Discovering Multiple Prostate Orgasms


A man’s butt is a pretty personal thing. Many men don’t want anyone going anywhere near it! We sit on it, check it out in the fitting room mirror when we are trying on jeans, guard it and hope to get some compliments on it. But other than that, hands off!

This is particularly true in the US. We are really suspicious of anyone who gets too close to the ass.


Keep Your Hands Off MY Ass!


Discovering the JOY of Prostate Massage

One day I found myself wondering why I was hearing so much about “up the butt.” What was the big deal? I was jacking off in the shower, soaped up my fingers and started to play around my asshole. Using my thumb I just broadly rubbed across the anus. It felt pretty damn good. The orgasm was even better!

A few days later I found myself jacking off in the shower again. This time I curved my “fuck you” finger, went under my balls (past the taint) and played with my asshole again. This time I slid my soapy finger in a bit and wiggled. It was tight going in but quickly passed the tight sphincter ring. It was soft and warm inside. I didn’t have to go far before I found a knob—this was the Prostate (also known as the P-Spot). I later learned that this was the male equivalent of a woman’s G-Spot. (And we’ve all heard a lot about that!)

Now THIS felt even better! I exploded loads of cum all over the shower walls.


Ass Play is Easy in the Shower


When I was a kid—before puberty—I had learned to masturbate by rubbing my belly on the  bottom of the bath tub. (It wasn’t until years later that I learned that this is known as frottage.) I was so excited to learn that my body could create wave after wave of pleasure. What I didn’t realize was that I was having multiple orgasms. I would have this wave of pleasure (a dry orgasm) and could just keep on going until I had another one.

One day I reached this wonderful sensation but this time something different happened. White fluid erupted from the end of my penis! This had never happened before. Did I break something? I was sure that this was God’s curse on me for playing with myself. I knew this was too good to be true!

Sadly I also lost the ability to keep masturbating. Once I ejaculated I couldn’t even bear to touch my penis for a while. It was just too sensitive.

Flash forward to that day in the shower as I was standing there with my hard cock in hand and a finger up my ass. I had re-discovered that sensation of orgasm that I had lost at puberty. HAPPY DAY!


Just Add Water, Soap & a Few Fingers & You Will Have Great P-Spot Play


Like a kid in a candy store, I had found out a way to have the sensation of cumming multiple times while edging until the moment when I allowed myself the final release of jazzing. This was good stuff!


But Only Gay Guys Play with Their Butt, Right?

This may have been the case in our parents’ generations (oh, our poor fathers) but those hang ups are fast dying. Why would you deny yourself the pleasure of playing with your own prostate in your own home and enjoying multiple orgasms? This one is a no-brainer.


In Position with Butthole Spread Wide, Balls out of the Way with a Leather C Ring


The Male Multiple Orgasm:  Myth?

It is possible. When you have sex or jack off resulting in an orgasm (from penile stimulation) you ejaculate with your orgasm. The store is closed for a while after this because men have a refractory period. During this time it is physiologically impossible for us to have another orgasm. However, when you experience a prostate-driven orgasm there is no ejaculation (although there will be pre-cum) so you can just keep going as long as you can take it. Some men report having orgasms as fast as 10 seconds apart.


Where is the P-Spot? Just Follow Your Finger...


The Most Important Sexual Organ is the Brain

In other words, you have to be in the right head space. Most men can drop everything, drop trou and be ready to roll. I have to mentally prepare myself and relax. Sometimes I can play with my prostate for what seems like an eternity and nothing happens. It still feels good but nada.

There are other times when an orgasm will hit five minutes into it!


Create the Right Space

Creating the Right Space with Metal Worx Dildo & Titan .6 Cock Ring


Find space where you can moan and scream as loudly as you like. Create the right setting. If you are alone pretend you are setting the scene for a great seduction—only you are seducing yourself. This might mean dimming the lights and lighting candles. Maybe you take a nice warm shower beforehand. Get rid of the distractions. Shut the blinds. Silence your phone.

In this way it’s not like masturbation. Jacking off can be a quick pressure relief valve taking only 90 seconds OR it can be a wonderful edging session that lasts 90 minutes! Prostate massage is a bit more concentrated.

Think about it—your dick sticks out in front of you. It is conveniently located right between your arms at handy hand level! Just reach out and touch it, baby! Your prostate is a bit more covert. It’s tucked up your rectum behind the root of your cock. You have to go on a mission to find it. It also can result in putting yourself in some funny positions to get there! (This is one reason prostate toys are popular—they give you a little more flexibility in hitting the spot!)


