Tag Archives: cuffs

Maggie Rae: Story Assignment 3—Back and Forth

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?

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Maggie Rae: Life Imitates Art

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…

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Geek Girl: It’s a Maid, Maid, Maid World — Redux

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.

Fantasy Island – 5b “The After-Party”

My First Prom was all that I wished for or could expect. But, as often happens at a Girl’s Prom, things take an unexpected turn.

I apparently passed out after drinking too much wine. I am told that I passed out on the Bed and what came after was a Dream … or Was it?

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Geek Girl: It’s a Maid, Maid, Maid World

As I sit awkwardly here writing this—awkwardly as I’ve been sitting in a wet and messy diaper for the better part of five hours—I know I’m rapidly approaching the end of my assignment. The Geek Girl series of assignments have been quite unpleasant up to this point (and I’m not expecting them to get any easier as I go—it would be nice though), and this assignment was no different. If you are one of the hopefuls applying to The Institute, know that fates similar to this await you—you have been warned. Warnings aside, however, on to what has been my quite unpleasant morning, it’s a Maid, Maid, Maid World after all…

You are to get dressed as follows and remain dressed until your time is up. You should pick a period where you have enough free time, because stopping your assignment will mean repeating it. Also, changing your eating or bathroom habits in preparation for this assignment is not allowed.

Dress is very similar to Eight Legged Clean Freaks and consists of:

*A super stuffed diaper.

*Standard bra and forms

*Nylons

*Wrist and ankle cuffs

*A black garbage bag fashioned into a maid’s dress (with a belt and white towel for an apron).

*Hair in dual pony tails

Once you are dressed, you are to clean your apartment from top to bottom, until it can pass a white glove test.

Evidence:

*Once every two hours during the entire assignment, you will submit a picture of your current condition.

*Once your apartment is clean, you will submit to me a video tour of all areas of your apartment as proof of completion. This will be used to judge whether or not you pass.

Your assignment length is determine by the following rules: 1. Your assignment will not be over (and you cannot get undressed) until you have submitted the walkthrough video and made a post on The Institute website. 2. The minimum assignment length is 36 hours. 2b. The minimum assignment length will be considered to have been met once you stew is a messy diaper for at least 6 hours. 3. You can change your diaper as often as you would like, but each change adds six hours to the minimum assignment length.

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A Summer Kickoff Weekend for a naughty sissy

This all started out rather harmlessly about a month ago. I had been particularly rude to Mistress Katzenburg and even though I had apologized profusely expressing my sincerest regrets, I was wrong and Mistress was right (as she always is) and I deserved to be punished and given an assignment.

I was surprised at how simple the assignment seemed to be. I was to find several recipes for making of fake cum. Sounds rather simple, does it not. I searched and searched the internet and really only found two. I unfortunately was taking my time and not corresponding with Mistress about my difficulties. As you all know, that is a real no-no.

Last week I guess Mistress Katzenburg had enough and in concert with Mistress Rosemarie, decided that since it was summer that it was only appropriate that this sissy start the summer off right with a “Sissy” Weekend.

Oh My, did I wish I had been more responsive with my simple assignment.

My assignment of finding the “FAKE CUM” was withdrawn. I am sure, however, that it will surface again as Mistress Katzenburg never forgets any failure of mine and they are often revisited in a much harder form.

I was to find a nice sissy e-card on the internet and write a private sincere apology to her.

I was also to wear a very stuffed diaper and extremely stuffed bra for a 12 hour period for one night of the weekend without changing. As most of you know this is always a disgusting assignment.

Also in honor of Mistress Amber’s Summer of Panties two years ago when I had to wear feminine and pretty thongs to teach me a lesson, I would be required to wear a thong and bra when at home until I completed my post.

The rest of the weekend would be filled with little fun assignments devised by my Two Mistresses.

I was to document on an hourly basis to ensure my compliance. I dug out all of my prettiest thongs.

