Category Archives: Activities

2: Why Choose Just One?

**Question:** When you have a choice of three different, humiliating activities you can assign to a sissy like Stacee Skye, why should you just pick one?

**Answer:** You shouldn’t.

Which explains what Stacee Skye is doing right now. She is on her knees in the kitchen floor and has been given a total of 10 minutes to use a straw to suck the piss out of both bottles and then deposit it into a bowl. Whatever she manages to suck out (and not swallow, of course) will be poured into her diaper. Whatever is left will be soaked into her clothes (which I have no plans of changing any time in the near future).

Since she managed to get back inside with the bottles I removed her hard-won long sleeve shirt and replaced the nipple clamps with some more appropriate sized sissy tits. Once she finishes with these two warm bottles, I can think of ideas of how to handle what she bottled up before her trip and left in the refrigerator.

1: A Trip Home

After some time away, it is always good to be back home. Usually. Unless your name is Stacee Skye. She had a decent trip back home today, but due to my instructions arrived with two full 20 oz bottles of her waste generated during the trip. Now, as she kneels beside me, she is wondering what they will be used for.

* Will they be pouring into her diaper? (She is wearing two large diapers plus two diaper inserts. They will surely hold a great deal and the plastic panties and bloomers will ensure that there are no leaks.)

* Perhaps she will be forced to soak her outer clothes (shorts and a pink t-shirt) and then go out and about. If that is the case, I am sure that she is hoping the two [painful clips]( on her nipples will be removed before she is forced to go out. And she is probably hoping that her shorts can be changed since the long-legged, pink, plastic bloomers stick out the bottom of her shorts.

* Maybe she will be required to drink up both bottles with a straw–and that is why I am having her practice sucking on a dildo right now.

The one thing that she does know is that she will have to retrieve them from the driveway–dressed as she is (and with the diaper she has managed to wet)–in full view of all of the neighbors that are out mowing the grass right now. And that has her scared. Scared enough to beg to have something to cover her pink shirt.

I was happy to give her a long sleeve blue shirt to cover the pink ones and to add the condition that the previously unfilled bra would need to be stuffed with two pairs of panties in each cup. Not my usual size, but she is going outside in the middle of the day.

An Irresistible Force

When it comes to training, it always pays to be persistent.

Stacee Skye has spent over a half hour with four [painful clips]( on her nipples. The has brought this punishment on herself by trying to cancel the activity I have planned. But it will not cancel it. The only thing that her pain gets her is a delay. The activity is inevitable.

(This is not to say that she is just wearing the clamps. She also has on a nice corset and long line bra and girdle panties. And a skirt with nice shirt.) And still there is more.

Wooden Paddles.
Anal Plugs.
Menthol Gel.
Ankle Cuffs.
Posture Collars.
Blackout Hoods.
Spreading Gags.
Public Exposure.

They are all on the docket for this evening until Stacee Skye can see the error of her ways. And how many hours can she last with those clips anyway? All Stacee Skye has to do to stop the punishment is beg me to allow her to piss in the bowl of bars of soap that she shredded in the food processor a bit ago. She will eventually do it and the assignment with the piss soaked shredded soap will continue just the same as I had planned it. Just a bit later.

The only question is how long it will take her to realize the inevitability of an irresistible force.

Maggie Rae: Story Assignment 5—Hired Help

First off, I’d like to apologize to everyone—things have been a bit hectic, and I missed my usual Sunday deadline. I hope the amusement that you get from my suffering makes up for it a bit, and trust me, there was a good bit of suffering. [This week’s story assignment]() actually managed to be less pleasant than [Back and Forth](), which I didn’t even think was possible. Like Back and Forth, I was again going to be transporting pennies, though this time as a restrained maid, and before I would be able to complete a penny I would need to perform oral service on a nearby dildo. Combine that with the same 1,000 pennies from the first time I did Back and Forth (which was never going to happen), and horrible consequences for failure, and you’ve got just the latest in my hellish assignments. First order of business, though, was to get dressed…



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Maggie Rae: Story Assignment 4—Another 24 Hours

It could have been worse. It really could have. [This week’s story chapter]() was a little bit of a lull in the action (thankfully), and while this week’s assignment was no where near the [tortures I endured last week](), it was still less than pleasant. 24 hours I would need to spend in the same dress that I was in last week—24 hours gagged, in a super-stuffed diaper and heels with my largest breastforms in. It may not seem like it, but 24 hours can be a long time, especially when you’re gagged for it. Still, Mistress Katzenburg was gracious enough to allow me to avoid being locked in a closet for the full duration like my story counterpart was, so again, it could always be worse.

