Tag Archives: sissy-billy

sissy billy’s Standing Training Rules – A SUCCESS – 2009-May-31

A Success:

Mistress Amber has been so kind to allow me to tell you about the first small success I have had in my first two months of trying to become a worthy sissy of the “The Institute for Cross-Dressing Punishment”. This is only a small one night completion of a punishment, but I am very proud of it. I want to thank Mistress Amber in my training in becoming an obedient sissy.

Saturday Night – 2009-May-30:

It is Saturday night and I am home for the evening. I have put on my ankle and wrist cuffs and my sissy clitty cage. I have also put on my new pretty Lilac Peignoir. I have included pictures so you can see. Isn’t it really pretty and feminine. I just love it. As instructed by Mistress Amber when I dress in my sissy clothes at home I am to wear my big bra and I have made bigger water balloons that please Mistress Amber stuffed in my bra.

I have decided that tonight I am not going to just give in and accept a punishment and hope for the best. I am going to succeed tonight, not only in wearing my cuffs as the assignment dictates, but also in wearing my pretty peignoir all night. I am not going to take them off even if I lay awake all night long.

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sissy billy’s Standing Training Rules – Punishment – 2009-May-30

How I have disappointed Mistress Amber

Confession:
On Friday Night, which was a non work week night, I tried to sleep with my cuffs on, but failed to keep cuffs on my wrists and ankles for the entire night. I was very tired and thought that I would be able to go to sleep, but at 1:00 AM after laying in bed for two hours I was still wide awake. I then gave in to my sissy weak willpower and decided to take off my cuffs.

Punishment:
I rolled the dice and the number 3 came up. Therefore the punishment is as follows: Punishment # 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.

Completed Punishment:
I got out of bed, kept my sissy clitty cage on and put on a red thong, kept my cuffs on, put on and stuffed with water balloons a big bra and then I went down stairs to the kitchen to make my sissy baby snack. I used only Level 1 and 2 baby food and made baby cereal, added baby vegetables (squash and carrots), added fruit (Plum and peaches) and then poured baby formula into a baby bottle. I added too much baby formula to the baby cereal and it was really soupy and looked even worst then the last time I had to eat baby food. I also made more then the snack portion required by mistake, but once I had made it I knew I would have to eat what I made. I then went back up to my bed and sat on the edge of the bed to start eating my snack. Finally when I finished the food, I took off my sissy items, took my sissy baby bottle and lay down in bed to drink it and go to sleep. I took appropriate photo’s to document my punishment for all to see. I still had problems going to sleep because the sissy baby food snack was sitting in my already stuffed stomach from dinner. I could still taste the icky baby food and since I was not allowed to wash my mouth out our brush my teeth, the baby formula taste coated my tongue and mouth. As I lay in bed trying to go to sleep with the awful taste of pasty and icky sour tasting baby formula in my mouth, I thought about why I am such a sissy and can not successfully complete the assignments that Mistress Amber gives me. I will try to be a better sissy in the future. I should be thankful that Mistress Amber is helping me to become a better sissy and I will try to please Mistress Amber more each day with my training.

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sissy billy’s Standing Training Rules – Punishment – 2009-May/June – Typical for each Day

How I have disappointed Mistress Amber

Confession:
On Typical Work Week nights I can not sleep with the cuffs on and when I am ready to go to sleep, I remove my cuffs.

Punishment:
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. Each Day sissy billy will take a bubble bath each morning she does not wear her cuffs the night before. 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.

Completed Punishment:
Each morning before I go to work I do not take a shower. I fill the bath tub for a sissy bath and put lots of bubble bath in it so there is lots of bubbles. I then take a bubble like a sissy baby. When I am done I pat my self off with a fluffy towel like a sissy would do. I am also wearing my sissy clitty cage whenever I am in the house and I have my cuffs on. This is typical of what I have done each day when I have not worn my cuffs to sleep and that has been every night during this work week.

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

How I have disappointed Mistress Amber

Confession:
On Sunday Night, which was a non work week night, I failed to keep cuffs on my wrists and ankles when I was in the house.

Punishment:
I rolled the dice and the number 2 came up. Therefore the punishment is as follows:
Punishment # 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.

