Tag Archives: plugged

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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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 – 14 “Here Comes the Bride”

Since this was supposed to be my last visit to Fantasy Island and it had always been my life-long dream to be a Bride, I had planned to ask the Mistress of Fantasy Island if I could please be a Bride.

Not knowing really what to expect from my extension of visits, I figured that this might be my last free wish. So I decided that I should stick to my original planning.

“Mistress – Please grant my wish to be a Bride and may I dress up as the prettiest frilliest Bride ever and attend a my Wedding.”

As always – she smiled and granted my Wish. I was whisked off by her assistants to the Bridal Salon to prepare for my Wedding.

As I came from the Bridal Salon Mistress said I looked Lovely. Then Mistress walked me to the steps of the Church and as the Doors were opened and the music started I could see the Church was packed with My Mistress’s friends. I was somewhat embarrassed to walk down the isle as a Bride, but it was my dream and I stepped out with courage.

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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 – 7 ” Mistress for a Day or a Few Minutes”

As I was traveling to Fantasy Island on my next visit I was thinking about how much I had been punished and how much it had hurt and how much it was terribly humiliating.

I thought – How nice if it was I that was the Mistress and I was in charge of training and punishing the sissy clients.

The more I thought about it the more my sissy mind got the better of me. When I approached the Mistress of Fantasy Island I just blurted out that I wanted to be the Mistress of “The Institute for Cross-Dressing Punishment”

I was amazed when she just smiled and said OK.

I could hardly control myself. I followed one of her helpers to get dressed in what I thought was proper Mistress Attire. I even came up with a mask like Mistress Katzenburg’s hood. Well, not quite – it was actually a pair of lacy thong panties. In my mind it was perfect though.

I was taken to the “Institute” and led into a room of sissy clients. I could hardly contain myself. I instructed one to bend over and immediately spanked her until she cried. Several others I inserted butt plugs into their sissy vaginas and issued other assignments.

How much fun was this?

Then the door opened and in walked Mistress Katzenburg. I almost fainted on the spot.

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Fantasy Island – 6 “Attending Church on Sunday”

My last visit to Fantasy Island proved to be very stressful. In hopes of a quiet and peaceful Sunday I thought I would make a wish to just attend Church which would give me an Hour or so of peaceful quiet and to think about my life as a sissy of “The Institute for Cross-Dressing Punishment”.

The Mistress of the Island told me she thought that was an excellent idea and asked if I wished to attend Church with her. Not thinking anything could be wrong with her invitation, I accepted. She called one of her girls and told me to go with her. Church on Fantasy Island was not a place that you wore pants to. She said her girl would pick out a nice dress for me.

I thought that was a great idea. I do love to wear pretty dresses.

After an hour of fixing I was presented to the Mistress wearing stockings, white heels and a feminine conservative white dress. She also gave me a scarf (Ladies always wear something on their heads to Church) and Gloves (Proper Ladies also wear gloves to Church). Mistress smiled and told me I looked Lovely.

We walked to Church with several other Ladies from the Mistress’s Office and it was a delightful Sunday Walk. As we turned up the Church Walk I noticed for the first time the name of the Church.

The First Women’s Church of Fantasy Island

I should have thought something strange with the name, but did not. I entered talking with the other Ladies.

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Fantasy Island – 3 “Director of Nursing”

At one time I thought how great it would be to be a Director of Nursing. Even better the Director in a Private Clinic where there would be no regulations. I would be the Boss of all those Women and would be able to get back at all those women who did not understand me and always seemed to be domineering and dominant over me.

So, on this trip to Fantasy Island, I said that I wanted to be the Director of Nursing of a Private Women’s Clinic of only Female Doctors and Nurses. I was granted my wish and showed up for my first Day of Work as Director of Nursing. I even dressed appropriately as the Director of Nursing. White Blouse, pale pink Skirt and a Red Crinoline to add a feminine touch, stockings and white 2″ High Heels.

A tough lesson to learn when you visit Fantasy Island is to be very specific in what you wish. Mine did not turn out the way I thought it would.

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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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Maggie-Rae: Sissy Inventory & Sissy Shopping

Back when I chose to fail my original reinstatement assignments, Mistress Katzenburg required me to create an inventory of all my sissy clothing, accessories, and toys so that she might better craft my future assignments and punishments. Having seen my completed inventory, she decided that it was severely lacking and prescribed a remedy in the forms of a sissy shopping trip with Ms Lisa to the local thrift stores. Ms Lisa was to decide my attire for the trip, as well as if I would be forced to try on the clothes that we picked out there in the store, a prospect which wholly terrified me. So that you may judge for yourselves the state of my sissy inventory, and enjoy my unfortunate experience during my sissy shopping trip, here are the results of both…

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Maggie-Rae: Reinstatement Wrap-up

When I applied to be reinstated as a member of The Institute back in January, I was given a small number of relatively easy tasks to complete before I would be formally be re-admitted. I completed those simple assignments, but I was lax in my posting of them—not only lax, but careless and rushed. Toward the end of my write-ups, I was in so much discomfort that I was just scribbling down anything that came to mind, formatting be damned. Furthermore, when Mistress Katzenburg gave me the option of reattempting the posts, I wanted no more to do with them, and so resigned myself to a new series of five punishments: Daily lessons, where I spent 4-6 hours a day in my largest bra and forms for more than a month, with nothing but panties available for underwear; Geek Girl: Subjugation of the Silver Surfer, where I had to download a large number of image galleries while dressed in a humiliating, often painful manner with extras chosen randomly; Geek Girl: Eight Legged Clean Freaks, where I was forced to clean my apartment in the extremely humiliating and uncomfortable garb of a sissy baby maid; a Sissy Inventory and a Sissy Shopping Trip, to detail for Mistress Katzenburg the sissy clothing and accessories available and to purchase new clothes for that inventory; and finally Geek Girl: Mouth of the South, a series of five uncomfortable, humiliating, downright painful tasks that I completed to the best of my ability (however badly they may have turned out).

