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

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Pieclown: Happy New Year

Mistress Katzenburg has issued her first assignment for the new year to me. I am will be dressing up as the hung-over housewife, alone and in bed late into New Years Day.

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Happy New Year

Happy New Year to all of the sissies out there. May this year be better than the last. To help us ring in the year, there are some new years assignments for all of the clients out there.

* [sissy billy][] will be dressing up as Baby New Year. Unfortunately the baby has been bad and had to be bound into her giant diaper before being dressed for her 0th birthday party. She has a big day waddling around before being put down for her nap and given her pacifier to suck on. (Baby New Year doesn’t realize her pacifier is really a rubber dildo—she just knows sucking on it gives her sweet dreams.

* slut_tricia will be dressing up as a single New Years Eve party girl. Who stays out and parties until she finds a way to get herself in trouble—tied up and “open for business”. Will she have any takers for the services she can offer?

* [Pieclown][] will be dressing up as the hung-over housewife, alone and in bed late into New Years Day.

_All assignments are due to be posted NLT Sunday evening._

[sissy billy]: http://institute.cdpunishment.com/profiles/sissy-billy/
[Pieclown]: http://institute.cdpunishment.com/profiles/pieclown

How I spent my summer vacation – Episode 4

It has been quite a while since I have related another of my summer experiences with Mistress Rosemarie. I was supposed to do this on a regular basis, but forgot and to be honest put it off since my summer vacation was mostly humiliating with many embarrassing activities, trips and things with her. Well the year is almost over and as all things do it has caught up with me big time. This past summer often found me in hot water, but none more so then when I tend to embarrass Mistress Rosemarie in front of one of her friends.

The specific day was a nice warm day in August and we were suppose to go to the beach with one of her friends from work. This was always fun and mostly stress free for me since Mistress Rosemarie was seldom inclined to embarrass me in public by having me do girlish things. It was Saturday and when we went to pick up her girlfriend she explained that she had her period, did not feel good and really did not want to go to a sandy beach. I had been looking forward to this and I lost it. I cried and before I thought, I said I didn’t care if she had her period, she could stay home and we should go without her. No sooner were the words out of my mouth and the look on Mistress Rosemarie’s face told me I had crossed the line. I knew it was insensitive and I knew I would regret it.

Mistress Rosemarie left the room with her friend and when they came back smiling they told me it was about time that I had my first feminine period. I blushed a deep red, but knew better then to say a word. Well out came the feminine sanitary products and their fun began and my misery started. Her friend seemed to feel better that she had a girlie sissy to commiserate with. I was very much embarrassed by this day that I had hoped never to have to relay it for all to hear.

I somehow never learn my lessons though. Last week I made the same awful insensitive mistake again with another one of her friends because it interfered with us going out to a party. She was totally livid and then she remembered my unlearned lesson from this past summer.

Well, this has now become – How I spent my summer vacation – 4 and also how I spent my Christmas vacation – 1.

This past Tuesday Night I came home to find Mistress Rosemarie with both of her girlfriends that I had embarrassed by being insensitive about their periods. They reminded me about how I had said to all of them that I did not see what the big deal was about a little stomach ache and having to wear a rag between there legs. Well, Mistress Rosemarie then smiled and said that it was about time that I realized what a big deal it was.

I was led into the bathroom and spread out on the counter was my impending lesson.

[![](http://cdpunishment.com/institute/images/2010/12/sissybilly_101229-002t.jpg)](http://cdpunishment.com/institute/images/2010/12/sissybilly_101229-002s.jpg)

I was to have my first feminine period and I would certainly learn what the big deal was after 24 hours. I groaned, but there was no way out of this now.

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Travels and Other Things

For my second assignment Mistress has demanded that I write up some of my travels and experiences. Thinking about it, the only way I can do this is in chronological order. After all, that is the only order I know unless Mistress clicks her fingers. I’m sure that will work because as time has gone by, I have gradually got farther and farther out of Manchester. So first a picture of me in the Arndale shopping centre; the biggest in Manchester.

