Prostate Milking Guide [2024] How to Massage Your Prostate Using a Sex Toy

By: Ian

Prostate milking is the Holy Grail of male sexuality.  If you’re ready, willing, and able, men (and those assigned male at birth!) are able to achieve mind-blowing multiple orgasms without even having to touch their cock at all.

Some men can even cum from anal orgasms alone, with their penis shooting out cum hands-free. It’s quite a spectacle!

However, milking your prostate is no walk in the park, whether you’re doing it alone or with a partner. The benefits and sensations of prostate massage are gargantuan, but getting there requires time, patience, practice, and some new male masturbation techniques.

There are also additional hang-ups for some curious men, such as the stigma around anal play in straight (and some gay!) men, but in this guide, we aim to answer all of your questions about prostate milking techniques, expectations, benefits, tips, and more!

Chapter 1:

What is Prostate Milking?

“Prostate milking” or “prostate massage” refers to the stimulation of the male prostate gland. This gland, which is sometimes referred to as the “P-spot” or “male G-spot” is a walnut-sized gland which is located inside the rectum. It’s not very deep into the rectum – it’s only a few inches inside.

Where is the prostate?

The prostate is located between the penis and the bladder. This gland is essential to male sexual functioning, secreting a fluid which helps to protect your sperm. Coincidentally, it is also intrinsically linked to the male orgasm, and prostate massage has to potential to produce incredibly strong orgasms in men.

How do you stimulate it?

Using a finger or reputable sex toy, you massage the prostate either internally or externally. Although external prostate stimulation can lead to some pleasurable sensations, internal stimulation is much more intense and enjoyable for most men. Everyone likes different kinds of stimulation; some enjoy the gentlest pressure or muscle contractions, while other men may like to hit their prostate quite hard in order to feel the pleasure. There are a variety of prostate toys available, such as vibrating prostate massagers and hands-free prostate toys.

Aren’t anal orgasms for gay men?

The pleasure that gay men feel when receiving anal sex is largely due to their prostate gland being stimulated by their partner’s penis inside their ass. There are even some prostate orgasm porn videos of gay men getting fucked with titles such as “hitting his prostate” where the “bottom” partner is seen cumming from anal without any penis stimulation at all. It’s extraordinary.However, this should not deter straight men from taking advantage of the male anal orgasm. At the end of the day, every man is born with a prostate which can be milked for maximum orgasmic pleasure – it’s not something that is exclusive to gay men… they just got lucky! If you want to milk the prostate and achieve otherworldly sexual sensations, you need to let go of the idea that anal orgasms are only for gay men.Even though prostate orgasms concentrate on your anal G-spot, they don’t really “simulate” the feeling of anal sex anyway. In other words, it’s not like having a cock pump in and out of your ass, per se. However, the sensations that it produces within you are similar to that of receiving anal sex, with waves of leg-quivering pleasure radiating throughout your body. Basically, if you want to achieve multiple continuous orgasms and maximize the pleasure that your body can naturally give you, then you’re going to have to get past the idea that prostate milking is “gay”. Have you ever met a gay bottom? They have the best sex in the entire world – they’re getting their prostate stimulated every time they shag. All men should be taking advantage of this natural anal G-spot!

Chapter 2:

Preparation & Cleaning

New to putting things inside your ass? Welcome to the world of anal play preparation. It’s not fun and it’s not always easy, but it’s an essential step to take if you want to keep things clean and avoid any nasty surprises.

Even if you’re used to anal play, there are additional steps which are advisable for prostate play, so be sure to give this a thorough read.

Cleaning your bottom

Poo comes out of your bottom, as you probably know. Do you know what’s a turn-off for the vast majority of people? Poo. So make sure that your bottom is clean before going up there – it’s not the sort of thing that you just chance.

  1. If possible, have a “clean” bowel movement which isn’t messy or runny. This will clear the way for insertion. Try to eat a healthy diet with lots of fiber, as this will keep your poops uniform and “neat”.
  2. Next, clean your asshole with a babywipe or toilet wet wipe, getting rid of any fecal matter on the outside.
  3. At this point, you may want to douche your anus to make sure that it is thoroughly cleaned out inside. There many websites with tips and guides on anal douching if you’re new to it.
  4. After cleaning out your ass, you may want to have a shower to get rid of any nasty smells or bits and pieces which may have come out during this process.

Because the prostate is only 2-3 inches inside your rectum, you don’t need to go mad with the whole bum cleaning thing. Sometimes your bottom will need less cleaning than others, and other times it may just be a no-go-zone for the night. In time, you’ll get used to knowing when you’re clean enough for prostate play. And at the end of the day, if a little bit of fecal matter does come out, it’s not the end of the world. Put a towel down and get over it – it’s only a little bit of poo.

If using fingers

If you’re attempting to reach anal orgasm by having your (or your partner’s) fingers inside your ass, you should ensure that your fingernails are trimmed and clean. The last thing you want is dirty/pointy fingernails inside the rectum, as this can cause tears and uncomfortable feelings.Also, if you’re not used to it, reaching around inside an ass can be a little strange. For this reason, some people prefer to use a glove or condom as a barrier between the finger and the prostate, helping it to feel a little less weird and direct.As always with anal play, make sure that your finger is adequately lubed up with a high-quality anal lube. Everyone likes different lubes, but water-based and silicone-based lubes tend to be the most recommended for anal play.

