Maggie Rae: Chapter 4, The Reason for the Season

After [last week’s]( grueling assignment, my prayers have been answered and it seems like this week will be a bit of a lull. While I can’t say that the assignment that I’ll be facing this week is all that pleasant, it does seem a lot easier than last week. While this week’s story does include some ominous lines, for the time being it seems like the worst is over. Remember to check back this Sunday to see the write up from this week’s assignment, [follow]( [us]( on [twitter](, and consider applying to [join The Institute yourself](

Now, without further ado, this week’s chapter…

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Maggie Rae: Story Assignment 3—Back and Forth

Let me tell you about the worst night I’ve had in a while, and bear with me because I haven’t had nearly as much sleep as I should have. [This week’s story assignment]( looked bad on its face, many of them do, but it’s not until you’re well into it before you realize exactly how terrible it is. The principle sounds simple enough—my assignment was to transfer pennies one at a time from a cup in one room in the house to a cup in another, with increasingly unpleasant additions as I went. Now, my place isn’t that big, and even spread out as far as possible, there were only about 15 steps between cups—not awful you say, that’s 30 steps per penny. Well, allow me to show you how wrong you would be…


Like most assignments, however, I started by laying out everything I would need beforehand… Ominous, isn’t it?


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Maggie Rae: Chapter 3, Back and Forth

We’re in to week three of my story assignment series, and Mistress Katzenburg has come up with a doozy this week. I’m not looking forward to the assignment coming up in the next couple days, which is pretty clearly spelled out in the story. Be sure to check back this Sunday to check out my fresh misery, and next week where things can only really get worse—I’m sure you can’t wait. For now, however, you’ll just have to make due this this week’s chapter…

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Maggie Rae: Story Assignment 2—Fire Down Below

Tonight’s assignment marks the end of the second week of my assignment story series—my ongoing training based off Mistress Katzenburg’s ongoing story. This week, Sean finds himself in a [precarious (and painful) position]( While the assignment wasn’t terribly difficult or (thankfully) humiliating this week, it was both time consuming and very, very painful. My assignment took place in two parts—first, I was to shave from the neck down, which just takes forever when you’re as hairy as I am, and second I was to masturbate with Icy Hot—bringing myself to the edge multiple times, but never cumming. While it was an extremely painful assignment, it did at least distance itself from last week’s humiliation.

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Maggie Rae: Chapter 2, A Precarious, Precious Position

Today marks the second week of the [new story series](, here for your reading pleasure. Don’t forget to check back with us on Sunday for the assignment based off of this chapter, as well as next Wednesday for the next chapter in the story. What will happen next? I have no idea, and I’m really not looking forward to finding out—this week’s chapter sounds unpleasant (read: painful) enough. For more from The Institute, be sure to follow [@cdpunishment]( (still not sure what that’s going to end up being) on Twitter.

Also, if you think you’ve got what it takes to be a client, consider trying to [Join The Institute]( for yourself. If you do end up going that route—remember: spelling, grammar, and punctuation are important… No one like an illiterate sissy.

Now without further delay, this week’s chapter…

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Maggie Rae: Story Assignment 1—A Reckoning

As [previously mentioned](, tonight marks the beginning of my story assignment series—every week Mistress Katzenburg will be adding a new chapter to the overall story and I will be assigned a special assignment based on the week’s chapter. This being the introduction week, I got off relatively unscathed, but it was still an extremely unpleasant (and painful) experience. I know that as the story continues, my assignments will only get more and more humiliating—good for all of you, not so good for me. I don’t even want to think of where I’ll be in a month’s time…

Enough about worrying about the future though—here are the results of this week’s assignment.



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Maggie Rae: So It Begins…

I am beginning a new saga here at The Institute—starting a new year of training and assignments, punishments and torments I don’t even want to think about. My new training will take place in the form of a serial story, written by Mistress Katzenburg. Each week, a new chapter will be added to the story, and with it a new, humiliating assignment for me to perform for the pleasure of all of you. Typically, the new chapter of the story will be posted during the middle of the week—often Wednesday, but Tuesday and Thursday postings will not be uncommon either. Once you’ve seen the story, check back on Sunday night to see me put through another humiliating ordeal as I complete the week’s assignment. How long will my new training last? It’s hard to say, but it doesn’t look like it will be ending anytime soon…

Now, without any further delay, our story begins…

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Maggie Rae: Violent Femmes

Nearly a week ago, we active clients here at the Institute received a warning that a new assignment was coming down the tubes, and that it would be based on the timeless music of the Violent Femmes. While we were all asked what our two favorite Violent Femmes songs were, Mistress Katzenburg’s two favorites were ‘36-24-36’ and ‘Dance, M.F., Dance’. From that alone, I knew that nothing good could come of this assignment, but yesterday I found out just how bad it would be.

