Tag Archives: sissy-baby-jamie

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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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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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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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 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  

sissy baby jamie: Big Hairy Baby

Since sissy baby jamie has been crying for a punishment, and it overdue, here it is. Since I noted from her submission pictures, she was much to hairy for a sissy baby, she will shave from the neck down. Then she will repeat her failed assignment, but as a punishment this time.

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