Tag Archives: assignment

Maggie Rae: Story Assignment 5—Hired Help

First off, I’d like to apologize to everyone—things have been a bit hectic, and I missed my usual Sunday deadline. I hope the amusement that you get from my suffering makes up for it a bit, and trust me, there was a good bit of suffering. This week’s story assignment actually managed to be less pleasant than Back and Forth, which I didn’t even think was possible. Like Back and Forth, I was again going to be transporting pennies, though this time as a restrained maid, and before I would be able to complete a penny I would need to perform oral service on a nearby dildo. Combine that with the same 1,000 pennies from the first time I did Back and Forth (which was never going to happen), and horrible consequences for failure, and you’ve got just the latest in my hellish assignments. First order of business, though, was to get dressed…

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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: 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: 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: 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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SUMMER SCHOOL SESSION # 2 – WEEK 2 – CLASS STUDY OF THE EXPERIENCES OF A “SISSY GIRL PERIOD’

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” tonight.

“SURPRISE”

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” discharge
– 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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SUMMER SCHOOL SESSION # 2 – WEEK 1 – CLASS STUDY OF THE EXPERIENCES OF A BABY

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 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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SUMMER SCHOOL SESSION # 2 – “SISSY GIRL” HOME ECONOMICS

Summer School Session # 2 – June 18, 2012 through July 15, 2012:

Week 1 – Experiences of being a Baby – Sissy Student Assignment and Requirements

  • Does not sleep in her big Girl Bed
  • Her 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, she is to go to the nursery, put on a diaper and rubber pants and baby romper set
  • She shall insert her mouth spreader to promote sissy baby drooling
  • From Monday till Friday the Sissy Baby will only eat Baby Food and Baby Formula
  • Before going to Bed she will drink 32 oz of water and accept a “Fleet” enema to make sure she experiences the feeling of being a baby

Week 2 – 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.

Week 3 – Housekeeping 101 – How a Sissy should keep Mistress’s House

  • Immediately upon returning home she is to go to the dressing Room and put on her Maids Outfit for two hours of Housework
  • Monday thru Friday – she is to complete a different Housekeeping duty each night
    o Clean all the bathroom
    o Clean the kitchen
    o Wash all her Nighties and Panties, Iron and Fold
    o Vacuum and dust all the rooms
    o Act as the waitress, standing by the door for two hours holding a tray of drinks

Week 4 – Fashion Training – Sissy Dress-up Week

  • Monday thru Friday – each night will be fancy dress-up
  • Dress will be formal gowns and Thursday will be Bridal Gown night
  • As a sissy “adult” she will practice her oral service each night
  • Ultra feminine Negligee’s required for bed
  • Relief and Slurping will be required before going to bed each Night

The “Institute” Mistress School Board has also reviewed sissy billy’s 1st Semester Records and while it’s review is not complete, it has been determined that since she is now on “Probation” the following shall be added to her school assignments. Her Progress is still being reviewed and it is anticipated that further disciplinary actions may be assigned.

Since she seems to be forgetful about her assignments and late in turning in several assignments, for the remainder of the summer, sissy billy is required to install a full time reminder that she is a sissy.

She is to obtain two dildos that can both be mounted on the wall. Each will be mounted 18 inches off the floor, next to the door leading to the garage (one on the inside, one on the outside). For the remainder of the summer, every time she enters (or leaves the house), she will

(1) Get on all fours
(2) Spend 15 seconds giving proper homage to the phallus
(3) Stand up and open the door

So, every time she goes through that door, she will practice her sissy oral servitude before going through the door. Her Mistresses think this will be a way to help her remember her place. Documentation of this shall be included in her first post and report.

Summer School – Semester One

Your First Trimester of Summer School has ended Sissy Billy. There was a great improvement in your lack of attention and effort which is commendable, but you had so far to come from your total Lack of Effort over the first part of this year.

