Chastity Challenge Game

Playing

Here’s a chastity game you can play with your toy. There are a few ways that you can play, whichever suits you and your needs best at the time is the way you should play:

  • Random Number Generator: Just go to this random number generator, set it to 1 – 65, and click generate. Whichever number it lands on is the dare/challenge or game you must choose.
  • Print The Cards: Print this page, cut out the dares, shuffle, and then pick one at complete random.
  • Use the list for inspiration: Just browse the below ideas and use the ones that you see fit for your toy.

When Your Toy Fails

If you don’t have an item necessary for the challenge you have to do one of the following:

  1. Add punishment days with the number you have picked. For instance, if it’s a 6, then add 6 hours/days of punishments to your total.
  2. Do the challenge that is either above or below the current challenge.
  3. Add time to the lock up and pick another number.
  4. Use a chastity punishment mentioned in this list.

This is only applicable if the challenge is impossible to do, if toy can do it but refuses then toy isn’t allowed to cum for 1 week and must stay away from this game for that will before your toy can come back and continue where he left off.

Chastity Challenges/Dares

1. You Have This Much Time To Cum

You have to set a timer for 1 minute, you have to cum in that time window. If you succeed then you put your cage back on, if not, then you don’t get to cum and you have to add however much time Madame says onto your lock-up time.

2. Add Time On Because I Said So

Oh, you only had 30 minutes left of wearing your cage? Whoops! Add 4 more hours because Madame said you have to. Hopefully, you were busting to cum, and hearing this news makes you so very sad.

3. Hide and Seek

Madame will hide your key around your house. You then have to decide how long you get to find it. make sure to time how long it took you to find the key

After you find the key Madame gets to decide if

  1. If you get unlocked.
  2. If you get to cum.
  3. How much time should be added or removed from your lock-up time.
    • Some examples:
      • If it took you 10 minutes – add or remove 10 minutes
      • If it took you 5 minutes -Add 5 days
      • If it took you 20 minutes – Multiple 30 by 10 and add that many minutes to your time

4. Take Two Days Off

Take two days away from the challenges and keep your cage firmly on. Madame is free to tease you but you must not cum.

5. Roll the Dice

  1. Roll 2 6 sided dice, whatever number you roll, add the 2 numbers, multiply it by 10, and add that value as minutes to your chastity lock-up time. If you roll a double six, add 12 hours
  2. Madame rolls 1 die you roll the other. The higher number wins. Multiply the difference between the 2 dice by whatever amount Madame says – If Madame wins add that time to your lockup, if you win remove that time. Madame decides if it is seconds, minutes, hours, or days.

6. Dress Up As A French Maid And Clean The House

Put a french maid outfit on (if you don’t have one then wear some slutty lingerie) and clean your whole living space while wearing it, you’re not allowed to take it off until you’re done.

7. Mail Your Key

You have to put your cock cage key in an envelope and mail them to yourself. It could take days for them to arrive and they could even get lost in transit.

8. Cum On Your Cage

Take a break from your cage, tease and edge your orgasm before you cum on your cage, and once you’re done put it straight back on.

9. Blindfolded for the Night

You must wear a blindfold for the rest of the evening, Madame can do what they like to you. Completely render your eyes useless with a blackout blindfold that will take one of your vital senses away.

10. Remove the Option

Madame is going to hide your keys where you can’t find them or get to them. Now you just have to be locked up until Madame feels like like retrieving your keys. Hopefully she doesn’t forget.

11. Pleasure Madame To Completion

You have to please your Madame to complete satisfaction, she then must get you to the point of ejaculation, but stop before you ejaculate. She can cycle through this a few times, once she’s done, she has to cage you up without you ever having an orgasm.

Premature ejaculation or cumming during this challenge is costly and it’s left up to the Madame to decide the punishment.

12. Try Not To Cum

You get allowed out of your cage (yay!) and Madame has to wank you off for 5 minutes, if you cum, you have 2 hours/days added on to your chastity sentence and if don’t cum in that five minutes you get two hours/days taken off your sentence.

For extra difficulty, use a vibrator and place it on the cock on a high setting and let the intense vibrations do the work for you.

13. Orgasm Time

You have to make Madame cum [insert a number of times] before you can cum. It doesn’t have to be all on the same day, it can be spread out as far as long as Madame wants.

14. Ruined Condom

For the next month, you’re only allowed to cum into a condom.

Once you’ve come into a condom you must leave it on for 20 seconds, and then empty the contents into your mouth, keep it in your mouth for another 20 seconds, then you can swallow and put your cage back on.

15. You Must Be Tied And Tickled

Madame is going to tie you up nice and securely and tickle you until they say. It’s pure torture and a really fun time for Madame!

16. Add 4 Days For Fun

Getting this challenge is going to make you a very sad caged slut. 4 whole days have just been added to your total time inside your cock cage. Have fun!

17. Remove 1 day

You’re lucky, you get to remove 1 day from your lockup. If that means you get to be unlocked – well that’s up to Madame isn’t it? Ask her.

