Tag Archives: punishment

sissy billy’s Makeup Punishment for Mistress Rosemarie

Mistress Amber never forgets:

Out of the blue she noted that I had failed to complete and actually never started a punishment that Mistress Rosemarie assigned me for embarrassing her. My original punishment was for taking the sissy way out of accepting a punishment by saying that I could never wear clothespins on my nipples for more then 1/2 hour. I accepted the fact that I had ignored this punishment and accepted the punishment from Mistress Amber that I was now required to complete it. I accepted and started my punishment.

Day One:

Mistress Rosemarie intended for me to place clothespins on my nipples for just 1/2 hour on the first day. Since I was already wearing wrist and ankle cuffs per my Standing Training rules I put the cuffs on also. I also had lots of my panties to iron. I had not had clothespins attached to my nipples for several weeks now and I forgot how much they hurt. I did complete my half hour and felt good that I had done so. My nipples were already sore, but I knew the real punishment would be Day three and four.

There was one huge mistake I made. I did not tell Mistress Rosemarie that I was completing the assignment she had given me. She was so mad that I went and hid in my room. When I finally got up the courage to go back downstairs she had calmed down, I thought. All she said was that the conditions had changed and we would be starting again tomorrow. Then she sent me to my room to think about how much trouble I was in.

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sissy billy’s Standing Training Rules – Punishment Completed, I Hope – 2009-June-04

How I hope I have pleased Mistress Amber

On 5/18/09 Mistress Amber established Standing Training Rules for sissy billy. I was unable to obey these simple sissy training rules and was punished in various ways proposed by me as a training exercise and modified and approved by Mistress Amber. I have endured these punishments since that time as the sissy I am should. This past Saturday I was able to complete the non work week assignment and since Monday have also obeyed and followed the work week assignments.

Confession:

As a sissy I should not brag about completing a simple assignment which any sissy should accomplish easily. As a new sissy in training I have had great difficulty with this. I proudly write that I have nothing to confess and I have accomplished the non work week and work week assignments.

Punishment:

For a work week assignment not followed. 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:

Since Monday I have obeyed the assignments and therefore did not incur additional punishments. I did, however, owe three days of punishments for days that I did not follow the punishment assignment at the beginning of the training. Therefore, each morning before I went to work this week I did not take a shower. I filled the bath tub for a sissy bath and put lots of bubble bath in it so there were lots of bubbles. I then took a bubble bath like a sissy baby. When I was done I patted my self off with a fluffy towel like a sissy would do. I was also wearing my sissy clitty cage whenever I was in the house and I had my cuffs on. This was typical of what I have done each day to complete my assignment.

Of course this punishment is not complete unless Mistress Amber concurs and tells me that it is.

I hope she does since I really will sleep better without my sissy clitty cage on and I am so looking forward to a shower like a normal adult again.

I, of course, am still bound by the rules as originally stated in my Standing Training Rules and will wear cuffs when I am in the house (I am doing so as I write this post) and will abide by the dress rules.

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sissy billy’s Standing Training Rules – Back to being Punished – 2009-June-01

How I have disappointed Mistress Amber

Confession: Well I am sorry to say that after a single night of success, I am back where I started. It was Sunday Night and I had all intention of wearing my cuffs and sissy clitty cage, but after an hour of laying in bed and thinking too much about my obedience and servitude trying to please Mistress Amber two nights in a row, I broke down and took off my cuffs so that I could go to sleep. I again have a busy week at work, but that is no excuse to disobey Mistress Amber. A sissy should be able to follow and complete simple assignments and again I am not up to my punishment.

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 – 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.

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

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.

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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.

sissy billy attends a wedding

sissy billy wants to be able to suspend her punishment on the last day since she will be attending a friends wedding and she wants to avoid humiliation. (Of course, if she had just shaved earlier, then it wouldn’t have been a problem to begin with. ) So I had her come up with a suitable punishment so she would be able to take off her sissy diaper once she got up from bed on the 15th. The following is what she came up with (with my changes in italics and strike-through).

– ~ — • — ~ –

sissy billy is to return to her room immediately after the reception is over and milk her sissy clitty into her diaper. The she will put on a diaper, 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 milk her sissy clitty and then clean herself and put on a new diaper to wear to the brunch. She will remain in diapers for the remainder of the punishment. After the brunch, she is to return home and commence a full 24 hour punishment as payment for being allowed to go to the wedding. The punishment will be continuous for the 24 hour period with no sleeping allowed.

The following 24 hour schedule is general and will be modified by Mistress Amber with options of Mistress Amber’s choosing. sissy billy is to document in a diary the description of each punishment section, the start and completion time of each segment of the 24 hr agenda with pictures that Mistress Amber will dictate as being necessary.

