MaggieRaeX's Diaper Dares

[MaggieRaeX]

If you're into diaper dares (you're looking at this thread so your probably do), you're probably aware of some of my other work. Well, I've got more where those came from, written as part of PMs and dare exchanges that I've had with different people. I figure, if people enjoy reading through them (or even doing them if they're crazy enough), then I should put them all out there for people to enjoy.

As I write new ones in the future, I'll add them to this thread so that it can be sort of a running compilation of my work. I may add them on a delay though, so that the people I make them for get the first crack at "enjoying" them.

If you like what you read--let me know! Post in the thread, send me a PM, it's really nice to know you're appreciated. If you feel like you can match me, let me know that too and we can set up a dare exchange--that's where most of these come from!

Mods, if this is improper, please let me know and scrap this thread. I will be posting a number of times in sequence, just because the dares tend to be so large and limiting them to individual posts seems logical. Otherwise, everyone enjoy~

(All this said, enjoy these dares safely and responsibly--know your limits, and be safe while playing. If something seems unsafe, don't do it!)

[MaggieRaeX]

Your challenge will be one in five parts, with not part particularly fun or easy. Yet, you should endeavor to do your best on each part of your challenge, for they will be graded, and for each part of the challenge that you fail, the punishment you will ultimately undergo at the end of this challenge will get increasingly unpleasant. Really then, it’s up to you if at the end of this challenge you are in a state of only mild discomfort and unpleasantness, or in tears and abject revulsion. I know which one I’m rooting for. Good luck though~

Now, you’ll be getting points throughout all the parts of your challenge—since you’ve read enough of my work, you can probably surmise that points are bad. You’re inevitably going to get some of them, but I’d really try to keep them to a minimum, or you will be subject to an even greater punishment come the end of the challenge, and again since you’ve read my work, you know you REALLY don’t want to incur whatever that is. Be aware, that you will be on a timer from when you start the first part of your challenge to when the fifth is complete—this timer does not stop for anything, so once you start I recommend trying to power through all your challenges as quick as possible, or you’re going to find yourself racking up far more points that you want to.

You’re going to need a few things to complete your challenges, and I definitely recommend stocking up before hand—you don’t want to have to be running to the store while you’re on the clock, every second counts! You’ll obviously need a number of diapers, duct tape, baby food in every color of the rainbow, some glycerin suppositories (the solid kind), some diuretics (I suggest Diurex—often found in the feminine health section), a bottle of fiber powder (something like Metamucil), prune juice, milk, soda (must be caffeinated), coffee, (also caffeinated), you’re definitely going to need some rope, something to use as a blindfold, some kind of tarp or drop cloth (you can get super cheap disposable ones at Lowes or Home Depot), a bib (just one from the baby’s section at any store), baby bottles (you can get a pack of 12 for about 13 bucks at Walmart, you’re going to need 10 of them, so whatever is cheapest for you), a pack of balloons, and that’s just for starters—I’ll be sure to make more lists for you as you go, be sure to read all the challenges carefully and plan ahead. Getting nervous yet?

So, for your challenges… We’re going to put you through the paces of being a big baby, whether that’s what you think you are or not! You’re going to go through challenges of Wetting, Messing, Eating, Playing, and Napping—you know, pretty much everything that babies do. This will be a test of endurance, dexterity, resourcefulness, shamelessness, and pretty much how quickly we can shred every ounce of dignity you’ve got! Now you’re really getting nervous~ *wink*

Before you get started though… You need to perform some preparations the day before. You may not use the toilet to defecate within 24 hours of starting your challenge. Period. If something comes up and you need to, then you need to push everything back and wait your full 24 hours. You may not use the toilet at all on the day you’re to start your challenges, and the day starts at midnight. You’re going to need your strength for the next day, so you’re going to need to eat up! Make sure you eat a whole block of cheese over the course of the day, two bowls of bran cereal over the day, and be sure to go out for dinner the night before—McDonalds, Burger King, whichever of those fast food places does it for you, but you need to get down about a double quarter pounder and a large fry’s worth. I believe in you. Also, take a dose of your fiber powder three times over the course of the day—I recommend spacing them out, but I leave that to you.

For your challenge, there are going to be some ground rules—breaking those rules will earn you points (which trust me, you want to avoid): If your diaper leaks during the challenge, you immediately earn two points—this can happen multiple times. If you clean up at any point before completing the challenge, you earn two points—this includes wiping off your face at all. If you take a shower before completing the challenge, you gain two points—you can earn points for both this and cleaning up at the same time (so a shower is essentially worth 4 points). At the end of the challenge, you earn one point for each full hour it took you to complete it—remember, this time does not stop for anything.