If using a prostate toy

If you’re using a reputable prostate toy brand such as Aneros, then the prostate massager toy is going to be shaped so that it ergonomically fits your body, making it easier to insert and feeling quite “natural” once it takes its place.

First, be sure to clean the sex toy with warm soapy water or specialized sex toy wipes before use. Before putting something in your ass, ask yourself “would I be willing the put this in my mouth?” If the answer is no, then you need to clean it. Never put something dirty or dusty inside your bottom.

Before putting something in your ass, ask yourself “would I be willing the put this in my mouth?”

Next, put a towel down on the bed and lay down. Lube the prostate massager up with plenty of water-based ​lube before insertion. You may want to “warm your anus up” by lubricating your finger and fingering yourself for a few minutes with 1 or 2 fingers. This helps your anus to relax and expand slightly, making more room for the toy.

Getting into the “zone” for prostate play

It’s called a “prostate massage” for a reason – you really need to be in a relaxed and meditative state of mind. I know saying that you need to be in a meditative state sounds all hippie-ish and weird, but believe me when I say that it’s true! Calm your body and your mind, think arousing thoughts, and get yourself excited for one of the best orgasms of your fucking life. This meditative state of mind helps to trigger and stimulate the muscles inside you which are going to give you intense pleasure later on. It’s very hard to describe if you’re not used to these sensations, but it’s almost like you have to get your butt “excited” for this pleasure before it evens happens. The more “excited” your ass is, the more readily it produces anal orgasms.

Also, breathing is really important with many kinds of prostate massage – make sure that you take deep and long breaths, allowing your body to feel all the sensations of the massage as you slowly inhale and exhale your breath. Try to be as mindful as possible with your breathing; it’s an essential part of the process. Practicing mindfulness meditation in your everyday life could actually be a huge help here.Hands free prostate orgasms are not the sort of things that can be achieved in a quick 10 minutes before you catch the train – this is the kind of thing you need to set a couple of hours aside for. Ideally, you want to be home alone (you’ll want to moan loudly) and you’ll want to have 1-2 hours of time without any distractions. If you can plan for 2+ hours of free time, then that’s even better. Don’t rush, as rushing will get you nowhere with this kind of erotic milking.

Chapter 3:

Prostate Massaging Techniques

Looking for those coveted prostate stimulation techniques which produce multiple long orgasms? Then you’re in the right place! Although couples erotic prostate milking can be fun, solo internal prostate stimulation with a high-quality sex toy is the best way to ensure a leg-quivering body-shaking continuous anal orgasm, sometimes referred to as the “Super O” in online prostate milking communities.

If you’ve seen prostate orgasm videos of men rattling around on their beds in pleasure and you want to want to know the best way to achieve prostate orgasm, keep reading.

If using your finger (or a partner’s finger)

Although not the best prostate massaging technique, milking the prostate with your finger (or your partner’s finger) could be a good introduction for newbies who are unfamiliar with this kind of anal play. Use a clean and well-lubed up finger, insert it into your rectum around 2-3 inches. You want this finger to be about 2 knuckles deep inside you. You may wish to use your index finger for this, although I find the middle finger to be best personally.The prostate gland is located on the anterior side of your body, so once you’re inside your ass, you want to curve your finger towards the front of your body, almost like you’re moving toward the direction of your penis from inside your ass. With any luck, you’ll feel a walnut-sized “bump” around this area. This is the prostate gland.Use your finger to gently “rub” or “tab” the prostate gland, getting used to the pleasurable sensations that it creates. This kind of prostate stimulation tends to be best accompanied with cock massage and penis masturbation, so try to adopt a position which makes it easy to stroke your cock and jack off while also milking your prostate.

If using a vibrating prostate massager

Vibrating prostate toys are a good step up from finger play – they get you accustomed to prostate stimulation and having a male sex toy inside your ass for extended periods of time. You might think that a toy which vibrates would be the “ultimate” pleasure for your prostate gland, but this is not true, as the vibrations tend to “numb” the area over time. Alas, it will feel relaxing at first, but then the numbing effect will take over and the pleasure will become less noticeable. Still, it’s a good middle step for prostate play.After preparing your ass and washing the toy, use a lubed-up finger to loosen up your asshole a little. You need don’t to go too far in – just 2 or 3 inches should do – as we’re just trying to loosen up and relax the anus at this point, making it more ready for a toy to be put inside it. Use 1 or 2 fingers and take a good few minutes to loosen up your ass.When you feel relaxed and open enough, lube up the sex toy with water-based or silicone-based lube and then insert it into your anus with the prostate-stimulating end facing toward the “front” of your body, as if pointing toward the penis. Most manufacturers of these vibrating anal toys will include diagrams which show how their toy is supposed to slide into your rectum, such as this one  and this one. Once it’s inserted and your body becomes accustomed to it, simply turn on the vibrations and enjoy! Start soft and work your way up to the bigger pulses – you don’t want to jump in at the deep end. When it comes to prostate masturbation, it’s about the journey rather than the destination! Again, you’re unlikely to experience the Super O anal orgasm from a vibrating toy, so feel free to stimulate your penis and scrotum along with the sensations of the toy.

