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.

Mistress Rosemarie, however, thought that I had not accepted Mistress Katzenburg’s generous offer in a timely manner or with a positive attitude and as a result felt that a few caveats should be added. She also commented to me that she had never been given such a seemingly easy way to erase demerits when she was a Sorority Pledge, so why should I.

So, she added the following conditions:

  • I could not stop whenever I wished or just before I could not keep from soiling my diaper.
  • I would have to commit to 4 hour increments.
  • Mistress Rosemarie would serve me a delicious meal at the start of each period, Baby food fit for a baby.
  • In the morning I would be given a heaping tablespoon of Castor Oil to make sure I was not constipated.
  • I would drink a big glass of water each hour.
  • Mistress Rosemarie would have several surprises for me as the day went on.

I accepted my medicine for not being prompt and agreed to Mistress Rosemarie’s added demands and was ready to start early the next morning.

I was hoping to start at 8:00 AM in the morning and go all day and into the night. I also knew that I often had to go to the Ladies Room several times each morning. I got up at 7:00 AM and sat on the Toilet for a half and hour trying to empty myself, but by 7:45 I knew I had not succeeded, but I started anyway. I looked at the things I put out the night before and put them on and then presented myself to Mistress Rosemarie to “officially clock in”.

Mistress Rosemarie smiled and said a baby like me could not possibly crawl around the house in just a diaper and exposing herself in her bra. She then took out a baby romper set that she said I would look adorable in and told me to dress.

I must have looked very silly and when Mistress Rosemarie laughed, I knew I looked like a sissy baby and I blushed. Mistress Rosemarie then took my hand and took me to the Kitchen and with a giggled, said. “My little sissy baby must be very hungry after a long night’s sleep. Let me feed my little sissy a nice baby breakfast. I also know my little sissy did not completely go to the bathroom and she must be constipated, so I will also give my little baby a nice big tablespoon of Castor Oil which she help the little sissy when she has to go poops”

I sat at the table like a good sissy baby dreading my baby breakfast.

As you can see, Mistress Rosemarie had made me a large plate of baby cereal which always makes me gag and sometimes throw up. I was also given a tablespoon of Castor Oil which is tastes disgusting. I finally managed to finish my baby breakfast and finally after an hour (I also had to drink a whole glass of milk) I had succeeded in not soiling or wetting myself. I already was struggling in not wetting though.

8:00 AM – 9:00 AM Minus 2 Demerits

Since I had whined and cried through out my baby breakfast, Mistress Rosemarie made me sit facing the corner for the next hour.

As I sat in the corner my stomach hurt and was rumbling. I really really had to go to the bathroom. I squeezed my butt and tried not to pee. I always seemed to go to the bathroom at this time and this day it was not different except I was not allowed to go to the Ladies Room. Three quarters of the way through the hour I exploded. My diaper filled with poop and then with pee. How disgusting and embarrassing it is for a sissy to soil her diaper and I sat there humiliated. Mistress Rosemarie also had said that if I could not control myself like a proper sissy during the hour, then I would sit in my mess like a sissy baby until the hour was up. Finally I cleaned myself and put on a fresh diaper.

9:00 AM – 10:00 AM Plus 3 Demerits Total for my attempt – Plus 1 Demerit

This was not good. I had working on getting rid of Demerits for two hours and all that I had accomplished was to actually add a Demerit. Mistress Rosemarie just smiled and told me that is was difficult for her when she was pledging.

I next had to get dressed in a skirt and blouse and since it was Sunday, we would watch Mass at 11:00 AM on Television. I proceeded to dress and then sat on the bed for the rest of the hour as Mistress Rosemarie got dressed.

10:00 AM – 11:00 AM Minus 2 Demerits Total for my attempt – Minus 1 Demerit

I sat quitely on the bed waiting for my Mistress so we could go to the Living Room and watch the Sunday Mass. Whenever we watched Mass on Television, it was always very uncomfortable because I had to sit up straight in a Hard straight-backed chair. I tried not to complain, since the alternate threat was that she would take me out in public and have to go to the church.

I sat happily until about 11:30 and then diasaster struck. The baby food and Castor Oil started to take affect and I did everything I could to not poop. I was successful at that, but the glass of water every hour finally go to me and I pee-ed in my diaper. I sat in my very diaper watching the end of Mass thinking this was a very bad idea. I was not only getting rid of demerits, but was actually adding to my total. How discouraging.

11:00 AM – 12:00 PM Plus 3 Demerits Total for my attempt – Plus 2 Demerit

It was noon and I was losing ground. I decided to plow forward and try to do better in my next 4 hour cycle. Mi stress Rosemarie then decided that I would not be allowed to just sit around the house. When she was pledging a favorite chore was to clean the Sorority House. So she pulled out some embarrasing Maid accessories such as a crinoline and a baby bib and apron. Because I was wearing a diaper, she also decided that I should wear my rubberized diaper cover.

Being a Maid is really not a lot of fun. Clean – Clean – Clean. UGH. It normally is fun to dress up in my Maids outfit, but add a diaper and rubber jumper is not so much. I sweat ed a lot as I dusted, vacuumed and clean the kitchen. I did, however, complete my 4 hour cycle with only one mishap and put myself ahead on my demerit count. I wet my diaper only once. It really is hard to drink a glass of water each hour and not have to pee.

