A Letter From Auntie Flo

I received this Letter from my Auntie Flo last Sunday prior to my Monthly Period.

Good Morning sissy billy, I am your Auntie Flo.

I am told by your Mistress that you are a sissy going through puberty. Therefore I
will be visiting you once a month from now on for a long time. I will become your
not so best friend each month.

I have looked at your “Period” chart and see that you have had a few light young
girl periods. You may have thought these difficult, but there comes a time in each
young ladies life that she must become use to her feminine difficulties and this
month, unfortunately for you, is the start of your real feminine “Period”.

Every young women experiences their first really “Bad Period” and this will be
yours, with many more to come on occasion. Hopefully for you, they will be few, but
that is dependent on my mood. It is never nice to get Auntie Flo mad at you.

This month your “Period will last for six Days,

I will normally send you a reminder about 2-3 days before your “Period” starts and
you should automatically do your “Pre-Period” prep and on the morning of Day 1 I
will let you know if I am happy or mad and whether it will be light, normal or bad
for your “Period”. No grumbling now, because a girl’s “Period” comes whether she
wants it or not.

Your normal “Pre-Period” prep will be drinking 2 gallons of water that day and when
you go to the Ladies room we do what is called out/in fluid replacement. Since I do
not know how much you have pee pee’d, I expect you to drink 12 oz of water each time.
Also you should take two feminine laxative pills before you go to sleep.

This is what I call a “Bad Period”. I am sorry, but it will happen on occasion.

General Suggestions for each “Period”:

I suggest that you put a rubber sheet on your bed because you may have accidents
with your “Period”.
I want you to buy a little girls Diary and keep a record of everything that you do
or happens during you “Period”.
A Girl’s Breasts swell during there “Period” and their Bras hurt. You will wear a
bra two sizes to small and put a grapefruit in each cup to press against your sore
Some Girls wear “period” panties and an old Nightie. I think it is better and nicer
to wear pretty things. Wear pretty panties and an a pretty nightie each night. If
you soil them, then wash them.

Special assignment for this period.

Some girls say they like to get their minds off a bad period and it makes them feel
better to go shopping. I want to know if this works for you. On Day 4 (which
should be your worst “Period” Day) I want you to dress up and go to the mall to shop
after Dinner. Spend at least 2 hours shopping. Bring Pads and Tampons as you will
probably need to go to the Ladies Room to change them. There must be some things
you need to buy. Splurge. Also window shop. Look for a fancy dress. Describe it
and let me know the price. Buy a pretty scarf for yourself Window shop for
Nighties, describe them with pricing and buy one if you see a really pretty one. I
hope this works for you. Try not to think about your cramps and your “Period”.


Drink 3 Gallons of Water today. This will continue Menstrual Bloating.
Take 2 Feminine Laxatives twice a Day.
You should wear maxi pads for the day changing if necessary.
Accept 12 oz of Lemon Juice in lieu of enema fluid – at night – Hold to bursting.
Attach clothes pins for 15 minutes before going to sleep.
Normal Eating Habits for today.
Douse nipples with Tabasco sauce once before going to bed.


Drink 2 Gallons of Water today. This will continue Menstrual Bloating.
You are allowed to pee 8 times per Day plus out/In 12 oz(Keep record).
Take 2 Feminine Laxatives three times a Day.
2 Tablespoons of Castor Oil – once in morning and once with Dinner.
Baby cereal and 8 oz formula for Breakfast and Dinner, Tomato Soup for Lunch.
Drink a 12 oz Glass of Tomato Juice for a snack before bed.
Sissy should wear maxi pad for day, tampon for 4 hours when you get home and
overnight pad at night.- changing as necessary, but at least every 4 hours.
Attach clothespins each time you are in the bathroom.
Douse nipples with Tabasco sauce once + Clothes pins on nipples for 15 minutes
(twice a day).
Accept 12 oz of Lemon Juice in lieu of enema fluid – in morning – Hold to bursting –
at least 15 minutes before you get out of bad. It is normal for a girl with her
“Period” to have early morning cramping.
Accept a one 2 Quart Enema for one hour and replenish if you go to toilet.
(Immediately when you get home from work)
Accept a 16 oz of warm Mineral Oil in lieu of enema fluid just before you go to bed
– Most hold or let it leak out slowly during the night. You can not change your pad
for at least 4 hours.


Same as Day 2.


Same as Day 3.


Your Period is finally slowing down. Be happy. Cramping begins to slow down, but
bleeding continues.

Baby cereal and 8 oz formula for Breakfast and Dinner, Tomato Soup for Lunch.
You should wear maxi pad for day, tampon for 4 hours, and overnight pad at night.-
changing as necessary.
Accept 8 oz of warm Corn Syrup and 2 oz of water in lieu of enema fluid – just
before bed and Most hold or let it leak out slowly. May not change your Sanitary
Pad for at least 4 hours.


Normal Eating Habits.
You should wear maxi pad for day, tampon for 4 hours, and overnight pad at night.-
changing as necessary.

Good Luck my young Lady

best wishes, Auntie Flo


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Oh My Gosh, I am so glad I was not a girl all my life. I feel sorry for the poor girl that has really bad periods like this. Now that my monthly periods have started I hope that Auntie Flo is kind to me and I never have a period like this again. A normal period will be terrible if it is 1/2 as severe as this.

