Tag Archives: humiliation

Fantasy Island – A Smurfy Centerfold

We each have a driving force behind us. A Sissy Submissive like myself is weak and needs guidance. I am fortunate to have Mistress Rosemarie who gives purpose to my life and guidance. As usual, it was her who decided that I have been lacking in attitude and needed a big push. With a Stern voice she told me to get in the car and as we drove to the dock she lectured me continually on my bad attitude. She told me that I better shape up and start behaving like a proper sissy client again of “The Institute for Cross-Dressing Punishment”.

I got out of the Car and headed to the Dock to board the boat for Fantasy Island. Passenger of one headed for her new adventure and what was sure to be my justified punishment.

As the boat neared Fantasy Island I could see the Mistress of the Island smiling as usual and waving to me. I dreaded how happy she always was and how very unhappy I ended up with my adventures.

She smiled as I curtsied as was appropriate for a sissy to do as she approached a Mistress. She told me that Mistress Katzenburg had told her how much I liked Smurfs and Smurf Movies. On this trip I was to have the honor of being the lead Actress in a Smurf Photo Shoot.

Her assistants as usual whisked me away to the Sissy Dressing Room.

Continue Reading

Fantasy Island – The Cheerleader

I must admit after my last trip to Fantasy Island I have been putting off another visit. It has been made very clear that my Mistress was dropping me off at the Fantasy Island Ferry today whether I wanted to or not. So – I got on the boat with my normal trepidation and fear. I sat quietly on the ferry boat trip and when we arrived I trudged up the ramp.

The Mistress of Fantasy Island was her usual happy self and was glowing as always. She was excited and told me that I was a sight for sore eyes. She told me I was just in time to fix a big problem she had.

Today was the big game with our rival and that one one of the cheerleaders had just hurt herself. She told me that I was perfect to be her newest cheerleader. I was shocked and started to step backwards.

She looked at me sternly, told me to stop and before I could say anything several of her assistants appeared and led me to the cheerleaders locker room.

Continue Reading

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.

Continue Reading

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.”

Continue Reading

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).

Continue Reading

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 – 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.

Continue Reading

Fantasy Island – 11 “Sorority Girl”

When I was in school I often watched the Sorority Girls and would envy them. They looked like they were having so much fun. I wished back then that I could have joined a Sorority. Even then I wanted to wear the outfits that Sorority Girls did and do the fun things they did.

Here was my chance. When the Mistress of “Fantasy Island” asked what my wish would be, I said that I wanted to be a Sorority Girl.

She smiled and told me that at the local school on the Island there was a Sorority and by Luck, they were having final interviews that night and would tell the girls then and there if they were in the Sorority. I was so excited at the opportunity of finally being a Sorority Girl.

The Mistress said that each year they do take one boy as a special case and if I was sure, she thought she could arrange it. Tonight was the formal interview, so she suggested that I go with her assistant to the Fantasy Island Store. I found a nice pair of slacks, a button down collared shirt and even put on a tie so that I would impress the Sorority Girls.

I returned to the Mistress and after she complimented me on how handsome I looked led me to the Sorority House.

Continue Reading

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.

Continue Reading

Fantasy Island – 9 “The Bridal Shower”

As I walked off the boat and up the Ramp the Mistress of Fantasy Island was waiting to greet me. With a smile, she asked me how she could help a Sissy like myself. I was humiliated as usual when she asked me like that, but with a stammer and a stutter I said that it was always my Dream to be a Bride and to be married to my Mistress.

She clapped her hands with glee and summoned several of her helpers. Looking at me, she said that before I became a Bride and before the Wedding, that of course there had to be a Bridal Shower.

They took me off to the Beauty Salon and started to prepare me for my Bridal Shower. As always I knew this was going to be embarrassing, but I wanted to be a Bride and a Bridal Shower was also a big part of my Dream. To be dressed up in a very feminine dress and to be given a Bridal Shower by all of my Mistress’s Girlfriends was both exciting and humiliating.

I exited the Salon and felt lovely as I was escorted to the Bridal Shower Reception at the local Restaurant. I paused before the doors were opened and I entered.

Continue Reading

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

Continue Reading

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.

Continue Reading

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.

Continue Reading

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.

Continue Reading

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.

Continue Reading

Copyright © 2019. Powered by WordPress & Romangie Theme.