Male Chastity Play - All About The Prostate Part 3: Spice Up Your Milking Sessions

More Fun With His Bum

How to “Spice Up” Your Prostate Milking Sessions

Once prostate milking has become a regular part of your chastity lifestyle, you may start looking for ways to make your milking sessions more interesting and pleasurable. We mean for you, of course – your chaste man, as we all know, would much rather have his pathetic cock continue to be locked up and his pleasure denied!

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.

This way, milking will truly be just about draining fluid out of him, and not about feeling good for him in any way. If you get him numb enough, he won’t even be able to feel the semen exiting his body!

Other potential methods of numbing his cock include: applying large amounts of various cooling lotions, making him take a long, ice cold shower or putting his cock cage in the refrigerator and then making him put it back on while still cold.

Slaps, Pinches and Pulls

In one of our previous articles, we mentioned that not all men are immediately able to reach release from prostate stimulation alone. If your man requires extra stimulation, there are plenty of ways to give it to him that will be less than pleasurable and will not grant his locked cock the tiniest bit of enjoyment from the process.

Ball torture is a wonderful options, 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!”

Don’t forget the non-traditional erogenous zones as well! We already mentioned the perineum, but you can also try giving his butt cheeks a nice spanking or dress him up in a shiny new pair of nipple clamps.

If you do decide to include his cock in the process in any way, make sure to keep him caged throughout. Focus on sensations which will mix discomfort and pleasure – try tickling, slapping or tugging rather than stroking. Touch only the less sensitive areas, such as the base. Avoid the head as it will likely cause him to have a full orgasm much too quickly.

A Little Extra For Good Measure

A successful milking will result in several small dribbles of semen rather than one or two large, powerful spurts. As a result, a good way to make the milking process even more clinical and less pleasurable than before is by measuring the volume of his release.

Position his locked cock in front of / over something such as a kitchen measuring cup or a medical flask. If neither of these are available, you can also use a medium-sized condom or even an empty soda or juice container. Order that he stay as still as possible even while releasing so that all of his semen will end up inside.

This seemingly small addition to your play in fact opens up a world of options. One, you can add some humiliation play by pointing out that his release volume has become smaller and smaller as his chastity lifestyle continues and his cock shrinks and shrivels up. Give him an extra reminder that the semen he produces is your property, not his, by forcing him to dispose of it – “waste” it by flushing it down the sink or toilet or “use” it by having him lick or drink it all up.

Measuring his release also allows you to set a limit or end point on the milking session. You can decide that he is done once he has released a certain amount, whether or not he feels like he is or not. It’s a perfect reminder that the power is always in your hands, and never in his!

Doctor, Doctor!

As men get older, they are usually required to undergo regular prostate examinations during their visits to the doctor or urologist. These examinations are a medical necessity which test for prostatitis, prostate cancer or other serious medical conditions.

However, they are also extremely clinical, arguably dehumanizing processes in which the man is forced to allow a virtual stranger – a casual acquaintance at most – to rummage around deep in their ass. Invoking this experience and its impersonal, detached nature is a perfect way to make his milking sessions even more humiliating than before!

Of course, this can be done by utilizing costumes and role play. Wear a white coat and blue or white disposable medical gloves. Have him in a paper or cloth medical gown or any garment which leaves his bottom totally bare. You can even take a visit to a costume shop or sex store to pick up props such as a stethoscope, a rectal thermometer, and more!

Establish the scenario and then make sure to stay in character throughout. From the minute you walk into the room, you are no longer lovers or even master and slave – you are the “doctor” and he is the “patient”. Refer to him as “Mr. [his last name]” and insist that he calls you “Doctor”. Ask him questions about his health and pretend to write down his answers on a clipboard. You can even take his temperature or measure his height, weight or blood pressure to make him really feel like he’s having a check-up!

During the milking itself, do not use any sexual language or standard dirty talk at all. Keep it clinical – talk about the size of his prostate, the volume of his release, and other similar topics. You can even combine your medical roleplay with measuring the amount “milked” from him as described above!

Of course, a doctor and patient scenario is far from the only sexy roleplay which you can carry out while he is locked up and being milked. From a prisoner being interrogated to a farmer and his prize cow, the possibilities are literally endless!

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.

We’re not going to lie – coaxing a dry orgasm out of your thoroughly milked man is not an easy task. Usually, it involves a mix of engaging various erogenous zones such as the prostate, testicles, nipples, or even the penis directly. It can often require some pretty intense stimulation to get his cock back in the game, especially if he is tightly caged. (You may find yourself needing to remove his cock cage for this type of play. If this is the case, remember to keep him from giving in and playing with himself. Bind his hands, arms and legs thoroughly and remind him just who he belongs to!)

