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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, 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.


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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A Summer Kickoff Weekend for a naughty sissy

This all started out rather harmlessly about a month ago. I had been particularly rude to Mistress Katzenburg and even though I had apologized profusely expressing my sincerest regrets, I was wrong and Mistress was right (as she always is) and I deserved to be punished and given an assignment.

I was surprised at how simple the assignment seemed to be. I was to find several recipes for making of fake cum. Sounds rather simple, does it not. I searched and searched the internet and really only found two. I unfortunately was taking my time and not corresponding with Mistress about my difficulties. As you all know, that is a real no-no.

Last week I guess Mistress Katzenburg had enough and in concert with Mistress Rosemarie, decided that since it was summer that it was only appropriate that this sissy start the summer off right with a “Sissy” Weekend.

Oh My, did I wish I had been more responsive with my simple assignment.

My assignment of finding the “FAKE CUM” was withdrawn. I am sure, however, that it will surface again as Mistress Katzenburg never forgets any failure of mine and they are often revisited in a much harder form.

I was to find a nice sissy e-card on the internet and write a private sincere apology to her.

I was also to wear a very stuffed diaper and extremely stuffed bra for a 12 hour period for one night of the weekend without changing. As most of you know this is always a disgusting assignment.

Also in honor of Mistress Amber’s Summer of Panties two years ago when I had to wear feminine and pretty thongs to teach me a lesson, I would be required to wear a thong and bra when at home until I completed my post.

The rest of the weekend would be filled with little fun assignments devised by my Two Mistresses.

I was to document on an hourly basis to ensure my compliance. I dug out all of my prettiest thongs.

An so a sissy’s summer weekend started

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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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In a Row – sissy billy’s Results

It has been Mistress Katzenburg’s desire to have of her sissy maids all in a row performing household duties for her. This is the weekend for all of us to demonstrate our talents and win the honor of being her best Maid.

The normal accessories were ordered as part of her standard maid outfit. A bra with the largest forms one has and they better impress her. A super stuffed diaper always is a nice accessory and a collar. This week’s sissy maid dress however was to be handmade to demonstrate the talents of each sissy. A black garbage bag was to be found, a belt and white towel as a simple apron and instead of Cuffs, this week we put on 10 lb weights for the ankles and 2.5 lb weights for the wists. Just a little difficulty added to our workload.

All we had to do now was dress up and report for duty.

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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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How I spent my summer vacation – Episode 4

It has been quite a while since I have related another of my summer experiences with Mistress Rosemarie. I was supposed to do this on a regular basis, but forgot and to be honest put it off since my summer vacation was mostly humiliating with many embarrassing activities, trips and things with her. Well the year is almost over and as all things do it has caught up with me big time. This past summer often found me in hot water, but none more so then when I tend to embarrass Mistress Rosemarie in front of one of her friends.

The specific day was a nice warm day in August and we were suppose to go to the beach with one of her friends from work. This was always fun and mostly stress free for me since Mistress Rosemarie was seldom inclined to embarrass me in public by having me do girlish things. It was Saturday and when we went to pick up her girlfriend she explained that she had her period, did not feel good and really did not want to go to a sandy beach. I had been looking forward to this and I lost it. I cried and before I thought, I said I didn’t care if she had her period, she could stay home and we should go without her. No sooner were the words out of my mouth and the look on Mistress Rosemarie’s face told me I had crossed the line. I knew it was insensitive and I knew I would regret it.

Mistress Rosemarie left the room with her friend and when they came back smiling they told me it was about time that I had my first feminine period. I blushed a deep red, but knew better then to say a word. Well out came the feminine sanitary products and their fun began and my misery started. Her friend seemed to feel better that she had a girlie sissy to commiserate with. I was very much embarrassed by this day that I had hoped never to have to relay it for all to hear.

I somehow never learn my lessons though. Last week I made the same awful insensitive mistake again with another one of her friends because it interfered with us going out to a party. She was totally livid and then she remembered my unlearned lesson from this past summer.

Well, this has now become – How I spent my summer vacation – 4 and also how I spent my Christmas vacation – 1.

This past Tuesday Night I came home to find Mistress Rosemarie with both of her girlfriends that I had embarrassed by being insensitive about their periods. They reminded me about how I had said to all of them that I did not see what the big deal was about a little stomach ache and having to wear a rag between there legs. Well, Mistress Rosemarie then smiled and said that it was about time that I realized what a big deal it was.

