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Can You Have an Orgasm While in Chastity?

Glistening steel penis cage

Glistening Steel Penis Cage

Just because your penis is locked up, doesn’t mean you’ll never get to orgasm!

Now, we understand if you’re a little confused. After all, staying chaste usually means staying away from sexual pleasure. But in most chastity relationships that tends to mean penis pleasure. There are still plenty of other ways to get your rocks off…

How to Cum While in Chastity

So how does a locked down man get his pleasure? Well, the most simple way is by being a good boy!

For the vast majority of men, chastity isn’t meant to be a complete denial of all orgasms for the rest of his life. And lets be honest, most Mistresses aren’t cruel enough to completely deny a man either.

In this kind of relationship, an orgasm becomes a reward. Something to be earned by good behavior. Keep Mistress happy and you might get them quite regularly. But disobey her and you might find your next orgasm getting further and further away!

There are also plenty of other ways to orgasm while your penis is safely locked inside its prison…

Prostate Orgasm

The prostate orgasm is a mythical thing to many men, similar to women squirting or even some of the confusion over the g-spot. The basic idea is to stimulate the prostate gland with gentle stroking or vibration, eventually leading to an orgasm without touching the penis at all.

The Prostate Gland: A small, walnut shaped gland found in a man’s genital region. It controls the junction between a man’s bladder and his testicles, allowing either urine or semen out, but only one at a time.

Although the prostate’s primary function is a biological one, it can also feel very pleasurable to stimulate. Unfortunately, it’s not in a location which gives easy access.

The easiest way to reach the prostate gland is through a man’s anus. It’s usually 2-3 inches deep, and towards the front of his anal cavity. While it can be reached with fingers, it’s usually easier to use a prostate massager as these are shaped specifically to stimulate the gland.

Prostate massage isn’t something you can just do though. You’ll need plenty of practise before you can reach orgasm with this type of stimulation. Once you can though, you’ll notice that there’s no longer a refractory period, so you can cum over and over again!

Anal Orgasm

Another, more common, way for caged men to enjoy themselves is anal play. This is great in a chastity dynamic as it often lets their partner take full control, and amplifies the feelings of helplessness and subservience a man commonly feels during chastity.

There are, of course, many different ways to experiment with anal play. Sex toys like butt plugs, anal beads, and dildos are great, and even prostate massagers provide anal stimulation alongside prostate stimulation. For the less adventurous, even the humble finger can do a great job at massaging the many nerve endings found in your anus.

For male chastity though, the pinnacle has to be the strap-on. Handing over complete control and letting your partner fuck you plays into so many of the aspects of male chastity that men enjoy. It can be sensual and close, hard and humiliating, deep and emasculating, or down right enjoyable.

Some Mistresses will even use anal sex as a punishment for unruly slaves!

But for those of us who enjoy anal play, it can also lead to some spine tingling orgasms that don’t involve your penis.

Lightweight steel chastity cage with urethral sound

Lightweight Steel Chastity Cage with a Urethral Sound

What is a Sissygasm?

You can also take your pleasure in a completely different direction while wearing your cage. Enter, the sissygasm…

A Sissygasm: A loose term for an orgasm achieved in a more feminine way.

You’ll notice our definition is a bit vague, and that’s simply because there isn’t a good definition of a sissygasm out there. It means a lot of different things to a lot of different men, but at the core it involves something less than masculine.

For sissy slaves, the entire goal is to completely shed their masculinity and be treated like a woman. They don’t deserve to be a man, and this includes their orgasms. They’ll often wear very small cages to keep their penis confined and concealed, and some even refer to it with terms like “man pussy” or “little clit”.

So when it comes to pleasure, they want to be treated like a woman too! But how exactly do you have a sissygasm?

How to Have a Sissygasm

To put it bluntly… however you want to!

Some men focus on alternative stimulation, like nipple play. Some will stimulate the tip of their caged cock with a finger, just like a woman massaging her clitoris. Many opt to go for the penetrative route, getting fucked by a strap-on or even another man!

