Author Archives: sissy billy

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 – Status and Report by sissy billy

I have been instructed by Mistress Amber as an additional followup assignment 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, status/explanation and a column for Mistress Amber to pass judgement.

Acti

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)

Continue Reading

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)

Continue Reading

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)

Continue Reading

Posts by Category

Copyright © 2025. Powered by WordPress & Romangie Theme.