One Finger or Two? Just Insert and Gently Move to Unlock Your P-Spot



Give Yourself Time

Don’t just expect to slam a multiple orgasm in between appointments. Give yourself some time to set the mood, get into it and find your orgasmic rhythm. Plan on at least an hour to gently probe your ass and explore what feels good. The sensations will roll over you—enjoy them. Don’t put pressure on yourself to experience orgasm your first time out.

As you get rolling you may find that your self-date will last a couple of hours. In this time you might experience 25 orgasms. With experience you may find that you can reach this peak more quickly but at first you won’t. Don’t be hard on yourself.

Once the first orgasm hits the rest will just start to roll. Go with the flow. You may experience non-stop orgasms for a bit and then experience a bit of a dry spell. Don’t worry; both are pleasurable.


Don’t Touch Your Cock!

Resist the temptation to touch your dick! You will want to! It will be jerking around, quivering with emotion, feeling neglected and steadily weeping pre-cum from your piss slit. But RESIST TEMPTATION! The longer you can hold off holding your prick the more intense your non-ejaculatory orgasms will be. In this way it is a lot like edging. When you do finally allow yourself to touch your hot rod and give a stroke or two the orgasm with ejaculate will be an explosion like you have never experienced before! Trust me, you will really be weak in the knees.


What Do I Put Up My Ass?

Fingers (Yours or a Partner’s)

 When You Start Out a Finger or Two Will Do...


As you start your journey towards prostate orgasms start it solo. Take the time to discover what feels good and what does not. As you gain self-knowledge you can bring your partner along. It’s a great way to spice up your sex life and discover something new and pleasing to each other.

Most men cannot reach a multiple orgasm state by just using their fingers. However, once the orgasms are rolling, fingers will keep things moving well. To be successful you will likely need to get things going by using a toy (more on that below).

When using fingers, you can start in the shower (like I did) by spreading your legs, leaning slightly forward and reaching between your legs. You can use the other hand to brace yourself against the shower wall.

Once out of the shower, you can lie on your side with your bottom leg extended straight out and your top leg bent so the knees comes into your chest. This opens up your rectum nicely. Twist slightly and reach from behind. Insert your thumb or fingers (I like starting with my thumb to warm things up and then move to my longest finger—for better reach). You may find that your arm gets cramped in this position. But then you can switch sides or try another position.


Find a Position that is Comfortable for You--& Switch it Up


Another option is to stand, squat or kneel in a position similar to the one I described for the shower. Reach under your balls and past your perineum to your butthole and insert a finger. You won’t have to go far—perhaps to the second joint. Once your finger (or fingers) is in bend it so it is pointing towards you’re the base of your dick. You will know you have hit the right spot because it is a bit softer than the surrounding territory. Using a ‘come here’ motion with your finger, massage the P-Spot. Alternate your motion by pressing on it or rubbing slightly past it. (For those of you who have massaged a woman’s G-Spot, the technique is surprisingly similar.)

It’s not a bad idea to change your position. If frequency or intensity of your prostate orgasms decline, switch positions. Try lying on your back with your knees up (as though you are sitting on a chair) or knees pulled to your chest (this really spreads your asshole nicely). If you get tired, you can be in this position with your feet against a wall. Lie on your stomach with your ass lifted by a pillow. Or position yourself on all fours (doggy-style). All of these will work—your “job” is to find which works best for you!



A Dildo with a Bit of Flex Can Really Hit the Spot


Toys are a great enhancement—and they give you more to work with. I’m often asked which is the best anal toy on the market. I have found that it really depends on your personal physiology. What works for me may not work well for you. I personally enjoy the angles of the Optimale or Pleasure Probe.



The Pleasure Probe & How it Hits Your P-Spot


They are easy to manipulate and are shaped well for me. Find what is comfortable for you. There are many different shapes, materials, girths and flexibility out there. Toys give you the ability to extend your reach while maintaining full control over the motions you are using. You may find that you achieve orgasm more quickly when you massage the prostate gently, moving in a circular motion, applying a bit of pressure or more actively stroking it. On the negative side, you can get tired (think of it as an extension of your cardio workout!) The solid stainless steel anal toys are fun and sexy but they do get heavy! In addition, when you hit an orgasm you will be so overwhelmed you will forget to keep moving your toy! That leads us to vibrating toys.


Vibrating Toys

One of the best ways to get started is with a vibrating toy. The beauty of these babies is that you slide it in and then don’t have to worry about continuing to manipulate it. It just keeps going (but keep spare batteries handy)!

