Category Archives: Activities

Fantasy Island – 8 “If you act like a Baby…”

The end of my last Fantasy was absolute retribution by all the other sissy clients for my power trip as a Mistress and the meanness that a real Mistress would not have shown.

I cried and screamed and yelled some very un-sissy-like words. I have to admit though that it was deserved.

Finally they brought me back to the Mistress of the Island and they themselves returned to the “Institutes’s Training Center” which was located on the far side of the Island.

The Mistress of Fantasy Island then told me that since I had acted like a Baby, then I would be treated like a Baby

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Fantasy Island – 7 ” Mistress for a Day or a Few Minutes”

As I was traveling to Fantasy Island on my next visit I was thinking about how much I had been punished and how much it had hurt and how much it was terribly humiliating.

I thought – How nice if it was I that was the Mistress and I was in charge of training and punishing the sissy clients.

The more I thought about it the more my sissy mind got the better of me. When I approached the Mistress of Fantasy Island I just blurted out that I wanted to be the Mistress of “The Institute for Cross-Dressing Punishment”

I was amazed when she just smiled and said OK.

I could hardly control myself. I followed one of her helpers to get dressed in what I thought was proper Mistress Attire. I even came up with a mask like Mistress Katzenburg’s hood. Well, not quite – it was actually a pair of lacy thong panties. In my mind it was perfect though.

[![](http://cdpunishment.com/institute/images/2011/09/sissybilly_110930-003e.jpg)](http://cdpunishment.com/institute/images/2011/09/sissybilly_110930-003s.jpg)

I was taken to the “Institute” and led into a room of sissy clients. I could hardly contain myself. I instructed one to bend over and immediately spanked her until she cried. Several others I inserted butt plugs into their sissy vaginas and issued other assignments.

How much fun was this?

Then the door opened and in walked Mistress Katzenburg. I almost fainted on the spot.

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Fantasy Island – 6 “Attending Church on Sunday”

My last visit to Fantasy Island proved to be very stressful. In hopes of a quiet and peaceful Sunday I thought I would make a wish to just attend Church which would give me an Hour or so of peaceful quiet and to think about my life as a sissy of “The Institute for Cross-Dressing Punishment”.

The Mistress of the Island told me she thought that was an excellent idea and asked if I wished to attend Church with her. Not thinking anything could be wrong with her invitation, I accepted. She called one of her girls and told me to go with her. Church on Fantasy Island was not a place that you wore pants to. She said her girl would pick out a nice dress for me.

I thought that was a great idea. I do love to wear pretty dresses.

After an hour of fixing I was presented to the Mistress wearing stockings, white heels and a feminine conservative white dress. She also gave me a scarf (Ladies always wear something on their heads to Church) and Gloves (Proper Ladies also wear gloves to Church). Mistress smiled and told me I looked Lovely.

[![](http://cdpunishment.com/institute/images/2011/09/sissybilly_110929-012e.jpg)](http://cdpunishment.com/institute/images/2011/09/sissybilly_110929-012s.jpg)

We walked to Church with several other Ladies from the Mistress’s Office and it was a delightful Sunday Walk. As we turned up the Church Walk I noticed for the first time the name of the Church.

The First Women’s Church of Fantasy Island

I should have thought something strange with the name, but did not. I entered talking with the other Ladies.

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Fantasy Island – 5b “The After-Party”

My First Prom was all that I wished for or could expect. But, as often happens at a Girl’s Prom, things take an unexpected turn.

I apparently passed out after drinking too much wine. I am told that I passed out on the Bed and what came after was a Dream … or Was it?

[![](http://cdpunishment.com/institute/images/2011/09/sissybilly_110928-001e.jpg)](http://cdpunishment.com/institute/images/2011/09/sissybilly_110928-001s.jpg)

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Fantasy Island – 5 “My Prom Night”

It has been my dream to be invited to a Prom and to wear a pretty feminine Prom Gown with all the accessories. A full flowing Pink Prom Gown with a full Crinoline Slip and Pink High Heel Shoes. On this visit to Fantasy Island I asked the Head Mistress to help my Dream come true.

I was quickly scurried off to the Bridal and Prom Gown Salon to pick out a scrumptious feminine Prom Gown and start me on my way to attending my first Prom as a Girl.

I was so excited when I emerged from the Women’s Salon in the prettiest Prom Gown and fresh from the Beauty Salon where my hair had been done and makeup applied. They even did my nails in the prettiest pink nail polish. I was so excited.