Completed Punishment:
I put my sissy clitty cage on with a red thong, kept my cuffs on, put high heels on, placed a clothespin on each nipple and then shoved a fully wet Pink bar of Camay soap into my mouth. I took appropriate photo’s to document my punishment for all to see and then faced the mirror for 5 minutes as timed on the kitchen timer. While I stood facing the mirror for a full 5 minutes I recited to myself a part of one my punishments previously given to me by Mistress Amber. Mistress Amber and the other Mistresses and Ladies of ‘The Institute for Cross-Dressing Punishment’ are always right in their attempts to correct a sissy like me. I should be thankful that Mistress Amber is helping me to become a better sissy and I should learn by my mistakes and correct them.
![](http://cdpunishment.com/institute/images/2009/05/sissybilly_090525-001ws1-e1278051782249.jpg)

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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**

sissy billy’s Standing Training Rules

Since I have some other work that will take priority in the near future, I gave sissy billy a new activity list in the middle of last week

* While at home you are you wear your ankle and wrist cuffs.
* You may dress as much as you wish outside your house.
* You may dress at home as much as you wish, but the large bra (fully stuffed) must be included.
* If you think your actions will disappoint me you are to put a post on the site
+ Your confession
+ The assigned punishment (which you feel is appropriate)
+ the competed punishment

This allows her to dress as much or little as she would like, but still be reminded that she is learning who is in control.

The Actual Wedding Punishment – Status and Report Card by sissy billy

I have been instructed by Mistress Amber as an additional followup for The Actual Wedding Punishment to post a status and report card of how I performed my punishment. I was instructed to review the actual punishment and list all activities that were required of me and to list the status of completion and in cases that I did not complete a portion of the assignment to explain myself to Mistress Amber. I have included a Table below listing activity and status/explanation for Mistress Amber to pass judgement.

Activity / Task Requirement|sissy billy – status – Remarks
————————–|—————————-
After the Wedding|
Shave if necessary to pre-punishment Condition|I did clean up my sissy clitty, but did not shave the rest of my body and ask for relief from this exposure to other
Milk her sissy clitty into a new diaper with penis plug in mouth,put on a Rubber diaper cover, attach collar/wrist/Ankle cuffs and go to bed and not get up for an reason until morning|Done
Brunch|
Clean herself|Done
Milk her sissy clitty into a new diaper with penis plug in Mouth|Done
General Requirements|
Each time she has to change her diaper, insert penis plug into mouth and milk her sissy clitty in a new diaper and then put it on|Done
For each meal she is to eat only Level 1 & 2 baby food and may only drink baby formula. Fasting is not permitted|My first meal was dinner on Saturday and I ate the whole plate and drank the formula. I almost threw up and baby food does not taste good. After this point I did not fast, but ate minimal portions and watered down the formula
Letter of Apology|
Return home and talk off all clothing, but diaper on, put on 4XL rubber diaper cover stuffed to overflowing, put on Big Bra stuffed to overflowing with water filled balloon, put on Jumper to package it all and put on collar, ankle and wrist cuffs and lock together|Done
Insert penis mouth gag until letter of apology is complete|Done – I kept the penis plug in mouth until the letter was complete
She is not allowed to stand until this punishment is over|I crawled to my desk to write the letter
Write a Draft Letter of Apology for requesting a Modification of punishment and express gratitude for Mistress Amber’s kindness for being allowed to do so|Done
Rewrite Letter in neat handwriting|Done
Girls Shopping Trip|
Change Diaper, put on rubber diaper cover, pantyhose and keep large size bra on without water balloons|Done|
Remove Wrist cuffs & collar, leave on ankle cuffs|Done
Put on outer clothing of choice|Done
Carry a Pocketbook/Purse with diapers for changing and penis mouth plug|I requested and received permission to carry a ladies beach bag instead of a Purse. I did buy a book as soon as I arrived at the mall and carried another shopping bag so this did not look so evident
Go to a lingerie Store and buy a thong|I could not do this. I was too embarrassed and left the store without buying a thong. No excuse except my own humiliation
Go to a Women’s Store and buy a thong|I could not do this either and left the store. No excuse except my own humiliation
Purchase Makeup for herself|I purchased makeup I did not already have – beige base, eye liner and lip gloss
Go to a drug store and purchase diapers and then after paying, request to use their restroom and change her diaper|I purchased diapers, but the sales lady said they did not have a toilet for public use and I left without arguing with her
Saturday Night|
Return home and take off everything but diaper, put on Rubber 4XL diaper cover and stuff to overflowing, keep Big Bra on and stuff with huge water balloons, put on Jumper to package everything, put on collar, ankle and wrist cuffs and lock together|Done
She is not allowed to stand until this punishment session is over|Done – I crawled around like a baby all night
She is to fix a dinner of baby food and formula|Done – but ate a minimal portion
She is to stay like this until morning|Done – but I could not sleep with the large breasts and lay awake on my back most of the night
Sissy maid cleaning the house|
She is to fix a breakfast of baby food and formula|Done – but ate a minimal portion
sissy billy is to change diaper if necessary, put on her 4XL rubber diaper cover and stuff as much as she can|Done
She is to put on her sissy maid’s outfit with high heels|Done – High Heels were difficult to work in, but I kept them on the entire time. My feet can attest for that – they hurt
She is to put on her wrist and ankle cuffs and her collar|I forgot to do this which is evident in the pictures
sissy billy is to apply makeup suitable for an unretouched photo to attach to the post|I did. I did not retouch the photos. I am sorry one is somewhat blurry and unclear and the other one I was applying my lipstick and the mirror got in the way of my pretty face
She is to make a list of everything she cleaned|I forgot to make the list, but did send the pictures of what I cleaned to Mistress Amber
She is to clean the house and take pictures to send to Mistress Amber to decide if her house cleaning was adequate or would have to be done again the next weekend|The house was cleaned and the pictures have been forwarded via email titled house cleaning for Mistress Amber’s inspection. The house was very clean
Sunday Night|
Remove sissy maid outfit, leave diaper on, leave Rubber 4XL overstuffed Cover on, leave Big Bra overstuffed with water balloons on, put back on jumper to package and lock wrist and ankle cuffs together and collar|Done
She is not allowed to stand until punishment session is over|Done-I crawled
She is to fix a dinner of baby food and formula|Done – minimal portion
sissy billy is to stay like this until Monday morning when she has to go to work|I worked on the posts – slowly because of the locked wrist cuffs. At about 9:00 PM I could not continue – I was very tired and knowing that I would not be able to sleep during the night I stopped. I had a very busy week at work and I needed to be alert on Monday and request consideration for not completing this session
Posting of Status|
sissy billy is to report status of each event and post each individually with appropriate pictures|Done
All posts should be made before she goes to work on Monday|Done-posted before I went to sleep on Sunday Night

