Tag Archives: cheer-me-up

Junior Summer – 2 – Training Starts and The Surprises Keep Coming

“Oh My Heavens” sissy billy uttered. She was frozen in the middle of the floor and looked terrified. She obviously was afraid to move. She finally took a step forward and with hesitation she opened the front door.

There stood Mistress Rosemarie. sissy billy let out a sigh of relief for she had hoped Mistress Rosemarie would be her first trainer. Her hope was short lived. She told Mistress Rosemarie she would be right back as soon as she put on her clothes, but as she turned Mistress Rosemarie shouted stop. She grabbed sissy billy’s hand and dragged her outside still dressed in her peignoir set, cuffs and punishment high heels. She stopped on the front lawn and in the middle of the day there were lots of neighbors outside. The humiliation was intense for sissy billy and she turned red. Mistress Rosemarie then dragged her the rest of the way to the car like a little girl and sissy billy jumped in the front seat. Mistress Rosemarie made her get out and get in the back seat. She then said very loudly so all the neighbors could hear: “Sissies are like little girls and they should sit in the back seat. She then made a big deal of buckling sissy billy in with a seat belt and I am sure sissy billy could hear all the neighbors laugh and start talking. They then drove off.

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Junior Summer – 1 – Is Summer Great or Maybe Not

Bill had just finished his third year of College, was in a real partying fraternity and had been dating a drop dead gorgeous girl (Marilyn) for two years and who had just graduated. She had been in a Sorority that socialized often with his fraternity. He knew everyone in her Sorority including Marilyn’s cousin (Rosemarie) who was in his classes and who had become his best friend besides Marilyn. The three of them had become inseparable during the past two years.

Good Times and things were going to get better. Bill was going to go home with Marilyn and stay at her house for the Summer. Marilyn’s Mother owned a large Women’s Clothing Fabrication Company and was wealthy. He would work there, make good money, continue dating Marilyn and live high on the hog in a gorgeous house.

Nothing could possibly go wrong unless he screwed it up with Marilyn. Well Guess What? Bill screwed it up big time. Bill had a fetish all of his life which he had carefully kept a deep dark secret. He liked to dress up in Ladies frilly feminine negligees. He had always been discrete and very careful and certainly intended on continuing this way. Marilyn’s Mother, being wealthy, had the prettiest and most expensive Peignoir Sets that he had ever seen. He couldn’t wait for the opportunity to try them on and it quickly presented itself.

Patricia, Marilyn’s Mom, traveled often as the head of the company which left Bill alone with Marilyn. How perfect was that? Marilyn and he could do what they wanted. There love life was fantastic. Marilyn, now that she had graduated, was going to work for her mom and would start in the Accounting division so as to learn from the bottom up. Bill was also assigned to that division which was perfect and he liked being close to Marilyn. Rosemarie was also working in this division as she would also the following year go to work for her Aunt.

Marilyn was working hard to learn everything she could and would often work late while Bill would go home to the estate, swim in the pool and sit at the bar at the pool drinking and waiting for Marilyn. Marilyn had told him she would be late and the opportunity presented itself. He went directly to Patricia’s room when he got home, took off his clothes and started trying on her prettiest Peignoir Sets. He lay on her bed and jerked off into the panties that were part of the set. He was in Heaven Until….


A camera clicking startled him out of his fantasies and he noticed Marilyn snapping picture after picture. He jumped up, snapped the camera from her and ran back to his bedroom. He was naturally trembling, but felt relieved that at least he had the pictures and somehow would talk his way out of this. Marilyn walked by his now locked door and yelled, “I will be waiting in the Den for you”.

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Cheer Me Up Story Contest – Chapter 3

Chapter 3 of the [Cheer Me Up Story Contest][1] is due on next Sunday. If you have posting privileges, you are to only save a DRAFT. All of the stories will be published on Monday morning. All of the rules can be found in the [original post][1].

New clients: Since you have not been required to write the two previous episodes, you have an option: You may write (and illustrate) chapters one and two following the rules to wipe out any outstanding punishment that you have. (One chapter removes one punishment.) If you don’t have outstanding punishments, this can be used in the future, at my discretion. Do not take this lightly—this may be the easiest punishment you ever have.

Suspended Clients: If you are readmitted to The Institute, you will be required to catch up on all stories you missed. Therefore, you may wish to stay up to date at this time.

[1]: http://institute.cdpunishment.com/2009/03/cheer_me_up_story_series

With Crumpets – Chapter 2 – Contractually Obligated

MJ wasn’t sure what all happened after she opened the door. Mistress M seemed excited and welcomed in Mistress Tea, but Mistress Tea never said anything, and with the blindfold and hood, MJ had no idea who she was. The worry about the identity of this mysterious Tea was soon forgotten as MJ found herself laying on what seemed like a picnic table bench. With a quickness and strength MJ rarely saw, M soon had her in an upside down hogtie. After tightening some straps around her legs and replacing the gag, MJ assumed that M must be pleased. At least she had finished fiddling.

