Prostate Milking, Orgasm and Massage: The Guide to Chastity Prostate Play

Most men who take part in male chastity spend countless hours thinking about their poor pathetic cocks. Little do they know, they’re missing out on a whole world of fun by exploring anal play!

While many Mistresses will be perfectly comfortable probing their slaves depths, others never even think to try it. Solo chastity enthusiasts also often miss out on this hidden pleasure, lacking the confidence to start exploring their own body in new ways.

One particular kind of anal play that every man should try is prostate stimulation. This small gland is a source of hidden joy for men and often referred to as the P-spot. But what exactly is it? And how do we go about stimulating it?

Keep reading to learn everything you need to know about chastity prostate play!

What is the Prostate Gland?

As mentioned above, the prostate is a gland that can be stimulated anally. But what exactly is it?

In it’s normal bodily function, the prostate gland functions as a small valve between a man’s bladder and penis. Your prostate is essentially responsible for controlling what goes in and out of your cock. But there’s more to it than that.

When aroused, the gland begins to secrete prostatic fluid. This secretion becomes mixed with semen from the testicles during masturbation, and helps to protect the sperm as it enters the vagina.

For men who don’t regularly masturbate though, prostatic fluid can be a problem. As time goes on the prostate gland will build up with more and more prostatic fluid. Among other things, this can lead to prostatitis, a painful inflammation of the gland.

The prostate gland also helps regulate the release of hormones by the brain, especially those related to reproduction such as testosterone.

Where is the Prostate?

Unfortunately, it’s position makes accessing the prostate gland a little awkward. It essentially sits a few inches up the torso, right in the middle of the body. This makes anal probing the most effective way to reach it, and is commonly used by doctors needing to examine the prostate of their patients (which is a great roleplay idea for those of you into that).

Finding the Prostate Gland

Due to it’s unfortunate location, many Mistresses and slaves will often struggle to even find the prostate, let alone stimulate it. There are two main ways to find the prostate, internally and externally.

Internal prostate stimulation is exactly what you think it is, anal entry to reach the gland. When you’re still figuring out exactly where it is though, it’s best to start off with just a finger or two. It’s also much easier if you let someone else do it, which is ideal for those of you with a willing Mistress.

All you need to do is insert a finger, and feel along the inner walls of your anus. You’re looking for a small fleshy bulb around the size of a walnut. You should know when you find it, as pressing down on it will make you feel like you need to pee!

External prostate stimulation lets you explore without putting things inside your anus. This is perfect for slaves who have only recently begun to explore the pleasures of their body, Mistresses who aren’t comfortable with anal play, or simply those who don’t enjoy anal stimulation.

To find your prostate you will need to feel the perineum. This is the area of skin between the scrotum and the anus. Near the front of the perineum you’ll feel the penile bulb. It’ll feel harder and more firm, as this is the inner base of the penis.

Move slightly further back, and you’ll feel a softer, fleshier area. Here is where you need to press to stimulate the prostate. If you get it right, you’ll feel the familiar need to pee.

Why Stimulate Your Prostate?

Prostate stimulation can have numerous benefits. By touching, stroking, or whatever kind of touch you prefer, you can force the prostate to expel some of the built up fluid. This can help relieve any inflammation.

It’s not just a surgical process though. More importantly to many, many men, prostate stimulation can feel amazing. With enough practise, it can even provide orgasms which are more intense and body-shaking than a pathetic penile orgasm.

How to Stimulate the Prostate

Once you’ve located your prostate (or your slave's) and are confident in your ability to successfully stimulate it, you’ll probably be wondering what to do next. This is where the real fun begins. Every slave is different, and it’s up to you how much pleasure you want to give them.

Prostate Massage Techniques

The way you massage your prostate will make a difference to what it feels like for you. You can experiment with different methods of stroking such as small circles, come-hither motions, pressing it like a doorbell, or even tapping it to simulate the feelings of vibrations.

You can also experiment with many different sex toys to enhance and improve the experience. For a solo practitioner, a prostate massager is an ideal tool. These are specifically designed with a curve so they can apply as much, or as little pressure to the gland as you want. You can also try different butt plugs and anal beads to see which you enjoy the most.

For those of you lucky enough to have your own Mistress, the possibilities really start to grow. With them manipulating the toy, you can use almost anything you can think of! One favourite for many chaste men is a complete role reversal. Let your Mistress don a strapon, and enjoy the ride while she pounds your prostate into next week!

Prostate Massage Positions

Another way to experiment with what prostate stimulation has to offer is by trying out different positions. Whether you’re practising alone or with a Mistress will make different positions easier or more difficult.

