Tag Archives: assignment

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

Sorority Bitches Report Card

After a few days of waiting, the Sorority Bitches finally have their report card:

Round | Activity | Pieclown | sissy billy
:——- | —— | :—–: | :———-:
Dressed for Dinner | Waiting Outside | Passed | –
 |Mush Mouth | – | Passed
 |Happiness Pie | Passed | Failed [^1]
 |A Happy Ending | – | –
Early Punishments|Trapped in a Cage | | Failed [^2]
 |Public Paddling | Passed | Passed
 |Oral Practice I | Passed | Passed
 |Oral Practice II | – | –
 |Cleaning Up | Passed | Passed
Late Punishments|Exercise Time | Passed | Passed
 |Private Paddling | – | Passed
 |Shower Time I | Passed | Failed [^3]
 |Shower Time II | – | Failed
 |Shower Time III | – | Passed
Bedtime|Easy | – | Failed [^4]
 |Medium | Passed | –
 |Medium (2) | – | –
 |Hard | – | –
 |Hard (2) | – | –

Pieclown has eight passes (including one in each category) and zero fails. She is passed.

Sissy billy has seven passes (in three out of four categories) and five fails. Since she didn’t complete all four categories, she fails this assignment. But all is not lost, as Mistress Rosemarie has nominated her for membership in [Kappa Delta Pi](http://institute.cdpunishment.com/about/kappa_delta_pi), so she should get plenty of sorority bitch experience in the coming months.

[^1]: Don’t hold the pie pan in your hands if “no hands allowed”

[^2]: You have passed the activity “Sitting in a Box”

[^3]: See pieclown’s post for the meaning of bikini shave

[^4]: Partial credit may be available, but even giving her half credit for nights one and two, she still comes up a full night short on the easy task.

pieclown:Sorority Bitch

When [Mistress Katzenburg](http://institute.cdpunishment.com) gave the assignment of [Dusting Off](http://institute.cdpunishment.com/2010/06/dusting_off) she let us there would be a [poll](http://institute.cdpunishment.com/2010/06/dusting_off_the_polling_booth) to see who did it the best. The winner would not have to do the next [assignment](http://institute.cdpunishment.com/2010/06/sorority_bitches). I was not the winner so had to participate in seven of the nineteen activities, spread over the four sections. One from each section.

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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.

![](http://cdpunishment.com/institute/images/2010/06/sissybilly_100613-001s.jpg)

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Sorority Bitches

All clients not [voted](http://institute.cdpunishment.com/2010/06/dusting_off_the_polling_booth) the most humiliated maid in [Dusting Off](http://institute.cdpunishment.com/2010/06/dusting_off) will participate in this follow-up assignment. Each client will participate in seven of the nineteen activities, spread over the four sections of the evening. One activity from each section is required. (Note that if you are working with a real-time Mistress, she gets to choose which seven you perform. Also note that seven is the minimum and more could be required.)

The loser of this round will then go on to pick from “Babyface” and “On the Town”. Hint: you want to win this round.

#### Dressed for Dinner

All of the sorority girls are dressed up for dinner. Corset, stockings, high heels and a dress are required.

1. **Waiting Outside** – All of the girls are milling around outside, waiting to be let in to the banquet hall.

2. **Mush Mouth** – Dinner is jars of baby food and large pitchers of formula.

3. **Happiness Pie** – After dinner, all of the sisters have a whipped cream pie eating contest–no hands allowed.

4. **A Happy Ending** – All of the sissy sisters are brought up in front of the rest, given a plate and forced to masturbate onto it. Once everyone is done, the plates must be licked clean.

#### Early Punishments

After dinner is over, cuffs and collars are added to each sissy sister’s attire and a selection of punishments occurs while still at the banquet hall.

1. **Trapped in a Cage** – The sissy sisters are each locked in a dog kennel while the rest of the punishments are prepared.

2. **Public Paddling** – Each sissy sister is taken from the cage and given a good paddling.

3. **Oral Practice I** – Next, each gets to choose from a selection of dildos to practice their oral technique on.

4. **Oral Practice II** – After the sisters are satisfied the sissies have learned that lesson well, each sister picks a sissy for another oral practice session–on her.

5. **Cleaning Up** – Since the sissies may be a bit messy by now, each is gagged with a bar of soap before being led out of the banquet hall.

#### Late Punishments

Now back at the sorority house, the sissies have been relieved of their formalwear, finding themselves in a t-shirt (with the absolute largest forms they have in use) and shorts. All are still collared and cuffed, with some who have been less cooperative hooded, gagged and otherwise restrained.

