Category Archives: Activities

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.

[![](http://cdpunishment.com/institute/images/2011/11/sissybilly_111122-001e.jpg)](http://cdpunishment.com/institute/images/2011/11/sissybilly_111122-001s.jpg)

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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.

[![](http://cdpunishment.com/institute/images/2011/11/sissybilly_111107-001e.jpg)](http://cdpunishment.com/institute/images/2011/11/sissybilly_111107-001s.jpg)

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In a Row — Alien Invasion — Maggie Rae’s Results

For our most recent assignment, [In a Row 2: Alien Invasion](http://institute.cdpunishment.com/2011/10/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.”*

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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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In a Row 2: Alien Invasion

As a followup to the original [In a Row](http://institute.cdpunishment.com/2011/03/in_a_row) assignment, I require this assignment of all clients. In this assignment, you will acts as the president of an alien race of humanoids set on enslaving the earth. You set up a plan where you will 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).

Unfortunately for you, after leaving the lingerie shoot, you follow what you think are a bunch of people dressed as ghosts. Instead of ghosts going to the party, it turns out to be a klan rally and they don’t take kindly to people of color. You are captured and taken prisoner, where they decide the best they can do is to humiliate and torture you.

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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]( http://institute.cdpunishment.com/2011/04/geek_girl_eight_legged_clean_freaks), [In a Row]( http://institute.cdpunishment.com/2011/04/in_a_row_-_maggie_raes_results), the first [It’s a Maid, Maid, Maid World]( http://institute.cdpunishment.com/2011/08/geek_girl_its_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.

[![][MMMWr1t]][MMMWr1s]
[![][MMMWr2t]][MMMWr2s]
[![][MMMWr3t]][MMMWr3s]

[MMMWr1t]: http://cdpunishment.com/institute/images/2011/10/maggierae_111030-001t.jpg
[MMMWr1s]: http://cdpunishment.com/institute/images/2011/10/maggierae_111030-001s.jpg
[MMMWr2t]: http://cdpunishment.com/institute/images/2011/10/maggierae_111030-002t.jpg
[MMMWr2s]: http://cdpunishment.com/institute/images/2011/10/maggierae_111030-002s.jpg
[MMMWr3t]: http://cdpunishment.com/institute/images/2011/10/maggierae_111030-003t.jpg
[MMMWr3s]: http://cdpunishment.com/institute/images/2011/10/maggierae_111030-003s.jpg

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.

[![](http://cdpunishment.com/institute/images/2011/10/sissybilly_111017-011e.jpg)](http://cdpunishment.com/institute/images/2011/10/sissybilly_111017-011s.jpg)

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.

[![](http://cdpunishment.com/institute/images/2011/10/sissybilly_111015-003.jpg)](http://cdpunishment.com/institute/images/2011/10/sissybilly_111015-003s.jpg)

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.

[![](http://cdpunishment.com/institute/images/2011/10/sissybilly_111012-003e.jpg)](http://cdpunishment.com/institute/images/2011/10/sissybilly_111012-003s.jpg)

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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All-Client Punishing Sleepover

Between Thursday and Saturday night of this week, all clients are required to attend a punishing sleepover. Required dress for the night includes:

* Diaper
* Pantyhose
* Nightgown
* Bra and Large Breast Forms
* Ankle Cuffs, Ankles locked together
* Wrist Cuffs, wrists locked together
* Blindfold
* Earplugs
* Hood

Sleep tight and ensure the pictures are in the dropbox before Sunday night. No need to make a full post–you can have sweet sissy dreams.

**Update:** In addition to the unmodified pictures, also upload two pictures (in both t and s size) which you think best reflect your situation. Additionally, upload a text file with a short description of why your night was the most punishing.

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.

[![](http://cdpunishment.com/institute/images/2011/10/sissybilly_111011-001e.jpg)](http://cdpunishment.com/institute/images/2011/10/sissybilly_111011-001s.jpg)

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“Fantasy” Island Continues

Since [sissy billy][] was unable to finish her series of [Fantasy Island](http://institute.cdpunishment.com/tag/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 |  

[Maggie Rae]: http://institute.cdpunishment.com/profiles/maggie_rae
[Stacee Skye]: http://institute.cdpunishment.com/profiles/stacee_skye
[pie clown]: http://institute.cdpunishment.com/profiles/pieclown
[sissy billy]: http://institute.cdpunishment.com/profiles/sissy-billy/

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.

[![](http://cdpunishment.com/institute/images/2011/10/sissybilly_111003-005e.jpg)](http://cdpunishment.com/institute/images/2011/10/sissybilly_111003-005s.jpg)

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 – 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.

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