I was led into the bathroom and spread out on the counter was my impending lesson.

I was to have my first feminine period and I would certainly learn what the big deal was after 24 hours. I groaned, but there was no way out of this now.

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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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A Trip with my Mistress

I made a big mistake at the end of last year. A sissy does not have any rights and only has the obligation to please her Mistresses. She is a sissy and should be kind and sharing with all and therefore has an obligation to other sissies also. She should be honest. But most of all she has an obligation to perform her sissy duties without prodding or insistence from her Mistresses.

Simply, she should Volunteer.

I did not and therefore I am where I am now. I am sorry Mistresses and other sissies. The correct thing to do would have been to show everyone how excited I was over my presents from Mistress Rosemarie and to share this excitement and tell everyone what I got. I was too embarrassed to do this and now I have to physically wear and show everyone my new things.

It is our Anniversary and Mistress Rosemarie decided that we should take a nice trip and that my main purpose was to pleasure her enormously. I was also to bring my presents because she intended to make good use of them. I packed my Suitcase including my very pretty negligee I received from her for Christmas, several other negligees so that I would look pretty for her each night and of course the new two quart enema system, new pink soap, condoms, a Bridal Magazine and of course panties, bra and pantyhose that I would wear full time for the weekend. She examined my suitcase, found it complete and off we went.

Packed and the suitcases loaded in the car we drove off on Day 1 of our trip. Mistress Rosemarie drove as she is a much better driver then a sissy could ever be. She began to explain what would happen on our trip and I began to blush and worry already. She decided that my humiliation should start now and she had me put on a pretty women’s kerchief and tie a bow at my chin. When we passed cars I was to look directly at them. We were away from home and little chance of exposure, but it was humiliating and Mistress Rosemarie even slowed up sometimes so they could get a good look. It was humiliating. This was just the start.

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Fluffy Diaper

I can’t wait for Stacee Skye to get here, because hopefully I’m going to be able to give her some training that she’s needed for a long time. I’m just going to get her dressed up and let her go about her business until she pisses her panties. And since she can’t hold it like a big girl, I’ll have to put her in a diaper. The good news for her is that since she is coming off of a road trip, she should be fairly close to the bursting point and it shouldn’t take too long for her to make a mess.

I haven’t had a chance to go out and get her some real little girl diapers, but I did manage to gather a collection of oversized cotton panties. Combined with some absorbent toweling, it should be enough to keep it all in and make her waddle about. And no big girl diapers would be complete without at least one pair of panty hose over the whole thing. Besides, the hose should do a decent job of keeping any messy leaks contained.

Now I know that Stacee Skye has no interest in using the diaper like the baby she is, so I may be required to help her along in filling her diaper by having her hold an enema while she pulls the diaper back on. If this still doesn’t work, I’ll eventually fill the diaper for her. I wouldn’t want to use these measures too early–she’ll be spending 5 times as long in her diaper once she messes it as it took to get it messed in the first place. So if it takes her a couple of hours to mess it, she’ll be sleeping in her dirty diaper all night.

I see she’s almost here. When she arrives, she’ll find this note on the door:

You are to put on a pair of panties and a new bra (both of your choosing). Stuff the bra with more pairs of panties. Then get dressed and you can go outside to have a cigarette.

You are NOT to use the restroom.

I will call for you when I am ready for you.

Such fun is planned.

Getting Ready and The Truth

When I visit Stacee Skye, I expect her to be ready for her training to commence as soon as I arrive. I don’t like to be kept waiting.

Since she didn’t have the plugs out and ready for use I had her fetch them and then put the smaller goes in immediately–no lubricant allowed. It may have been needed, but that’s not my problem. I also insisted she be wearing high heels up until she goes to the store. I had planned to make her life easier, but she didn’t show me the same courtesy and on they went.

She also didn’t have the forms out and ready to go. So before I allowed her to put them in she had two clothespins put on each nipple. Hopefully she has learned to be better prepared next time.

When Stacee Skye came back inside earlier after I sent her out to the garage, she insisted the she needed to go to the bathroom, so I allowed her to remove the plug and then she couldn’t go. After cleaning her out a couple of times, lo and behold, she didn’t need to go anymore. If she doesn’t want me getting a proper kit to actually fill her up, she better start telling the truth soon.

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