Daily Chastity Challenges, Dares & Games

We all like to keep things exciting and fresh in the bedroom but sometimes it can be hard to come up with unique and interesting ideas, especially when it comes to something as niche as the beauty of chastity. I had a few brainwaves whilst playing with a cock cage with my boyfriend and I figured why not share these brainwaves with my gorgeous readers?

In this article, you will find a game like no other. A game that requires no skill and all chance. However, it’s nothing like squid game (thankfully), these chastity challenges will keep you on your toes and they can be played solo or in a couple. Let me know how you get on playing it in the comments down below! Jess ❤

Safety notice: You do all of this at your own risk, you should practice common sense and understand this is a novelty game.

How To Play This Chastity Game

So, I need to teach you how to play this spine-tingling, adrenaline-inducing, exciting game and you may be pleased to know that 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 – 88, 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 as a keyholder: Just browse the below ideas and use the ones that you see fit for your caged man.

Lucky Dip: Write down 100 random numbers, shuffle and pick at random and whichever number it lands on is the dare you must complete.

No Keyholder: If you don’t have a key holder and are playing solo and you find yourself faced with a couples challenge, work your way down, to the nearest none couple challenge and begin there.

As you can see there are a few ways to play this game, I like to mix and match how we choose the dares because you never know what you’re going to get and it’s always exciting.

I must add that all challenges are fresh, but I through in some days added and days off a few times to make it a little harder along with a few challenge repeats to really test your endurance.

PSA: You must own and be using a cock cage to participate in these challenges, if you want to find the best cage check out this list of cock cages and you can learn how to fit your cage here.

The Forfeits

Once you know how you’re going to play the game it’s time to talk about forfeits.

If you don’t have the toy mentioned in one of the challenges or missing an item or it’s a challenge with a keyholder and you’re solo you have to do one of the forfeits mentioned below:

• Add punishment days (I like to do ‘no cum days) with the number you have picked. For instance, if it’s a 6, then add 6 days of punishments to your total.
• Do the challenge that is either above or below your challenge.
• Add 5 days to your lock up and pick another number.
• Use a chastity punishment mentioned on this list.

This is only applicable if the challenge is impossible to do, if you can do it but you refuse then you need to not cum for 1 week and take a week away from the challenges before you can come back and continue where you left off.

Chastity Challenges/Dares

The challenges with this symbol (^) mean they can’t be played solo and if you are alone just move on to the next challenge.

Now we know how to play and what we must do as a forfeit…

Let’s kick these games off! These are your chastity-inspired dares and challenges that I have set out for you. Good luck and have as much fun and cum as you possibly can!

Please be wearing your cock cage and if you don’t already have a time set on how long you must wear your cage. A week? A day? Two days? Make sure you do, if you’re not sure start at 24 hours, and if a challenge tells you to add on time, add it to your chosen lock-up time.

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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 a day onto your lock-up chastity time.

2. Add 2 Days On Because I Said So

Oh, you only had a day left of wearing your cage? Whoops! Add two days on because I said you have to. Hopefully, you were busting to cum, and hearing this news makes you so very sad.

3. Hide and Seek ^

This challenge cannot be played solo, please move on to the next challenge.

Your keyholder has to hide your key around your house (they get 5 minutes). You then have to decide how long you get to find it, for every minute you choose, if you don’t find it you have to add a day onto your chastity time.

Example: You decide you have 20 minutes to find the key, find the key in that time and you’re free to have an orgasm and 20 minutes out of your cage if don’t find the key in that time, it adds 20 days onto your lock-up.

You can pick just a minute if you’re scared, or hours if you’re confident.

4. Take Two Days Off

Take two days away from the challenges and keep your cage firmly on. You’re free to tease yourself or have your keyholder tease you but you must not cum in those 48 hours.

5. Go To Dice Roller

Go to this dice rolling website and whatever number you roll, add that to your chastity lock-up time. If you roll a double six, add 12 days (or hours depending on how you wear your chastity).

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 Keys

You have to put your cock cage keys 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, your keyholder can do what they like to you (or if you’re solo tease yourself). Completely render your eyes useless with a blackout blindfold that will take one of your vital senses away for a few hours.

10. Leave your cage keys at work

Stop giving yourself the option to take your cage off, leave your keys at work or in a gym locker or have your partner leave somewhere only they know. (It goes without saying please always make sure you have a spare set somewhere useful for emergency situations).

11. Pleasure Your Wife To Completion ^

You have to please your partner 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 keyholder to decide the punishment.

