Tag Archives: assignment

“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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“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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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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Winter Camping All-Client Punishing Sleepover

Between Thursday and Saturday night of this week, all clients are required to attend a punishing sleepover. The sleepover is to last a minimum of eight consecutive hours. Required dress for the night includes:

  • Panties
  • Pantyhose
  • Nightgown
  • Bra and Extra-Large Breast Forms
  • Ankle Cuffs, Ankles locked together
  • Wrist Cuffs, wrists locked together
  • Blindfold
  • Earplugs
  • Hood

In addition to the panties in the first bullet, you are free to wear a diaper over them. The panties are not optional. Just know that you are not allowed to get up before the eight hours have elapsed, so wearing a diaper (or two or four) may make the assignment completable without making a mess of your bed.

Speaking of beds, since this is a winter camping punishing sleepover, sleeping in your own bed is not allowed. If you follow in the true spirit of winter camping — outside in a tent — you will be allowed any type of bedding you would like. If you stay inside, you will be sleeping directly on a hard surface floor with your pillow and blankets to keep you company. If carpet it more your style, then you are allotted one thin blanket.

Extra points are available only if you have someone else tuck you in. (They will have to bind you tightly enough so that you cannot get up in the morning until they release you and they will be responsible for taking pictures tat you could not possibly take.)

Sleep tight and ensure the pictures are in the dropbox before Sunday night. No need to make a full post–you can have sweet sissy dreams. In addition to the unmodified pictures, also upload two pictures (in both t and s size) which you think best reflect your situation and a text file with a short description of why your night was the most punishing.

Fantasy Island – A Smurfy Centerfold

We each have a driving force behind us. A Sissy Submissive like myself is weak and needs guidance. I am fortunate to have Mistress Rosemarie who gives purpose to my life and guidance. As usual, it was her who decided that I have been lacking in attitude and needed a big push. With a Stern voice she told me to get in the car and as we drove to the dock she lectured me continually on my bad attitude. She told me that I better shape up and start behaving like a proper sissy client again of “The Institute for Cross-Dressing Punishment”.

I got out of the Car and headed to the Dock to board the boat for Fantasy Island. Passenger of one headed for her new adventure and what was sure to be my justified punishment.

As the boat neared Fantasy Island I could see the Mistress of the Island smiling as usual and waving to me. I dreaded how happy she always was and how very unhappy I ended up with my adventures.

She smiled as I curtsied as was appropriate for a sissy to do as she approached a Mistress. She told me that Mistress Katzenburg had told her how much I liked Smurfs and Smurf Movies. On this trip I was to have the honor of being the lead Actress in a Smurf Photo Shoot.

Her assistants as usual whisked me away to the Sissy Dressing Room.

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Maggie Rae and the White Slime: Cleaning Up After sissy billy

Some time ago, well before I fully completed my return to The Institute in fact, sissy billy was given a very easy assignment. That very easy assignment never got completed, faded into the background, and disappeared for a good long while. Nothing ever permanently disappears at The Institute, however, and even sissy billy made the prediction that it would return. “I am sure, however, that it will surface again…” he said, and so very right he was. It was in my lap, however, that this assignment was dropped this time around, and if last time this assignment was just to find a recipe, then I’d say it came back much larger than before. This time, I not only had to find recipes, but had to test them on myself as well. Thanks, sissy billy.

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Invasion of the Sissy Witch from OZ

The Wizard of Oz had called the Wicked Witches to an emergency Meeting and as a Sissy Witch I was commanded to also attend. The Wizard told the Wicked Witches that he needed some place to send all the Munchkins which were annoying the hell out of him.

He told them to conquer another world somewhere over the Rainbow and to do it quickly.

Now none of the Wicked Witches really wanted to get their green hands dirty (they would rather taunt the Munchkins), they decided that the Wicked Witch of East would take me as her Witches Army thinking that with her powers and my ugly looks, the people of this other world would quickly give up.

So I dressed accordingly in my prettiest ugliest Witch outfit and we left for earth.