The Prep of drinking 2 gallons of water gave me a really bulging tummy and a bloated feeling. I tried not to pee, but had to occasionally. Shopping for Sanitary Products was as humiliating as it always is.

Day 1 and drinking 3 gallons of water was impossible. My tummy was bursting and the feminine Laxatives already were working and I was starting to have very loose Bowel Movements. I applied Tabasco to my nipples and clothespins and my breasts were sore and hurting. The enema of Lemon Juice gave me instant cramps at night and they never really went away for the next four days.

Day 2 was the start of three bad days of my period. More water kept me bloated and I could not stay within the 8 pee per day requirement. I peed 13 times that first day and with the added water barely reached 1/2 of my 2 gallon requirement. The Castor Oil made me gag and the Baby cereal and formula which would have made my Bowel Movements loose anyway was made looser by the Castor Oil. I hate the taste of baby food and only managed to gag down half of it. I was also hungry now because I was not given anything else to eat. The Lemon Juice enema in the morning started my cramps and with a bloated tummy and full diarrhea now I had really bad cramps all day at work. It was a busy day and I could not even leave early. I was going to the bathroom every two hours or less and constantly changing my Pads and tampons. Every-time I put the clothespins on my nipples in the bathroom they started aching immediately. They now hurt to even touch and my shirt reminded me of this each time I moved. I got home at night and a two quart enema was waiting. I accepted my enema and with really really bad cramps now crawled into bed and cried. I could not hold it for an hour and had to replace it 2 times as I pleaded with Mistress to go to the Ladies Room. The mineral oil enema at night just added to it along with an overnight bulky pad between my legs. It was tough to sleep. I did not sleep much, but thank goodness for the big pad it caught the mineral oil that I leaked during the night.

Day 3 was the same, but worse as it compounded from Day 2. I could barely go an hour now and even had to stop on the way to work and go to the bathroom at a McDonald’s.

I know now why Mistress is always asking me to stop so she can go to the Ladies Room.

Day 4 was the same except for the special assignment Mistress gave me to go shopping. She coupled this with the assignment that Mistress Katzenburg gave me for the additonal soap test and after my 2 quart enema when I got home, I prepped as required and I was off to the Mall.

I went to the Bath and Body shop and purchased all of the girlie smelling soaps and lotions that Mistress Katzenburg directed. It was embarrassing in the the Bath and Body shop. It almost smelled as bad as the Perfume stores. I was the only sissy (man) in the store. There were 2 female sales Ladies that constantly asked if I needed help and several other shoppers (all women). I swear some of them looked at me thinking, what is he doing in here. I then went to other stores as directed by my Mistress. I saw a really pretty prom dress (Pink is my favorite color) that cost $ 129.00. It was a little humiliating again being the only sissy (Man) in the dress section. I then went to another store and shopped for nightgowns. At least there was one other man in this store. I also shopped for a scarf to buy, but could not find one that I liked or thought Mistress would like.

The results of this assignment. It did not make me feel better, in fact my cramps got worst and I had to go the bathroom twice in 1 1/2 hours at the mall. I did bring pads and tampons as directed. I would rather have stayed home in bed.

Day 5 finally had me doing less than previously, but the cramps were still there. At least the water dropped off and the bloating was less. I still had to wear all the sanitary products which is necessary, but a real pain. Mistress kept applying this cottage cheese/red strawberry mix on my pad that was uncomfortable and looked like what I guess a used girls pad might look like. Disgusting and uncomfortable.

Day 6 came and finally me period was ending.

This was really terrible and I hope I never have a really bad period again like this. Although I imagine my next period in a month, a normal period I hope, will not be much fun either.

I am destined now to have a period each month. I hope you other sissies are spared the terrible difficulties in entering puberty and having your period.

As part of my period this month Mistress made me go online and sign up for a Period calculator to track my monthly cycles. She just told me that about May 25 I should expect my next visit from Auntie Flo. Oh Goodie! I can hardly wait – not.

sissy billy

To all that may be wondering, I skipped my period this month. I am quite certain that I am not pregnant. Big Smile on sissy billy’s face. That, I am guessing, would be really hard.

Mistress Rosemarie tells me that when a girl (sissy girl that I am) starts her period it is not uncommon to miss a few periods. I am hoping I miss all of them during the summer.

I hope that it never comes back, but Mistress Rosemarie tells me that only Auntie Flo knows.

sissy billy

    I would happily do this if told to. The painful cramps of being a sissy I dream for. I’d gladly add add additions as instructed but no modifications/deletions to Auntie Flo’ excellent commands.

Wow. I cannot imagine having to deal with this! Mistress Rosemarie is a force to be reckoned with! What did you do to bring this on sissy billy?

Auntie Flo is absolutely right, all sissys should have periods, I am carrying out as much of the event as I can. If you like the clothes then you have to accept having monthly periods, no matter how painful.

Auntife Flo what an excellent concept sissy monthly periods . As a CD since age 8 ( closet type) and been married twice so have been well aware of the monthly problems girls face yet never coupled it with.cross dressing but what and excellent punishment .

I think this is s lot of work for someone who should be useful and reducing a lady’s work load. So if he is to be put in sissy feminine clothes which is of course a very good idea, he should at the same time be trained to do housework plus practising serving duties so that the family can sit down to dinner waited on by a well trained maid servant who will clear up after then clean the kitchen. Of course if he is a close relation, son or nephew for instance, then there is no need to pay him any wages and of course no days off.

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