While you can basically do this in whichever position you want, there are a few commonly chosen ones. These are:

  • Laying on your back with legs in the air: In this position, you can simply reach down between your legs to reach your anus. This can feel like a bit of a stretch on your own, but is an ideal position for your Mistress to stimulate your prostate.
  • Laying face down: As a solo stimulator, this will be one of the easier positions. You can simply rest your arm across your back while you use your finger to stimulate the gland.
  • Doggy Style: Undoubtedly one of the most popular positions for chastity enthusiasts who enjoy prostate play. Doggy style gives your Mistress ample entry with her fingers, toys, or even a strapon to peg you with.
  • Laying on your side (half foetal position): A half foetal position will often be much more comfortable when reaching between your own legs. Simply lie on your side, and pull one knee up to your chest. When you begin to tire, you can swap sides and raise the other leg instead.
  • Sitting: A sitting position is only really suitable when using a sex toy to stimulate your prostate. Rocking back and forth can push the toy onto the gland, applying more and less pressure at different times.

Prostate Milking and Prostate Orgasm

With the technicalities of actually reaching and stimulating your prostate out of the way, we can move onto the fun part. Both prostate milking and prostate orgasm are outcomes you may be looking to achieve during your prostate stimulation sessions. But each is different, and which you aim to achieve will depend on your goals (or those of your mistress).

Prostate milking is less about male pleasure, and more about draining the gland of the excess prostatic fluid. This fluid will gradually leak out of the penis, and is quite similar in color to milk - hence the name.

Prostate Orgasm is a completely different ball game, and it’s not something easily achieved by most men. Sometimes referred to as anal orgasm, a prostate orgasm is the pinnacle of male pleasure.

There are two important things about a prostate orgasm. One, is that it can be a full-body experience that a man cannot achieve through simple penile stimulation. These orgasms can be like waves of pleasure, emanating deep from the core of your body and washing over every extremity.

The second important thing about a prostate orgasm is that you can have one without triggering ejaculation. This is important because of the refractory period. When a man ejaculates his body enters a state of recovery, where he will be unable to have another orgasm for a short period of time. With a prostate orgasm this isn’t the case, so you can cum again and again.

Actually reaching prostate orgasm isn’t an easy process. Many men will need to practise prostate stimulation for months or even years before they can reach it. If this is your goal, you’ll need to be completely calm and comfortable with your own body, and commit to following the feelings and fully losing yourself in the process!

Adding Prostate Play to Your Chastity Lifestyle

How you incorporate prostate play into your chastity lifestyle is something that will be unique to your own situation. For those who practise chastity alone, it can be a big decision to make. Meanwhile, those who have already submitted to another will need to discuss it with them, and if necessary, gain permission to explore. Meanwhile Mistresses and Masters can think of all kinds of ways to make use of prostate play to tease and titillate their slaves.

When you begin to experiment, you should be open and honest about what you enjoy, and don’t. If you’re going to be able to reach orgasm through this kind of play, then that could undermine your efforts to remain chaste. Meanwhile you can make use of prostate play to heighten your arousal and explore a completely new kind of denial and torture.

How to “Spice Up” Your Prostate Milking Sessions

Here are some unique ideas which will make prostate milking even more fun for you – and even more torturous for him!

Ice, Ice, Baby

Make his release even less pleasurable by numbing his cock and balls so they will experience less sensation throughout the process. The easiest and most common way of doing this is by applying bags of crushed or cubed ice to his locked cock as you stimulate his prostate.

Slaps, Pinches and Pulls

Ball torture is a wonderful option, and one of our personal favorites over here at Lock the Cock. You can tug, twist or slap his testicles, or attach toys such as ball weights or ball stretchers to them. Add to the experience by verbally chastising him the entire time – “If your worthless balls didn’t produce milk in the first place, I wouldn’t have to take the time out of my day to do this to you!”

Drying Him Out

Once your caged man’s prostate has been thoroughly milked, it won’t be able to produce any semen for at least an hour – likely more. This offers you a unique opportunity to cause him an extreme amount of pleasure-pain through a tactic known as a dry orgasm.

A dry orgasm is essentially the exact opposite of a prostate milking. The cock undergoes muscle contractions, but no semen is released. While the brain does release some “pleasure hormones” such as oxytocin, the “spasming” of the penis while attempting to release semen has been described by many men as a tense, uncomfortable and thoroughly unsatisfying and frustrating feeling.

The possibilities really are limitless with prostate stimulation! Take the plunge today add a new dynamic to your own life in chastity!