Adult Diaper Punishment Stories

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Adult Diaper Punishment Stories


The Institute

Cross-Dressing Punishment and Humiliation for All

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First off, I’d like to apologize to everyone—things have been a bit hectic, and I missed my usual Sunday deadline. I hope the amusement that you get from my suffering makes up for it a bit, and trust me, there was a good bit of suffering. This week’s story assignment actually managed to be less pleasant than Back and Forth , which I didn’t even think was possible. Like Back and Forth, I was again going to be transporting pennies, though this time as a restrained maid, and before I would be able to complete a penny I would need to perform oral service on a nearby dildo. Combine that with the same 1,000 pennies from the first time I did Back and Forth (which was never going to happen), and horrible consequences for failure, and you’ve got just the latest in my hellish assignments. First order of business, though, was to get dressed…
It could have been worse. It really could have. This week’s story chapter was a little bit of a lull in the action (thankfully), and while this week’s assignment was no where near the tortures I endured last week , it was still less than pleasant. 24 hours I would need to spend in the same dress that I was in last week—24 hours gagged, in a super-stuffed diaper and heels with my largest breastforms in. It may not seem like it, but 24 hours can be a long time, especially when you’re gagged for it. Still, Mistress Katzenburg was gracious enough to allow me to avoid being locked in a closet for the full duration like my story counterpart was, so again, it could always be worse.
I was up at 6:00 AM yesterday, dressed and ready for my assignment, and 24 hours later I’m tired, I’m wet, I’m in desperate need of a shower, and I’m ready for this week’s assignment to be over. I’m just crossing my fingers that I can get off this easy for next week’s assignment as well. I can always hope, can’t I?
Let me tell you about the worst night I’ve had in a while, and bear with me because I haven’t had nearly as much sleep as I should have. This week’s story assignment looked bad on its face, many of them do, but it’s not until you’re well into it before you realize exactly how terrible it is. The principle sounds simple enough—my assignment was to transfer pennies one at a time from a cup in one room in the house to a cup in another, with increasingly unpleasant additions as I went. Now, my place isn’t that big, and even spread out as far as possible, there were only about 15 steps between cups—not awful you say, that’s 30 steps per penny. Well, allow me to show you how wrong you would be…
Like most assignments, however, I started by laying out everything I would need beforehand… Ominous, isn’t it?
Nearly a week ago, we active clients here at the Institute received a warning that a new assignment was coming down the tubes, and that it would be based on the timeless music of the Violent Femmes. While we were all asked what our two favorite Violent Femmes songs were, Mistress Katzenburg’s two favorites were ‘36-24-36’ and ‘Dance, M.F., Dance’. From that alone, I knew that nothing good could come of this assignment, but yesterday I found out just how bad it would be.
Since none of us had 24” waists, we were first to figure what our bust and hip sizes would need to be to maintain the same proportions. It turned out that I would need a 63” bust and hips, which meant a bra with my biggest forms and a super-stuffed diaper (since it seemed like it wouldn’t take too long, I omitted the diaper and just super-stuffed my plastic panties—bad choice). After I was dressed I had to make a video for Mistress Katzenburg following the directions of her second favorite song, ‘Dance, M.F., Dance’—you can imagine just about how well that went, in a bra stuffed as full as mine was. If she decides to post the video, then you’ll get to see it as well.
About a week ago, I had a spare afternoon where all my work was done and I had no other real outstanding obligations. To pass the time, I decided to work on my art (I’m not really an artist, but I like to mess around with it none the less). One thing led to another, and before I knew it, I’d finished my first picture in a long time. Wanting to share it, I posted it to Twitter, where it caught the eye of Mistress Katzenburg. Having no outstanding assignment at the time, she decided that my next assignment would be to duplicate the picture that I had drawn. Given how unpleasant the subject matter I’d drawn was, my heart sunk a little, but I pledged to finish my new assignment as quickly as possible…
A long, long time ago I was given an assignment in response to some unnecessarily mean things that I’d said. At this point, I honestly can’t remember what they were, but they more than warranted a response from Mistress Katzenburg. That assignment was the originally named, Full of Shit. I was to find a recipe that would leave me looking like I’d been covered in shit, post the recipe, then make up a large batch, dress up like a baby, and cover myself in it for the enjoyment of all of you. That assignment unfortunately never happened—life gets in the way, things get put off until later, and before you know it, it’s been five months. I should have known better than to put it off, and I’m sure I’ll pay for it in the long run, but better late than never.
