Teasing and (Sometimes) Pleasing: Ideas for Chastity Play

Posted by Bradley Donner on May 01, 2021

The trial period is complete – the caged partner has adjusted to their device, the keyholder feels comfortable in their role.

So…What next?

Lots and lots of fun, sexy experiences, that’s what!

Below are some chastity play ideas to get you started. There are example rules that a keyholder might set, teasing activities the two (or more!) of you can carry out together, and even a few suggestions for that rare and much-anticipated orgasm.

There’s no end to the fun you can have with male chastity – pun fully intended!

Rules, Rules, Rules (But the Fun Kind, We Promise)

Sure, the word “rules” doesn’t exactly send a tingle of arousal down most people’s spines. It’s something you’d associate more with strict teachers or demanding parents than erotic fun. But when it comes to chastity, rules are a supremely sexy way for a keyholder to exert their dominance and remind their caged partner of exactly who’s in control.

Rules for a male chastity relationship come in two common forms: rules regarding punishment and those which deal with rewards. We’ll discuss both kinds here. Of course, don’t ever let yourself feel limited to just one or the other – mix it up to keep you both on your toes!

Someone’s Been a Bad Boy

“Punishment rules” refer to any rules set by the keyholder which, if broken, result in negative consequences for the caged partner. The consequence, or punishment, could be anything from spanking to an hour in handcuffs to – best and worst of all – a further extension of the chastity period.

While the keyholder might assume unilateral control in deciding what actions merit punishment, the punishments themselves should be talked over by all participants to make sure everyone is on board and their limits are being respected.

Here are some fun example rules that might earn a particularly bad boy some more time locked up:

The caged partner must refer to his keyholder by their preferred title (such as Master/Mistress or Sir/Ma’am) at all times. Each time he fails to do so, he earns himself one spank. Spankings are delivered at the discretion of the keyholder, so they can spread them out or save them up for one delectable punishment session.
The caged partner must send at least one picture of his locked cock to his keyholder each time he attends work. Each day he forgets adds one day to his period of chastity.
During all teasing sessions, the caged partner must announce when he is getting close to orgasm. Failure to do so resulted in being locked back up immediately and his next orgasm delayed even further.

If you prefer to have a written down, physical version of your particular partnership’s set of rules, check out our example chastity contract for inspiration.

Spanking and chastity extension are always classics, but keyholders, don’t be afraid to get creative with your punishments! Perhaps each rule he breaks leaves your man wearing one less article of clothing. Or he pays for his bad behavior by servicing you in the way that pleases you most. You’re the keyholder – control is yours!

Have fun! Let your imagination run wild! Your caged partner will love it, and you’ll have him on his best behavior in no time!

Who’s a Good Slave?

Of course, punishment isn’t the only way to go about making chastity play fun and interesting. “Reward rules” encourage good behavior and satisfying the keyholder; when these rules are followed properly, the caged man earns himself a treat.

Said treat can be anything from a teasing game or sexual favor from his keyholder to time out of the cage, days taken off his current chastity period, or – if he’s been very, very good – an orgasm!

Here are some suggested ways a caged man might earn his mistress/master’s favor:

The caged partner prepares the keyholder’s favorite meal once a weak. He cooks, serves, washes dishes, and maybe even dresses up in a fancy suit to act as waiter or butler. In exchange, he earns an uncaged teasing play session with his keyholder.
The fewer clothes the caged partner wears around the house, the more hours are taken off his current chastity session. If he spends an entire day at home completely naked except for the cage, he subtracts an entire day! (If you have children or live with roommates, this rule could apply to the bedroom or other private spaces)
Once the caged partner has given the keyholder three orgasms in a row (using methods of the keyholder’s choosing), he is rewarded with one of his own!

Reward-based rules are a great way to make sure both partners are getting what they want and need out of the relationship. The keyholder sets rules based on what they desire, and grants the desires of the caged partner when they are fulfilled. Thoughtful and sexy!

Check out our chastity stories for even more ideas of ways to reward your perfect chaste gentleman!

Tease and Denial

If male chastity is a part of your relationship dynamic, tease and denial sessions are probably a pretty frequent occurrence. “Tease and denial” refers to any sexual activity that does not end in the caged partner achieving orgasm. His cock may be unlocked for the session, but, if it is, he’s returned to the cage immediately afterwards.

The keyholder, of course, is allowed to orgasm during these sessions – as many times as they desire!

We’ve compiled some example activities that you might include in your own erotic teasing sessions. There’s something for everyone – first-time chastity explorers and long-caged veterans alike will find something to turn them on here!

