Tag Archives: sissy-billy


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.

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Back to School. I have finished Summer School Semester # 1 and I am now about to start Semester # 2. The Session Break was too short.

This Semester is dedicated to a class curriculum of “Sissy Girl” Home Economics. It is supposed to be a learning experience of what to expect as a Sissy Girlie Cross-Dresser in preparation for readmission to “The Institute for Cross-Dressing Punishment”. This Semester looks like a lot of difficult Sissy Courses and I am already behind in starting my first course and further behind in posting my course report.

My first week course entails the experiences of a “SISSY BABY”.

The following course requirements are:

– The sissy student must not sleep in her big Girl Bed
– The sissy student’s Bed shall be the Tub in Mistress’ Bathroom (it is about the size of a crib)
– The sissy student shall setup the Tub with appropriate Bed Padding, Baby rubber sheeting and little Baby sissy Girl sheeting. She will sleep in this each night
– Immediately when arriving at home, the sissy student is to go to the nursery, put on a diaper and rubber pants and baby romper set
– The sissy student shall insert her mouth spreader to promote sissy baby drooling
– From Monday till Friday the sissy student will only eat Baby Food and Baby Formula
– Before going to Bed sissy student will drink 32 oz of water and accept a “Fleet” enema to make sure she experiences the feeling of being a baby

As a result of this sissy student failing to start the course on time and missing the first two class days, this first week class will be extended another week with requirements not completing until July 1.

With reluctance and trepidation, I went to my first class of Semester 2.

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sissy billy’s Fantasy Island

In the beginning, [sissy billy][] assigned 14 trips to Fantasy Island:

Count | Trip
:—– | :—————————————
1 | [A Maid To Serve my Mistress][1]
2 | [A Pajama Party”][2]
3 | [Director of Nursing][3]
4 | [Being a Little Girl – Part 1][4]
5 | [My Prom Night][5] and [The After-Party][5b]
6 | [Attending Church on Sunday][6]
7 | [Mistress for a Day or a Few Minutes][7]
8 | [If you act like a Baby…][8]
9 | [The Bridal Shower][9]
10 | [A Ballerina][10]
11 | [Sorority Girl][11]
12 | [A Little Girl’s Birthday Party][12]
13 | [Sorority Pledge Hell Weekend][13]
14 | [Here Comes the Bride][14]

[1]: http://institute.cdpunishment.com/2011/09/fantasy_island_-_1_a_maid_to_serve_my_mistress
[2]: http://institute.cdpunishment.com/2011/09/fantasy_island_-_2_a_pajama_party
[3]: http://institute.cdpunishment.com/2011/09/fantasy_island_-_3_director_of_nursing
[4]: http://institute.cdpunishment.com/2011/09/fantasy_island_-_4_being_a_little_girl_-_part_1
[5]: http://institute.cdpunishment.com/2011/09/fantasy_island_-_5_my_prom_night
[5b]: http://institute.cdpunishment.com/2011/09/fantasy_island_-_6_my_prom_night_-_what_came_after
[6]: http://institute.cdpunishment.com/2011/09/fantasy_island_-_6_attending_church_on_sunday
[7]: http://institute.cdpunishment.com/2011/09/fantasy_island_-_7_mistress_for_a_day_for_a_few_minutes
[8]: http://institute.cdpunishment.com/2011/10/fantasy_island_-_8_if_you_act_like_a_baby
[9]: http://institute.cdpunishment.com/2011/10/fantasy_island_-_9_the_bridal_shower
[10]: http://institute.cdpunishment.com/2011/10/fantasy_island_-_10_a_ballerina
[11]: http://institute.cdpunishment.com/2011/10/fantasy_island_-_11_sorority_girl
[12]: http://institute.cdpunishment.com/2011/10/fantasy_island_-_12_a_little_girls_birthday_party
[13]: http://institute.cdpunishment.com/2011/10/fantasy_island_-_13_sorority_pledge_hell_weekend
[14]: http://institute.cdpunishment.com/2011/10/fantasy_island_-_14_here_comes_the_bride

Since she was unwilling to finish these trips on time, she was given a total of twelve more assignments, one from each of the current clients plus a bonus assignment. (The trip listed in italics is different than proposed, because the original was a duplicate.)