The Actual Wedding Punishment – Sunday Night

It is Sunday Night and I have taken off my Sissy Maid Outfit.

Mistress Amber – I am sorry, but I must give up. I can not do this. I am so tired that I can not continue. I am sending this as a confession and an admission that I have failed to complete this assignment. I will send the rest of the photos tomorrow.

I apologize to all the other sissies as being a poor example of what a good sissy should be.

When I was young my mother would tell me that my eyes were always bigger then my stomach and I would always order more then I could eat.

Well, that is just what I did when I submitted this punishment to Mistress Amber as something I could accomplish. Mistress Amber even made it less severe and I still could not accomplish it. I am a poor excuse of what a good sissy should be.

I apologize Mistress Amber

sissy billy

The Actual Wedding Punishment – Sissy Maid Service

It is Sunday Morning and I am so tired. I hardly slept last night bundled like a sissy baby with ankle and wrist cuffs locked and humongous breasts keeping me from rolling over. I was so glad to get out of my sissy baby wear and into a sissy maid outfit. I am having a tough time doing this. I bought this sissy maid outfit a number of years ago and I am humiliated every time I put it on and now I am glad to have it on instead of sissy baby clothes. I changed my diaper and had trouble milking my sissy clitty again. This is so humiliating that I can not do it several times in one weekend. Maybe I am becoming a sissy.
I have put on my overstuffed diaper, have voluminous breasts in my big bra, a white sissy maid crinoline, my pink frilly maid outfit, red high shoes and have applied my feminine makeup. I am blushing looking in the mirror at how pretty I am.
I have lots to clean and it will take several hours. I will get back to you.

![](http://cdpunishment.com/institute/images/2009/05/sissybilly_090517-015s.jpg)

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The Actual Wedding Punishment – Saturday Night

I am home from my humiliating trip to the mall. It was a disaster as related in the previous post. It is now Saturday night and I am tired and humiliated and know I am already failing my overall assignment. I will continue in an effort to improve.
I am back in my diaper and my collar, ankle/wrist locks and I am nothing more then a sissy baby. I did have to change my diaper before getting back into my sissy baby wear. The good part of milking my sissy clitty is getting harder. I am not as young as I use to be and it took a long time to milk into my diaper. This is embarrassing as every other thing I have to do.
I am crawling around like a little baby. I am trying to start my posts, but am making little progress.
I have put the baby food low enough so that I could reach it and I have made myself a sissy baby meal. I am hungry, but this does not look good. Let me just say, that I now know why a baby spits out its baby food when you feed it to her. It tastes horrible and even though I was really hungry and did manage to shove it all down my throat, I could have thrown up several times. If I was allowed to fast, I would not be eating. The baby formula was also terrible. I did manage to water it down so I could at least get it down my throat.
I am so tired that I will be going to bed early, although I do not imagine that I will sleep well or much.
Good Night Mistress Amber, I will see you in the morning.