An so a sissy’s summer weekend started

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sissy billy: Happy Year 2011 – Again

Well, here I am again celebrating Happy New Year 2011 – Again.

I have been a sissy client for quite some time now and I should know better, but I was lazy and lax and have not read the Rules and Regulations lately. Big Mistake. I know that I am supposed to upload all untouched photos for Mistress Katzenburg to review and pass judgement. I accomplished the hardest part of the activity – celebrating Happy New Year 2011 and failed to do the simplest of requirements and upload the photos.

I will now pay the price for forgetfulness and lack of focus of accomplishing all my tasks. And – the second time for any assignment is always more difficult. Depending on the mood of the Mistress and how bad a sissy is it can be really really bad. I guess a repeat of the assignment and one added assignment means I was really not that naughty, but I still have not been told what the “Whine and Cheese” means. I will find out.

Happy New Year 2011 to all again.

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Application for the position of Reference Librarian

During the course of my training and punishment for Cross-Dressing as a sissy client of “The Institute for Cross-Dressing Punishment” a system of demerits was devised by Mistress Katzenburg to grade my failures and try to instill additional incentives to succeed for this sissy. Many demerits were added privately from Mistress Katzenburg to me and some publicly. I have many demerits and I had no idea how I would be able to get rid of them. I knew I would eventually be somehow punished for each and every demerit for each and every failure.

I wish to thank Mistress Katzenburg for presenting several possibilities for this sissy to make up for her failures. As a sissy will usually do, I chose the most innocent appearing of the challenges afforded me.

I chose to submit my application for the position of a Reference Librarian. Only time will tell whether I chose wisely or not. I drafted an initial application with the following thoughts.

Every Librarian I have known has been prim and proper. I put on my white bra, slightly stuffed (Most Librarians have small boobs), white panties, pantyhose, a white slip, white low heel shoes, and a librarian’s dress. I also put a bow/ribbon in my hair. As I stood in front of my mirror I looked at myself in the mirror.

As I looked in the mirror Mistress Rosemarie walked in and asked if that was what I really thought a Reference Librarian for “The Institute for Cross-Dressing Punishment” would look like as the “Institutes” Reference Librarian.

I knew that if I submitted this picture with my application that Mistress Katzenburg would quickly put my application into the rejection box. Back to my closet of sissy accessories I went.

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How I spent my summer vacation – Episode 2

It was a normal Summer Saturday and Mistress Rosemarie had laid out my sissy maid outfit that I was to wear for cleaning the house this week. I am sure that every sissy is made to clean her Mistress’s House and that was normal.

Let me rephrase that. Dressing as a sissy maid for Mistress Rosemarie and other Mistresses of “The Institute for Cross-Dressing Punishment” is never normal. The Mistresses always seem to have a way of making every simple cleaning day an adventure in reminding me of what it means to be a sissy maid. There always seems to be corsets, cuffs, sissy clitty cages, diapers or something terrible and uncomfortable to hinder my cleaning routine. At least today I was given my 2″ heels instead of the 5″ heels (when I am really being punished) to wear.

Well I dressed as instructed and presented myself to Mistress Rosemarie for the “sissy-do” list of cleaning chores that she would require me to do.

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How I spent my summer vacation – Episode 1

I have been instructed by Mistress Rosemarie to share some of the fun and games and activities that I did over the summer. This is once again a lesson that I must endure by sharing my experiences and humiliations because I am shy. I should have learned by now that I can not hide my humiliations and if I had shared just one with pieclown I may not be having to post several. Mistress Rosemarie has set a quota of 1 or 2 posts a week of my many humiliating days I spent on my summer vacation. This is to go on until Mistress Rosemarie has felt that I am over my current phase of sissy shyness. Of course I am sure that Mistress Katzenburg may also have some things to say.