12. Try Not To Cum

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

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

13. What Challenge Did You Get

Tell me, every day that you play what challenge you get in the comments, I want to know. If you don’t want to post publicly send me a message through my contact form.

14. Keyholder Orgasm ^

You have to make your keyholder cum [insert a number of times] before you can cum. Not all on the same day, it can be spread out as far as long as the keyholder wants.

I usually make my boyfriend give me 10 orgasms for every ruined orgasm he has or 20 orgasms for every complete orgasm he has and he cannot cum in between those times, he has to wait until I have had my 10 or 20 orgasms.

15. Count Out 100 Grains Of Rice ^

You have to count out 100 grains of rice, do the wrong amount and you get 100 hours added to your chastity, do it right and you get nothing.

Your partner must count the rice after to make sure you got it right.

16. 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.

Limited to one orgasm a week, for 4 weeks.

17. You Must Be Tied And Tickled ^

Have your keyholder tie you up nice and securely and tickle you until they say. It’s pure torture and a really fun time for your keyholder!

18. Write The Truth

With a body-safe marker pen draw the truth on your body or if you have a keyholder have them do it. I usually write cum slut, caged cuck, small cock with an arrow to his cock, and all the shames I know my man hates (here’s a big list of bdsm writing ideas).

Extra points for ones people can see 😉

19. 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!

20. Butt Plug Clean Up

Put a butt plug in while you hoover/mop up all the floors spotlessly in your house. Make sure to get between the cracks!

21. 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.

Succeed and get a 10-minute break from your cage (however, strictly no cumming).

22. Only Pee Sitting Down

For the next month, you can only pee sitting down, absolutely no standing up to pee. It doesn’t matter if you’re in or out of your cage for this challenge.

Set a reminder on your calendar for when you can finally be allowed to stand up again to pee like a man.

23. Run Your Keyholder A Beautiful Bath

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

24. Add a pink bow to your cage

Tie a little pretty pink bow to your cage for the next 7 days. Don’t have a bow? slide some girly panties over your cage instead, also for 7 days.

25. 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.

26. Nice Long Walk

Go on a nice long walk in your cage with no underwear on, just your pants on.

27. One Free Orgasm

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

28. 30 Minutes Of Pegging

It’s time to get that ass ready for your keyholder.

Bend over and let your keyholder 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 your keyholder to decide.

If you are solo use a dildo on your ass for 30 whole straight minutes.

29. Strap On Replaces You ^

For the next two weeks (or longer if your keyholder decides so) the strap-on replaces your dick, your keyholder 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.

30. Get Pegged While Wearing Something Sexy

Your keyholder will peg you wearing whatever outfit they see fit, might be boxers, it might be a thong, might be stockings, she might ask you to wax, it’s all up to them. No keyholder? I want you to wear stockings, and panties and fuck yourself with a nice big pegging dildo.

31. Cum Window Of Time

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

I like to make my man masturbate for a solid 30 minutes (sometimes an hour) and he has to cum in the exact 2-second window I give him. If you are solo put on a 30-minute timer and in the very last two seconds you can cum, if you fail to do this, lock yourself back up as a punishment.

Once the time window is up I make sure my boyfriend stops, it doesn’t matter if he is mid-ejaculation, or if he didn’t get his release, failing to do so inflicts 7 days in his cage time and that’s me being generous, I once I added a month!

32. You Can Only Cum On Wednesday At 6 PM

Doesn’t matter about your release day, 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. I was kind to you, I usually put my man’s on days and times when I know he is busy or at work.

This continues for the next two months.

The only exception to this rule is when you’re fucking your keyholder because they want you to and even then it’s completely up to them if you did enough to deserve an orgasm. My man has never done enough to deserve release away from this window unless I pull another challenge card that gives him the chance.

33. Cum Deposit

You must cum in a jar at least 4 times, with video proof (if your keyholder is not present or you are doing this challenge alone) and the cherry on the cake is that you only have 30 minutes to do this.

Failing to do so adds a month to your time.

You should be grateful, this is more orgasms than you should ever be allowed as a locked-up slut. Don’t want the challenge? Add 5 days to your lock-up time.

34. Free Pass For Your Wife ^

This is a token for a keyholder to be able to have sex with anyone they please that isn’t the caged man. This could be their first sharing and swinging experience, a roleplay scenario with a sex toy, or even just all fantasy that she tells you about.

35. 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.