Sliding your vibrating toys in and just relax. (You should relax before you put it in as well by the way!) Be in the moment and recognize the sensations that you are feeling inside you. Don’t worry about the orgasms right now. Flex your pelvic floor (kegels; clench your ass) a few times to change where the toy is putting pressure. Feel the warm sensations emanating throughout your body. Continue to flex as this continues to move the vibrations around. In this way you are massaging your prostate just by flexing your kegels. Experiment.

Then spend a bit of time just doing nothing. Enjoy the moment.

One of the many benefits of a vibrating toy is that when an orgasm starts to build and especially when an orgasm hits you won’t have the energy or presence of mind to do anything. The toy just keeps on doing its thing! This makes your orgasms even stronger. The intensity can become overwhelming! This is especially true if you experience consecutive orgasms. Before you can even catch your breath you will be into the next orgasm.


Or Perhaps You Crave a Really BIG Toy (Save that for Later)
(His Medical-Grade SurgeBLACK C Ring Keeps His Package Up & Forward)



Lube is our friend. You can’t use too much. It is really important that you use a lot to make entry easy. I love MD Science’s Anal Lube with Cloves.This stuff really relaxes me and makes entry pain-free.

Anal Lube with Cloves


Getting Ready

One of the reasons we are so protective of our butts is our waste leaves the body there. It’s a fact of life (and without it life would totally suck). However, for most of us there is no bigger turnoff than finding a bit of leftover turd during play. If you feel the urge, hit the bathroom and get rid of that waste. You can also take a quick enema to really clean things out. I like to pop in the shower and pay special attention to my asshole. Not only does this clean things up but it starts the juices flowing!

I already addressed your head space, but many guys will go an extra step by having an alcoholic drink or medicinal weed (of course, only where it’s legal!) This can really help you to relax.


Inaugural Session

Keep your expectations realistic. I have never met anyone who had an orgasm the first time out of (or into) the chute. Invest the time and it will pay huge dividends! At the end of your first session when you finally do reach out and touch your writhing cock, your ejaculatory orgasm will blow your mind! You will also be amazed at how much pre-cum you have and then by how huge your load will be.

Continue to focus on the sensations. What feels good? Don’t worry about whether or not you will have an orgasm let alone multiple orgasms!

Even when you don’t have multiple orgasms, you will continue to improve and your ejaculatory orgasm will be more powerful and pleasurable.


Your First Prostate Orgasm

It won’t happen on your first try (unless you are extra-special!) However, when it does happen it will be easier to keep having them since your body now has experienced it and knows what to do to recreate it. We are very clever at replicating what gives us pleasure! You will be overwhelmed with the intensity of this orgasm—so much so that you won’t even realize what hit you until after it’s over! Of course, your focus will be on the sheer pleasure and the part of your brain that analyzes experiences will be completely over-ridden. You won’t be able to process it because it is so overwhelming. Just enjoy!


Maintain It

After that first prostate orgasm, just relax and keep doing what you are doing. The orgasms will just keep coming and coming. ENJOY!


Ending Your Session

You won’t want to stop but at some point you will become exhausted. You can continue to build the sexual tension by just stopping—no ejaculatory release. This is harsh, cruel and takes tremendous discipline. But the next time you touch yourself be prepared for a wild ride as that pent up tension yearns for release.

Most men will opt for masturbation to end things up. You can pound out a down and dirty wad or milk it for a while. You may want to continue to ride the crest of sexual pleasure by edging—if you can! Whatever you choose to do your ejaculatory orgasm will be incredibly intense! Be prepared to shoot far with loads and loads of cum. The quantity will be mind-staggering.

Are you ready for amazing multiple orgasms? It’s all in your hands!

gear essentials…Sex is Better here! ENJOY!








Kitty: love that your man loves anal play cums like a bunny! We’d like to know more—how did he start with anal play? Do you help? Let us know : ) Thanks for your comment! Jay



Dirk! Congrats on your multiple orgasms! That is amazing! I can totally understand having to be carried to the bed to recover! What was different than before to cause the orgasms? Whatever it was, KEEP IT UP!



I thought my partner was the only guy who could come like a bunny with anal play! Fabulous blog!

Dirk Beach-Barrow

Dirk Beach-Barrow

I have been into Fisting since 2003, and rarely had an Anal Orgasm. For various reasons, I had taken a 3 year sabatical from Fisting, and in May began the journey back. Several weeks ago, I was enjoying a three way with my husband and a new FFriend. I was in the sling and FFriend was working my hole and going full hand for the second time when it happened – the first of NINE IN A ROW ANAL ORGASMS !! When the last one had passed, it took both my FFriend and my husband to lift me out of the sling and carry me to the bed where I stayed for an hour “recovering”. It was better than the night I lost my FFisting Cherry!!

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