Client | Trip | Bonus Trip
:————————- | :————————– | :———
Bitch Baby Brianna Montana | Salon Day | Fashion Model
[Maggie Rae][] | [High Roller][P2_] | [Double Down][P2B]
[Stacee Skye][] | [A Smurfy Centerfold][P3_] | [Smurfed All Night Long][P3B]
[pie clown][] | [Hometown Cheerleader][P4_] | [After the Homecoming Loss][P4B]
sissy baby jamie | _Giant Baby_ | Giant Helpless Baby
[sissy billy][] | Spa Day | For Mistress Rosemarie

[Maggie Rae]: http://institute.cdpunishment.com/profiles/maggie_rae
[Stacee Skye]: http://institute.cdpunishment.com/profiles/stacee_skye
[pie clown]: http://institute.cdpunishment.com/profiles/pieclown
[sissy billy]: http://institute.cdpunishment.com/profiles/sissy-billy/

[P2_]: http://institute.cdpunishment.com/2011/11/fantasy_island_-_high_roller
[P2B]: http://institute.cdpunishment.com/2012/05/fantasy_island_-_double-down
[P3_]: http://institute.cdpunishment.com/2012/01/fantasy_island_-_a_smurfy_centerfold
[P3B]: http://institute.cdpunishment.com/2012/01/fantasy_island_-_smurfed_all_night_long
[P4_]: http://institute.cdpunishment.com/2011/12/fantasy_island_-_the_cheerleader
[P4B]: http://institute.cdpunishment.com/2012/05/fantasy-island-after-the-homecoming-loss

Now, she has until the end of her second summer semester to get them finished.

Or else.

Sissy Summer Dress Code – Panties, Thongs and Diapers

Sissy Summer officially started June 4 and to my dismay I was once again asked (Required) to participate. The “Girlie” Dress Code this summer was an alternating blend of Panties and Thongs every day. My weekend Dress Code remains in affect to my continuing discomfit.

I collected Panties (three) and Thongs (four) for each day of the week and laid them on the Bed for display and inspection by Mistress and then put them in my lingerie draw for use during the week.


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Summer School Session # 2 – June 18, 2012 through July 15, 2012:

Week 1 – Experiences of being a Baby – Sissy Student Assignment and Requirements

– Does not sleep in her big Girl Bed
– Her Bed shall be the Tub in Mistress’ Bathroom (it is about the size of a crib). The Sissy student shall setup the Tub with appropriate Bed Padding, Baby rubber sheeting and little Baby Sissy Girl sheeting. She will sleep in this each night
– Immediately when arriving at home, she is to go to the nursery, put on a diaper and rubber pants and baby romper set
– She shall insert her mouth spreader to promote sissy baby drooling
– From Monday till Friday the Sissy Baby will only eat Baby Food and Baby Formula
– Before going to Bed she will drink 32 oz of water and accept a “Fleet” enema to make sure she experiences the feeling of being a baby

Week 2 – 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.

Week 3 – Housekeeping 101 – How a Sissy should keep Mistress’s House

– Immediately upon returning home she is to go to the dressing Room and put on her Maids Outfit for two hours of Housework
– Monday thru Friday – she is to complete a different Housekeeping duty each night
o Clean all the bathroom
o Clean the kitchen
o Wash all her Nighties and Panties, Iron and Fold
o Vacuum and dust all the rooms
o Act as the waitress, standing by the door for two hours holding a tray of drinks

Week 4 – Fashion Training – Sissy Dress-up Week

– Monday thru Friday – each night will be fancy dress-up
– Dress will be formal gowns and Thursday will be Bridal Gown night
– As a sissy “adult” she will practice her oral service each night
– Ultra feminine Negligee’s required for bed
– Relief and Slurping will be required before going to bed each Night

The “Institute” Mistress School Board has also reviewed sissy billy’s 1st Semester Records and while it’s review is not complete, it has been determined that since she is now on “Probation” the following shall be added to her school assignments. Her Progress is still being reviewed and it is anticipated that further disciplinary actions may be assigned.

