Tag Archives: assignment

Sissy Summer – sissy billy’s disobedience – 2009-July-15

Sissy Summer is an assignment for all clients during the Summer Season.

I have been very good at honoring and managing the assignment until this weekend. Because I had failed in a previous assignment, I have to wear a ladies thong unlike the the other clients. This past weekend I made a trip to visit my in-laws with a lot of people around. I was very good in wearing my thong during the days, but failed in my assignment at night. For modesty and not to expose myself, I removed my thong and wore boys boxer shorts to sleep in at night. (Normally I do not sleep in anything – but had to in another person’s home)

I confessed this to Mistress Amber and she quickly reminded me that I could simply have kept my thong on and put boxer shorts over the top of them. Nothing gets by Mistress Amber and I should have thought of this, but did not for several subconscious reasons.

Sorry pieclown, you told me how to do this in your comment on going to the therapist and I did not remember.

Mistress Amber is getting to know me too well and she knows the real reason is not modesty. She has directed me to give the real reasons for not wearing a thong.

The truth is that I really dislike wearing a ladies thong and I have become so use to taking it off at night and being comfortable, that I did not try to find a solution and I took the easy way out.
Ladies Thongs are not for boys. They do not fit a boy and are extremely uncomfortable. They ride up my crack and I am constantly reminded that I am wearing one. They also are not meant for someone my size. The largest size I could find is an X-Large which is definitely too small. The more comfortable ones in X Large are very expensive and the reasonable cost thongs are very lacy and scratch and itch. The larger sized thongs for Plus Sissy’s are made of cotton and Mistress Amber has told me that a sissy has not earned the right to wear comfortable Cotton. Attached is a photo of my thongs and one can imagine how this sissy is uncomfortable.

![](http://cdpunishment.com/institute/images/2009/07/sissybilly_090714-001s.jpg)

Mistress Amber, I am not using this as an excuse. You told me to be honest and I have. I was so close to completing this assignment 100% for the weekend and only failed at night. I am sorry and hope the consequences are not to bad.

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.
![](http://cdpunishment.com/institute/images/2009/07/sissybilly_090704-008s.JPG)

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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][2]. 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][1]. Having padding 16 inches wide between her legs would be a good reminder of what a sissy baby she is.

[Pieclown]: http://institute.cdpunishment.com/profiles/pieclown
[1]: http://adult-baby-shop.de/product_info.php?cPath=1_16_32&products_id=467&osCsid=77cbb1c16b35f5
[2]: http://en.wikipedia.org/wiki/Statue_of_Liberty

Relief for sissy billy

I made a wish and Mistress Amber has granted it. I did not, however, ask what the price would be.

Now my wish has been granted and I must pay the price at the same time.

Mistress Amber has tagged this an assignment, I will tell you later if is a punishment. I seems like one. In hindsight I was to learn something and that is something private I will discuss with Mistress Amber.

sissy billy makeup Punishment for Mistress Rosemarie has been Posted and my basic feminine ensemble is based on Day 4.

I am to wear:

Wrist and Ankle cuffs, Clothespins on my nipples, High Heels, My sissy clitty-cage (May be removed when playing the Role of Kaya’s Master only), A lace up Corset, Panties, A Big Bra stuffed with the largest water Balloons, Diapered and wearing my Overstuffed Pink Plastic cover

Added conditions for this Relief

Higher High Heels, Bigger Water Balloons, More stuffing in my Diaper

Prior to the start of this Activity, I am to dump a 1 Quart pitcher of Cold Water in my Diaper. I realize now why Mistress Amber added this. My wish was to be very difficult for me to accomplish. My sissy-clitty shriveled up from the cold water.

The Cost of my Wish

I am to perform Kaya’s Video and I am to play both the Part of Kaya’s Master (My wish) and the part of Kaya (My payment for this wish)

![](http://cdpunishment.com/institute/images/2009/06/sissybilly_090625-002s.JPG)

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Relief for sissy billy

sissy billy has been very patient in her training, but has become a bit needy in the past few weeks. (I think this is why Mistress Rosemarie wanted her sissy to wear a clitty cage full time.)

> I have been laying in bed trying to go to sleep and I have an enormous erection. I laid on my back so as not to have an orgasm. It has subsided, but I have only milked my sissy clitty the one weekend of the wedding punishment and that was as directed by the punishment. Since the end of March I have only made love with my sissy clitty that one weekend. I have been so careful because you said that if I did have an orgasm and milk was to come out that the punishment was something that I did not ever want to know about.

> In that same email cautioning me not to milk my sissy clitty or else suffer a terrible punishment, you also suggested that I not wish for something that I might not like. I has been so long since my last orgasm, that I am willing to accept any consequences. Please Mistress Amber, I am wishing for you to give me your permission to milk my sissy clitty.

