Connect with us

Different male milking techniques for more control


Different male milking techniques for more control

With male chastity becoming ever more popular either as a lifestyle or occasional kink, prostate milking of males is also ever-increasingly referred to, discussed and probably practised. Often in chastity circles, people just talk about milking the prostate without considering how to carry out the procedure to gain the desired effect. If you’re currently milking your chaste male, the chances are that he’s probably getting a lot more pleasure from milking than you think.I’ll leave the debate about whether it is actually necessary to milk a chaste male to other forums and concentrate instead on how you can increase and decrease the amount of pleasure he will experience from it. After all, even if it is not necessary to drain the prostate regularly, the procedure still gives benefits to both the male and his keyholder.

If you aren’t familiar with the basic technique and principles of prostate milking, do a quick Google Search now and read one of the many available guides to acquaint yourself with the male anatomy involved and safety precautions. I have written this guide from personal experience to give keyholders, an insight into how it’s possible to vary the pleasure levels from a shakingly earth-shattering orgasm which will probably be the most intense he will experience, to a hugely frustrating anti-climax without any orgasmic contractions and almost no pleasure at all for the male in question. I guess the latter is the kind that keyholders will be most interested in and of course my apologies to those poor men who are currently enjoying their milkings and are about to submit to an even greater depth of control by their keyholders. It is actually quite an art to give a pleasureless milking which is why I’m fairly sure that the chances are that your male is currently enjoying an orgasm every time you milk him.

First off, it’s almost impossible to milk a man’s prostate without him getting *some* pleasure from the pressure on the prostate. Particularly cruel mistresses advocate the use of an ice pack or chilli to reduce/remove this pleasure. I haven’t experienced either so I can’t comment.  However, when my prostate is being gently massaged, I can feel sensations right to the end of my penis, it’s a delicious feeling but is somehow an empty pleasure which only feels truly satisfying when it’s accompanied by stimulation of the head of the penis and/or testicles. The beauty of prostate milking is that even though it’s a pleasurable feeling for the male who is being milked, if done carefully you can leave it just as an empty pleasure which leaves the male wanting more but unable to get satisfaction because he hasn’t got any prostate fluid left and therefore is unable to orgasm.

I’ll give you a guide on three main different types of milking experience:

  1. Maximum Pleasure
  2. Ruined Orgasm Milking
  3. Minimum Pleasure

The lines between each are of course blurred so infinite variation is possible once you know what you’re doing.

I’m writing this from personal experience—I’m regularly milked for pleasure and tease/denial by my partner and through trial and error (and with my help!) she has learnt a lot of the subtleties to be able to vary my pleasure levels according to her whim. I love it. Please bear in mind that these are my own observations and there might be some variation between different males but the principles are probably true for all. The biggest variation I suspect will be between those who have been circumcised and those (like me) who have not.

There are two main objects you can use to milk a man—either your fingers or with a purpose-built prostate massager like the Aneros. If you’re looking to follow the instructions below, I’d advise you to purchase some Nitrile gloves and lube and use one or two fingers so that you can feel what the stimulation is doing to your subject’s prostate and surrounding area. You will feel things begin to contract the closer he gets to orgasm. Once you have learnt the signs and no longer have to rely on internal feel, you can then probably use a prostate massager to get the same effect.

There are also two main ways that you can position your man: on his back, or in a kneeling position. The key thing is that you make sure that you are in complete control of his penis—you don’t want it to be able to touch anything because if you control the amount of stimulation here, you control his pleasure levels. Some kind of restraint to hold the arms and hands well out of the way is also probably a good idea, I can heartily recommend a pair of leather mitts from Top to Bottom Leathers: very comfortable and highly effective. Generally, my partner and I prefer the kneeling position with my legs apart and a stack of four pillows supporting my chest. My arms are fastened behind me and I’m usually blindfolded, occasionally gagged. She can then sit between my legs and has full access to all the parts of me that she needs. This works best because with me in this position, she is in total control and also if she decides to give me a pleasureless milking without any contractions, the fluids simply drain out by gravity and be caught if desired.
The final thing to bear in mind in this introduction is that apparently some males can be milked without any stimulation of the penis/testicles. This is great if you want to milk a chaste male without removing his chastity device. From my personal experience, I know that I cannot be milked like this and need at least some stimulation, either to the penis or testicles or a set of clover clamps to the nipples also does the job, but beware—the clamps can give enough stimulation for an orgasm so use them with care. Lastly, not all stimulation to the penis is equally pleasurable, if you want to expel pre-cum during the procedure (or just want to tease him) then gripping the penis at the base and sliding your hand upwards (even over the glans) will almost certainly not result in an orgasm or even very much increased pleasure. However, moving your hand in the opposite direction most certainly will!