If using Aneros-style prostate sex toys

You really want the best male orgasms that leave your body shaking and legs quivering with pleasure? Then acquaint yourself with the Aneros sex toy range. These sex toys feature patented designs and 100% medical-grade silicone, ensuring an amazing and safe road to your first anal orgasm. Aneros actually make the only medically patented prostate massagers in the world, with their unique design absolutely maximizing anal pleasure for men. The downside? They require practice.Before using Aneros devices, you need to acquaint yourself with your sphincter muscles (the ones you squeeze when pooping) and your PC muscles (the ones which stop you from peeing). The PC muscles (pubococcygeus muscles) are the trickiest to get used to contracting/relaxing, but doing some kegel exercises should help you to strengthen them. These PC muscles are quite subtle and it takes some time to find them, so don’t lose hope. It feels a bit like you’re “pushing out” up to your groin, but everyone describes this feeling differently.Place a towel down and lie in a comfortable position. For the best prostate stimulation results, most people recommend lying on your back with your knees bent up and your feet flat to the floor. Some people also find that lying on their side is pleasurable, especially if they bend their knees up toward their chest. Aneros actually recommend lying on your side and bringing one of your knees up toward your chest as high as you can – this is said to grant the easiest access to the prostate, but may not be the most relaxing or comfortable position.Get your anus ready by lubing up your finger and fingering yourself with 1-2 fingers for a few minutes. This should help to loosen up your ass and relax your sphincter muscles a little. Next, lube up the toy and gently insert it inside your bottom with the prostate-stimulating end facing “upwards” toward your penis from inside you. The perineum pressure point should gently rest on your perineum, which is sometimes called a “taint” or “gooch”, helping with external prostate stimulation.

Now there are several prostate masturbation techniques which are possible when using Aneros-style prostate massagers, but here are the 2 main techniques which most users (and myself) have found to be effective:

#1 – The “Tug Of War” TechniqueThis prostate milking technique is all about forcing the muscles in and around your anus to spasm, leading to involuntary muscle spasms which cause a chain reaction that you cannot stop once it starts.With the Aneros sex toy comfortably inside you, contract your sphincter and PC muscles, holding them for around 7-8 seconds before releasing them again. Repeat this approximately 20 times. After a while, these muscles will start to get tired and you’ll feel that they start to “wobble” as they spasm on their own.Now you should continue with these long contractions, but don’t squeeze the muscles as hard. Instead gently contract the muscles at around 40-50% their maximum amount, holding them there was as long as you can before relaxing and starting again. With any luck, this will start to cause involuntary spasms from both your sphincter muscles and PC muscles.Keep gently contracting these muscles at 40-50% and holding them there until you get to a stage where your body will take over and do all the spasming for you. If you get to this point, you start to feel extreme pleasure radiating throughout your body, extending to your penis, anus, and down your legs to your feet.Now you’re on the road to a “super O” male orgasm. Relax and accept the new sensations that are occurring inside your body. If the sensations die down, gently contract the muscles and hold them in place again until the sensations return. Do not assume that tighter contractions lead to bigger orgasms – it’s all about gently coaxing your body into involuntary orgasms that build… and build… and build. DO NOT force it – just let your body take you on this magical erotic journey.

#2 – The “Do Nothing” TechniqueYes, you heard that right… the “do nothing” technique. This technique is best for people who are experienced in the art of anal G-spot stimulation, as it requires a lot of focusing, meditation, relaxing, and arousal.With the Aneros sex toy sitting comfortably inside your ass, relax your body and think erotic thoughts to get you into a sensual mood. Make sure that you’re in a comfortable environment with no distractions and ensure that you can relax and fully concentrate on your anal play session. Breathe slowly and deeply, staying mindful of your breathing and how the sensation of moving your chest in and out gently affects the toy inside your ass.Now start to concentrate on the sensation of the Aneros toy inside your ass. Feel it inside you and allow its warmth to radiate throughout the surrounding muscles. When you have a foreign object inside your ass, your body naturally wants to tense its muscles up, even very slightly. This process is all about accepting the Aneros as a new part of you and allowing your bottom to fully relax around it and accept it.While concentrating on the sensation of the toy in your ass, try increasing your arousal by playing with your nipples, talking dirty to yourself, and imagining erotic thoughts. The is very much a “mind over matter” technique – the more “turned on” and erotic you feel, the more likely your prostate is to “wake up” and cause pleasurable sensations.After a while (often 30 minutes or more) of relaxing and turning yourself on, you may start to feel some involuntary trembling from inside your ass. This is the muscles around the prostate toy starting to tremble and spasm. Do not tense up or fight this feeling – go with it and allow it to continue.If you allow yourself to remain aroused and relaxed, then the trembling muscles inside your butt will begin a chain reaction of spasms which cause the Aneros toy to bump into your prostate repeatedly. This can start to feel very intense and unusual, but DO NOT fight the sensations. You will feel pleasure radiating throughout your entire body and down to your extremities, and with any luck you’ll be able to achieve the coveted Super O continuous orgasm that men are constantly searching for. If you feel the sensations die down without resurfacing, very gently contract your PC muscles and hold them in place for a few seconds before relaxing again. This is usually enough to bring back the trembling and lead you toward a toe-curling hands-free prostate orgasm.

