Tag Archives: fantasy-island

sissy billy’s Fantasy Island

In the beginning, sissy billy assigned 14 trips to Fantasy Island:

Count Trip
1 A Maid To Serve my Mistress
2 A Pajama Party”
3 Director of Nursing
4 Being a Little Girl – Part 1
5 My Prom Night and The After-Party
6 Attending Church on Sunday
7 Mistress for a Day or a Few Minutes
8 If you act like a Baby…
9 The Bridal Shower
10 A Ballerina
11 Sorority Girl
12 A Little Girl’s Birthday Party
13 Sorority Pledge Hell Weekend
14 Here Comes the Bride

Since she was unwilling to finish these trips on time, she was given a total of twelve more assignments, one from each of the current clients plus a bonus assignment. (The trip listed in italics is different than proposed, because the original was a duplicate.)

Client Trip Bonus Trip
Bitch Baby Brianna Montana Salon Day Fashion Model
Maggie Rae High Roller Double Down
Stacee Skye A Smurfy Centerfold Smurfed All Night Long
pie clown Hometown Cheerleader After the Homecoming Loss
sissy baby jamie Giant Baby Giant Helpless Baby
sissy billy Spa Day For Mistress Rosemarie

Now, she has until the end of her second summer semester to get them finished.

Or else.

Fantasy Island – After the Homecoming Loss

Oh My – yet another trip to Fantasy Island. On a previous trip I was nominated as an honorary member of the Fantasy Island Cheerleader Squad. It was not an honor for me, but a very humiliating experience. I mistakenly caused our team to loose by falling (I think I was pushed by the other Cheerleaders) onto the field causing a stoppage of play as we were going to score and as a result we lost. It was all my fault.

Now, as I got off the Ferry, Mistress smiled as she always did as the Cheer-leading Squad rushed out of the building, grabbed me and took me into the Cheerleader’s Locker Room. Today was just a practice of the Ladies Soccer Team, but they were told and remembered how I had ruined the Boys Football Game. I was told that they were looking to punish me for being such a bad Sissy Cheerleader. Girls can be so mean.

Another Fantasy Island Experience begins:

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Fantasy Island – Double Down

I am once again destined to travel to Fantasy Island. Assignment # 3 is my Bonus Trip – Double Down. I still remember my first trip to the Fantasy Island Casino and I know that this trip to the Casino will not be any more fun than my first trip to the Casino.

As I departed the Ferry – I was whisked away by the Fantasy Island associate Mistresses to be prepared. Instead of a sleek Dress, this time I was being taken to a private room of High Roller Mistresses and I was to be dressed in the sleaziest Peignoir Lingerie, the largest bra and forms and a matching thong. High Heels, of course and Makeup.

I was led to a not so private Bath where the clientele could walk in and out and naturally they all did to ridicule me and humiliate me. I was stripped naked and finally was allowed to submerse my self in my Bubble Bath.

It really is humiliating taking a bubble bath in front of a lot of Casino Patrons. If only my night ended with this.

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Make-Up Week for “Sissy Billy”

Last Week my Sissy had some personal issues and being the kind and sensitive Mistress I am, I relented and allowed her the week to settle her affairs.

However, as you all know, there are always consequences. Therefore she shall make-up last weeks assignments as she must also do her current week assignment.

  1. Complete her Post from Assignment # 3 – Fantasy Island High Roller Trip before going to bed tonight.

  2. Complete Assignment # 2A – Ovulation Time – this Tuesday, Wednesday and Thursday.

  3. Complete Assignment # 4 – Soap Testing designed as follows:

  • The Soap to be tested this week shall be a big white bar of Ivory.
  • Testing shall be per the previous guidelines.
  • Each morning with her shower using the Ivory, she is also to clean the inside of her mouth during her shower. She shall soap up her pink soft sponge completely and shove it in her mouth for the entire shower.
  • At night before going to bed, she shall test the Ivory as a soap-paste and brush her teeth thoroughly. Results are do next Monday night (It is a long weekend, so she gets an extra day) or sooner.
  1. Complete this week’s Assignment # 5 – Fantasy Island trip as a Cheerleader.
  • Special Cheerleader Dress Code for a Sissy. Everything Pink. Nail Polish, lipstick, Red Stockings and heels, pink panties, pink stuffed Bra, sheer top and of course her pom poms.
  • Her Bonus trip is a punishment for causing the team to loose.
  • First a paddling until her “ass” is pink.
  • Then a Cheerleader 2 quart enema.
  • With legs tied she is to stand in the corner of the Locker Room for one hour as her enema leaks out. No Cheerleader that I know would be able to hold it for an entire Hour. This should prove embarrasing as everyone watches.
  • Last she is to suck on the practice dildo for ten minutes and then lick the cheerleader practice vagina for another ten minutes.

