How to Give Yourself a Life-Changing Orgasm With Prostate Milking

Get really turned on. Use a delicate touch. Try a “come-hither” motion or the “windshield wiper” technique.

Sep 9 2021, 4:44pm
Advice on the finer points of having great sex.

For people who have them, penises are most often considered the stars of the show when it comes to sexual pleasure. More often overlooked is a small organ that can be accessed through the rectum to set off full-body, euphoric multiple orgasms. I’m talking about the prostate.

Not much academic or clinical research has been done on the pleasure potential of the prostate, let alone how to give yourself a prostate orgasm if you’ve never done it before. That’s OK—we’re here to help you take your prostate quite literally into your own hands! Let’s break down how to blow your own mind from behind with the help of sex educators, adult performers, therapists, and other prostate pleasure pros.

What is the prostate, exactly?

The prostate is a ping-pong ball–sized gland that lives below the bladder, close to the inner root or bulb of the penis. In its other functional roles, the prostate helps maintain erections and transports sperm during ejaculation, among other important reproductive tasks. 

“While scientific types might like to debate and get super bogged down with glands and homologues and the like, a rough analogy would be that a prostate is similar to a G-spot and pretty much located in a very similar manner,” said Rain DeGrey, a sex educator and adult performer who’s been teaching classes on the ins and outs of P-spot orgasms for 13 years.

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Like the genitals and the perineum (which is the skin between the balls and butthole), the prostate has thousands of nerve endings, which, when stimulated, can feel intensely pleasurable—though not for everyone. As with any sexual act, your personal mileage may vary. “I think it's important to let prostate owners know [that] not everyone likes to have their prostate massaged,” said sex educator Reid Mihalko, though he encourages prostate exploration nonetheless, because, he said, “Figuring out what you don't like is also a win.” 

OK, so… is prostate stuff actually just anal?

Though prostate stimulation and anal sex can both involve anal penetration, the two sex acts are totally different. Internal prostate stimulation takes a softer touch and involves more precise movements and smaller implements, such as fingers or small toys, rather than dildos or penises. Because a penis or dildo doesn’t have as much range of motion as smaller toys or fingers do, it’s difficult to effectively massage the prostate with them.

What might not feel as different between the two is the stigma some people feel about sexual pleasure that involves their butts. “Many prostate owners feel self-conscious and/or shame about exploring prostate play,” said Todd Baratz, a sex therapist and sexual wellness expert at Arcwave. “Many men [in particular] internalize the idea that it's feminine (and therefore negative) to play a receptive penetrative role since they grew up learning that the receptive partner is female and therefore feel shame when assuming a receptive position.” While undoing these stigmas and unhelpful beliefs can be a real challenge to prostate rookies, Barartz offered this advice: "Try to remember that you’re plugging into outdated gender and sexual scripts that preclude your pleasure. They are also incongruent with your desires, if P-spot pleasure is what you seek.”

How is a prostate orgasm different from a penile-induced one?

A P-spot orgasm involves massaging—or “milking,” as it’s sometimes called—the prostate gland through the rectal wall with your finger or a sex toy. (The “milk” refers to the thin, whitish prostatic fluid that’s released when the prostate is stimulated.) 

For beginners, the easiest way to access the P-spot is with a lubed-up finger or toy in the butt. In some cases, though it’s rarer, some prostate owners can come by stimulating the prostate externally through perineum massage. 

What does a prostate-induced orgasm even feel like?

“On a scale from one to 100, I’d give a penile orgasm a 10 and a prostate orgasm a 100,” said Dainis Graveris, a certified sex educator and relationship expert at SexualAlpha. Why such high praise? “Penile orgasms originate in the genitals, but prostate orgasms feel like they’re coming deep within the body. Once it hits you, it’s a totally overwhelming and beyond-this-world experience,” he said.

Prostate orgasms also may last longer, be more intense or felt throughout the whole body, and can lead to multiple orgasms in a short span of time—Gravaris and other prostate enthusiasts called it the Super O. “The sensations are that intense. Blissful. Otherworldly. With no refractory period. That means that you can experience multiple orgasms,” he said. 

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Others described the experience as entirely different from a solely penile-induced orgasm. “When I get prostate-massaged, I ejaculate quickly,” Mihalko said. “There's not a big buildup, and I’m usually not erect, so it can feel anticlimactic. But what is really wonderful about it is, I know that I can still be having sex when I'm 90. Like, if I can't get it up, then I know I can orgasm this way.”