Since she seems to be forgetful about her assignments and late in turning in several assignments, for the remainder of the summer, sissy billy is required to install a full time reminder that she is a sissy.

She is to obtain two dildos that can both be mounted on the wall. Each will be mounted 18 inches off the floor, next to the door leading to the garage (one on the inside, one on the outside). For the remainder of the summer, every time she enters (or leaves the house), she will

(1) Get on all fours
(2) Spend 15 seconds giving proper homage to the phallus
(3) Stand up and open the door

So, every time she goes through that door, she will practice her sissy oral servitude before going through the door. Her Mistresses think this will be a way to help her remember her place. Documentation of this shall be included in her first post and report.

Summer School – Semester One

Your First Trimester of Summer School has ended Sissy Billy. There was a great improvement in your lack of attention and effort which is commendable, but you had so far to come from your total Lack of Effort over the first part of this year.

You had 1 B, 1 C, 3 D’s and 1 F. This averages to a GPA of 1.6. Passing is a C (2.0) and therefore you are now placed on Probation.

There is a 3 week intercession before your 2nd Trimester Assignments are developed and your 2nd of 3 Summer School Sessions begin.

The Following Assignments remain in effect and/or Modified. (Subject to further Modification by Mistress Katzenburg)

• Every Friday you will continue to wear panties and stockings to work in preparation for the weekend.
• For improvement in your work Ethic – Your weekend rules will be adjusted to go from 6:00 PM to 6:00 AM each night from the time you get home on Friday, Saturday and Sunday Nights. The Ladies Room is still strictly off limits during this time. A Diaper may be worn if you wish, but it can only be removed at 8:00 AM when you finish each Night. To ensure you stay well hydrated. you are to drink a 16 oz glass of water every hour until you go to sleep. You are to wear a nightgown, stuffed bra and panties to bed each night.
• You will continue to experience your sissy period once per month.
• You will continue to experience your sissy ovulation two weeks after your sissy period begins and will take proper precautions for three days.
• It is now the Summer Season starting June 1. Therefore you will be wearing panties every day. In honor of the “Girlie” Summer of a few years ago, thongs will be included. On Sunday night you are to lay out and photo document 7 panties, 3 normal lady panties and 4 lady thongs. You are to put these in your small lingerie draw and then with your eyes closed each morning reach in and pick one.

Enjoy the Summer, Your Assistant Instructress (Summer School), Mistress Rosemarie

Aissgnment # 2A – “sissy billy’s” Ovulation Time

I am a Sissy that is now having her monthly “Period” at a regular Interval. Mistress tells me that it is part of a feminine cycle that I now “Ovulate” each month. I did not really know what this meant and was sent to research it’s meaning by Mistress.

A Women’s Ovulation time is the 2-3 Days each month when she is fertile. It usually falls in the middle of her Menstrual Period which I have now been experiencing. It is also the time of the month when the egg falls and she can become pregnant. Her hormones are at their peak and she feels her most feminine. It is also the time of the month when she will unconsciously dress her prettiest and have her strongest feelings to get pregnant.

At this time of my sissy life I certainly do not want to get “pregnant” or get anyone else “pregnant” and Mistress is “helping” me with contraceptive protection.

As a result of obsession with Cross-Dressing and the Training and Punishments the “Institute” has assignment to me, another phase of my Sissy Life begins.

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Make-Up Week for “Sissy Billy”

Last Week my Sissy had some personal issues and being the kind and sensitive Mistress I am, I relented and allowed her the week to settle her affairs.

However, as you all know, there are always consequences. Therefore she shall make-up last weeks assignments as she must also do her current week assignment.

1. Complete her Post from Assignment # 3 – Fantasy Island High Roller Trip before going to bed tonight.

2. Complete Assignment # 2A – Ovulation Time – this Tuesday, Wednesday and Thursday.

3. Complete Assignment # 4 – Soap Testing designed as follows:

* The Soap to be tested this week shall be a big white bar of Ivory.
* Testing shall be per the previous guidelines.
* Each morning with her shower using the Ivory, she is also to clean the inside of her mouth during her shower. She shall soap up her pink soft sponge completely and shove it in her mouth for the entire shower.
* At night before going to bed, she shall test the Ivory as a soap-paste and brush her teeth thoroughly.
Results are do next Monday night (It is a long weekend, so she gets an extra day) or sooner.