> I am afraid of the consequences, but I am desperate for making love to my sissy clitty.

So, as requested, I am giving sissy billy what she thinks she wants. She is to dress up as she did in day 4 of her yet to be published clothespin punishment with a couple of changes and re-iterations:

* High heels will be worn
* The pink diaper cover will be super-stuffed.
* One quart of ice cold water will be poured into the disposable diaper immediately after putting it on.
* The bra will be properly stuffed—the balloons used in the recent pictures were not sufficient.

Once dressed, she will play both part’s in [this video from Kaya][1]. She will pull out her sissy clitty and perform the part of Kaya’s master. She will then pull the diaper back up and perform the part of Kaya.

sissy billy will post the results of this punishment before she is allowed to take the clothespins off. The remainder of the clothing will remain in place for six hours following the posting of her punishment.

[1]: http://mastersclips.blogspot.com/2009/06/blog-post_12.html

Sissy Summer

All clients are instructed to wear panties or other female underwear for the summer. No male underwear will be allowed for any client during the summer season (starting June 21). Due to her failure to purchase appropriate thongs at the store during her last punishment, sissy billy will be wearing a thong for the duration.

sissy billy’s Standing Training Rules – sissy billy Confession 2009-May-25

sissy billy’s Standing Training Rules had only been issued last week, but already I am in trouble and must confess to Mistress Amber. I love a pretty negligee, but I can never sleep at night while wearing one and that should be easy for a sissy. This was true with my diaper training and now more so with the selected activity of having to wear wrist and ankle cuffs while in the house. I sleep in the house, so therefore I should wear them to bed as a reminder that I am the sissy in training and Mistress Amber is in Control. Mistress Amber has thoughtfully tried to help in my learning to sleep as a sissy by constantly assigning sleep time activities. Since last week I have worn the cuffs while in the house, but have had to remove them to sleep. Last night I laid in bed until 1:00 AM trying to learn to wear them and sleep, but could not. I took them off. Today was a Holiday, so it was not bad. I do need my sleep during the work week though. Per Mistress Amber’s assignment, I am to propose a punishment and then carry it out if I am naughty. The last time I tried to do this in my Modified Wedding Punishment it was a disaster for me as I thought I could accomplish a lot and impress Mistress Amber, but to no avail. Thankfully she took pity on me and made my punishment less severe. This time I think I will propose punishments more in line with my abilities to accomplish them, I Hope.

The only portion of the activity that I failed to obey was the cuffs and only at night. sissy billy would like to propose the following punishment scenarios.

In the case where sissy billy does not wear cuffs so she can sleep during the work week, this should be a lesser punishment as she does need to work and get some sleep and so is only a naughty sissy.

Since sissy billy needs her sleep, she can remove her cuffs before bed. However, to reinforce that she is still a sissy, on the nights she does not wear her cuffs, she will no longer be treated like a sissy, but like a sissy baby. Baby’s do not take showers in the morning, but sissy baby’s take baths and so sissy billy will take a bath and a sissy when taking a bath should always take a bubble bath. Tomorrow sissy billy will start taking bubble baths each morning she does not wear her cuffs. Additionally, since sissy billy is still trying to learn to wear her sissy clitty cage, she will be required to wear it whenever she is wearing her cuffs. sissy billy will owe four additional bubble bath mornings when this assignment is completed.

The second part is for a very naughty sissy. Since this activity may go on for quite some time, I will offer some options for myself so as to vary the punishment. The following punishments are also punishments that sissy billy has had in the past and does not like. So by offering a variety, she may learn how to deal with her punishments.

On non Work Week nights like last night when sissy billy did not need her sleep and did it for her convience, the following punishments will be carried out the next day before she goes to sleep. There are six punishments and only one will be awarded to her when she is a very naughty sissy. sissy billy will take a single dice, roll it and whatever number appears will perform that punishment. Listed below are the punishments listed 1 thru 6

1. sissy billy is to wear High Heels, a water balloon stuffed big bra, cuffs, sissy clitty cage, and a thong and stand in a corner for 10 minutes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
2. sissy billy will stuff a bar of wet Pink Camay soap into her mouth, put clothespins on her nipples, High Heels, cuffs, sissy clitty cage, and a thong and stand in front of the mirror for 5 minutes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
3. sissy billy is to make a bedtime snack of Level 1 and 2 baby cereal, vegetable, fruit and while wearing cuffs, sissy clitty cage, Stuffed bra and a thong eat the whole snack. After she has finish the baby snack she may take off her sissy items and climb into bed with a 4 oz bottle of baby formula and drink it. The sour taste of baby formula all night should remind her of being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
4. sissy billy is to put a bar of Pink Camay soap into water for 5 minutes so it is wet, soapy and gushy, get ready for bed by removing her sissy items and shove the Pink Camay into her mouth for 1 minute (enough time for the gooey soap to fill her mouth). She is then to take the bar of Pink Camay soap out, but is not allowed to spit any of the gooey soap in her mouth out, but must keep it in her mouth for another minute, get into bed and then she is to swallow it. The soap taste will remind her to think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
5. sissy billy is to put on High Heels, a water balloon stuffed big bra, cuffs, sissy clitty cage, and a stuffed diaper and rubber diaper cover, her teal Jumper to package it all and then using the treadmill in the basement walk for 1 mile waddling like Mistress Amber likes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
6. This is a Mistress Amber lucky – out of the goodness of her heart – get out of punishment card. There is no punishment, but sissy billy will kneel by the bed for 5 minutes before going to bed and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night. sissy billy gets to roll again and double the length of the punishment she gets on that roll. once completed, sissy billy will go to bed with all of her cuffs locked on anyway.