12:00 PM – 1:00 PM Minus 2 Demerits Total for my attempt – Even

After all this, I was back to where I started this morning.

1:00 PM – 2:00 PM Minus 2 Demerits Total for my attempt – Minus 2 Demerit
2:00 PM – 4:00 PM Plus 3 Demerits Total for my attempt – Plus 1 Demerit
3:00 PM – 4:00 PM Minus 2 Demerits Total for my attempt – Minus 1 Demerit

I was finally finished with my cleaning. Per my schedule, it was now time to take my sissy baby nap. I took off my sissy Maids baby outfit on put on one of my Negligees.

I laid in bed for almost three hours and was afraid to move. I did sleep for a short time, but mostly concentrated on not pooping or peeing. My stomach hurt as the Castor Oil really was working. I had kept my diaper clean for three hours and only had one to go. Then Mistress Rosemarie pulled out her most cruel surprise. She told me that several of the Sorority Sisters that really took pleasure in making it hard for the pledges use to do this often to her. Many times she was subjected to this punishment of baby food and Castor Oil which resulting in several humiliating accidents for her. She congratulated me on doing very well, but the real test for a Pledge was to hold it in with a finishing enema. She showed me a glycerin enema bottle and told me to roll over. I have had these before and I started to cry and with a slap on my bottom after she pulled down my diaper, she inserted the glycerin. I fixed myself and then had to stand in the corner.

I was really getting cramps now and finally I could not stand it any longer. I soiled my diaper. Finally the fourth hour was up. She asked me if I wanted to continue and I said no, I had finally had enough. I cleaned myself up and laid out the soiled diapers which I had been saving for a final count.

4:00 PM – 5:00 PM Minus 2 Demerits Total for my attempt – Minus 3 Demerits
5:00 PM – 6:00 PM Minus 2 Demerits Total for my attempt – Minus 5 Demerits
6:00 PM – 7:00 PM Minus 2 Demerits Total for my attempt – Minus 7 Demerits
7:00 PM – 8:00 PM Plus 3 Demerits Total for my attempt – Minus 4 Demerits

4 Hours (Soiled Diaper) X Plus 3 Demerits each Hour = Plus 12 Demerits
8 Hours (Clean Diaper) X Minus 2 Demerits each Hour = Minus 16 Demerits
TOTAL = Minus 4 Demerits

That was not very good. Only 4 Demerits erased for 12 Hours of Work and that is only if Mistress Katzenburg agrees and deducts them. I am relieved that this is over though. I had been dreading trying to do it. The best advice I can give to any future Sorority Pledges is be good and careful and do not get any Demerits to begin with.

12 Comments

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I can agree and deduct them, especially after Mistress Rosemarie made the rules that much harder for you. My diaper changes only had you losing 1 demerit credit for the hour—hers had you losing 3 credits.

Thank You Mistress Katzenburg

I may have to try to work off my past transgressions sometime too.

Hello sissysarah and pieclown. How nice it is hear from both of you. I was not sure anyone was still out there. It have been very quiet and the interest almost non-existent. I hope both of you are doing OK. Thank You for responding to my post. sissy billy

To all, I apologize. As is evident in the above comment, I have grown careless and lax in my use of proper English and Grammar. I was excited to hear from you and did not proof read the comment. I hit send instead of rereading what I wrote. Sorry, sissy billy

So how many demerits do you have left to work off?

Hello sissysarah

I do not know how many demerits I have left. Mistress Katzenburg was keeping the official log and I lost track, but I believe there are many left to work off.

I do hope the Institute becomes active again.

sissy billy

Oh Please Mistress Katzenburg, Please do not round my demerits to a Hundred. I do not know how many I have, but it can not be so many. It was so difficult to even erase four demerits. I was so thankful that you had given me the opportunity to erase demerits, but Mistress Rosemarie made it so hard and unfair I had almost not chance to succeed.

I did not know that I was to keep count. At first it was so easy, but I made so many sissy mistakes in my corrections of my posts and your grading formula double and tripled my penalties that I got confused.

I accept that they were my mistakes and that I deserved my demerits. I want to be a good sissy and I will try harder.

With so many demerits I fear that I will never erase all my demerits and I am at your mercy in trying to erase them.

sissy billy

I am getting really tired of your whining Billy. It was so hard and it was so unfair and you tried so hard. Give me a break. You seem to forget that I pledged a Sorority when I was in college and nothing you have been asked to do is as hard as I had to do.

I was a good pledge and learned my lessons and fixed my mistakes and did not get a lot of demerits. I worked them off without complaining, which is something obviously you are incapable of doing.

As far as not knowing how many demerits you have is completely unacceptable. You deserve to have Mistress Katzenburg increase them. I bet you have many more coming since you have stopped working on your assignment and are probably not even close to completing it.

Mistress Katzenburg, you should know that I warned my sissy about keeping track of demerits. I even gave her the perfect way of doing it. When I was a pledge we had to make a pretty Notepad to hang from our waist with pretty ribbons. We put the name of our Sorority on the cover with a pretty flower attached to the ribbons at the top. In this book we kept all of our lessons, demerits and how we worked them off. When asked, we could instantly tell the Sisters what our status was. So simple, but not for this Sissy. She was too embarrased to do something a feminine as that. As far as I am concerned, she has no excuses.

Mistress Rosemarie

I am sorry Mistress Rosemarie and I have no excuses.

sissy billy

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