Who would have known that you have a fucking clitoris in your ass?
When you’ll reach your first prostate orgasm (PO), you’ll feel like you are living a dream…
You will be able to orgasm like your wife (again…and again).
When I first experienced my first PO I thought to myself:
“I’m never leaving bed again. lol.”
Suddenly all my orgasms from good, old-fashioned hetero sex and self-pleasuring seemed so pedestrian.
So as a straight male, I say to you:
“This is an adventure you want to take at least once.”
What You Are About To Learn Is Key To A Whole Different Level of Pleasure
In this guide, I collected the best advice I have & the stuff I learned after talking to hundreds of guys to help them experience their first ever prostate orgasm.
Many guys try it for years and don’t succeed.
The Prostate is a fickle partner.
I found that there were a lot of key factors that need to be there to have even a CHANCE of success.
To succeed with prostate milking it’s more like trying to put the 30-piece puzzle together than simply trying to finding one silver-bullet technique.
I call it a three-legged stool technique.
I believe there are three critical ingredients (& tons of subtle flavors) to prostate play success:
Those three ingredients are:
- The right prostate massager + the right lube with it
- The right arousal
- The right process (together with right expectations)
Here you’ll learn more about the arousal & the process.
I’ve covered the best prostate massagers here.
In case you’re wondering…
I found it impossible to give myself PO with my fingers.
I know pros can do it.
Pros can reach PO with just an external perineum massage and right breathing.
But you set yourself up for failure, if you have never reached the PO and try to just fiddle with fingers and hope for a bliss.
Sounds like a lot of work, huh?
But the rewards can be mind-blowing orgasmic:
A Man Describes How A Prostate Orgasm Feels Like:
“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.
When it was over I was still quivering. Gasping for air and trying not to touch my body. I grazed my nipples and nearly had a seizure. I cleaned myself off after 10 minutes trying to regain my composure. When I stood up I couldn’t walk. My knees were quivering with exhaustion.
It was intense beyond intense. Do try it.”
– Source: Reddit
Also if you’re serious about PO success, please don’t skip around though.
The order is very important and I spent over a hundred hours constructing it.
There is a method to this madness.
History & Health Benefits Of Prostate Massage
Prostate massage isn’t just for fun.
Though it will definitely bring you to a whole different state that feels like a RESET button on your life. A reboot of the system if you will.
But originally it was (still is) recommended by doctors as an aid to prevent prostate cancer.
You might even have had your first prostate milking experience at the doctors office (but he didn’t try to make it pleasurable).
The company that made prostate massagers (Aneros) in the 1990s discovered that men started using them more from pleasure than medical treatment.
That’s how this sex toy and prostate milking was born.
Is There A Correlation With Prostate Milking & Being Gay?
This seems to be the #1 stumbling block why most men don’t even try prostate play.
It stopped me. Years of society conditioning stood in the way.
But trust me: You are missing out.
I regret not starting a prostate play years ago.
I get it. It’s so vulnerable.
It takes time to rewire the brain.
Being penetrated is a totally different mindset.
But never experiencing Super-O is like…
…never orgasming for your whole life and discovering sex only at the age of 50.
The sensations are THAT intense. Blissful. Otherworldly. With no refractory period…(meaning) you can have multiple of those…
Sexual orientation happens in the mind.
You’re either attracted to men or you’re attracted to women (or both).
If you have mental blocks about this though, you need to solve them first.
I once consulted a guy who wanted to play with prostate but had a subconscious fear of rape.
His body was screaming against him playing with his ass.
He needed to fix his mind game first.
How Penis Ejaculation Compare With A Prostate Orgasm?
On a scale from 1 to 100, I would say penis is 10, and prostate is 100.
Yeah, penis orgasm is still fun, but the PO is quantum leaps better.
Penile orgasm originates in genitals, but prostate orgasm feels like coming deep within the body.
When it hits, it’s totally overwhelming and beyond this world experience.
But the best thing about prostate orgasm is that you can have multiple of them.
When you jerk off normally, ejaculation triggers a refractory period.
You cannot physically orgasm again for some time.
With prostate milking – you will orgasm without ejaculation.
And this will allow you to orgasm again…. and again…
You can chain those orgasms and have another one 5-10 seconds apart.
Ultimately the only reason you would stop is that you simply cannot take any more.