For last nights indiscretion sissy billy rolled the dice and the number two came up. I performed the punishment and will document it to Mistress Amber.

Of Course Mistress Amber has the option of modifying or changing any of the punishments above as well as deciding the length of this assignment. The next non work day is Saturday and so the very naughty sissy scenario will be decided after Friday night. Hopefully I do better this Friday Night.

**Updated by Mistress Amber on May 28, 2009**

Documenting the Rules 2

[Pieclown][], your assignment is to [finish documenting][3] the rules and regulations that I have taught you (or you have learned through trial and error). This should include all of the processes you currently follow, how to complete an assignment, how to make a website post, and so on. This is a research project. If there are original documents that you do not have access to (that you need), you must ask me for that document specifically. You are not being authorized to come up with new processes (though if you slip them in and I like them, I may keep them). Sensitive information, or information that pertains only to you should be shown as placeholders. Examples include user ids, passwords and prefixes.

You may have thought it was done before, but here is a less than the **minimum** list of what still needs to be completed:

* Finish formatting the headings in the table of contents style
* Explain tags used on posts
* Explain (or links to) tutorials on how to make a post.
* Add new rules, implemented since the last update.

I would add more, but I can’t remember right now what was supposed to be added. Maybe that’s why I wanted all of the rules documented in one place to begin with?

[Pieclown]: http://institute.cdpunishment.com/profiles/pieclown
[0]: http://institute.cdpunishment.com/tag/rules
[1]: http://institute.cdpunishment.com/about/rules_and_regulations
[2]: http://www.google.com/url?q=http://en.wikipedia.org/wiki/Fibonacci_number
[3]: http://institute.cdpunishment.com/2009/02/documenting_the_rules

pieclown: Dream or ? – Part 2

[Pieclown](http://institute.cdpunishment.com/profiles/pieclown) turned to look at the door. It was the desk clerk, the woman, who had hit him with a pie in the face. Julie stood there with a scared little smile. [Mistress Amber](http://institute.cdpunishment.com/profiles/amber_shummer) spoke “Pieclown, this is Julie, oh right you two have already met. Julie has been in contact with me. She is interested in becoming a mistress for
[The Institute](http://institute.cdpunishment.com/) I have been instructing for a short time. Today she will get some hands on training. Since she is not quite a mistress, you will refer to her as Miss Julie. Pieclown stand up and say hello.” Pieclown stood up, turned, and said “Hello, Miss Julie”. Miss Julie took a step in, but Mistress Amber held up her hand. “Pieclown are you going to welcome her in or should she leave?” asked Mistress Amber. Continue Reading

Documenting the Rules

Since the time [Pieclown][] joined The Institute I have been teaching her the rules—what to do an how to behave. This information is spread across a series of emails, [posts about rules][0] and probably half a dozen other places. And now she will be collecting it in a set of [Rules and Regulations][1].

[Pieclown][], your assignment is to document all of the rules and regulations that I have taught you (or you have learned through trial and error). This should include all of the processes you currently follow, how to complete an assignment, how to make a website post, and so on. This is a research project. If there are original documents that you do not have access to (that you need), you must ask me for that document specifically. You are not being authorized to come up with new processes (though if you slip them in and I like them, I may keep them). Sensitive information, or information that pertains only to you should be shown as placeholders. Examples include user ids, passwords and prefixes.

I will not by judging your work, rather the quality will be judged when the next client tries to follow your set of rules. (At the current time, I assume this will be Sissy Sarah, assuming she follows through with the rest of her application process by the end of the weekend.) **You will be punished for her mistakes** due to a lack of documentation. The punishments will likely be similar to treatments and will increase in severity for each incident according to the [Fibonacci sequence][2]. (That is 1 day, 1 day, 2 days, 3 days, 5 days and so on. If your rules are poor and allow her to make 5 mistakes, the 5th will be worth 5 days punishment, for a total of 12 days. If your rules are so horrendous as to allow 10 mistakes, the 10th will earn you 55 days for a total of 143 days of punishment. Almost 4 months of daily punishment. I can assume this is not what you want. If it gets to this point though, you should just assume that you will be wearing at least a bra and panties full time until 2010 **in addition** to your normal assignments and punishments.)