![](http://cdpunishment.com/institute/images/2009/05/sissybilly_090516-009s.jpg)

![](http://cdpunishment.com/institute/images/2009/05/sissybilly_090516-010s.jpg)

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

The Actual Wedding Punishment – Letter of Apology

I finally got home (It was a long drive and my hangover still had not got any better – even with anacin) and started my next punishment. I am to write a letter of apology to Mistress Amber for being a naughty sissy unable to follow simple instructions and for causing her a lot of extra work. I went to my bedroom and took off all of my clothes and first had to change my diaper. I had managed to wet it on the drive home. With the penis plug in my mouth, I performed one of the pleasant duties of this punishment and milked my sissy clitty into a new diaper. I then put on my 4XL rubber diaper cover, a big bra stuffed with ballons on the verge of exploding just like Mistress Amber has said she so likes in many of the comments made to this site and my new teal jumper to package it all together. I then put on my collar, ankle and wrist cuffs locked together and with a penis plug in my mouth crawled to my desk to write my letter to Mistress Amber. I was not allowed to stand, but with the ankle and wrist cuffs locked together, all I could do was crawl like a sissy baby should. I climbed into my desk chair and began to write my apology.
This was not a quick letter as I was to first compose a draft and then rewrite it in good handwriting so everyone could read it. It was also very difficult, because with my wrists locked together, I had to constantly pick both up and re-position them on the paper so I could write neatly.
Mistress Amber does think of little things to add to each punishment. The penis gag in my mouth was gagging me and I almost threw up several times with my upset stomach. I wanted to write fast, but had to slow down so the letter could be readable. Below is me locked and gagged in my sissy baby diapering and also attached is my letter to Mistress Amber which I sincerely mean. I hope she can forgive me for all the additional work and effort I have caused her. If only I could be a better sissy.

![](http://cdpunishment.com/institute/images/2009/05/sissybilly_090516-004s.jpg)

![](http://cdpunishment.com/institute/images/2009/05/sissybilly_090516-006s.jpg)

The Actual Wedding Punishment – Brunch

I have been to my friends Wedding and it was very nice. The reception was held in a big hotel in the city and I got a room in the hotel, so needless to say, I did drink way to much and I am know paying the price. I returned to my room after the wedding to start my punishments and must confess that I failed at my first assignment and the one I had been looking forward to for 6 weeks of chastity. I was unable to milk my sissy clitty into my diaper. I was so depressed, but I will blame it on having to much alcohol and nothing else. There are to be many diaper changing opportunities through the weekend. I put my diaper and rubber cover on, prepared the bed and attached all of the cuffs and collar and fell into bed. I was tired and fell asleep quickly and did not awake until 8:30 when I felt my wet and messy diaper.
The morning proved more successful for changing my diaper (I did remember to stuff my plug into my mouth) and milking my sissy clitty into a new diaper, it did work this time even with a huge hangover. The sticky new diaper did remind me through the morning of my punishment. There was a nice full service restaurant in the lobby and I went off to brunch with my friends and managed to eat some breakfast which did make me feel better. Conversation was good with the girls talking about the wedding and the dresses and how good everyone looked. The guys talked about playing golf in the afternoon, which I had already made an excuse for not going. This was an additional punishment (no golf) that was not assigned, but still obeyed because I would be busy performing my punishments. I was jealous of them, but only half listening to them as I listened in on the girls conversations. Most times I would rather listen to the girl’s conversations rather then the normal things the guys argue about.
Well I did get through the first event. However, I did realize that this would be the easiest event of the weekend.
![](http://cdpunishment.com/institute/images/2009/05/sissybilly_090516-001s1.jpg)

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the actual wedding punishment

even though the majority of people thought [sissy billy’s punishment suggestion][1] was fair, I have decided to change it up a bit–just to keep her on her toes (and to lessen some of the rigidity she had imposed).