Pay attention because to succeed you’ll need to rewire your brain from penile sensations to internal prostate ones:
- “Prostate stimulation can be otherworldly. Like you are not sure where the pleasure is coming from. Penis stimulation, now, while still nice, is more to the point.”
- “Totally different. [Prostate stimulation feels] duller and less intense in the sense of concentrated excitement, but very powerful and intense in a more full-body experience way.”
- “It is a deeper, fuller, more encompassing pleasure, radiating from within the body instead of feeling like external stimulation.”
- “Penile stimulation is about certain external ‘hot spots,’ while prostate stimulation is all internal.”
How To Find Your Prostate (the P-spot)?
If you can locate the swollen prostate, you can hit it in any way you want.
The most sure-fire way to find the spot is to refrain from any sexual stimulation (it’s not that hard) for a week.
Note: If you don’t trust yourself to refrain, get a chastity cage to help.
You want to feel so turned on and aroused that you feel like almost humping the air.
You literally cannot think of anything else than sexual release.
That’s when you should put on porn for 20-30 mins with clothes on.
Without touching the penis.
You’ll feel the prostate become engorged and swollen as it fills with the liquid and grows 2x in size.
That’s when you want to go for normal jerk-off session and feel around your ass with a finger while you ejaculate (cut fingernails before to avoid hurting rectal walls).
P-spot will become a hard bump that there will be NO WAY you can miss it.
The picture below shows both sphincters, prostate location and the wall where the P-spot is located:
You’ll feel the P-spot as a change of texture.
You’ll need to get through two anal sphincters to be able to reach it.
First one, you can control and relax.
The second one will take time and patience to let you in.
Do this with a finger when you’re super aroused and close to orgasming and you WILL FIND IT.
How To Massage Prostate & Achieve A Prostate Orgasm (Step by Step) – Reality Check First
“Expectation is the root of all heartache.”― William Shakespeare
The quote above is there to symbolize the most important mindset shift you must forego.
The biggest hurdle for most people is to create a distinction between action and pleasure.
With penile stimulation you knew 100% you’ll get the reward in the end.
You stroke = wrrrr…the pleasure comes.
The prostate doesn’t work that way.
Be Prepared That You Won’t Have An Orgasm On Your First (Or Second Try)
Those are the bad news.
I’ve talked to tons of guys and on Aneros forums, a general consensus is that most guys figure out how to have multiple non-ejaculatory orgasms, within one year or less.
Very few guys figure it out either sooner or much longer.
It took me around a year, but I was really obsessed with it.
Wait wait wait…ONE YEAR?
Why would anyone keep going with it?
Because even when you don’t have orgasms, you’ll enjoy new sensations a lot.
And there is always a GUARANTEED ENHANCED normal jerk-off at the end.
The penile orgasm will be way more intense and the fireworks (amount of cum) will be unbelievable.
In fact, I would suggest you not to expect a PO in any session.
If you’ll push too hard, aiming for big-O, your mind will kick in and murder all chances of success.
Just enjoy the journey. Whatever happens, happens.
The prostate is fickle, and you cannot make it orgasm on demand.
But it helps to know that in the end there is always a reward with the enhanced normal jerk-off.
With that said, let’s get to the nitty-gritty:
Step #1 – Equipment: What You’ll Need For A Successful Prostate Milking Session
Yes, you can fool around with your fingers and in theory, you can achieve orgasm like that.
In practice though – it’s practically impossible to do it yourself.
The only exception could be a trained specialist.
If you’ve ever tried to stimulate woman’s G-spot you’ll know that your fingers will fall off sooner than she will reach orgasm.
I never succeeded to get the first prostate orgasm using just my fingers, and chances are you won’t either.
So what do you need for a proper session?
If you remember the three-legged stool technique:
The right toy and right lube are 1/3 of the success equation.
I wrote a separate guide about prostate massagers that you must read before you go on.
Here’s a quick version:
Both lube and massager are critical getting right.
For massagers, I recommend either Pure Wand or Nexus Revo.
Pure Wand is a manual toy.
Nexus Revo is 100% hands-free, that does it all for you.
The Best Lube For Prostate Play?
Sliquid Sassy is a popular water-based choice and the one I use.
However, you still will need to re-apply it in longer sessions.
That’s why oil-based lubes are popular for anal.
You’ll need to apply oil-based lube only once and it will be enough for multiple hour session.
The #1 recommendation is 100% unrefined shea butter (especially Now Solutions brand).