Since none of us had 24” waists, we were first to figure what our bust and hip sizes would need to be to maintain the same proportions. It turned out that I would need a 63” bust and hips, which meant a bra with my biggest forms and a super-stuffed diaper (since it seemed like it wouldn’t take too long, I omitted the diaper and just super-stuffed my plastic panties—bad choice). After I was dressed I had to make a video for Mistress Katzenburg following the directions of her second favorite song, ‘Dance, M.F., Dance’—you can imagine just about how well that went, in a bra stuffed as full as mine was. If she decides to post the video, then you’ll get to see it as well.

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Maggie Rae: Life Imitates Art

About a week ago, I had a spare afternoon where all my work was done and I had no other real outstanding obligations. To pass the time, I decided to work on my art (I’m not really an artist, but I like to mess around with it none the less). One thing led to another, and before I knew it, I’d finished my first picture in a long time. Wanting to share it, I posted it to Twitter, where it caught the eye of Mistress Katzenburg. Having no outstanding assignment at the time, she decided that my next assignment would be to duplicate the picture that I had drawn. Given how unpleasant the subject matter I’d drawn was, my heart sunk a little, but I pledged to finish my new assignment as quickly as possible…

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Maggie Rae: Full of Shit

A long, long time ago I was given an assignment in response to some unnecessarily mean things that I’d said. At this point, I honestly can’t remember what they were, but they more than warranted a response from Mistress Katzenburg. That assignment was the originally named, Full of Shit. I was to find a recipe that would leave me looking like I’d been covered in shit, post the recipe, then make up a large batch, dress up like a baby, and cover myself in it for the enjoyment of all of you. That assignment unfortunately never happened—life gets in the way, things get put off until later, and before you know it, it’s been five months. I should have known better than to put it off, and I’m sure I’ll pay for it in the long run, but better late than never.

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missy sissy

There are sometimes that a response comes in and I just can’t help but post it (so everyone can see the humor in it). missy sissy seem so excited to see what was offered:

> Mistresses: You are superior to me in every way. just a simple sissy slut whore here. Please please look at my pathetic sissy ass for you amusement. i promise to attempt to please You in any way a sissy can

But, when she saw what she would have to do just to obtain the application, she bolted very quickly:

> Thank you again for acknowledging this lowly scum. sissy has realized that she has no balls, and cannot fulfill your needs at this time.
> thislut is just another wanna-be sissy bitch. please forgive me for wasting your time again aplogies,

It’s probably just as well–I hate typos.


The Second Semester is dedicated to a class curriculum of “Sissy Girl” Home Economics. It is a learning experience of what to expect as a Sissy Girlie Cross-Dresser in preparation for readmission to “The Institute for Cross-Dressing Punishment”.

My second week course entails the experiences of a “SISSY EXPERIENCING HER PERIOD”.

The following course requirements are:

This week will be devoted to her “period” week. Learning to become a young Lady is critical to her Sissy Development. This course is under the guidance of “Auntie Flo”. “Auntie Flo” will send her reminder and daily assignments prior to the School Week. Attached is the “Period” Memo I received from “Auntie Flo”

Hello Sissy Billy,

I know that you believe your Monthly Menstrual Cycle is not due to start till Thursday, but
Honey, sometimes it can come early and suddenly. So, unexpectedly it you will start your “Period”


Tuesday, June 26, 2012

Tonight without warning it starts. Take 3 feminine laxatives immediately and drink a large glass of water every hour until 9:00 PM. I would suggest you put a Sanitary Napkin in your panties right away.
Your cramping will start at 9:00 PM today. You will accept a full enema and refill each time you must go to the Ladies Room. Your nipples will also swell and throb. Nipple Pins for 15 minutes every hour. Continue
to 11:00 PM and then you can try to go to sleep.

You should set your alarm for 5:00 AM and start your enema simulation of severe cramping for an hour before you may then start to get dressed for work. Since you feel bad, eating lightly is a must. You may eat you normal food, but I strongly suggest you help digest your Food by taking a tablespoon of Castor Oil with it.
You better wear a Sanitary Napkin to work tomorrow.

