Male Chastity Devices

Ruined Orgasm And Prostate Milking

Ruined orgasms and prostate stimulation are arguably important practices within chastity relationships, especially when concerning long term orgasm denials. I am a fan of the ruined orgasm, and I simply love doing it to playmates and subs. It’s always unclear as to how many people will conduct, or experience a ruined orgasm, but if it’s something you’re curious about – then be sure to read on. This is a guide to giving ruined orgasms and prostate stimulation – a very good way to empty a boys plumbing during chastity training to ensure that fluid doesn’t have a chance to build up.

Sexual Frustration Is Part Of Tease And Denial In Chastity

What Is A Ruined Orgasm?

Ruined orgasms may incorporate specific elements of teasing and denial it must be noted that the two are not the same. Teasing and denial refers to the art of edging a male sub. The sub might be continuously brought to the edge of orgasm, and once he has reached that edge all forms of stimulation will stop. Resulting in him sitting there, twitching horny as hell. Once the stimulation stops, he will generally receive a break either a complete break or be forced to provide stimulation to his partner, before he is again brought to the edge and stopped. This might happen throughout the session over an hour or so and even longer. However, in tease and denial, he does not experience an orgasm. Period. He might be locked back into the cage and denied the ability to orgasm leading him incredibly sexually frustrated and howling for more. Ruined orgasms take this principle a step further in the sense that semen will be released without a proper orgasm. A release might be in the form of a single drop of semen, or a series of failed and ruined orgasms that will over the course of the session completely drain the sub.

It’s important for the dominant to be paying attention. The critical aspect of any of the techniques that we will demonstrate to you, is that the stimulation must be stopped the second that the sub begins to have contractions. Contractions are easiest to monitor with a restrained sub laying on his back and with his penis just hanging there. How does this work? Well, the ejaculation from the body is not responsible for the contractions. Orgasms will occur as a result of stimulation to the penis during the period that the contractions are occurring before, and during ejaculation.


Before we get to the discussion of the techniques used to administer ruined orgasms – let’s make it clear that we are on the same page. Newbies, beginners or people that aren’t necessarily paying attention will often provide stimulation to the sub male until the first shot of orgasm is ejected from the body. Once this first shot is seen it is then that they will stop all forms of stimulation. This is an example of a partially ruined orgasm as opposed to a ruined orgasm. As we explained slightly earlier, an orgasm begins before the semen is released. If you’re in the position of jerking off a sub or yourself, up to the point where the semen is being ejaculated then you’re most likely gone too far. Your sub, or yourself, will experience some pleasure, but it won’t be completely ruined.

Males will often talk about the point of no return. This is the moment when jerking off or masturbating a male where any point of additional stimulation will end up in the contractions and the releasing of semen. If you continue any form of stimulation beyond this point of no return, then he will experience pleasure through orgasmic sensations. The trick, and it’s a very delicate one, is to stop the stimulation during the small window after the point of no return, but before ejaculation and orgasm begin. Completely ruined orgasms take training, practice, and an understanding of your victim’s body.

Now with that out of the way – we will cover some of the more popular methods to use.


This is one of the more common types of ruined orgasms and probably the one most seen in gay bondage films. It’s remarkably simple and easy to accomplish as well, probably why it’s one of the more popular methods. All you really have to do is slowly stroke him until the point of no return. Then let go, walk away, and leave him to his contractions. Most of the time when using this method, you’ll find that not all of the ejaculate will be released from the body unless you decide to give him a few more strokes. However, be warned, that every additional stroke, touch or sensation applied after this method can result in a partial orgasm.