One day a package arrived in the mail and Mistress Rosemarie was very excited. It was a present she had ordered for me for my birthday in the fall. She smiled as I opened it and giggled as I turned red with embarrassment. It was a little girls fancy frilly party dress. She took my hand and led me to the bedroom and proceeded in telling me how to dress. I put on a stuffed bra, a crinoline and this very frilly baby blue little girls party dress. No one, not even a girlie girl would ever wear this. For a sissy to expose herself like this is beyond humiliating. I also put on red thigh high stockings, a very big stuffed plastic diaper because I was still a little baby and of course cuffs so that I would behave. I stood in the bedroom totally humiliated as she took pictures for my scrapbook.

My humiliation was only the beginning of our Mistress – sissy evening

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A sissy trying to work off her demerits

It is not any easy thing for a girl to pledge a Sorority in College. It is even harder for a sissy like myself to follow the rules and requirements of a Sissy Sorority Pledge. Mistress Rosemarie has several Sorority Pledging games she likes to play with me.

Some time ago Mistress Rosemarie shared her Sorority experiences with Mistress Katzenburg who also thought it would be a good learning experience for me to follow the same sorority pledge guidelines, requirements and in particular the punishments that came with a young lady trying to join a College Sorority.

An assignment given to me by Mistress Katzenburg many months ago was to return to all the posts that I had made and correct them perfectly following all the Rules and Regulations of “The Institute for Cross-Dressing Punishment”. I have barely corrected 1/3 of my posts and each time it was graded by Mistress Katzenburg and each mistake would be given Sorority/Institute Demerits and sometimes 2 and 3 “Sorority/Institute” Demerits if I made the same mistake again. I have not done well in this assignment and have many many Demerits. I have not been told what I would have to do to cleanse these Demerits or what punishments I would receive. I have been extremely lax in completing my assignment of correcting my postings and I am certain that Mistress Katzenburg will not be kind in administering further requirements.

However, a few weeks ago Mistress Katzenburg did offer me a kind opportunity to satisfy some of my many demerits. I was to dress in my diaper and pink plastic diaper covers, put on my big lady big Bra and stuff it sufficiently, put on my wrist and ankle cuffs and stay dressed as long as I wished.

I would be able to erase 2 demerits from my record for each hour I stayed dressed as such, but if I soiled or wet my diaper I would not be to deduct any demerits, but instead would be given 3 additional demerits for that hour. I appreciate this opportunity and was going to attempt it this past Sunday and get rid of as many as I could. I prepared my attire and restraints on Saturday Night so I could start early on Sunday Morning.

I was ready to begin and was hopeful that I would be successful and rid myself of a lot of “Sorority/Institute” Demerits.

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sissy billy’s Standing Training Rules – Punishment Completed, I Hope – 2009-June-04

How I hope I have pleased Mistress Amber

On 5/18/09 Mistress Amber established Standing Training Rules for sissy billy. I was unable to obey these simple sissy training rules and was punished in various ways proposed by me as a training exercise and modified and approved by Mistress Amber. I have endured these punishments since that time as the sissy I am should. This past Saturday I was able to complete the non work week assignment and since Monday have also obeyed and followed the work week assignments.

Confession:

As a sissy I should not brag about completing a simple assignment which any sissy should accomplish easily. As a new sissy in training I have had great difficulty with this. I proudly write that I have nothing to confess and I have accomplished the non work week and work week assignments.

Punishment:

For a work week assignment not followed. Since sissy billy needs her sleep, she can remove her cuffs before bed. However, to reinforce that she is still a sissy, on the nights she does not wear her cuffs, she will no longer be treated like a sissy, but like a sissy baby. Baby’s do not take showers in the morning, but sissy baby’s take baths and so sissy billy will take a bath and a sissy when taking a bath should always take a bubble bath. Each Day sissy billy will take a bubble bath each morning she does not wear her cuffs the night before. Additionally, since sissy billy is still trying to learn to wear her sissy clitty cage, she will be required to wear it whenever she is wearing her cuffs.