Make up Weeks can be exhausting and non forgiving. Since our Sissy missed last weeks assignments and requirements she shall wear panties and pantyhose every day to work this week as a punishment.

“sissy billy” – I was understanding, but I have not talked with Mistress Katzenburg this week and am not sure if she will be. Do not be surprised if she is not as understanding as I and alters your assignments.

Your Summer School Associate Mistress

sissy billy has been a Naughty Sissy

I have been silent too long and have not wanted to participate, but I have completely supported Mistress Katzenburg in her attempts to train my Sissy. However, Mistress Katzenburg and I are in agreement and are completely disgusted with your feeble attempts and poor attitude. With urging by Mistress Katzenburg, I will no longer be passive, but will take a more active Role in assiting Mistress Katzenburg and the Institute in your training and punishments.

silly billy has been lazy, arrogant at times, completely negligent of her duties as a sissy client of The Institute of Cross-Dressing Punishment and just plain naughty. She has broken and failed to follow so many “Rules of the Institute” that we could not list all of them. It is time for her attitude to change and her rehabilitation to begin.

Since sissy billy seems not to have enough will power of her own to follow even the simplest rules or demonstrate a proper attitude, I will give her a strict and rigid schedule to follow over the next three months. She will either complete successfully every assignment given her or I will wash my hands of her and I imagine Mistress Katzenburg my suspend her and put her in the Hall of Shame.

“sissy billy” – read your fate below in the following agenda that we have set for you and obey completely.

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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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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.

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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.

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Fantasy Island – High Roller

I ask myself how I ever got myself into this mess. All I did was request a few months off to take care of some personal Business. My re-instatement has become long and trying. The Moral of this all is that all sissy clients of “The Institute for Cross-Dressing Punishment” should realize and accept that they are naughty and that this should never be a part time experience, but must be dealt with on a continual basis. I will think twice about asking for a little time off the next time. But then again, I never seem to learn quickly. However, back to the task at hand.

I am restarting my assigned trips to Fantasy Island. This time the script is dictated by other clients and Mistress Katzenburg.

As I approach the Mistress of Fantasy Island she informs me that she wants to go to the Fantasy Island Casino and will teach me to be a High Roller. I am whisked off by her assistants to dress for the occasion.

I am to wear a slinky dress, a large bra and forms and a matching thong. I present myself to the Mistress.

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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 – 13 “Sorority Pledge Hell Weekend”

As usual I could not make up my mind as I walked up to the Mistress of Fantasy Island. My mind, however, was made up for me quickly by the Mistress.

She asked if me if I remembered my Fantasy Island Wish about joining a Sorority. I, of course, nodded yes. Well then, she said, it is time for your Sorority Pledge Hell Weekend. I shuttered having read many articles of what they did to Sorority Girls during Hell Week. I was quickly dragged by the Fantasy Island Assistants to the Dressing Room and returned to Mistress after an hour of Sorority Girl prepping.

She complimented me about how I looked like the perfect Sorority Pledge and took my hand leading me to the Sorority House.

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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 – 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.

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“Fantasy” Island Continues

Since sissy billy was unable to finish her series of Fantasy Island posts and complete her return to The Institute, I have decided to give everyone the required opportunity to help her finish. In addition to finishing the four trips that she has left on her own, she will be doing one for each client of The Institute (plus a bonus one from me for each client that responds). And if the clients choose not to respond–do you really want to find out?

All clients below are to email me a title and description of sissy billy’s trip to Fantasy Land by Saturday the 15th.

Client Trip Bonus Trip
Bitch Baby Brianna Montana Salon Day  
Maggie Rae High Roller Double Down
Stacee Skye A Smurfy Centerfold Smurfed All Night Long
pie clown Hometown Cheerleader After the Homecoming Loss
sissy baby jamie Rubber Mannequin  
sissy billy Spa Day  

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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