Tag Archives: humiliation

How I spent my summer vacation – Episode 1

I have been instructed by Mistress Rosemarie to share some of the fun and games and activities that I did over the summer. This is once again a lesson that I must endure by sharing my experiences and humiliations because I am shy. I should have learned by now that I can not hide my humiliations and if I had shared just one with pieclown I may not be having to post several. Mistress Rosemarie has set a quota of 1 or 2 posts a week of my many humiliating days I spent on my summer vacation. This is to go on until Mistress Rosemarie has felt that I am over my current phase of sissy shyness. Of course I am sure that Mistress Katzenburg may also have some things to say.

One day a package arrived in the mail and Mistress Rosemarie was very excited. It was a present she had ordered for me for my birthday in the fall. She smiled as I opened it and giggled as I turned red with embarrassment. It was a little girls fancy frilly party dress. She took my hand and led me to the bedroom and proceeded in telling me how to dress. I put on a stuffed bra, a crinoline and this very frilly baby blue little girls party dress. No one, not even a girlie girl would ever wear this. For a sissy to expose herself like this is beyond humiliating. I also put on red thigh high stockings, a very big stuffed plastic diaper because I was still a little baby and of course cuffs so that I would behave. I stood in the bedroom totally humiliated as she took pictures for my scrapbook.

[![](http://cdpunishment.com/institute/images/2010/10/sissybilly_100820-001e.jpg)](http://cdpunishment.com/institute/images/2010/10/sissybilly_100820-001s.jpg)

My humiliation was only the beginning of our Mistress – sissy evening

Continue Reading

sissy billy – a Sorority Bitch

A short while ago we were all given an assignment. Because the Institute had become quite dusty, we were to present ourselves as a sissy maid prepared to clean. A Poll was established to vote on who had presented themselves as the most humiliated sissy maid.

The losers were to be trained further and experience further humiliation as “Sorority Bitches”.

From the Start my performance was inadequate and had 0 Votes until a late surge left me with 2 Votes, but still in last place. I guess I was the most in need of humiliation and training by the Sorority and now I was to be a “Sorority Bitch”.

The assignment was basically that you were to experience a Sorority initiation Training Exercise in obedience and humiliation. There would be four Training Sessions over the course of the Evening divided into a Pleasant Dinner at a reception hall followed by a punishment session for insolent Sorority Bitches. You were then to be taken back to the Sorority House for some additional Training Punishments. Then, finally, it was Bedtime and a pleasant Sleep. The actual training episodes were not so pleasant.

It was for each of us to determine our training activities. We were required to pick at least one activity in each session, a minimum of 7 total activities and the Judges were to decided which Sorority Bitch would graduate and which would need further training.

I intended to try as hard as I could to impress the Judges and would attempt as many activities as I thought I could accomplish. To start, I strove to make myself as pretty as I could and be the Best Sorority Girl I could. I was to attend a Dinner at a reception hall and the dress code was a Corset, stockings, high heels and a dress. Since it seemed like a formal affair, I chose an old, but very pretty Fancy Dress that I once imagined wearing to a Prom.

I stood ready to be a Sorority Bitch.

![](http://cdpunishment.com/institute/images/2010/06/sissybilly_100613-001s.jpg)

Continue Reading

A Trip with my Mistress

I made a big mistake at the end of last year. A sissy does not have any rights and only has the obligation to please her Mistresses. She is a sissy and should be kind and sharing with all and therefore has an obligation to other sissies also. She should be honest. But most of all she has an obligation to perform her sissy duties without prodding or insistence from her Mistresses.

Simply, she should Volunteer.

I did not and therefore I am where I am now. I am sorry Mistresses and other sissies. The correct thing to do would have been to show everyone how excited I was over my presents from Mistress Rosemarie and to share this excitement and tell everyone what I got. I was too embarrassed to do this and now I have to physically wear and show everyone my new things.

It is our Anniversary and Mistress Rosemarie decided that we should take a nice trip and that my main purpose was to pleasure her enormously. I was also to bring my presents because she intended to make good use of them. I packed my Suitcase including my very pretty negligee I received from her for Christmas, several other negligees so that I would look pretty for her each night and of course the new two quart enema system, new pink soap, condoms, a Bridal Magazine and of course panties, bra and pantyhose that I would wear full time for the weekend. She examined my suitcase, found it complete and off we went.