Make no mistake – these 2 techniques are the best ways to achieve prostate orgasm. If you want to know how to milk yourself and cum from anal stimulation alone, then these 2 methods are the best way to do it. They will take time, practice, and patience, but these are the easiest roads to your mind-splitting toe-curling body-shaking first anal orgasm.

Chapter 4:

External Prostate Massages

If you want to experience the pleasure of prostate stimulation but you’re not sure if internal ass play is right for you just yet, perhaps you (or your partner) could try massaging the prostate externally by massaging the perineum. The perineum is sometimes called the “taint” or “gooch” – it is the area between your anus and scrotum that looks like it has a seam running down the middle.

Please note that external prostate stimulation is MUCH less effective than internal milking, so don’t expect mind-blowing results from this.

External prostate massage with fingers

Take your index finger, middle finger, and ring finger, pressing down together to form a sort of “triangle” of fingertips. Next massage the perineum by moving these fingers in a circular motion. Repeat this 6-7 times before changing direction. Rinse and repeat (not literally) to give yourself a relaxing prostate massage from the outside. This method is best combined with penile masturbation or it is unlikely to cause an orgasm. Some people may also prefer other variation on this, such as “tapping” their fingers on their perineum while masturbating with their free hand. While unlikely to cause a prostate orgasm, these methods definitely increase the intensity of regular cock massage and masturbation.

External prostate stimulation with vibrating toys

You could also use vibrating sex toys, such as vibrating bullets and eggs in order to stimulate your perineum, penis, and testicles. While these sensations are not going to lead you to an anal orgasm, they could introduce you to the feeling that anal orgasms generate, getting your body prepared for more intense orgasms that leave you tingling all over.

Chapter 5:

How do Anal/Prostate Orgasms Feel?

Now you might find yourself wondering “what does an anal orgasm feel like?” Well, to put it simply, they feel fucking amazing. Imagine the best orgasm you’ve ever had, times it by 10, radiate it throughout your entire body, and then prolong it to last several minutes at a time without stopping.

There’s a reason that people are willing to shell out their hard-earned cash for prostate stimulation toys – the orgasms are absolutely unbeatable. By contrast, normal orgasms will start to seem a bit crap.

My personal take on anal orgasms

Everyone has different experiences and sensations of prostate orgasms, but for me, the sensation was like a warm “glow” of sexual energy which radiated from my anus out down my legs to my toes and up my arms and out to my fingers.

I felt about as turned on as I’ve ever felt in my entire life – it was like my entire body wanted to give itself over and surrender to the immense sexual pleasure I was feeling.For me, the feeling was not like a regular penile orgasm – it’s like being on a whole new level of sexual pleasure that you cannot imagine until you experience it for yourself. Your muscles twitch and your body can shake, yet your bottom and your penis are glowing with a warm sense of erotic calm. I personally find that there is a very unusual contrast between my muscles twitching/spasming and my inner core feeling a calm sensual relaxation. It’s like I’m caught in the middle of a fight between all the muscles in the body – a fight which leads to intense sexual pleasure. The so-called p-waves (waves of prostate-related pleasure) could leave me feeling tender and euphoric for several seconds or even minutes at a time, often causing me to involuntarily moan out there or bite my lip as I neared the ultimate climax. I’d be leaking precum after a while, and sometimes my penis would throb without me even having to touch it. It’s fucking awesome.

Other people’s takes on anal orgasms

Here I’ve compiled some of my favorite comments from this “Ask Reddit” thread where Reddit users who had experienced prostate orgasms were asked to describe them:

When it hit, it fucking hit. A wave smashing into my groin, wave after wave smashing over the rest of my body. My skin felt super receptive. I felt every hair follicle on my scalp, and I felt a pressure building again. I had ended up groaning again, quite loudly, and shot across the room. Multiple volleys of semen flew across the room, managing to hit the opposite wall.

It’s difficult to describe, because they come about in several different ways and in several different parts of the body. It’s a very bright, tingly sensation, ranging from subtle to overwhelming. Prostate stimulation, even without achieving prostate orgasms, can make normal masturbation feel much better, multiplying the intensity of the regular orgasm to come.

For me, I find that I am simply overcome by the sheer power of the orgasm. It’s not a whole lot better, per se, but it is a lot stronger. As in after it happens I’m stuck there out of breath and trembling for at least a few minutes. As if all of my energy had just been sucked out of my body and concentrated into a ridiculous orgasm. P-spot is the way to go.

It feels like you’re brought to the brink of orgasm, but you stay there for a long time before the pleasure just takes over and you explode.

I couldn’t have said it better myself!

Chapter 6:

What to expect from prostate orgasms

This section is all about getting you ready for a new kind of orgasm that you’ve never experienced before.

We’ll talk about what you can expect, the side effects, the aftermath, and everything else you want to know about the elusive wonder of prostate milking orgasms.