However, in our opinion, the effort required to force him to experience a dry orgasm is more than worth it. Not only will the event itself be a mixture of pleasurable and painful for him, but it will leave him frustrated and arguably hornier than before. He will feel as though he is still “missing something” – the full orgasm that he was denied – and his body will likely quickly try to become aroused again. Of course, his sturdy cock cage will prevent that from happening!

A dry orgasm is also yet another great way to assert your control over your caged pet. Your control of his body is so great that it literally forces it past normal human limits, causing an orgasm-like reaction even after his cock has been completely drained of all its fluid. It reinforces to him that his orgasm is no longer something he can make even the slightest decision about – everything rests entirely in your hands.

Lastly, like many other things mentioned in this article, a dry orgasm provides yet another opportunity to get in some humiliation if that is something you or your caged partner enjoy. His masculinity is further sapped by being forced to orgasm without any “manly seed” coming out. You can, of course, verbally remind him of this fact throughout the process. For extra fun, add some slaps to his ass and call him your “bad boy” for being unable to orgasm properly!

Time to Play: Prostate Milking with Toys

Most couples participating in the chastity lifestyle enjoy milking sessions at least once every 4-6 weeks. Of course, a goddess doesn’t always have the time or inclination to milk her locked pet’s prostate using her delicate, gorgeous fingers. I mean, what if you just got a fresh new manicure? What if your caged man has been a bad boy and doesn’t deserve your touch on his tender flesh? Or what if you’re simply tired and just don’t feel like putting in that much effort for your slave today?

Luckily for all of us goddesses out there, there’s another option: toys. There are a number of toys out there on the market which can successfully stimulate his prostate and coax a dribbling, seeping release out of his cock.

We recommend checking out various sex toy shops or Web sites to decide what works best for you and your partner. Of course, you can always try out multiple different options – here at Lock the Cock, we believe that there’s no such thing as having too many sex toys in your playroom!

However, we’ll give you a quick rundown of the types of toys most commonly used in prostate stimulation. This will give you an idea of where to get started if you’re new to the milking experience!

Prostate massagers, sometimes also referred to as prostate dildos, tend to look similar to the more standard dildos intended for use in the vagina. However, they are often thinner, to account for the fact that the rectum often does not stretch as much or as readily as other parts of the body might. In addition, some of them may be curved to help them reach the prostate more easily. Most will also feature a wide or flared base which allows the mistress or keyholder to let go of the toy without any risk of it getting stuck.

As with vaginal dildos, there are many models of prostate massager which vibrate at various speeds and frequencies for extra pleasure. While these are a great option for spicing up your milking sessions, be careful to keep the vibrations on a lower, gentler setting to avoid giving him too much stimulation and accidentally causing a full orgasm!

Butt plugs tend to be shorter and wider than prostate massagers and will almost always feature a flared base. Not all butt plugs can successfully reach the prostate; however, many men find them extremely arousing as they can safely be left in for long periods of time and usually force the asshole to remain in a stretched position. Here’s another Lock the Cock pro tip – a great way to tease your caged man is to make him go about his normal day with a butt plug deep inside him. Why don’t you even try sending him off to work like that?

Butt plugs come in a wide range of styles, from metal to silicone and from brightly colored to ribbed, textured or even studded with sparkly jewels. Fetish-themed butt plugs, such as those featuring attached animal tails or hollow ones for liquid or sensation play, can also be easily found. We highly recommend experimenting with your partner and possibly even selecting several different butt plugs to use in your bedroom games!

Anal beads are a string of spherical “beads” connected by a string. They come in every size from tiny to impossibly large; some strings even contain beads of multiple different sizes. Anal beads are well-liked because their length usually allows them to reach sensitive areas of the rectum, such as the prostate, with ease. When using anal beads, it is important to remember that removing them from the asshole can cause as much pleasure as inserting them – go slow and steady if you don’t want him accidentally spurting before you’ve given him your permission!

Lastly, a particularly dominant Goddess may occasionally wish to bestow upon her caged slave a special, particularly personal and intimate type of contact. What on earth do you mean? you’re probably asking yourself right about now. Well of course, we’re talking about none other than milking his prostate with a strap-on, a type of dildo which can be worn by a female via a harness. That’s right, attach the strap on, get behind or above him and climb on! He’ll be dribbling his milky little fluid in no time with just a few powerful thrusts from your Goddess cock!

So What Are You Waiting For? Get Milking!

As you can see, prostate milking is an amazingly intimate experience which provides a number of benefits for both the keyholder and the caged partner. It keeps him healthy while giving his Dominant plenty of opportunities to show off their power and control in the relationship. Prostate milking may not be for everyone, but we definitely recommend that all of our lovely chastity couples out there give it a try!

For more fun with your toy’s sensitive ass, check out our anal play ideas page here and our ruined orgasm how-to guide here. Alternately, head over here if you’re interested in learning about how prostate milking can actually improve a man’s overall physical health. Lastly, check out our discussion of lube here to make sure you’ve got the perfect lubricant picked out for your next “date” with your caged partner’s prostate!