Tag Archives: humiliation

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 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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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.

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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Fantasy Island – Double Down

I am once again destined to travel to Fantasy Island. Assignment # 3 is my Bonus Trip – Double Down. I still remember my first trip to the Fantasy Island Casino and I know that this trip to the Casino will not be any more fun than my first trip to the Casino.

As I departed the Ferry – I was whisked away by the Fantasy Island associate Mistresses to be prepared. Instead of a sleek Dress, this time I was being taken to a private room of High Roller Mistresses and I was to be dressed in the sleaziest Peignoir Lingerie, the largest bra and forms and a matching thong. High Heels, of course and Makeup.

I was led to a not so private Bath where the clientele could walk in and out and naturally they all did to ridicule me and humiliate me. I was stripped naked and finally was allowed to submerse my self in my Bubble Bath.

It really is humiliating taking a bubble bath in front of a lot of Casino Patrons. If only my night ended with this.

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Make-Up Week for “Sissy Billy”

Last Week my Sissy had some personal issues and being the kind and sensitive Mistress I am, I relented and allowed her the week to settle her affairs.

However, as you all know, there are always consequences. Therefore she shall make-up last weeks assignments as she must also do her current week assignment.

  1. Complete her Post from Assignment # 3 – Fantasy Island High Roller Trip before going to bed tonight.

  2. Complete Assignment # 2A – Ovulation Time – this Tuesday, Wednesday and Thursday.

  3. Complete Assignment # 4 – Soap Testing designed as follows:

  • The Soap to be tested this week shall be a big white bar of Ivory.
  • Testing shall be per the previous guidelines.
  • 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. Results are do next Monday night (It is a long weekend, so she gets an extra day) or sooner.
  1. Complete this week’s Assignment # 5 – Fantasy Island trip as a Cheerleader.
  • Special Cheerleader Dress Code for a Sissy. Everything Pink. Nail Polish, lipstick, Red Stockings and heels, pink panties, pink stuffed Bra, sheer top and of course her pom poms.
  • Her Bonus trip is a punishment for causing the team to loose.
  • First a paddling until her “ass” is pink.
  • Then a Cheerleader 2 quart enema.
  • With legs tied she is to stand in the corner of the Locker Room for one hour as her enema leaks out. No Cheerleader that I know would be able to hold it for an entire Hour. This should prove embarrasing as everyone watches.
  • Last she is to suck on the practice dildo for ten minutes and then lick the cheerleader practice vagina for another ten minutes.

Make up Weeks can be exhausting and non forgiving. Since our Sissy missed last weeks assignments and requirements she shall wear panties and pantyhose every day to work this week as a punishment.

“sissy billy” – I was understanding, but I have not talked with Mistress Katzenburg this week and am not sure if she will be. Do not be surprised if she is not as understanding as I and alters your assignments.

Your Summer School Associate Mistress

“sissy billy’s” Rehabilitation Summer – Assignment # 1 – A Sissy Shaving

I confess that I have been too long negligent and lazy in being an active sissy student client of “The Institute of Cross-Dressing Punishment”. I have therefore been enrolled in Summer School of the “Institute” by Mistress Rosemarie and with the concurrence of Head Mistress Katzenburg. This was mandatory and it was made perfectly clear that I must pass or I may be expelled. I will attend this Summer School with the utmost enthusiasm and the proper attitude so that I may regain my status as an active sissy client.

So my Summer begins:

Assignment # 1 – Since I had for so long refused to comply with the many past assignments of a Clean Shaven sissy body, I am to do the following:

When I return home on Friday night I am to prepare and take a fragrant sissy bubble bath to soften my sissy skin. I am then to shave my body from the Neck down with strong encouragemnt that I at least utilize a feminine wax kit for areas of my hairy non-sissy body.

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sissy billy has been a Naughty Sissy

I have been silent too long and have not wanted to participate, but I have completely supported Mistress Katzenburg in her attempts to train my Sissy. However, Mistress Katzenburg and I are in agreement and are completely disgusted with your feeble attempts and poor attitude. With urging by Mistress Katzenburg, I will no longer be passive, but will take a more active Role in assiting Mistress Katzenburg and the Institute in your training and punishments.

silly billy has been lazy, arrogant at times, completely negligent of her duties as a sissy client of The Institute of Cross-Dressing Punishment and just plain naughty. She has broken and failed to follow so many “Rules of the Institute” that we could not list all of them. It is time for her attitude to change and her rehabilitation to begin.

Since sissy billy seems not to have enough will power of her own to follow even the simplest rules or demonstrate a proper attitude, I will give her a strict and rigid schedule to follow over the next three months. She will either complete successfully every assignment given her or I will wash my hands of her and I imagine Mistress Katzenburg my suspend her and put her in the Hall of Shame.

“sissy billy” – read your fate below in the following agenda that we have set for you and obey completely.

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Maggie Rae: The Good, The Bad, and the Pink

It has been a while since I have posted an update for The Institute, for a number of reasons—some good, some quite bad. When it comes down to it, I have broken one of the most important rules of The Institute: When a client will be out of town or unavailable for an extended period of time, they must notify the Mistresses of The Institute ahead of time. I did not do that, and I have been away for an extended period of time, during which I shirked my Institute duties. That was the bad part. The delightfully good part is that, over the past few months I have been developing a closer and closer relationship with a good friend of mine, which has rapidly become something far more special. While I was away from the Institute, I was instead with my new Mommy Venus (who is extremely eager to step up the intensity of my already humiliating and painful Institute activities) who made sure that my time away was not spent pleasantly…

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Fantasy Island – Smurfed All Night Long

As related in my previous adventure – A Smurfy Centerfold, the Smurfette’s convinced Mistress that I should stay the night and meet them in the Fantasy Island Smurf Park on the far side of the Island.

I did not like the sound of that, but as usual I had no choice and I was led by Mistress back into the Sissy Salon.

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