Halloween Dress-Up – sissy billy Version

Mistress Amber is celebrating a Holiday likes she loves to do by making Sissies Dress-up for her amusement. I must admit that this is much more desirable then being punished as Cross-Dressing Sissies normally are. Mistress Amber has a very good memory or very good records or probably both. She remembered one of my very first submissions expressing my interest in Ballerinas (It was a picture actually). I do love ballerinas and the Tutu’s/Ballerina Outfits they wear. I always fantasized of wearing a Ballerina’s Tutu for Halloween, but never had the nerve to. So my assignment for Halloween is to dress as a top heavy Ballerina.

I was looking forward to dressing up as a Ballerina until Mistress Rosemarie reminded me to look at the “fine print” of the assignment. In my excitement to dress up I had not read the additional condition of my dress-up also being uncomfortable.

All of you should know, Mistress Rosemarie loves Halloween and always dresses up and usually drags me to a Halloween Party. I always refuse to dress up which aggravates her to no end, but she does make me go to the Parties. She was in her glory that I was going to be forced to be dressed up this year. I was terrified that she would make me go to a party dressed as a Ballerina. I was so thankful when she said that this year we would stay home. Mistress Rosemarie really is a nice Mistress and while she likes to humiliate me at home, she does know what a panic I was in to be exposed in public.

Early in the week she started to plan my Ballerina Costume. She picked out a white Tutu that could also fill in as a spare Crinoline under my Maid’s Outfit. Then she started to pick my accessories to fulfill the “Uncomfortable as possible” portion of the assignment. I naturally had my big Ladies’ Big Bra and over-sized stuffing already in my closet. Then she decided I should start to experiment with my “Spreading Core Diaper”. Add to that my corset laced tightly like a Victorian Lady, Stockings and my Punishment Level 5″ Pink High Heels. My Costume hung on the bathroom door for days so that I could anticipate my assignment.

This Halloween would be Exciting and Humiliating and Terrifying. (I was threatened with having to hand out treats to all who came to our house.)

It is Saturday Night and Halloween is here. I dressed up and I did complete my assignment. Thanks to Mistress Rosemarie, the humiliation was all mine. The fun is in the “detail” and not the assignment. This was a Halloween I should not soon forget.

All my life I have fantasized about being forced to Dress as a Ballerina.

I have always dreamed of being a Ballerina. I picture myself looking like this, but I do know better. How humiliating it would be to dress in a Tutu and parade around the neighborhood, knocking on doors and saying “Trick or Treat” or worse yet, accompanying Mistress Rosemarie to a Party. My first thought, when Mistress Amber made this assignment and Mistress Rosemarie read it was of this humiliating exposure. Mistress Rosemarie just smiled at me and let me think for a few days that we were going to the yearly Halloween Party one of her friends have. I trembled for days knowing that she would delight in forcing me to go to the party.

Finally I was given relief and told that we would stay home. I was so relieved and thanked Mistress Rosemarie again and again, but then the assembling of my costume began and the humiliation (an excitement) of dressing as a Ballerina started again. I both looked forward to it and dreaded it.


Mistress Rosemarie said that a tightly laced Corset to make my Body more feminine (which is impossible) and a very large Big Ladies Big Bra filled to capacity with very large water Balloons for balance was an absolute necessity. Frankly, I do not know how I can “prance” through the house unable to breathe and/or not topple over.

Next came the spreading core Diaper that Mistress Rosemarie had ordered for me several weeks ago. I still have not figured out how to properly use it yet, but she smiled and just said that practice makes perfect. On the inside of my rubbery pink diaper is a zipper filled with absorbent material and into it, guess what, I had to pour two quarts of very cold ice water. Not only was it very very cold, but very very bulky and very very heavy.


To finish off my Ballerina uncomfortable undergarments, I added Stockings and my Punishment level 5″ Pink High Heels. My balance was definitely in jeopardy. I walked around the house in this state per Mistress Rosemarie’s direction to practice my balance. As Mistress Rosemarie dressed up in her Witches Outfit (What else?) which is one of her favorites, she kept coming up with chores for me to do. It was go down stairs and make me tea, go into the guest room and get my black high heel shoes, go clean the downstairs bathroom in case some friends stop by (this comment really worried me) and many many more. I was slowly getting my balance, but already my feet hurt.


Finally Mistress Rosemarie is finished dressing and now it my turn to become the Ballerina of my Dreams. Of Course my dreams did not include wearing an overstuffed big big bra or being laced in a corset until I could not breathe or wearing a pink rubber filled diaper or wearing very very high Pink High Heels. Oh well, I was finally dressed in my Ballerina Outfit and thought I looked really cute. I couldn’t understand why Mistress Rosemarie laughed hysterically, but I guess I did look kind of like a big sissy in a ballerina outfit. I practised curtsying for several minutes for her. Very difficult being top heavy and in high heels.


I then practised prancing through the house trying to look ballerina like with very little success. Mistress Rosemarie then explained to me that since she was not going to make me go out “trick or treating” or go to her friends party that the least I could do was answer the door when “trick or treaters” knocked on the door and help her hand out candy. I was horrified at the thought that I would have to answer the door. I begged her not to make me do this.



I cried and begged and out of annoyance she finally relented and gave me a choice. Help hand out treats for 15 minutes or stand in the corner for an hour. As much as my feet hurt and my legs ached, I chose the wall. Mistress Rosemarie was furious and I knew it would cost me further humiliation at some point in time. After 10 minutes of standing against the wall my body was really aching and I went to Mistress Rosemarie and said I was sorry. She then told me that I would not have to stand at the door, but would have to stay in costume for the rest of the night, which I did.

Mistress Rosemarie was wondering if you think sissy billy has become the ballerina of her dreams.



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Hello sissy billy, I think I like the ballerina NOT in a diaper. I hope you had fun with you assignment and fantasy.

    Hello pieclown. We have not talked in a while. Hope all is well. I think I like the ballerina not in the Diaper also. Certainly would not ask her to leave. I think I am in trouble though for putting a picture not of me in the posting. I won’t being doing that again. Oh well. I did have fun with my assignment and also my fantasy even with the added conditions of very uncomfortable accessories.

Hi silly billy, Yes it has been some time since we talked. My computer crashed in Aug. and now I am spending most of my computer time looking for a job. Hey but that is life. Things can always get worse. I hope you also enjoy you new freedom.

Hello pieclown, I am sorry to hear that you are looking for a new job. Times are tough, but I am glad to see that your attitude seems upbeat. Positive thinking always shows through and I am sure it will in your job search. I have not yet enjoyed my new freedom (with restrictions), but I am looking forward to it. I am planning to make it good since I have been good for quite some time now. I am busy thinking of a new great fantasy.

Best of luck in finding something. sissy billy

sissy billy,
i just had to write to let you know how much i loved your ballerina outfit. You looked so cute so i voted for you in the “halloween Contest” as posted by Mistress Amber. Why haven’t the other “sissy’s” voted in Mistress’s poll?

Sissy Billy, I think you looked lovely too. But why not open the door for trick or treaters. The Mistresses know we crave as much humiliation as we can get and you know, deep down, that its both what you want and what you deserve. Hugs

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