So, that brings us to Challenge Day! 30 minutes before you begin your first challenge, take two of the Diurex, drink three big glasses of water, diaper up (you may wear as many as you’d like), and get everything you need to prepared for your upcoming ordeal…

Challenge 1: Wetting

As you’re getting ready to start your first challenge, you may already need to pee—between the water, the Diurex, and not peeing all day so far, could be catching up to you—since this is a “like” for you though, I’m going to assume you’ve got some staying power, so I believe in you. The objective of your first challenge is simple enough (simple is probably not the right word to use here…)—finish all the objectives before you wet your diaper. What are your objectives, you ask? Before this challenge begins, you need to fill 10 baby bottles with various liquids—three full of prune juice, three full of soda, three full of warm milk, and one full of cooled down, room temperature coffee (yummy). If you can finish all 10 bottles before you wet yourself, you’ve won your first challenge, and saved yourself some grief later! Once you’ve won, you can go ahead and wet yourself without penalty—in fact, I insist on it. Otherwise, you’ve lost your first challenge and gained one point for each bottle you haven’t finished yet, and this will definitely come back to haunt you. Oh, and you definitely need to finish all 10 bottles before you move on. We’re not wasteful…

Interlude 1

Once you’ve finished up your first challenge (win or lose) and wet yourself, go ahead and strip off that wet diaper—don’t mangle it taking it off, and just put it aside, I’m sure we’ll see it again later. I recommend wetting in that diaper as much as possible, because this is going to be the last time you get a change for a while. You have been warned. Once you’re ready, you can set your eyes forward to your next challenge…

Challenge 2: Messing

Now, I know you don’t like messing, but unfortunately little babies don’t have a choice in the matter… It’s just something they do. To be nice here, though, I’m going to give you the choice in how hard this is going to be. You’re going to be taking a couple suppositories here—it’s up to you exactly how many. You may insert as few as one, or as many as five—if you choose one, you need to avoid messing for 90 minutes before claiming victory on this challenge. If you choose two, you need to hold for 75 minutes, three you need to hold for 60 minutes, four you need to hold for 45, and finally 5 you only need to hold for 30. Now, since I know how you don’t like boring dares (and I certainly wouldn’t want you to get bored—that’s the last thing I want), we’re going to go ahead and spice things up while you’re doing your holding, and nothing spices quite like exercise! Every 10 minutes, you need to roll a six-sided die, multiply the result by 10, and do that many Jumping Jacks or Squats—it’s up to you which to do first, but you need to alternate every time. Just try not to get too distracted, because you’ve probably got quite a bit to hold. If, at the end of your time you haven’t messed your diaper, then congrats, you’ve won this challenge (and trust me, you really want to win this one…)! If, by the end of your time, you have messed however… Well, my recommendation is don’t mess… But if you did, you lose, and you get one point for every 10 minutes you had left (minimum of one point). Regardless if you won or lost, at the end go ahead and mess anyway—like I told you, babies don’t have a choice… And I’m sorry, but you get to wear this for a while.

Interlude 2

Sorry if you thought you were going to get another change here… Not so much, you’re going to be wearing that diaper for a while. You’re welcome, though, to put another diaper or two over the top of it—I know you don’t want to accidentily leak and net yourself some more points—they’re probably already starting to add up as it is. Anyway, I hope you’re hungry, because your next challenge is—

Challenge 3: Eating

Okay, you’re actually probably not going to be doing that much eating in this challenge (unless you’re really Really hungry). What you’re going to need for this challenge is six flavors of baby food: Strained Peas, Prunes, Squash, Green Beans, and Carrots, and you’ll need two of each (which is usually how they come packaged together as it is). You’re also going to need your bib, your blindfold and six letters… What the hell do I mean by that? This is actually a little tough for even me to explain—you’re going to need six little bits of something with the letters M, A, G, G, I, and E on them. These bits should be indistinguishable to the touch, so no raised letter, different shapes, or any of that. I envision little plastic circles or squares or something, and you can take a sharpie to them to write all the letters on them. We can work on exactly what you can use for this. Once you’ve got your letters and your baby food, go ahead and toss down your plastic drop cloth (or tarp, whatever) wherever you’re going to be doing this. Now, each flavor of baby food is going to get its own bowl, and into each of those bowls you’re going to put one of your letters. You may watch which bowl gets which letter, but you may not taste any of the food at this point (smell works though). Once each flavor of food has its own bowl and own letter, put on your bib and blindfold, grab one of the bowls and dump it onto the drop cloth (don’t be reckless here—you should aim to make relatively neat little piles, and be sure that the letter comes out with the food. You may not look at which food you’re dumping where. Once all the food is out on neat little piles on the drop cloth, get down on your hands and knees and get to work—from this point on, you may not use your hands at all. You must go to each of the piles (still blindfolded), pull the letter out with your mouth, and spell my name. Now, you’re going to need to do this whole thing by taste and smell—you’ll know which letters are in what flavor of food, so all you’ll need to do is fish them out in the right order and arrange them correctly.

This challenge ends when you remove your blindfold for any reason. At that point, check to see if you’ve got my name spelled correctly, from left to right. If all the letters are there and in order, you win, good for you! If they’re all there, but not in the right order… well you lose this one and you get a point. If, when you remove your blindfold, you have not fished out all the letters yet, not only do you lose, but you get three points per letter you have yet to find. If you’re going to fail this, at least make sure you get all the letters first.

Whatever the outcome, once you’ve finished this challenge, grab a bowl and scrape as much of the baby food from the drop cloth into it as you can—you can go ahead and mix all the flavors together at this point. Put this bowl aside (I recommend tossing it in the fridge, if you have the opportunity to do so).

Once you’ve finished all of this, go ahead and snap a picture of you in your messy diaper and your messy face and bib—be sure to get all of you in the shot. You don’t have to send anyone this picture, but I just want you to have a keepsake of this moment, one for your memory book~ ^_^

Interlude 3

I’m sure you’re a little messy right now, but remember—no cleaning up, unless you want another pile of points, and I’m reaaaaally pretty sure you don’t. Just going to have to stick it out at this point and get the rest of your challenges done as quickly as possible.