I was then escorted to the Prom and at the Entrance had my picture taken for my Girlie Album.

[![](http://cdpunishment.com/institute/images/2011/09/sissybilly_110927-021e.jpg)](http://cdpunishment.com/institute/images/2011/09/sissybilly_110927-021s.jpg)

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Fantasy Island – 4 “Being a Little Girl” – Part 1

I have always wanted to be a Little Girl. Little Girls always have a lot of fun and they get to dress up so Pretty. I entered Fantasy Island dressed as a pretty and feminine Girl and asked if I may be a Little Girl with no Worries.

[![](http://cdpunishment.com/institute/images/2011/09/sissybilly_110926-012e.jpg)](http://cdpunishment.com/institute/images/2011/09/sissybilly_110926-012s.jpg)

Then the Mistress of the Island looked me straight in the eye and with a smile, told me I would have no worries, but that I must start at the begining. Now where do Girls start. Naturally they start as Little Baby Girls.

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Fantasy Island – 3 “Director of Nursing”

At one time I thought how great it would be to be a Director of Nursing. Even better the Director in a Private Clinic where there would be no regulations. I would be the Boss of all those Women and would be able to get back at all those women who did not understand me and always seemed to be domineering and dominant over me.

So, on this trip to Fantasy Island, I said that I wanted to be the Director of Nursing of a Private Women’s Clinic of only Female Doctors and Nurses. I was granted my wish and showed up for my first Day of Work as Director of Nursing. I even dressed appropriately as the Director of Nursing. White Blouse, pale pink Skirt and a Red Crinoline to add a feminine touch, stockings and white 2″ High Heels.

[![](http://cdpunishment.com/institute/images/2011/09/sissybilly_110925-014e.jpg)](http://cdpunishment.com/institute/images/2011/09/sissybilly_110925-014s.jpg)

A tough lesson to learn when you visit Fantasy Island is to be very specific in what you wish. Mine did not turn out the way I thought it would.

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Fantasy Island – 2 “A Pajama Party”

From the time I was young I always wanted to go the Girl’s Pajama Parties. They always seemed like they would be a lot of fun. I would hear my older Sister talk about the Pajama Parties she went to and how all the girls would wear pretty, frilly, lacy sexy Baby Doll Negligees. When my Sister had her Pajama Party I peaked and when I saw all her girl friends wearing those feminine Baby Dolls, I wished from that day to this that I would be invited to one. It never happened, since Pajama Parties were only things that girls did. I was so Jealous.

Naturally, when I had the opportunity to travel to Fantasy Island one of my first wishes was to attend a Girl’s Pajama Party. I was soon to regret my wish.

Mistress bought me a very feminine frilly red Baby Doll Negligee and frilly lace Panties. I got very excited about going to my first Girlie Negligee Party.

Until …………..

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Fantasy Island – 1 “A Maid To Serve my Mistress”

If I were to visit Fantasy Island I would want to serve my Mistress dressed in my prettiest Pink Maid outfit and please her with cleaning the house.

But first before I leave for Fantasy Island I should explain. At the beginning of the Summer I was looking at a very busy schedule with Work and Personal commitments. I asked Mistress Katzenburg to grant me a leave of Absence to fulfill what was required of me. She was kind enough to grant me this request, but I knew there would be consequences. And there are. I have requested reinstatement in “The Institute for Cross-Dressing Punishment”.

There are some home assignments and naturally a dress code. I am fulfilling this as I type. Of Course it will not be pleasant, but I deserve whatever is assigned me for being a Cross-Dressing Sissy, no matter had bad or disgusting it may be.

Also, I am to visit Fantasy Island once a day for the next fourteen days and each day I am to live out a new sissy Fantasy and post it for all to see and to be humiliated for my actions.

Today I am a Maid performing whatever is required by my Mistress.

[![](http://cdpunishment.com/institute/images/2011/09/sissybilly_110922-015e.jpg)](http://cdpunishment.com/institute/images/2011/09/sissybilly_110922-015s.jpg)

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Geek Girl: It’s a Maid, Maid, Maid World

As I sit awkwardly here writing this—awkwardly as I’ve been sitting in a wet and messy diaper for the better part of five hours—I know I’m rapidly approaching the end of my assignment. The Geek Girl series of assignments have been quite unpleasant up to this point (and I’m not expecting them to get any easier as I go—it would be nice though), and this assignment was no different. If you are one of the hopefuls applying to The Institute, know that fates similar to this await you—you have been warned. Warnings aside, however, on to what has been my quite unpleasant morning, it’s a Maid, Maid, Maid World after all…

>You are to get dressed as follows and remain dressed until your time is up. You should pick a period where you have enough free time, because stopping your assignment will mean repeating it. Also, changing your eating or bathroom habits in preparation for this assignment is not allowed.