Or you can use grocery store baby-oil. All of these work great.
Oil is safe with all toys as long as you don’t use it together with a latex condom.
Here’s how you apply the lube:
- With a Sliquid you can use the enema bulb to squirt lube inside your rectum.
- With shea butter, keep it in the fridge and take out before use. Take two tiny scoops and insert them into your rectum.
- You can also add some lube on your finger and slowly put it in you.
- Spread some lube on the toy.
- Wipe your hands, insert the toy and wash your hands.
Alternatively, you can use disposable gloves or washcloth to keep your hands clean and dry.
Step #2 – Cleanliness Regime: How To Anal Douche The RIGHT WAY
Nobody wants more mess than is needed.
Not everyone needs to douche, but it depends on the person, their diet and how their body works.
It helps if you don’t eat anything heavy during the day (stick to raw things like veggies, fruits).
Then use a basic anal douche like this.
Here’s how to do the douching itself:
- Fill it with room-temperature water, sit on the toilet or shower.
- squirt it in and expel the water immediately. Like 5 secs tops.
- Repeat 2-3x, I usually don’t need to use more than one container of water.
Don’t keep water in longer than 5seconds, because that’s when it becomes an enema… and you DON’T WANT it.
Then take a nice shower, lie on soft towels and you should be all good.
If it’s still messy, consider changing the diet. Eating whole psyllium husk can be a game changer to make everything more solid.
Note: A clean-shaven perineum and asshole also help to prevent any discomfort that could be caused by a random hair being pulled by the toy.
Step #3 – Relax Your Mind & Prepare The Space
When monkey mind is running around it’s no bueno.
Arousal is a critical piece, yes.
But you need to find a way to relax your mind.
Also, make sure you do this only if you can get 1-3 hours of uninterrupted time by yourself.
This is not a quick release.
Few Ideas How To Relax:
- Smoke weed – I understand that this is not for everybody, but if you can get your hands to medical grade cannabis sativa, it’s an unbelievably easy way to just “let go”. Even just smoking a little weed will help you relax enough to kind of “discover” sensations that you will be able to remember when you sober up. Weed can be a great shortcut to achieving the first prostate orgasm.
- Take a long, hot bath to shut your mind to a point where you can just “be”.
- Through MeditationTake a deep, slow breath in through the nose in your belly and exhale through your mouth. (you can also download the Headspace app for 10 min guided relaxation)For the best results: count to 5 as you inhale, hold the breath for 5 counts and exhale for 5 points. Do this for 20-30 times.
I also like Tony Robbins Priming exercise (14.5min) to help with presence.
Few more things that you should do to prepare the space:
Porn can help to get you really aroused, but during prostate milking, it quickly becomes a distraction.
That’s where auditory stimulation comes to rescue.
You’ll be working on this 1-3 hours… and it’s tough to know what to do.
For some, it’s audio-porn listening to multi-orgasmic woman moans.
For some, it’s binaural beats.
For some, it’s Tibetan monk chants.
For some, it’s Hypno trainer type of stuff.
I suggest you download these audios on your phone ahead of the time and have 2-3 hours prepared upfront.
Here are a few recommendations:
- Shibby Says Erotic Hypnosis audios
- GoneWildAudio for various audio porn recordings
- Ramplefaps are cool, non-scripted, off the cuff masturbation audios
- 2h binaural beats music
You can, of course, keep playing porn, but just make sure you have a long playlist prepared so you don’t need to touch the keyboard or trackpad that will distract you from the experience.
Finally, prepare towels to place under your butt, get water close by and let’s get to it:
Step #4 – Taking It Slow: Getting Your Body In The Aroused State
Now that you are relaxed and everything is prepared it’s time to get aroused.
It should be easy if you took my advice and refrained from any sexual stimulation for a week.
You should be feeling horny in your body and excited for the play.
Now you can start with normal porn for 20-30 min while having your clothes on.
SUPER IMPORTANT: Don’t touch your penis during the whole session when you’re trying to go for prostate orgasm.
You want to rewire your brain from penile stimulation and discover completely new internal pleasures.
After the session, you can finish off with a jerk-off, but please, if you want any chance for a prostate orgasm to happen – DON’T TOUCH THE PENIS!
With porn and clothes on you’re waiting till you will feel that your prostate starts to ache and become engorged.