4. Complete this week’s Assignment # 5 – Fantasy Island trip as a Cheerleader.

* Special Cheerleader Dress Code for a Sissy. Everything Pink. Nail Polish, lipstick, Red Stockings and heels, pink panties, pink stuffed Bra, sheer top and of course her pom poms.
* Her Bonus trip is a punishment for causing the team to loose.
* First a paddling until her “ass” is pink.
* Then a Cheerleader 2 quart enema.
* With legs tied she is to stand in the corner of the Locker Room for one hour as her enema leaks out. No Cheerleader that I know would be able to hold it for an entire Hour. This should prove embarrasing as everyone watches.
* Last she is to suck on the practice dildo for ten minutes and then lick the cheerleader practice vagina for another ten minutes.

Make up Weeks can be exhausting and non forgiving. Since our Sissy missed last weeks assignments and requirements she shall wear panties and pantyhose every day to work this week as a punishment.

“sissy billy” – I was understanding, but I have not talked with Mistress Katzenburg this week and am not sure if she will be. Do not be surprised if she is not as understanding as I and alters your assignments.

Your Summer School Associate Mistress

sissy billy’s Ovulation Time

Now that you are a young “sissy” Lady and are getting your monthly “Periods”, there is also a time of the month where you “Ovulate”. This is usually about two weeks after your “Period” starts each month and after consulting “Auntie Flo” and her menstrual Calendar, it is determined that you will be Ovulating from next Wednesday thru Friday.

This assignment (Let’s call it Assignment 2 A) is in addition to your Assignment # 4 – More Soap Testing which will be issued this weekend and start on Monday.

Assignment # 2 A – sissy billy’ “Ovulation”.

This is a time when a Lady is most susceptible to getting pregnant. We do not want that to happen to you or for you to impregnate anyone else. So your assignment is as follows.

* You are to research and write a paragraph describing a Ladies Ovulating Time.
* When at home (I think you are safe when out in public) you should wear protection. You are to put your sissy clitty cage on and wear it whenever you are home.
* A Lady usually feels sexy and pretty during this time. You should change as soon as you get home into a pretty feminine outfit and then before bed put on a pretty Negligee and wear it until morning. You should wear something different and pretty each night.
* Each night you may (since this is safe and no impregnating can take place) practice your oral technique on your dildo and your vagina.
* After three nights and your “Ovulation” has ended – you are to remove you sissy clitty cage, put on a condom and relieve three nights of pent-up sexual frustration filling it as much as you can. You are then to snip the end and in front of your Mistress such your juices till it is empty.

This should protect your “sissy” virginity.

“sissy billy’s” Rehabilitation Summer – Assignment # 02 – Her Monthly “Period”

I received a Letter from my “Auntie Flo” last Saturday informing me that my feminine Monthly “period” was to begin again and it was indeed to be a horrible girlie “period” because I had missed so many.

I was instructed to prepare as I did when I had my last “period” and went to the store to buy what was needed.


Then I began to worry about how bad it would be and how much it would hurt. A Girlie “Period” is not a lot a fun. And then it began.

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“sissy billy’s” Rehabilitation Summer – Assignment # 1 – A Sissy Shaving

I confess that I have been too long negligent and lazy in being an active sissy student client of “The Institute of Cross-Dressing Punishment”. I have therefore been enrolled in Summer School of the “Institute” by Mistress Rosemarie and with the concurrence of Head Mistress Katzenburg. This was mandatory and it was made perfectly clear that I must pass or I may be expelled. I will attend this Summer School with the utmost enthusiasm and the proper attitude so that I may regain my status as an active sissy client.

So my Summer begins:

Assignment # 1 – Since I had for so long refused to comply with the many past assignments of a Clean Shaven sissy body, I am to do the following:

When I return home on Friday night I am to prepare and take a fragrant sissy bubble bath to soften my sissy skin. I am then to shave my body from the Neck down with strong encouragemnt that I at least utilize a feminine wax kit for areas of my hairy non-sissy body.