Challenge 4: Playing

I know at this point you could probably use a little bit of fun, so I’ll do my best to accommodate you. You’re definitely going to want to have the place to yourself for this one, because it’s going to make a bit of noise. Go ahead and grab your bag of balloons and blow up 20 of them—get them good and full. Once you’ve got them all blown up, spread them about your room (or wherever else you’re doing this challenge). Now, lube up the biggest toy you’ve got, reach down the back of your diaper, and shove it up your ass. If (and be honest here) it isn’t against you limits, lube your toy with menthol gel, icy hot, or toothpaste instead (and be sure to put a condom or two on the two first to avoid any damage to it). I leave it purely to your discretion whether or not you do this, but if you do, you can wipe three points off your total—I think that’s a fair trade if I do say so myself. Once your toy is in, grab two lengths of rope and your left wrist to your left ankle, and your right wrist to your right ankle. Make sure there’s no more than a foot or two of slack in each rope. At this point, I think you’ve got a pretty decent idea of what you’re doing here—your goal is to pop all of the balloons. You may NOT use your hands for any purpose—even to hold yourself up. You must pop all of the balloons with your butt, and your butt only. Finally, you’re only going to have so much time to get this done… Before you start, set your timer for 10 minutes—this gives you 30 seconds per balloon, which I think is completely fair. If every balloon has been popped before your time expires, you’ve won this challenge (now wasn’t that fun?)! If you still have balloons left when you run out of time, you’ve lost this challenge and earned a point per unpopped balloon. At least at this point you can look forward to the fact that you’re coming to the end…

Interlude 4

You should still have your toy in you at this point—it will stay in for your next challenge. Now, if you won Challenge #2, then you’re going to keep your diaper on at this point… I know, I know, that doesn’t seem fair at all, does it? If you lost Challenge #2 however, you’re going to change your diaper and put your messy one aside—remember, no cleaning up. Regardless if you won or lost Challenge #2, grab your first diaper (the one you wet in Challenge #1) and prepare for your final challenge.

Challenge 5: Naptime

Okay, to be fair here, I’m guessing you’re not going to be doing a lot of sleeping here, but Babies need their naptime or else they get cranky, and I don’t want to deal with you cranky. Before you begin this challenge, set a timer for one hour—that’s about how long your naptime is going to last. Take the wet diaper from Challenge #1 and strap it tightly over your head—it should be blocking all vision your vision. If you failed Challenge #2, you’ll be using your messy diaper as a pillow for this hour—you can fold it over if you like, there’s no requirement for you to spend the time in your mess (you’ve been watching your points, right?), but your head needs to be on it the whole time. Once you’re in position, start your timer. Now you just get to lay here and think about how far you’ve come and where you’re going… You have an hour to think about this. Your objective in this challenge is to stop the timer as close to 0 as you can without letting it expire. If, when you stop the timer (or remove your diaper-blindfold, which also ends the challenge) you have fewer than five minutes left on the timer, then you win! If you stop the timer and it has more than five minutes left on it, you get one point for each minute over five still left on it and you lose the challenge. If, however, your timer goes off before you stop it, not only to you lose the challenge but you gain a full 10 points. I would advise against this.

Challenge End

You’ve made it to the end of the challenge proper—I certainly hope you managed to win some (or all) of the challenges leading up to this point, because if you didn’t, your final punishment…. Well, it’s not going to be very fun—not that it will be regardless. Also, you need to total up your points at this point—if your total exceeds 20, then I’m afraid your final punishment is going to be truly revolting… I hope for your sake you’ve managed to avoid this.

Final Punishment

So now we’ve come to this point, it’s time for your final punishment. Depending on how you did on your challenges up to this point, it might be just unpleasant, or it might be about the most terrible dare you’ve ever done—we’ll see!

Since this is your first punishment from me, I thought we’d go back to a time honored classic—some good old fashioned corner time. Okay, it’s actually neither good, nor old fashioned, and it’s actually not even corner time if were being technical about it…

First, the big question—did you manage to accumulate fewer than 21 points? If so, you can breathe a sigh of relief and skip to the extra punishments (you’re still not getting out of this unscathed). Trust me, you’ll be glad you did. If not... I’m so sorry, but you need to read on. Put the messy diaper you have from Challenge #2 aside—you’re going to be using it very shortly. If you’re currently wearing it, then change out of it into the wet diaper from Challenge #1 (be sure to hold it on with a few good wraps of duct tape—we don’t want it falling off).

Now, here are the extra punishments in case if failed any of the previous challenges:

If you failed Challenge #1: You will do all your corner time wearing your wet diaper strapped tightly onto your head, your face in the crotch (give it a couple wraps of duct tape for good measure)—if your point total exceeded 20, you’re going to be wearing your wet diaper normally instead. In this case, give yourself a two quart ice water enema before you start your corner time.

If you failed Challenge #2: You must hold a lathered bar of soap in your mouth for the full duration of your corner time.

If you failed Challenge #3: You must coat your entire head—hair, face, everywhere—in the leftover baby food from Challenge #3. Be sure to rub it in good. Be sure to get some up both your nostrils, and to coat the insides of your cheeks and the roof of your mouth. If you won Challenge #3, dump the leftover baby food down the front of your diaper instead.