If it is done correctly, what you’ll find is that the semen will squirt, dribble or ooze out without the orgasm. This is arguably the best method for frustrating your male partner and playing with long teasing and denial sessions. For example, if you’ve spent the last few hours edging him close and then backing off until you finally decide to finish. In these situations the sub will not know if he’s going to have the pleasure of coming or not. When he sees and feels you going all the way to the end, he is going to be expecting a mind blowing orgasm from all the teasing and denial throughout the session. Reality hits hard when he realises that all he’s getting is a ruined orgasm. Not only will he be exposed to the mind numbing reality of such an orgasm failure, but he’ll be left feeling stunned and defeated – not to mention still incredibly horny. This is the perfect kind of training that you might use to explain to your sub that he is to never underestimate your ability to surprise him. An unexpected ruined orgasm delivered in this fashion will leave his mind wondering if he’ll ever experience real orgasms again.


This is a favourite among some circles, but time consuming, requires patience and an understanding of your sub. In a way it’s remarkably similar to the abandonment method, however this will often result in a few drops of semen being released at a time. I will say again, this type of technique takes an incredible amount of practice, patience and understanding. You need to be fully aware of your subs reactions, and looking for the different signs that indicate when he is approaching that pivotal point of no return.

This technique takes a lot of practice and understanding of the different signs for when your sub is approaching the point of no return. One of the tricks that I like to use is to slowly ease back on the stimulation as he gets closer to an orgasm. You might switched from using an entire hand, to using a soft finger to coax him to the edge again. Using that one finger you can provide the stimulation necessary to draw out a tiny spot of semen, watching as the penis bobs up and down from the contractions as you cease all forms of stimulation until the contractions stop. You can then test it out with a finger, and if the contractions begin again remove it. Else, you can then slowly reapply our entire hand and begin the process again. This is a time consuming method but it is incredibly and utterly intense. Any sub that I have performed it on tells me that they haven’t experienced anything like it before.

After the contractions of subside, the sub can be stimulated again until he is brought over to the edge. This technique is repeated over and over until there’s really nothing left. You could conclude the session by stroking him to completion – which will result in a very dry, unsettling and unsatisfying experience. Males that I have done this to will describe is as a burning sensation that has no enjoyment or pleasure within it. Once you have done this form of stimulation – the male will then have no choice but to wait until the supply is replenished for a proper orgasm. It’s a very fun type of draining method that is best suited to chastity and chastity devices. Because he hasn’t technically orgasmed, there’s no release of the hormones that are normally associated with orgasms, meaning that he will still be in the same behavioural state as before the stimulation.


Sexual Frustration Is Part Of Tease And Denial In Chastity

For this method of ruining orgasms a foreign object such as a penis plug or a sound might be used to block the urethra and prevent the escape of orgasm. This can result in a painful retrograde ejaculation. Alternatively, failing a foreign object the thumb placed over the urethra can work quite well. For males that have experimented, or used penis sounding devices, they will most likely be very familiar with this kind of sensation. You can also have the ability to stroke and stimulate the penis as per normal when using this method.

As he tries to ejaculate, the semen and fluid is then recycled back into the body through the urethra, which can allow the process to be repeated if needed. There are some health concerns with this technique and there are risks to the body if it is done too often – so consider this your warning. Blocking the urethra with your thumb can be difficult – during ejaculation the penis will contract and semen can shoot out with a surprising amount of pressure. To keep it in, you’ll need to provide a tight seal. If you’re going to be looking at using your fingers then you’ll find  that the thumb is going to work best for keeping a firm grip on the head. If you’d rather use a foreign object – you could use penis plugs and the sort though you will both need to become accustomed to using them to avoid any mishaps. Never use anything that is not meant to be inserted such a cotton bud or Q-Tip – these can be quite dangerous and not at all pleasant.


If you like cock and ball torture then you’re going to be head over feet with this method. It’s pretty much exactly the same as the abandoned ruined orgasm except with one slight change. The second that you stop the stimulation, you will slap hard on the frenulum. If it has been timed correctly – then what you’ll witness is a very slow dribble of semen coming out of the shaft.

If you enjoy CBT with ruined orgasms, you’ll like this one. It’s basically an abandoned ruined orgasm with one small catch. Immediately after stimulation is stopped, the frenulum on the underside of the head is slapped hard. If timed correctly, this will cause semen to dribble out. For this one it really is best if the sub has been restrained and tied down – otherwise he might just be able to twist his erection around just as you’re about to whack it.


