More extreme diaper dares

[lovedegrading]

These dares were made for one or two people, I’ve cleaned them up and decided after reading that I’d put them up for everyone. Yes they’re not as well written or maybe exciting as other diaper dares; nonetheless I think they still might interest some people on the site as they are rather extreme (I haven’t and wouldn’t do them unless I lost a bet). Read the dares in full before you attempt them.
REMEMBER SAFETY IS IMPORTANT IF YOU FEEL ILL STOP, YOU ARE TAKING PART IN THIS OF YOUR OWN FREE WILL.


This dare will last two days, two pretty full days that is - in fact, I doubt you’ll be able to keep your eyes open towards the end and believe me that will be an issue
Day 1:

5am: On the first day you’re going to be getting up early, 5:00 am to be precise! Your first big decision is fairly simple: Will you wear one diaper or two?
Regardless of whether you pick one or two these will be your diapers (diaper) until tomorrow at 5am and will not be removed until then. You cannot go to the toilet when you wake up you must put the diapers on first and then wait until you are permitted to (both peeing and messing).
If you have opted for one diaper then the following rules apply:
- A large glass of water is to be drunk once every hour.
If you have opted for two diapers then the following rules apply:
- 2 large glasses of water are to be drunk every hour.
Unfortunately you’re not going to be allowed to pee for a while yet, not until 10:00am.
If you fail this take 3 diuretics spread throughout the day.

5am – 10am: For this 5 hour period I expect you to have gotten dressed (for the whole day), in your case this means in the most ridiculous attire you can muster; plastic panties are a must btw since you may need them.
Essentially I want you to look camp, pink, frilly and ridiculous like a sissy girl. If this isn’t possible then for being such a rubbish bore you’ll have to put 10-20% of all food from this point on into your diapers.
Aside from dressing up between 5 and 10am you will also be eating breakfast and what an appetite you’ll need for this!
You will be eating either a full English breakfast or a triple serving of oatmeal. Whilst your topping up your drink and digesting your food I would expect you to be glued to the tv watching kids shows.

10am: At 10am you are finally permitted to pee (in the diaper of course) but you should immediately drink juice or gatorade (sports drinks) afterwards. From now on you will not hold your pee, in fact you will let it go whenever you have the slightest urge.

10am -12pm: You now get 2 hours to spend how you like though you must adhere to the drinks rule and food rule (if you didn’t pass). Enjoy and remember you still cannot mess until I tell you.

12pm-1pm: You should feeling a bit tired and very bloated so coffee time...enema coffee time that it.
(If you don’t have enema equipment it’s kind of easy to make makeshift ones out of tubing, funnels, turkey basters or even just a drinks bottle). Regardless make yourself a big cup of BLACK coffee and allow it to cool then use whatever means you have to get it in. If you mess yourself in the following times (and you will mess yourself) you’ll receive the additional task:
- Less than 15 minutes: weak effort…you know what would make it weaker? Do a milk enema immediately after: 1 mug worth.
- Between 15 minutes and half an hour: sweet…drink a glass of hot water with two teaspoons of sugar in.
- Longer than half an hour: You get off free; well not really you’re in a messed diaper with 17 hours till you’re next change.

That was fun right? Well it’s gonna keep getting better because its lunch time!!!! You have a choice here a basic sandwich with whatever filling, a 6 inch sub with at least one meat and lots of dressing or sauce, a 12 inch sub with 2 different meats and loaded with sauce/dressing. Based on what you chose you get another rule:
- Sandwich: laxatives!! Take the maximum amount permissible, preferably fast acting.
- 6 inch’er: You know what else is roughly 6 inches? Bananas – insert a peeled one into your butt and keep it in there for as long as possible (have fun getting it in eww) I imagine it will come out soonish so every 4 hours put a new one in.
- 12 incher: A single marshmallow is to be added every two hours until the end of this dare.

1pm-7pm: Well I bet you’re full now (hope you remembered the food rule if it applies) and hopefully you got some new rules to keep you going. With all the pee and the mess that diaper must be reeeeaaally full, so I wouldn’t suggest moving around too much, in fact since you’re probably dressed for it I would suggest sitting down and watching some kids tv ALL DAY!!

7pm: That was mean…I bet you have irritating kids songs stuck in your head on loop and a butt full of banana or marshmallow. Well to make up for it I’m gonna let you make a feast! Between 7 and 8 o clock you are to order take away and lots of it! Now I appreciate that you probably don’t want to be seen as you are so you can cover yourself up a bit but no removing diapers.

8pm-10pm: After you’re done take a break until 10pm unfortunately during this time you cannot release your bowels, not for bananas, not for marshmallows, not for anything.

