Tag Archives: diaper

In a Row

All current clients are hereby given this assignment (since I’ve always wanted to have pretty maids all in a row). You will dress as a maid, given the following requirements:

  • A bra and your largest forms.
  • A super stuffed diaper. (One of these spreaders would be awesome, but outside the budget for most.) But that is the intended look which will enforce a full time waddle.
  • A black garbage bag fashioned into a maid’s dress (with a belt and white towel for an apron). For more information on making one, see this Dilbert cartoon.
  • A collar.
  • 10 lb weights around each ankle -or- metal bottle caps (top side down) taped to the bottom of your heels.
  • 2.5 lb weights around each wrist -or- clothes pegs on your nipples and a tall posture collar instead of a decorative collar.

There is an opportunity to lessen the amount of time of your assignment. For each of the following that you do (in conjunction with the assignment), the assignment time will be lessened by the Value number of hours. (For instance, if you are shaved from the neck down, your assignment will be 1.5 hours shorter.)

Plus Up Value
Bottle Caps and Weights 1
Painted Nails and Toes .5
Freshly shaved/waxed torso .5
Freshly shaved/waxed bikini .5
Freshly shaved/waxed legs .5
Retained Enema before Starting 2
Gagged for the Duration 2

Once you are dressed and have your plus ups decided, it will be determined how long your assignment will be. There are two different methods for calculating this. When replying to accept the assignment, announce which method you will be using.

  1. For each die, divide by two, rounding up to the next integer. Multiply the two numbers together, giving you a number between 1 and 9 hours
  2. Add sum of both dice plus two, divide by two, rounding up to the next integer giving you a number between 2 and 7 hours.

After determining the value of your rolls, subtract out the value of your plus ups to determine the length of your assignment. If the length is 0 or .5, round it up to one hour. If your assignment length is negative, roll again and recalculate without considering your plus up values this time.

Now that you are dressed and know the length of your assignment, you will have some time to perform maid-ly activities. This list shows all of the maid-ly activities that will be considered for points. It is highly recommended that you try to get as many points as possible. The client with the highest total will get a surprise. Clients without enough points may find themselves repeating this assignment.

Activity Value
Scrubbing the Floor 1
Cleaning the Toilet 1
Sweeping 1
Picking Up the Yard 6
Servicing the Man/Lady of the House 4
Cleaning Windows 2
Shopping at the Market 10
Serving Drinks 1
Caned/paddled by the Man/Lady of the House 4
Drawing a Bath 1
Taking the Trash Outside 6
Tied up by the Man/Lady of the House 2
Punished with a Mouth-soaping (Required) 1
Taking a Smoking Break Outside 2

Good luck to everyone. This assignment is due Sunday, April 3rd. If your post (and Dropbox files) are not in place when I check on Monday, your assignment will be late.

Maggie-Rae: Babyface

A long time ago, at the end of the Dusting Off series of assignments, Ms. Lisa spotted the assignment called Babyface which would be used as the highest level punishment for the ultimate loser of the series. After the completion of Sorority Bitches, she made sure to remind the Mistresses of The Institute so they wouldn’t forget it, ultimately dooming sissy billy to complete the task. Additionally, Ms. Lisa volunteered me for the task, despite my inactive member status at the time. At the time, I laughed at the torment that sissy billy had to endure, and it wasn’t until my time came that I felt the same pain he had. If he had performed his Sorority Bitches better, then maybe we both could have avoided it, but as it turned out, that was not the case. Now, I’m faced with the threat of repeating it, or worse, whatever the next and final step of the Dusting Off series would have been (seeing as I’ve already completed it once) dependent on how the evaluation of my own Sorority Bitches assignment goes. This is a record of my own instance of Babyface…

Continue Reading

Maggie-Rae: Shaving the Great Wooly Bison

This assignment known as Picture Perfect was the last thing I was assigned before my leave of absence from The Institute. As such, this assignment has been hanging over my head for some time, and it wasn’t until today that I finally managed to clear it. Even now I sit in its final result, which will last until I am up to date with my posting and have been restored as an active member of The Institute. The following images tell the ancient story of Cruel Mistress and the enigmatic Great Wooly Bison, how the Great Wooly Bison attempted to sway the Cruel Mistress with a show of sissy submission, only to ultimately be shaved bare and placed in a disgusting, gooey diaper prison. Continue Reading

Maggie-Rae: Dusting Off & Sorority Bitches

Returning to active status as a member of The Institute after a lengthy period of inactivity is no easy task, as I’ve been finding out these past couple days. A large backlog of assignments had been building, just waiting for my return, including an evil series of assignments that I just sat back, laughing to myself as the other sissies of The Institute soldiered through them a while back. The first of these assignments was Dusting Off, where we would report for maid duties in our best maid’s attire to clean the sheet of dust that had developed over The Institute from such a period of inactivity. I might be late, but here I am, reporting for duty none the less—better late than never, I hope.