[1]: http://institute.cdpunishment.com/2009/05/sissy_billy_attends_a_wedding

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sissy billy is to return to her room immediately after the reception is over ensure that she is as smooth as the first day of her punishment. She is to milk her sissy clitty into a new diaper before putting it on. The she will put on a rubber diaper cover and attach ankle and wrist cuffs and a collar, all locked on, to reinforce the severity of the punishment. She is to bring the rubber cover with her to the hotel room to protect the bed because she will not be able to leave the bed until morning no matter how much she soils herself.

She will get up in the morning and clean herself and milk her sissy clitty into her new diaper she will be wearing to the brunch. She will remain in diapers for the remainder of the punishment. For the entire weekend, in order to be able to change her diaper, she is first to put the penis gag in and then milk her sissy clitty into her new diaper. Once she has made a new mess, she will be allowed to changed into this new diaper. After brunch, and until she arrives at work Monday morning, she will only be allowed to eat Level 1 or Level 2 baby food, baby cereal, and baby formula. Fasting is **not** an option.

After brunch, sissy billy will head directly home. sissy billy will strip off everything but her diaper, lock on the wrist cuffs, ankle cuffs and collar. Then she will stuff her 4XL diaper panties to over flowing, put on her large bra, fill out the bra with water balloons (doing a bigger job than she has done in the past), gag herself with her cock gag and put on her plastic jumper . She will clip her wrists together and clip her ankles together and then not be allowed to stand until this phase is over. sissy billy will then write a letter of apology for requesting this modification and express gratitude that Mistress Amber allowed sissy billy this modification. Once finished, she will recopy it for better penmanship.

Once the letter is finished, sissy billy will have the humiliation in public she did not have to endure during the wedding with her friends. sissy billy is to go on a sissy girl shopping afternoon. She will we wearing her ankle cuffs (locked on) with her diaper and a bra. She will carry a purse containing extra diapers and her gag so she can change herself. sissy billy will make at least four stops:

* At a lingerie store, she will buy at least one thong for herself.
* At a women clothing store (not a department store), she will buy at least one thong for herself.
* She will buy some make-up for herself.
* At a drug store, she will buy an adult diaper for herself. Immediately after paying for the diapers, sissy billy is to ask the cashier if she can use the restroom. She will then go to the restroom and change her diaper.

She may then return home, where she is to strip off her outer clothes, return her wrist cuffs and collar, stuff her 4XL diaper panties to over flowing, fill out the bra with water balloons and put on her plastic jumper . She will clip her wrists together and clip her ankles together and then not be allowed to stand.

Sunday morning, sissy billy is to dress as a sissy baby maid (Maids outfit, dress, high heels, cuffs and collar, super stuffed 4XL diaper and properly filled large Bra. Then she is to experiment with her makeup to get a look that is appropriate for un-retouched pictures on the site. Once she is satisfied, she is to thoroughly clean the house from top to bottom. She is to make a list of everything that she cleaned, take pictures and Mistress Amber will decide whether she cleaned thoroughly enough or will have to repeat this cleaning next week. Once sissy billy is finished with her maid outfit, she is to return to the jumper outfit she was wearing the previous evening and leave it on until rising Monday morning.

sissy billy is to send off documentation to Mistress Amber by correctly making a post for each event she had (brunch, apology, shopping, sat night, maid cleaning, sun night) with all applicable pictures on the website before she is goes to work on Monday.

An Alternate Diaper Cover for doing housework

Does your Mistress make you perform Maid’s Duty with a Diaper on? Do you have to keep it on even when it is soiled? Do you have trouble keeping it on as you work hard at your sissy chores? With Mistress Amber’s Approval you may want to order a Jumper in lieu of a diaper cover. It is easier to keep in place because it is a [jumper](http://www.fetware.com/jumper.htm) and has over the shoulder straps. Duct tape is so messy and ruins the diaper cover unless you are careful. There is also a cute accessory for sissy babies to go with the jumper. A must have sissy baby [pacifier](http://www.fetware.com/Adult_Diaper_Pins.htm) to plug in your sissy mouth while you work and to keep a sissy from complaining. Of Course, if you have been a particular naughty sissy, Mistress Amber may want you to struggle with keeping your diaper up as an additional punishment and reminder or she may want you to so overstuff your diaper that this will not fit. If you have been a good sissy and have pleased Mistress Amber you may want to ask her permission to use this while performing your sissy chores.

![Alternate Image Text](http://cdpunishment.com/institute/images/2009/05/sissybilly_090512-001s.jpg)

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