Back to School. I have finished Summer School Semester # 1 and I am now about to start Semester # 2. The Session Break was too short.
This Semester is dedicated to a class curriculum of “Sissy Girl” Home Economics. It is supposed to be a learning experience of what to expect as a Sissy Girlie Cross-Dresser in preparation for readmission to “The Institute for Cross-Dressing Punishment”. This Semester looks like a lot of difficult Sissy Courses and I am already behind in starting my first course and further behind in posting my course report.
My first week course entails the experiences of a “SISSY BABY”.
The following course requirements are:
As a result of this sissy student failing to start the course on time and missing the first two class days, this first week class will be extended another week with requirements not completing until July 1.
With reluctance and trepidation, I went to my first class of Semester 2.
Sissy Summer officially started June 4 and to my dismay I was once again asked (Required) to participate. The “Girlie” Dress Code this summer was an alternating blend of Panties and Thongs every day. My weekend Dress Code remains in affect to my continuing discomfit.
I collected Panties (three) and Thongs (four) for each day of the week and laid them on the Bed for display and inspection by Mistress and then put them in my lingerie draw for use during the week.
Summer School Session # 2 – June 18, 2012 through July 15, 2012:
Week 1 – Experiences of being a Baby – Sissy Student Assignment and Requirements
Week 2 – This week will be devoted to her “period” week. Learning to become a young Lady is critical to her Sissy Development. This course is under the guidance of “Auntie Flo”. “Auntie Flo” will send her reminder and daily assignments prior to the School Week.
Week 3 – Housekeeping 101 – How a Sissy should keep Mistress’s House
Week 4 – Fashion Training – Sissy Dress-up Week
The “Institute” Mistress School Board has also reviewed sissy billy’s 1st Semester Records and while it’s review is not complete, it has been determined that since she is now on “Probation” the following shall be added to her school assignments. Her Progress is still being reviewed and it is anticipated that further disciplinary actions may be assigned.
Since she seems to be forgetful about her assignments and late in turning in several assignments, for the remainder of the summer, sissy billy is required to install a full time reminder that she is a sissy.
She is to obtain two dildos that can both be mounted on the wall. Each will be mounted 18 inches off the floor, next to the door leading to the garage (one on the inside, one on the outside). For the remainder of the summer, every time she enters (or leaves the house), she will
(1) Get on all fours
(2) Spend 15 seconds giving proper homage to the phallus
(3) Stand up and open the door
So, every time she goes through that door, she will practice her sissy oral servitude before going through the door. Her Mistresses think this will be a way to help her remember her place. Documentation of this shall be included in her first post and report.
I am once again destined to travel to Fantasy Island. Assignment # 3 is my Bonus Trip – Double Down. I still remember my first trip to the Fantasy Island Casino and I know that this trip to the Casino will not be any more fun than my first trip to the Casino.
As I departed the Ferry – I was whisked away by the Fantasy Island associate Mistresses to be prepared. Instead of a sleek Dress, this time I was being taken to a private room of High Roller Mistresses and I was to be dressed in the sleaziest Peignoir Lingerie, the largest bra and forms and a matching thong. High Heels, of course and Makeup.
I was led to a not so private Bath where the clientele could walk in and out and naturally they all did to ridicule me and humiliate me. I was stripped naked and finally was allowed to submerse my self in my Bubble Bath.
It really is humiliating taking a bubble bath in front of a lot of Casino Patrons. If only my night ended with this.