Cumming and precumming

This might seem strange, but with prostate orgasms, you don’t always cum. You see, rather than reaching a destination, prostate milking is all about enjoying the journey. You could experience multiple orgasms through P-spot play, and you may also notice your penis convulsing and leaking vast amounts of precum. However, you may not necessarily cum from this form of anal massage, although it can indeed happen. Let go of the idea that “cum = orgasm” and go with it.

Trembling and body shaking

If you’ve ever watched prostate orgasm videos of people using the Aneros prostate toys, you may see their legs trembling and their bodies shaking all over their beds with pleasure. If you do manage to achieve prostate orgasms, then this could happen to you too. Don’t worry, it’s perfectly safe (assuming you don’t do it 24/7) so when it starts to happen just go with it and keep enjoying the ride. Your body will feel shaky and wobbly once you finish your session, so make sure that you prepare for this in advance.

No penis stimulation

If you’re trying out P-spot massage for the first time, it will be incredibly tempting to play with your penis and masturbate at the same time. DO NOT do this unless you’re in a hurry to cum. While it is indeed erotic and will make you feel more aroused, jacking yourself off while having your prostate massaged is likely to make your cum more quickly, and male anal orgasms tend to need around 20-30 minutes to get going before you really feel their bliss.

After effects

After an intense prostate milking session, you might find that your body is incredibly sensitive and shaky for a while. I also personally find that my prostate is very sensitive for the next day or 2, making me feel hornier than usual while doing everyday errands.

For example, driving a car or sitting in certain positions can involuntarily stimulate my sensitive prostate gland, causing me to run off in search of the nearest bathroom where I’ll feel the overwhelming need to jerk off. It sounds fun, but it’s actually very inconvenient when you’re trying to concentrate on non-sexual tasks.

Chapter 7:

Scientific benefits of milking the prostate gland

There are many scientific studies which have examined the health benefits of prostate massage. For a long time, doctors actually recommended prostate massage to patients because it could help to treat a wide range of conditions that we’ll talk about below.

Aneros actually started as a medical equipment company, creating prostate massagers in the 1990s which were designed for medical treatment. Soon they realized that their massagers were being used for sexual pleasure more than treatment, so they patented their designs and became a prostate sex toy company!

Erectile Dysfunction

Prostate massage was a common treatment prescribed for people suffering from ED, and many people with erectile dysfunction use prostate play in addition to other modern treatments to help elevate their libido.

Prostate Cancer

In the US, 1 out of 6 men are diagnosed with Prostate Cancer in their lives. However, according to the Sperling Prostate Center, prostate massage can help to reduce men’s risk of Prostate Cancer. It is thought that stimulating the prostate regularly (i.e. moving it around) makes it much more difficult for a tumor to grow.

Urine problems

Sometimes your prostate can interfere with your urethra, making it difficult to pee properly. By massaging the prostate, it can help to move it out the way/relax it and stop any urine flow issues.

Ejaculation issues

If you suffer from painful ejaculations, there may be blockages in your fluids system which are getting in the way of your semen. Massaging your prostate and the surrounding area could help to “undo” any kinks and reduce blockages.

Chapter 8:

Prostate massage troubleshooting – tips if you’re getting nowhere

Don’t worry if you’re getting nowhere – I used to be you, but I got past it! It’s common to have problems finding your prostate and stimulating it properly, especially if you’re using advanced prostate toys like the Aneros range. Here are some common tips to help you reach the continuous orgasm that you’ve been dreaming of.


Breathe deeply and breathe slowly. Concentrate on the sensation of your breaths and how they subtly affect the sensations building up inside your ass. These deep breaths not only help to cause contractions in your body, but they also help you to relax. You can’t achieve anal orgasm if you’re not relaxed!


You might find that your prostate is more effectively stimulated by changing your position up a little bit. Some people like to lie on their sides with their knees bent up toward their chest, while others like to lie flat on their backs with a pillow beneath their butt. Some people even like to lie on their front… try a few different positions and see which one most effectively stimulates your prostate.

Tensing Up

If you’re not used to anal massage, it’s likely that your body will naturally tense up and try to fight against what’s happening. Bear in mind that it can take quite a few lengthy sessions to really get used to anal masturbation.


With all this concentration and meditation going on, it can be easy to lose your horniness and arousal while in the throes of a lengthy P-spot milking session. If this is the case, try playing with your nipples, thinking erotic thoughts, talking dirty to yourself, and moaning out loud. The more aroused you are, the easier it is for your prostate to respond and do its thing.


You cannot rush a prostate milking session, with some websites reporting that it can take around 10-40 minutes in order to achieve anal G-spot orgasms. However, many people suggest that you should allow 1-2 hours for a prostate milking session as a minimum. If you need to run some errands in an hour, you shouldn’t be milking your prostate. The best time is probably before bed, when you’re in no rush and your body has time to recover from the intensity.

The Bottom Line (pun intended)

Prostate massage will change your life. It will increase your libido, make masturbation feel better, and introduce you to a new level of orgasm which is far beyond anything you’ve ever felt before. The only downside of self prostate milking is that it can get a little addictive! In fact, one man in his 60s even became addicted to prostate orgasms and couldn’t stop having them!