1. **Exercise Time** – To work off the effects of dinner, most sissies start on an exercise program. At least 3 different exercises are required. (Examples include push-ups, sit-ups, jumping jacks, running, swimming, jumping rope and walking on the elliptical.)

5. **Private Paddling** – Now that they are in the safety of their own house, the sisters break out all of the ass-busting implements and unleash until they are ready to quit. Sissies unclear on the concept of how long the paddling will last find themselves tied down and gagged while the blows continue.

2. **Shower Time I** – Sissies get a bikini shave

3. **Shower Time II** – Sissies get a leg wax

4. **Shower Time III** – To ensure their mouth is clean, sissies get to again practice their oral technique, this time on a wet bar of soap lubricated with dish washing soap.

#### Bedtime

Having showered, the sissies are now ready to be put to bed. The hard ones are reccomended, as it gets the activity over with quickly. Once marked medium must be done for three consecutive nights to be counted and those marked easy require five consecutive nights.

1. **Easy** – Wearing panties and a nightgown

2. **Medium** – Wearing panties, a fully stuffed bra and a nightgown

3. **Medium** – Diapered. Diaper can only be changed after getting up for the day.

4. **Hard** – Fully dressed and bound. Must include panties, hose, wrist cuffs, ankle cuffs, bra w/ forms, nightgown. Earplugs, blindfold and hood are also suggested.

2. **Hard** – Super-stuffed diaper, bra with forms and cuffs.

Stacee Skye: Dusting Off

Each time that I am dressed up as a maid, it seems I can get less and less work done. In addition to what you can see, I was well packaged and had several girdle panties on over the two rubber corsets. In case I had any thoughts about actually hearing instructions, my ears were also plugged before the rubber hood was pulled on. The cuffs were even locked on to make sure I couldn’t remove my gloves and get a hint of fresh air.

![btsp_100409-005s.jpg](http://cdpunishment.com/institute/images/2010/06/btsp_100409-005s.jpg) Continue Reading

pieclown:Dusting Off

When Mistress Katzenburg issued the assignment for Dusting Off The Institute for Cross-Dressing Punishment. I knew not to just post the photo from an [earlier assignment](http://institute.cdpunishment.com/2008/03/pieclown_replication-2).

![](http://cdpunishment.com/institute/images/2008/03/pieclown_080226-002s.jpg)

I would need a new picture.

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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.

![](http://cdpunishment.com/institute/images/2010/06/sissybilly_100606-001s.jpg)

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.

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Dusting Off

Since it has been quite a while since I have posted here, there has been a bit of dust gather, and it is in need of a good dusting off. All current clients are therefore to make a post of themselves in a maids outfit, ready for cleaning. Once the posts are made, a poll will be opening, and the client with the most votes will be exempt from the next, much more humiliating assignment.

Halloween Dress-Up – sissy billy Version

Mistress Amber is celebrating a Holiday likes she loves to do by making Sissies Dress-up for her amusement. I must admit that this is much more desirable then being punished as Cross-Dressing Sissies normally are. Mistress Amber has a very good memory or very good records or probably both. She remembered one of my very first submissions expressing my interest in Ballerinas (It was a picture actually). I do love ballerinas and the Tutu’s/Ballerina Outfits they wear. I always fantasized of wearing a Ballerina’s Tutu for Halloween, but never had the nerve to. So my assignment for Halloween is to dress as a top heavy Ballerina.

I was looking forward to dressing up as a Ballerina until Mistress Rosemarie reminded me to look at the “fine print” of the assignment. In my excitement to dress up I had not read the additional condition of my dress-up also being uncomfortable.

All of you should know, Mistress Rosemarie loves Halloween and always dresses up and usually drags me to a Halloween Party. I always refuse to dress up which aggravates her to no end, but she does make me go to the Parties. She was in her glory that I was going to be forced to be dressed up this year. I was terrified that she would make me go to a party dressed as a Ballerina. I was so thankful when she said that this year we would stay home. Mistress Rosemarie really is a nice Mistress and while she likes to humiliate me at home, she does know what a panic I was in to be exposed in public.

Early in the week she started to plan my Ballerina Costume. She picked out a white Tutu that could also fill in as a spare Crinoline under my Maid’s Outfit. Then she started to pick my accessories to fulfill the “Uncomfortable as possible” portion of the assignment. I naturally had my big Ladies’ Big Bra and over-sized stuffing already in my closet. Then she decided I should start to experiment with my “Spreading Core Diaper”. Add to that my corset laced tightly like a Victorian Lady, Stockings and my Punishment Level 5″ Pink High Heels. My Costume hung on the bathroom door for days so that I could anticipate my assignment.