I have been silent too long and have not wanted to participate, but I have completely supported Mistress Katzenburg in her attempts to train my Sissy. However, Mistress Katzenburg and I are in agreement and are completely disgusted with your feeble attempts and poor attitude. With urging by Mistress Katzenburg, I will no longer be passive, but will take a more active Role in assiting Mistress Katzenburg and the Institute in your training and punishments.
silly billy has been lazy, arrogant at times, completely negligent of her duties as a sissy client of The Institute of Cross-Dressing Punishment and just plain naughty. She has broken and failed to follow so many “Rules of the Institute” that we could not list all of them. It is time for her attitude to change and her rehabilitation to begin.
Since sissy billy seems not to have enough will power of her own to follow even the simplest rules or demonstrate a proper attitude, I will give her a strict and rigid schedule to follow over the next three months. She will either complete successfully every assignment given her or I will wash my hands of her and I imagine Mistress Katzenburg my suspend her and put her in the Hall of Shame.
“sissy billy” – read your fate below in the following agenda that we have set for you and obey completely.
It has been a while since I have posted an update for The Institute, for a number of reasons—some good, some quite bad. When it comes down to it, I have broken one of the most important rules of The Institute: When a client will be out of town or unavailable for an extended period of time, they must notify the Mistresses of The Institute ahead of time. I did not do that, and I have been away for an extended period of time, during which I shirked my Institute duties. That was the bad part. The delightfully good part is that, over the past few months I have been developing a closer and closer relationship with a good friend of mine, which has rapidly become something far more special. While I was away from the Institute, I was instead with my new Mommy Venus (who is extremely eager to step up the intensity of my already humiliating and painful Institute activities) who made sure that my time away was not spent pleasantly…
I ask myself how I ever got myself into this mess. All I did was request a few months off to take care of some personal Business. My re-instatement has become long and trying. The Moral of this all is that all sissy clients of “The Institute for Cross-Dressing Punishment” should realize and accept that they are naughty and that this should never be a part time experience, but must be dealt with on a continual basis. I will think twice about asking for a little time off the next time. But then again, I never seem to learn quickly. However, back to the task at hand.
I am restarting my assigned trips to Fantasy Island. This time the script is dictated by other clients and Mistress Katzenburg.
As I approach the Mistress of Fantasy Island she informs me that she wants to go to the Fantasy Island Casino and will teach me to be a High Roller. I am whisked off by her assistants to dress for the occasion.
I am to wear a slinky dress, a large bra and forms and a matching thong. I present myself to the Mistress.
I have spent more time in this outfit than I care to think about: Eight Legged Clean Freaks , In a Row , the first It’s a Maid, Maid, Maid World … This is not a pleasant outfit, especially when the super-stuffed diaper must be messy before any cleaning can actually take place. I am desperately hoping that this is the last time I have to endure this assignment—I’ll take anything else if it means not having to do this again.
Functionally, this assignment was identical to the three that came before it—get dressed up, clean apartment, submit evidence along the way and at the end, proving that apartment is indeed clean. As this was a punishment for doing poorly on my previous assignment, however, new elements are restrictions were put in place to make the assignment even more difficult. First, my wrist cuffs had to be clipped together (which makes for extremely difficult cleaning) and my ankles had to be bound together on a short chain or rope. When you combine the ankle bondage with the super-stuffed diaper, all sorts of misery ensues, just from how you’re forced to walk. I hope this is the last time those two things ever make an appearance in the same assignment. Additionally, I had to mess my diaper before I started, and I wasn’t allowed a change until I finished—I haven’t finished by the way, so four hours later I’m still sitting in the same messy diaper, can I be done yet?
This assignment had a second big twist compared to the first three that merits mention: Instead of simply taking pictures to prove that I’d successfully cleaned, I was to star in a short movie where I present my work to Mistress Katzenburg. She has said that the movie may or may not be posted at a later date, so that remains to be seen. It’s fairly long, considering, and it may end up posing bandwidth issues, so we’ll see.
I would definitely like for this to be the last time I have to deal with this assignment, if nothing else so that I can move on to bigger and better things, regardless of what those end up being. I have finished it, however, and that’s a big monkey off my back, considering all the hang-ups and snags that preceded it getting done. It’s nice to finally put it in the books.