10pm-5am: Usually for dares with diapers you’re expected to go to bed early at around this time (10pm) but in your case you’re in for a horrible night. All rules remain in place, you are not to sleep under any circumstances and to help you keep awake guess what you’re gonna need? COFFEE. Repeat the coffee step at 10pm, 12pm and 5am. What with a full diaper that might be quite difficult, I concede that so here are some forfeits which aren’t much better but you might feel differently?:
- Doing only 2 of the times: insert a marshmallow every hour (added on to the ones you may already be inserting).
- Doing only one of them: Insert a single suppository at the times you have missed.
- Doing none of them…tut tut, don’t be so slippery – drink 2 tablespoons of castor oil.
Staying awake is a challenge on its own so I hope I don’t think I’ll heap on the pain anymore. Stay awake till 5am and then we can start your next day!

Day 2:
5am: Hooray you made it I expect you to have made it, in fact I’ll be seriously disappointed if you didn’t… if you didn’t there will be consequences later on.
Anyway you can now get changed but don’t throw your diaper away, store it wherever for now.
Get cleaned up and freshened up if you want because today is going to be tough…in case you haven’t noticed already the challenge is to do with sleep deprivation and control and it is not easy. From 5 am all challenges are wiped but your first task is to get diapered just as you did on the first day with the same rules.
From here on in messing is no longer allowed until I say and nor is caffeine, you can however pee when you like..

5am-3pm: Just like yesterday you will start with a hefty breakfast getting dressed in the same outfit (with the same forfeit if applicable) and kids tv, lunch will now have to be a 12 inch sub or something equivalent, and I actually want you to snack throughout the day if you can manage it…I imagine you can see where this is going.

3pm: its exercise time which in your state is probably the last thing you want to do but you have a choice as always:
- 30 press ups (or until you break): Not easy but it won’t hit you where it hurts so if you do this I expect you to do it over your used diaper before storing it again.
- 50 star jumps: Fortunately your diaper should only be damp so this won’t be much of a problem, but best to make it more interesting so add a can of beans to your diaper before doing this.
- 50 squats (or until it hurts): This will make you feel uncomfortable with all the food and drink so there are no extra rules for this…except you must now do 10 squats every hour.

3pm-5pm: After the exercise go back to watching tv/hang out/just do whatever you can to keep awake.

5pm: Early dinner, and guess what? It’s a big dinner you can either replicate what you did yesterday for dinner or you have to cook something big up, I don’t even know if you’ll have the energy to eat it…but you better because you’re so close to the finish line. After you’ve finished do w/e you want for the next two hours but stay awake and don’t mess whatever you do.

8pm: It’s time for you to get some rest…only I want you to set you alarm for 2 and a half hours later. Here’s what I’ve been building too – right now you should be exhausted, your body needs rest desperately and you should also be quite full…
You’re gonna go to bed but before you do you’re gonna insert the same amount of suppositories as 1 times whatever number you get on a dice up to 4 (so 5 and 6 =4) providing it’s not considered a dangerous amount (alternatively to improve your odds just use a rng between 1 and 4).

10:30pm: It all boils down to this then:
- You wake up with a clean diaper! Yay you can relieve yourself asap and the challenge is over.
- You wake up with a soiled diaper. Uh oh look below…
Assuming you’ve failed then your punishment is rather icky I’m afraid. Take out your previously used diaper; get changed out of your current diaper. Flip a coin:
- Heads- day 1 diaper is going to be strapped to your head.
- Tails – day 2 diaper is going to be strapped to your head.
In both cases the messiest side should be touching your face, you will need to cut a hole for your mouth and in it I recommend either taping the diaper so your mouth I not obstructed or attaching something to breathe by because your sleeping like this with whichever diaper you didn’t attach worn as it should be... after taking another suppository of course. You can only wake up at 5am or later the next morning before removing everything and getting changed.

Punishments:
- Fell asleep before you should’ve: Do the punishment above but extend 5am to 9am
- Messed when you shouldn’t have: Take a 1l enema instead of a suppository for the punishment
- Failed anything else: Find another extreme diaper dare and do it!

[lovedegrading]

Okay this is based on a really gross dare I pm’d somebody who wouldn’t stop nagging me. It is pretty disgusting and common sense is required to make it work.

You will be doing this for two days. The two days will be split into 5 sections, you’ll end up using a fair few diapers for this but the amount you use them is dependent on how well you do.
Day1:
8am-2pm: Wake up at around 8am. This first section is going to be about food…
Firstly diaper up, from now on the toilet is off limits & all waste goes in the diaper. For now dress how you want. I’m sure you want to get some breakfast to start the day, well, you’re gonna get breakfast alright. Roll a dice to see what you’re eating (DON’T SKIMP ON PORTIONS PUT OUT THE AMOUNT YOU WOULD FOR A NORMAL BREAKFAST):

1. Cereal and milk. Your choice of cereal, 1 bowl
2. French croissants with lots of jam.
3. Fruits and berries (should consist of banana, grapes, smallish fruits, etc).
4. Scrambled eggs.
5. Porridge.
6. Nothing.

