My Favourite Ways to Make Him Cum in Chastity

While many think that being locked in a chastity cage means that you’re not able to or allowed to cum, I say to you, my friend - no! I love to make slave D cum and shocking no one, he loves it too. Orgasms are fucking fantastic!

Here’s the catch; if I’m going to give him permission to ejaculate, he’s going to do it while he’s still locked in his cage. Not always, but it’s generally the way I allow it to happen.

You might be asking yourself, Mistress K, is this even possible? How can someone have a release without whacking their meat? Without a powerful erection? Even worse, with their erection suppressed in a little metal cage?

Trust me, it’s very possible.

Now, disclaimer time. Will this work with everyone? I haven’t Done The Science on this through conducting a survey, analysing the data or querying every locked cocks that we have access to (what a strange image, but let’s continue).

But never mind the science, news flash just in: orgasms are healthy! A message to all of the keyholders or dominants out there - milking your locked sub and/or partner regularly can help to reduce their risk of developing prostate cancer.

Let us not have any misunderstandings, I am all for plenty of tease and denial play, but there are many reasons why it’s worth finding a balance between denial and release. This works for us and I hope that if you’ve clicked on this blog post that it’s something that’s perked your interest that maybe it might work for you too.

Magic Wand / Vibrator

One of my favourite “tools” in our toy box. Why? Because my pleasure comes first! I make him use it on me (if he’s very good) and then we stop to cuff his wrists to a suspension point above his head.

I particularly like to lock slave D in a metal chastity device and hold the head of the wand or tip of the vibrator against the head of his cage. Materials like silicone will absorb the vibrations which defuses the intensity.

I don’t want that as it’s not the point of using a vibrator. I want him to really feel them. That’s why a metal cage is the better option for this although pressing a wand against the openings in our Hera to gently touch the skin just under the head is also pretty delicious.

Not to turn this into softcore porn, but this is where the tease and denial side comes out. I start slow, the pulsing sensation helping to build some momentum before I gradually increase the speed and intensity. Within a few minutes he’s often a begging mess and, if the stars are aligned or it’s been a while, I’ll let him finish. If not, I reduce the speed and slowly build him up again until I decide we’re done.

Vibrating cock ring

This isn’t my favourite but when applied correctly, can be a wonderful way to build up the tension in Slave D. If I know that I’m in the mood to use one then I’ll usually put the vibrating cock ring on him before a play session.

We have one that can be turned on by pressing a button on the side of it so I like to put it on whilst he’s wearing a cage. I find it quite easy to use even with his cage locked in place, though I’m aware that remote control versions are available to buy. Let me know in the comments if you’ve tried one and if you’d recommend it!

This method usually takes much longer than the wand or vibrator. The speed and power aren’t anywhere near enough unless he’s been edged sufficiently before we begin and that’s not always what I want.

Sometimes it can be on for too long and just ends up being overstimulating, or sometimes it can be frustrating because it’s Not Enough but depending on the mood I’m in, that can be exactly what works really well.

Cock sleeve

Usually made of silicone, these have changed so much since we first tried using them - to little success! These wonderful cock extenders are fun to use regardless of whether Slave D is or isn’t in his cage.

The flexible material means we can use it with a cage but depending on the type of device, you have to be mindful about catching it on hinges or locks which can damage the material. We’re out here promoting sustainability in our sex toys!

The cage you choose is a factor in this as some are too big or have an irregular shape that make it more difficult to put the sleeve over it or they won’t have enough exposed skin so it’s mostly just a visual tease.

He wears the strap-on

I know, shocking after writing a whole guide to pegging that I would suggest someone else wears the strap! But hear me out.

A sleeve goes over his cage, the harness sits against it. I’ve found that putting a harness on him during play is much easier than rolling a sleeve onto his cage and means there’s not as much faffing. If you’re in the heat of an epic play session and don’t want to lose momentum, sleeves can be a risky endeavour.

Strapping a harness onto him also gives me more options. You can put whatever size dildo you have into the o-ring of the harness as long as they’re compatible. Flat chastity cages work best with a strap-on as it allows it to sit closer to the body and against the cage, so it just feels more intimate.

You can also lean into a fun humiliation moment with this by getting him to grind or fuck a pillow or a pocket pussy instead of allowing him to touch you.

E-Stim / Electroplay

This is a relatively new addition to our play sessions, but we’ve been loving it so far. We bought an e-stim kit that comes with 2 conductive rubber loops. You can put the loops around their shaft, head and/or testicles or some variation of that. Try it, you won’t regret it.Game changer, folks.

Imagine this. You’re tied up, senses deprived with a hood and music via headphones and left to be edged by the slow pulsing coming from the e-stim loops fixed firmly around your caged cock. Not knowing how or when the rhythm or the intensity will build.

Could you handle it? How long would you last? 10mins? Half an hour? Well, time feels differently when your other senses are taken away. Slave D and I have managed over an hour of edging playing with the E-Stim. After deciding the moment was now, I very slowly increased the power and sensation settings until he came.

Seeing how his body reacted in that moment was something I won’t forget in a hurry. It was majestic and we’ve repeated it a number of times since, and tried different patterns and combinations. Can recommend, Mistress K Seal of Approval - GIVEN.

Suck his cage

It’s time to get a little more intimate. We are an actual factual couple, after all. Sometimes, Slave D is stressed after a hard week of packing orders and sorting out stock, so he gets a little reward with a blow job. Caged, of course.

If you decide to do this, you know the things that might get your submissive/your partner off - fondling their balls, pulling them away from the body (a delightful thing especially if they haven’t cum in a good while), gentle touches with the finger tips.

There are so many ways to either stretch it out or to make things move hard and faster and dirty if that’s what you're in the mood for. If they’ve been denied an orgasm for a while they can be right on the edge, so bear that in mind - a hair trigger response is the last thing you need in this situation.

Also, pro-tip! I like to put a condom over the end of the cage to make up clean-up a bit easier.

Cagejob

More vigorous than sucking on his caged cock and a very successful method from my experience. Slave D says that the physical motion of the cage moving back and forth in my hand is a great way to simulate as if he was allowed to touch himself. Fat chance.

You can lube up your hand, get a nice firm grip on his cage and work your hand rhythmically to get them excited. This is where silicone cages work really well for doing this - I’ve tried doing the same thing with cages made from other materials but it doesn’t work nearly as well both for him and for me.

Anal stimulation - Fingers or toys

Massaging their prostate is a sure-fire way to make them cum, even if they’re caged.

A milking toy like the aneros psy is what I’ve used on slave D many times and it works great. It took a little time to get the technique right and his feedback along the way - and sometimes it can feel great but not good enough to just push them over the edge. Don’t be afraid to experiment in a more casual play session and get their feedback in real time so that when it comes to the main event you’re well prepared. Eventually I did get it right and he’s been benefiting ever since.

Caged fuck

Your choice of cage here is essential! I cannot emphasise this enough. Something like our S216 is cock shaped, so it makes penetration a little easier. A well lubed and fitting silicone cage feels quite nice and acts as a second skin as well.

Be careful to check the cage for sharp edges that could cause internal injuries and also the design of the cage because if there is a barrel lock and that catches on some tender and delicate skin? Bad times for everyone involved. To be polite, it doesn’t feel particularly good if it slams against their pubic region or anus.

This isn’t my particular favourite because my anxiety for being caught doesn’t allow me to fully relax during it but we know some folks who absolutely love doing this.

Pegging

Easily my favourite method. I love it so much that I wrote a complete guide to pegging like I mentioned earlier which includes everything you’ll need to know. We had a lot of fun writing that - especially talking about footwear (if you know, you know.)

If you didn’t already know that men and people assigned male at birth are born with prostates. This is a marvellous little gland and by massaging or stimulating it….well I’m genuinely thrilled to be the bearer of good news. Yes, you can absolutely get someone off doing that and my word, seeing the aftermath of an anal orgasm is a delight.

So how do we do that as a kinky couple? Orgasm denial games, baby! These are games whereby if he follows my rules, then he’ll eventually be handsomely compensated. In order to earn an orgasm it shouldn’t surprise you to know that he has to earn it. He performs a pre-arranged list of tasks, some spontaneous ones that I come up with and by meticulously following my instructions during our play sessions.

I am benevolent enough to allow him to select his form of release and pretty much all the time, pegging is what he chooses. We’ve talked more about our feelings about it in the guide above (subtle nudge!), but it’s genuinely one of our favourite things to do together.

