Do You Need to Be a Chastised Sissy? Sissy Training Evaluation and Rules

Are You a Naughty Sissy?

There are SOME sissies that are truly sweet and demure. They are far and few in-between but they do exist.  Most sissies are naughty little tramps no matter the clothes they wear.  You might try fooling others but you will never fool me!  Under those silky sissy panties is a tiny little stupid stick that controls you. The moment it gets hard and drippy (which seems to be all the time!) you lose your mind! But even when its rock hard you have the reality that you’ll never ever please a woman with that tiny little nub.  This is why you are a sissy. You accept your “shortcomings” and move into the realm of sissified adore pansy. If you are ever going to be a speck of dust in HER FEMDOM WORLD then you have to work very hard to get and keep her attention.  This is often difficult when you can’t keep your hands out of your panties!  Therefore we need to take the situation at hand and evaluate the best training course for YOU.

Naughty Sissy Test

Answer yes or no to the following questions. If you would like to elaborate in the comment section below you may:

  1. Do you squirt more then 3 times a week?
  2. Do you wear silky girl’s panties more then 3 times a week?
  3. Do you fantasize about sucking male cock?
  4. Has your whore hole, sissy pussy, been penetrated by any object or cock?
  5. Do you find yourself unable to focus on work or other important life task because you are obsessed with dressing in women’s clothes?
  6. Do you find yourself unable to focus on work or other important life task because your want to touch your little clitty?
  7. Has it been longer then 30 days since you’ve had sex with a woman?
  8. Do you find yourself online searching personal ads, Craig list for men?
  9. Do you find straight vanilla sex as a man boring and unfulfilling?
  10. Are you addicted to wanking your tiny little she-she?


If you answer yes to more then half or the questions above then you are a naughty little sissy tramp.  The best course for you is to immediately enlisted in strict sissy training which may include chastisement. This could be honorary or with a chasity device.

The Naughty Chastised Sissy Training Course

The very first thing you must do is get your filthy little paws off that clitty! From now on you will not touch without permission. If you go potty then you must learn to sit down. If you have to clean it then you must get a warm bowl of water or cup and do so without any type of arousal. You are not permitted to stroke without permission.  You must earn every little touch, stroke and cummies from now on.  If you have a wet dream or cheat in any way you must report this infraction to me immediately!  You will save the link to this post and report in the comment section. If you find that you are unable to stay honest and that you’re just a cheating sissy tramp then you must request to be placed in a device and monitored carefully.

Sissy Rules of Chastisement

  1. All touching must be approved by Sissy Training Goddess Josephine.
  2. All orgasms must be approved by Sissy Trainer Goddess Josephine
  3. Sissies are required to wear panties 24/7 unless other arrangements are made
  4. Chastised sissies must sit down to go potty.
  5. All authorized squirting must be properly cleaned up. These instructions are outlined when given permission to squirt.
  6. Chastised sissies must confess all naughty thoughts  that made the owned clitty twitch, jump or get drippy.  Once a week the sissy will post in comments below or private email Sissy Trainer Goddess Josephine a full and detailed confession of all naughty thoughts or any violations committed by the naughty little bitch.


Required Tools

  1. A large long handled wooden spoon or proper spanking paddle
  2. A punishment chair. This can be any chair or stool.
  3. At least 6 pairs of full bottom ultra feminine panties. They must not be plain and all panties must be approved.
  4. A box of super tampons
  5. A large silky pink ribbon or bow to tie around the clitty and sissy plums when instructed.

*Other items might be chosen on a case by case basis. 


Sissy Training Requirements

If you want assignments to earn the privilege of touching it its best you call me to establish a relationship. You can take your chances by posting below in the comments section, however I prefer phone or text session via 

If calling if a problem or your not available during my call hours you can purchase my Humiliated Sissy Boot Camp  You do not have to do the very intense humiliating sex assignments unless you are ready. The purpose is to establish communication, reporting and begin email training. I am also happy to work with another Enchantrix Mistress if you prefer to speak with someone during the times I am not not available. Together we can closely monitor your program.

Any questions????? Post them below or email me




9 comments to Do You Need to Be a Chastised Sissy? Sissy Training Evaluation and Rules

  • Alex

    Hello Mistress Josephine,
    I have discover your voice and your website on and I like very much the way you talk and write to sissies.
    I think that you explain quiet well some psychological things in which I recognize myself.
    I am often in conflict with my feminine part but the difference with me and other sissies from this site is that I have stop wearing some feminine clothes since something like 15 years (I am 36 years old) so even if I recognize myself in some point of the naghty sissy test, I feel far away of going in the way of chastised sissy. But this fantasm is very exciting for me.
    I would have love to had the oppurtinity to speak by phone or chat with you maybe to try to express my sissy prt but I am living in France. It will surely be difficult to start something. To bad that you weren’t a french mistress.
    Best regards.

  • britney

    Ms. Josephine–sissy britney understands and needs to place priorities in order. sissy britney began transitioning as well. April 3 she began seeing an endocrinologist to progress forward. Since the start, her breasts have slowly begun to develope, but due to work issues has slowed on her feminine practices. she will begin preparing for her further developement as the sissy Ms. Josephine requires. Thank You for the reply.

  • Ms. Josephine – I discovered you on the Denial site and dared to “follow” you here. I have a confession to make – I saw your pretty face in your photo and my silly sissy part suddenly twitched a little bit. To be honest . . . I wanted to touch it. I know – shocking. But I felt that I should confess this to you. Will you grant me the sweet mercy of replying to my comments and give me the general thrusts of what you feel the best Treatment is?

  • Britney

    Ms. Josephine…i am one of these sissy tramps that you so dearly speak of. I have so wanted to speak with you to pull out that gurl inside of me. I am her when I can be, which has been months now, due to my current marriage situation. I have wanted to talk with you and become one of your sissies for so long. Unfortunately, due to the economy, it has been impossible for me to extend my reach beyond your site. I often come here for reassurance in undstanding my place in the world, and to one day service a few big bulls as your servant.

    Sincerely one of your devouted sissy tramps…

    • I know that phone sex and training can be expensive but under the circumstances you don’t have much choice if your wife doesn’t appreciate your inner sissy. You need to save and budget. Its not impossible. Part of being a good serving sissy if to make small sacrifices for your mistress. Maybe do without certain things. Does that make sense?

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