Continue Reading

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.

Continue Reading

sissy billy: Happy New Year

Over the years it seems that I have had a difficult time in progressing from my baby years to even an adolescent sissy. Mistress Katzenburg has deemed that I should start out the New Year as a brand new baby.

To start the year I am to put on my largest overstuffed diaper, put on my prettiest baby dress to celebrate my 0’th birthday, waddle and crawl around the house and then I will be put down for my baby’s nap. But, because I have been bad recently, when I take my nap I will have a special baby pacifier. The pacifier will be the biggest dildoe that Mistress Rosemarie has bought for me.

Happy New Year to all

Continue Reading

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

Continue Reading

babyface – sissy billy failed Sorority Bitches

This is the third in a series of assignments to determine who is the worst sissy. The first assignment – Dusting Off – was a competition for us sissies to make a presentation and hopefully be excused for the next Level. I finished last in the polling and therefore had to move on to the next assignment of Sorority Bitches. I was the only one who failed this assignment and was to now have to complete an assignment at the third level. To compound my failure, I was not a graceful loser and therefore this assignment – babyface – was expedited and given to me to complete this weekend. If you read this assignment in one of the posts below, I think you would agree that it looks scary. It was not easy and as Mistress Katzenburg said, you do not want to be given a level three assignment.

This is a 24 hour assignment including the writing of the post and several awful tasks to perform. I accepted this assignment for failure of Sorority Bitches and started it at 4:00 on Saturday. My next 24 hours went something like this.

The first task was to strip. Not hard, but embarassing. Even a sissy like me can complete this and off to the bathroom I went.

OK – Now on to 24 hrs of accepting my failure and learning from it.

Continue Reading


After failing at her Sorority Bitches Assignment, sissy billy will have to complete the last assignment in this series, babyface. I was thinking of dropping it, but after Miss Lisa showed interest and sissy billy treated her so poorly, I thought it better to re-institute the final round.

  1. Strip.
  2. Put a pair of panties in a cup or bowl.
  3. Empty your bladder onto them, then set them aside.
  4. Note what time it is.
  5. Perform at least two cleansing enemas to make sure you are good and clean.
  6. On your hands and knees, beg your Mistress for a good spanking. Continue begging until she relents or you have kept it up for 20 minutes and throughly annoyed her. An evil Mistress might allow the first 18 minutes to get good and annoyed, and then lay into her sissy.
  7. Put on a disposable diaper which has slits cut in the bottom to allow it to leak. (Alternatively, you can use a re-usable diaper.)
  8. Secure this diaper with duct tape (or other means). It will be on for a while.
  9. Pull an additional (un-cut) disposable
  10. Put on a bra
  11. Lock on ankle cuffs and wrist cuffs.
  12. Put on whatever other clothing your Mistress requires/allows.
  13. Take her out of the house, wherever she wants to go. (Shopping, eating, a movie, etc.) She will decide when it is time to return.
  14. On returning, you will have a wet diaper. Not having on, constitutes a failure. (An evil Mistress might keep the trip short enough to ensure failure, but then insist, since it’s already started to continue this failed attempt.)
  15. Stuff your bra. Besides what is given here, dress as your Mistress sees fit.
  16. Over-top the disposable diaper, put on one that is “super-stuffed”. (Like these pictures of Stacee Skye.) The diaper should be secure and stuffed enough to ensure that you can only waddle.
  17. Using a black magic marker, write “sissy” on your forehead, “baby” on your right check and “slut” on your left.
  18. Spend some time sucking on your pacifier. (Actually a nice dildo.) If your Mistress has a strap-on, you should suck on that one too.
  19. Do whatever other tasking your Mistress desires.
  20. After 22 hours, you are coming to the end.
  21. Gag yourself with the panties you set aside earlier and think about your punishment for a few minutes.
  22. Once you have posted the results, you can remove the gag. You are finished.


  • You are allowed to change the outer disposable diaper as often as you would like (and your Mistress allows).
  • Mistressic license can apply.

sissy billy – a Sorority Bitch

A short while ago we were all given an assignment. Because the Institute had become quite dusty, we were to present ourselves as a sissy maid prepared to clean. A Poll was established to vote on who had presented themselves as the most humiliated sissy maid.

The losers were to be trained further and experience further humiliation as “Sorority Bitches”.

