Tag Archives: sissy-billy

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/

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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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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A Trip with my Mistress

I made a big mistake at the end of last year. A sissy does not have any rights and only has the obligation to please her Mistresses. She is a sissy and should be kind and sharing with all and therefore has an obligation to other sissies also. She should be honest. But most of all she has an obligation to perform her sissy duties without prodding or insistence from her Mistresses.

Simply, she should Volunteer.

I did not and therefore I am where I am now. I am sorry Mistresses and other sissies. The correct thing to do would have been to show everyone how excited I was over my presents from Mistress Rosemarie and to share this excitement and tell everyone what I got. I was too embarrassed to do this and now I have to physically wear and show everyone my new things.

It is our Anniversary and Mistress Rosemarie decided that we should take a nice trip and that my main purpose was to pleasure her enormously. I was also to bring my presents because she intended to make good use of them. I packed my Suitcase including my very pretty negligee I received from her for Christmas, several other negligees so that I would look pretty for her each night and of course the new two quart enema system, new pink soap, condoms, a Bridal Magazine and of course panties, bra and pantyhose that I would wear full time for the weekend. She examined my suitcase, found it complete and off we went.

[![](http://cdpunishment.com/institute/images/2010/01/sissybilly_10-01-22-009t.jpg)](http://cdpunishment.com/institute/images/2010/01/sissybilly_10-01-22-009s.jpg)

Packed and the suitcases loaded in the car we drove off on Day 1 of our trip. Mistress Rosemarie drove as she is a much better driver then a sissy could ever be. She began to explain what would happen on our trip and I began to blush and worry already. She decided that my humiliation should start now and she had me put on a pretty women’s kerchief and tie a bow at my chin. When we passed cars I was to look directly at them. We were away from home and little chance of exposure, but it was humiliating and Mistress Rosemarie even slowed up sometimes so they could get a good look. It was humiliating. This was just the start.

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A sissy must be prompt in her assignments – Morning 3

It is Sunday Morning and I have been very busy, but still have not completed my profile. So I am once again completely dressed in the sissy girlie outfit of Mistress Rosemarie’s choosing.

I have rephrased and corrected sections of my profile and added another section. I was certainly hoping to have completed this by now, but I have one question that I must ask Mistress Amber because I am not sure how to do a link. After several months of trying to be a good sissy client you would think that I would know all of these things by now, but I do not. I quess I am still in need of more and extensive training and punishment as a sissy client.

I will, hopefully, finish my profile as soon as Mistress Amber helps me with my question.

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A sissy must be prompt in her assignments – Night Two

It is Thursday night and I am back fully dressed as a pretty sissy. This is definitely not pleasant being dressed as a sissy all evening. Not only I am making dinner for Mistress Rosemarie, but she is making me go to the Ladies Room often during the evening to fix myself – you know – fix my makeup and lipstick and fluff and straighten my skirt and blouse. It certainly is difficult being a girl and looking you best.

I have found and collected training photos and have uploaded them to my profile page. I hope to complete some miscellaneous items of my profile on Saturday and can finally go back to my normal dressing life. I hope

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A sissy must be prompt in her assignments

I was recently, well actually a month ago, assigned a task by Mistress Amber to fill out a profile set up by her and to complete it as soon as possible. Well, I got busy with other assignments and finally pushed Mistress Amber’s patience to the limit. A sissy never has the excuse of being to busy to fulfill her Mistress’s instructions.

Mistress Amber was still very understanding, which I do appreciate greatly, and did not punish as severely as I deserved. I have been directed by her to dress up completely in feminine clothing every night until I completed this task. I further disappointed Mistress Amber by not starting my task immediately last night and now I am also to wear my sissy clitty cage.

Mistress Rosemarie is delighted with this because she had warned me to get going on my assignment and she so likes me to look pretty. She now forces me to dress as soon as I get home and to stay dressed all night. I make and feed her dinner, clean up and then go to the computer. Mistress Rosemarie tells me to take my time now because she wants me to dress like this every night, but I know I must complete and please Mistress Amber by finishing my Profile.

Mistress Rosemarie laid out a pretty feminine outfit and took pictures for all to see and delighting in my humiliation.

![](http://cdpunishment.com/institute/images/2009/12/sissybilly_091214-003s.JPG)

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sissy billy’s Willful Insolence

[sissy billy][] was right when she said “[I must learn to keep my mouth shut][1]”. After reading her new standing rules she wrote “I am currently dressed and am on my way to work and already late, but I will shave my legs over the weekend in preparation for wearing my pantyhose on Monday.” Umm, yeah. Rules can take effect whenever she wants them to.

Well how about this instead: when she gets home from work tonight, instead of shaving her legs in preparation for Monday, she will shave from her neck down. Once nice and smooth, she will lock on her sissy clitty prison. It can come off on Monday, when she is ready to return to work.

Is that better? Or do I need to be clearer?

[sissy billy]: http://institute.cdpunishment.com/profiles/sissy-billy/
[1]: http://institute.cdpunishment.com/2009/11/new_standing_rule_for_sissy_billy#comment-6286

New Standing Rule for sissy billy

[sissy billy][]’s [permalink id=2728 text=’Standing Rules’] have been updated to indicate that her legs are to be shaved (or waxed or otherwise) at any point she desires to wear pantyhose.

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

sissy billy Freed from Chastity?

Back when Mistress Amber was in charge of sissy billy’s training, she put him in state of sexual deprivation (which was sometimes enforced by locking up his sissy-clitty). Now that I am in charge of her training, I have decided to lift this restriction. sissy billy will have free access to make love to her sissy clitty if she:

* Wears panties full time
* Wears pantyhose under her suit when she dresses for work
* Keeps a relief diary where she writes down all of the fantasies she has while making love

To make it fairer for sissy billy, I will even give the opportunity to choose her option on a month-by-month basis, starting with November. She can either have unfettered access till the end of the month, or will spend it chaste, locked inside a sissy clitty prison. The choice is hers.

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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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.

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