>Dress is very similar to Eight Legged Clean Freaks and consists of:

>*A super stuffed diaper.

>*Standard bra and forms

>*Nylons

>*Wrist and ankle cuffs

>*A black garbage bag fashioned into a maid’s dress (with a belt and white towel for an apron).

>*Hair in dual pony tails

>Once you are dressed, you are to clean your apartment from top to bottom, until it can pass a white glove test.

>Evidence:

>*Once every two hours during the entire assignment, you will submit a picture of your current condition.

>*Once your apartment is clean, you will submit to me a video tour of all areas of your apartment as proof of completion. This will be used to judge whether or not you pass.

>Your assignment length is determine by the following rules:
>1. Your assignment will not be over (and you cannot get undressed) until you have submitted the walkthrough video and made a post on The Institute website.
>2. The minimum assignment length is 36 hours.
>2b. The minimum assignment length will be considered to have been met once you stew is a messy diaper for at least 6 hours.
>3. You can change your diaper as often as you would like, but each change adds six hours to the minimum assignment length.

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Maggie Rae: Babyface II, Part II

Way back in January, around the time I was making the ill-planned choice to fail my initial reinstatement assignments, I never really thought it would ever get this far. Truth be told, it was long enough ago that I have no idea what I was thinking, but it was my decision and I’ve done my best to live with it. Nearly six months, a long list of assignments, and the first of two Babyface repeats later, I finally found myself staring at the last of the series—one last and final repeat of Babyface to go and the long, painful, humiliating chain would be complete. This repeat would be different, however, as it would be the first and only of the three that Ms Lisa would not be administering, meaning it was all on me to make good on my promise to make this punishment miserable and humiliating enough to satisfy the last of my obligations. I’ve never found it easy to create punishments for myself, however this time I feel that I managed well enough to put this whole mess to bed, once and for all.

And so, without further ado or delay, the last in my long series of reinstatement obligations and the completion of Babyface II…

![][BF2P21s]
[BF2P21s]: http://cdpunishment.com/institute/images/2011/06/maggierae_110608-001s.jpg

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Maggie Rae: Babyface II, Interim

Over the past month, I have been diligently completing Babyface II, my most recent punishment, as penance for my shortcomings during my reinstatement into The Institute. As I’d mentioned in my last post, Babyface II consisted of two repeats of the initial assignment—unpleasant, but by no means terrible. Together, the two repeats took up nearly two full days—two days of a month long punishment. The rest of that interim period has been what I considered the real punishment. As the punishment dictated, I spent at least 10 hours a day diapered, at least 14 hours a day in my extremely heavy bra and forms, and while I fortunately escaped any additional “tasking”, I still had the intense summer heat to make everything just a little bit worse. Through the course of my 27 day punishment, I went through nearly three packs of diapers, found myself sitting in far more wet diapers than I would have liked, and on a few especially unfortunate occasions, I found myself going to bed and waking up in a thoroughly messy diaper—all experiences that I could really do with avoiding in the future…

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Maggie Rae: Babyface II, Part I

Over a month ago, when I was still in the midst of my reinstatement proceedings, Mistress Katzenburg brought to my attention that I had agreed to recomplete the [Babyface](http://institute.cdpunishment.com/2010/07/babyface) assignment as a part of the [reinstatement option I’d chosen](http://institute.cdpunishment.com/2011/03/the_actual_return_of_maggie_rae). I was not terribly keen on the concept, and tried to make a deal to avoid it—I would submit to a reader poll to decide my fate on the repeat. If people voted my way, I would avoid the repeat altogether; while if lost, I would accept my punishment tenfold. I didn’t think it could come to it, but I ended up losing in the polls by 20 votes, and so began the saga of Babyface II.

Babyface II was a direct extension of the original punishment that included two repeats of the original punishment, with a 20+ day punishment time between them for the 20 votes that I lost the poll by. Officially, the punishment was as follows:

>Babyface II will begin the same way as the original–as described in the original post. The changes Ms Lisa made are OK–and she is under no requirements to have this one be the same.

>http://institute.cdpunishment.com/2010/07/babyface

>Since you lost by 20 votes, after this has been completed, the following daily lessons will be enforced.

>0) You will continue to be shaved at all times.

