The Second Semester is dedicated to a class curriculum of “Sissy Girl” Home Economics. It is a learning experience of what to expect as a Sissy Girlie Cross-Dresser in preparation for readmission to “The Institute for Cross-Dressing Punishment”.

My second week course entails the experiences of a “SISSY EXPERIENCING HER PERIOD”.

The following course requirements are:

This week will be devoted to her “period” week. Learning to become a young Lady is critical to her Sissy Development. This course is under the guidance of “Auntie Flo”. “Auntie Flo” will send her reminder and daily assignments prior to the School Week. Attached is the “Period” Memo I received from “Auntie Flo”

Hello Sissy Billy,

I know that you believe your Monthly Menstrual Cycle is not due to start till Thursday, but
Honey, sometimes it can come early and suddenly. So, unexpectedly it you will start your “Period”


Tuesday, June 26, 2012

Tonight without warning it starts. Take 3 feminine laxatives immediately and drink a large glass of water every hour until 9:00 PM. I would suggest you put a Sanitary Napkin in your panties right away.
Your cramping will start at 9:00 PM today. You will accept a full enema and refill each time you must go to the Ladies Room. Your nipples will also swell and throb. Nipple Pins for 15 minutes every hour. Continue
to 11:00 PM and then you can try to go to sleep.

You should set your alarm for 5:00 AM and start your enema simulation of severe cramping for an hour before you may then start to get dressed for work. Since you feel bad, eating lightly is a must. You may eat you normal food, but I strongly suggest you help digest your Food by taking a tablespoon of Castor Oil with it.
You better wear a Sanitary Napkin to work tomorrow.

Wednesday, June 27, 2012

A Bad Day today. Cramping is bad – Drink water all day. This will continue Menstrual Bloating. You should wear maxi pads for the day changing if necessary. Tonight is more cramping enemas for the entire night. When the cramps are too much you may go to the Ladies Room. However, you must refill and re-administer another 2 Quart Enema as usual. Repeat the process until you go to bed.
– Your Sanitary Pads must be smeared with my special “Period”
– Attach clothes pins for 15 minutes before going to sleep.
– Normal Food is OK, but it must be taken with Castor Oil as well as feminine Laxatives before going to Bed.

Thursday, June 28, 2012

Your cramps are stopping, but your Sanitary Pads must be smeared with my special “Period” discharge and you should insert Tampons all day.

Friday, June 1, 2012

Your period is ending, but continue to wear protection today.

Good Luck my young Sissy Girlie Lady.

Best wishes,
Auntie Flo
See you next month.

And So, on Tuesday my “Period” began. It is true that I have been having my “Period” for a number of months now, but it is humiliating to tell about it in a post.

As I am taught to do each month, a sissy should always be prepared for her “Period” and made sure I had everything I needed and laid them out in the Ladies Room.


I knew my dreaded and painful cramping was about to begin, so I put on a pretty Nightie to make me feel better, put a Sanitary Napkin in my Panties and then my nipple sensitizing with Clothespins attached to my Nipples.


Oh My Gosh, my nipples hurt so much. But, I soon forgot my nipple pain as I was led to the bed and the first of my “Period Cramps” simulation began and my sissy bowels and stomach quickly were filled. Oh how it hurt.


For the rest of the night I held the enema and endured the cramping as long as I could. If I begged for relief, I was allowed to go to the Ladies Room, but it was quickly replaced with another 2 quart enema. Oh such bad cramps. When I woke in the morning it continued again for another hour. Finally I was allowed to prepare for work, even though I still had cramps and did not want to go.

As instructed, I put a Sanitary Napkin in my panties between my legs and had to wear onw all day with replacement every two hours.


There is nothing more disgusting and distracting then to have a gunky icky Sanitary Napkin between you legs all day long.

I was so glad to get home and get comfy until I realized my cramping simulation was to begin again. More Enemas.


After two nights my enema cramping finally stopped, but I still had to wear a messy icky Sanitary Napkin and during the day a Tampon inserted in my sissy vagina.

I was glad it was finally done on Friday, but as before, I knew it would come again in a month.


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After reading this I am glad that I still live with my parents because if I lived alone…..IT WOULD BE ME.

Come to think of it,,,it is me, only more discreet.

i love to learn averithing there is to learn about how to be a good sissy maid sluty

Hope Miss Cat doesn’t read this assignment

My belly cramped there last two mornings… I wonder if my period is starting and need tampons?

Aunty Susan trained me to accept a punishment enema (usually Ivory snow flakes in a 2 Quart bag) whenever i had dirty thoughts about women. That was what caused my Willie to stand erect. She took care of my spunk, but taught me that sexual thoughts led to pain at her hands.

    Because I am a sissy girlie girl cross-dresser my Mistress had read sissy billy’s post and decided that since I wanted to dress like a girl that I should also experience my period as sissy billy did above. My enema’s were for the purpose of letting me experience extreme cramping like a girl does with her period. My first Girlie Period was horrific like the one sissy billy was made to endure. Now I have my Girlie Period everytime my Mistress has hers.
    You should feel lucky that Aunty Susan doesn’t read the post above.
    UGH – A girl’s Period is not fun

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