Tag Archives: gagged

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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SUMMER SCHOOL SESSION # 2 – WEEK 1 – CLASS STUDY OF THE EXPERIENCES OF A BABY

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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SUMMER SCHOOL SESSION # 2 – “SISSY GIRL” HOME ECONOMICS

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.

Maggie Rae: The Good, The Bad, and the Pink

It has been a while since I have posted an update for The Institute, for a number of reasons—some good, some quite bad. When it comes down to it, I have broken one of the most important rules of The Institute: When a client will be out of town or unavailable for an extended period of time, they must notify the Mistresses of The Institute ahead of time. I did not do that, and I have been away for an extended period of time, during which I shirked my Institute duties. That was the bad part. The delightfully good part is that, over the past few months I have been developing a closer and closer relationship with a good friend of mine, which has rapidly become something far more special. While I was away from the Institute, I was instead with my new Mommy Venus (who is extremely eager to step up the intensity of my already humiliating and painful Institute activities) who made sure that my time away was not spent pleasantly…

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Invasion of the Sissy Witch from OZ

The Wizard of Oz had called the Wicked Witches to an emergency Meeting and as a Sissy Witch I was commanded to also attend. The Wizard told the Wicked Witches that he needed some place to send all the Munchkins which were annoying the hell out of him.

He told them to conquer another world somewhere over the Rainbow and to do it quickly.

Now none of the Wicked Witches really wanted to get their green hands dirty (they would rather taunt the Munchkins), they decided that the Wicked Witch of East would take me as her Witches Army thinking that with her powers and my ugly looks, the people of this other world would quickly give up.

So I dressed accordingly in my prettiest ugliest Witch outfit and we left for earth.

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In a Row — Alien Invasion — Maggie Rae’s Results

For our most recent assignment, In a Row 2: Alien Invasion, we were to dress up as alien invaders of Earth—very confused alien invaders I might add, with our primary tactic of invasion being a lingerie photo-shoot and the crashing of a Halloween party. I’m not sure I get it either, but that’s the story, and I’m sticking to it. In the words of the assignment:

”To dress as the buxom alien for the lingerie shoot you will be painted from head to toe with a colored cream make-up (you get to pick the color, which cannot be white), then in your largest bra (stuffed) and panties.”

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In a Row – Alien Invasion – Pieclown’s Results

I was require for this assignment to act as the president of an alien race of humanoids set on enslaving the earth. I was to have a lingerie shoot showing off your buxom, but oddly colored, human form which every newspaper will want to run and then meet up with others from your invasion at the largest halloween party in the world (where you will all blend right in).

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Fantasy Island – 12 “A Little Girl’s Birthday Party”

As I walked up to the Mistress of Fantasy Island my mind was racing. It seemed whatever I wished for, the results of my wish were not what I thought they would be. Actually they had mostly been disasters and were truly painful and humiliating. What should I wish for?

Then I thought, how bad could a little Girl’s Birthday Party be. She dressed up in a pretty Dress and had fun with her Girl Friends and got lots of Presents.

Settled – I asked for it to be my Birthday and to attend a Little Girl’s Birthday Party in my Honor.

As usual, Mistress smiled that smile that always gave me chills and dread. Her answer, “Of Course”

Her assistants came rushing out as usual and grabbing my hand took me off to the Little Girl’s Store.

An hour later I was decked out in the prettiest lacy-est frilly Little Girl’s Party Dress. It was so little Girlish that it was humiliating. No Girl would wear it, let alone a sissy boy and not be embarrassed. I must admit though, I did like it very much and felt very Girlie in it.

I was led off into another room and as I entered all of Assistants to the Mistress yelled surprise. I had expected a lot of other little girls to play with, but all the Big Girls meant something else was planned.

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Fantasy Island – 8 “If you act like a Baby…”

The end of my last Fantasy was absolute retribution by all the other sissy clients for my power trip as a Mistress and the meanness that a real Mistress would not have shown.

I cried and screamed and yelled some very un-sissy-like words. I have to admit though that it was deserved.

Finally they brought me back to the Mistress of the Island and they themselves returned to the “Institutes’s Training Center” which was located on the far side of the Island.

The Mistress of Fantasy Island then told me that since I had acted like a Baby, then I would be treated like a Baby

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Fantasy Island – 4 “Being a Little Girl” – Part 1

I have always wanted to be a Little Girl. Little Girls always have a lot of fun and they get to dress up so Pretty. I entered Fantasy Island dressed as a pretty and feminine Girl and asked if I may be a Little Girl with no Worries.

Then the Mistress of the Island looked me straight in the eye and with a smile, told me I would have no worries, but that I must start at the begining. Now where do Girls start. Naturally they start as Little Baby Girls.