As usual I could not make up my mind as I walked up to the Mistress of Fantasy Island. My mind, however, was made up for me quickly by the Mistress.
She asked if me if I remembered my Fantasy Island Wish about joining a Sorority. I, of course, nodded yes. Well then, she said, it is time for your Sorority Pledge Hell Weekend. I shuttered having read many articles of what they did to Sorority Girls during Hell Week. I was quickly dragged by the Fantasy Island Assistants to the Dressing Room and returned to Mistress after an hour of Sorority Girl prepping.
She complimented me about how I looked like the perfect Sorority Pledge and took my hand leading me to the Sorority House.
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Who has some embarrassing diaper stories?
✨Moi has experienced many horrible things and lovely ones✨ · · 1 y ·
Has anyone’s diaper been changed by your classmate or your sister or girlfriend as a teenager?
Has your parent ever diapered you as a teenager?
Have you ever been forced by your babysitter to wear a diaper as a teen?
What are some embarrassing diaper punishments?
Were you ever forced to wear a diaper when you were a teenager?
Author has 462 answers and 745K answer views · May 9 ·
Has anyone’s diaper been changed by your classmate or your sister or girlfriend as a teenager?
Has your parent ever diapered you as a teenager?
Have you ever been forced by your babysitter to wear a diaper as a teen?
What are some embarrassing diaper punishments?
Were you ever forced to wear a diaper when you were a teenager?
What is the most embarrassing diaper experience with a babysitter as a teen?
Have you ever worn a dirty diaper in public as a punishment?
Have you ever been caught being diapered in public or at a friend's house? If so, what happened?
Have you ever been diapered, or put into a diaper, during a sleepover?
Have you ever been put in diapers against your will?
Has anyone ever been put in a diaper at boarding school before?
Have you ever seen older kids being diapered? If so, what happened?
Girls, have u ever been caught wearing diapers?
Have you ever been diapered by someone else's mom?
Were you ever caught using a diaper at a sleepover when you were a teen or adult?
Has anyone’s diaper been changed by your classmate or your sister or girlfriend as a teenager?
Has your parent ever diapered you as a teenager?
Have you ever been forced by your babysitter to wear a diaper as a teen?
What are some embarrassing diaper punishments?
Were you ever forced to wear a diaper when you were a teenager?
What is the most embarrassing diaper experience with a babysitter as a teen?
Have you ever worn a dirty diaper in public as a punishment?
Have you ever been caught being diapered in public or at a friend's house? If so, what happened?
Have you ever been diapered, or put into a diaper, during a sleepover?
Have you ever been put in diapers against your will?
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I do… So sorry it’s long. I think I was about 14 or 13, I remember a friend who had a little sister who was a bed wetter a few years ago and had to wear diapers, My friend had dared me to put one on. Of course, I told her that no way I was going to do that! Then my friend did chicken sounds. I hated it when people did it to me, especially friends. I told her only if she did it with me. She shrugged and said she did it before, No biggie. No biggie? A huge biggie for me! I thought to myself. She quickly ran to her sister's room and grabbed two big bulky diapers, with two pairs of plastic pants.
I do… So sorry it’s long. I think I was about 14 or 13, I remember a friend who had a little sister who was a bed wetter a few years ago and had to wear diapers, My friend had dared me to put one on. Of course, I told her that no way I was going to do that! Then my friend did chicken sounds. I hated it when people did it to me, especially friends. I told her only if she did it with me. She shrugged and said she did it before, No biggie. No biggie? A huge biggie for me! I thought to myself. She quickly ran to her sister's room and grabbed two big bulky diapers, with two pairs of plastic pants. ( I was spending the night too.) I asked her what were the plastic pants for. She simply replied, “To sleep in DUH!” As if it was nothing! She handed me the plastic pants and diaper. She quickly put on the diaper and the plastic pants. I just stared at them, She quickly snapped at me saying “ Put them on Kayla! Before my mom comes home.” I just stared a
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