If you failed Challenge #4: You must get a big glob of icy hot on your hand and edge once before you begin your corner time

If you failed Challenge #5: The duration of your corner time is doubled, from 45 minutes to an hour and a half.

Now, here are the rules for your corner time—the base duration for your corner time is 45 minutes. If you failed Challenge #5, it is 90 minutes instead. Once you’ve set your timer, get everything ready and squat down in front of a wall, legs spread wide with each knee touching the wall. Both your nose and your lips must be touching the wall at all times (if you’ve got soap in your mouth, then at least your nose must still be touching, if you’ve got a diaper on your face, you need to be pressing it into the wall). Your hands must be on your head the entire time, palms flat on top of your head, fingers interlaced. If you are forced to stand up at any time during your corner time, you must completely reset the timer and start from the beginning. If you accumulated more than 20 points over the course of the challenge, then you will do the entire duration of your corner time with your messy diaper strapped securely over your face. This is cumulative with all the other extra punishments (so if you don’t want to find out what it’s like to wear a messy diaper on your face while holding a bar of soap in your mouth, I’d try to do well on your challenges!).

If you end up having to do your punishment corner time on a different day from when you did your challenge, then you must spend the night sleeping in your messy diaper, with the wet diaper on your face.

As I said, I really hope you managed to succeed a few of your challenges, and kept your points down, or you’re in for an experience…

[MaggieRaeX]

Okay, I’m going to go ahead and get you started here, and get you started off slow (for me anyway). This doesn’t mean that this challenge will be easy—I don’t give easy challenges. Hell, depending on who you ask, I don’t even give possible challenges—though, I personally just think that’s quitter talk. So, this won’t be easy, probably not going to be fun either, but if you carry it through to its conclusion and provide proof that you did so, you can move on to bigger and better things (that are harder and less fun)!

Since I don’t have a complete grasp of your schedule yet, I’ll let you decide when you need to get this done—suffice to say that you need to set out about 5-6 hours to finish. First, though, you’re going to need some things:

Diapers—however many you feel you’ll need
Plenty of water
Two 2-Liter bottles of pop—the more caffeine the better
Fiber Powder (Metamucil or similar)
Ex-Lax, maximum strength
A bar of soap
A ping-pong ball
Saran Wrap
Duct Tape

So the first thing we’re going to find out here is what kind of control you have—it’s an important thing for me to know in case you do end up getting more challenges from me in the future. This challenge will start, like many of mine do, the day before—you will take three doses of the fiber powder throughout the day and will not skimp on food—I recommend fast food or pizza in the evening, something particularly greasy. You may urinate in the toilet the day before, but you may not defecate until the challenge is over. The night before your challenge, you need to take a double dose of the Ex-Lax before you go to bed.

The day of your challenge, you need to put aside a five hour block of time to complete your challenge. At the beginning of your five hours, you need to diaper up—as many as you think you’ll need—and drink a large glass (full drinking glass) of your pop. From now on, over the course of each hour you’ll need to consume three full drinking glasses of water and another full drinking glass of pop at the top of each hour. That’s it—simple enough, right? You just have to make it five hours.

Still, what’s a challenge without rules? Rules make things interesting… And what makes rules interesting? Well consequences make rules interesting. For this challenge, there are three rules, with three consequences:

Rule 1: No Wetting—you have to make it 5 hours without wetting yourself. If you do wet yourself, then I’m afraid you’ll have earned your first punishment. Lather up your bar of soap really good in the sink, get your ping-pong ball, and go to the corner. Set a timer for one hour—for the next hour, you must squat (not kneel—squat, with your knees spread as wide as you can) in the corner, with your hands on top of your head, holding the bar of soap firmly in your mouth, pressing the ping-pong ball to the wall with your nose. If you let the ping-pong ball drop, then you must reset the timer back to an hour and start over. While in the corner, you no longer need to drink your hourly water or pop.

Rule 2: No Messing—you need to make it the same 5 hours without messing either. If you do mess yourself, immediately remove your diaper, turn it around backwards and put it back on, binding it on with duct tape. After this, you must rub yourself through the diaper until you orgasm. If you mess yourself while in the corner, then you may pause your timer while you complete this punishment, starting back from where you were when you finish this punishment.

Rule 3: No Leaking—this is the big one, you’re to avoid leaking throughout the five hours, and any punishments you may accrue. If you leak during this challenge, you need to take saran wrap and wrap up your entire package tightly, covering the saran wrap with duct tape. You must wear this wrapped package until your roomates’ return would force you to end (giving yourself an hour before they would return to cut yourself out and clean up). During this time, each time you wet you must continue to drink your water, and must continue to drink your pop as long as it lasts. Each time you wet, you must carry out the punishment from Rule 1, though instead of an hour, each time after the first you’ll only need to complete 15 minutes of corner time. This must seem like quite the punishment, but it’s also the most avoidable (if you try anyway).

Over the course of this challenge, you should keep a log of what happens throughout—times when you fail, if you have to restart a punishment, anything like that. Keep it in a .txt file and send it to me, along with whatever pictures you take throughout the challenge, and the end of the challenge.