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Maggie Rae: Babyface II, Part II

Way back in January, around the time I was making the ill-planned choice to fail my initial reinstatement assignments, I never really thought it would ever get this far. Truth be told, it was long enough ago that I have no idea what I was thinking, but it was my decision and I’ve done my best to live with it. Nearly six months, a long list of assignments, and the first of two Babyface repeats later, I finally found myself staring at the last of the series—one last and final repeat of Babyface to go and the long, painful, humiliating chain would be complete. This repeat would be different, however, as it would be the first and only of the three that Ms Lisa would not be administering, meaning it was all on me to make good on my promise to make this punishment miserable and humiliating enough to satisfy the last of my obligations. I’ve never found it easy to create punishments for myself, however this time I feel that I managed well enough to put this whole mess to bed, once and for all.

And so, without further ado or delay, the last in my long series of reinstatement obligations and the completion of Babyface II…

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Geek Girl: Eight Legged Clean Freaks

Even after enduring her hellish torments at the hands of the evil sorority sisters in Mouth of the South, Geek Girl’s torments were not over yet.

It took Geek Girl almost three hours to waddle back to her apartment across town barefoot. Long enough that her sweatsuit was almost dry now. She had considered taking it off, but after a quick dip in the fountain in front of the college’s administration building, the smell stopped invading her nostrils and she decided to leave it on. Luckily she had not seen anyone out on the early Saturday morning, and she breathed a sign of relief as she shut her apartment door behind her.

Geek Girl waddled to the bathroom and started the water in the tub. A nice long soak and a nap would help her attitude immensely. She stripped off her sweatsuit quickly and went to pull off her diaper. What she had thought were plastic panties with super-strong elastic were actually reinforced kevlar panties with locked aircraft cable ties. Her diaper wasn’t coming off without some heavy duty tools. Tools Geek Girl didn’t have. She checked out the tag on the panties and it simply said “Come back when you are ready to be changed.”

Apparently her adventure was not yet finished.

I was so not looking forward to whatever punishment these sisters could come up with.

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Geek Girl: Mouth of the South

Following my choice to fail my initial reinstatement assignments I was introduced to my new persona of Geek Girl, the big-breasted bad luck girl whose lust for humiliation always seems to get the best of her. When we’d last left Geek Girl, she was sitting alone in her apartment downloading gallery after gallery of humiliating porn, safe and innocent enough. It was when she ventured out into the world to seek the same humiliation she’d seen online that she really got herself into trouble.

Geek Girl became obsessed with sorority initiations and decided to go down to the local college and do a little peeping. After scoping a few of the houses, she finally found one with a window that she could look in, while still providing her some cover from the street. Her patience was rewarded as she looked in and saw several young ladies, looking downcast, wearing only panties and holding large paddles out in their hands. Entranced as she was, she only realized after the snapping of twigs and the sweet smell of chloroform that she had fallen into their honeypot.

As Geek Girl woke up, she could feel ropes encircling her ample breasts, still inside her black sweat suit, and keeping her tied to a wooden chair. With her hands roped behind the chair back and tied to her feet, she knew they had her. And when she found her hair was tied down, keeping her looking at the ceiling, she knew she was truly stuck as their prisoner until they decided to release her. After this beginning, the thought of what they had planned for her both excited and terrified her.

After what seemed like hours or staring at the ceiling, listening to whispers in the corners of the room, Geek Girl was surprised when a girl wearing a leather helmet and brightly painted lips leaned over into her field of view. Geek Girl listened closely as she began.

“As we like to keep control of our own property, without the involvement of outside law enforcement, we offer you two choices. The first is that you will stay with us for a little while and endure the punishments that we have voted and laid out for you. While they will be painful and humiliating, they will be over quickly. Your second option is for us to call our local police, who do not take kindly to peeping toms. With the judge and police chief being alumnae of our sorority, you can be guaranteed at least six months in jail, where we will do everything in our power to ensure that ‘dropping the soap’ in the men’s shower will be the high point of your day. Every day.

“So, do you want us to call in the police? Or will you submit to our punishments? Before you answer though, let me at least tell you what they are. In ‘Artsy Fatsy’ you will be made up for a more appropriate look for the rest of the time. ‘Fire n the Icehole’ will keep your mind occupied while performing ‘Mouth of the South’. With ‘Way Down a Creek’ you will experience what I assume you came here to see. And finally, after ‘The Golden Child’, you will be sent away. That is all you need to know. So, do you accept our punishments?”

“No police” was all Geek Girl could manage to whisper.

Below are the details of the five tasks—how they were applied to Geek Girl and how I implemented them.

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