Maid Academy

The Pennyroyal Maid Academy is currently undergoing a complete overhaul that will include all new videos!

Well, little sissy, I can see that you’re desperately in need of a Mistress with a firm hand to keep you in line and teach you how to be a good little sissy maid. Sissy maids are not born, they are educated and your education seems to be lacking. You’ll need to enroll in the Pennyroyal Maid Academy if you’d like the benefit of my tutelage.

Your instruction commences with an interview to see what your strengths and weaknesses are. From there you are formally introduced to me, your Instructress. After we’ve settled it, it’s time for you to begin your training. The curriculum includes:

  • Rules and Regulations You will be required to memorize My list of sixteen sweet sissy rules and regulations for recitation whenever I see fit.
  • Feminization Basic instruction on how to look the part.
  • Types of Maids Information on the different types of sissy maids that can be trained and a description of the the skills necessary for each variance.
  • Uniform A lecture on a proper maid’s uniform and a list of pre-approved uniforms; your final uniform will have to be approved before you may wear it in My service.
  • Duties A list of nine duties that you will be expected to carry out to my satisfaction.
  • Punishment An overview of the forms of discipline I employ as well as a number of specific examples for wayward sissies.
  • Media Twelve videos for you to view, either for instructional or wanking purposes.

3 Responses to Maid Academy

  1. Ronan Dykes says:

    Dear mistress penny i really wish i could wear all of your silky panties while you are teasing me for being a sissy maid i want to be all of your panties while you are wearing them i want to be the only one to serve you forever and we can wash all of our panties together if i had just one pair of your pink silky frilly french knickers i would lick and wear them constantly i love you and all of your lingerie forever xxx

  2. Ronan Dykes says:

    Mistress penny im wearing pink panties now.

    Please post another video showing your loyal sissy maid subscribers all of your lingerie

  3. Dave Winters says:

    Hello Mistress!

    I live in San Francisco and have had the fantasy of being a sissy for just about as long as I can remember. I decided I wanted to explore this and came across your site and was….mesmerized :)

    I’d really like to talk more about exploring this fantasy with you in person.


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