Assignment 7: The Penance

Do you know why I have decided to be merciful, slave?

…because I should have obeyed my instincts.

When you told me that you were a good girl, it didn’t feel right. I dismissed the feeling as a consequence of my cruelty and cynicism. Now, however, I realize it was a consequence of my intuition.

My intuition was this: that in reality, you’re a very naughty little girl.

Go on… say it… and you’ll feel how right it feels. Say it now!

“I’m a very naughty little girl…”

And now say the natural adjunct to that sentence…

“And I need to be punished.”

However, slave, although the words feel right, they’re not correct. Because what you need is more than just punishment, you need something a little bit stronger…

It’s called ‘penance.’


The Oxford dictionary defines penance as…

“A punishment inflicted on the guilty as an outward expression of repentance for wrongdoing.”

The key concept here, sissy, is “outward expression.”

Being publicly humiliated and shamed is a key part of paying for one’s sins, and that’s why sissy must do penance as well as punishment. The sentence of chastity was entirely private, and therefore lacked the ignominy and contempt that public punishment induces. That’s why you’re still a naughty girl.

Even though you’ll be in chastity for a year, only your Mistress and her clients will know about it.


There is an even more important reason, however, that wrongdoers are publicly punished: deterrent. It is necessary to remind other deviants considering the same crime, that we as a society are watching and waiting to castigate them. What kind of deterrent is chastity for any other transvestites or sissies thinking of acting upon their perversion?

The simple fact is, therefore, that the permanent decrepitude of sissy’s sex organ was not sufficient deterrence, and that’s why you sinned against your Mistress and engaged in unauthorised milkings.

To conclude… You need penance.


Unfortunately, we don’t live in a Game of Thrones universe so you won’t be able to do a public walk of shame, sissy (my preferred penance.)

Instead, I’ve thought of a realistic penance you can actually do. And as realistic is the key word, I will give you a choice so that you can do a penance that fits your circumstances.


Sissy will clean its house from top to bottom dressed in an appropriate attire: a starched maids uniform. That’s right! Sissy will scrub and polish and fold and wash – dressed in the uniform of a female domestic servant. (if it is not possible economically for you to buy such a uniform then you must propose an alternative to your Mistress.)

No satin, no frills!

Sissy will provide documentary evidence that the regulation uniform has been purchased and documentary evidence of the sparkling bathroom, kitchen and other rooms that have cleaned. And just in case you don’t know what type of uniform I’m talking about – see below.

Duration of punishment: indefinite (the sissy must do one initial spring clean; however, the sissy will receive follow up punishments at various times throughout the year.

N.B. when sissy is cleaning in its maid’s uniform, there must be a chance it is caught or spotted. And thus… shamed!


You dressed her in sexy outfits, but you really wanted to wear them yourself, didn’t you… you deceitful little sissy!

Okay, so you already confessed your sordid shenanigans to your Mistress, but now you must confess to a current or ex-girlfriend.

The heart of your confession will not be your soiling of her lingerie drawer, however, or your insatiable thirst for cum and cocks, but the crime of PRETENDING TO BE A MAN.

This confession is based on the AA ritual of contacting people from your past and your present and apologizing for your errant behavior caused by alcoholism. In this case, the cause will be your transvestic fetishism and compulsive abuse of sissy pornography. And your confession will go something likle this.

Dear _____________ I’d like to speak to you about a course of therapy that I’m undertaking.

This therapy has led me to a point where I must be honest with myself and anyone who has been a victim of my dishonesty. This dishonesty caused me to pretend to you and others that I was a man…when deep down I already knew that I was a sissy who could never satisfy a woman. Although I knew in my heart of hearts that you needed a real man, I selfishly kept you entangled in my deceit, thus preventing you from finding the true satisfaction of a true, red blooded male.

While you were sincerely investing in our relationship I was undermining it, and while you engaged in the sensible adult part of a romantic union, I spent my time like all sissies endlessly looking at online porn and coveting your satin lingerie. I know I can never take back that time I robbed, but I would like to offer you my labor as compensation. Once a week, I will come and work as a uniformed maid for you and your new boyfriend and will do whatever you to tell me to. And just in case you think I will derive any satisfaction from servility, I shall be wearing a chastity device.

(You can vary it according to setting and personality, but you get the drift, don’t you, sissy!)


The cuckold confession is basically the same as penance 2 but the emphasis is on…

  1. Her need for sexual satisfaction.
  2. Your acknowledgement that you can’t provide it.
  3. You begging her to cuckold you so that your guilt can be alleviated and the penance done.
Finally, she’ll get the big cock she craves and the man-sized load that comes with it.


We already agreed that a Game of Thrones style public shaming was not viable, but there’s nothing to stop us from throwing you into the online world to be ridiculed, scorned and humiliated (exactly what you deserve.)

And let’s face it, there’s a certain poetic justice in using the place where you feed your repugnant sissy appetite for porn (the internet) into the place where you are finally exposed as an inveterate transvestite.

In that vain, you must dress like a street hooker and take a photo of yourself where you belong (in the street like a tranny whore). Below is the type of photo you must take.

Suck it up!

You must then share the photo with three contacts. Five minutes later, you must send them a message saying that you sent it by accident and that the photo is related to a fancy dress party.

They can’t be sissy contacts!

They must be contacts that you will be super embarrassed to have divulged your sissy nature to. Yes, you have made an excuse that it’s for a fancy dress party, but they will all know that you’re a sissy and you’re begging for cock and cum.

NOTE (Do not engage in any of these penances that could affect your reputation or your standing in the community WITHOUT GAINING MY APPROVAL FIRST!)



Let’s face it… You’re a lot better looking than Shelley, so if she can find a man to punish her… So can you. Use your sissy initiative to find the sternest older man you can find… dress like a tart..and tell him that you’re a naughty girl who needs a spanking.


5b. Before you go to bed tonight, you will put on your nightdress and then take a belt from your wardrobe, and you will fold it in two.
You will then adopt the punishment position on your bed and lift up your nightdress. You will then deliver ten cracks of the belt to your naughty bottom (no more no less). You will do this by swinging behind (not the best method but that’s all we have at the moment). While administering the punishment, you will repeatedly ask for your Mistress’s forgiveness for being a naughty little girl.
Please confirm the punishment has been administered.



One of my principal preoccupations about this program is that new girls end up cherry picking their gender: i.e. they take all the superficial things they like about being a girl, but never engaging in the difficult stuff.

Show me that you are willing to learn about women’s rights both in a contemporary and historical context… and I will definitely pardon your errant behavior.

You can either read/listen to Mary Beard’s short work…

Or…watch this video.

To complete the penance, you must tell me by email the most interesting thing you learned.

Watch the Full Series