Not so bad huh? 6 would suck for now though. Well at the top of every hour from now on you have to role to see if you’re gonna eat more or not, all of a sudden 6 becomes a good role because if you can’t or don’t want to eat then you have a punishment depending on what you got:

1. Put it all into you’re diaper.
2. Cocoon you’re privates in the jam filled croissant.
3. Insert them into your hole.
4. Put it all down the back of your diaper.
5. Put it all down the front of your diaper.
6. Hope your luck holds.

If you’re like me the prospect of eating loads of food isn’t too fun especially when you know you’re in diapers 24/7 so it’s assumed some of it will go in the diaper or you’ll be very full. Whatever happens you’re last roll should come at 1pm and you should take the diapers off at 2pm. Now here’s the fun part – this is going to be your left sock. Attach the diaper with your sole in the mess to your foot using a lot of duct tape and maybe cling film to prevent leakage.

2pm – 7pm: This section is all about water, once again diaper up.
Every hour you are going to play an online game – just a single game. It can be anything from chess to COD (i.e. free online games count). If you win…well done I guess. If you lose though see below for what the punishment is:

2pm: If you lose drink a large glass of water every hour from here on in.
3pm: If you lose a medium bottle of fizzy pop in the next hour.
4pm: If you lose take the maximum allowable dosage of diuretics.
5pm: If you lose add a mug of tea/coffee to what you must drink every hour.
6pm: If you lose take a 30 second stop in a cold shower with you diaper and sock on.

Before 7pm remove your diaper and attach it to your other foot to give you your other sock using the same process as last time…I hope they’re not too squishy.

7pm – 10pm: This part of the dare is a bit more sexual. Now first of all your diaper should not be put on for this instead it should be in front of you as should 2 phallic objects. The aim of the game is to avoid cumming.
Every half an hour from here on in you need to load some porn up. Then you are to flip a coin.
- Heads: you have to jerk off for the entire video, you must edge if you’re close to climaxing.
- Tails: whatever the girl/guy is doing (whoever is on the receiving end) you must also do in terms of sucking and or fucking whilst still masturbating for the entire video.
If you do orgasm it must be into the diaper and then go ahead and put it on properly. You will be sleeping in this diaper and will not remove it for any reason.

Day 2
8am -1:00pm: Rise and shine, squelch out of bed and get ready for the final key segment. It’s a baddie, which is designed to get the worst results if you struggle with control. I’ll give you an hour to get some food and drink. Before you start the next stage I’m going to make things a bit difficult for you. You will need to remove your current diaper and then wrap it around your weaker hand (which should be in a fist shape). No doubt this will be difficult as will all tasks from hereon in.

Before you re-diaper you are going to take your morning enema…enemas are always bound to get results but the outcome of this needn’t be disastrous. You must take a 2.0L enema at 9 am (if you have never had an enema before lower that to 1,0L). Once the enema is in then diaper up but:

- After 20 minutes the toilet is magically free again. You can take off you diaper and use it, this is basically the only way you can get out of the dare without messing in a diaper which goes on a body part.

After your enema is expelled remove the diaper and put it aside whilst you attach your final diaper.

Diaper up again before you do this, your enema filled (or not) diaper will be your mask I’m afraid – if you want you can cut eye/nose/mouth holes into it before securing it in place. Before you do secure it though read the final section to see if you have any other last minute arrangements.

You will remain in your current state for 1hr x a dice roll (plus 1hr x the number of punishments you incurred).

The following are punishments for weak performances:

1. If you have food in one of your socks then tie a length of rope leaving around 40cm between your ankles.
2. If you have a sock with urine in then tie a length of rope above your knees leaving around 10cm between them.
3. If you have a cum filled glove you must tie you biceps to your upper body.
4. If you have a mask with your enema in you must take another enema of 1L.
5. If you have a glove with pee in you must have your good hand down the back of your diaper at all times.
6. If you failed all of these sections take the maximum dosage of diuretics and suppositories (after you have released your enema).
7. If you failed none of them reduce your time to 1hr of being wrapped up as you are before getting changed.

[lovedegrading]

Figured i'd throw in this one, sharing is caring.

"There might be some aspects of this challenge which you’re not comfortable with/requires preparation, therefore I would suggest reading it first (though that does take out some of the fun).

The day before you start this challenge I expect you to eat heartily. You will also take powdered fibre supplement at least 3 times throughout it and the maximum permissible dosage of acquired laxatives before bed. You are not permitted to use the toilet for anything other than pee for this day and the day of the dare.

Here is the basic premise of the dare:
You will have a series of set times over 24 hours in which you must make your diaper leak. Failure will result in automatically having to fill your outer diaper to full capacity (with water) before adding a new one over the top. You will keep track of the number of times you fail (or diapers your wearing) as it will be important in the end.