12:00 to 2:00

Arrive home and change into attire as dictated by Mistress Amber. _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 pants to over flowing, put on her large bra, fill out the forms with water balloons (doing a bigger job than she has done in the past) and gag herself with her cock gag. She will clip her wrists together and clip her ankles together and then not be allowed to stand until this phase is over.

Write a letter of apology for requesting this modification, express gratitude that Mistress Amber allowed sissy billy this modification and write several times the agenda of the next 24 hr period laid out by Mistress Amber until sissy billy knows this agenda by heart.

2:00 to 6:00

Humiliation in public that sissy billy did not have to endure during the wedding with her friends. sissy billy is to go on a sissy girl shopping afternoon. She is put on her sissy clitty chastity, panties, pantyhose and a bra (unstuffed) and is allowed to put on whatever other clothes she feels necessary to conceal her sissy attire. She should spray a small amount of perfume on her like a girl would do just to remind her that she is a sissy even though her sissy clothing is hidden by boy’s clothes. She is then to drive to the next town and purchase feminine items as listed by Mistress Amber. (Items of Mistress Amber’s choosing such as lipstick, nail polish, make up, pantyhose, sissy clothes and whatever other embarrassing feminine needs that Mistress Amber can think of) She is to buy only one item in each store so that she is humiliated each time in each store. She is not to buy more then one product at a time.

6:00 to 8:00

Dinner – sissy billy is to eat and drink only what Mistress Amber has listed on the menu. sissy billy is to supply to Mistress Amber (If Mistress Amber approves this agenda and requests) by Sunday night (5/10) a list of healthy foods that sissy billy does not like and sissy billy will learn to like these foods in an attempt to make sissy billy get healthy and loose weight. Mistress Amber will add to this list things that she feels are good for sissy billy.

Mistress Amber will also prescribe fluids (Particularly Fluids that sissy billy does not like – since this is a punishment) continually through the night. At no time during this punishment is sissy billy allowed to use the bathroom.

sissy billy will be allowed to eat any Level 1 or Level 2 baby food, baby cereal, and baby formula. These are the only foods that will be permitted for the duration of the punishment, and fasting is not an option.

9:00 to 10:30

Exercise to wear off dinner. sissy billy is to go for a one hour walk wearing undergarments as directed by Mistress Amber. To assist with loosing this weight from Dinner, sissy billy is to give herself an retention enema of the type submitted by her and approved directed by Mistress Amber and then go for a walk. Should sissy billy mess herself, she is not to stop, but must complete her walking assignment.

10:30 to 11:00

sissy billy is to take a shower and clean up and is allowed to relax and rest for this time period. During her shower she will confirm that she is as hairless as when the punishment began, and adjust accordingly.

11:00PM to 3:00 AM

There should be a midnight snack as chosen by Mistress Amber

House Cleaning: sissy billy is to dress as directed by Mistress Amber (Maids outfit, dress, high heels, cuffs and collar, super stuffed 4XL diaper and properly filled large Bra, or whatever Mistress Amber chooses). She is to thoroughly clean the house from top to bottom without resting. 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.

3:00 to 3:30

sissy billy is allowed to rest for thirty minutes. This rest period should be in a manner that pleases Mistress Amber and does not have to be a true rest period for sissy billy. sissy billy is to go outside to get some fresh air, still dressed for cleaning. A few picture will be taken.

3:30 to 9:00

Miscellaneous punishments of Mistress Ambers choosing. Since sissy billy will not have finished the cleaning by now, she will continue doing that. If she thinks she has finished, then she can scrub the kitchen floor and the bathroom toilet and floor with a toothbrush.

9:00 to 10:00

General cleaning of whatever was messed in the house and sissy billy is to clean her self up.

10:00 to 12:00

sissy billy is to put on her Sunday best suit with whatever undergarments (lacy g-string, pantyhose, locked on ankle cuffs) Mistress Amber directs and attend a church service. During Church sissy billy is to think about her punishments and be grateful that she has a Mistress like Mistress Amber who is taking an interest in her training and resources of ‘The Institute for Cross-Dressing Punishment’ to assist her in this training.

Only If all of the above segments are completed and documented, will the punishment will be noted as complete. sissy billy is immediately return to her cleaning outfit above, then sit at the computer and send off documentation to Mistress Amber by correctly making a post with all applicable pictures on the website before she is allowed to rest for the rest of Sunday.

– ~ — • — ~ –

So, does this sounds like a fair trade? (Of course, even if sissy billy is getting the pointy end of the stick, it will still be considered fair since she made the proposal to begin with.)

I think sissy billy's punishment replacement is fair.

  • Yes (75%, 3 Votes)
  • No (25%, 1 Votes)

Total Voters: 4

A Very Smooth Move

Last night sissy billy admitted: “I deserve punishment for this basic mistake of not knowing the proper name. What is my suitable punishment?” The punishment is very simple and will handle an different whining complaint that she made: sissy billy is to shave herself tonight from the neck down—sissy babies shouldn’t be hairy at all.