>1) You will be dressed for bed between the hours of 8pm and 6am. This will include your standard forms, footed jammies and diaper. No change will be allowed during this time, so it should be a good, thick diaper.

>2) Diapers and a bra are to be worn any time you leave the house. Panties and a bra will be worn at all other times (except as specified in these rules).

>3) You will spend at least four hours of each *day* (i.e. when you are not dressed for bed) in your forms.

>4) You will be available at all times for any tasking your Mistress requires. She will ask you, so be sure to inform her you are available.

>5) After twenty nights have elapsed, you may petition your Mistress to repeat the event that started off this assignment and finally end the assignment. On the morning after the 20th night, rule #3 above will change to “all the time you are at home”.

With the poll closed and my fate decided, I set off to accept what I’d brought on myself—a month of extremely unpleasant punishment…

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A Summer Kickoff Weekend for a naughty sissy

This all started out rather harmlessly about a month ago. I had been particularly rude to Mistress Katzenburg and even though I had apologized profusely expressing my sincerest regrets, I was wrong and Mistress was right (as she always is) and I deserved to be punished and given an assignment.

I was surprised at how simple the assignment seemed to be. I was to find several recipes for making of fake cum. Sounds rather simple, does it not. I searched and searched the internet and really only found two. I unfortunately was taking my time and not corresponding with Mistress about my difficulties. As you all know, that is a real no-no.

Last week I guess Mistress Katzenburg had enough and in concert with Mistress Rosemarie, decided that since it was summer that it was only appropriate that this sissy start the summer off right with a “Sissy” Weekend.

Oh My, did I wish I had been more responsive with my simple assignment.

My assignment of finding the “FAKE CUM” was withdrawn. I am sure, however, that it will surface again as Mistress Katzenburg never forgets any failure of mine and they are often revisited in a much harder form.

I was to find a nice sissy e-card on the internet and write a private sincere apology to her.

I was also to wear a very stuffed diaper and extremely stuffed bra for a 12 hour period for one night of the weekend without changing. As most of you know this is always a disgusting assignment.

Also in honor of Mistress Amber’s Summer of Panties two years ago when I had to wear feminine and pretty thongs to teach me a lesson, I would be required to wear a thong and bra when at home until I completed my post.

The rest of the weekend would be filled with little fun assignments devised by my Two Mistresses.

I was to document on an hourly basis to ensure my compliance. I dug out all of my prettiest thongs.

[![](http://cdpunishment.com/institute/images/2011/06/sissybilly_110604-003t.jpg)](http://cdpunishment.com/institute/images/2011/06/sissybilly_110604-003s.jpg)
[![](http://cdpunishment.com/institute/images/2011/06/sissybilly_110604-005t.jpg)](http://cdpunishment.com/institute/images/2011/06/sissybilly_110604-005s.jpg)
[![](http://cdpunishment.com/institute/images/2011/06/sissybilly_110604-007t.jpg)](http://cdpunishment.com/institute/images/2011/06/sissybilly_110604-007s.jpg)
[![](http://cdpunishment.com/institute/images/2011/06/sissybilly_110604-013t.jpg)](http://cdpunishment.com/institute/images/2011/06/sissybilly_110604-013s.jpg)

An so a sissy’s summer weekend started

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sissy billy’s Final Soap Test Analysis

There is no more Soap Testing. This sissy is so Happy and I hope that my efforts and my punishment discomfits can be of assistance to all in picking out the proper soap for them to use as a sissy.

After several weeks of thorough Testing and even an added week of Testing to Test a particularly Girlie Smelling Soap, the Results are in and tabulated. All that remains is to pick a Winner which will be difficult. The added dilema is that the Winner may be used on myself and others in the Future. I will try to be fair and unbiased and not to think about my future possible discomfit.

The First assignment was to purchase appropriate Soaps for Testing among all the available feminine Soaps.

Camay (My Pink everyday Soap), Olay (Age Defing), Caress (Velvet Bliss), Dove (Pink Rosa) and then the added Japanese Cherry blossom were chosen for testing.

[![](http://cdpunishment.com/institute/images/2011/05/sissybilly_110514-001t.jpg)](http://cdpunishment.com/institute/images/2011/05/sissybilly_110514-001s.jpg)
[![](http://cdpunishment.com/institute/images/2011/05/sissybilly_110514-008t.jpg)](http://cdpunishment.com/institute/images/2011/05/sissybilly_110514-008s.jpg)

The Testing then was started under strict and documented criteria.

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