I now know shopping for clothes and make-up is one of the joys of life

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Introduction

Hello All,

Mistress has asked me to introduce myself. This may take time as there is quite a lot to tell but I will try to keep it fun. I love fun you see, it is the one consistent theme of my new life. The farther and deeper I get into Tricia’s head the more fun I have. It can be hard work sometimes though.

I’ll begin though with the boring bit. I was born 53 years ago as a male in a hospital near Wembley Station. That makes me British and, trust me, I’m very British. I had a normal education, enjoyed university, went into IT and had three children (who are now grown up and I love dearly). I did all this by denying Tricia’s existence. I knew she was in me but was far too scared to let her out, or let anybody know about her existence. That was until my Father died. Through no fault of his I seemed more free and became determined to get Tricia out. And girl, have I done that!

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How I spent my summer vacation – Episode 3

It was a really nice Sunday in July and I had been told to dress nicely for Church. To clarify, Mistress Rosemarie and I always attended Church on Sundays, but while it was a threat to keep me behaving as a good sissy, we would sit in living room, me in a straight back chair, and watch the church service on the television. Sunday dress was either a nice skirt and blouse or sometimes a dress, stockings, high heels properly applied makeup and perfumed. I am always directed to dress and look lovely for Sunday.

My mistake this particular Sunday was to over react to a simple request from Mistress Rosemarie. She thought a nice picnic on such a nice summer day would be lovely. I got hysterical thinking that we would be going to the town park with me dressed in my feminine Sunday finery for all to see. I started to whine and refuse to even listen to her explanation of our picnic plans. I am so afraid of exposure to others that I would not listen. I carried on for 5 minutes until Mistress Rosemarie lost her temper, started yelling at me and I finally shut-up. When I was quiet for a minute or two, she just smiled and said OK, that we would have our picnic indoors, but that I had passed up a very pleasant afternoon. She later explained that she had found a very secluded place and it would have been very private.

I went and fixed myself and my makeup from my hysterics and stood in the kitchen where we would be having our picnic.

[![](http://cdpunishment.com/institute/images/2010/11/sissybilly_101023-001e-e1289139389772.jpg)](http://cdpunishment.com/institute/images/2010/11/sissybilly_101023-001s-e1289139455928.jpg)

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But Not Too Much

I couldn’t help laughing at the dichotomy presented by this text and picture combination (both from the same application process):

> Thank you Mistress Katzenburg,
>
> I promise to do as you command, and I will answer whatever questions you have both promptly and honestly. Please don’t post the pictures you have of me please Mistress.

![sissy-6f.jpeg-cropped.jpg](http://cdpunishment.com/institute/images/2010/11/sissy-6f.jpeg-cropped.jpg)

Council of Phi Decree

WHEREAS, the Council of Phi expects those installed in positions of power in organizations such as The Institute and Kappa Delta Pi to exhibit the highest integrity and exemplary work ethic at all times;

WHEREAS, Mistress Katzenburg has had over 7 weeks to finish the details celebrity bowling event for Kappa Delta Pi and has repeatedly failed to do so;

WHEREAS, Mistress Katzenburg has two new membership applications to The Institute that she has failed to deal with properly;

WHEREAS, Mistress Katzenburg has a two month backlog of email messages related to The Institute and Kappa Delta Pi that she has failed to control,

WHEREAS, Mistress Katzenburg is over 10 lessons behind on training for Week 3 of the Kappa Delta Pi pledge process;

WHEREAS, Mistress Katzenburg has failed to accurately track demerits for clients of The Institute and pledges of Kappa Delta Pi;

THEREFORE BE IT DECREED, that starting this evening, Mistress Katzenburg is to be held in a constant state of punishment and humiliation until such time as she is able to bring all of these activities current, including

(1) Postponing the celebrity bowling event,

(2) Soliciting punishment ideas from all current Mistresses and clients and pledges,

(3) Posting this decree on the front page of The Institute website;

FURTHER, IT IS DECREED, that if Mistress Katzenburg is unable work off her backlog before Monday morning, November 8th, she will be stripped of her commission at The Institute and removed from her position as Pledge Mistress in Kappa Delta Pi.