If you have any questions, let me know, and good luck~ ^_^

[MaggieRaeX]

Unless you manage to turn this around, you’re going to owe me a severe punishment dare, so this is going to be less challenge and more just unpleasant suffering. I just know you’re looking forward to it. Since you don’t have time or living condition limitations, I’m planning for a week long affair—something small for the five weekdays, with the real, gruesome actual punishment coming on the weekend, Saturday and Sunday.

First off, you’re going to need some things for this… Obviously, you’re going to need diapers—at least 8 of them. You’re going to need duct tape and saran wrap. You’re going to need laxatives—castor oil, suppositories, fiber powder, and a maximum strength oral laxative (Max Strength Ex-Lax is my go-to of choice). You will need a diuretic—a box of Diurex (if you’re stateside) will do nicely. You will need a battery of interesting foods and beverages: one large box Bran cereal, one 1lb block of cheese, two full sized frozen pizzas, 2 64oz bottles of prune juice, one loaf of white bread, a 12 pack of canned soda (may not be caffeine free), a box of whole wheat spaghetti, and a large bag of frozen peas. You’ll also need some other things for the actual punishment, but that’ll be a in a separate list.

Now, I know that list above is pretty big, but the first part of your punishment is going to be spread out over 5 days, so think of that list as more of your week long shopping list than anything. Without further ado, let’s get started!

A couple simple rules will be in effect for the week leading up to your punishment weekend (to be fair, this whole thing is going to be a punishment week—you said you didn’t have time issues).

First rule: You will be diapered at all times, and the toilet is strictly off limits.

Second rule: For Monday through Friday, you have five diapers to get you through, you can decide when you want to change, so long as you stay diapered for the whole five days. When you do change, you must carefully remove your diaper, roll it neatly up, and seal it with a small bit of duct tape (just enough to keep it rolled up). Each time you do this, take a marker and number the diaper on the tape (so the first one would be diaper 1, the second 2, etc). If your bed has a headboard, these diapers must be placed on it until your punishment weekend. If not a headboard, then a night stand closest to your bed, if not that then a desk closest to your bed, etc—basically, store them as close to your bed as possible in a place they won’t get in the way. By the time your week is over, all five should be sitting there (or four anyway, you’ll be wearing the fifth).

Third rule: You must either use or consume everything on the following list by 11:59PM Friday night:
• One box of bran cereal
• One 1lb block of cheese
• One 1lb box of whole wheat spaghetti
• Two full sized frozen pizzas
• One loaf of white bread
• Two 64oz bottles of prune juice
• 12 12oz cans of soda (may not be caffeine free)
• 3 Gallons of water (I recommend filling some empty milk jugs—easier to keep track)
• 8oz of Castor Oil
• 4 doses of Extra Strength Ex Lax
• 4 Suppositories
• 6 tablespoons of Fiber Powder (such as Metamucil)
• 10 Diurex tablets (or other diuretic tablet)
As long as everything on the list gets consumed, you can divide it up however you want—I leave that to you, and any strategy you may concoct.

Fourth Rule: At least two times during the week, you need to go out to eat at a fast food place. Be sure to order the greasiest, most gastric distress causing thing on the menu. You must eat in the dining room. Before eating, be sure to flash your diaper to the room (as subtly as you wish), as per your HUMILIATION PM dare. Further, any time you’re out doing errands or what have you during the week, you must flash your diaper in the same way wherever you go.

Fifth Rule: While you’re home, you may not wear pants, and you may not walk—you must crawl everywhere. You may stand if you need to reach something high, but otherwise hands and knees.

Sounds like a pretty fun week, right? You’ve eaten a ton of fun stuff and you’ve got your four diapers sitting in your room (probably smelling pretty great I might add), and it’s Friday night—the big day is tomorrow!

So what are you going to need for your big day? Well, you’re going to need three diapers (slits cut in two of the three for draining), you’re going to need some kitty litter, you’ve already got your saran wrap and duct tape, you’re going to need some baby food (as much as you think you’ll need, all different flavors—no doubling up—it’s all you get to eat this weekend), a large bowl, some baby bottles filled with water, a good sized elastic band (you’ll see what I mean by this in a bit), a bar of soap, as well as some of those laxatives and diuretics that I know you’ll have left over. You’re also going to need your marker and some slips of paper…

First though, you need to prepare your elastic band. You can get elastic in any fabric store, or department store with a fabric/sewing department. Once you have it, you need to tie a piece around your head so that it’s a little snug but not tight (so a loop under your nose and around your head—it shouldn’t be falling off)—double knotted so that it’ll stay a loop when you remove it from your head.

Now you’re going to prepare your meals for the weekend… You bought as much baby food as you thought you would need, all in different flavors with no duplicates. Well, take all of them and dump them into your big bowl. Give them a couple good stirs to get them all good and mixed. Now grab what you’ve got left for castor oil and stir in the rest of that (most bottles of Castor Oil are 16 oz, so it should be about half a bottle). Get it gooooood and mixed. There, that’s your yummy food for the rest of the weekend. Go ahead and stash that in your refrigerator where it’ll be clearly and easily accessible. Go ahead and prefill your baby bottles now too—as many as you bought—you’re not going to have another chance to fill them. Go ahead and fill up a decent sized bowl of water as well and put that on the floor—that’s your reserve water, I’m sure you can lap it up if it comes to that.