If you’re a sadomasochist and your partner doesn’t enjoy pain – then this one is especially cruel and painful. If the squeezing of the genitals is done hard enough, then most of the semen will be prevented from escaping during ‘ejaculation’. For men that love pain, spanking the balls might be enough to induce an orgasm so keep that in mind. Some dominants might even combine the stroking with the spanking and/or squeezing of the genitals to create a wonderful mix of pain through CBT and pleasure with the orgasm. Truly devious.

If you really want a kick from the ruined orgasm, then give him the satisfaction of stroking him to completion and then springing it on him unexpectedly. The look on his face is absolutely priceless, but remember to have him tied down.


This one is another CBT variant of a ruined orgasm, but isn’t as pain intensive as some of the other ones mentioned. This one involves a firm squeezing of the shaft after the point of no return. Whilst some semen will still be ejaculated, it certainly will not be in a forceful manner. This method will pretty much destroy all orgasmic pleasure and create a very unique and odd sensation. Please note that the same health risks apply to this method as it does with cock plugging.

It might also take a little bit of practice. As you need to find the point where you’re squeezing hard enough to prevent the propulsion of semen, yet not as hard as to cause any damage. This is one that is particularly enjoyed by the dominant, as they will be able to feel the power of the contractions and the pressure of the semen hitting the block which can allow for an extremely empowering experience.


After you’ve been teasing a denying a guy for an extended period of time – testicular stimulation might just be enough to send him over the edge. A strong and powerful vibrator such as the Big Boss, or a Hitachi wand would be perfectly suited to the task. For the best results possible, it might be beneficial to have the balls tied or pulled down with a ball stretcher so that they’re away from the body and pressed firmly together. This will be useful in ensuring that they receiving plenty of vibrating stimulation. Testicular stimulation can also be applied in this method whilst wearing a chastity cage as well. The frame of the chastity device will be able to provide vibrations down the entirety of the shaft, stimulating it to a very frustrating orgasm. The best part about this technique is that he doesn’t even need to have the chastity device removed!

Some people might find that the Hitachi wand is far too powerful. There’s two options here, opt for a slightly less powerful variant, or purchase a dimmer switch and then attach that to the device. This means that you can actively control the power on the device and find the perfect setting that precisely fits the needs that you are after. Dimmer switches are remarkably cheap and easy to use. Definitely pick one up no matter how you’re planning to use a Hitachi Magic Wand.


Aneros Prostate Massager For Prostate Milking And Ruined Orgasms

Anyone that is familiar with long term chastity will also be familiar with prostate milking. Prostate milking is the final technique to ruined orgasms that we will explored.  Prostate milking involves the simple manipulation and stimulation of the prostate until semen is released. Prostate massagers can actually produce some of the most intense orgasms that a man can experience – however that’s not the purpose of this article. What we will be exploring is the prominence of ruined orgasms.

While prostate massagers can be good for beginners, fingers are probably the best method to use for beginners. The reason is simple, with your fingers you will be able to actively feel what you are stimulating and you will actually find it a lot easier. Using a prostate toy to find his g-spot  means that you’re not going to have any sensation of what is actually being touched. Everyone has their preferences though, so at the end of the day it’s probably best to experiment between the different ways and work out which suits you best. Stimulating him in the doggy style position will provide the easiest access to the prostate.

For the majority of men, you will find that the prostate is located a finger length inside the anus. When you find it, the male should feel a slightly buzzing sensation – you’ll definitely know that you’re in the right area if he tells you that he needs to be. If he says this, you’ll need to massage more gently because the bladder is located right next to the prostate and you’re probably rubbing too firmly and pushing the prostate into the bladder.

For those that are providing penile stimulation as well as prostate stimulation – then you’ll find that the prostate will harden at some stage. This is important to take note off. If you can feel it hardening then you need to stop all penile stimulation at once. The prostate is the gland responsible for contracting and the releasing of the semen, if the prostate is hard then the release is usually imminent.