Tag Archives: holiday

sissy billy: Happy New Year

Over the years it seems that I have had a difficult time in progressing from my baby years to even an adolescent sissy. Mistress Katzenburg has deemed that I should start out the New Year as a brand new baby.

To start the year I am to put on my largest overstuffed diaper, put on my prettiest baby dress to celebrate my 0’th birthday, waddle and crawl around the house and then I will be put down for my baby’s nap. But, because I have been bad recently, when I take my nap I will have a special baby pacifier. The pacifier will be the biggest dildoe that Mistress Rosemarie has bought for me.

Happy New Year to all

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Pieclown: Happy New Year

Mistress Katzenburg has issued her first assignment for the new year to me. I am will be dressing up as the hung-over housewife, alone and in bed late into New Years Day.

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Pieclown: Halloween Assignment 2009

I received an email Tuesday October 27, 2009 from Mistress Amber Shummer. This is an exert from the email.

Since it is Halloween, it is time for some dress up with the following assignments.

pie clown – Something creative (anything but a clown)

Notes:

  • No masks are allowed
  • Costumes should be as creative, yet as uncomfortable as possible.

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sissy billy’s Independence Celebration in honor of Lady Liberty

Mistress Amber requested me to show respect of Independence Day by honoring and doing my best impression of Lady Liberty. In honor of Lady Liberty I dressed up for Lady Liberty by putting on my diaper, stuffing it as much as possible, putting on my big girls big bra and stuffing the cups with extra large water balloons, putting on my wrist and ankle cuffs to show proper obedience and respect for Lady Liberty and then to show humility (an also shrivel my private parts so I can better control them for Mistress Amber) I poured a quart of ice cold water down the front of my diaper.

I do this to show proper respect for Lady Liberty and our country. I stand and salute the Statue of Liberty which represents the freedom and liberty which we all enjoy in the United States of America.

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Pieclown’s salute to the Red, White, and Blue

Happy Independence Day to All.

Mistress Amber has given me an assignment to help celebrate our freedom. I was to get dressed up nicely, in tight fitting white clothing.

I was then to pop my left breast form to show it was filled with a red liquid, smash a white whipped cream pie in my face, and finally pop my right breast form to show it was filled with blue liquid. Before I did this I needed to be tightly packaged below the waist. This was to remind me that freedom IS NOT FREE.

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Independence Celebration

In the spirit of the upcoming 4th of July holiday, the following assignments are made:

Red, White and Blue
Pieclown is to get dressed up nicely, in tight fitting white clothing. She will then pop her left breast form to show it was filled with a red liquid. She will smash a white whipped cream pie in her face. She will pop her left breast form to should it was filled with blue liquid. As a reminder that freedom isn’t free, she will be tightly packaged below the waist. Her packaging will remain in place from the time her assignment is begins until the post of the results is finished.

Liberty in Diapers
sissy billy is to get dressed up in her most padded diaper, biggest breast forms and a full regalia of cuffs, then do her best impression of Lady Liberty. There will be a quart of ice water poured down the front of her diaper once it is put on. She will stay completely dressed until her post is finished.

Note: If she can’t manage to get it stuffed well enough, then I will recommend to Mistress Rosemarie that she get a spreading core diaper. Having padding 16 inches wide between her legs would be a good reminder of what a sissy baby she is.

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