Prostate Milking: The Ultimate Guide to Prostate Orgasms
So you’ve done your research. You’ve found your prostate gland. You’ve learned how to massage it properly and what sort of feeling you might have. The problem is, you just can’t seem to bring yourself to orgasm.
Don’t panic! You aren’t broken or incompetent. Prostate orgasms are quite difficult to have. Some men massage and milk their prostates for years without ever having an orgasm. While it would be nice as an end goal, you have to remember that you’re still doing something that is great for your health, even if you aren’t having orgasms.
If you’re determined to go to the next level though, good for you! It can take some dedication to actually reach the big O, but most men who have experienced prostate orgasm find that after you’ve done it once, it becomes a lot easier. This is because on your subsequent attempts, you know exactly what you did before, so it’s easier to replicate.
Just to make sure you’ve got the process completely down, I’m going to run through the entire experience, start to finish. Along the way I’ll also try to add in notes from across the internet. These might not be necessary for some people, but for others they can make the difference between a simple prostate massage, and a mind blowing orgasm.
The first phase of your prostate massage, is arguably the most important if you wish to achieve orgasm. Going into it with the wrong mindset is pretty much a guarantee that you won’t make it to orgasm.
Some men like to follow a specific ritual or guideline while preparing for their session. This is most often just the order you do things in, but can involve things like long baths, lighting scented candles and maybe even massaging themselves with some relaxing oils before they start.
There are a few common things that all men should do before they start a session of prostate play though. A bowel movement is going to be needed to make sure that you don’t start poking at any stored up feces.
Different men will say different things, but the average seems to be a trip to the toilet around an hour before you begin.
The next step all men tend to take is taking a shower. You want to pay extra attention to your anus and make sure it is sparkling clean. Depending on your experience with anal activity, you might also want to begin gently inserting your finger into your anus.
Not only will this make sure the immediate area inside is clean, but you can start to get yourself a little turned on with some gentle massaging of the area.
Whether or not you choose to get yourself started off while showering, nearly all men who’ve had a prostate orgasm will agree that being aroused is step number one in reaching orgasm.
When you get in the mood, blood flow to the area increases and the prostate begins to swell up. This makes it easier to find, but also much more pleasurable.
Almost anyone who has tried a prostate massage while not aroused will probably tell you the same thing: it doesn’t feel too great. So do whatever you need to get the love juices flowing, be it porn, stroking, massage, or anything else.
TOOLS FOR PROSTATE MASSAGE
Fingers are the go to tool for many men wanting to stimulate their prostate. They’re definitely the easiest option, but not without their own drawbacks.
The prostate gland is located around two to four inches inside the anus. For most men this will mean they need to insert their finger around two joints inside to reach their prostate.
For some men it can be further up, so more of a finger is needed. In others, their fingers just aren’t long enough, so they stand no chance of stimulating their prostate using fingers alone.
To know whether or not you can reach far enough, a good technique is to start by putting your finger just inside your anus.
Place a small amount of pressure on the front wall of the anus (the side towards your belly). If you don’t feel anything, then insert the finger a little further, and try a small amount of pressure again.
You keep moving up and pressuring until you find your prostate. You should be able to tell when you do, as you should feel a sudden urge to urinate. This is totally normal and fine, and you aren’t at risk of wetting yourself.
If you are able to find it and reach it effectively, great! You’ve made it past the first hurdle. If not, head on down to the prostate massagers section and see what other options are available to you.
The second hurdle when using the fingers to massage your own prostate is that they’re fingers. Stick with me here. When you use any part of your body for an extended period of time, what is the feeling you end up with? Tiredness. The same is true for your fingers.
In some men it can take several hours to reach a successful prostate orgasm, so using your fingers for that length of time can be quite difficult. Even if you can maintain some level of controlled movement for an extended period without hand or arm aches/cramps, you are also contending with a rather limited range of movement.
Keeping your finger in, and staying comfortable gives you a small amount of space to work with, and depending on the angle you need to use to reach your prostate, it might not be feasible to effectively massage the area.
This whole to-do with finding your prostate can be a bit of a turn off sometimes, so it may be worth spending some time on a seperate day exploring the area and identifying the right places to touch.
On another day, armed with your new knowledge get yourself prepared and aroused and start your session proper.
Again this is individual to each man, and if you find something that works for you then you’re all set to get started properly. If not, then it’s time to try some extra tools.
Where something cannot be done, man will find a way. This is never truer than with prostate massage.
Even in an area that has been surrounded by taboo and controversy over the years, those that were keen to explore have been able to find their own methods for stimulating their prostate where their fingers have failed. These methods take the form of prostate massagers.
Essentially a butt plug, but with a curve or angle, prostate massagers are specifically designed tools aimed at aiding you hit the orgasm you want.
They come in all kinds of shapes and styles, so you might need to spend a bit of time finding exactly what you’re looking for, but when you do they can make the entire process a whole lot easier.
If you choose to use a prostate massager over your fingers, you have a few added bonuses. The first is just a whole range of extra movement. You can hold onto the plug by the base, and angle it any way you want.
You have almost complete control over the movements and pressure you put on the prostate and it’s so much easier. Any time you feel your arms beginning to tire or ache, you can take a break and let them rest.
But even then you can continue stimulating your prostate with some simple Kegel exercises.
The clenching and releasing actions of an effective Kegel will move the plug up and down your prostate in a stroking action.
Your other bonus is vibration! A completely different feeling that no matter how dexterous you are, you won’t be able to truly recreate with your fingers. A vibrating plug can really change what you experience while prostate massaging, allowing you to fully let go and relax into the feelings without needing to touch anything.
If you’ve tried various things but found yourself unable to truly relax and focus on your feeling, a vibrating prostate massager can be the way to go.
I know we’ve talked a lot about getting started with a prostate massage session, and not talked much about actually reaching orgasm, but we’re nearly done with prep work. I promise!
The final area of prep to cover is lube. I maybe shouldn’t have left it till last, as it is undoubtedly the most important part.
Your butt doesn’t produce any lubrication! Without lube, any attempts at prostate massage will feel like rubbing your insides along sandpaper. To put it another way, unpleasant and painful.
Both silicone-based lubes and oil-based lubes are much longer lasting than water-based lubes. While the latter is totally acceptable for anal play, you will have to reapply it more often during a longer session.
Silicone-based lubes should be approached with caution, as using them on a silicone toy can break down the surface material, and contaminate your anus and rectum.
Oil-based lubes are the clear favorite here, and there are many kinds to choose from. I’ll leave it up to you, but be sure to do your research and know exactly what the lube you’re going to use contains. You don’t want any nasty surprises.
Due to the length of time you may need to be inside yourself, having a high quality lube is key. The longer it lasts the better! While you can reapply it as you go along, if you end up getting yourself close to orgasm and find that you need to stop and apply more lube, it’s really going to kill the mood.
You’re also going to need lots of it. Whatever you think is enough, double it. You need to make sure it gets everywhere, so really baste yourself in it.
The most important part is to get it up and inside your anus. This part is where a lot of people will fall short with anal play. Just because it’s on a finger, prostate massager, dildo, butt plug, or anything else, it doesn’t mean it’s automatically going to make it into your butt.
If you find yourself having trouble with this, look into picking up a lube syringe. These are usually made to medical grade standards, and inserting the tip into your anus allows you to directly feed the lube into it.
STAGE ONE: FINDING YOUR GROOVE
So if you’re nice and turned on, have everything lubed up, and chosen your method of massage, then it’s time to begin.
If it’s your very first time, you’re going to want to take it very slowly. While this is always good advice for any anal activity, it is especially true if you aren’t used to it.
The sphincter muscles of the anus are extremely elastic, but if you’ve never used them for anything other than toilet trips they aren’t going to be used to opening up at other times.
The more you perform prostate massage the more these muscles will adapt and eventually you should be able to slide things in with very little feeling of discomfort.
Once you’ve got your implement in, stop and have a little rest.
Remember you need to try and stay as relaxed and aroused as possible, and constantly thinking things like “my butt feels weird” isn’t going to help. You need to adjust, and get used to the feelings. It might not happen in your first session, but before long you’ll be totally used to it.
If you’re at the point where something is in your butt, and it doesn’t feel totally alien and weird. AND you’ve managed to keep your arousal and relaxation high, then you’re probably in the best state possible for a prostate orgasm. Now it’s the simple matter of stimulating it.
There are literally tons of different motions and movements you can try. Everyone likes different things, so rather than trying to tell you which one is “best” or “most effective”, I'll try to just list all of the ones I’ve come across and you can try them until you find your favorites.
- Come-hither motion: One of the most popular techniques, you gently roll your finger up and back in the direction of your belly. It’s exactly the same motion you’d use to tell someone to walk towards you, and is often recommended for a woman’s vagina for the exact same reasons: It gently stimulates the entire length of the area.
- Pushing a doorbell: This one is often recommended for entering your anus too. Rather than directly prodding or poking at anything, simply rest the pad part of your finger on the prostate, just like you would a doorbell. Then gently start to “ring the bell”. You can experiment with different amounts of pressure, and holding it down for different amounts of time until you find something that you like.