You had 1 B, 1 C, 3 D’s and 1 F. This averages to a GPA of 1.6. Passing is a C (2.0) and therefore you are now placed on Probation.

There is a 3 week intercession before your 2nd Trimester Assignments are developed and your 2nd of 3 Summer School Sessions begin.

The Following Assignments remain in effect and/or Modified. (Subject to further Modification by Mistress Katzenburg)

• Every Friday you will continue to wear panties and stockings to work in preparation for the weekend. • For improvement in your work Ethic – Your weekend rules will be adjusted to go from 6:00 PM to 6:00 AM each night from the time you get home on Friday, Saturday and Sunday Nights. The Ladies Room is still strictly off limits during this time. A Diaper may be worn if you wish, but it can only be removed at 8:00 AM when you finish each Night. To ensure you stay well hydrated. you are to drink a 16 oz glass of water every hour until you go to sleep. You are to wear a nightgown, stuffed bra and panties to bed each night. • You will continue to experience your sissy period once per month. • You will continue to experience your sissy ovulation two weeks after your sissy period begins and will take proper precautions for three days.
• It is now the Summer Season starting June 1. Therefore you will be wearing panties every day. In honor of the “Girlie” Summer of a few years ago, thongs will be included. On Sunday night you are to lay out and photo document 7 panties, 3 normal lady panties and 4 lady thongs. You are to put these in your small lingerie draw and then with your eyes closed each morning reach in and pick one.

Enjoy the Summer, Your Assistant Instructress (Summer School), Mistress Rosemarie

Fantasy Island – After the Homecoming Loss

Oh My – yet another trip to Fantasy Island. On a previous trip I was nominated as an honorary member of the Fantasy Island Cheerleader Squad. It was not an honor for me, but a very humiliating experience. I mistakenly caused our team to loose by falling (I think I was pushed by the other Cheerleaders) onto the field causing a stoppage of play as we were going to score and as a result we lost. It was all my fault.

Now, as I got off the Ferry, Mistress smiled as she always did as the Cheer-leading Squad rushed out of the building, grabbed me and took me into the Cheerleader’s Locker Room. Today was just a practice of the Ladies Soccer Team, but they were told and remembered how I had ruined the Boys Football Game. I was told that they were looking to punish me for being such a bad Sissy Cheerleader. Girls can be so mean.

Another Fantasy Island Experience begins:

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Assignment # 4 – Soap Testing – A Continuation

Additional Soap Testing was required for previous Failures and the Testing is designed as follows:

The Soap to be tested this week shall be a big white bar of Ivory and be tested as previously. Each morning with her shower using the Ivory, she is also to clean the inside of her mouth during her shower. She shall soap up her pink soft sponge completely and shove it in her mouth for the entire shower. At night before going to bed, she shall test the Ivory as a soap-paste and brush her teeth thoroughly.

My memories of this are not good. This was the Soap my Mother and Aunt used to punish us when we talked back. They thoroughly washed our mouths out and I remember it always being terrible.

I was not looking forward to this, I hope, final Soap Test.

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Aissgnment # 2A – “sissy billy’s” Ovulation Time

I am a Sissy that is now having her monthly “Period” at a regular Interval. Mistress tells me that it is part of a feminine cycle that I now “Ovulate” each month. I did not really know what this meant and was sent to research it’s meaning by Mistress.

A Women’s Ovulation time is the 2-3 Days each month when she is fertile. It usually falls in the middle of her Menstrual Period which I have now been experiencing. It is also the time of the month when the egg falls and she can become pregnant. Her hormones are at their peak and she feels her most feminine. It is also the time of the month when she will unconsciously dress her prettiest and have her strongest feelings to get pregnant.

At this time of my sissy life I certainly do not want to get “pregnant” or get anyone else “pregnant” and Mistress is “helping” me with contraceptive protection.

As a result of obsession with Cross-Dressing and the Training and Punishments the “Institute” has assignment to me, another phase of my Sissy Life begins.

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