If sissy billy wishes to put off this punishment, which I am pretty sure she does since she has an annual check up with the doctor next week, then two conditions will be added, First, each night until she decides to shave, she is to follow the directions in the following paragraph:

sissy billy is very sorry that she did not take the time to properly learn that the name of this institution of correction is known as ‘The Institute for Cross-Dressing Punishment’ and not the other name that sissy billy wanted to call it. sissy billy will endeavor to use the name of The Institute properly in all future communications; will be punished much more severely in the future for this type of infraction; and will recognize that her Mistresses are always right in attempts to correct her. sissy billy also realizes that she is dressed up as a double stuffed sissy baby (with a water-balloon over-filled large bra, a regular diaper, a grossly overstuffed pink plastic diaper cover filled with all manner of absorbent material, and punishment level high heels) and has a wetted down bar of pink Camay in her mouth of her own accord because she chooses to put off her punishment. By writing out this paragraph five times each night before going to bed, sissy billy is learning a very important lesson about ‘The Institute for Cross-Dressing Punishment’. sissy billy is learning that Mistress Heavynne Yeardleigh, Mistress Amber Shummer, and the other ladies of ‘The Institute for Cross-Dressing Punishment’, are committed to punishing and humiliating all of their sissy clients, especially when the sissy wants to delay a punishment. sissy billy is also learning that when being trained by Mistress Heavynne Yeardleigh, Mistress Amber Shummer, and the other ladies of ‘The Institute for Cross-Dressing Punishment’, the punishment will only get worse the longer it is delayed.

Secondly, after she shaves, she will multiply the the day of the month (of May) that she decided to shave, and spend that many days following with the following punishment rules:

  • She is to wear her clitty cage, panties and pantyhose to work.
  • The only toilet she may use is the one at her job.
  • She is to be diapered as soon as she arrives home from work, and remain so until she leaves for work again. Both cloth and disposable are fine, but the plastic cover must be worn over them.
  • If she loads her diaper, she is allowed to change herself after gagging on a cock for 10 minutes. (Every sissy should be required to practice this way.)
  • If she just wets her diaper, she is allowed to change it after 30 minutes.
  • Pantyhose may be worn to help her compress the diaper if she needs to leave her house.
  • And since she needs to pretty and likes to wear a negligee to bed, that will be allowed if she is wearing some appropriately heavy duty cuffs on her wrists and ankles—just so she doesn’t forget this is a punishment.

So if she waits until the 7th to shave, she will spend 14 days, from the 8th through the 21st under these rules. Or, she may surprise me and just shave tonight. Stranger things have happened.

Taking Our Name in Vain

In the middle of one of the first email exchanges that I had with sissy billy, I had to gently correct her on the name of this institution:

Our name is not “The Institute for Cross-Dressers Punishment”. The proper name is printed at the top of EVERY SINGLE WEB PAGE!

And of course, she couldn’t help but reply:

You must think me an idiot Mistress Amber.

Well, she should have helped, because that was the wrong thing to say. So, I gave her what I thought was a suitable punishment:

Your punishment is as follows:

  • You are to wet down a bar of pink Camay
  • You are to dress in a negligee, different than your previous punishment.
  • You are to put 10 clothespins on your body (at least 2 on your nipples as before)
  • You are to shove the wet bar of pink Camay in your mouth
  • You are to write out (longhand) the following sentence 50 times:
    “sissy billy is very sorry that she did not take the time to properly learn that the name of this institution of correction is known as ‘The Institute for Cross-Dressing Punishment’ and not the other name that sissy billy wanted to call it. sissy billy will endeavor to use the name of The Institute properly in all future communications; will be punished much more severely in the future for this type of infraction; and will recognize that her Mistresses are always right in attempts to correct her.”
  • If a mistake is made in the sentence, it should be lined out AND the total due is increased by 2.
  • If the soap leaves the mouth for any reason, it is to be soaked in water, replaced in five minutes AND the total due increased by 10.
  • Sentences shall be written in ink on lined paper.
  • The line before each sentence shall be a status line containing
    • Date
    • Time
    • Number of this sentence
    • Total number of sentences to complete

Then she really started the whining:

I don’t think I could get it done all at once. It will take me hours.

(Apparently her day is much shorter than mine.) I was even nice enough to offer her some relief in having to finish her punishment (which she declined to take) and her performance was miserable:

As I can tell you finished two sentences (plus two incomplete) and had twenty added for dropping the soap. My count shows you adding 24 sentences to the 50, completing 2 for a total of 72 remaining. That is a spectacular failure.

You should realize that the standing rule has been that a failed assignment is given again until it is repeat correctly. In addition, a punishment is added for the first failure.

I will let you know when I come up with a suitable punishment for this miserable failure.

And though it has taken a long while, I finally have a punishment suitable just for her.

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