Chastity play is a type of sexual roleplay enjoyed by many couples around the world.
From chastity cages to ruined orgasms, there are many different ways you can partake in this niche form of sexual experimentation with your partner.
However, if you’re reading this, chances are, you likely already partake!
And—for whatever reason—you’ve decided that the pros of achieving an orgasm outweigh the risk of your keyholder finding out what you’ve done.
Well, we’re not here to judge: we’re here to help! If you’re determined to cum but not sure where to start, then this is the article for you.
For Obvious Reasons, Masturbation is Out
Cock cages, by design, are designed to prevent the wearer from getting an erection. If your keyholder was merciful, any hint of an erection will simply be restrained within the cage, prevented from reaching its full potential by the plastic or metal cage surrounding your shaft. However, if your keyholder is a bit more sadistic, then you might have some additional motivation not to get an erection. This makes traditional masturbation impossible, but that doesn’t mean you won’t be able to achieve orgasm. You’ll just need to get a bit more creative when trying to figure out how to cum in chastity!
Using the Cage
The main downside of not knowing how to cum in chastity is not being able to feel that sweet release. On the other hand, not having orgasmed recently will actually make it easier to orgasm. This will be a big help when you’re trying to cum using only the cage.
As you’ve likely noticed by now, the cock cage is fairly secure on your penis. It can only move a little bit. Still, if you’ve been holding back for long enough, this minuscule range of movement might just be enough!
Some men have reported being able to achieve orgasm simply by pushing down on the tip of the cock cage. Push down, let off, repeat. This process will take a while. Still, if you’re dedicated (and sensitive) enough, you might be able to get there eventually. Alternatively, you might be able to “jack off” the cage itself, utilizing the movement of the cage in an attempt to cum. Although both of these are technically possible, they’re not the most effective ways to reach the finish line. Keep reading for more effective solutions.
How to Cum in Chastity Using a Vibrator
Adored by women from all walks of life, a good old vibrator might be just what you need to get your juices flowing! Both bullet vibrators and wand vibrators are common choices. You may need to experiment a bit to see which one works best, but either one will work in a pinch! There are a few different places you can use the vibrator when trying to determine how to cum in chastity:
- Directly on the cage itself
- On your testicles, and
- On your perineum
Which erogenous zone is most effective ultimately depends on the individual, so this will also require a bit of experimentation. For the cage, press the vibrator against the tip for satisfying stimulation. Depending on the size of the cage/vibrator, you might even be able to get some direct contact!
For both your testicles and your perineum, the process is quite simple. Turn the vibrator on, push it up against your chosen bit(s), and wait for the pressure to build up until you cum! You can mess around with the speeds and patterns if you want to get a little creative.
Dildos & Anal Orgasms
For men, the p-spot is located about two inches inside of the anus. Stimulating this spot can lead to a prostate orgasm! Anal play isn’t for everyone, but fortunately, anyone can do it (so you’ll always have the option!). If you’ve never tried butt stuff before then the experience may feel a bit uncomfortable initially, but with time, it will become like second nature.
When using a dildo anally, safety is important! Only use flared base dildo for anal play, as the design of these anal-safe dildos will prevent them from being fully inserted.
There are three ways to achieve an orgasm from inside your anus, starting with using your fingers and using a dildo. The first option is self-explanatory: lube your finger, lube your anus, insert your finger, then start exploring! It might take a bit to get the hang of it, but once you find the spot, you’ll definitely know how to cum in chastity. If you don’t want to use your finger, using a curved dildo is another option. We recommend using a curved dildo since this will reach your p-spot easier than a straight one will. Some dildos offer additional functions like thrusting or vibrations that will make you cum even faster!
Utilizing a Prostate Massager to Cum in Chastity
If you’re looking for a more specialized approach then you might want to consider the third option: using a prostate massager! Available as a p-spot vibrater, and non-vibrating, as well as e-stim prostate stimulators, these toys are an expensive but effective way to get the job done. Their design is specifically made for prostate stimulation, using a combination of external and internal pressure to help you achieve orgasm. Depending on the design of your cock cage, you may not be able to enjoy external stimulation, but the internal stimulation should be more than enough on its own.
Like dildos, prostate massagers vary widely in terms of sizing (width and length). If you’ve never tried anal play before then we’d recommend starting small. You can always work up to a larger size on your prostate milking journey! Remember, anal play requires lube, especially if you’re not used to it. Not using lube certainly won’t help you orgasm, but you just might end up with an internal injury. Don’t forget the lube!
Asking Your Partner to Peg You
All of the options listed above have assumed that you’re just trying to “bust one out” without the keyholder noticing, but what if they’re into the idea? Well, the good news is you won’t need to take your cock cage off: you can simply ask them to peg you! Pegging, with preperation, adds another level of power play to your relationship, enforcing your partner’s ability to allow—or deny—your orgasm through anal penetration. Like before, you’ll be achieving an orgasm through prostate stimulation, rather than via the traditional route.
If you don’t already have the right equipment then you’ll need to grab yourselves a prostate strap-on. A complete set will include both the harness and the dildo, but if you already own a dildo then you can just buy the strap. To use a dildo in the strap-on harness, it will need to fit within the dimensions of the harness. It also must have a flared base to secure itself into the harness. Always check the measurement requirements rather than simply assuming it will fit!
How to Cum in Chastity? Get Creative With It!
There are a nearly unlimited number of ways to orgasm. It’s really limited only by your creativity and dedication to the process. What works for one man might not work for another, so don’t get discouraged if the first thing you try doesn’t work. Instead, simply move on to the next thing on the list and try again. You’ll eventually figure out how to cum in chastity consistently! Whether you’re going behind your keyholder’s back or trying to find an approved method of release, we hope this guide was of some help. If you fall into the latter category, have fun, you two! If you’re part of the former, don’t worry: we won’t tell if you don’t!