From the Start my performance was inadequate and had 0 Votes until a late surge left me with 2 Votes, but still in last place. I guess I was the most in need of humiliation and training by the Sorority and now I was to be a “Sorority Bitch”.

The assignment was basically that you were to experience a Sorority initiation Training Exercise in obedience and humiliation. There would be four Training Sessions over the course of the Evening divided into a Pleasant Dinner at a reception hall followed by a punishment session for insolent Sorority Bitches. You were then to be taken back to the Sorority House for some additional Training Punishments. Then, finally, it was Bedtime and a pleasant Sleep. The actual training episodes were not so pleasant.

It was for each of us to determine our training activities. We were required to pick at least one activity in each session, a minimum of 7 total activities and the Judges were to decided which Sorority Bitch would graduate and which would need further training.

I intended to try as hard as I could to impress the Judges and would attempt as many activities as I thought I could accomplish. To start, I strove to make myself as pretty as I could and be the Best Sorority Girl I could. I was to attend a Dinner at a reception hall and the dress code was a Corset, stockings, high heels and a dress. Since it seemed like a formal affair, I chose an old, but very pretty Fancy Dress that I once imagined wearing to a Prom.

I stood ready to be a Sorority Bitch.

Continue Reading

Dusting Off: sissy billy reporting for Maid Duties

“The Institute for Cross-Dressing Punishment” has become quite dusty and Mistress Katzenburg has requested that all good sissies report for Maid Duties. Mistress Katzenburg assigned all of us sissies to present themselves in their best Maids outfits and post a picture. The best presentable Sissy Maid will be exempt from the more humiliating and severe duties to Follow.

This sissy thought that she would not wear her very pretty pink serving maids outfit meant, but rather wear a more serviceable and practicable cleaning maid’s outfit. I put on pretty panties and decided that I would also wear a diaper and a pink plastic cover. I did this so that I could better service Mistress Katzenburg’s request if necessary and not have to stop for a Ladies Room visit which I often have to make. I put on a pink bra and stuffed it to medium fullness so as not to hamper possible cleaning duties. This was followed with pantyhose and 2″ heals for maid duties. Every good sissy maid must wear a crinoline under her outfit so she does look pretty if her Mistress decides to inspect and watch her cleaning. I put on a full white crinoline, pretty lacy white blouse and pink skirt. I then put on my white pinafore for cleaning to protect my skirt. I put on white lacy maids gloves and wrist-lets. I then topped this with a very pretty maids cap.

I present myself for inspection and assignment of sissy maid duties.

I have tried to look my prettiest as a sissy maid and still be functional as a cleaning maid. I hope I am picked as best in the sissy maid cleaning pageant.

Continue Reading

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.

Continue Reading

Junior Summer – 2 – Training Starts and The Surprises Keep Coming

“Oh My Heavens” sissy billy uttered. She was frozen in the middle of the floor and looked terrified. She obviously was afraid to move. She finally took a step forward and with hesitation she opened the front door.

There stood Mistress Rosemarie. sissy billy let out a sigh of relief for she had hoped Mistress Rosemarie would be her first trainer. Her hope was short lived. She told Mistress Rosemarie she would be right back as soon as she put on her clothes, but as she turned Mistress Rosemarie shouted stop. She grabbed sissy billy’s hand and dragged her outside still dressed in her peignoir set, cuffs and punishment high heels. She stopped on the front lawn and in the middle of the day there were lots of neighbors outside. The humiliation was intense for sissy billy and she turned red. Mistress Rosemarie then dragged her the rest of the way to the car like a little girl and sissy billy jumped in the front seat. Mistress Rosemarie made her get out and get in the back seat. She then said very loudly so all the neighbors could hear: “Sissies are like little girls and they should sit in the back seat. She then made a big deal of buckling sissy billy in with a seat belt and I am sure sissy billy could hear all the neighbors laugh and start talking. They then drove off.

Continue Reading

sissy billy’s Standing Training Rules – sissy billy Confession 2009-May-25

sissy billy’s Standing Training Rules had only been issued last week, but already I am in trouble and must confess to Mistress Amber. I love a pretty negligee, but I can never sleep at night while wearing one and that should be easy for a sissy. This was true with my diaper training and now more so with the selected activity of having to wear wrist and ankle cuffs while in the house. I sleep in the house, so therefore I should wear them to bed as a reminder that I am the sissy in training and Mistress Amber is in Control. Mistress Amber has thoughtfully tried to help in my learning to sleep as a sissy by constantly assigning sleep time activities. Since last week I have worn the cuffs while in the house, but have had to remove them to sleep. Last night I laid in bed until 1:00 AM trying to learn to wear them and sleep, but could not. I took them off. Today was a Holiday, so it was not bad. I do need my sleep during the work week though. Per Mistress Amber’s assignment, I am to propose a punishment and then carry it out if I am naughty. The last time I tried to do this in my Modified Wedding Punishment it was a disaster for me as I thought I could accomplish a lot and impress Mistress Amber, but to no avail. Thankfully she took pity on me and made my punishment less severe. This time I think I will propose punishments more in line with my abilities to accomplish them, I Hope.

