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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Geek Girl: It’s a Maid, Maid, Maid World — Redux

I have spent more time in this outfit than I care to think about: Eight Legged Clean Freaks, In a Row, the first It’s a Maid, Maid, Maid World… This is not a pleasant outfit, especially when the super-stuffed diaper must be messy before any cleaning can actually take place. I am desperately hoping that this is the last time I have to endure this assignment—I’ll take anything else if it means not having to do this again.

Functionally, this assignment was identical to the three that came before it—get dressed up, clean apartment, submit evidence along the way and at the end, proving that apartment is indeed clean. As this was a punishment for doing poorly on my previous assignment, however, new elements are restrictions were put in place to make the assignment even more difficult. First, my wrist cuffs had to be clipped together (which makes for extremely difficult cleaning) and my ankles had to be bound together on a short chain or rope. When you combine the ankle bondage with the super-stuffed diaper, all sorts of misery ensues, just from how you’re forced to walk. I hope this is the last time those two things ever make an appearance in the same assignment. Additionally, I had to mess my diaper before I started, and I wasn’t allowed a change until I finished—I haven’t finished by the way, so four hours later I’m still sitting in the same messy diaper, can I be done yet?

This assignment had a second big twist compared to the first three that merits mention: Instead of simply taking pictures to prove that I’d successfully cleaned, I was to star in a short movie where I present my work to Mistress Katzenburg. She has said that the movie may or may not be posted at a later date, so that remains to be seen. It’s fairly long, considering, and it may end up posing bandwidth issues, so we’ll see.

I would definitely like for this to be the last time I have to deal with this assignment, if nothing else so that I can move on to bigger and better things, regardless of what those end up being. I have finished it, however, and that’s a big monkey off my back, considering all the hang-ups and snags that preceded it getting done. It’s nice to finally put it in the books.

Fantasy Island – 10 “A Ballerina”

All my life I have loved Ballerinas. They were always so pretty and feminine and the Ballerina Attire was so beautiful. I don’t know why I did not ask to be a Ballerina sooner. How can the Mistress of Fantasy Island turn this into an awful wish. I would get to wear a Ballerina’s Tutu and dance with a lot of other Ballerinas.

That was my wish as I approached the Mistress of Fantasy Island. She smiled as always and said that she thought I would make a very pretty Ballerina.

Instantly some of her assistants appeared and led me to the Girl’s Dressing Room. After a short while I reappeared and presented myself to the Mistress.

Mistress smiled and complimented me on how lovely I looked. I felt like a Ballerina. I felt so pretty and feminine and I loved my Tutu.

Mistress led me to the Ballerina Class Dance Studio and introduced me to the Instructress. Then with one of her smiles that I knew meant trouble, she told me to do as the Instructress said and I would have no problem. The way she smiled led me to believe otherwise. But, Oh Well, I did feel like a Ballerina.

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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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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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Maggie Rae: Babyface II, Interim

Over the past month, I have been diligently completing Babyface II, my most recent punishment, as penance for my shortcomings during my reinstatement into The Institute. As I’d mentioned in my last post, Babyface II consisted of two repeats of the initial assignment—unpleasant, but by no means terrible. Together, the two repeats took up nearly two full days—two days of a month long punishment. The rest of that interim period has been what I considered the real punishment. As the punishment dictated, I spent at least 10 hours a day diapered, at least 14 hours a day in my extremely heavy bra and forms, and while I fortunately escaped any additional “tasking”, I still had the intense summer heat to make everything just a little bit worse. Through the course of my 27 day punishment, I went through nearly three packs of diapers, found myself sitting in far more wet diapers than I would have liked, and on a few especially unfortunate occasions, I found myself going to bed and waking up in a thoroughly messy diaper—all experiences that I could really do with avoiding in the future…

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Maggie Rae: Babyface II, Part I

Over a month ago, when I was still in the midst of my reinstatement proceedings, Mistress Katzenburg brought to my attention that I had agreed to recomplete the Babyface assignment as a part of the reinstatement option I’d chosen. I was not terribly keen on the concept, and tried to make a deal to avoid it—I would submit to a reader poll to decide my fate on the repeat. If people voted my way, I would avoid the repeat altogether; while if lost, I would accept my punishment tenfold. I didn’t think it could come to it, but I ended up losing in the polls by 20 votes, and so began the saga of Babyface II.

Babyface II was a direct extension of the original punishment that included two repeats of the original punishment, with a 20+ day punishment time between them for the 20 votes that I lost the poll by. Officially, the punishment was as follows:

Babyface II will begin the same way as the original–as described in the original post. The changes Ms Lisa made are OK–and she is under no requirements to have this one be the same.

http://institute.cdpunishment.com/2010/07/babyface

Since you lost by 20 votes, after this has been completed, the following daily lessons will be enforced.

0) You will continue to be shaved at all times.

1) You will be dressed for bed between the hours of 8pm and 6am. This will include your standard forms, footed jammies and diaper. No change will be allowed during this time, so it should be a good, thick diaper.