Every time you’re about to leak you do a challenge (providing you are leaking naturally and not from added water).

-If you pass the challenge you get to change out of your outermost diaper into a new one

-If you fail a challenge you must add a new diaper to the top

In order to remove a diaper altogether you must succeed three times in a row. Doing so means you will remove your 2 outermost diapers and replace them with a single clean diaper.

So to the rota and the challenges, the time specified is the latest for which you must leak before accepting the forfeit:

8am: You will wake up at 8am and immediately double diaper yourself before you do anything else (including going to the toilet). There are no challenges to be had so I would enjoy your morning whilst taking on as much fluid as possible to ensure that you’re leaking before 12.

12pm: Spinning around: Write on one side of different pieces of identical paper the following:
- Fill up one bowl with pea flavoured baby food (3+ jars) and 2 max strength laxatives
- Fill up one bowl with prune juice (at least 500ml)
- Fill up one bowl with 5oz castor oil and apple juice
- Fill up one bowl with ice cream and insert two suppositories
- Fill up one bowl of water with the maximum dosage of water pills allowed.
- YAY! You have no forfeits!
Place the 6 messages in a circle of about 5m diameter. You will now blindfold yourself in the centre of the circle, spin around 30 times quickly or until you are so dizzy that you cannot stand, get on your hands and knees and move forward till you touch a note or think you can grab one. Whatever you grab you must do. Any spillage and you fail. Fail to eat/drink the selected food/liquid and you fail.

3pm: Balancing the books: The age old classic challenge of getting from A to Z whilst balancing a book on your head…with a couple of changes.
- You will be getting from A to Z and back whilst crawling. Z will be at least 10 metres away from your start position.
- You will have to balance not one but three hard back books of at least 150 pages on your head at one time. Dropping one or more at any point results in a failure.
You may reduce the number of books by 1 if you insert 2 bananas up your bottom. You may reduce it by two if you also insert 2 dice rolls worth of marshmallows. However, if you void during your crawl you fail, so think carefully before reducing the numbers.

5pm: A drinking game: Time for an old drinking game to really get things flowing. Which, assuming you haven’t already failed, may mean you need to lay some towels down.

Get a pack of cards, real or online. If you guess incorrectly for the following sections you must drink half a glass (200ml) of water before starting again. You must complete this challenge three times in a row before being released. You must attempt it at least five times (over 20 minutes) before being able to give up which is the only way to fail this challenge. Earning three fails in a row means you must consume a water pill. (Ace = 1).

State whether your first card will be red or black, draw, if correct move to the next step.
State whether the next card will be higher or lower, draw, if correct move to the next step.
State whether your next card will be of a value between the two previous cards or outside of them.

7pm: Petplay: Acting like a baby is embarrassing but acting like an animal is worse, I’m going to make you a cow for the next hour!!! Cows of course are notorious for the size of their mess so go ahead and whack in a suppository before you start.
For the next hour walking is banned. You must put socks on your hands and tie them. You are then to take a bra and stuff it full. Attach a bell (or something which makes a distinct noise) to a piece of string and hang it from your neck. You may not speak and may only moo for the hour. During this time you are to graze on weatabix (oat biscuits or w/e variation there may be) soaked in milk – and make sure that there are at least 5 biscuits in there (no hands allowed). With 10 minutes to go take two balloons and prick holes in the end then fill the balloons with milk before quickly tying and stuffing them into your bra…they will quickly begin to leak so it’s now your job to ensure that all the milk makes its way into a bucket. Any spillage and you fail. If you fail to do anything in this task then you know the forfeit.

9pm: The final challenge: A relatively simple one which I’m sure you’ll find extremely difficult. You have 10 minutes to drink 750ml of water. You must insert one final suppository. For the next 30 minutes you just have to hold on from letting go…after an entire day of intentionally flooding your diaper though with potentially adding in laxatives, suppositories, water pills etc that might not be so easy.

10pm: Count up how many diapers you have/how many times you have failed and read your punishment below:
1 – 2 diapers: Impressive. Get cleaned up and you’re free. You may ask for another dare or retaliate depending on w/e you like to dish out.
3 - 4 diapers: So close yet so far. You will sleep in your diapers and cannot remove them until 9am the following day.
5-6 diapers: The same as the above but you will not be allowed to leave your diaper in the morning until it is leaking.
7 diapers: You will sleep in the diapers , but before you do start a thread on getdare explaining your predicament asking them what you must do in order to change from your several diapers. Hopefully they’ll go easy because you can probably barely even walk."

[Luke.Mayner]

Just started this dare
Already managed to mess the diaper under 2 hours in

[25malecrossdresser]

definitely trying a modified version of this dare ASAP (:

[DLdapper]

Reserved. def. gonna try this one day c: