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Want Penis Free Pleasure? Try Prostate Stimulation


While caged, many men will search for alternative forms of pleasure that don’t need an erection. Some examples include nipple play, erotic hypnosis, or even something simple like holding a vibrator against the outside of the cage.


But every man has a hidden pleasure source which is perfectly accessible even when wearing a chastity device: the prostate gland.


This small area can provide a massive amount of pleasure, once you learn how to stimulate it.


Never Heard of the Prostate Gland? Here’s the Basics…

Like the penis, the prostate gland is a body part only found in men. It’s small, roughly walnut shaped, and located just below the bladder, roughly in the middle of the pelvic area.


The prostate gland serves a simple function. When you pee, and when you ejaculate, the liquids all come out of the same tubes. The prostate functions as a simple switch, allowing your body to swap between “pee mode” and “ejaculation mode”.


Older men are much more likely to be familiar with the gland, as it’s recommended that you get it checked regularly after age 40 for signs of cancer. Prostate cancer is one of the most common forms of cancer in men.


But it’s not all doom and gloom. The prostate gland is also capable of producing large amounts of pleasure, which is why some men (especially those wearing cock cages) learn to stimulate this gland.



Achieving Prostate Pleasure – How to Stimulate Your Prostate Gland

Stimulating the prostate gland is mostly a simple process. There are three distinct ways you can do it.


1 – Perineal Stimulation

Between the penis and anus is a small area of skin called the perineum. By placing pressure on this area and gently massaging it, some of the stimulation will also reach the prostate gland.


It can be difficult at first to really feel anything, because there’s no clear place you should be massaging. But when you find the right spot, many men feel like they need to pee.


Perineal stimulation of the prostate feels good, but very few men will be able to reach a full blown orgasm with this method. Most often, it’s simply a nice addition to other kinds of sexual play like masturbation or blowjobs.


2 – Anal Stimulation

Most commonly, men will turn to “directly” stimulating the prostate via their anus. While we might refer to this as “direct stimulation”, you won’t actually be touching the gland but the anterior (front) wall of the rectum. By pressing on this wall, you’ll be able to provide strong pressure to the gland itself.


Some of you are probably already shuddering, and that’s fine. Some men just aren’t into anal play, and there’s nothing wrong with that. But pushing through those feelings and trying it can lead to some of the most intense pleasure you can feel.


Actually doing it is very simple:

  • Lubricate your anus and chosen finger.
  • Slowly and gently insert the finger into your anus.
  • Once inside, curl your fingers in a “come hither” motion until you find the right spot (you’ll know when you hit it).
  • Massage that spot.

That’s it!


Hitting the right spot with only your fingers does require a little flexibility, and can prove challenging. Luckily there are plenty of prostate massage toys you can use instead, which are designed with a slight curve that should nestle snugly against the gland.


3 – Urethral Prostate Massage

The final method of prostate stimulation is one that few men will ever dare try: deep urethral sounding.


Sounding is the process of inserting various metal rods into the urethra to feel stimulation from the inside of the penis. Some urethral chastity devices will include short plugs that go inside the urethra, but these will not be long enough to reach the prostate.


Once a urethral sound is inserted deep enough, you’ll be able to directly stimulate the prostate. This is a risky kind of play though, so we don’t recommend it unless you really know what you’re doing, and have done lots of research on sounding.


Three Cock Cages

Why Does Prostate Play Feel Good?

With the “hows” out of the way, let’s talk about the “whys”.


Stimulating the prostate is pleasurable. At it’s simplest form, you could wear a prostate massager during sex, and when you reach orgasm the experience will be much more intense than normal.


But we’re a chastity site, so most of you won’t have access to your penis, and will be using the prostate as the only source of pleasure. Sometimes it’s what a Mistress has told you to do, sometimes it’s something you’ve chosen yourself.


Either way, prostate stimulation is often described in a very similar way to G-spot stimulation in women. By continuing to massage the area, the feelings can become more and more intense. You may even start “leaking” fluid from your penis, called prostatic fluid.


Some Mistresses will deliberately massage their slave’s prostate to produce this fluid, in a practise known as prostate milking. In this context, it isn’t done for pleasure but instead as a more “clinical” procedure to reduce the slave’s desire for orgasm.


For the very lucky (or very dedicated) men who are able to fully relax and enjoy the sensations, they may be able to reach a full prostate orgasm, a type of orgasm that needs no penile stimulation.


What’s a Prostate Orgasm Like?

A regular penile orgasm is usually a very intense, building sensation focused entirely in the genital area. This is followed by an “explosion” of pleasure as the pressure releases and the orgasm happens.


Prostate orgasms are very different, often described as pleasure building in the core of your body. As the pleasure grows, it begins to “wash over” the rest of your body in waves, providing a full body experience similar to the way women can feel orgasms.


It can take a lot longer to reach this peak than it does during penile stimulation, and some men are never able to fully relax and experience the orgasm part. You may also find that if you do reach the orgasm, you don’t ejaculate as you normally would (which also means no refractory period, so you could have multiple orgasms this way).


Curious? Try Prostate Massage Yourself

The descriptions of the feelings and sensations all probably seem a bit vague (and we wish we could be more specific), but the experience of massaging your prostate is something really difficult to put into words.


So, our best recommendation would be simply to try it yourself. You might just unlock a whole new world of pleasure.

Michael Cole Author Profile Picture

Michael Cole

Michael is the author of the Total Chastity Diary and has been in and out of chastity since his mid-thirties. He’s now 41. He lives and works in Boston, has a white-collar job, and is single by choice. 

“There’s nothing hugely special about me. I’d describe myself as your typical modern, forward-thinking guy. I enjoy sports, staying healthy, love my family and friends, and have a satisfying career that pushes me to work hard so I can enjoy some of life's luxuries. 

I’m whatever constitutes as “normal.” It just so happens that I also enjoy the feeling of putting my cock in a cage, leaving it there for a week or two, then reaping the benefits of being released from my cage. 

Starting my chastity journey felt like starting any other new hobby or interest. I wanted to make sure I was doing it right and had good equipment to help me achieve the results I wanted. But when I began looking into male chastity and cock cages, what I found was a lot of fetish talk. 

While I accept this is what male chastity means for some - dressing up as a sissy, being spanked by a Dominant and whatever - the kinky kicks aren’t what I’m into. 

My hope with the Total Chastity  Diary is to bring a more matter-of-fact voice to chastity experiences.”

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