That should just about do it for preparations… One last thing—take your scraps of paper and write 1 through 5 on them and put them into a hat or something similar (you’ve drawn numbers from a hat before, right?). Now, all of your preparations must be made, and your numbers into the hat by 10AM on Saturday. No exceptions. Go ahead and drink two large glasses of water and take two Diurex to get yourself primed and lay out your three diapers for the weekend on the floor. Take the kitty litter and fill inner diaper with it—you don’t have to use all of it, just get decent coverage. Take off the diaper you’re currently wearing and place it with the others—this is diaper 5. Now… Now your should be ready.
Draw the first number from your hat—this is your left foot. Take the diaper with that number, untape it, and wrap it completely around your left foot, securing it with a few wraps of duct tape. Draw your second number—this is your right foot, repeating the same process. The third number you draw is your non-dominant hand. The fourth is your dominant hand—at this point, it’ll get a little tough, so I recommend having your duct tape precut and ready to go for your dominant hand—I have faith you’ll get it wrapped. The last number, the one diaper left, will be your head. Since you’re going to need to be able to get this diaper on and off, you won’t duct tape it on (also, it would be near impossible to do so without hands). Plop the whole thing on your head—just shove your face in and get it draped over—and grab your elastic band, using it to secure the last diaper to your face (put both your hands through it, pull it open, then pull it down over your head to secure it on).

Now, the four diapers on your hands and feet are there for the entire weekend, until 8PM Sunday night. The diaper on your face remains there as long as you are not eating, drinking, or doing corner time, and is replaced immediately after finishing those activities (along with the band securing it). You may not walk for the duration of the weekend, and may not stand, except to remove your food from the fridge if necessary (and only if necessary).

Now, whenever you feel hungry, you may eat. You must crawl to the fridge, remove your face diaper, and fetch your bowl of mush from the fridge. Place the bowl on the floor—you may not eat while you are holding the bowl—and shove your face in. Eat your fill. While you’re eating, you may drink as much water as you would like, either from your baby bottles, or from the bowl on the floor. Once you’ve eaten your fill, put the bowl back in the fridge and crawl over to your bar of soap (I recommend leaving it on a chair or something at about crawling-head level). Take the soap in your mouth and crawl over to the nearest corner. You must kneel in the corner for at least a period of 15 minutes—check the time when you start so you know. You must spend at least 15 minutes in the corner holding the soap in your mouth whenever you eat—you may spend longer, that’s completely up to you—corner time is time you avoid spending with your face diaper. You may only drink water or do corner time when you eat, and you must eat at least three good bites to qualify for drinking privileges. If you eat all your food for the weekend, then you may drink at any time past that (I want you to stay safely hydrated).

The only other time during the punishment weekend that you may remove your face diaper is when you go to sleep—I don’t want you suffocating in the night.

At 8PM on Sunday, you may cut, tear, shred, or otherwise remove the diapers on your hands, feet, and face and clean up. You’re free, and your punishment is over.

I hope you “enjoyed” your ordeal…

[MaggieRaeX]

I know it’s been a while coming, so I hope this is worth the wait (and you thought I’d forgotten). I won’t lie, your limits made this a tab bit tricky, so I hope that you find this tolerable, while at the same time being exactly zero fun. With that out of the way, let’s get started!

For this dare, you’re going to need your enema bag, diuretics, plenty of diapers, some duct tape, and a spare afternoon. Before you get going, you’re going to need to perform a number of enemas to get yourself cleaned out. You should attempt to hold each for a full 20 minutes—if you expel before that, you need to take a Diurex each time. You also need to drink a glass of water for each enema you take, regardless of how long you hold it. You may not wear diapers until you are satisfied that you’re clean enough to begin (you must do at least three enemas to move past this point).

When you’re ready to start, grab a single diaper, fill your enema bag completely (get it really big and bulging full), and fill ‘er up. Your objective is to take the full bag—if you do not, if you are forced to stop early, then you must cut slits in your diaper and put on a second one over it. Whichever happens, once this is done you need to take a Diurex and drink a glass of water. Your goal is now to hold the enema for 30 minutes—if you release before then, you need to once again cut slits in your outer diaper and add another, drink another glass of water, and take another Diurex. Once you’ve expelled, you’ll have a 15 minute rest period—take this time to get your bag filled back up and ready again, because you’re not done yet—not by a long shot.

You’re going to keep this up for four hours from the time you diapered up, which means that in a perfect world, you’re going to be emptying five enemas into these diapers (and in an imperfect world, maybe more if you can’t hold them). I recommend adding in some salt to the enema solutions—I don’t want you throwing off your sodium levels with this. You should also keep some Gatorade or other sports drink around in case you need to replenish your electrolytes.

Now, we’ve got a good frame for our little game, let’s make it interesting, shall we? You list crossdressing as a like, so let’s have some fun with that. You should have a bra—I’m actually kind of hoping that you don’t, because ideally I want to you to buy a new one, and again, ideally in person. Now, I’d completely understand if this is a little outside the comfort zone, and there’s always the internet, but whatever route you take on this (have one, buy one in person, buy on online), it should be the biggest one you can possibly find. You should also get some nice pretty panties—pink, ideally, and frilly is a bonus—and makeup, good and whorish.