Everyday Teasing

Not every tease has to be an elaborate, lengthy ritual. In fact, teasing doesn’t have to involve unlocking him at all! Here are some things a keyholder can do during the day to keep their caged man desperately and horny 24/7:

Talk about his situation. Drop mentions of his locked cock into casual conversations around the home. “Oh, honey, I bet you want to come so badly right now. Too bad, you can’t.” “Is your cock feeling nice and full for me? Don’t you just wish you could release it everywhere? Just one more week….” Especially effective at times when he isn’t expecting it – try mid-meal, while watching TV or right before he leaves for work!
Alternate those moments of teasing talk with periods where you don’t bring up chastity or his cock cage at all. Keep his key close and visible, but don’t talk about it. This will be utter torment for him, especially as that lock on his cock keeps him constantly aware even as you pretend nothing unusual is up. Try this out close to a promised orgasm day – it’ll leave him nervous, worked up, on edge and even readier than usual to explode!
Wear sexy clothes – whatever that means to you. Hang out around the house without undergarments, or just in undergarments, or even naked! Don’t let him touch without your permission – but odds are, just looking will be enough to drive him wild!
Have your caged partner wear sexy clothes. Pick out an outfit for him – perhaps tight pants and no undergarments to emphasize the feeling of his cage against his skin even further. If he’s into the sissy scene, select “feminine” clothing such as silk panties, garters and stockings – maybe even under his work clothes!

Teases for the Bedroom

Soon enough, that constant, everyday teasing will snap even the strongest self-control and leave any caged man desperately on edge. What next?

Well, then, it’s time to take things into the bedroom.

Here are some more extended teases that keyholders can carry out to get their caged man so close to – but yet, keep him so far from – that release he desires.

Release the caged partner for one hour. During that hour, he must touch and stroke his penis enough to remain erect, but NOT allow himself to come. For added challenge, have him do this while watching TV or listening to relaxing music or a meditation tape.
Unlock him just enough to have him read his keyholder a sexy story. (Might we suggest one of the ones here on our site?) The keyholder might touch themselves – and orgasm if they like! – to add that extra layer of teasing, but no touching for him!
Go shopping for a sex toy together, such as a vibrator or strap-on. Have the still caged partner use it on the keyholder, watching them have orgasm after orgasm while their own cock remains on edge and unable to release. For extra fun, use the same toy on his prostate – but no coming!

Those partners looking for something a little harder, some fun “advanced level” teases include: keeping him handcuffed in an uncomfortable position while the keyholder pleasures themselves with fingers or a toy, using him as a footstool or table during a meal or relaxation time, or stimulating his sensitive nipples and testicles while he’s caged and nowhere near his next orgasm.

Riding the Edge

Now, let’s talk about edging.

Edging is one of the most common tactics used in male orgasm denial, and is a part of many enforced chastity relationships. Edging refers to a technique in which the penis is stimulated until only a few strokes away from orgasm (“on the edge”). When the edge is reached, all touching is completely stopped and the cock is returned to its cage.

Edging is an erotic combination of exhilarating and frustrating for the man. There are many ways to have fun with this technique – the caged partner can touch himself or the keyholder can use hands, mouth or a toy such as a vibrator. Alternate brief, repeated edging sessions with longer, slower ones (often called “riding the edge”) to keep things fresh.

Learning to know exactly when his cock is on the edge of orgasm can be difficult to learn at first. The male orgasm is typically thought of as quick and explosive, but edging will allow for longer and more intense orgasms that will absolutely blow his mind! Start with a few practice sessions, and don’t punish him too much for the inevitable mistakes.

Once he’s gotten to knock his own cock well enough, have the caged partner verbally announce when he reaches the edge. Many keyholders find their partner’s desperate, strained admissions of “gonna…come” and “almost there…” to be the most arousing parts of their tease and denial sessions.

The Big Finish: Orgasms

Of course, eventually, it’s time for the caged partner to have an orgasm.

Many men who fantasize about chastity might think about being locked up forever with no end in sight. However, the harsh reality is that after a certain period of time (usually 7-10 days), it gets easier and less arousing and fun. Desire for orgasm tapers off. The caged man doesn’t think about orgasms nearly as much as he used to. To put it simply, he doesn’t want it so badly any more.

So, keyholders, give your caged men the occasional orgasm. It’ll keep them wanting it – and you – just as desperately as they did the day they were first caged.

That doesn’t mean, of course, that there aren’t plenty of ways you can have fun with his orgasm when he does finally earn it.

Some of our favorite examples include:

Unlock his cock, but don’t make that the source of his orgasm. Milk his prostate with a toy while using your fingers to stimulate his nipples and testicles. It’ll be just as explosive, but still leave his cock feeling desperate and neglected when you return it to its cage.
Take him somewhere (semi) public, such as a secluded part of your backyard or in front of a window, and make him orgasm there. The thought that people might see his uncaged cock finally getting to explode can add to the eroticism of the experience.
Cum eating. Have the caged partner lick up the product of his release – every last drop. For extra fun, make him do it on his knees and tie his hands behind his back until the task is complete.

Of course, there’s also one more kind of orgasm that caged men can enjoy as part of their male chastity relationship – the extra-intense extra-frustrating ruined orgasm. Learn more about ruined orgasms and how to both have and give them here:

We hope these ideas and suggestions will help your bedroom life be spicy, satisfying and full of just the right amounts of teasing, denial and explosive release!