Tag Archives: enema

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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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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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 # 02 – Her Monthly “Period”

I received a Letter from my “Auntie Flo” last Saturday informing me that my feminine Monthly “period” was to begin again and it was indeed to be a horrible girlie “period” because I had missed so many.

I was instructed to prepare as I did when I had my last “period” and went to the store to buy what was needed.

Then I began to worry about how bad it would be and how much it would hurt. A Girlie “Period” is not a lot a fun. And then it began.

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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 – High Roller

I ask myself how I ever got myself into this mess. All I did was request a few months off to take care of some personal Business. My re-instatement has become long and trying. The Moral of this all is that all sissy clients of “The Institute for Cross-Dressing Punishment” should realize and accept that they are naughty and that this should never be a part time experience, but must be dealt with on a continual basis. I will think twice about asking for a little time off the next time. But then again, I never seem to learn quickly. However, back to the task at hand.

I am restarting my assigned trips to Fantasy Island. This time the script is dictated by other clients and Mistress Katzenburg.

As I approach the Mistress of Fantasy Island she informs me that she wants to go to the Fantasy Island Casino and will teach me to be a High Roller. I am whisked off by her assistants to dress for the occasion.

I am to wear a slinky dress, a large bra and forms and a matching thong. I present myself to the Mistress.

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In a Row — Alien Invasion — Maggie Rae’s Results

For our most recent assignment, In a Row 2: Alien Invasion, we were to dress up as alien invaders of Earth—very confused alien invaders I might add, with our primary tactic of invasion being a lingerie photo-shoot and the crashing of a Halloween party. I’m not sure I get it either, but that’s the story, and I’m sticking to it. In the words of the assignment:

”To dress as the buxom alien for the lingerie shoot you will be painted from head to toe with a colored cream make-up (you get to pick the color, which cannot be white), then in your largest bra (stuffed) and panties.”

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Fantasy Island – 13 “Sorority Pledge Hell Weekend”

As usual I could not make up my mind as I walked up to the Mistress of Fantasy Island. My mind, however, was made up for me quickly by the Mistress.

She asked if me if I remembered my Fantasy Island Wish about joining a Sorority. I, of course, nodded yes. Well then, she said, it is time for your Sorority Pledge Hell Weekend. I shuttered having read many articles of what they did to Sorority Girls during Hell Week. I was quickly dragged by the Fantasy Island Assistants to the Dressing Room and returned to Mistress after an hour of Sorority Girl prepping.

She complimented me about how I looked like the perfect Sorority Pledge and took my hand leading me to the Sorority House.

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Fantasy Island – 12 “A Little Girl’s Birthday Party”

As I walked up to the Mistress of Fantasy Island my mind was racing. It seemed whatever I wished for, the results of my wish were not what I thought they would be. Actually they had mostly been disasters and were truly painful and humiliating. What should I wish for?

Then I thought, how bad could a little Girl’s Birthday Party be. She dressed up in a pretty Dress and had fun with her Girl Friends and got lots of Presents.

Settled – I asked for it to be my Birthday and to attend a Little Girl’s Birthday Party in my Honor.

As usual, Mistress smiled that smile that always gave me chills and dread. Her answer, “Of Course”

Her assistants came rushing out as usual and grabbing my hand took me off to the Little Girl’s Store.

An hour later I was decked out in the prettiest lacy-est frilly Little Girl’s Party Dress. It was so little Girlish that it was humiliating. No Girl would wear it, let alone a sissy boy and not be embarrassed. I must admit though, I did like it very much and felt very Girlie in it.

I was led off into another room and as I entered all of Assistants to the Mistress yelled surprise. I had expected a lot of other little girls to play with, but all the Big Girls meant something else was planned.

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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?

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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.

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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