Now, every time you either can’t take your entire enema bag or you let your enema go early, you’re going to need to put on an article of girl’s clothing, or put on some makeup. The first time you don’t make it, put on your bra. The second time, put on your panties (move them to your outermost diaper each time you add a new one). The third time, put on some lipstick—really slather it on. The fourth time, stuff your bra cups—really get them full and make them heavy (I recommend water balloons). The fifth time is eye shadow and blush (a lipstick circle on the cheek works too). The sixth time, you’ll write “Sissy Baby Slut” across your face in lipstick. After that, if you keep failing, just keep writing “Sissy Baby Slut” on different body parts each time.

Now, you’ll be looking suitably ridiculous for all of this, let’s give you a little bit of motivation. You need to buy a baby bottle, some oatmeal, and some salt. Take a nail or something similar and gouge the nipple of the bottle some it’s got a sizeable opening. Before you start, make up a bowl of oatmeal and add in a good helping of milk—your goal here is very, very runny. Add in a heaping bit of salt and fill the bottle with the slop. Be sure you’ve got some extra as well—enough to fill the bottle two full times.

Every time you wet yourself, your next 45 minutes of free time must be spent squatting (not sitting or kneeling) with nothing but the crotch/seat of your diaper and your feet touching the ground, sucking the oatmeal slop from the baby bottle. Hands are not allowed here—put them on top of your head, and put the bottle on a chair, a desk, or the like. If you happen to wet yourself while you are still sucking on the bottle, you may not stop—either sucking, nor the dare as a whole—until you finish sucking all the slop from the bottle, including the extra.

At the end of the four hours, there will be a test. Duct tape your whole diaper package on firmly—multiple full, tight wraps around the waist and legs. Now, you have to cum. If you’ve only got one (very, Very) soggy diaper on that shouldn’t be an issue. If you’re wearing too many, then you might have problems… If you manage to cum within 30 minutes, then you’ve won—you may immediately cut yourself out of your diapers, clean up, go about your business. If you don’t manage, then you’re going to keep all that on for a little while longer—an hour to be precise, during which time you’ll stand in the corner, hands on your head, with your panties around your ankles and your diapered bottom on display. If you wet yourself during your corner time, then you must do an additional 15 minutes at the end (this is per wetting—and wetting during the extra time will result in even more time).

Regardless if you win or lose, be sure to snap a picture of yourself. Now, you don’t have pictures listed as a limit for yourself, but I understand if they are—snap one anyway. If it’s not a limit, then send it to me when you’re finished. If it is, then just take the picture (preferably with your phone) and keep it to yourself. Don’t delete it for at least another three months. No one ever needs to see it, but it’s always going to linger there at the back of your mind whenever you’re looking at pictures on your phone, and that’s enough.

I hope you have plenty of “fun” with this, and I’m sorry again for taking so long to get it to you. If you have any questions, let me know.

[MaggieRaeX]

I expect you to read this through a couple of times before we sit down to start our games, just so you can know what’s in store when you lose. This should not be fun, even for you, this is not a challenge or a game—you’ve already lost those—this is just your punishment. It has a 24 hour pre-prep window, at which point it lasts until you complete it.

24 hours before you’re due to start, you need to put on a diaper—one diaper, no layers, none of that. You must use the diaper for everything for this 24 hour period—I recommend not messing, because that could get pretty sad—you’re not going to have any choice but to wet though. If it leaks, too bad—sleep on a towel, because this diaper stays on from 8 AM the day before your dare, until 8 AM the day of.

The day before your dare, you need to gather a couple odds and ends. You need to buy a container of kitty litter—just the smallest one you can find is okay. You also need to get a 1lb block of cheese, a medium Pan pizza from one of the major pizza chains (I suggest Dominos, their pan is actually really good now), and a box of raisin bran cereal. All of this must be consumed before midnight on your prep day. You’re also going to need a spare bit of rope that you don’t care about—you’ll see why in a second. At this point, you should also prepare your ice locks. Everything else you should have. At bedtime the night before, take a double dose of oral laxatives (Ex-lax extra strength is recommended).

At 8 AM the day of your dare, you need to start getting everything laid out before you—you’re going to need five diapers, with holes poked in all the inner ones, naturally; your very largest butt plug covered from tip to base with icy hot (depending on what it’s made of, you should wrap it in a condom or two to prevent any damage to it before applying the icy hot); your container of icy hot; your roll of duct tape; 10 suppositories; your water pills; and a timer. If you don’t have bondage cuffs, you should keep a few lengths of rope around as well.

First things first—take five of your 10 suppositories and shove them up your ass. Set your timer for 1 hour, get a big handful of icy hot, and rub it deeply into your cock and balls—don’t cum or even edge at this point—this is just for a nice distraction. At this point, you just need to avoid messing as long as possible. Given that you’re full near to bursting at this point, you’re not going to be able to hold it terribly long. Once you do mess, note the time remaining of your hour—this next bit is going to last for 15 minutes, plus 2 minutes for each minute you had remaining, but you still need to keep the diaper on for the full hour, regardless of when you mess.

Once your hour is up, remove your diaper, re-set your timer for whatever you owe me from the previous section, and strap the diaper tightly onto your face. For the duration of your timer, you may not leave your hands and knees—just take this time to enjoy yourself.