- Circling the yard: This one can be more difficult depending on your angle and how dexterous you are. Basically you want to lay the pad of your finger on the prostate, just like the doorbell, but this time rather than pushing, you run your finger all the way around the edge of the gland. Depending on the size of yours this may be more or less effective as you’ll have more or less surface to cover. You can experiment with speeds, and try different amounts of pressure while you rub.
- Simulated Vibrations: If you can get the hang of the movements without being too rough, it’s totally feasible that you can make your finger feel a bit like it’s a vibrator. While this can feel great and give you lots of stimulation, it’s going to be difficult to keep it going for a long period of time. It can be best to save this until you feel yourself getting close to an orgasm.
- Experiment! There’s probably loads more things that I haven’t mentioned and men will be thinking “why didn’t he say to do this”. Like much of this process, it’s a totally personal thing, so don’t be afraid to move your finger around and see if you can find something new that you enjoy.
- Be Gentle: No matter which techniques you choose to use while your finger is inside you, you need to be careful. The prostate and the anus are both incredibly sensitive areas, and going a bit too rough on them can leave you a bit sore for a few days. Roughing it up too often could cause some real damage to either, which isn’t going to help our arousal and enjoyment.
WITH A PROSTATE MASSAGER:
The options here are a little different, so I’m not going to make a list giving you techniques. Instead I’ll just give you some ideas of what kinds of things you can do with a massager.
- Pressure: is probably the easiest thing to vary with a massager when compared to fingers. Being able to move the unit around by pulling and pushing on the base can give you a much greater level of control. When you find a level of pressure you like or want to stick with for a while, you can try and position the massager to stay there, so it isn’t a constant effort like it is with your fingers.
Depth: Prostate massagers come in many different sizes. Some of the longer ones are able to go deeper into your butt while still hitting the spots of the prostate you need it to.
Others will literally just reach the prostate and go no further. Depending on how comfortable you are, and the enjoyment you get from anal play, you can try out different kinds of massagers until you find the one that’s ideal for you.
- External massage: Many prostate massagers will come with an extra arm that sits outside of the body. This isn’t just to keep it from getting eaten by your butt, but it’s meant to sit on, and stimulate the perineum. This fleshy area behind your scrotum is directly underneath your prostate, and is what people stimulate when they perform external prostate massage. By using a massager with one of these arms, you’re getting the best of both worlds.
Cock Ring: There are also varieties of prostate massager that come with a cock ring built onto the outside. These can be great if you struggle to maintain arousal during a prostate massage.
Some men have the unfortunate problem that the second something enters their anus their erections will instantly drop. Maintaining a solid erection throughout can do wonders for keeping yourself aroused.
- Vibrations: as we discussed a little earlier, can make the entire process of prostate massage that little bit easier. If you’re after something simple and easy to use, this is definitely the way to go.
If you’re thinking about going with a prostate massager over your finger, we’ve done an in depth look at both the designs and use of them which you should definitely take a look at.
STAGE TWO: PRE-CUM/MILKING
At some point during the process, you might notice some white fluid leaking out of your penis. You shouldn't be alarmed, as this is part of the prostate massage and is totally normal. What you’ll be noticing is basically ejaculation, only without the sperm.
The fluid is mostly made up of the liquids that are stored and produced in the prostate, and should be roughly milk-like in color and consistency, hence the term prostate milking.
You can choose to milk the prostate for as long as you like, and by varying speed or pressure you can spend a lot of time to make sure that everything is cleared out properly. If your main goal is prostate orgasm though, this won’t be your primary concern. It is though, a sign that you are on the right track.
Sometimes you might spend quite a long time massaging, but have no pre-cum leakage at all. It’s likely in this case that you just aren’t hitting quite the right spot.
Everyone’s body is different, and just because you’ve read it should be done one way it doesn’t mean it’s going to work for you. If this happens to you it might be worth trying something different.
TECHNIQUES THAT MIGHT HELP
There are a great range of positions you can use if your first choice isn’t working for you. The most popular and simple one will be simply lying on your back, reaching down past your stomach. If this isn’t doing it for you, or if you just fancy different, here are some options:
Face Down: Not the most adventurous change of position, but still an effective one. Flipping over to your stomach can help you have a bit more access to your anus, and you can rest your arms on your back while you massage so they don’t get as tired.
One downside to this one is that your hand will be the opposite way up, so things like the come-hither motion will no longer work. If you’re dexterous though, you should still be able to effectively reach your prostate.