I was up at 6:00 AM yesterday, dressed and ready for my assignment, and 24 hours later I’m tired, I’m wet, I’m in desperate need of a shower, and I’m ready for this week’s assignment to be over. I’m just crossing my fingers that I can get off this easy for next week’s assignment as well. I can always hope, can’t I?


Maggie Rae: Story Assignment 3—Back and Forth

Let me tell you about the worst night I’ve had in a while, and bear with me because I haven’t had nearly as much sleep as I should have. [This week’s story assignment]( looked bad on its face, many of them do, but it’s not until you’re well into it before you realize exactly how terrible it is. The principle sounds simple enough—my assignment was to transfer pennies one at a time from a cup in one room in the house to a cup in another, with increasingly unpleasant additions as I went. Now, my place isn’t that big, and even spread out as far as possible, there were only about 15 steps between cups—not awful you say, that’s 30 steps per penny. Well, allow me to show you how wrong you would be…


Like most assignments, however, I started by laying out everything I would need beforehand… Ominous, isn’t it?


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Maggie Rae: Story Assignment 2—Fire Down Below

Tonight’s assignment marks the end of the second week of my assignment story series—my ongoing training based off Mistress Katzenburg’s ongoing story. This week, Sean finds himself in a [precarious (and painful) position]( While the assignment wasn’t terribly difficult or (thankfully) humiliating this week, it was both time consuming and very, very painful. My assignment took place in two parts—first, I was to shave from the neck down, which just takes forever when you’re as hairy as I am, and second I was to masturbate with Icy Hot—bringing myself to the edge multiple times, but never cumming. While it was an extremely painful assignment, it did at least distance itself from last week’s humiliation.

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Maggie Rae: Story Assignment 1—A Reckoning

As [previously mentioned](, tonight marks the beginning of my story assignment series—every week Mistress Katzenburg will be adding a new chapter to the overall story and I will be assigned a special assignment based on the week’s chapter. This being the introduction week, I got off relatively unscathed, but it was still an extremely unpleasant (and painful) experience. I know that as the story continues, my assignments will only get more and more humiliating—good for all of you, not so good for me. I don’t even want to think of where I’ll be in a month’s time…

Enough about worrying about the future though—here are the results of this week’s assignment.



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Maggie Rae: Violent Femmes

Nearly a week ago, we active clients here at the Institute received a warning that a new assignment was coming down the tubes, and that it would be based on the timeless music of the Violent Femmes. While we were all asked what our two favorite Violent Femmes songs were, Mistress Katzenburg’s two favorites were ‘36-24-36’ and ‘Dance, M.F., Dance’. From that alone, I knew that nothing good could come of this assignment, but yesterday I found out just how bad it would be.

Since none of us had 24” waists, we were first to figure what our bust and hip sizes would need to be to maintain the same proportions. It turned out that I would need a 63” bust and hips, which meant a bra with my biggest forms and a super-stuffed diaper (since it seemed like it wouldn’t take too long, I omitted the diaper and just super-stuffed my plastic panties—bad choice). After I was dressed I had to make a video for Mistress Katzenburg following the directions of her second favorite song, ‘Dance, M.F., Dance’—you can imagine just about how well that went, in a bra stuffed as full as mine was. If she decides to post the video, then you’ll get to see it as well.

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Maggie Rae: Life Imitates Art

About a week ago, I had a spare afternoon where all my work was done and I had no other real outstanding obligations. To pass the time, I decided to work on my art (I’m not really an artist, but I like to mess around with it none the less). One thing led to another, and before I knew it, I’d finished my first picture in a long time. Wanting to share it, I posted it to Twitter, where it caught the eye of Mistress Katzenburg. Having no outstanding assignment at the time, she decided that my next assignment would be to duplicate the picture that I had drawn. Given how unpleasant the subject matter I’d drawn was, my heart sunk a little, but I pledged to finish my new assignment as quickly as possible…

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Maggie Rae: Full of Shit

A long, long time ago I was given an assignment in response to some unnecessarily mean things that I’d said. At this point, I honestly can’t remember what they were, but they more than warranted a response from Mistress Katzenburg. That assignment was the originally named, Full of Shit. I was to find a recipe that would leave me looking like I’d been covered in shit, post the recipe, then make up a large batch, dress up like a baby, and cover myself in it for the enjoyment of all of you. That assignment unfortunately never happened—life gets in the way, things get put off until later, and before you know it, it’s been five months. I should have known better than to put it off, and I’m sure I’ll pay for it in the long run, but better late than never.

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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]


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]:
[Stacee Skye]:
[pie clown]:
[sissy billy]:


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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