sissy billy’s Upcoming Punishment

I have been instructed by Mistress Amber to tell you about sissy billy’s upcoming punishment by My Superior, Mistress Myckie Jo Katzenurg, but I am getting ahead of myself. I must first tell you about my day today and my restart of training in becoming a sissy.

The past several weeks I have not had an assignment (except Sissy Summer) or punishments. Although undeserved, even Sissies need a little time to rest and I thank Mistress Amber for this. However, Sissies are Sissies because they do need constant supervision and punishment for simply Cross-Dressing. I admit that I certainly do.

I was not surprised and did expect any day that Mistress Amber’s kindness must come to an abrupt end. I arrived home today to find a note from Mistress Rosemarie that I better read my email immediately and on my desk at the computer was an enema and a diaper. My stomach immediately started to hurt.


Mistress Amber had made an assignment/punishment for me to immediately perform. I responded in an email to Mistress Amber that I would obey completely. Several weeks ago I had been rude to My Superior, Mistress Myckie Jo Katzenburg and to Mistress Amber. Such rudeness must be cured, but I was surprised that Mistress Amber stated that my punishment would be from the person that I had been rude to. I was upset, but it is fair and I must be held accountable for the consequences of my rudeness.

I was instructed to go to the store and purchase several items for my impending punishment, but there were conditions assigned to this shopping trip.

I was to administer to myself the two Fleet Enemas that had been left for me. I was then to put on a bra, a g-string pantie, pantyhose and cuffs. I was also allowed to wear a diaper if I wanted to. Thank Goodness I did wear a diaper.


I have in the past been given enemas by Mistress Rosemarie and even taken to the store shopping, but never for more then 15 or 20 minutes. Today was to be something I had never experienced.

I gave myself two enemas which was not so bad, but then started to dress as required. A pink g-string pantie, diaper, bra, pantyhose and then cuffs. This took me longer then expected and I then put on work clothes and a sport coat to hide the cuffs. By the time I was dressed it had already taken 15 minutes and my stomach was already starting to hurt. I already wished I could go the toilet. I am still afraid of meeting someone I know and being exposed and I started to drive to the next town to shop, which was almost 15 minutes away. I was already starting to get stomach cramps and squeezed my butt cheeks to hold it in.

I entered the store to shop and tried to hurry as I was ready to explode, but I had to walk slowly to control the enema. I had been given a list of items to buy by Mistress Amber. A large carton of oatmeal, bars of pink camay soap, a box of granola cereal and gallon size plastic bags. I did not question what I was buying, just that I had to pay and get home. The line was long and I could hardly control myself in the line. I had such cramps by then that I could have cried like a little girl.

Finally I got to the car and no sooner had sat in the seat that I had to relax a bit so the cramps would ease and I leaked into my diaper. I had such terrible cramps by then. I had held the enema now for almost 45 minutes and wanted so badly to be home on the toilet. The drive home (another 15 minutes) was unbearable. The cramps would get terrible and I would have to stop holding it in and the result was a poop in my diaper. This happened several times on the ride home as the cramping continued.

I pulled into my garage and with a half full diaper rushed to the toilet. Finally some relief, but it took another 20 minutes before the cramping stopped. It was horrible and disgusting.

The second part of my assignment was to acknowledge my inevitable punishment to be administered by My Superior, Mistress Myckie Jo Katzenburg and to guess how each of the purchases I made might be used in my punishment.


I once again apoligize to My Superior, Mistress Myckie Jo Katzenburg for being so rude and accept that I should be punished by her for this insult to her.

Having read many stories about her, I can guess how each may be used.

She likes big breasted sluts, so I would guess that the Oatmeal will be mixed and put into gallon bags and used to stuff my big sissy bra. My Superior, Mistress Myckie Jo Katzenburg is also partial to diapering, so I would guess that the granola cereal, being crunchy and scratchy will be stuff in my diaper to cause me further discomfit. The pink camay will then be used to wash my mouth out and teach me how mean it is to say horrible things about another person.

I am truly sorry. Please be kind and do not punish me too severely My Superior, Mistress Myckie Jo Katzenburg.

Sincerely, sissy billy


Got Something To Say:

Your email address will not be published. Required fields are marked *


Yes, as was to be expected, the time for punishment is once again upon us, it should really have been no surprise after the way you dissed Ms Myckie-jo that she would have been allowed to conduct your punishment. You were very brave going shopping with the double enema in, at least they were small fleet ones, I only have access to a large red bag for my own enemas. I think your ideas for what all the items you bought are very insightful; I especially think the gallon bag to be filled with oatmeal for breast forms is probably correct. I think you are doing so well sissy billy, and should be applauded for your obedience in this case.

Honestly, I’m not sure how you lasted that long with the double enemas–they may be small yes, but they’re chemical laxatives. I’ve never been able to hold one more that 15-20 minutes just sitting still trying to control it, let alone more than an hour of driving and walking. This really was quite an impressive feat.

I know those pink Camay mouth soapings are not nice to have done to you, but I’m glad to now I am not the only one who gets them. I will be interested in following the outcome of this.

Hello Sweetsuds,

It sounds like you also are familiar with the pink “Camay”.

That is Mistress Rosemarie’s soap of choice for herself and also for my many mouth washings as I often seem to be naughty.

Not pleasant. It usually reminds me to be good for at least a few days.

sissy billy

Copyright © 2017. Powered by WordPress & Romangie Theme.