Nonetheless, if you’re sensible and use the appropriate preparation, technique, and caution, then you can open up your mind to a whole new world of sexual sensations. Who knows, maybe you’ll even achieve the “Super O” that people are always talking about! Prostate stimulation needs to be tried by all men at least once in their lives – you don’t know what you’re missing!

Written by


  • David says:

    I’m loving the experiments. Haven’t reached the big o. But am determined.

  • Alesia says:

    I’ve been married to my husband for 30 years. A few years back he began to divulge his desire for anal. It’s been very difficult for me as a woman to adjust to the introduction of a new step in our sex life. I mean ever since I started having sex I always knew what and where my role/place was in the process. This new thing has had me thrown off my game. Your article has been a great help to me! Do you have something written for women going through my same situation? If so I’d love to read it. Thank you.

    • JC Ways says:

      I don’t have an article written, but it’s important to remember that we’re just conditioned to enjoy old-school penis-vagina sex (for straight couples) because it’s the way that makes babies happen. Men have a G-spot inside their ass, so it makes sense that they’d want to explore it during sex. While anal play is obviously commonly associated with gay men, I think that the stigma surrounding anal play for straight men is starting to decline!

    • Bobby Maxwell says:

      Pegging has been quite popular over the last couple decades. You can purchase a dildo harness, dildo, and lube from Amazon shipped in a non-discript brown cardboard box. You’ll want a high quality silicone dildo. It is in no way a gay experience. Hell, there’s not even a second guy in bed with him! I’m getting on in years and decided to spice up our married sex-life (and improve my prostate health. If you don’t use it you lose it- libido and length! Take it slow and romantic with lots of hugging, kissing, and reassurance. Best wishes to you both! You can watch pegging videos for free on Youtube- BTW.

    • Bobby Maxwell says:

      Sorry! I meant Pornhub NOT YouTube!

    • Derrick says:

      I have been married for over 30 years and there is no way my wife would ever do this for me. It’s easier for me to just farm it to my local Asian massage parlor. Most of these women are experienced in this form of massage in their home country. The best money I’ve ever spent.

  • Old Lover says:

    Nearly 70, married for over 45 years to a generous sexual and beautiful woman. We love to masturbate – solo, mutual, and watching. However, the most intense orgasms I’ve had are via Aneros prostate massage – hands-off and solo. The description of p-spot waves and indescribable, prolong ecstasy are spot on. My technique is to sit in an Adirondack chair position and use my arms to prop me up and skillfully pressure and stimulate my prostate. It takes at least an hour and lots of nearly, orgasmic PONRs edging. These edging moments are unbelieveably pleasurable. The key is to relax and enjoy (absorb) the sheer pleasure. Then one of the edgings with take you over the PONR in amazing waves of ecstatic orgasmic pleasure. I’m always spent and indeed my prostate is in a state of bliss for days.

  • Robb says:

    Until I read the article above, I had never had a full body ”Super O” without doing what I consider cheating.. They are truly incomparable to cumming.
    To say that they are 10x stronger is an understatement, they are more like a female orgasm and last 10 x as long as a male orgasm.

    I honestly had a “ Super O” the first time both on accident and without a toy.

    I was alone, relaxing watching music videos.. Some categories are mostly sexy like RNB.. I mention this as music can actually intensify and drive the waves, it is better with more base. If your orgasm lasts long enough “minutes for me” and if it is repetitive as mine are, ( It will repeat until I’m exhausted or I intentionally quit.. with 5-30 seconds between each orgasm ).. Once, I did have a couple of hours almost involuntary O’s and had to get up and move around/distract myself to stop.. It’s advantageous not to masturbate until you want to stop, as cumming will generally make you want to quit, just as it does with sex – for me at least.

    You may want to comment or sensor a portion of this Or give a at your own risk safety warning as this is one individuals experience and discouraged generally for others as if done excessively can have medical risks or side effects..

    The way I did it was by enjoying a few boxes of wippets (NO2) using a professional grade whip cream dispenser which you can load 3-4 cartridges easily.Do not take a break between.. This is necessary at the beginning.

    I do a modified Version of your breathing technique which is breath in deep and as you contract and squeeze your core muscles from your shoulders to your butt, including the Prostate, then hold your breath as long as you can, which will have a stronger NO2 effect initially.

    Once the O’s start, THEN you can slowly exhale AS you completely relax.. and repeat as desired. At this time, NO2 is no longer needed or way less (one cartridge every several orgasms for me until the next orgasm starts)

    Without the NO2,

    I have to use a prostate toy or even a slightly larger regular plug using the same breathing but longer core contraction technique or graduated time as above. It will take longer but they can be just as intense once you learn.. It is harder to repeat.

