Tag Archives: cuffed

Maggie Rae: Story Assignment 5—Hired Help

First off, I’d like to apologize to everyone—things have been a bit hectic, and I missed my usual Sunday deadline. I hope the amusement that you get from my suffering makes up for it a bit, and trust me, there was a good bit of suffering. This week’s story assignment actually managed to be less pleasant than Back and Forth, which I didn’t even think was possible. Like Back and Forth, I was again going to be transporting pennies, though this time as a restrained maid, and before I would be able to complete a penny I would need to perform oral service on a nearby dildo. Combine that with the same 1,000 pennies from the first time I did Back and Forth (which was never going to happen), and horrible consequences for failure, and you’ve got just the latest in my hellish assignments. First order of business, though, was to get dressed…

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Maggie Rae: The Good, The Bad, and the Pink

It has been a while since I have posted an update for The Institute, for a number of reasons—some good, some quite bad. When it comes down to it, I have broken one of the most important rules of The Institute: When a client will be out of town or unavailable for an extended period of time, they must notify the Mistresses of The Institute ahead of time. I did not do that, and I have been away for an extended period of time, during which I shirked my Institute duties. That was the bad part. The delightfully good part is that, over the past few months I have been developing a closer and closer relationship with a good friend of mine, which has rapidly become something far more special. While I was away from the Institute, I was instead with my new Mommy Venus (who is extremely eager to step up the intensity of my already humiliating and painful Institute activities) who made sure that my time away was not spent pleasantly…

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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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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.

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pieclown:Sorority Bitch

When Mistress Katzenburg gave the assignment of Dusting Off she let us there would be a poll to see who did it the best. The winner would not have to do the next assignment. I was not the winner so had to participate in seven of the nineteen activities, spread over the four sections. One from each section.

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sissy billy – a Sorority Bitch

A short while ago we were all given an assignment. Because the Institute had become quite dusty, we were to present ourselves as a sissy maid prepared to clean. A Poll was established to vote on who had presented themselves as the most humiliated sissy maid.

The losers were to be trained further and experience further humiliation as “Sorority Bitches”.

From the Start my performance was inadequate and had 0 Votes until a late surge left me with 2 Votes, but still in last place. I guess I was the most in need of humiliation and training by the Sorority and now I was to be a “Sorority Bitch”.

The assignment was basically that you were to experience a Sorority initiation Training Exercise in obedience and humiliation. There would be four Training Sessions over the course of the Evening divided into a Pleasant Dinner at a reception hall followed by a punishment session for insolent Sorority Bitches. You were then to be taken back to the Sorority House for some additional Training Punishments. Then, finally, it was Bedtime and a pleasant Sleep. The actual training episodes were not so pleasant.

It was for each of us to determine our training activities. We were required to pick at least one activity in each session, a minimum of 7 total activities and the Judges were to decided which Sorority Bitch would graduate and which would need further training.

I intended to try as hard as I could to impress the Judges and would attempt as many activities as I thought I could accomplish. To start, I strove to make myself as pretty as I could and be the Best Sorority Girl I could. I was to attend a Dinner at a reception hall and the dress code was a Corset, stockings, high heels and a dress. Since it seemed like a formal affair, I chose an old, but very pretty Fancy Dress that I once imagined wearing to a Prom.

I stood ready to be a Sorority Bitch.

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sissy billy’s Makeup Punishment for Mistress Rosemarie

Mistress Amber never forgets:

Out of the blue she noted that I had failed to complete and actually never started a punishment that Mistress Rosemarie assigned me for embarrassing her. My original punishment was for taking the sissy way out of accepting a punishment by saying that I could never wear clothespins on my nipples for more then 1/2 hour. I accepted the fact that I had ignored this punishment and accepted the punishment from Mistress Amber that I was now required to complete it. I accepted and started my punishment.

Day One:

Mistress Rosemarie intended for me to place clothespins on my nipples for just 1/2 hour on the first day. Since I was already wearing wrist and ankle cuffs per my Standing Training rules I put the cuffs on also. I also had lots of my panties to iron. I had not had clothespins attached to my nipples for several weeks now and I forgot how much they hurt. I did complete my half hour and felt good that I had done so. My nipples were already sore, but I knew the real punishment would be Day three and four.

There was one huge mistake I made. I did not tell Mistress Rosemarie that I was completing the assignment she had given me. She was so mad that I went and hid in my room. When I finally got up the courage to go back downstairs she had calmed down, I thought. All she said was that the conditions had changed and we would be starting again tomorrow. Then she sent me to my room to think about how much trouble I was in.

