Category Archives: Activities

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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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/

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.

Dusting Off the Polling Booth

Now that you have seen all the pretty maids in a row, please take a moment to vote for the most humiliating pictures. If one sissy has a lead when the polls close early on Saturday Sunday morning, that sissy will be exempted from the follow-up punishment, “Sorority Bitches”.

[poll id=”12″]

Note that clients are required to vote, but **may not** vote for themselves. Clients who choose not to vote will be automatically included in the follow-up punishment.

**Update:** Due to some issues with the poll not allowing people to vote, voting has been extended by 24 hours.

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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