  • Nadia2 says:

    I love it, I used to use vigtables and different tools, then I moved to suck my own penis and drink my all orgazm , then I wanted more.. I learned slowly by exercise to bent my ericted penis to the back between my buttocks and step by step I learned to insert most of my penis inside my ass hole .. fucking my self nothing compared to it .. very maximum joy and gave me crazy double orgazms followed by several strong ones in a minutes. … , then , I fall in love with four times with boyfriendS, and ten times with girls. .. I am now bisexual.. but I love my boyfriend to do it to me, I enjoy feeling stimulating and seducing him , then feeling enjoyed his powerful desire in me, drive him more than he can take to fucking me. .. when he is over limited and doing me with love, I get my orgazms five times in sequence. ..
    When I want to seduce him more and drive him crazy I make love to him softly first, then insert a toy big one inside his ass , then take him between my arms , kissing him, and I am ready for his huge lovely hot penis … love

  • Alex says:

    66 tried external massage WOW!!!! Best most amazing orgasm I have ever had !!achieve Super O with external massage the 10-45 minute sessions I have my most pleasurable stimulation times just massaging my taint slowly starting and faster and firmer when having the multiple body vibrating orgasms that make my entire body quiver.Thanks for the tips n I’m forever grateful and love my personal time daily!!!

  • Chris says:

    hi, we are married and practice long term chastity. I read that it is possible to milk the prostate without orgasm and even without taking off the cage. We also Wonder if the prostate is totally milked, is it possible to have an erection but unable to achieve an orgasm (to be a sex-toy for “Madame”). I’m very sorry if all of this is not appropriate.

    • JC Ways says:

      Hi Chris, everything is appropriate! Men can experience prostate orgasms (or strong feelings of pleasure) while in chastity, yes. You would be able to gain an erection after prostate milking and you would be able to cum, yes.

  • Charles Van Leuven says:

    New advice for me. New to this type of sex. I have oral sex my whole since 10 years old. New it then I was Homosexual- lived bi. Oral!! Never had anal but it’s time.

  • fitoru says:

    This article is cool. I enjoyed reading it a lot. Looking forward to seeing more from you.

  • Peter says:

    Thanks for the well written description/guide
    I have yet to reach the super o
    So far all my attempts are pleasant but don’t progress beyond the “trembling” reactions
    Will keep trying

    • JC Ways says:

      Yeah, a lot of it is about serious mental relaxation. The more relaxed you are, the more likely that the sensations will take over naturally.

  • Khalid says:

    Hi, I am afraid when using a massage game to become guy

  • Pete says:

    wow, cool article.
    what about electric impulses, are you familiar with that?

  • J says:

    My boyfriend’s desire for anal sex isn’t new to me and I’m also interested in it. We talked about this since the very beginning of our relationship. But since I’ve never done it with a guy nor a woman, I was really scared. I don’t want to hurt him at all.
    Our first try with fingers was hard on me because I hurt him a little and it made me feel really bad, so I told him to wait until I’m done reading about it and confident enough.
    I read a lot of articles but none had as much information as this one. I’m feeling much better now that I read clear information.
    I have almost all of the toys I want him to experiment ready. Now I’ll just read a little more, start things little by little and be patient.
    Thank you very much!!!!

  • Glans says:

    This is an excellent, thorough tutorial on a technique I am definitely going to practice!

  • S says:

    Does this new level of orgasm ever detract from your enjoyment in penetrative sex with partners, for example disappointment from comparing satisfaction and level of fulfillment?

    • JC Ways says:

      To be honest, yes a little bit. You can become a little bit addicted to the overwhelming orgasms. However, it’s hard to be aroused when you’re not with another person’s naked body physically, so there are pros and cons to both types of sex/orgasm.

  • Jacob says:

    This article was really helpful! I’ve been wanting to explore how to do this, but never knew where to start. I love your writing– keep it up 🙂

  • Marilyn says:

    I really enjoyed the article and have saved it for future reference when my husband wants to try it out. Question: If my husband is a bit afraid to try this, what do you suggest?

    • JC Ways says:

      Glad to hear that Marilyn. I mean the best thing you can do it just explain that all men have this “male G spot” inside their bottom and the orgasms will be AMAZING if he tries it properly. A lot of guys are afriad to try it cos it’s “gay” but it’s just about getting over that association of anal=gay.

  • Cynthia says:

    Who wrote this. I want to hire you as a content writer!

  • Danny says:

    I really need a prostate milking

  • J. says:

    I’ve read this and other articles on how to achieve this type of orgasm.

    The first time I used a rotating head massager without using the vibrate function. While watching porn, contracting my PC and sphincter muscles and breathing in while contracting and out when releasing.

    After about 20 minutes I noticed feeling flushed.
    25 Minutes I my PC and sprinter muscles started to flutter contracting on their own.

    All of the sudden the contractions turned to an involuntary continuous squeezing that produced an entire body orgasm. It lasted for about 30 seconds, I did not ejaculated. About 20 seconds later it happened again on and on multiple times for about 10 minutes.

    I could not control my body or the sounds I was making.

    When I was done I finished while masterbating and shot a load across the room. Not since I was a younger man had that happened!

    Afterward it took about 5 minutes for me to get control of my body and finish with the clean up. I litterally couldn’t walk.

  • Oral says:

    Good tips


    Go buy the njoy metal prostate curved dildo massager. Look up videos online of it. I love mine and guarantee you will cum like never before without even touching your cock whether its hard or soft, squirt after squirt…Love it!

    • JC Ways says:

      Oh yeah it’s absolutely amazing. I assume you mean the NJoy Pure Wand? I’ve had some real wild nights with that thing!