[![](http://cdpunishment.com/institute/images/2010/01/sissybilly_10-01-22-009t.jpg)](http://cdpunishment.com/institute/images/2010/01/sissybilly_10-01-22-009s.jpg)

Packed and the suitcases loaded in the car we drove off on Day 1 of our trip. Mistress Rosemarie drove as she is a much better driver then a sissy could ever be. She began to explain what would happen on our trip and I began to blush and worry already. She decided that my humiliation should start now and she had me put on a pretty women’s kerchief and tie a bow at my chin. When we passed cars I was to look directly at them. We were away from home and little chance of exposure, but it was humiliating and Mistress Rosemarie even slowed up sometimes so they could get a good look. It was humiliating. This was just the start.

Continue Reading

A sissy must be prompt in her assignments – Morning 3

It is Sunday Morning and I have been very busy, but still have not completed my profile. So I am once again completely dressed in the sissy girlie outfit of Mistress Rosemarie’s choosing.

I have rephrased and corrected sections of my profile and added another section. I was certainly hoping to have completed this by now, but I have one question that I must ask Mistress Amber because I am not sure how to do a link. After several months of trying to be a good sissy client you would think that I would know all of these things by now, but I do not. I quess I am still in need of more and extensive training and punishment as a sissy client.

I will, hopefully, finish my profile as soon as Mistress Amber helps me with my question.

Continue Reading

A sissy must be prompt in her assignments – Night Two

It is Thursday night and I am back fully dressed as a pretty sissy. This is definitely not pleasant being dressed as a sissy all evening. Not only I am making dinner for Mistress Rosemarie, but she is making me go to the Ladies Room often during the evening to fix myself – you know – fix my makeup and lipstick and fluff and straighten my skirt and blouse. It certainly is difficult being a girl and looking you best.

I have found and collected training photos and have uploaded them to my profile page. I hope to complete some miscellaneous items of my profile on Saturday and can finally go back to my normal dressing life. I hope

Continue Reading

A sissy must be prompt in her assignments

I was recently, well actually a month ago, assigned a task by Mistress Amber to fill out a profile set up by her and to complete it as soon as possible. Well, I got busy with other assignments and finally pushed Mistress Amber’s patience to the limit. A sissy never has the excuse of being to busy to fulfill her Mistress’s instructions.

Mistress Amber was still very understanding, which I do appreciate greatly, and did not punish as severely as I deserved. I have been directed by her to dress up completely in feminine clothing every night until I completed this task. I further disappointed Mistress Amber by not starting my task immediately last night and now I am also to wear my sissy clitty cage.

Mistress Rosemarie is delighted with this because she had warned me to get going on my assignment and she so likes me to look pretty. She now forces me to dress as soon as I get home and to stay dressed all night. I make and feed her dinner, clean up and then go to the computer. Mistress Rosemarie tells me to take my time now because she wants me to dress like this every night, but I know I must complete and please Mistress Amber by finishing my Profile.

Mistress Rosemarie laid out a pretty feminine outfit and took pictures for all to see and delighting in my humiliation.

![](http://cdpunishment.com/institute/images/2009/12/sissybilly_091214-003s.JPG)

Continue Reading

Junior Summer – 2 – Training Starts and The Surprises Keep Coming

“Oh My Heavens” sissy billy uttered. She was frozen in the middle of the floor and looked terrified. She obviously was afraid to move. She finally took a step forward and with hesitation she opened the front door.

There stood Mistress Rosemarie. sissy billy let out a sigh of relief for she had hoped Mistress Rosemarie would be her first trainer. Her hope was short lived. She told Mistress Rosemarie she would be right back as soon as she put on her clothes, but as she turned Mistress Rosemarie shouted stop. She grabbed sissy billy’s hand and dragged her outside still dressed in her peignoir set, cuffs and punishment high heels. She stopped on the front lawn and in the middle of the day there were lots of neighbors outside. The humiliation was intense for sissy billy and she turned red. Mistress Rosemarie then dragged her the rest of the way to the car like a little girl and sissy billy jumped in the front seat. Mistress Rosemarie made her get out and get in the back seat. She then said very loudly so all the neighbors could hear: “Sissies are like little girls and they should sit in the back seat. She then made a big deal of buckling sissy billy in with a seat belt and I am sure sissy billy could hear all the neighbors laugh and start talking. They then drove off.