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Application for the position of Reference Librarian

During the course of my training and punishment for Cross-Dressing as a sissy client of “The Institute for Cross-Dressing Punishment” a system of demerits was devised by Mistress Katzenburg to grade my failures and try to instill additional incentives to succeed for this sissy. Many demerits were added privately from Mistress Katzenburg to me and some publicly. I have many demerits and I had no idea how I would be able to get rid of them. I knew I would eventually be somehow punished for each and every demerit for each and every failure.

I wish to thank Mistress Katzenburg for presenting several possibilities for this sissy to make up for her failures. As a sissy will usually do, I chose the most innocent appearing of the challenges afforded me.

I chose to submit my application for the position of a Reference Librarian. Only time will tell whether I chose wisely or not. I drafted an initial application with the following thoughts.

Every Librarian I have known has been prim and proper. I put on my white bra, slightly stuffed (Most Librarians have small boobs), white panties, pantyhose, a white slip, white low heel shoes, and a librarian’s dress. I also put a bow/ribbon in my hair. As I stood in front of my mirror I looked at myself in the mirror.

As I looked in the mirror Mistress Rosemarie walked in and asked if that was what I really thought a Reference Librarian for “The Institute for Cross-Dressing Punishment” would look like as the “Institutes” Reference Librarian.

I knew that if I submitted this picture with my application that Mistress Katzenburg would quickly put my application into the rejection box. Back to my closet of sissy accessories I went.

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How I spent my summer vacation – Episode 2

It was a normal Summer Saturday and Mistress Rosemarie had laid out my sissy maid outfit that I was to wear for cleaning the house this week. I am sure that every sissy is made to clean her Mistress’s House and that was normal.

Let me rephrase that. Dressing as a sissy maid for Mistress Rosemarie and other Mistresses of “The Institute for Cross-Dressing Punishment” is never normal. The Mistresses always seem to have a way of making every simple cleaning day an adventure in reminding me of what it means to be a sissy maid. There always seems to be corsets, cuffs, sissy clitty cages, diapers or something terrible and uncomfortable to hinder my cleaning routine. At least today I was given my 2″ heels instead of the 5″ heels (when I am really being punished) to wear.

Well I dressed as instructed and presented myself to Mistress Rosemarie for the “sissy-do” list of cleaning chores that she would require me to do.

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Maggie Rae: Suckswell Again

In my last assignment, I was instructed by Mistress Amber to dress as a sissy slut in bondage and orally service Ms. Lisa’s strap-on dildo—an assignment I took too lightly, neglecting to package my boy-parts and performing the entire assignment flat chested. Due to my negligence, my punishment was to first repeat the assignment—this time in proper form—before switching positions to service the sizable naughty-chair dildo while exposing my backside to Ms. Lisa for her to administer as she saw fit. It was to be a most unpleasant night of correction, however one I much deserved, and have learned a valuable lesson on thoroughness from…

The evening began with the transformation from wayward boy into sissy girl—Ms. Lisa had me try on a number of outfits before she settled on a bra-pantie set and a pink plaid skirt, perfect for allowing full rear access. My hair was done up into sweet little girl pigtails, and my face painted up to match the part. Once hair, makeup, and outfit were completed, we moved on to packaging up my boy-parts, which proved to be a bit of an adventure as—while the definition was clear—neither of us really had any clue as to exact technique. In keeping with the stipulations of “as uncomfortable as possible”, we selected an unfinished jute twine (a natural, very scratchy material) for the task and set about wrapping until everything was concealed below a bundle of scratchy lines. With my bits suitably buried, Ms. Lisa produced a pair of black water balloons to fill out the bra she had selected—they were a bit of a stretch, and the bra could only barely support them, but eventually she made them fit. She produced a length of rope and proceeded to bind my hands as a final bit of preparation before the punishment commenced in earnest.

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Maggie Rae: Suckswell

This is my first post since joining the Institute, detailing my first assignment—I was to dress as a sissy slut in bondage while giving oral service to a strap-on.   This task was not the easiest thing in the world, as for the moment, my collection of “sissy” clothing is not as extensive as I would like it to be.  After conferring with my partner Ms. Lisa, however, we managed to achieve a setup and an outfit that did justice to the assignment.  Using what little clothing was available to us, Ms. Lisa’s collection of makeup, a length of rope, a mouth spreader, and our own special “naughty chair”, we managed to achieve a very uncomfortable, humiliating situation.

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With Crumpets – Chapter 1 – MJ on Fire

As MJ came through the door from her break, she was keenly aware of the vulnerability her condition showed. A bright dress set-off the posture collar and her wrists that were locked to it. The ankle cuffs locked together just above her spiked heels insuring she couldn’t run even if she wanted to. The hood and blindfold ensuring that she couldn’t see who was watching her.

As she was walking through the house, break time over, she was reminded of this vulnerability and all of the fires burning through out her body. Continue Reading

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