Why are some prostate orgasms more powerful than the ones I have with my penis?

It’s hard to say for sure! To date, no credible, peer-reviewed studies have been done on this specific matter. “Most of the information about this pleasurable function comes from anecdotal sources,” as R.J. Levin wrote in a 2017 paper in Clinical Anatomy. That said, there is a lot of that anecdotal evidence floating around. Websites, blogs, and community forums abound on prostate orgasms and techniques, from subreddits with 47,000 members to mainstream magazine articles to virtual and IRL groups of enthusiasts. One of the most prominent communities is supported by the sex toy manufacturer Aneros, which makes prostate-stimulating toys and hosts a private chat, wiki, blog, and forum where its 50,000 members share their experiences, advice, and insights on prostate pleasure. 

The fact that the area is packed with nerve endings, (along with the perineum and anus) likely plays a big role in why it feels great to touch it. So does the prostate’s location near the root of the penis, which is similarly sensitive—and doesn’t receive much stimulation, compared to the external shaft. Levin concluded that “the heightened body awareness” associated with prostate stimulation increases genital awareness and leads to that much more pleasure. Meaning, the more you’re in tune with your body, paying attention to every sensation (not just the genitals), the more intensely such sensations are bound to feel everywhere. Building increased awareness includes “retraining the brain” to receive new routes to pleasure. Gravaris echoed this sentiment as well. “It takes time to rewire the brain,” he said. “You’ll feel vulnerable. Being penetrated is a totally different mindset.”

How do I get turned on and ready for prostate milking?

In his report, Levin, citing the Aneros community, noted that many of the discussion topics surrounding how to have P-spot orgasms stressed relaxation, time, and practice. “Relaxing is huge,” DeGrey said. “If you can't relax, you're never going to be able to enjoy the experience. And letting something inside you is a very intimate and vulnerable act. Even if it's your own finger.”

Exploration can tell you a little more about whether prostate pleasure is up your street to begin with. “It can be extremely difficult to actually have a P-spot orgasm, and some people simply cannot. That doesn’t mean it’s not worth a try, but it is important to have realistic expectations, especially for people who are beginners in prostate play," said Baratz.

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As with any kind of sex, it helps to keep the goal firmly on pleasure, rather than results (aka, orgasm). “I encourage people to explore P-spot pleasure before seeking a P-spot orgasm,” said Baratz. This exploration can involve playing with the prostate during other sexual activities you already enjoy, like masturbation, handjobs, or oral sex. It can involve trying out different sensations, movements, and toys (more on that below) with the purpose of seeing how it feels, not necessarily getting off. 

As Baratz also reminded people: “Be prepared for poop—sometimes, yes, shit does happen!” If cleanliness is important to you, then make sure the area is clean before you start. This can involve anal douching, enemas, or merely ensuring that you’ve had a bowel movement a few hours before playing. If it doesn’t matter so much to you, then don’t worry about it. Many of the people who enjoy anal play understand that a little messiness comes with the territory. 

It’s also important to be turned on before searching for the prostate—or for any kind of penetrative play for that matter. When you’re aroused, the whole genital area (inside and out) becomes more sensitive and engorged, and hence different kinds of sensations are more likely to be pleasurable, and not like you’re being prodded. 

Mihalko called an anal penetration–ready orifice the “hungry hole.” Many prostate owners might not be familiar with the cues associated with such readiness, as they might not have experienced anal penetration outside of a prostate exam, “which is not erotic at all,” Mihalko said. “If you’re trying prostate play for the first time, make sure your body is aroused enough to want something inside it.”

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This can entail, as mentioned above, that the area is engorged and has a heightened sensitivity, verbal cues (if you’re with a partner), and a relaxed body free of tension, stress, or clenching. If you’ve never paid much attention to your body’s cues before, this might take some practice, but once you start making it a point to notice signs that you’re turned on, it’ll also become easier to decipher when a body is sending you do-not-enter signals.

How do I find my prostate?

Once you’re warmed up and ready for penetration, either lie on your back with a pillow under your hips (if your finger or toy is entering from the front), try a prone position on your stomach with one leg bent with the knee to the side to give your crotch some room away from the mattress so you can reach it. Or get on all fours (if entering from behind). If you’re using your fingers, DeGrey advised that you start slow and gentle, with a single well-lubed finger inserted into the rectum, with “no hangnails or cuts!” and “gloves, for the most safety.” Gloves help prevent any accidental cuts or tears to the delicate rectal lining. Plus, they prevent you from touching any poop you might encounter.