Continue Reading

The Actual Wedding Punishment

I have completed my letter of apology to Mistress Amber and it was sent with sincerity and with respect for my Mistress. I am now onto my next punishment phase and the one I fear the most. I am to go out on a girl’s shopping trip to several stores and girls do every Saturday. I have left on my diaper which is still unsoiled and taken the oversized stuffing out of my humongous bra as is allowed so I can hopefully keep some dignity. I have covered myself to the extent that I do not believe that anyone will notice that I have a diaper and bra underneath my clothes. I have several items to purchase and I am driving to a mall several towns and many miles away so that I do not have a change of knowing anyone. I have taken a beach bag in lieu of a women’s Pocketbook/Purse as allowed by Mistress Amber as a further good gesture by Mistress Amber allowing me not to expose myself. I thank you Mistress Amber, but know I owe a big favor for this courtesy. In the bag I am carrying my penis mouth plug and two diapers as directed. I arrived at the mall, parked and walked into the mall with my bag. I immediately felt selfconcious and after several women looked strangely at me, I went into a Borders bookstore and purchased a book and got a borders bag to carry it in. It concealed my bag. I know this was probably my paronia and probably was cheating, but nothing was presribed that I could not buy anything else.
I could not believe how many people where in the mall. Mostly women shopping as women do on Saturday’s. I thought I would try to do the most difficult first. I was to go into a lingerie store and buy a thong. The first one I came to was a Victoria’s Secret. I had shopped their for my wife several years ago, but at Christmas and as a Christmas present with lots of other men around. I entered the store and their were no men, just a lot of women. I walked back out and walked down the way a bit. I finally tried to get up nerve and went back in. I know the other women probably did not even notice me, but I thought everyone was looking. I did find my way to the pantie racks and was looking for the largest size I could find. A young sales lady came up to me and asked if she could help. I must have turned red, but could not ask for help. I said I was OK and she turned around and as soon as she did I left.
I am sorry Mistress Amber, but I could not do this. The thought of taking a ladies thong and standing in line with all the other women and paying for a women’s thong was too humiliating. I know you will say the reason I could not do it is because I did not want to. I just could not do it with all the other women around.
I went further down the mall and tried to do it again in a women’s store and not a lingerie store hoping it would be easier and the same thing happened. I have bought frilly feminine clothing and lingerie on line and recently purchased two thongs, a red and black one on line per your direction, but I could not do it at the store.
My next stop was to buy women’s makeup at a general store and I did buy cosmetic base, eye liner and lip gloss. I already had lipstick and other cosmetics.
My next stop was a drug store (a Rite Aide) and purchased more diapers. I asked the lady at the register if I could use the bathroom, but she said no, that they did not have a bathroom for public use. I did not ask or push to use the employee one and I just left the store.
From my account of this assignment, it is obvious that I have failed. I am sorry Mistress Amber, but the humiliation of doing this was just too much for me. I am sure you will have something to say about my failure and I will accept the consequences for not overcoming my humiliation.
Attached are photos of my attempt to go on a girls shopping trip.

sissy billy sissy clothes for a girl's shopping trip

sissy billy sissy clothes for a girl's shopping trip

sissy billy trying to hide her diaper and bra

sissy billy trying to hide her diaper and bra

Avoiding Humiliation

sissy billy [commented that][1]

> I lack the courage to expose myself to my doctor. I just would be so humiliated. I am such a sissy baby and you are right that I would pick the punishment in private. I will send you pictures of what a sissy baby will endure instead of humiliating herself in front of her Doctor.

So she is working though her punishment prior to actually shaving. In addition to this, she has a few other events coming up that she will be attending as a diapered sissy *after* she’s shaved:

* Two days of playing golf (May 9 and 10)
* One time at church (May 9)
* One nice dinner with her Mom (May 10)
* One wedding (May 15)

I just wonder what these people would think if they knew there was a sissy baby among them.

[1]: http://institute.cdpunishment.com/2009/05/a_very_smooth_move#comment-2407

Posts by Category

Copyright © 2025. Powered by WordPress & Romangie Theme.