  • Jackson says:

    “Lube the prostate massager up with plenty of water-based or silicone-based lube before insertion.”

    Nooo! A lot of prostate massagers are made out of silicone, which silicone-based lube will RUIN. Maybe edit that out?

    • JC Ways says:

      yeah it depends on what the massager is made out of, hence the water-based lube being first 🙂

      I might edit it out for people who don’t know the difference… cheers!

  • Blaze says:

    So I’m married, I’m straight but I have stuck my finger in my ass and put a little plug up there just cuz it felt decent me and my wife where getting in the mood and I seen this so we tried the partner version and it felt really good did not have the super o yet cuz she wanted a turn but I will get there really wanting to know what it feels like to my self

  • Mike says:

    For many years, I was curious about anal sex. Although I enjoyed watching it in male porn, attempts with dildos, etc. always became a turn off for me. After experiencing some ED problems due to medications, I came across your site and read about the Aneros device. Just reading your descriptions made me horny so I took the plunge and ordered one. It has been a turning point in my life and one I certainly did not expect in older age.

    Your advice about how to approach anal sex is absolutely spot on the mark. It took about six or seven tries before I even felt comfortable but I persevered. I read and re-read the tips and followed them to the letter. Everything you advise is completely true. Before even starting the session, it is absolutely essential to become totally horny. I look at porn and photos, pull on a sexy jockstrap and begin to edge as I would in normal masturbation. When I’m completely turned on, I’m almost craving the penetration of the Aneros device. I find that slipping a lubricated condom over the probe makes insertion easy and comfortable. After a number of tries, I finally learned to relax and let the device slide right in. The initial sensation is amazing. I’ve experimented with muscle contractions and Kegels which really lead to an incredible sensation of arousal. That’s when I follow your advice about breathing and just enjoying the feeling within, especially when it touches the prostate.

    I let this go on for at least half an hour until I begin squirming with ecstasy. No need for porn because the brain just takes charge as all the various nerves are stimulated. Eventually, the muscle contractions lead to spasms and I begin moaning with deep pleasure. Precum oozes like I’ve never know before and tasting it just adds to the building pressure as orgasm approaches. Rather than masturbating, I often rub my upper thighs as my legs begin to twitch with anticipation of the coming orgasm. I’ve learned to recognize when I’m reaching the “zone” and now I’m able to stretch out the intense pleasure for as long as I wish. When ready, I let my libido have the satisfaction it has demanded for hours. That’s when the trembling begins and the heart-rate increases as all the muscles start their contractions. As I cross the point of no return, I start to pump load after load like when I was a teenager. The pulses and spasms are so intense and cannot even begin to compare with masturbation. Usually, I don’t even have to touch my cock as it stiffens and shoots its loads. I’m always drenched with cum. The spasms are completely uncontrollable and a couple of times I’ve tried counting. During orgasm, 65 spasms and contractions are not unusual. The ecstasy continues for long after I’ve ejaculated. A warm, satisfying feeling engulfs my entire body. I can only say that the level of excitement and pleasure is something I haven’t known since my teens and early 20s.

    So after getting all that off my chest, I’m feeling so turned on, I will have a nice long session tonight. I cannot thank you enough for the advice and descriptions you have given. It has really given me a new lease on life. For anyone reading your tips, I can only encourage them to try everything you recommend and take the time to be patient because it really pays off. I know this has been long but I had to share the joy I now feel about my sex life after several years of sadness and despair. Now I feel like the horny 16 year old I once was, jacking off five or six times daily. With the Big-O that anal sex provides, those five or six climaxes are now rolled into one sensational experience. Many, many thanks: “Mike”

  • Derrick says:

    I use the aneros and a kegel app I have on my phone. You are right about the breathing being important

  • Recent Blog Posts

    Jerkmate Games Review: A Look at the Best Interactive Cam Shows & Porn Games

    Looking to spice up your masturbation time? I hear ya. When you love watching cam shows while you slap your…

    Meet RoxxyDallas – StripChat’s Hall of Fame Cam Girl

    Ever played Have You Met? It’s simple, really. I’ll introduce you to one of StripChat’s sexiest cam models, RoxxyDallas, and…

    11 Cheap Cam Sites for free & low-cost cams [2024]

    Camgirls (especially good ones) can be expensive. And let’s face it… when you’re horny, you’re more likely to burn cash…

    Vibrations & More

    7 Things to Know About the Autoblow AI, Male Masturbation Toy Review

    With more men opening up to the idea of spicing things up with male masturbation toys, renowned brands have tried…

    10 Best FTM Sex Toys for Trans Men in 2024

    Finding the right FMT sex toys may feel like a mission impossible for trans men and transmasculine people. We’re not…

    13 Best Interactive Sex Toys in 2024

    I’ll just go out and say it – interactive sex toys are the best thing that has happened to the…

    25 Best Clit Vibrators For Women: Guide To Mini, Wand, and Sucking Clit Vibes

    37% of women need clitoral stimulation in order to orgasm. In fact, 64% of women use both clitoral and vaginal…

    5 Vibrating Panties to Rock Your World In Public [2024]

    Do you crave the thrill of a dangerous yet pleasurable public orgasm? If so, vibrating panties might be your new favorite…