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Push-Button Bliss: The Ultimate Guide To Prostate Massage

prostate massage prostate milking

My mind was completely blown the first time I had anal sex...

I thought that nothing could ever feel so good and when I finally came, I just couldn't believe there could be that much cum in one guy. It felt more like a religious experience than an orgasm.

That was the first time.

After that, I never really even got close to the same mind-warping cum bonanza when I got fucked. I just chalked the intense sensations up to the novelty of my first time and didn't really give it much thought for quite a few years.

That was back in my late teens. If only I knew then what I know now.

It wasn't until I started experimenting with sex toys in my mid-twenties that I finally got myself back on the track to prostate ecstasy.

While browsing the various toys at a sex shop, I came across a prostate stimulator that piqued my interest.

I talked with the store clerk a bit and they told me enough about it that I decided to pick one up and do some research.

I'm so glad I did!

As soon as I got home, I popped onto the internet and started researching prostate milking/massage.

I read up on the techniques and tricks and couldn't wait until I had a moment alone to try them out.

prostate massage male bum

That night, I got out the towels, lube, and all of the other goodies you need for a proper solo session and took the prostate stim for a test drive.

I lubed up, popped that baby in, and started doing what I had read on the internet.

It took some doing but I eventually started to feel an explosion of warmth all throughout my body, my dick got crazy hard and I was hornier than I could remember ever being.

An indescribable sensation started to roll through my body in waves that wouldn't stop.

Each flex of my pelvic muscles sending another fluffy wave of ecstasy coursing through my body and clouding my mind in a weird cottony bliss.

This was it!

This was what I felt that first time! Holy fucking shit!

I started stroking my cock and the feeling intensified. I couldn't believe that was even possible!

It only took a few more strokes before my balls began to twitch, my eyes teared up, outrageous amounts of precum started to gush uncontrollably from my cock and I finally blew a giant cable of jizz right past my head that Jackson Pollocked the wall behind me and glazed me from face to belly button.

I don't know how long I lay there afterward, dazed, glazed, and blissfully floating in that weird, all-over glow.

That was about a decade ago.

In retrospect, that first attempt with the prostate stim was clumsy at best.

I'm lucky to have seen results at all, considering how ham-fisted I was about it. Since then, my prostate game has, ahem, come a long way.

That night completely changed my life in so many positive ways. It gave me a new way to please and receive pleasure from my man, it cranked my already outrageous libido into overdrive, made my dick harder than ever, and even opened the door to the elusive multiple male orgasm.

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(B-Vibe Vibrating Remove Control Rimming Butt Plug)

Now, I find myself in a position to help other guys get in touch with a facet of their sexuality that is all too often completely ignored and I'm not going to waste it.

If the experience I described is something you want in your life, this prostate milking guide is exactly what you need to get you to the promised land!

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What Is Prostate Massage/Milking?

what is prostate milking?

First off, these terms are used interchangeably and mean the same thing. For the purposes of this piece, I am going to stick to "milking" from here on out.

With that out of the way, on to the good stuff.

Basically, prostate milking is both a medical and sexual practice where the prostate gland is gently stimulated until one or more orgasms are produced.

That's really the long and short of it. It's kind of in the name...

As accurate as that description is, it doesn't do you much good if you aren't even sure what a prostate gland is, where it is, or what it does.

Which is to say, the answer begs the question...

What Is The Prostate Gland?

what is the prostate gland?

Now for a boring but necessary clinical description of the prostate...

The prostate is a gland found encircling the urethra just behind the rectum. It is responsible for producing a fluid that nourishes sperm and releases this fluid into the urethra to mix with the semen during orgasm.

It is also a sensitive nerve cluster, which is why it's so pleasurable to have it stimulated. It's about the size of a walnut, give or take, and is slightly rough to the touch.

prostate milking massage

Chances are, that if you've done any amount of butt stuff before now, you're probably at least passingly familiar with your prostate.

You know when your playing in your basement funhouse and you hit "that spot"?

Well, that spot is most likely your prostate.