- Both Legs Up: Still remaining on your back, but the simple act of pulling both of your legs up to your chest (or further if you’re flexible), can give you much greater access to your anus. The position also naturally opens up your butt cheeks too, making it a little easier to access.
- Laying on one side, outer leg to chest: This one’s a little harder to explain, but it’s kind of a fetal position on the outer half of your body. You use your arm to reach around over the bent leg to reach the anus. This can be quite a comfortable position, but the angles can make some kinds of stimulation a little difficult.
- Doggy Style: Just like the sexual position, doggy style can be a useful one for reaching the prostate. This position gives you some flexibility, as your arm can reach between your legs or over your butt to reach the anus. It can help to use some pillows to take some of the weight off your legs.
- Experiment! There’s no wrong answers here, so if you can find a position that works for you, then go with it!
SWITCH TO EXTERNAL
Most people are going to recommend using internal massage techniques when you are trying to achieve a prostate orgasm. If you aren’t yet comfortable with something entering your anus though, you aren’t completely out of luck.
While externally stimulated prostate orgasms aren’t as common, some men have perfected the art, and can summon some truly magical feelings without even touching their insides.
Even if you’re perfectly happy entering your anus, external massage can have it’s role in your prostate massage sessions. It can be a useful warm-up during your initial phases of arousal and prep.
Or you can use it as a little halfway break if your arm or anal muscles start to feel a little tired. So don’t be afraid to mix it up, and try a little external massage on your journey to prostate heaven!
USE THE PENIS TOO
All men will know what penis orgasms are like. Pretty much any penile touches while slightly aroused will really help get you going. As we discussed earlier, maintaining your arousal during your session can be a big help due to the increased prostate size, so making sure you’re nice and hard can make a big difference.
Another option is to wear a cock ring. For most men this will be enough to maintain a constant erection, with the bonus that you don’t need to touch your penis at all during your massage.
If you feel the arousal leaving, and the enjoyment dropping during your massages, a short play with your penis can help top you back up and keep you going.
You should be careful though, as for most men reaching a regular penile orgasm will put a swift end to any enjoyment you were receiving from your prostate massages.
GETTING SOMEONE TO HELP
Your quest for prostate orgasms doesn’t have to be a solo one! While most men will prefer their first few attempts at prostate massage to be done privately, allowing someone else to get involved can enhance the experience a huge amount.
Not only will it be easier for them to reach your prostate without you having to fold yourself up, letting someone else take care of the actual massage means that you can relax fully. Being able to focus entirely on the feelings you have rather than the physical act of performing massage, can make it easier to reach orgasm.
TALK TO THE DOC
While most men are able to find their own prostates, for some it might feel like you just aren’t hitting the right spot. This is probably more relevant if you’ve tried massaging a lot, but still not had any pre-cum during the stimulation.
It is possible that your prostate is just in a slightly different position to normal, so a conversation with a doctor (and maybe a short rectal exam) will help to clear things up. An added bonus is that if they do need to touch your prostate themselves, you’ll know exactly what it’ll feel like for your next attempt.
STAGE THREE: REACHING CLIMAX
Now let’s assume that everything is going great. You’re able to find your prostate and enjoy stimulating it. You’ve got pre-cum dripping out of your penis. But you just can’t reach orgasm. What’s a man to do?
Unfortunately, there really isn’t an easy answer for this. Some men will reach the goal quickly, others might take many attempts. The main thing is to focus on enjoying the process. Kind of annoying really, isn’t it?
Luckily for you I’ve scoured the internet, and I’ve found a couple of last tidbits of wisdom that just might help.
- Edging is the act of masturbating with the penis until you are just on the brink of orgasm, and then stopping. Sometimes doing this just before you begin prostate massage, and repeating any time you lose arousal can help bring you closer to prostate orgasm.
An intense need to urinate is often a feeling that will cause some men to slow down or stop their massage. For most though, pushing through this feeling and continuing with the massage is the final barrier.
So next time you feel like you’re going to wet yourself, remember that you definitely wont, and keep pushing yourself that little bit further.
- Utilizing your pelvic floor muscles at the right time can make the difference for some. The pelvic floor works with the prostate during orgasm, causing the spasming you feel in your penis and pelvis. If you can time some pelvic floor clenches as you near the peaks of your massage, it could tip you over the edge.
Now that really was a bit of an epic. I’ve spent a lot of time reading about many men’s different experience and tried to give you as many tools as possible for your journey to prostate orgasm.
The rest is up to you! Get yourself into the habit of regularly massaging your prostate, find the things you like, and hopefully before long you’ll be feeling the best orgasms of your life!