This Halloween would be Exciting and Humiliating and Terrifying. (I was threatened with having to hand out treats to all who came to our house.)

It is Saturday Night and Halloween is here. I dressed up and I did complete my assignment. Thanks to Mistress Rosemarie, the humiliation was all mine. The fun is in the “detail” and not the assignment. This was a Halloween I should not soon forget.

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Cheer Me Up Story Contest – Chapter 3

Chapter 3 of the [Cheer Me Up Story Contest][1] is due on next Sunday. If you have posting privileges, you are to only save a DRAFT. All of the stories will be published on Monday morning. All of the rules can be found in the [original post][1].

New clients: Since you have not been required to write the two previous episodes, you have an option: You may write (and illustrate) chapters one and two following the rules to wipe out any outstanding punishment that you have. (One chapter removes one punishment.) If you don’t have outstanding punishments, this can be used in the future, at my discretion. Do not take this lightly—this may be the easiest punishment you ever have.

Suspended Clients: If you are readmitted to The Institute, you will be required to catch up on all stories you missed. Therefore, you may wish to stay up to date at this time.

[1]: http://institute.cdpunishment.com/2009/03/cheer_me_up_story_series

The Play – Kaya’s First Time – A Re-Write

The Play – Kaya’s First Time – is being discontinued.

At least for the time being and only as long as I can stay out of trouble. (I have been assured by Mistress Amber and Mistress Rosemarie that it can reopen on short notice)

In the past two weeks I have managed to get myself into several predicaments. I have made a wish that I had to make because of a lack of self control. I accepted the consequences for this wish and then asked for and was granted a change of the options which I now ask to change once again. I have also been rude and have failed to behave as a proper sissy should, both in posting comments and in emails to Mistress Amber.

I certainly need help in my training and constant supervision in my attempts to fulfill my assignments and accomplish my punishments. Heaven knows that I cause Mistress Amber a lot of effort in my training and I try to be appreciative of her efforts. I thank her for not giving up on me.

Mistress Rosemarie has just returned from a needed vacation with her girlfriends away from me. She provides a lot of supervision, control and acts as my conscious in support of Mistress Amber’s attempts in my training. I was told to stay out of trouble and obey Mistress Amber, but it is obvious by my actions of the last two weeks that I did not. She reprimanded me severely and left me to worry as she went to her computer to see how naughty I had been. I am sure she also traded some emails with Mistress Amber. Not Good and I expected the worse.

I was surprised at how calm she was when she came to my room to talk to me. Mistress Rosemarie then told me after some communication, that she was very surprised at how forgiving Mistress Amber was, that I was lucky that Mistress Amber must have other more pressing and important issues then my disobedience and if I was smart, which she said she didn’t think I was, that I better stay in my room and figure out how I could please Mistress Amber. Mistress Rosemarie said that she had some ideas, but that I better think of some myself and then she would help me formulate a plan to please Mistress Amber. I really do not deserve Mistresses so understanding. I had until dinner to come up with a plan.

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Chastity

I have been given an assignment by Mistress Amber to discuss Chastity. This is a new condition for me in the past few months and I am learning to understand and deal with. I have not found it easy or pleasant, but I shall relate my experiences to-date. I would be interested in how others have dealt with it and what they feel about Chastity.

To better understand a topic, go back to its origins and history. The concept of Chastity and in particular the use of Chastity belts go back about five centuries. The reason for Chastity as a practice was to temperate sexual behavior of legitimately married spouses or sexual continence of the unmarried child. Since men in the dark ages held the absolute power (except for maybe a Queen – imagine having a Queen as a Mistress. Punishments were severe in those days), this was directed almost solely at women and girl children. I am sure it was reversed at times, though there is little mention of this. An early chastity belt did not look pleasant and if your Master went off to a pilgrimage it could be months.

A Chastity belt was a lockable device fitted over the vagina of a female to ensure fidelity of a wife or guard the chastity of a daughter.

In today’s world a Chastity belt is considered a sex toy. I guess it depends on ones perspective or situation. If you are the Mistress or the Master, it can be fun to have the power of complete dominance and control. If you are the subservient, you may not agree.

This is a sample of today’s chastity belt for a female slave. Girls, does this look like fun or not.