2) Diapers and a bra are to be worn any time you leave the house. Panties and a bra will be worn at all other times (except as specified in these rules).

3) You will spend at least four hours of each day (i.e. when you are not dressed for bed) in your forms.

4) You will be available at all times for any tasking your Mistress requires. She will ask you, so be sure to inform her you are available.

5) After twenty nights have elapsed, you may petition your Mistress to repeat the event that started off this assignment and finally end the assignment. On the morning after the 20th night, rule #3 above will change to “all the time you are at home”.

With the poll closed and my fate decided, I set off to accept what I’d brought on myself—a month of extremely unpleasant punishment…

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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: Babyface

A long time ago, at the end of the Dusting Off series of assignments, Ms. Lisa spotted the assignment called Babyface which would be used as the highest level punishment for the ultimate loser of the series. After the completion of Sorority Bitches, she made sure to remind the Mistresses of The Institute so they wouldn’t forget it, ultimately dooming sissy billy to complete the task. Additionally, Ms. Lisa volunteered me for the task, despite my inactive member status at the time. At the time, I laughed at the torment that sissy billy had to endure, and it wasn’t until my time came that I felt the same pain he had. If he had performed his Sorority Bitches better, then maybe we both could have avoided it, but as it turned out, that was not the case. Now, I’m faced with the threat of repeating it, or worse, whatever the next and final step of the Dusting Off series would have been (seeing as I’ve already completed it once) dependent on how the evaluation of my own Sorority Bitches assignment goes. This is a record of my own instance of Babyface…

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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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A Sissy Should Always Clean Up Her Mess

I had just got home from work and Mistress Rosemarie met me at the door. She was mad because I had been fulfilling an assignment/punishment from My Superior, Mistress Myckie Jo Katzenburg from the night before and because I was tired I had not cleaned up my mess. I had been issued an assignment and I was already late in posting and if I failed again tonight to post it I would continue in my punishment for Day 8. I was already wearing panties and pantyhose and it was already Monday. If I failed to complete my assignment by Day 10 (Wednesday) I would be forced to wear a Bra to work and I was desperately afraid of doing this.

Mistress Rosemarie was of a different mindset, however. She told me it was my own fault and that since I did not clean the house last night and it was filthy from my fantasy production, she did not care if I completed my previous assignment or if I received another punishment for being late. This was her house and I was to keep it clean as a sissy to her Mistress should. I was her sissy Maid.

I have many Mistresses. My Superior, Mistress Myckie Jo Katzenburg, Mistress Amber, all the Ladies of “The Institute for Cross-Dressing Punishment” and Mistress Rosemarie. Mistress Rosemarie also reminded me that I was to show respect and obedience to all Ladies and since I was a sissy I was inferior to everyone of the feminine Gender.

I went upstairs and found on the bed my cleaning attire for the evening. I dressed as ordered, returned to the Living Room and upon Mistress Rosemarie’s instructions proceeded to clean the House for the next three (3) hours.

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sissy billy’s Willful Insolence

sissy billy was right when she said “I must learn to keep my mouth shut“. After reading her new standing rules she wrote “I am currently dressed and am on my way to work and already late, but I will shave my legs over the weekend in preparation for wearing my pantyhose on Monday.” Umm, yeah. Rules can take effect whenever she wants them to.

Well how about this instead: when she gets home from work tonight, instead of shaving her legs in preparation for Monday, she will shave from her neck down. Once nice and smooth, she will lock on her sissy clitty prison. It can come off on Monday, when she is ready to return to work.

Is that better? Or do I need to be clearer?

A Stumble – A Quick Punishment to Remember

I made an error last night by once again rushing in my responsibilities as a sissy client of “The Institute for Cross-Dressing Punishment”. All Mistresses and Ladies deserve our total focus and attention to detail. To rush in an assignment, punishment or simple correspondence is a rudeness to be punished.

I had been communicating with My Superior, Mistress Myckie Jo Katzenburg in several emails regarding the kindness she has shown in my latest assignment and in a rush to complete my email to her and because I was tired (no excuses for my indiscretions) I stumbled and made a basic mistake by not addressing her properly by her full name.

It was inadvertent, but a serious mistake and is one of the basic and one of the most important Rules of the “Rules and Regulations”. I am so sorry My Superior, Mistress Myckie Jo Katzenburg.

I have been trying to be very good and obedient for her and hope that she forgives me. A rudeness and mistake must be punished though. My Superior, Mistress Myckie Jo Katzenburg directed me to immediately put on a bra and stuff it, I wore the Panties that I am required to wear full time in stead of male underwear (I usually do not wear anything at night), a Nightgown and supplement this with wrist and ankle Cuffs. I was then to sleep in this prescribed sissy wear until morning when I was to make a post.

I have completed my punishment and made the post as prescribed and beg My Superior, Mistress Myckie Jo Katzenburg for forgiveness. I thank her for her kindness for not punishing me more severely.

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