Wednesday, June 27, 2012

A Bad Day today. Cramping is bad – Drink water all day. This will continue Menstrual Bloating. You should wear maxi pads for the day changing if necessary. Tonight is more cramping enemas for the entire night. When the cramps are too much you may go to the Ladies Room. However, you must refill and re-administer another 2 Quart Enema as usual. Repeat the process until you go to bed.
– Your Sanitary Pads must be smeared with my special “Period”
– Attach clothes pins for 15 minutes before going to sleep.
– Normal Food is OK, but it must be taken with Castor Oil as well as feminine Laxatives before going to Bed.

Thursday, June 28, 2012

Your cramps are stopping, but your Sanitary Pads must be smeared with my special “Period” discharge and you should insert Tampons all day.

Friday, June 1, 2012

Your period is ending, but continue to wear protection today.

Good Luck my young Sissy Girlie Lady.

Best wishes,
Auntie Flo
See you next month.

And So, on Tuesday my “Period” began. It is true that I have been having my “Period” for a number of months now, but it is humiliating to tell about it in a post.

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Back to School. I have finished Summer School Semester # 1 and I am now about to start Semester # 2. The Session Break was too short.

This Semester is dedicated to a class curriculum of “Sissy Girl” Home Economics. It is supposed to be a learning experience of what to expect as a Sissy Girlie Cross-Dresser in preparation for readmission to “The Institute for Cross-Dressing Punishment”. This Semester looks like a lot of difficult Sissy Courses and I am already behind in starting my first course and further behind in posting my course report.

My first week course entails the experiences of a “SISSY BABY”.

The following course requirements are:

– The sissy student must not sleep in her big Girl Bed
– The sissy student’s Bed shall be the Tub in Mistress’ Bathroom (it is about the size of a crib)
– The sissy student shall setup the Tub with appropriate Bed Padding, Baby rubber sheeting and little Baby sissy Girl sheeting. She will sleep in this each night
– Immediately when arriving at home, the sissy student is to go to the nursery, put on a diaper and rubber pants and baby romper set
– The sissy student shall insert her mouth spreader to promote sissy baby drooling
– From Monday till Friday the sissy student will only eat Baby Food and Baby Formula
– Before going to Bed sissy student will drink 32 oz of water and accept a “Fleet” enema to make sure she experiences the feeling of being a baby

As a result of this sissy student failing to start the course on time and missing the first two class days, this first week class will be extended another week with requirements not completing until July 1.

With reluctance and trepidation, I went to my first class of Semester 2.

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sissy billy’s Fantasy Island

In the beginning, [sissy billy][] assigned 14 trips to Fantasy Island:

Count | Trip
:—– | :—————————————
1 | [A Maid To Serve my Mistress][1]
2 | [A Pajama Party”][2]
3 | [Director of Nursing][3]
4 | [Being a Little Girl – Part 1][4]
5 | [My Prom Night][5] and [The After-Party][5b]
6 | [Attending Church on Sunday][6]
7 | [Mistress for a Day or a Few Minutes][7]
8 | [If you act like a Baby…][8]
9 | [The Bridal Shower][9]
10 | [A Ballerina][10]
11 | [Sorority Girl][11]
12 | [A Little Girl’s Birthday Party][12]
13 | [Sorority Pledge Hell Weekend][13]
14 | [Here Comes the Bride][14]


Since she was unwilling to finish these trips on time, she was given a total of twelve more assignments, one from each of the current clients plus a bonus assignment. (The trip listed in italics is different than proposed, because the original was a duplicate.)

Client | Trip | Bonus Trip
:————————- | :————————– | :———
Bitch Baby Brianna Montana | Salon Day | Fashion Model
[Maggie Rae][] | [High Roller][P2_] | [Double Down][P2B]
[Stacee Skye][] | [A Smurfy Centerfold][P3_] | [Smurfed All Night Long][P3B]
[pie clown][] | [Hometown Cheerleader][P4_] | [After the Homecoming Loss][P4B]
sissy baby jamie | _Giant Baby_ | Giant Helpless Baby
[sissy billy][] | Spa Day | For Mistress Rosemarie

[Maggie Rae]:
[Stacee Skye]:
[pie clown]:
[sissy billy]:


Now, she has until the end of her second summer semester to get them finished.

Or else.

Sissy Summer Dress Code – Panties, Thongs and Diapers

Sissy Summer officially started June 4 and to my dismay I was once again asked (Required) to participate. The “Girlie” Dress Code this summer was an alternating blend of Panties and Thongs every day. My weekend Dress Code remains in affect to my continuing discomfit.

I collected Panties (three) and Thongs (four) for each day of the week and laid them on the Bed for display and inspection by Mistress and then put them in my lingerie draw for use during the week.


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