Monthly Archives: June, 2009

Relief for sissy billy

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

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

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

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

I am to wear:

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

Added conditions for this Relief

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

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

The Cost of my Wish

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

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

Continue Reading

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.

![](http://cdpunishment.com/institute/images/2009/06/sissybilly_090616-003s.JPG)

Continue Reading

Relief for sissy billy

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

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

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

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

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

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

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

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

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

Sissy Summer

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

sissy billy’s Standing Training Rules – 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.

Continue Reading

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.

Continue Reading

Posts by Category

Copyright © 2026. Powered by WordPress & Romangie Theme.