“I’m sorry I can’t offer you some coffee, Mistress Tea,” M started, “my maid is a bit tied up at the moment. At least I can offer you this much more comfortable seat.”
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pieclown: Dream or ? – Part 2

[Pieclown](http://institute.cdpunishment.com/profiles/pieclown) turned to look at the door. It was the desk clerk, the woman, who had hit him with a pie in the face. Julie stood there with a scared little smile. [Mistress Amber](http://institute.cdpunishment.com/profiles/amber_shummer) spoke “Pieclown, this is Julie, oh right you two have already met. Julie has been in contact with me. She is interested in becoming a mistress for
[The Institute](http://institute.cdpunishment.com/) I have been instructing for a short time. Today she will get some hands on training. Since she is not quite a mistress, you will refer to her as Miss Julie. Pieclown stand up and say hello.” Pieclown stood up, turned, and said “Hello, Miss Julie”. Miss Julie took a step in, but Mistress Amber held up her hand. “Pieclown are you going to welcome her in or should she leave?” asked Mistress Amber. Continue Reading

Cheer Me Up Story Series

When I originally started the with a [Cheer Me Up][1] story assignment, I knew that I wanted it to be a series (hence why the first one ended in a cliffhanger). I just didn’t know exactly where I wanted to go. I have since figured that out. More detailed instructions will be assigned later, but this is the overall structure the stories will start out with:

1. **Cliffhanger** – The chapter ends with a cliff hanger.
2. **Revelation** – The chapter includes a surprising revelation (or plot twist) about one of the main characters.
3. **Concurrent Flashback** – The chapter is a flashback which occurs during (1) or (2), which involves another main character. During the chapter the character must have an opportunity to interact with the characters in the main story line, but they are not required to do so. (If this is confusing, think of the movie [Pulp Fiction][2].)
4. **Cliff Hanger 2** – Back at the main story, the chapter again ends with a cliff hanger.
5. **Integration** – The concurrent flashback merges with the main story line
6. **Short 1** – A short vignette, peripherally related to the main story.
7. **Choices** – The majority of the chapter is based on a choice made by one of the characters, and it ends with a open ended choice. (If the choice is to be made by a person based in reality, who is not the author, that person will be required to make the choice. Otherwise, I will make it. The answer will be delivered with the assignment for Chapter 9.)
8. **Short 2** – A short vignette, peripherally related to the main story.
9. **Consequences** – The results of the choice to be made at the end of Chapter 7 is revealed, and the consequences of it are played out.
10. **Short 3: Art** – A short vignette, peripherally related to the main story, in which all of the main characters are involved in some sort of artistic project.

Though it is subject to change (or be lengthened), I have made this list available so that you might be able to plan your story out a bit better (and not be in too much of a bind when you find out what is coming next). As a general rule, I despise the use of [deus ex machina][3]. It’s just too convenient.

**Update (August 2, 2009):**
In order to have a single link to point back to, I am add the rest of the rules for the story here:

* The story is to be fiction.
* The client is to be the main character in the story.
* The story is to be told in a [third-person narrative][4].
* The story is to be illustrated with at least three new pictures.

[1]: http://institute.cdpunishment.com/2009/02/cheer_me_up_1_-_cliffhanger
[2]: http://www.imdb.com/title/tt0110912/
[3]: http://en.wikipedia.org/wiki/Deus_ex_machina
[4]: http://en.wikipedia.org/wiki/Third-person_narrative#Third-person_narrative_mode

With Crumpets – Chapter 1 – MJ on Fire

As MJ came through the door from her break, she was keenly aware of the vulnerability her condition showed. A bright dress set-off the posture collar and her wrists that were locked to it. The ankle cuffs locked together just above her spiked heels insuring she couldn’t run even if she wanted to. The hood and blindfold ensuring that she couldn’t see who was watching her.

As she was walking through the house, break time over, she was reminded of this vulnerability and all of the fires burning through out her body. Continue Reading

pieclown: Dream or ?

Dream or ?

Pieclown could not believe he was doing this. The recent winner of the power ball was going to do something out of the ordinary. He was driving to meet his mistress. Not some 20 something hottie, but a woman that would put him through the ringer. Amber Shummer was this woman. Pieclown had met her a few years back, on the web site Institute of Crossdresser Punishment. She was in charge there and started requesting and then instructing pieclown as a member of the Institute. Winning the powerball, pieclown took care of the taxes, bills, savings, and tithing. He then contacted Mistress Amber about a possible meeting. She was open to the idea only on her terms. So here was pieclown driving across several states to meet with her.

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