18. Wear A Butt Plug For 2 Hours

Today you need to wear a butt plug for 2 hours, use the timer on your phone, you can take it out in this time out, but you have to have a total of 2 hours of butt plug wearing by the end of the day.

19. Run Madame A Beautiful Bath

Get up and run Madame a hot, soapy bath. Light some candles, put on some relaxing music, and make them feel like a million dollars.

20. Pretty in Pink

Slide some pink panties over your cage for the next 7 days.

21. Naked For The Night

Once you’re home for the night, you must remove all of your clothes and only wear your cage until the next morning.

22. One Free Orgasm

You have earned one free orgasm token, to use whenever you want (expires in 1 week from getting this number).

23. 30 Minutes Of Pegging

It’s time to get that ass ready for Madame.

Bend over and let Madame use the dildo of her choice to peg you, this is a treat so show complete appreciation, if there’s not enough appreciation given, then maybe there will be days added but that’s up to Madame to decide.

24. Strap On Replaces You

For the next two weeks or number of times (or longer/more if Madame decides so) the strap-on replaces your dick. Madame will only give handjobs, blowjobs, and sex to the strap on and your cock will be left un-pleasured. This goes for whether you are caged or not caged.

25. Get Pegged While Wearing Something Sexy

Madame will peg you wearing whatever outfit they see fit, might be nothing, it might be a thong, might be stockings, she might ask you to wax, it’s all up to Madame.

26. Cum Window Of Time

You landed on something very exciting. You have to cum in an exact window of time.

Masturbate for however long Madame says. Then as soon as she says to cum you have 2 seconds to do so.

Once the time window is up you MUST stop, it doesn’t matter if you are is mid-ejaculation, or if you didn’t get your release, failing to do so inflicts a 7 day addition to your cage time (of course Madame can specify less or MORE time).

27. You Can Only Cum On This Day and Time

Madame picks the day, time, and how long you have to cum.

For example: you can now only cum on a Wednesday at 6 PM on the dot and you have 4 minutes.

Miss the time and you have to wait for the next window.

The only exception to this rule is when you’re fucking Madame because they want you to and even then it’s completely up to them if you did enough to deserve an orgasm.

28. Cum Deposit

You must cum in a jar at least 4 times, with video proof (if Madame is not present) and the cherry on the cake is that you only have X number of minutes to do this – Madame gets to pick. 30 minutes? 10 minutes? Who knows.

Failing to do so adds to your time – Madame gets to choose how much time to add.

Don’t want the challenge? Add 5 days to your lock-up time.

29. The Right Marbles

Put 8 marbles in a bag, 7 of one color and 1 of another color. Shake the bag up and If you get the 1 color you get to have an orgasm. The game continues and so does your lock-up, every day until you pick out the single-colored marble.

You can use as many marbles as you like to decrease/increase the odds. You can also use anything from painted pebbles to ripped-up paper, whatever you have laying around.

30. Wheel Of Fortune

Make a wheel with 10 challenges/games from this list and take it for a spin.

You can make this using a spin wheel and paper or you can use SpinTheWheel to create the wheel.

31. Which Hand?

Have Madame hold her hands behind her back. In one hand is an immense pleasure, on the other hand, is more time to be added. Now pick one.

Do you get the best of three? Did Madame lie about which hand was which? Doesn’t matter it’s all up to madame.

32. Magic Wand Fun

Stimulate his cage with a magic wand. You have to set a timer for 15 minutes, place the magic wand on the cage and let it do what it needs, his job is to last 15 minutes without getting aroused, if he cums – add a day to his time. If he doesn’t cum he gets to have an orgasm and no days added to his total.

33. Ejaculating Dildo

It’s time to try pegging or masturbating with an ejaculating dildo, even better if you hate the idea of a cock shaped dildo going into your ass and cumming inside of you. This isn’t about enjoyment it’s about doing as you’re told and this challenge is telling you to fuck yourself with an ejaculating cock.

34. 30 Minutes Of Pleasure

You are allowed to watch 30 minutes of porn, use your dildo, play with your nipples, Madame can tease you, and masturbate themselves off but you’re not allowed to lay a single finger on your cage.

35. Porn Without Unlocking

You have to watch porn for 30 minutes, no chastity unlocking, you have to just watch, no touching, no playing with yourself just complete concentration on whatever it is Madame has you watch.

36. Work it out

Today you need to do a 30-minute workout to stay in good shape for your master/mistress. Even if you are playing solo, get in a nice long workout or face a forfeit.

37. Play Blackjack

You win, you get 10 minutes out of your cage, lose and you add up the cards you lost with into hours added to your lock-up time.

38. Wax Time

It’s time to get a full wax. Watch a Youtube guide, get a wax kit, and wax your pubic hair. You may take your cage off while the waxing is happening.

Practice caution: Waxing can be painful and can cause burning if using hot wax. Always make sure you know what you’re doing before waxing.

Extra points: If you go to a waxer and have them wax you your key holder must provide you with a reward and if you’re playing solo, give yourself a single orgasm for getting it done.

39. You Look Pretty In Stockings

Dress up in stockings, panties, and a bra. You will look like such a little darling! Now you’re Madame’s little pretty play thing. Madame decides if you cum and if you cum with your cage on or off.

