19 Fun Male Chastity Games & Challenges To Experience

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When you get started in chastity play or any kink, there is always a fun ‘honeymoon’ period. But when the novelty wears off you need to think outside the box to keep things interesting… this is where chastity games come into play!

chastity games cover

Bring the magic back to your cock cage by swapping out the standard release requests for some fun chastity challenges. 

Gamification with a reward or punishment system will not only spice things up but it can also help reinforce sub/dom relationships. 

Make that sub EARN their penis freedom! 

The uncertainty and extra risk factor will heighten the sexual tension for both the keyholder and “lockee” and will have that caged up cock tingling with anticipation

Let’s play chastity games!


Lucky Dip

1. Lucky Dip

Get your sub and dom heads together and let your creative juices flow for this one. On slips of paper, write down as many rewards and punishments as you can think of

Fold them up and place them in a little silk pouch or similar. Then, every evening or as often as you wish, the submissive should dip into the bag and choose their fate.

Here’s some inspiration for the kind of things you can write: 

  • 2 more days of chastity
  • Edging for 10 minutes
  • 5 minutes of ball fondling
  • Bend over buddy, it’s pegging time!
  • Give your keyholder a back massage
  • Pussy worship, now!
  • Sex but with no orgasm for you, loser.

Put It To The People

2. Put It To The People

Some kinky couples like to document their chastity adventures on blogs, social media channels, or in fetish forums, anonymously or otherwise.

You can bring your followers and fellow kinksters in on your games. 

Create a poll on how long your man’s cock should stay locked up for. Or post a photo of his tackle in chains on the condition that for every ‘like’ or comment the post gets, you add a day to his chastity.

You can also ask for their ideas for teasing or extra punishments. 


Beat The Clock Key Seek Challenge

3. Beat The Clock Key Seek Challenge

There are a few ways you can play this chastity key treasure hunt. In the first version, the keyholder should hide the key in a specific agreed-upon location.

For example, the key is somewhere in the bedroom or in the living room. 

Then, put time on the clock and the search begins! If they find the key before the time is up, they can be unlocked and bring themselves to orgasm.

If they don’t, well then, chastity continues until the next challenge. 

The other way to play the game is to make him strip down to his chastity device, blindfold him and command him to crawl around on his hands and knees in search of the key.


Dice Days

4. Dice Days 

Dice are a great way to determine punishments for any time your submissive misbehaves.

Just roll the dice and whatever number they give is how many extra days of chastity your disobedient sub should have. 

The more die you use, the crueler the punishment, and the greater the lesson. 

You can also use dice before lock-up to determine how many days their chastity session should be.

If you’re using two dice, instead of adding the numbers together, why not multiply them?


Double Devil Dares

5. Double Devil Dares

Double Devil Dares is a great game for those who really like to humiliate their caged partner.

The keyholder should come up with two challenges, each of them difficult and as equal in humiliation levels as possible.

Then, give your male chastity slut the choice of which ‘devil dare’ he will attempt. Of course, failure to choose or to complete the task should come with a high stake punishment. 

But be sure to reward your sub with something extra pleasurable if they complete the dare successfully or to your satisfaction! 


Wheel Of Pain Or Pleasure

6. Wheel Of Pain Or Pleasure

Taking inspiration from the Wheel of Fortune, this is the ultimate game of chastity chance! If you have the time and like to get crafty, you can create your own spin wheel. 

Or better yet, get your male sub to make it for you. But the keyholder should be the one to come up with the ‘pain or pleasure’ chances.

Have a variety of sweet rewards, delicious dares, and painful punishments. Then each day, spin the wheel and see what your chastity chance will be!


Back To School

7. Back To School 

If you or your chastity play partner are also into teacher/student roleplay, this will be extra fun. 

As the key holder, you should choose a topic that you know well or have an interest in, since you’ll have to come up with the questions. 10 or 20 of them should do. 

Then agree on a point system, i.e., how many chastity days should be added for incorrect answers. If you’re feeling generous, you can also add rewards for correct answers. 

It’s also a great game if you are actually studying or training for something. It will certainly make study days so much more interesting!


Best Of Six Chastity Dice

8. Best of Six Chastity Dice

Here is another chastity game led by the dice. All you need is one dice and six outcomes.

Five options should be something that will torture and tease your locked up man. And just one that will allow them to cum…the best of six. 

Here is some inspiration:

  1. One hour of your favorite porn but no release and no masturbation allowed.
  2. Watch your keyholder masturbate and bring themselves to orgasm. No touching.
  3. Give your keyholder three orgasms in a row by a method of their choosing.
  4. Strip and take a photo of your locked up cock. Post it online and thank everyone who comments.
  5. Add five days to your current chastity session and roll again.
  6. Sexy Six! Release time, and you get to orgasm anyway you like!

Queen Of Cocks

9. Queen of Cocks

This is a pretty easy game to get going. No complicated rules, but it really ramps up the anticipation. Get yourself a standard deck of cards and shuffle them.

Then every day, take a card from the top. 

If you pull a Queen, your sub can be released and allowed to cum. When he’s all done, lock him up again and the chastity continues until the next Queen of Cocks is pulled.


Coin Toss Cock Boss

10. Coin Toss Cock Boss

Settle on the number of chastity days…let’s say 20 days of locked up cock. At the end of each day, you flip a coin. 

Heads, you add a day to your chastity period. And if its tails, do you reduce it by a day? 

Hell, no! That would be far too easy. 