Now, once your timer goes off again, that unpleasant part will be over. Remove the diaper from your face, but now you’re going to do something slightly different: Take your messy diaper and strap it onto the top of your head—it should cover all of the top of your head, and one of the tapes should be able to go under your chin to make something of a chinstrap, while the second tape wraps around your neck (not too tight or anything here, don’t go overboard). The result should have your diaper covering pretty much everything BUT your face—take your duct tape and give it several good wraps around your diaper and under your chin—when you’re all said and done, you should have a very tight and secure bonnet of sorts. You will be wearing this until the dare ends, so plan accordingly.

Now, take your second 5 suppositories and shove them up your ass, followed by your icy hot-lubed plug. Take the bit of rope that you can stand to part with, and tie a secure crotch rope with it—around the waist, then between the legs—the goal here is to hold the plug in with perfect security. Once that’s done, take your stack of five diapers and lay them out. Take this opportunity as well to freshen up the icy hot on your cock and balls, because you’re not going to see them for a while. Take your kitty litter and dump the whole thing (I hope it’s not too big of a container) into the inner most diaper, then strap them all on, one at a time until you are wearing all 5. Once they’re all on, secure the whole thing with several wraps of duct tape around the waist and between the legs—if this ever starts to sag, run some rope through the leg holes and up around the back of your neck to act as a sort of suspenders. Your punishment does not end (and you may not remove anything or clean anything up) until the outermost of the diapers is thoroughly soaked. How long that takes is up to you, but I recommend drinking large amounts of water as well as as many water pills as you feel comfortable taking.

As soon as this phase begins (while the burning is still fresh), you need to set yourself up for some bondage—you need to find a place where you can secure your wrists around a pole, support, or other sort of bar with your ice lock, tie your feet securely together, and lock yourself in. You’re in this position until the ice lock opens—just lay there and burn for me. Even after this is done, your feet stay bound for the rest of the punishment.

Once this is complete, you’re going to need to set a timer for 20 minutes. From this point on, the timer will run continuously throughout the rest of the dare (save between the hours of 9PM and 8AM, which will be your bedtime, and while you are eating). Whenever you finish a full glass of water, you may reset the timer to 20 minutes (though it immediately starts again). If at any point the timer goes off, you must reset it to 20 minutes, lather up a bar of soap, and hold it in your mouth for the 20 minutes, during which time you must be on your knees in a corner. After the 20 minutes expires, you may remove the soap, rinse your mouth out once for 10 seconds, then reset the timer for 20 minutes and start the cycle of the water over again. As I said before, you may pause the timer while eating, but for the duration of the dare you may only eat baby food, and may not use silverware.

Once again, this dare lasts until your outermost diaper is fully soaked and you begin leaking (just leaking is not enough here—the outer diaper must be visibly soaked for this to count). If you are forced by some unfortunate circumstance to end the punishment before the outermost diaper is fully soaked, then you must at your earliest convenience restart the entire punishment from the beginning—everything fresh. You may not cum at all from the moment that you lose the last of our games until this punishment is complete.

[subaddict5]

You are truly the king of diaper dares. Amazing challenged. I particularly like challenge #1. The squatting punishment is going to be hard, you really don't want a lot of punishmentpoints there. When I have an entire weekend to myself, this is one I might try!

Also like the punishment dare #5. Not sure if I could go through with it, but it is a punishment after all!

I doubt you would find your match here, even though I would certainly like to face/off in a diaper challenge match sometime. Pretty sure you would win though

[Fundareboy]

Thank you so much for sharing these with us! I am definitely looking forward to any further updates!!!

In particular I really like #1... Historically your stuff has been too amazing for me to try, but I think that this one might be one that I actually will try!

I am a little confused by one part though, You mentioned that we'd be sorry if we lost challenge #2 in the punishment, but you don't actually do anything with the messy diaper at all in the final punishment, so it seems like you actually almost want to lose it? I was just a little confused there.

But again thank you SO MUCH for your stupendous dares

[MaggieRaeX]

Originally Posted by Fundareboy

I am a little confused by one part though, You mentioned that we'd be sorry if we lost challenge #2 in the punishment, but you don't actually do anything with the messy diaper at all in the final punishment, so it seems like you actually almost want to lose it? I was just a little confused there.

As you should be confused! I remember back when I wrote this, it was broken, and the person I wrote it for was confused too, as I'd managed to leave out a couple key lines.

I've fixed it now, go ahead and give it a re-read and see if it makes more sense (though you probably know exactly what's coming with it ).

[kaliara]

As always these are mind blowingly detailed and difficult. I'll have to give one a try when I can!

[venusaphrodite]

At one point in my life, I am going to attempt one of your diaper dares. I swear.

[MaggieRaeX]

Originally Posted by venusaphrodite

At one point in my life, I am going to attempt one of your diaper dares. I swear.

I hope you do, and I hope you have fun~ ^_^

Originally Posted by kaliara

As always these are mind blowingly detailed and difficult. I'll have to give one a try when I can!

Being me, I'm going to take that as a compliment.

[Slug58]

First off all. You are definitely the king of diaper dares. But your dares needs a lot of time. You dared me at person above diaper dare thread. I would do this if i head enough time.
But can you create some dare with needs 6-10h but not less extrem?
I like the messy and humiliating parts of your dares.

[sissy 21]

i am a child still dependent on my parents so cannot buy all these and i badly want to do these please help by giving suitable dares

[sissydiaper]

can you add some more tasks I was doing them and was having fun doing them and would like to do more