A little bump or nudge here and there isn't usually enough to produce a full-blown prostate orgasm, that takes finesse, but you definitely know it when you feel it!

Now that we know what a prostate is and what it can do for us, let's get down the business of getting yours milked properly!

male thong sexy prostate orgasm

"[The prostate] is also a sensitive nerve cluster, which is why it's so pleasurable to have it stimulated."


There Are Two Ways To Go About It

two ways to prostate massage: internal and external passage

There is an external and internal method for stimulating your prostate...

I have never once had even a twinge of success with the external method and I sort of relegate it to the realm of things that butt-scared straight guys do to feel kinky.

I find the only way to get the real deal is to go right up the ol' chute and straight to the source. I am going to focus strictly on the internal method for the purposes of this piece.

male butt dancing - prostate massage

Seriously though, I doubt the external method, even with guys it works for, would be as effective as going in deep with guns ablazin'. It takes a helluva lot more effort, but the results are undeniable.

If you are shy about digging around in your downstairs mix-up, this guide probably isn't for you.

There are plenty of simple guides for the external method out there for you to peruse if going in deep isn't in your wheelhouse.

Maybe you will have better luck with it than I did...

Internal Prostate Massage- Step By Step

internal prostate massage

Follow this step-by-step guide and you'll be well on your way to a whole new world of unbelievable orgasms.

I will be presenting the info mainly from the solo practice angle with a few couples tips but any and all of these tips also apply for assisted prostate milking.

Personally, I think it's best to experiment alone the for first few times to get a better handle on your body's limits and quirks.

Everyone's body is a little different and figuring out those differences before you let someone else poke around will help you communicate with your partner more effectively.

When it comes to assisted prostate milking, good communication is essential.

Step 1: Clear Your Schedule

prostate massage: clear your schedule

The first thing you are going to want to do is to make sure you have a pretty wide window of time to work with before you start experimenting.

Turn off your phone and make sure nobody will disturb you...

There's nothing worse than being greased up with your knees pulled back, two fingers deep in your funhole and hearing a knock at the door.

It's also important to make sure that you won't have any interruptions because your mood is a huge part of making your way to the PO holy land.

Which brings us to our next step...

Step 2: Preparation

prostate massage: be relaxed before you start

You want to make sure you are as relaxed as possible.

That means no scrambling around for something you need in the middle of your session, getting up for a drink, or having to stop to clean up an unfortunate brown mess.

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So, start by having a bowel movement a good hour or two before you plan to start rolling.

Lay out all of your toys, lube, pillows, towels, and anything else you are likely to need.

Make sure your toys are charged up if they require it, as well.

It is also helpful if you create a relaxing atmosphere in the room where you will be playing. Light some scented candles, play some soothing music, or whatever else you like to do to set a sexy, relaxing mood.

Then, take a nice hot shower to relax your muscles. If you have a partner assisting you, have them give you a nice, full-body massage to really get you loose and blissed out. Relaxation is another important aspect of successfully achieving a PO. Possibly the most important.

A hot shower is also crucial from a safety perspective because when you dig around in your ass you want to go in clean to avoid nasty infections.

Your anal walls are extremely susceptible to all sorts of germs so it's important to maintain high standards of hygiene. Clean up and trim those nails!  

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(Pjur Analyze Me! Relaxing Anal Glide Silicone)

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Step 3: Get Into Position

prostate massage: getting into the right position

Prostate milking gets better with experience, due in large part to the need to experiment with positions.

The position you that works best for you will depend on a number of things such as your body's unique quirks, whether you are using your fingers or a toy, which muscles you need to work to improve access to your prostate, your level of flexibility, etc.

Tantus Prostate Play

(Tantus Prostate Play)

Honestly, choosing the right position for prostate milking could probably warrant an article unto itself but there are a few positions that are generally effective for most guys in most situations.

Generally, I find it easier to achieve a PO on my back and that is probably the best place to start, especially if you have some help from a friend.

The most effective way I find to position myself is laying on my back with my knees spread in the air and my ankles drawn up toward my ass.

It's a little more difficult to reach around down there, but I find it positions my abdomen in such a way that access to my prostate is easier.

That's just me, though. Your results will almost certainly vary.

Another good way to go is to lay on your side and pull your upper leg up toward your chest.

This allows easy access to your rectum with toys or fingers and is pretty easy to maintain for longer periods of time.

Some guys find it easier to lay on their stomachs, but I find that extremely ineffective.

Different strokes for different folks!

The point is, you should take some time and experiment with positions to find out what works best for you. As always, patience is key here.

"Generally, I find it easier to achieve a PO on my back and that is probably the best place to start, especially if you have some help from a friend."

Step 4: Let's Go Spelunking!

prostate massage: how to get going

Alright, now it's time to dive in deep but it's best not to dive in immediately.

I cannot stress enough the importance of getting nice and loosened up down there.

Start by gently rubbing around the rim of your hole and to get things nice and relaxed.

When you're ready, slowly and gently insert your finger and start working your way deeper in.

At this point, you're not hunting for the prostate, you're simply getting your hole loosened up for the main event.

If you are using a prostate stimulator, you will likely find that the business end is significantly more girthy than the rest. Some guys might find the initial insertion a bit challenging until they are more practiced in the anal arts. Just use lots of lube, relax, and bear in mind that once you get past that initial hurdle, it's smooth sailing from there on out.

The main points to bear in mind for this step are relaxation and taking things slow.

Step 5: Button, Button, Who's Got The Button?

prostate milking guide

Now it's time to go looking for your bliss button.

If you've got a good prostate stim, this part can be incredibly easy because they are ergonomically designed to hit the spot when inserted.

I've found that, depending on the prostate toy in question, a bit of wiggling around is in order. Most prostate toys have a sort of hooking shape at the insertable end. You want this tip of the hook to curve up toward your belly when inserted. If it is hitting the spot, you will definitely know.

It's not shy about letting you know!

If you are using your fingers, insert them about two knuckles deep with your fingers curving toward your belly.

Personally, I find my prostate is a bit deeper than advertised and have to go a bit further in.

You're looking for a circular, raised mound that's a bit bumpy or rough to the touch.

Everyone is a little different and you will have to do some poking around until you find the spot. When you do, it will be incredibly obvious.

Step 6: Let The Games Begin!

prostate massage: prostate orgasm

Now that you've found the elusive bastard, it's time to start working it.

Right out of the gate, you should know that less is more when it comes to pressure and speed here.

Building a prostate orgasm is a slow process that requires a bit of patience.

You could be looking at spending an hour or more to get to the promised land but the payoff is worth it.

It's also important to point out that you should try not to touch or stroke your dick too much throughout the process to avoid blowing a load too early.

I find it helps to get a few strokes in here and there to bring me to the edge, but then I ease off. I don't want an OG orgasm, I want the real-deal Kobe beef of orgasms! Self-control plays a big part here.

If you are using fingers, start by gently rubbing your gland in a circular motion, varying the amount of pressure you apply.

If you are using a prostate massage toy, you will need to use a different method for stimulation because most toys are designed to be operated using your pelvic muscles.

Once the toy is in place, flexing your pelvic muscles causes the toy to rub up against your gland and gently stimulate it.

I find that a little manual manipulation of the toy helps from time to time, but a good P-stim should function hands-free.

As you begin to massage your prostate, you will start to feel warm waves wash through your body and you may experience an intense sensation centered on your prostate.

The type of sensation varies from guy to guy but many describe it as feeling like the urge to urinate or move their bowels.

This sensation gentles down a bit as you begin to massage and isn't anything to worry about.

It doesn't really hurt, but some men find this initial sensation uncomfortably intense. Muscle through! It's worth it.

Obviously, if you are experiencing actual pain, stop immediately and come back to it later.

The stars aren't aligned this time.

As you progress further you will start to feel your pelvic muscles involuntarily contract.

This is a sign you are on the right track. You will also likely experience an increased sense of "fullness" and a spreading warmth in your rectum.

These sensations will begin to build and you will feel the muscle contractions around your gland begin to intensify. It can be pretty intense, but stick with it!

Eventually, as the pressure builds and the contractions become more intense, you will begin to tremble uncontrollably.

If you're lucky, this will happen throughout your whole body and extremities but it probably will be centered mostly around your pelvic region and legs.

At this point, you are just skirting the edge of a full-blown PO.

Step 7: Batten Down the Hatches!

prostate orgasm guide

Around this time, the contraction and relaxation of your pelvic muscles will start to intensify.

The feeling of warmth and trembling will likewise become more pronounced and you will likely experience other effects. For instance, my eyes tear up as I approach the grand finale.

As you approach the point of no return, you will probably start uncontrollably leaking precum from the tip of your penis.

You will also probably be pretty shocked by the amount that starts gushing out.

At this point, you will probably also be experiencing intense waves of pleasure exploding through your body.

This is it! You're having a prostate orgasm!

Step 8: Ride It Out

multiple prostate orgasms

The great thing about prostate orgasms is that you can keep having them, one after another, if you play your cards right and the stars are aligned.

Once you reach the point that you are having a PO, you can continue to stimulate the prostate to produce multiple orgasms.

I've heard stories of lucky guys orgasming non-stop for 20 minutes straight on a good day.

Obviously, this isn't the case every time and you might not even be able to get multiples on any given occasion. It's just important to point out the possibility.

My personal best was 4 successive orgasms over the course of about 15 minutes after hitting my first orgasm.

I found multiple orgasms came with practice and it wasn't until my fifth or sixth session that I even achieved it.

When you are lucky enough to be able to do so, continue to stimulate your prostate until you've had your fill of orgasms or they just stop coming.

Step 9: Finish Off With A Bang

prostate milking: finish with a bang

Either right before or immediately after your prostate orgasms subside, you can start to actually masturbate the normal way to produce an incredible, traditional orgasm.

Prostate orgasms don't produce a refractory period, which means your wang is still ready and rarin' to go even after you've just orgasmed 3 times in a row.

Personally, I like to combine the old-school orgasms with the prostate orgasm by stroking my cock as I feel the run-up to a prostate orgasm coming on. I also like to wear a cock ring for added sensation.

Whenever you decide to finish off with a stroke, expect to see absolutely obscene amounts of jizz shooting at ridiculously high speed when you finally blow.

Seriously, you wouldn't believe how much splooge you can shoot until you actually see it. You'll definitely need a towel handy!

Step 10: Bask In The Glow

prostate orgasm, message, milking

I don't really know what other guys actually experience in the afterglow of a massive prostate orgasm, but from what I've observed, it looks a lot like what happens to me.

After I have a prostate orgasm, I find myself dreamily staring off into space, overwhelmed by feelings of sheer happiness.

I don't know how else to describe it other than that. There is nothing else quite like it.

The point is, don't just hop up out of bed and start cleaning up right away.

Enjoy the moment!

Take the time to let that peaceful, fluffy feeling of sheer joy wash over you and away before you come back to the real world.

sexy man ass - prostate play

Advanced Techniques And Tips

Now that you have the broad strokes of how to achieve a prostate orgasm, it's time to expand your repertoire a bit.

There are a few things you can do to help you fine-tune your prostate experience and streamline the process a bit.


Some Preliminary Pointers...

Put A Pillow Under Your Ass

Having a pillow under your ass raises your pelvis up and makes it easier to reach around down there.

It's also a great way to stay comfortable throughout the considerable amount of time it takes to get where you are going. 

Experiment with different thicknesses of pillows, if you can, to find the optimal position for you.

Arch Your Back

Sometimes the prostate isn't as pronounced as other times, making somewhat difficult to access depending on the situation.

I find that arching my back pushes my prostate forward enough that I can easily transfer the pressure to it through my anal wall to increase the intensity of sensation.

I also find that If I arch my back rhythmically as I flex my pelvic muscles and massage my gland, I get these intense, varied levels of pressure that are unpredictable and extremely pleasurable.

This little trick can cut some serious time off of how long it takes to reach orgasm. It also just feels damn good.

Get A Vibrating Toy

prostate massage sex toy

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Seriously, the difference is night and day here.

A good vibrating prostate stim will feature varied levels of intensity and, ideally, would also feature multiple patterns of vibration.

It should also be easily operated while inserted.

Look for toys with remotes or easily accessed, push-button controls to keep distractions to a minimum.

LELO Loki - Prostate Vibrator


I also like to start out with the vibration function turned off until things really start rolling and then turn it on to kick things into overdrive.

Obviously, everyone's preferences are different and you will have to experiment with what works best for you.

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(Aneros Eupho Syn Male)

SHOP PROSTATE MASSAGERS

Don't Skimp On The Lube

prostate massage lube

I find that the more lubed up my fingers or toy are, the more pleasurable the rubbing sensation feels on my prostate.

As I said, being gentle is a big part of prostate milking. You want to make love to it, not fuck it.

Swiss Navy Silicone Based Lube

Having a nice, gliding feeling that allows the pressure to smoothly roll over your prostate is a serious advantage over roughing it up with a dry toy or fingers.

All of that is aside from the obvious fact that butt stuff just requires a lot of lube to be good, in my opinion.

Treat your hole right and it will do the same for you!

SHOP ANAL LUBE

Don't Worry If Your Dick Stays Soft

erection prostate oragams

You're probably tired of hearing me say that relaxation is key but, shit, I just can't stress it enough. I'm not just talking about physical relaxation here.

Like the female orgasm, prostate orgasms are hugely dependent on mood and mental state.

So, anything that would cause alarm is going to be damaging to the experience.

There are few things more alarming to most guys than finding their dick is soft when they expect it to be hard.

Don't worry!

Prostate orgasms aren't about your dick! Personally, my dick gets ridiculously hard when I am playing with my prostate but I have known guys who stay flaccid throughout the whole thing.

Your dick might get hard, it might not.

Either way, you're still going to have an incredible orgasm. Don't sweat it!

Don't Worry If You Don't Blow A Load, Either

ejaculation prostate milking orgasm

For prostate-only play, you probably won't actually cum.

You will orgasm, no worries there, you just probably won't cum. Now, you will probably leak outrageous amounts of precum as you approach and experience orgasm, but you won't actually shoot a load unless you get your dick involved.

Be careful, though!

When you are stimulating your prostate, a traditional orgasm can be no more than a few strokes away and you could ruin your prostate orgasm by cumming the old-school way.

Edge, don't blow.

Bring A Friend!

partner play prostate orgasm

If you aren't using a prostate stim toy, it can be a bit difficult to poke around down there by yourself so having a partner is highly recommended.

That's not to say it's no good without help, only that everything is better with friends.

Getting as aroused as possible is a huge part of getting to the finish line and it's always easier to get fired up with a partner than it is to do so wanking by yourself.

Either that or you need a new partner!

Don't Be Too Goal-Oriented

Obviously, you have a goal but don't make the orgasm the focus.

Massaging your prostate is extremely pleasurable, even if you don't achieve a prostate orgasm.

Like I said earlier, a lot of your success will depend on your state of mind and focusing on the destination will just spoil the journey.

If you find yourself in a position where you don't think you're going to be able to make it happen, don't be afraid to pack it in for the night.

Just work it a bit while you stroke yourself off and you will have a pretty incredible orgasm, either way. You can always try again later.

Work Those Kegels

kegal prostate orgasm

A lot of the action involved with a prostate orgasm centers around your pelvic floor muscles.

These muscles flex involuntarily as your orgasm builds, but if you learn to control them better, you will find it a lot easier to achieve a screaming prostate orgasm.

I mentioned earlier how the prostate is more accessible or less accessible depending on a number of factors.

Things like arching your back can push it to the forefront for easier access, but Kegel flexing really brings it out of hiding.

Flexing your Kegels is also essential for the proper operation of most prostate stimulators.

They usually operate by being properly placed so that the business end is nestled up against the prostate so that when you flex your Kegels, it automatically rubs and massages your gland.

If you play your cards right, you don't even have to use your hands to achieve an orgasm after the stim is placed.

If you aren't familiar with Kegel muscle exercises, here's what you need to know to get started. The next time you take a leak, interrupt the flow mid-way. The muscles you flexed in your pelvis to halt the flow of urine are the muscles we are talking about here.

Now that you know which muscles need to be exercised, here's how to give them a workout. This exercise can be done while sitting, standing, or even lying down.

Flex and hold the muscles for three seconds, then release them for three seconds. You will want to aim for about 3 sets of 10 reps per day.

You might find that your pelvic muscles get really tired when you first start out and you might not be able to do as many reps as you would like until they become stronger. It's just like any other workout, really.

You start off weak and your muscles lack the stamina required for the workout, but they start to shape up pretty damn quickly if you keep at it.

The great thing about this exercise is that it can be done anywhere and anytime.

You could pound out some reps while playing phone games or waiting for the bus and nobody would be the wiser.

I would also recommend looking into other techniques to strengthen your Kegels. With just a little bit of time on Google, you can find all sorts of helpful tips, exercises, and even equipment to help you get a better pelvic workout.

If there is one tip that is sure to drastically improve your prostate experience, Kegel exercises would be it!

Pay Attention To Your Body

There are various mile-markers on the road to a prostate orgasm that let you know things are moving along according to plan.

It's important to pay attention to these signs of success as you go and take note of what you were doing to bring them about.

This will help you get to where you are going more easily as you become familiar with your personal prostate orgasm process.

Initially, you will experience involuntary contractions of your Kegel muscles. I also experience a spreading "glow" at this point. As things progress, you will begin to tremble, almost always in the legs but occasionally, if you're lucky, this sensation will begin to occur all throughout your body.

This is a good sign you are on the path to one of the big, full-bodied, face-melting prostate orgasms.

Finally, you will begin to uncontrollably leak oodles of pre-cum until you eventually explode with orgasmic delight.

Use these mileposts to chart the course for following prostate sessions and you will find it gets easier and easier as you become familiar with your body.

Communicate With Your Partner

communication prostate play

If you are working with a partner, communication is absolutely essential.

Let them know what is working and what isn't.

If they hit a particularly nice combination of rhythm, pressure, and speed, let them know!

When you are alone, you can listen to your body and let it guide you to where you need to be.

Your partner can't listen to your body, so you have to act as its mouthpiece to help your partner hone their technique.

Don't Get Discouraged

prostate milking tips

Prostate orgasms are notoriously fickle things, especially in the beginning.

It might take more than one session to make the magic happen. The important thing to do is to learn from each session and carry what works through to the next while dispensing with anything that doesn't.

Most guys don't have much success with their first few attempts. The guys who have the tenacity to keep trying will have their patience rewarded one hundred times over.

Hang in there! You'll get it!

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~ Final Thoughts ~

Prostate milking can be a bit tricky to get the hang of but the benefits are more than worth the effort. Aside from the physical benefits like improved prostate health, better erectile function, and even prostate cancer prevention, the introduction of new ways to pleasure yourself and your partners will do a world of good for your overall sexual health and provides an incredible outlet for your sexual energies.


Some of the brain chemicals released in massive doses by a prostate orgasm are the same chemicals linked to the process of pair bonding. This makes prostate massage an incredible tool for growing closer to your partner emotionally. When you are more connected with your partner emotionally, every aspect of your relationship will improve, from sex to just chilling on the couch all day binging the latest Netflix series.

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By putting these methods to work, you will be well on your way to having the most intense, literally life-altering orgasms imaginable. Don't take my word for it, though! The only way to know what you're missing is to find out for yourself!

Now that you have the low-down on how to flip your bliss-switch, the only thing left to do is flip it! Get out there! Experiment! Learn what works and work it! With a little time, patience, and practice, you will be cranking out earth-shattering orgasms like they're going out of style.

Just make sure you have plenty of towels on hand, though. Seriously, you've never seen so much cum!

SPECIAL OFFER: Save 15% off all anal toys, prostate massagers, and lube. Use Code: 0EG5V4V7VEAR at checkout. Exclusive for blog readers.



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