Vibrating butt plug

You can use a button press or wireless remote controlled butt plug depending on the amount of control you want over the toy. Some have one power level while others have lots of different vibration settings. Slave D responds well to pulsing and gradually building vibrations.

One challenge that we’ve had is keeping it in if he’s not wearing something like his Carmen Liu thong. It’s quite easy to have his cage exposed and the thong holding the plug in place. Hearing a plug bounce off the floor while I’m fucking his face with my strap-on is a disruption that can kill the vibe, literally.

Impact play

I have a confession to make here. I’ve never made slave D cum in his cage through spanking, flogging, using my crop or whip on his ass. I’ve tried a few times and it’s never happened. I don’t quit easily and I’m still confident that, in the right setting and situation, it will happen.

What has worked is using my crop on his balls. I don’t hit him hard as particularly if he has been caged for a long period of time, he is hugely sensitive. Instead I use light, repetitive taps. The key word here is repetition. I’m not against ruining his orgasm by slapping or hitting his balls as he’s cumming but in order for me to get him to that point a level of consistency is needed.

Mental stimulation and hypno

I have another confession. I’ve never tried hypnosis mixed with chastity play or been able to make slave D cum exclusively with verbal stimulus. Yes, dirty talk along with some physical touching works wonders but not without. Alas! I am human after all.

I’ve read numerous accounts of people being able to make their play partners cum with the power of their words and it’s always intrigued me, so I posted a tweet asking for help with this one.

Mistress Clarissa very kindly reached out to me to share her experience with us all:

Chastity is essential to training submissives. It’s invaluable in helping them refocus, shifting their attention  from their own immediate gratification, to prioritising their Mistresses pleasure. It provides the motivation and structure to obey instructions and to serve Her needs and wants first. It also creates a level of ongoing arousal that is useful in creating a more generally compliant toy. It aids in trying new things, pushing limits and in generally deepening submission. I have specifically found the combination of chastity and hypnosis to be highly effective in shaping subs.

Of course it’s also about teasing, the exquisite longing, aching, suffering, squirming and leaking that ensues after some time. Once in moderate trance, using an established verbal, or physical trigger I can edge my subject indefinitely, even forcing a release whilst they’re still in chastity, if I want that. I generally opt to leave them squirming and denied because I love the ongoing power exchange.

We also received a message from one of verified chastity keyholders, the wonderful Rosie Henderson, who has great experience with hypno play:

Hypnosis and chastity are a perfect pairing. They’re both individually able to amplify the intensity of other kinky themes in a session, summon a sense of overstimulation without my direct physical contact and are some of the sharpest tools in my toybox to reinforce my power and control over a good boy. When I combine the two it becomes even more intoxicating, the teasing and denial of mind and body; sometimes aligned so he can feel my fingers where the bars are pressing into flesh, sometimes in contrast so he can feel his mind, my mind, explode while his body is barely twitching.

While guiding subconscious edging and orgasms is fun, there is nothing quite like leveraging my hypnotic, manipulative voice to induce a locked release. One of my submissives is only allowed to release while he’s locked. He can’t do it by himself, but after years of being trained to obey a particular tone that I drop into and my simple countdown after a denied stretch, he wouldn’t have it any other way. Other toys have had the panicked pleasure of being hypnotised into release without touching, my voice in their ears and all the blank space between them, while out in public, so focused and worked up that it becomes inevitable that their body will obey my voice no matter what.

My subs describe feeling helpless, vulnerable and in awe of the sensation of being essentially hijacked, all things that hypno and chastity toys opt into willingly to varying degrees. A locked release while in a trance state is just a demonstration of having given in to both the well-placed subconscious suggestions and explicit demands of a dominant woman. It’s not to say it’s easy to do, but for a locked, brainwashed boy, nothing needs to be hard when you just follow my voice.

My final words

There’s my list of some of my favourite ways to make Slave D come whilst he is in chastity. Does my list match yours? Is there something super obvious that we’ve missed? Is cumming in chastity something you personally enjoy or do you prefer being uncaged for a release?

Thank you again to Mistress Clarissa and Rosie Henderson for sharing their experiences with hypnosis, what a fascinating practice. Now if you’ll excuse me - Slave D and I have a new release method to practice…