You’re looking for the holy grail of strap-on sex: today, you want to learn how to cum from pegging p-spot play.
If you’re like most people who happen upon this article, you’re probably specifically looking for hands-free prostate orgasms. Luckily, whether you’re with a lover or with a professional eros escorts, the process is the same.
I will caution you, though: hands-free orgasms (for anyone, of any gender!) are difficult. There’s a reason that a lot of vulva-owning people don’t orgasm during intercourse alone; they require additional external stimulation to make orgasm happen! The same can be said for a lot of people looking to learn how to cum from pegging; you may simply require a bit of extra penile stimulation to make that orgasm happen.
That being said, there are some things you can do to increase your chances of having a prostate orgasm from strap-on sex.
If your strap-on wearer is on board (you did talk to them about this, right?), here are some of my best recommendations if you’re trying to learn how to cum from pegging p-spot play:
(Author’s Note: This article is specifically written for prostate-owning bottoms who are looking to receive strap-on sex from their partner. If that doesn’t describe you, please take whatever advice is helpful here and apply it to your own configurations!)
Enjoy Some Denial Ahead of Time
If you’re not into orgasm denial, this one is probably going to be a bit of a rough one, but it’s so much easier to have prostate orgasms when you aren’t fresh off an orgasm. Pent up arousal makes it easier to hit the p-spot and heightens sensations, making everything feel more sensitive and pleasurable.
You know this. There’s a reason that the most-recommended advice for lasting longer during sex is to orgasm regularly beforehand. Sensations feel less intense when you’ve recently had release.
We can use this advice to our advantage with prostate pleasure, too, though. By not having an orgasm, you’re making all of the bits more sensitive and easier to stimulate. You’re reducing that orgasmic threshold, making it easier to tip yourself over the edge with levels of stimulation that would not, necessarily, normally make you cum.
To do this, simply….don’t orgasm. That’s it.
I’d recommend at least a week, but 2-4 weeks is probably better if you’re really trying to make these how to cum from pegging tips most effective.
If you want to increase the effect here without the longer timespan, you can add in some edging sessions in those no-orgasm breaks. Simply masturbate to the edge of orgasm – but don’t actually orgasm. Do this as often as you’d like, ramping up your sex drive without ever actually letting it enjoy some relief.
Come into your pegging session with this ultra-sensitive state, making it more likely that the prostate play you do enjoy will tip you over the edge.
How to Cum from Pegging: Know Your Body
Can you verbalize where your prostate is? Do you know what angles hit it best? Do you know what toys or toy shapes tend to do best?
If not, you can’t really expect a pegging partner – who can’t what you feel or even the dildo they’re sliding inside of you – to magically create orgasms from thin air.
Having internal orgasms (g-spot or p-spot) requires knowing what those internal spots require for orgasm. This is doubly important when you’re asking someone else to hit all of those spots for you. This is triple-y important when you’re asking someone else to hit all of those spots and somehow do it with a toy they can’t see nor feel.
Knowing where your own prostate is (and how you need to pleasure it to get those p-spot orgasms) will allow you to communicate with your top during pegging to get the best chances of a prostate orgasm during pegging. Things like:
- “Can you please go a bit faster, Ma’am?”
- “Oh, a little deeper please!”
- “Get the dildo to go a little more towards my belly button if you can.”
Are absolute gold to your top.
Most tops want to see you deep in the throes of pleasure. This is a whole lot of physical exertion (with minimal physical benefit to the strap-on harness wearer), so you’re doing yourself a huge favor by having this info ahead of time. Not only does it give the top what they want to see, but it also makes it easier to give it to you, making it more likely they’ll want to do more pegging in the future.
If that info is still a mystery to you, consider playing with prostate toys and anal dildos until you figure out what configurations feel best for you.
How to Cum from Pegging: Get Creative with Positions
Just like your g-spot owning counterparts, you’re going to quickly realize that not all sex positions are created equal. Some positions will hit your prostate better than others.
READ: Best Pegging Sex Positions for Beginners
Think about where your prostate is and visualize how the dildo will travel in any given sex position. Will it be at the right angel?
In general:
- It’s easier to hit the prostate if the receiver’s knees are pulled up towards their shoulders in a Happy Baby-esque position.
- A posterior tilt of the hips (think of tilting your hips so that you’re trying to touch your penis to your head) makes it easier to hit the p-spot.
- Your sex position needs to be easy enough that your giving partner can maintain it and provide the sensations you need for long periods of time. If you find a level 100 sex position that hits your prostate perfectly, it won’t matter if your partner can only sustain it for 30 seconds.
The exact sex positions that are going to make it easy to learn how to cum from pegging are going to be very individual to you and your partner. In general, partner-on-top positions or missionary positions where the receiver is folded in half are going to provide p-spot pleasure for most people. Whether or not those are comfortable positions for you and your partner is very unique to the two of you though.
Especially if there’s a large height or weight difference between you and your partner, you might be more limited in “traditional” sex positions than you might be with vaginal sex. That doesn’t have to mean the end of your fun, though! Continue to experiment – and preferably check out some of my favorite pegging positions that I’ve found great for couples of discordant heights and sizes.
How to Cum from Pegging: Experiment with the Dildo
Strap-on sex has one very awesome benefit: the penis is interchangeable. When playing with a biological penis, the penis you have is, well, the penis you have. With pegging, that’s not the case. You can swap out dildos at any point.
Use that to your advantage!
Not all dildos are built the same. Some dildos may slide into your prostate with pinpoint accuracy and others may do nothing for your p-spot.