As set forth this 5th day of November, 2010 by the Council of Phi.

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.

[![](http://cdpunishment.com/institute/images/2010/11/sissybilly_101019-004e.jpg)](http://cdpunishment.com/institute/images/2010/11/sissybilly_101019-004s.jpg)

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.

[![](http://cdpunishment.com/institute/images/2010/10/sissybilly_100820-001e1.jpg)](http://cdpunishment.com/institute/images/2010/10/sissybilly_100820-001s1.jpg)

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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.

[![](http://cdpunishment.com/institute/images/2010/10/sissybilly_100820-001e.jpg)](http://cdpunishment.com/institute/images/2010/10/sissybilly_100820-001s.jpg)

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

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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.

[![](http://cdpunishment.com/institute/images/2010/07/sissybilly_100710-001e.jpg)](http://cdpunishment.com/institute/images/2010/07/sissybilly_100710-001s.jpg)

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

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babyface

After failing at her [Sorority Bitches][sb] 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.
1. Put a pair of panties in a cup or bowl.
2. Empty your bladder onto them, then set them aside.
2. Note what time it is.
3. Perform _at least_ two cleansing enemas to make sure you are good and clean.
4. 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.
3. 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.)
4. Secure this diaper with duct tape (or other means). It will be on for a while.
5. Pull an additional (un-cut) disposable
6. Put on a bra
7. Lock on ankle cuffs and wrist cuffs.
8. Put on whatever other clothing your Mistress requires/allows.
9. 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.
10. 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.)
10. Stuff your bra. Besides what is given here, dress as your Mistress sees fit.
11. Over-top the disposable diaper, put on one that is “super-stuffed”. (Like [these pictures of Stacee Skye](http://institute.cdpunishment.com/2009/01/pink_and_plasticy).) The diaper should be secure and stuffed enough to ensure that you can only waddle.
12. Using a black magic marker, write “sissy” on your forehead, “baby” on your right check and “slut” on your left.
13. 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.
13. Do whatever other tasking your Mistress desires.
14. After 22 hours, you are coming to the end.
15. Gag yourself with the panties you set aside earlier and think about your punishment for a few minutes.
16. Once you have posted the results, you can remove the gag. You are finished.

**Notes:**

* 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]: http://institute.cdpunishment.com/profiles/sissy-billy/
[sb]: http://institute.cdpunishment.com/2010/06/sorority_bitches_report_card

Impediment == Speech

I think this speech, which is being sent to [sissy billy][] explains everything fairly nicely:

> sissy billy would like to apologize to Mistress Rosemarie and Mistress Katzenburg for falling so far behind on her assignments. sissy billy realizes that she has been afforded an excellent opportunity to pledge Kappa Delta Pi, but cannot start on time because she has neglected her other assignments for a very long time. sissy billy is very sorry that she has embaressed Mistress Rosemarie by not being ready for this opportunity. To rectify this, sissy billy has been given this speech and will follow the directions written herein.

> Before going to bed, sissy billy will get dressed in her silky nightgown and record a video of herself reading this entire speech. After reading the speech sissy billy will, show herself stuffing a bar of soap in her mouth. sissy billy will then save the video and upload it for Mistress Katzenburg’s amusement the following morning. sissy billy will be allowed to remove the bar of soap when allowed by Mistress Rosemarie. sissy billy will not be allowed to rinse her mouth out or change clothes before going to bed.

> sissy billy will continue this ritual every night until she is caught up on her assignments. sissy billy will work diligently to catch up as she realizes Mistress Katzenburg will make this ritual harder over time and the longer the delay, the more Mistress Rosemarie is humiliated.

[sissy billy]: http://institute.cdpunishment.com/profiles/sissy-billy/

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