Another route is the fabled “hands-free orgasm”. This can involve careful mental conditioning, almost like meditation, to focus on thoughts of pleasure, stimulation and sex to bring you to the peak without even a single touch.

Whichever method they choose, the most important thing is they don’t get to cum like a man. Their pathetic cock remains caged, and any cum simply dribbles out. They don’t get to have an erection, or be the one doing the penetration. They’re just a pathetic little sissy, being used for someone else’s pleasure.

What is Orgasm Denial?

Of course, no discussion of orgasms during chastity would be complete without looking at the ways a man’s pleasure can be used against him!

Orgasm Denial: The act of controlling your urges to completely deny orgasm, even during sex.

Orgasm denial is one of the most powerful weapons in a dominant partner’s arsenal. It provides complete control over an encounter, even over a man’s most primal urges. And there’s more than one way to use it.

The simplest we discussed earlier. Misbehave and your Mistress might deny you an orgasm for another day, week, or even month.

But orgasm denial can be more than that. For many men it becomes about self control. Just like you train other parts of your body to lift weights or ride a bike, you train your penis to function without cumming. You might do it because you want to last longer in bed for the one you love, or maybe just because you enjoy torturing yourself.

Orgasm denial can also lead to much more explosive finishes. A Mistress might let her slave have sex with her, but give him strict instructions that he is not allowed to orgasm without her permission. He can ask, he can beg, he can scream! But until she says yes, he’s got to control himself. But when she finally does let him, the result can be incredible.

Hands off silicone cage

Hands Off Silicone Cage

How About a Ruined Orgasm?

Another way to weaponise a man’s penis is the ruined orgasm, and this one’s a little crueller.

Rather than outright denying his orgasm, you let him think he’s going to have one. Then just as it’s starting, you completely stop all stimulation. His cum will dribble out without all the usual satisfying throbbing in his penis, and he’ll be left more frustrated than ever!

You can make his ruined orgasm even more frustrating by combining it with edging.

Edging: The act of bringing a person to the edge of orgasm, then stopping stimulation just before they get there.

Keep stimulating and edging him for a while, letting him get closer and closer to his precious release, then at the very last second, ruin it for him!

Another torturous way to ruin a man is by giving him something he’s always desperate to do. For a lot of men this will be something like anal penetration or a blowjob. Let him think he’s getting a real treat, only for it to be ruined at the last second.

Sex While Wearing a Cock Cage

Just because he’s caged, it doesn’t mean he can’t have sex!

Obviously we’ve already discussed the other parts of his body that can be stimulated instead of his penis, but what about good old p-in-v sex?

This is a truly great way to play with his mind, as his actual penis will still be locked up tightly and getting no stimulation whatsoever, but the rest of his body will be going through all the usual motions and bringing pleasure to someone else!

There are a few ways to go about this. The simplest is a strap-on. Simply attach it around his waist, directly above his cage, and let him go to town!

If the positioning of a strap on isn’t quite doing it for you, then you can look for an attachment to go over his cage. For the other partner, this won’t be much different to a dildo, but for the poor man it will keep his caged cock completely away from the action.

It might frustrate him, but often it can encourage him to be even more attentive to his partner’s needs without his own pleasure to distract him. And if he does a really good job, maybe he’ll get some un-caged pleasure after all!

It’s Chastity, Not Abstinence!

Just because his penis is locked up, and he’s staying away from traditional pleasure, it doesn’t mean turning him into a monk. There are plenty of ways to enjoy sex while a man is caged, both taking advantage of his predicament to tease him and to please him. So if you’ve got an active sex life, don’t be scared off by the cage! Start enjoying the new kinds of pleasure chastity has to offer now.

Natalia Author Profile Picture


A secretary turned Mistress who had never even heard of male chastity, but got sucked into the community and now makes a living writing blogs and guides to help both slaves and Mistresses alike. She first discovered chastity at the age of 25, and has been a full time dominant for the last 3 years.

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