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sissy billy has been a Naughty Sissy

I have been silent too long and have not wanted to participate, but I have completely supported Mistress Katzenburg in her attempts to train my Sissy. However, Mistress Katzenburg and I are in agreement and are completely disgusted with your feeble attempts and poor attitude. With urging by Mistress Katzenburg, I will no longer be passive, but will take a more active Role in assiting Mistress Katzenburg and the Institute in your training and punishments.

silly billy has been lazy, arrogant at times, completely negligent of her duties as a sissy client of The Institute of Cross-Dressing Punishment and just plain naughty. She has broken and failed to follow so many “Rules of the Institute” that we could not list all of them. It is time for her attitude to change and her rehabilitation to begin.

Since sissy billy seems not to have enough will power of her own to follow even the simplest rules or demonstrate a proper attitude, I will give her a strict and rigid schedule to follow over the next three months. She will either complete successfully every assignment given her or I will wash my hands of her and I imagine Mistress Katzenburg my suspend her and put her in the Hall of Shame.

“sissy billy” – read your fate below in the following agenda that we have set for you and obey completely.

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Winter Camping All-Client Punishing Sleepover

Between Thursday and Saturday night of this week, all clients are required to attend a punishing sleepover. The sleepover is to last a *minimum* of eight consecutive hours. Required dress for the night includes:

* Panties
* Pantyhose
* Nightgown
* Bra and Extra-Large Breast Forms
* Ankle Cuffs, Ankles locked together
* Wrist Cuffs, wrists locked together
* Blindfold
* Earplugs
* Hood

In addition to the panties in the first bullet, you are free to wear a diaper over them. The panties are not optional. Just know that you are not allowed to get up before the eight hours have elapsed, so wearing a diaper (or two or four) may make the assignment completable without making a mess of your bed.

Speaking of beds, since this is a winter camping punishing sleepover, sleeping in your own bed is not allowed. If you follow in the true spirit of winter camping — outside in a tent — you will be allowed any type of bedding you would like. If you stay inside, you will be sleeping directly on a hard surface floor with your pillow and blankets to keep you company. If carpet it more your style, then you are allotted one thin blanket.

Extra points are available only if you have someone else tuck you in. (They will have to bind you tightly enough so that you cannot get up in the morning until they release you and they will be responsible for taking pictures tat you could not possibly take.)

Sleep tight and ensure the pictures are in the dropbox before Sunday night. No need to make a full post–you can have sweet sissy dreams. In addition to the unmodified pictures, also upload two pictures (in both t and s size) which you think best reflect your situation and a text file with a short description of why your night was the most punishing.

Fantasy Island – Smurfed All Night Long

As related in my previous adventure – A Smurfy Centerfold, the Smurfette’s convinced Mistress that I should stay the night and meet them in the Fantasy Island Smurf Park on the far side of the Island.

I did not like the sound of that, but as usual I had no choice and I was led by Mistress back into the Sissy Salon.

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Fantasy Island – A Smurfy Centerfold

We each have a driving force behind us. A Sissy Submissive like myself is weak and needs guidance. I am fortunate to have Mistress Rosemarie who gives purpose to my life and guidance. As usual, it was her who decided that I have been lacking in attitude and needed a big push. With a Stern voice she told me to get in the car and as we drove to the dock she lectured me continually on my bad attitude. She told me that I better shape up and start behaving like a proper sissy client again of “The Institute for Cross-Dressing Punishment”.

I got out of the Car and headed to the Dock to board the boat for Fantasy Island. Passenger of one headed for her new adventure and what was sure to be my justified punishment.

As the boat neared Fantasy Island I could see the Mistress of the Island smiling as usual and waving to me. I dreaded how happy she always was and how very unhappy I ended up with my adventures.

She smiled as I curtsied as was appropriate for a sissy to do as she approached a Mistress. She told me that Mistress Katzenburg had told her how much I liked Smurfs and Smurf Movies. On this trip I was to have the honor of being the lead Actress in a Smurf Photo Shoot.

Her assistants as usual whisked me away to the Sissy Dressing Room.

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