1. Maximum Pleasure: How to Give Your Man an Earth-Shattering Orgasm.

Put on a Nitrile glove and lube thoroughly. Insert one or two fingers from your dominant hand and begin to gently massage the prostate and surrounding area. Ask your man what feels best. The one thing that your male will be wanting more than ANYTHING else in the world while you’re stimulating his prostate is for you to hold his penis and gently pull his foreskin up and down over the glans. Alternate between a few seconds of this and also stimulating his scrotum and testicles. There are many ways of giving him pleasure by touching his ball sack—my favourite is when my partner fans out her fingers and gently scratches the backs of her fingernails up and down it. A firm massaging of the testicles, combined with gentle tugging and squeezing also feels very good. Play with different levels of teasing and intensity while continuing slow-ish rhythmical stimulation of the prostate. Nipple clamps are an optional extra, too. After a while, you’ll feel as the prostate and surrounding area begin to get harder and contract.  As the contractions of orgasm begin (or just before once you’ve learnt the signs!) keep massaging gently and concentrate your other hand on his penis—a vigorous up and down movement will give him maximum pleasure. Continue stimulation until contractions cease and withdraw your finger(s). Don’t be surprised if he doesn’t last too long. I can manage only a few minutes of this type of stimulation (usually less than 5, depending on how I’m teased and stimulated). You can finish prostate stimulation as soon as orgasmic contractions subside. Contrary to common belief, milking does not produce any more fluid than any other type of orgasm, but I’m willing to bet that the description above will be the nicest way for your man to produce it!

2. How to Give a Ruined Orgasm Milking.

Follow the instructions above, to massage the prostate and stimulate the penis/scrotum/testicles. It’s probably best to restrain your male’s arms/hands so that you can be sure you have full control. What you want to do is stimulate up to the point or orgasm with as much teasing as you like and make him think that he’s about to have an orgasm like the one described above. However, as soon as you sense that he’s about to orgasm (believe me, you’ll know after you’ve done it a few times!) remove all stimulation except the gentle massaging of the prostate. He will ejaculate with orgasmic contractions but it will be a very unsatisfying orgasm. Remember from above—as he is about to ejaculate, the thing he wants most in the world is stimulation to the head of the penis so make sure that nothing is touching it and that he is unable to wriggle into a position where he can hump something—the desire for stimulation is very strong at the moment of orgasm!  If you want to expel as much fluid as possible, after the contractions have finished, grasp the base of the penis and slide your hand up towards the glans to force it out.

3. Minimum Pleasure: How to Milk a Male and Give as Little Pleasure as Possible.

This is the most difficult technique to master but can have a strong psychological effect on your male. If you ensure that your male doesn’t experience any orgasmic contractions at the end of milking then he’ll receive almost no pleasure from the procedure. When I’m being milked, the ‘hollow pleasure’ of prostate stimulation is almost psychologically like a promise of a lot more pleasure to come (if you’ll pardon the pun!), it is utterly delicious in an orgasm denial scenario to be denied any pleasure but to have my prostate drained anyway, thus preventing any chance or orgasm in the next while (probably about 6 hours minimum for me).

Follow the instructions above but keep the stimulation of penis/scrotum/testicles to a minimum (or avoid this completely if your male is able to be milked with no extra stimulation—trial and error will tell you). If you need to give some stimulation, then see if you can avoid touching the penis and instead concentrate in massaging/squeezing/tugging the testicles. Another very good tease is to grip his penis behind the glans and gently pull back, to simulate the feeling of it being pushed in during intercourse—a small amount of this is probably adequate, and be careful because it is almost definitely enough to cause an orgasm if you do it at the critical moment.

Keep the gentle rhythmic massaging going and look out for the point where you can feel the prostate and surrounding area contracting.  At this point, reduce the massaging and prepare to stop just at the point where orgasmic contractions are about to start.  In my experience there are two stages of contraction in the male orgasm—the prostate goes hard and contracts to initiate ejaculation and then the pleasurable orgasmic contractions (perhaps six or seven of them) follow. What you’re aiming to do is keep stimulation going up to the point that the initial (less pleasurable) prostate contraction is about to start, then cease prostate stimulation for a few seconds (5 or so) and then restart gentle milking to clear the fluids out of the prostate but all the time keeping stimulation below the threshold for orgasmic contractions. It’s tricky to do the first time but if you pause milking before orgasm begins you should be OK.

Depending on the male and how much extra stimulation you give him, this procedure will take anything between 10 and 40 minutes. If it’s taking a while then verbal reassurance that this is OK will probably put your man’s mind at ease, he may have been worrying that he’s not performing and find it a massive turn on that you’re spending this time to milk him in such a subtle and devilish way.

I hope that you find the above information of use and that your relationship benefits from it.  If you were to ask me which of the three techniques feels best, that would be a very difficult question to answer. Obviously the first feels intensely pleasurable, however the relationship between pleasure and frustration is a very complicated one for a chastity enthusiast.  Each scenario is very pleasurable, you either get a huge orgasm or indefinite frustration which is of course what the chaste male really craves.  I personally recieve a ruined orgasm milking most often, which I both love and hate, and very, very rarely receive the full-on orgasm. The third technique is particularly cruel, especially after a long period of tease and denial (both in terms of the single session and an extended time period), but it is probably the scenario that I crave the most, and that’s the mysterious paradox that is male chastity!

This article has been republished with permission from John.  Please visit his website to view the original post and more related articles.

Feature image courtesy of Shutterstock
Have an amazing experience or tips you like to share on SimplySxy?
Drop us an email at!

I'm a 35 year old cycle mechanic, living in London England, with my female life partner, we've been together 7 years but known each other for nearly 20. We enjoy kink and enjoy switching sub/dom roles depending on how we feel. We have been playing with male orgasm denial on and off for about 4 years and have found that it enhances our love life immensely.


More in Kink

To Top