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In a Row 2: Alien Invasion

As a followup to the original In a Row assignment, I require this assignment of all clients. In this assignment, you will acts as the president of an alien race of humanoids set on enslaving the earth. You set up a plan where you will have a lingerie shoot showing off your buxom, but oddly colored, human form which every newspaper will want to run and then meet up with others from your invasion at the largest halloween party in the world (where you will all blend right in).

Unfortunately for you, after leaving the lingerie shoot, you follow what you think are a bunch of people dressed as ghosts. Instead of ghosts going to the party, it turns out to be a klan rally and they don’t take kindly to people of color. You are captured and taken prisoner, where they decide the best they can do is to humiliate and torture you.

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Fantasy Island – 14 “Here Comes the Bride”

Since this was supposed to be my last visit to Fantasy Island and it had always been my life-long dream to be a Bride, I had planned to ask the Mistress of Fantasy Island if I could please be a Bride.

Not knowing really what to expect from my extension of visits, I figured that this might be my last free wish. So I decided that I should stick to my original planning.

“Mistress – Please grant my wish to be a Bride and may I dress up as the prettiest frilliest Bride ever and attend a my Wedding.”

As always – she smiled and granted my Wish. I was whisked off by her assistants to the Bridal Salon to prepare for my Wedding.

As I came from the Bridal Salon Mistress said I looked Lovely. Then Mistress walked me to the steps of the Church and as the Doors were opened and the music started I could see the Church was packed with My Mistress’s friends. I was somewhat embarrassed to walk down the isle as a Bride, but it was my dream and I stepped out with courage.

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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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All-Client Punishing Sleepover

Between Thursday and Saturday night of this week, all clients are required to attend a punishing sleepover. Required dress for the night includes:

  • Diaper
  • Pantyhose
  • Nightgown
  • Bra and Large Breast Forms
  • Ankle Cuffs, Ankles locked together
  • Wrist Cuffs, wrists locked together
  • Blindfold
  • Earplugs
  • Hood

Sleep tight and ensure the pictures are in the dropbox before Sunday night. No need to make a full post–you can have sweet sissy dreams.

Update: In addition to the unmodified pictures, also upload two pictures (in both t and s size) which you think best reflect your situation. Additionally, upload a text file with a short description of why your night was the most punishing.

Fantasy Island – 11 “Sorority Girl”

When I was in school I often watched the Sorority Girls and would envy them. They looked like they were having so much fun. I wished back then that I could have joined a Sorority. Even then I wanted to wear the outfits that Sorority Girls did and do the fun things they did.

Here was my chance. When the Mistress of “Fantasy Island” asked what my wish would be, I said that I wanted to be a Sorority Girl.

She smiled and told me that at the local school on the Island there was a Sorority and by Luck, they were having final interviews that night and would tell the girls then and there if they were in the Sorority. I was so excited at the opportunity of finally being a Sorority Girl.

The Mistress said that each year they do take one boy as a special case and if I was sure, she thought she could arrange it. Tonight was the formal interview, so she suggested that I go with her assistant to the Fantasy Island Store. I found a nice pair of slacks, a button down collared shirt and even put on a tie so that I would impress the Sorority Girls.

I returned to the Mistress and after she complimented me on how handsome I looked led me to the Sorority House.

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“Fantasy” Island Continues

Since sissy billy was unable to finish her series of Fantasy Island posts and complete her return to The Institute, I have decided to give everyone the required opportunity to help her finish. In addition to finishing the four trips that she has left on her own, she will be doing one for each client of The Institute (plus a bonus one from me for each client that responds). And if the clients choose not to respond–do you really want to find out?

All clients below are to email me a title and description of sissy billy’s trip to Fantasy Land by Saturday the 15th.

Client Trip Bonus Trip
Bitch Baby Brianna Montana Salon Day  
Maggie Rae High Roller Double Down
Stacee Skye A Smurfy Centerfold Smurfed All Night Long
pie clown Hometown Cheerleader After the Homecoming Loss
sissy baby jamie Rubber Mannequin  
sissy billy Spa Day  

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


*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.


*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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