The only portion of the activity that I failed to obey was the cuffs and only at night. sissy billy would like to propose the following punishment scenarios.

In the case where sissy billy does not wear cuffs so she can sleep during the work week, this should be a lesser punishment as she does need to work and get some sleep and so is only a naughty sissy.

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. Tomorrow sissy billy will start taking bubble baths each morning she does not wear her cuffs. 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. sissy billy will owe four additional bubble bath mornings when this assignment is completed.

The second part is for a very naughty sissy. Since this activity may go on for quite some time, I will offer some options for myself so as to vary the punishment. The following punishments are also punishments that sissy billy has had in the past and does not like. So by offering a variety, she may learn how to deal with her punishments.

On non Work Week nights like last night when sissy billy did not need her sleep and did it for her convience, the following punishments will be carried out the next day before she goes to sleep. There are six punishments and only one will be awarded to her when she is a very naughty sissy. sissy billy will take a single dice, roll it and whatever number appears will perform that punishment. Listed below are the punishments listed 1 thru 6

  1. sissy billy is to wear High Heels, a water balloon stuffed big bra, cuffs, sissy clitty cage, and a thong and stand in a corner for 10 minutes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  2. sissy billy will stuff a bar of wet Pink Camay soap into her mouth, put clothespins on her nipples, High Heels, cuffs, sissy clitty cage, and a thong and stand in front of the mirror for 5 minutes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  3. sissy billy is to make a bedtime snack of Level 1 and 2 baby cereal, vegetable, fruit and while wearing cuffs, sissy clitty cage, Stuffed bra and a thong eat the whole snack. After she has finish the baby snack she may take off her sissy items and climb into bed with a 4 oz bottle of baby formula and drink it. The sour taste of baby formula all night should remind her of being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  4. sissy billy is to put a bar of Pink Camay soap into water for 5 minutes so it is wet, soapy and gushy, get ready for bed by removing her sissy items and shove the Pink Camay into her mouth for 1 minute (enough time for the gooey soap to fill her mouth). She is then to take the bar of Pink Camay soap out, but is not allowed to spit any of the gooey soap in her mouth out, but must keep it in her mouth for another minute, get into bed and then she is to swallow it. The soap taste will remind her to think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  5. sissy billy is to put on High Heels, a water balloon stuffed big bra, cuffs, sissy clitty cage, and a stuffed diaper and rubber diaper cover, her teal Jumper to package it all and then using the treadmill in the basement walk for 1 mile waddling like Mistress Amber likes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  6. This is a Mistress Amber lucky – out of the goodness of her heart – get out of punishment card. There is no punishment, but sissy billy will kneel by the bed for 5 minutes before going to bed and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night. sissy billy gets to roll again and double the length of the punishment she gets on that roll. once completed, sissy billy will go to bed with all of her cuffs locked on anyway.

For last nights indiscretion sissy billy rolled the dice and the number two came up. I performed the punishment and will document it to Mistress Amber.

Of Course Mistress Amber has the option of modifying or changing any of the punishments above as well as deciding the length of this assignment. The next non work day is Saturday and so the very naughty sissy scenario will be decided after Friday night. Hopefully I do better this Friday Night.

Updated by Mistress Amber on May 28, 2009

The Actual Wedding Punishment – Sunday Night

It is Sunday Night and I have taken off my Sissy Maid Outfit.

Mistress Amber – I am sorry, but I must give up. I can not do this. I am so tired that I can not continue. I am sending this as a confession and an admission that I have failed to complete this assignment. I will send the rest of the photos tomorrow.

I apologize to all the other sissies as being a poor example of what a good sissy should be.

When I was young my mother would tell me that my eyes were always bigger then my stomach and I would always order more then I could eat.

Well, that is just what I did when I submitted this punishment to Mistress Amber as something I could accomplish. Mistress Amber even made it less severe and I still could not accomplish it. I am a poor excuse of what a good sissy should be.

I apologize Mistress Amber

sissy billy

Copyright © 2019. Powered by WordPress & Romangie Theme.