If you’ll be only sorta horny when you insert the prostate massager, it will probably won’t be worth it and won’t work.
During the process just enjoy and if you want you can work on relaxing your ass.
Relaxed ass will make massager insertion easier and it will cause the prostate to be more exposed.
When you contract, prostate moves out from a reach into your rectal wall.
To help with it I suggest to squeeze and tense the penis and ass as hard as you can for 10 seconds… Then relax.
Step #5 – Getting Inside: Reaching The P-spot
Now you should go back to the lube part, get the headphones and get to space you prepared.
Lube it up. Finger your ass. Lube the toy.
Watch this video to help with the prostate, but if you found your P-spot already, move on.
External Scrotum massage
I like to first start with an external massage around the asshole to relax it.
The first sphincter is voluntary. The second one will take some time to let you in.
Just massage around till it’s all nice and relaxed.
You can contract your butt muscles as you breathe in and relax as your exhale to help yourself to let go.
What are The Best Positions for Prostate Milking?
There is no one size fits all and you’ll need to experiment.
It depends on the toy you got (Pure Wand, or Hands-free like Revo or Hugo)
My favorite position is laying on the side as the lady in the picture and manipulating my hand from behind. It’s called a fetal position.
Other popular positions are:
- lay on all fours, doggy style.
- lay on your back, a missionary with legs spread wide apart (a sex pillow helps to expose butt)
- squat against the wall
- kneeling position
- lay on the bed and put legs up in the air against the wall (use pillow for back support)
Oh, and a great tip to avoid toy being pushed out is to wear loose underwear or use a belt.
Lower the belt from the back and put against the toy, so it has nowhere to go.
Yeah, You’ve got yourself a hands-free experience!
Step #6 – Techniques For Massaging P-spot and Stages of Arousal
You might wonder…
What do you do during those 2-3 hours?
You enjoy the sensations.
You listen to the audio.
You flex the kegels.
And let the toy do the work.
- If you use Nexus Revo Stealth, turn off the vibrations, just use the slowest rotating head setting. Change positions after several minutes to see which gives you better sensations. Do some light ass squeezes. Slowly build it up, increase sensations
- If you use nJoy Pure Wand, start with a small head, but try to upgrade to the big head as soon as you can. That’s where the real stuff happens. A great position is laying on your back, cupping the other end of the toy with your legs and moving it with leg movements. (hands-free). Or… go on the side and manipulate the wand with your hands…think 10-20% intensity… press lightly. Squeeze butt lightly.
Don’t just lay there expecting magic.
Everyone is different and you should experiment a lot till you find the right angle, pressure, and pace.
Here are a few more ideas (with Revo the position and movement are taken care of):
- press toy on top of the P-spot and pull it down in come hither motion
- try a firm and direct pressure like pressing the doorbell button and releasing
- move toy left to right like windshield vipers
- angle your butt differently to change the way P-spot is exposed
Notice your arousal slowly increase.
Focus on sensations in your body.
Continue breathing deeply and heavily.
Note: I really like playing real female orgasm compilations (NSFW – feel free to search on adult sites) and I copy the breathing, trembling, moaning girls do in the video. They know naturally how to do it, while guys have insecurities, mental blocks…that tense their body and don’t allow this expression. Practice this and you’ll feel more.
Take your time.
Even if you don’t notice mind-blowing orgasm approaching, don’t worry.
Remember: It’s about the journey and it will be enjoyable either way
If you’ll forget yourself in the journey, chances are the destination will arrive unexpectedly at the right time.
How do you know if you’re moving in the right direction?:
- Your penis will get hard without any stimulation. Transparent drops of pre-cum might come out.
- You’ll start noticing sudden PC muscle contractions.
- You’ll feel hot waves of energy building up around your genital area
- You’ll feel your legs and cheeks tingling, you’ll feel a little high.
You’ll notice sensations only increasing in strength and intensity if you’re moving the right direction.
You might even feel like peeing at some moment, which could mean you’re pressing too strong on P-spot.
If you keep all this time with deep, slow breathing while slowly increasing your arousal with a constant, slow P-spot massage, you’ll start feeling vibrations through the whole body!
If you don’t keep the pace and breath – you’ll feel the sensations ONLY surrounding your rectum, perineum and genital area.
Whatever happens… Roll with those feelings and keep going.
If you’ve seen women orgasming intensely, the whole body shaking – that’s where you’re going. Embrace it.