[Pieclown]: http://institute.cdpunishment.com/profiles/pieclown
[0]: http://institute.cdpunishment.com/tag/rules
[1]: http://institute.cdpunishment.com/about/rules_and_regulations
[2]: http://www.google.com/url?q=http://en.wikipedia.org/wiki/Fibonacci_number

pieclown: Dream or ?

Dream or ?

Pieclown could not believe he was doing this. The recent winner of the power ball was going to do something out of the ordinary. He was driving to meet his mistress. Not some 20 something hottie, but a woman that would put him through the ringer. Amber Shummer was this woman. Pieclown had met her a few years back, on the web site Institute of Crossdresser Punishment. She was in charge there and started requesting and then instructing pieclown as a member of the Institute. Winning the powerball, pieclown took care of the taxes, bills, savings, and tithing. He then contacted Mistress Amber about a possible meeting. She was open to the idea only on her terms. So here was pieclown driving across several states to meet with her.

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Sucks to Be Me

Back in August, after Mistress Amber [dressed me in a diaper][1], she further dressed me up in a couple of different outfits.

[1]: http://institute.cdpunishment.com/2008/08/why_i_love_working_with_stacee_skye

![](http://cdpunishment.com/institute/images/2009/01/btsp_080805-023s.jpg)

![](http://cdpunishment.com/institute/images/2009/01/btsp_080805-059s.jpg)

After each one, she sent me to the basement with a camera to “practice” Continue Reading

A Rules Based Culture

In looking at the recent client posts, I realize that I haven’t done a good job in making all of the rules that must be followed on the site all that clear. That will be rectified soon. In addition to the existing rules, I am adding a new one to help ensure that assignments and punishment are completed in a timely manner: “Treatments”.

There are now four types of objectives that may be given to a client:

* **Assignment** is the default type of objective given to a client in order to train them in our methods. It will usually involve dressing, bondage and humiliation.
* **Punishment** is a stronger form of an assignment, usually reserved for when clients break the rules or otherwise perform poorly. It will usually involve stricter (or longer) dressing, tighter bondage and greater humiliation.
* **Treatment** is a requirement that a client brings on herself for failure to promptly complete assignments and punishments. It will involve dressing full time.
* **Task** is similar to an assignment, but doesn’t involve training. It could be better described as administrative.

Treatments begin the same day that an assignment is made (or punishment given) and continue until completion. On the given day you must start wearing the prescribed daytime item under your normal clothes, and substitute your nighttime clothing for what is given. All clothing is additive, (Example: On day 10 you will be wearing what was already assigned for days 4 and 7, plus what is new for day 10.)

Day | Daytime Items | Nighttime Items
—|—- | —
4 | Panties | Nightgown
7 | Pantyhose |
10 | Bra | Bra, Breast Forms, Panties, Pantyhose
12 | Ankle Cuffs |
15 | Corset | Ankle Cuffs, Wrist Cuffs, Collar
18 | A good sized plug |
20 | Wrist Cuffs | Ankles locked together, wrists locked together
22 | Collar |
25 | Skirt (or slacks) | Blindfold, earplugs, hood
27 | Blouse |
30 | Breast Forms (XL) | A good size plug

When the results of the assignment are posted, there will be a section at the end for treatments required. You will post a thumbnail showing each treatment with a note stating “I chose this treatment by failing to finish in a timely manner.”

Note that the treatment schedule is subject to change and may be modified at the whim of any of The Ladies, or at the request of a client. Failure to keep track of the current rules does not exempt you from following them.

… and a Painful New Year

While I wish everyone a Merry Christmas, I hope that the holiday glow lasts in the cheeks of [Pieclown][] and [Stacee Skye][] though the month of January. This assignment is being given to both of them and is due to be completed by the end of January: you are to have someone paddle you like you in a skirt and high heels.

* The length of the punishment is up to the person doing the paddling.
* The implement used is up to the person doing the paddling. You are to offer all that you have at your disposal for them to pick from.
* Bondage during the paddling is up to the person performing it, though you are required to let them know it is highly encouraged.
* You must request that they take pictures.
* If asked if you have “had enough”, you must reply “No” or “Only if you think I have had enough”
* When the punishment is over, you must thank them in whatever manner they wish.
* You must make a post about your punishment.
* You must ask them how soon they would like to repeat the punishment. This entire scenario is to be repeated as many times as they would like by the end of January.

Let’s hope that they don’t want to repeat it everyday….

[Pieclown]: http://institute.cdpunishment.com/profiles/pieclown
[Stacee Skye]: http://institute.cdpunishment.com/profiles/stacee_skye

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