It simply stays the same. But your chastity sub has to give you an orgasm. Pleasure for the keyholder, while the sub ‘enjoys’ the pain of a locked cock that can’t enjoy his erection.


1 In 20

11. 1-in-20

Hide the key to the cock cage amongst a bunch of 20 keys. Then give your sub 60 seconds to find the right key to unlock themselves.

If you want to make the game harder, add more keys, or lessen the time they have to try. 

Make it even sweeter by adding rules like, should they fail, you can add the number of tried keys as days to their lockdown.


Blue Balls

12. Blue Balls 

Have ten blue marbles and one red marble in a bag. Every day, your chastity sub should choose one marble. If it’s blue, then lockup continues for another day.

When he finally draws the red marble, he gains his freedom and maybe an orgasm, if you’re a kind keyholder! 

You can make this one even more interesting by adding in other colors and assigning them to different fun things. 

For example, pull a yellow marble? It’s a no underwear day for your cock-caged partner.

Pull out a purple marble? Give your keyholder a sensual massage and feel that cock strain!


Postman’s Bag

13. Postman’s Bag

Make snail mail fun again with this game! Get five (or more) envelopes. Lock up your boy’s love stick and pop the key into one of the envelopes. 

In the other envelopes, put some smart-assed comments on a note. Something like, “Maybe tomorrow, loser.” 

To be totally sure the key envelope doesn’t arrive first, I would suggest posting it a day later! 

By the way, whenever you’re letting the key out of your control, ALWAYS have a spare for emergencies. 


Deck Of Delights And Dares

14. Deck of Delights And Dares

This one will take a little time and imagination but it should last a long time so it will be worth it.

Get a deck of cards and on a piece of paper, write down the names of all the cards and next to each one, write a pleasure, a pain, or a challenge

Shuffle the pack each morning or however often you decide and let your sub choose a card.

If you can’t think of so many challenges, then don’t worry. Think of four forfeits for the four suites, things that can easily be repeated as per the value of the card pulled from the deck. 

For example: 

Hearts – pegging thrusts

Clubs- spanking/flogging

Spades– ball slaps

Diamonds– butt plug wear

Jokers– release for orgasm 

If your sub pulls the 10 of Hearts, they have 10 thrusts of an anal dildo. If they pull the 5 of Spades, it’s 5 slaps to the balls. 2 of Diamonds? 20 minutes butt plug time. 

You get the idea! 


Pin The Face-Dildo In The Pussy

15. Pin the Face-Dildo in the Pussy

Basically, a grown-up and kinky version of ‘pin the tail on the donkey. Strip your chaste submissive down to their cage and strap them into a chin dildo gag.

Then blindfold them, spin them around a few times to disorientate, and then assist them to their knees. 

Now it’s time for them to crawl around to try to find your pussy or ass with their chin dildo. If they can hit their mark, you can assign a reward of your choosing. 

You can help by shouter ‘warmer’ or ‘colder’. Or make it harder by adding in a time limit or moving around the room to avoid them. Great way to humiliate your submissive! 


Cum Quick

16. Cum Quick

In this game, you free their cock and give your submissive a certain amount of time to achieve orgasm. If they don’t manage it within the time, you have two options:

  • Let them continue to orgasm, but add the extra seconds/minutes as days to their next chastity sentence, OR
  • Stop their play immediately and before they achieve orgasm. Lock them back up to begin their chastity sentence straight away.

To make it more challenging, you can add some numbing lube!


Cock Locked Chores

 17. Cock Locked Chores

The dominant partner will create a list of chores that the sub should complete by a certain time.

The chores must be done properly. No half-assed attempts allowed!

If they manage to complete the chores to your satisfaction, they can be released. You can also add in a point system for how good a job they did and give extra treats. 

For example, if you award them 7 out of 10, they get to penetrate you for 7 thrusts before being locked back up.

Or you will suck them for 7 seconds. 10 out of 10 could be a full orgasm.

It’s up to you as the keyholder! 

Deciding on the point rewards together beforehand can also be a fun way to increase the anticipation.

You can also add some humiliation play to this game. Make them dress up as a French maid or make them wear a cute fur tail butt plug as they complete their chores. 


Photo Chastity Challenge

18. Photo Chastity Challenge

This is a fun game for brave subs, exhibitionists, chastity play partners in a long-distance relationship, or just as fun to dominate your sub while they are on their own.

Challenge your sub to take a photo of their caged up cock in a public place or while they are going about their day. You can make it as daring (but safe) as you like. 

For example, you can command your chastity sub to go to the toilets in their workplace, strip in the cubicle and to take and send you the proof of their obedience. 

Add a certain time to the challenge and if they are late, there should be a suitable punishment.

Or, if you’re more daring, choose a public space where they should expose their cage.

Just be careful when choosing the location. The danger should come from the POSSIBILITY of being seen.

But you should never put your sub in a position of being arrested for public indecency! 


Board Games Changed For Chastity

19. Board Games Changed for Chastity

Pretty much any board game can be transformed into a chastity game. You just change the meaning of the rules to suit your kinky desires.

Points can be collected for freedom or rewards. 

Or you can assign pleasure and pain across the layout of the board. 

Snakes and Ladders is an easy one. Just break it down to one roll of the dice a day…When your sub finally gets to the end, they can be released. 


Let the Games Begin!

Chastity games really ramp up the teasing torture of orgasm denial.

Plus, if you’re into any other kinks or fetishes, you can just add them in your chastity lifestyle.

Enjoy your chastity games with servitude, humiliation, sex toys, exhibitionism, or roleplay…whatever floats your dirty little boat!

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