How do you know you’ve found the prostate? DeGrey advised pleasure seekers to feel for a “rounded lump, which may be more or less obvious depending on a person's body” and how turned on they are. But more than that, she said, “The biggest tell is pleasure. When it feels good, you found it.”

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Once inside, press your lubed finger or toy toward the belly button in a “come-hither" motion or “the gentle pressure of a circular or back and forth motion using a finger pad, not a fingertip,” said DeGrey. You’ll definitely want to start soft and increase pressure, as needed. 

In addition, Mihalko suggested the “windshield wiper” (a back-and-forth motion), and the “press-and-release” as other sensations to play around with.

You’ll want to experiment with different levels of pressure and intensity, but don’t do anything that hurts. “If you massage the prostate too hard, you can actually damage those nerves,” DeGrey warned, “which can lead to pain and even erectile dysfunction.”

Some people can come from prostate stimulation alone, while others like penile sensation along with it. If you’d like to try prostate and penile play together, once you’ve found the sensation and pressure your prostate likes, maintain that pressure, rhythm, or intensity, or, with your other hand, you can stimulate the genitals, nipples, or other erogenous zones to help things along. Continue to stroke your penis (or erogenous zone of choice) until the intensity builds and you feel pleasure radiating throughout, and not just in your genitals. Once you’re almost at the point of coming, stop touching your genitals and focus entirely on your prostate until you orgasm.

Can I use sex toys on my prostate?

Hell yes you can! Mihalko and Gravaris both recommended prostate-stimulating sex toys—with lube, always lube, and lots of it! Toys are especially useful if you have mobility issues or it’s difficult to reach your prostate with your fingers.

If you’re using a toy for penetration, make sure to choose one for anal play (meaning, one that has a flared base), because if it doesn’t, it might slip all the way inside, and that’s an emergency room visit you probably don’t want to have.

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Beginners should look for prostate toys that have smaller heads for easier insertion, especially if you’re new to penetration; tapered bodies that aren’t too wide or long, since the prostate is not that far inside the body; and, again, flared bases, so your toy won’t get lost up there.

While sex toys can be costly, it’s an investment in your body and your pleasure. “Professional tools create professional results,” as Mihalko put it. Popular beginner toys recommended by the experts VICE spoke to for this article include the Aneros Helix Syn Trident, We-Vibe’s Vector, and the njoy Pure Wand, which works on both G-spots and P-spots.

Holy shit, this feels amazing. Now… how can I get a partner involved?

Trying prostate play with a partner can be a vulnerable, intimate bonding experience. (It can also just be hot as fuck.) Plus, a partner can often go deeper, explore different angles, and try out positions that might not be possible during solo prostate action. 

You can try any positions or motions that work for masturbation with a partner, though if you’re just starting out, it’s best to start simply. “I have personally always found that having someone lie on their back and me sliding a finger inside while pressing up towards the root of the penis is the most effective way,” DeGrey said. “Toys are going to complicate things more in the beginning. People can certainly upgrade to toys, but for your first time out, stick with fingers. They're cheaper, and you already have 10 of them.”

If you’re the person giving the massage (or even if you’re the receiver), it’s important to pay attention to body cues. Obviously enthusiastic vocalizations and words are helpful in expressing likes and dislikes, but if someone is less vocal, look to other nonverbal signs. “Are their eyes closed or open? Is their breathing fast or slow? Are their muscles tense or relaxed? Are they pushing into you or are they pulling away from you? All of that is communication. All of that is feedback,” DeGrey advised.


Learning to give yourself a prostate orgasm if you’ve never done so involves a certain amount of practice, exploration, and open-mindedness. Remember that the reward is in the trying. Celebrate any progress you make, new sensations you’ve embarked upon, and any and all orgasms you experience. At the end of the day, knowing more about your prostate and your body in general—its likes, dislikes, cues, and responses—is all cause for celebration in our lifelong sexual education. And it’s an added bonus if now you know another potential way to make yourself—or perhaps even someone else—feel really, really good inside.

Follow Anna Pulley on Substack.

Tagged:

MASTURBATION, anal sex, prostate massage, prostate, prostate orgasm, Best You've Ever Had, prostate milking, prostate massagers

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