Dildos with a nice curve near the tip, when worn to point that curve towards your belly button, are going to be some of your best chances at hitting the prostate. How deep that curve needs to be is individual to your own body. Your prostate might be shallower or deeper.
Partner your dildo swapping with some of the other tips on this page for the most effective plan. If you know that Dildo A feels amazing when handheld when you’re laying in the fetal position, it might be a perfect fit for Spooning sex positions. If you know that Dildo B only feels great when you’re standing up and leaning over a table, it might be great for that standing sex position.
Take “Control” During Strap-On Sex
Yeah, yeah, I know that the appeal of pegging for a lot of bottoms is that they get to be the “receptive” partner and enjoy simply receiving sensations.
But, not to harp on the same subject, but your strap-on wearer has zero sensation in their strap-on dildo. They don’t know if it’s hitting your thigh, inside of your body, or hitting your prostate. They also don’t know what feels best inside of your bum like you do. You can make on-the-fly adjustments to help everything feel more explosive in a way that someone who isn’t you just can’t.
There’s a reason that Cowgirl/Partner on Top positions are the most-recommended positions for g-spot owners to have g-spot orgasms. Turns out, if you can simply wiggle and adjust your body on-the-fly during penetration, you’re more likely to have an orgasm from slamming into that innermost spot! You control the depth, speed, angle, tilt of your hips, and everything to make it all fall into place.
If you’re trying to learn how to cum from pegging, take some time during your next pegging session to be the person who does the movement. You can make this happen in most sex positions – even Missionary. Explore different angles, speeds, and depths to see what best hits your prostate in that position. Since you’re in control, you can swap things up in seconds.
Since most prostate orgasms only happen after building the same sensation, over and over and over, this lets you build that orgasm in a way that can be very hard to get if your strap-on harness wearer is controlling all of the action. If the dildo slips into the wrong angle on a thrust, you can do all of the course correction yourself and continue that ascent to orgasm.
Even better, if you’re in a femdom or power exchange relationship, you can frame this as an act of service. Something like “May I do the work for you, ma’am?” can be hot AF for your top while still keeping you both within the power exchange headspace you’re going for.
If you need other ways to frame it that help it fit into the submissive vibe you’re going for, here are some statements that might help:
- “Lay back and enjoy, ma’am, as I pleasure myself on you.”
- “Please let me use your cock to get off. I love feeling you inside of me!”
- “I’m so horny for you, Mistress.”
- “Let me show you my devotion through my body. I want to show you how much I appreciate you letting me have your cock!”
Train Your Body with Your Penis
You’ve been having orgasms from your penis for, what, 5, 10, 30 years?
And you just expect to stop touching your penis and the orgasms will still happen?
When you put it like that, it seems awfully unrealistic to assume that something slid up your butt will magically make the orgasms happen – and that’s true! Even if the sensations are out-of-this-world, your body has simply learned to take its orgasmic cues from touching your shaft. You may not even realize how ingrained it is.
You may need to “train” your body to accept your bum as an orgasm creator.
Luckily, the “training” for this is not exactly a hardship.
Next time you’re doing anything anal-related, pair the anal pleasure with strokes on your penis. Masturbate (or peg) like usual up until the point of orgasm.
Once you’re there, I want you to cease all penis stimulation, allowing the anal sensations to be what tumbles you over the edge.
This is going to feel like an “incomplete” orgasm (or ruined orgasms, for the kinky among you). P-spot orgasms do not feel like penile orgasms, and if your body is expecting a penile one, this might feel like a large let-down.
Don’t let that dissuade you. Orgasms are a renewable resource, and you can always have penile-only ones later.
Continue to do this practice. Each time you get closer to orgasm, try to cease penile stimulation a little bit earlier.
For example, the first time you do this, you might stop stroking your penis for two strokes before you have an orgasm. The next couple of times, you might try to stop stroking your penis for three strokes. On and on and on.
This helps retrain your body to recognize anal stimulation as a potential orgasmic trigger.
Down the line, you might find that you really love the anal sensations as they are, and you just pepper in a penile stroke or two, as desired, while trying to chase most of your orgasmic build-up from the anal play.
Finally, Give Up on the “Sex with Harness” Idea
The act of pegging can be hot AF. Feeling your partner’s bodyweight behind you as they push into you can feel absolutely amazing and ridiculously intimate. But it also is, literally, your partner pushing into you, over and over, with all of their body weight and subsequently getting very minimal physical stimulation for themselves.
All of this means that the best way to learn how to cum from pegging might be, y’know, to not be pegging.
Pegging is physically demanding, and the fact that human bodies are so large limits how fast and deep penetration can go. There’s a stopping point where your strap-on wearer will be unable to continue and/or unable to get the depth or speed you want. Your strap-on wearer may also be unable to tilt or angle the dildo where you want it to go without it falling out.
Those limitations are really nicely removed if you’re hand-holding a dildo. A single hand can move a lot faster than a whole body. As the dildo holder will now have eyesight on the dildo, they can also get much more creative with more extreme angles that can really target the prostate.
(You can reduce some of that physical exertion by using a thigh strap-on harness, but it doesn’t eliminate the other issues.)
If orgasm from pegging is high on your bucket list, I highly, highly recommend enjoying your pegging as you normally do – and then swapping over to having the strap-on wearer use their hands to use a dildo on you. Not only does this give them a break from all of the physical exertion, but it’s much, much, much more likely to result in prostate orgasms.
If you need another great reason: this helps teach the strap-on harness wearer what you like. As they see and control what angles you need with their own eyes, they’ll better be able to make on-the-fly decisions during strap-on sex to help hit those spots.
Update: July 2025, May 2025.