I certainly would not like to be female and be placed in Chastity by my Master. This can not be pleasant to have a plug in her rectum and a plug in her vagina. It must be uncomfortable to walk or move around, but on the other perhaps the vaginal plug may produce an orgasm or two in moving around. Any of you female slaves might be able to give a better opinion on this. While these may be called sex toys in today’s world, they really are a means of dominance and control for an obedient subservient sissy or slave. The sole purpose of a chastity as in old times is to temperate sexual behaviour and to maintain the sexual continence of a Master or Mistress’s subservient sissy or slave.

For you male sissies, the purpose is no different or less terrifying or less controlling. This is a picture of the sissy clitty cage Mistress Rosemarie purchased for my training and obedience.

I had started my application for training as a client in “The Institute for Cross-Dressing Punishment” when on my doorstep was a package ordered by Mistress Rosemarie and strongly suggested by Mistress Amber for my training enforcement. I had heard about a chastity restraint, but had never seen one. It looked terrifying to me. That night I was instructed to model it, take pictures and send to Mistress Amber for approval. I did not know how to use it and it hurt in putting it on. It was confining and pinched everything that was my sissy clitty. Mistress Rosemarie made me wear it the first night. I was afraid even to pee.

The fact that I was to wear this contraption as a training device that took control of my sissy clitty totally away from me was humiliating. I have read back through my responses to Mistress Amber and I am embarrassed by them. If I had only accepted the lost of control of my sissy clitty and accepted that this control belonged to my Mistresses I would have avoided a great amount of punishment training. My whining about how bad it was (it was and still is) just made matters worst.

I had to wear it to work. I was so afraid that some one would know that I was wearing it. Every time someone looked at me I felt humiliated as if they knew and were laughing at me. It also hurt to move around in. Mistress Amber’s comment did not help. I was told that sissies sometime had to wear their sissy clitty cage for months at a time. That did not make me happy. I wore it to work, I wore it at night and did not sleep, I wore it every time I had a desire to wear a pretty negligee and I wore it every time it fit a punishment that Mistress Amber devised. It did help me in curing my desire to touch myself. Good for Mistress, bad for sissy billy.

I complained about how it pulled my pubic hair. Mistress Amber helped me solve that problem. I shaved my sissy clitty. This was the first time I ever had to do this and it was humiliating. It did stop the pubic hair pulling.

Dealing with the mental side of my sissy clitty cage was by far the most difficult. It felt like old fashion armour hanging from my sissy clitty. In reality it was very light, but I could feel the weight between my legs. I was always self conscious when wearing it in public. It was well hidden by my pants, but I imagined a huge bulge that hung there for all to see.. I was constantly afraid of being discovered. I felt it always and each time I felt it my subservience was the first thing I thought of. It was humiliating. It did cure me somewhat of scratching my balls. Difficult to due with it on. Mistress Amber delights in referring to this as my battle of the bulge.

It has now been three months of training in how to wear my sissy clitty cage. I do better in putting it on and wearing it for extended periods of time. At the start of my last assignment I wore it for three days straight both at work and home and in public. I took it off and accepted part two A of my latest assignment for reasons other then the cage.

After three months the physical side of subservience and confinement in my sissy clitty cage is bearable. The mental side has not changed. It is still uncomfortable and clunky and wakes me up at night when I turn over and pulls my pubic hair, but the most difficult mental part of this, though, is that I have no control over my sissy clitty and I am constantly reminded of this humiliating aspect. Control belongs to my Mistresses and is always there as a containing punishment for when I am naughty. I still have a long way to go in mentally accepting this.

I accept that I need help and would appreciate others suggestions and comments on how to do better in wearing my sissy clitty cage.

sissy billy

You Can Teach An Old Dog New Tricks

There is an old saying that ” You Can’t Teach An Old Dog New Tricks ”

Well that is not entirely True. You Can

Last week I reported that on my trip to visit Relatives, that I did not wear my thong – “Sissy Summer” – at nights because of so many people around.

This past weekend was that second half of a very busy two weeks for me. I had a four day weekend with a bunch of friends that I do every year. This year we rented a House on a lake with 9 people. I was worried how I would be obedient to Sissy Summer.

I must first thank pieclown because I did remember her advice about keeping the thong on under her boxer shorts.

Then I definitely remembered Mistress Amber’s admonition (Threat of Punishment) that if I had just kept my thong on it was all right to wear boy’s underwear over them.

Well I remembered. I wore my thong 24/7 with my boy’s underpants over my thong. It was uncomfortable, but I did it. An Old Dog finally listened and remembered and hopefully honored and was obedient to Sissy Summer.

Thanks – pieclown and of course – Mistress Amber – I never took my thong off.

sissy billy and Sissy Summer

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