Completed Punishment:

Since Monday I have obeyed the assignments and therefore did not incur additional punishments. I did, however, owe three days of punishments for days that I did not follow the punishment assignment at the beginning of the training. Therefore, each morning before I went to work this week I did not take a shower. I filled the bath tub for a sissy bath and put lots of bubble bath in it so there were lots of bubbles. I then took a bubble bath like a sissy baby. When I was done I patted my self off with a fluffy towel like a sissy would do. I was also wearing my sissy clitty cage whenever I was in the house and I had my cuffs on. This was typical of what I have done each day to complete my assignment.

Of course this punishment is not complete unless Mistress Amber concurs and tells me that it is.

I hope she does since I really will sleep better without my sissy clitty cage on and I am so looking forward to a shower like a normal adult again.

I, of course, am still bound by the rules as originally stated in my Standing Training Rules and will wear cuffs when I am in the house (I am doing so as I write this post) and will abide by the dress rules.

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sissy billy’s Standing Training Rules – Back to being Punished – 2009-June-01

How I have disappointed Mistress Amber

Confession: Well I am sorry to say that after a single night of success, I am back where I started. It was Sunday Night and I had all intention of wearing my cuffs and sissy clitty cage, but after an hour of laying in bed and thinking too much about my obedience and servitude trying to please Mistress Amber two nights in a row, I broke down and took off my cuffs so that I could go to sleep. I again have a busy week at work, but that is no excuse to disobey Mistress Amber. A sissy should be able to follow and complete simple assignments and again I am not up to my punishment.

Punishment: Since sissy billy needs her sleep, she can remove her cuffs before bed. However, to reinforce that she is still a sissy, on the nights she does not wear her cuffs, she will no longer be treated like a sissy, but like a sissy baby. Baby’s do not take showers in the morning, but sissy baby’s take baths and so sissy billy will take a bath and a sissy when taking a bath should always take a bubble bath. Each Day sissy billy will take a bubble bath each morning she does not wear her cuffs the night before. Additionally, since sissy billy is still trying to learn to wear her sissy clitty cage, she will be required to wear it whenever she is wearing her cuffs.

Completed Punishment: Each morning before I go to work I do not take a shower. I fill the bath tub for a sissy bath and put lots of bubble bath in it so there is lots of bubbles. I then take a bubble like a sissy baby. When I am done I pat my self off with a fluffy towel like a sissy would do. I am also wearing my sissy clitty cage whenever I am in the house and I have my cuffs on. This is typical of what I have done each day when I have not worn my cuffs to sleep and that has been every night during this work week.

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sissy billy’s Standing Training Rules – Punishment – 2009-May/June – Typical for each Day

How I have disappointed Mistress Amber

Confession:
On Typical Work Week nights I can not sleep with the cuffs on and when I am ready to go to sleep, I remove my cuffs.

Punishment:
Since sissy billy needs her sleep, she can remove her cuffs before bed. However, to reinforce that she is still a sissy, on the nights she does not wear her cuffs, she will no longer be treated like a sissy, but like a sissy baby. Baby’s do not take showers in the morning, but sissy baby’s take baths and so sissy billy will take a bath and a sissy when taking a bath should always take a bubble bath. Each Day sissy billy will take a bubble bath each morning she does not wear her cuffs the night before. Additionally, since sissy billy is still trying to learn to wear her sissy clitty cage, she will be required to wear it whenever she is wearing her cuffs.

Completed Punishment:
Each morning before I go to work I do not take a shower. I fill the bath tub for a sissy bath and put lots of bubble bath in it so there is lots of bubbles. I then take a bubble like a sissy baby. When I am done I pat my self off with a fluffy towel like a sissy would do. I am also wearing my sissy clitty cage whenever I am in the house and I have my cuffs on. This is typical of what I have done each day when I have not worn my cuffs to sleep and that has been every night during this work week.

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