Don’t be afraid to moan and let your body shake – enjoy the intensity!
Note: Mr. Racy has published a nice infographic on stages of arousal, that may help you to understand how far are you developing (but note that your sensations still might differ)
Step #7 – The Final Stage: Achieving Prostate Orgasm
As the intensity increases, you’ll feel like something is coming. That energy simply must go somewhere.
As the orgasm approaches your ab muscles will start shaking, PC muscles will intensively flex and relax by themselves.
You’ll feel waves of energy going through the body. It will feel like an implosion happening inside that will not subside for 30-60 seconds.
But since it’s a dry orgasm, you can keep going for one more…and one more orgasm. Every next orgasm will come faster and will last longer.
If you’ve ever been jealous of multi-orgasmic woman, now you’re there too!
When you’re done, just lay with that pleasure, keep breathing and feel the waves calming down.
You’ll feel like after an energizing workout or sauna. Jelly legs. Bliss.
After the first orgasm, it will be very easy to chain these.
Just let your body do what it wants to do.
After a while, you’ll learn what feels good and start doing more of it.
Remember: Most guys achieved their first Super-O within a year!
And of course, whatever happens, don’t forget to finish off with a glorious cum shot and penile stimulation.
Those always feel good and you’ll be BLOWN-AWAY of the amounts of semen you’ll be shooting.
Prostate Play Troubleshooting Tips: It Didn’t Work?
First of all, look at it as a process.
If you at least enjoy it and have enhanced penile stimulation – you’re progressing very well.
Remember, you are rewiring years of conditioning from penile stimulation and discovering a whole new orgasm.
Give it time.
Few extra tips:
- Focus on what you’re feeling, not on what you’re not feeling.
- Learn to enjoy the sensations while not trying to speed up or force the process
- Think of it as a meditative experience, rather a jerk-off, release session
- There is no “best toy” – even if there are toys that give orgasms to others, everyone is different (and I believe njoy Pure Wand is the most fits-all-size-toy). Keep experimenting with different sizes, angles, materials.
- Slow down your breathing.
Again – give it time. As long as you feel like you are progressing – you’re doing great.
Suggestions To Have A Prostate Play With Your Partner
Before we finish, I just wanted to hint how easy it is to introduce prostate play with your partner.
From all the women I’ve talked to, including my girl – they are all excited about the idea of either seeing me doing prostate stimulation, doing it to me or try the pegging play with a strap on.
Of course, it helps if you give her orgasmic orgasms first… then she will be much more interested to give you a hand too 😉
If you as a guy are okay with it, your woman will be down for it for sure!
The easiest first step to introduce this is to offer her to watch you do this. Just let her be there and observe you.
Then as you progress you can let her do it while guiding her.
I really like that with njoy Pure Wand I first use it on her for nice G-spot stimulation… Then I clean it up and let her use it to my ass.
Vag to ass is safe (just don’t do it another way around) and that’s extremely kinky!
The Most Important Tip When Doing Prostate Milking With Partner
Make sure you stay off the penile stimulation.
There is not much use if prostate + jerk off is connected.
This will only reinforce the wrong associations with external (penile) stimulation.
Let her start with milking your prostate and then if it doesn’t cause orgasm, then you can move to a normal way and it will be insanely good.
Just don’t mix both IF you want to experience PROSTATE ORGASM.
Lastly, pegging is a fun thing to do together.
If you get a curved dildo (pegging dildos), it will hit the spot just right and she will be the one doing it 😉
This Lovehoney Strap-on harness kit with 7″ dildo is great to test out the waters and have fun with your wifey.
Nothing is as hot and vulnerable as her taking you in the ass.
To me, however, I’ve never managed to reach PO with my partner. I still find it tough to be truly free and relaxed when I have company.
But than again, I even prefer to have a drink by myself… So some will love and thrive in shared experience and some will find more success by themselves.
Taking It To The Next Level
There are lots of moving elements in reaching a Super-O and even if I tried to simplify it to the Three-Legged Stool Technique…
There are lots of tiny details.
I’ve made this little infographic for you that shows the prostate milking step milestones for easier measurement of your progress. (click right –> save as).
Please share your success or challenge stories below to inspire other guys!
And if you found this guide useful, share it with someone who might benefit from it… I would really appreciate it!
You rock — thank you!
Also…If you wanna share your story…ask questions…
Smash that comment form! I reply to every one of them!