36. No Underwear

No underwear is to be worn by the cage wearer for 7 whole days and during those 7 days, the cage must be worn out of the house with no underwear on. It doesn’t matter if it’s your best friend’s wedding or a trip to the beach, no underwear and all cage.

37. 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 if you’re a keyholder and better yet have your chastity slave do it for you. If you’re playing solo add 10 random challenges from this list to your spin wheel and enjoy,

38. Which Hand? ^

Have your cage wearer pick one of your hands that are hidden behind your back, in one hand is an immense pleasure, on the other hand, are more days added to his total. Does he get the best of three? did you lie about which hand was which?

39. Slutty Outfit ^

Wear his favorite slutty outfit around the house and then out with your friends, let him see it, let him understand it’s not for him and it’s for the other people in your life.

Go out, have fun, send pictures to him as he is locked away, and enjoy your slutty sexy self.

40. Magic Wand Fun

Stimulate his little clit (cock) 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 he gets another day added to his lock-up, if he doesn’t cum he gets to have an orgasm and no days added to his total.

Feel free to tease yourself with the magic wand too!

41. 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.

42. Clean Your Bathroom With A Toothbrush

Get on your hands and knees and scrub your entire bathroom with a toothbrush. Bonus points if you are naked and wearing your cage.

43. 30 Minutes Of Pleasure

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

44. Porn Without Unlocking

You have to watch your favorite porno for 30 minutes, no chastity unlocking, you have to just watch, no touching, no playing with yourself just complete concentration on your favorite adult film.

45. Go To The Gym

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.

46. Phone Screen Wallpaper

Take a picture of your caged cock and set it as your phone background. I don’t care if you use that phone for work, get it done!

47. Use a urinal while caged

This is best to be done in a lifestyle club or if you really must bend the rules (keyholders punish as appropriate here), do this at home and any pee that doesn’t make it down the toilet bowl is to be thoroughly cleaned up.

48. 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.

49. Wax Time

It’s time to get a full wax. Watch a Youtube guide, get a wax kit, and give yourself a cock and ball wax. 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.

50. Wear An Item That Says’s Something Chastity Related

Today you need to buy or DIY an item of clothing or an accessory that says slave, caged up, or something chastity related so that passers-by and other caged sluts know exactly what you’re up to.

51. You Look Pretty In Stockings

You can cum, but only if you dress up in stockings, panties, and a bra. You will look like such a little darling!

52. You’re Only Allowed To Sit For 30 Minutes Today ^

Today is a day your legs are going to be put to good use. There are no chairs available for you to sit on and so I can only give you 30 minutes throughout the entire day to rest and if your keyholder catches you sitting down a punishment will be given to your keyholder.

53. 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.’

54. 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.

55. 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 your keyholder if you are punished each time you don’t do it.

56. 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.

57. Sexy Chores

You must wear a thong, while you do any chores your keyholder picks (or if you’re alone chores that you pick). Don’t have any chores? Then wear a thong while you work out, wear it while you make dinner, and wear it while you pretend to be a footrest for an hour.

58. Go Out All Dressed Up

It’s time for you to put a little summer dress on and go to the store. You will look so darn cute!

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

Go to fapinstructor, set the timer to max 60 minutes (or 120 minutes if you want an extra 2 days off your lock uptime), 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%.

Have your keyholder pick the rewards and failures, if you don’t have a keyholder then copy the below tasks.

Side note: If you know Reddit, you can add subreddit names to the media, and add your favorite, if not just do what they recommend, or you can copy these Sub Reddits into the media box: cuckold, sissy, chastity, hotwife, ChastityCouples, femdom, femdomgonewild, gentlefemdom. It will look something like this:

Start the game!

Fail the game, add 7 days to your cage, make it to the end of the game, orgasm release, and exit from the cage 5 days early.

If you don’t have too much lock-up time left this could mean you get let out right after the game so make sure to concentrate.

60. 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.

61. Measuring Time

It’s time to measure your hard cock, let it out of the cage to do this, and grab a measuring tape.

1 – 3 inches – Punishment: 1 hour of edging your orgasm to be put back into your cage again without release.

3 – 5 inches – Punishment: 3 minutes of intense masturbation with no orgasm release.

5 – 6 Inches – Punishment: Watch 5 porn videos in a row whilst your cock is caged up.

6 – 7.5 inches – Punishment: If you can cum in under 5 seconds you can enjoy, if not, get back into the cage, even if you’re about to cum.

