging or have never tried it before, you’ll want to choose a position that allows the receiving partner to have as much control as possible. It’s also a good idea to start off with positions where you can see each other’s faces as much as possible - that way you can see each other’s reactions (very hot) but also peggers can work out how the peggee is feeling.
Here are some good options:
1. Spooning
Oh, this one is a classic! Both partners lie on their sides, facing the same way. The receiving partner might have to bring their top leg or both legs forward in order to let the giver enter them. This is a great position because it offers full body contact and feels more intimate. Perfect for some slow and sensual love making and also for the giver to watch the receiver’s face for feedback as to what feels good.
Using a longer dildo in this position will give the pegger more freedom with depth. There's nothing more frustrating for a receiver to beg for more and that not be an option due to the dildo being too short. Alternatively keep another option close to hand next to you on your bed so that you can increase the size during a short intermission.
2. Reverse cowgirl/cowboy/cowpoke
Yee-haw folks! This is a great position for pegging because the receiving partner can control the speed and the depth of penetration. However, this position requires good stamina from the peggee, as it can be tiring to ride a strap on for a long period of time. Plenty of Weetabix before jumping into this one, I think.
As tempting as it can be for the person doing the pegging to thrust their hips from the bottom here, resist, at least initially. Let the person on top get into a comfortable rhythm before you get involved. A mistimed thrust can be very painful if you go too far or too deep too quickly. Patience is key.
3. Lifted missionary
This is your typical missionary, just with a pillow under the receiving partner’s hips for easier entry. Eye contact here is an added bonus, increasing the intimacy while also letting you monitor your partner for any non-verbal cues.
Instead of a cushion you could use a stack of towels as they offer a more stable, firmer platform. Plus you might want to avoid covering your pillows in lube, poop and/or cum!
Positions for Experts
If the previously mentioned positions don’t excite you as much, and you’re an experienced pegger or peggee, here are some sex position ideas just for you:
1. Doggy style
Why didn’t I include this in the beginners list? There are two main reasons.
First, the lack of eye contact doesn’t let you check in on your partner’s non-verbal cues.
Second, this is a position that lets you penetrate quite deeply, which not all beginners might be comfortable with. Put a body harness on the peggee for additional grip and thrust! Also, the golden rule with this one - shoulders down, ass up. Thank us later.
Putting silk or latex sheets on your bed before sex might look sexy and add to the mood, but you're going to slip all over the place. In this position that could be dangerous as you'll easily lose control. A little friction between your knees and the bed will help here. I'm not saying you have to buy a pair of knee pads, but you know, it's not the worst suggestion.
For some added spice (and dominance), the receiver's wrists can be restrained. A leg spreader bar can work with their ankles but we’ve found it does tend to get in the way for this position. A safe and secure rope tie for each angle will do the trick instead or use the leg spreader at the thighs, just above the knees, so it keeps the legs open but doesn’t get in the way.
2. The butterfly
In this position, the receiving partner is lying down on their back at the edge of the bed and the pegger is standing up. The peggee will typically have their legs on their partner’s shoulders. Wrap your hands around the peggee’s thighs and thrust with your gluteus maximus (your bum!)
We have the liberator sex wedge cushion in two different sizes for positions exactly like this one. The foam core is firmer than a pillow, which gives both of us more options. I like to put the higher end on the edge of our bed and make slave D lie on his back so that his caged cock is very accessible to me. Having his hips up high also makes it very easy for me to remove his chastity cage, tease him as I fuck him then angle his cock so that he cums all over himself at the point of climax.
(Don't forget to make sure that they clean up every drop before you pull out!)
Similarly to the doggy style position, you can easily introduce bondage here. Cuffs or rope can be used to restrain the wrists behind the head. If you want to get more advanced, strap them into an arm binder before they lie on their back. It's not nearly as comfortable for the receiver, but it's a sure fire way to completely eliminate any chance of them using their hands. At that point I lose total control, a place we're both very happy with.
3. Full throttle
In this position, the peggee lies on their back and brings their legs up to the shoulders of the pegger. The pegger then uses their hands to balance above the peggee.
D isn't as big a fan of this position as I am for selfish reasons. His comments: "My chastity cage is usually pushed into me when she thrusts forwards, which can make it dig into my skin. Depending on what device you're wearing at the time it can get pretty uncomfortable. Also, there's less access for her to play with the cage - a little teasing mid-fuck is fun, but this position restricts that."
You'll want to consider the platform (a bed, bench, sofa, etc.) that the receiver is going to be on, more specifically the height. If you look at the picture above you can see that the height of the peggee, or more specifically the height that their dildo will penetrate the receiver, will significantly impact the depth that you can achieve.
If you're going to peg on a bed the pegger might need a little helping hand in the height department. A pair of heels could elevate their position, but it could make them less stable on their feet. We'd recommend a chunky heel that will provide more stability, or find a different place lower down to have sex!
No matter which position you try, don't forget to have fun, clean your toys thoroughly before and after pegging, and communicate clearly and honestly.
If either of you start to feel any pain, stop immediately and assess the issue. Extra lube for the receiver or a little extra padding behind your harness for the giver can really help.
Beyond that, it's time to strap-on your cock (and a hydration backpack if you plan on going at it for a good while, no-one wants to cut your session short because of cramp- stay hydrated folks!) and get adventurous!
And if we haven’t included your favourite positions, why not @ us on social media or drop us a message to let us know your favourites and why.
And if these positions aren't enough to get your imagination going, read on to the next part in our guide: Our favorite pegging-compatible kinks!
ABOUT THE AUTHOR
Mistress K
Mistress K (she/her) is a queer kinky woman and in a long-term chastity-led relationship with Slave D, the other half of the dynamic duo who run House of Denial.
Thoughtfully dedicated to consent-led BDSM practices and interactions, Mistress K supports our community via our customer service channels (does that make her a service top domme?) by engaging with anyone interested, enthusiastic or curious about chastity.
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