40. Use Edge Me Please

Now you need to go to edgemeplease, you need to set a very long duration, set the difficulty to hard, and set it to ‘I will only cum when I have earned it.’

41. Edge Part Two

Head to edgemeplease.com, but set the cum to ‘no, I will cum later’ and the difficult to ‘Impossible’, and before you start pick 10 porn videos to watch back to back while you play the game.

42. Cum Without Erection

For the next week, you can cum, but you have to have no erection and cum with a flaccid cock. Get hard while trying to cum, back in the cage, and try again tomorrow. It’s up to Madame if you are punished each time you don’t do it.

43. Panty Time

It’s an order, put some little cute pink panties on and wear them for the next 24 hours under your clothes and over your caged cock.

44. Sexy Chores

You must wear a panties, while you do any chores Madame chooses.

45. Time To See If You’re Worthy Of An Orgasm

Go to fapinstructor, set the timer to max 10 minutes, scroll down to ‘game finale‘, select ‘denied‘, and configure it to a 98% ‘probability to be denied’ and configure ‘probability of an orgasm’ to 2%.

If you cum before the end of the game, you’ve failed.

Madame picks the rewards and punishments.

46. Picture Time

Go out and take a picture of your caged cock next to 5 different plants or trees. Have fun in nature and don’t get caught.

47. Naughty Cage Picture

Today you must take a naughty picture of your cock in a cage, this could be in a public bathroom, on a walk, or in a restaurant.

48. Handjob With Sleeve On

You have 3 minutes to cum with your cock in a penis sleeve, Madame can stroke however she wants, if you are doing this solo just make sure it’s only the sleeve receiving pleasure and you don’t use the sleeve as a fleshlight or to create friction, just hand movements on the sleeve. If you don’t cum in this time, put your cage back on and try again tomorrow and again until you can do it and you are not allowed out of your cage until you achieve it.

49. Sleeve-on Handjob Extreme

Wearing a cock sleeve, set a timer for 2 minutes in which you must cum without friction against your cock if you don’t do it, every day take 30 seconds off the 2 minutes until you get to twenty seconds. You are not allowed out of your cage until you achieve it.

50. Penis Sleeve

Get a penis sleeve, and put it on over your cock cage, that’s the only way you’re allowed inside Madame for the how ever many days Madame says.

51. Two Dicks Made Me Forget

Get a realistic dildo and then give a handjob to the dildo and your uncaged man, focus on the dildo a lot more, and maybe when your man is about to cum, stop and just focus all your energy on the dildo.

52. One Day Off

You get a day off from wearing your cage, you can’t cum or touch your cock for anything other than hygiene reasons.

53. Only Use Your Ass For Pleasure

You’re only allowed to get off using your ass for how ever many days Madame decides. It doesn’t matter if you’re caged or not, your butt is the only way you get off.

54. Premature Ejaculation Check

No one wants a quick cummer, you’re locked up till you can last for more than 10 minutes during a handjob. Even when you do complete this challenge it’s back into the cage you go.

55. Premature Ejaculation Part 2

You’re locked up till you can last 10 minutes with a fleshlight. Either use it on yourself or have Madame use it on you.

56. Premature Ejaculation Extreme

You’re locked up till you can last 15 minutes of sex, once you can last that long with constant pleasure, you’re allowed to be released from your cage, as long as it doesn’t get in the way of your locked-up days that are left when you start. If you are not allowed vagina or mouth privileges or don’t have Madame use a vagina masturbator instead.

For the sex, you have to do all the work, Madame can just lay and enjoy, if the thrusts stop or don’t meet the speed Madame wants, you get locked back up and still fail.

57. Get Yourself Wet

Today you must not cum, but you must tease yourself in your cage to the point you produce enough precum that it feels like you’re wet.

58. Leave it up to the masses

Post a poll to BlueSky, Mastodon, Twitter, Facebook whatever to let everyone else decide your fate. Madame gets to decide what the poll is all about

  • Is it the amount of time to add?
  • Is it a few of the challenges from this list?

59. Shave It All

Shave your armpits, your cock, your ass, legs, everything. I want all hair gone from your body.

60. Create A Caged BlueSky

Create yourself a faceless BlueSky account to post your slutty cage pictures on. No face. Just updates of your locked-up self. Add 10 minutes for every like & 30 minutes for every repost.

61. You can cum but the cage stays on

You have to cum without removing the cage. Can be prostate orgasm or cock orgasm, but it’s gotta happen and that cage is going nowhere.

62. Strap On Fun

While he is caged have him wear a strap-on, fuck, suck, and play with the strap-on just like you would with a real man. You must fuck Madame as well as you can, understanding there’s no release for you.

If Madame doesn’t orgasm, you have to add another day to your caged time.

63. No Hand Orgasm

Cum without using your hands, you can thrust against stuff but your hands must not be used. You have 3 minutes to cum, fail and you add another 3 days onto your chastity time with no orgasm release.

64. Dildo Training

It’s now time to take a dildo up your ass, you can not remove your chastity. If you can cum from anal only – lucky you.