8 Inches Plus – Punishment: If you can give proof and you are 8 inches plus, you get a day off from lock up, you can’t cum, but you can have a rest from your cage.

62. 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.

63. Go To A Nudist Beach In Your Cage

Go to a lifestyle nudist beach and go in just your cage, show off your little cock as it’s caged up. This is weather and location-dependent.

64. Handjob With Sleeve On

You have 3 minutes to cum with your cock in a penis sleeve, your keyholder 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.

65. 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.

66. Show A Friend Your Cage

It can be on through a picture or in real life, feel the shame. Play it off as a mistake, a joke, or however you wish but they must see you all locked away.

67. Clean-Up Duties ^

You must clean up your keyholder the second she gets home from work or once the day is over. You must use your tongue to clean and worship every part of her even before she has showered.

68. Penis Sleeve ^

Get a penis sleeve, and put it on over your cock cage, that’s the only way you’re allowed inside your keyholder for the next 2 weeks.

She gets the benefit of feeling something bigger than your small cock. Who knows, maybe this will become the norm from this point on and you won’t feel her pussy ever again?

69. Hairclip

Add a girly hair clip to your hair for the next 7 days, even if you have to wear it to work or to the store. It does not come out until the 7 days are up.

70. 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 bigger, better dildo.

71. 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.

72. Only Use Your Ass For Pleasure

You’re only allowed to get off using your ass for the next month. It doesn’t matter if you’re caged or not, your butt is the only way you get off.

73. 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.

74. Premature Ejaculation Part 2

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

75. 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 a keyholder use a vagina masturbator instead.

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

76. 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.

77. Let A Random Bull Decide Your Fate

Have a bull decide what happens next.

If you don’t have a bull in real-life use FetLife, Reddit, Twitter, or Adultfriendfinder to find someone to give out the orders.

78. Shave It All

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

79. Create A Caged Twitter

Create yourself a faceless Twitter to post your slutty cage pictures on. No face. Just updates of your locked-up self.

80. Wrap His Key Around Another Mans Cock ^

Give a guy a blowjob or handjob and put your man’s cage key on or around his cock. Even snap a photo to show to your caged man to show him how easy it is to use his key elsewhere.

81. Another Mans Cum ^

Have another man cum on his cock cage key. Get a load all over his only chance of release and make sure the key is covered!

82. Cum On Your Cock Cage

Have another man cum on your man’s cock cage or if you’re alone use fake cum to simulate another man’s juice all over your own manhood.

83. 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.

84. Clean Every Toilet You Use

Today, If you use a toilet, you have to give it a full clean, every single time.

85. 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 your keyholder as well as you can, understanding there’s no release for you.

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

86. Take a 6-inch dildo in your ass

You have to train yourself to take a 6-inch anal dildo up your butt. You’re locked up till you can get it to fit with ease.

Achieve it within a day and you get 1 day off.

These are my boyfriend’s favorite 6 inches to play with:

#1. This realistic dildo boasts a suction cup base so you or he can ride it anywhere and practically everywhere.

#2. A dildo that vibrates brings him extra pleasure that he doesn’t know what to do with. It is astonishing watching him take and shudder this one.

87. 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.

88. 8-Inch Dildo Training

It’s now time to take an 8-inch dildo up your ass, you can not remove your chastity until you can do it with ease. If you do it within a day then you get a whole day out of your cage.

These are some of my favorites:

– Taking an 8-inch dildo is no easy game but this ultra-realistic cock makes it even more enjoyable for your tight ass.

-This vibrating 8-inch cock sends shockwaves of pleasure through your body, it makes it easier to take the length of this toy and makes it harder for you not to cum.

-Lifelike, big, and well-endowed this realistic dildo will give you a much-needed challenge and pleasures the entire way down its textured shaft.

Anything You Can Do To Remove Days?

A few wrong moves and you could face weeks locked in your cock cage and so the answer is, Yes, your keyholder can set up ‘good’ rewards, so can solo players in order to remove days from their total.

You have to create a list of things that are good behavior, when you complete one you get a day off.

• Cleaning the house
• Going to the gym
• Making a special dinner for your keyholder

Whatever it is that you consider good behavior, write it down, and if you (solo players) or your keyholder decides it’s good enough to remove days then tick them off!

Add Your Own Challenges In The Comments Below

If you want me to add anything else to this list, leave them in the comments below and the best will get added. Make sure to also leave some challenges of your own for anybody looking for some cock cage side quests!

Jess ❤