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.

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Oh My Goodness Mistress Amber. I don’t know what to do. When I made this mistake I had only started to research for my application and was very new to what was required. I do accept that the mistake was major. I have told you how humiliating this will be for me in front of the Doctor. This not what I expected. I have promised to complete my double diapered assignment before I go to sleep tonight and request that as I do this for the next two hours that I be given a change to think about it. I have such trouble with making decisions, but I will make a choice before I go to sleep and will respond tonight and start my lenghty punishment before I go to sleep as I am a sissy baby and will probably be a sissy and not humiliate myself in front of the Doctor. I will respond again in a few hours. sissy billy

@sissy billy: You don’t know what to do? You were told exactly what to do. You don’t have to show the doctor—you just have to push off (and increase) the punishment. No one ever said this was easy.

Yes Mistress Amber. I never assumed it would be easy. I expected to be trained and I knew it would be difficult. I have started my double diaper punishment at 11:30 PM. I am walking around the house with water ballons in my very big bra and they are heavy and bouncing. My 4 XL rubber panty is stuffed and I am wearing my 4 inch heels. The heels do help me waddle better. I would hope you would be proud of my sissy waddling. I just waddled back up stairs to my office and am standing in front of my desk leaning over. I will not sit down for the next two hours and will waddle like a sissy baby should. I am such a sissy and am still humiliated and embarassed by even wearing panties out in public even covered by my clothes, that I will probably take the sissy way out and take the extended punishment. I was just trying to talk myself up in courage to tell the doctor. We shall see how much of a sissy I am after two hours. I looked at the website for gags and restraints. Am I free to choose any gag or do you recommend one? Also – I showed you the restraints I previously bought without you permission. Are the restraints that I have unacceptable and if so which ones do you recommend. Thank You Mistress Amber for your guidance. sissy billy

Hello Mistress Amber. I lack the courage to expose myself to my doctor. I just would be so humiliated. I am such a sissy baby and you are right that I would pick the punishment in private. I will start the first part of the punishment as assigned tonight. will continue each night until complete and will send you pictures of what a sissy baby will endure instead of humiliating herself in front of her Doctor. sissy billy

@sissy billy: If you had actually read the post, you would know that you can choose any gag, as long as it has a cock shaped appendage that will be shoved into your mouth to keep you quiet. As for cuffs, you should get a matching set of ankle cuffs, wrist cuffs and collar that are “appropriately heavy duty” (as I wrote in the post). The cuffs I have seen on you so far don’t look like they could contain anybody. And they should be lockable.

I was not sure Mistress Amber and that is why I asked the question. I went back and read the post and I still was not sure. I have ordered the gag and cuffs and collar as instructed. sissy billy

I have shaved my body and I am now in Phase 2 of this punishment. This is an update of my progress for those of you that might find it amusing reading my humiliation and hopefully for sissies some would have some compassion for me regarding my punishment. I am wearing the prescribed sissy clitty cage, panties and pantyhose to work. The Sissy cage is difficult as I can not get it to fit right. If anybody knows any good sites to help with using this, please let me know. After the original humiliation of wearing these sissy items to work, work is good because I am allowed to use the bathroom. I run to the bathroom as soon as I get to work and it is the last thing I do before I leave. Diapering at home is another story. For those of you that have been punished like this I am sure you will agree that it is humiliating, icky and slimy, disgusting, and time consuming in the cleanup and a real “mess in the ass”. For those of you that have not experienced this lovely punishment. If you are smart, not like me, you will avoid this at all cost. I finally got my mouth gag on Friday and am using it each time I mess my diaper. Gagging for 10 minutes makes you regret that you were ever naughty. I also got my ankle and wrist restraints. I like to look pretty and wore my pink negligee to bed last night. I have never worn ankle or wrist restrains and they are confining and tough to go to sleep in. I finally went sleep and then the worst happened. With the diapering punishment, I am getting use to just letting go into my diaper. Well, I am loosing control, did not wake up and totally soaked my diaper, soiled my daiper and my pretty pink negligee was also soaked. After stuffing the gag in my mouth and laying in my bed for 30 minutes as prescribed I finally got up and changed into a new diaper. I did not put on a new negligee. Other then that, I am doing great if you believe me. The real fun starts at the end of my punishment. sissy billy

The poll has everyone liking my punishment for ” A very smooth move “. Whatever happened to the very good philosophy of take it easy on the new sissy on the block. I hope all of you who voted or liked the punishment will think twice the next time it happens to sissies like you. I am sorry if that is a mean thought. If it was me, I would vote that the new sissy gets a little leniency.

The new sissy should have it the hardest. The process of weeding out works well so that I’m not chasing after a couple dozen new sissies that aren’t dedicated.

Yes Mistress Amber. Your reasoning is absolutely appropriate for a new sissy like me and I hope I am progressing with your instructions, guidance and punishments in slowly moving towards becoming a better sissy in training as part of ‘ The Institute for Cross-Dressing Punishment “. My whining about other visitors to the site agreeing with your punishments is unfounded and inappropriate. I do not wish to put any of your tasks or punishments to a vote and will accept and not question the results of any of your polls regarding my training again.

This sounds like an awful punishment. I hope I don’t do anything to deserve a punishment like this.It sounds really humiliating.

A can of worms has been opened. All looking for a way to escape. Little do they realize, Fishing hook their fate.

[…] 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. […]

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