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sissy billy’s Standing Training Rules – A SUCCESS – 2009-May-31

A Success:

Mistress Amber has been so kind to allow me to tell you about the first small success I have had in my first two months of trying to become a worthy sissy of the “The Institute for Cross-Dressing Punishment”. This is only a small one night completion of a punishment, but I am very proud of it. I want to thank Mistress Amber in my training in becoming an obedient sissy.

Saturday Night – 2009-May-30:

It is Saturday night and I am home for the evening. I have put on my ankle and wrist cuffs and my sissy clitty cage. I have also put on my new pretty Lilac Peignoir. I have included pictures so you can see. Isn’t it really pretty and feminine. I just love it. As instructed by Mistress Amber when I dress in my sissy clothes at home I am to wear my big bra and I have made bigger water balloons that please Mistress Amber stuffed in my bra.

I have decided that tonight I am not going to just give in and accept a punishment and hope for the best. I am going to succeed tonight, not only in wearing my cuffs as the assignment dictates, but also in wearing my pretty peignoir all night. I am not going to take them off even if I lay awake all night long.

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sissy billy’s Standing Training Rules – Punishment – 2009-May-30

How I have disappointed Mistress Amber

Confession: On Friday Night, which was a non work week night, I tried to sleep with my cuffs on, but failed to keep cuffs on my wrists and ankles for the entire night. I was very tired and thought that I would be able to go to sleep, but at 1:00 AM after laying in bed for two hours I was still wide awake. I then gave in to my sissy weak willpower and decided to take off my cuffs.

Punishment: I rolled the dice and the number 3 came up. Therefore the punishment is as follows: Punishment # 3. sissy billy is to make a bedtime snack of Level 1 and 2 baby cereal, vegetable, fruit and while wearing cuffs, sissy clitty cage, Stuffed bra and a thong eat the whole snack. After she has finish the baby snack she may take off her sissy items and climb into bed with a 4 oz bottle of baby formula and drink it. The sour taste of baby formula all night should remind her of being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.

Completed Punishment: I got out of bed, kept my sissy clitty cage on and put on a red thong, kept my cuffs on, put on and stuffed with water balloons a big bra and then I went down stairs to the kitchen to make my sissy baby snack. I used only Level 1 and 2 baby food and made baby cereal, added baby vegetables (squash and carrots), added fruit (Plum and peaches) and then poured baby formula into a baby bottle. I added too much baby formula to the baby cereal and it was really soupy and looked even worst then the last time I had to eat baby food. I also made more then the snack portion required by mistake, but once I had made it I knew I would have to eat what I made. I then went back up to my bed and sat on the edge of the bed to start eating my snack. Finally when I finished the food, I took off my sissy items, took my sissy baby bottle and lay down in bed to drink it and go to sleep. I took appropriate photo’s to document my punishment for all to see. I still had problems going to sleep because the sissy baby food snack was sitting in my already stuffed stomach from dinner. I could still taste the icky baby food and since I was not allowed to wash my mouth out our brush my teeth, the baby formula taste coated my tongue and mouth. As I lay in bed trying to go to sleep with the awful taste of pasty and icky sour tasting baby formula in my mouth, I thought about why I am such a sissy and can not successfully complete the assignments that Mistress Amber gives me. I will try to be a better sissy in the future. I should be thankful that Mistress Amber is helping me to become a better sissy and I will try to please Mistress Amber more each day with my training.

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sissy billy’s Standing Training Rules – Punishment – 2009-May-25

How I have disappointed Mistress Amber

Confession: On Sunday Night, which was a non work week night, I failed to keep cuffs on my wrists and ankles when I was in the house.

Punishment: I rolled the dice and the number 2 came up. Therefore the punishment is as follows: Punishment # 2. sissy billy will stuff a bar of wet Pink Camay soap into her mouth, put clothespins on her nipples, High Heels, cuffs, sissy clitty cage, and a thong and stand in front of the mirror for 5 minutes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.

Completed Punishment: I put my sissy clitty cage on with a red thong, kept my cuffs on, put high heels on, placed a clothespin on each nipple and then shoved a fully wet Pink bar of Camay soap into my mouth. I took appropriate photo’s to document my punishment for all to see and then faced the mirror for 5 minutes as timed on the kitchen timer. While I stood facing the mirror for a full 5 minutes I recited to myself a part of one my punishments previously given to me by Mistress Amber. Mistress Amber and the other Mistresses and Ladies of ‘The Institute for Cross-Dressing Punishment’ are always right in their attempts to correct a sissy like me. I should be thankful that Mistress Amber is helping me to become a better sissy and I should learn by my mistakes and correct them.

sissy billy’s Standing Training Rules – sissy billy Confession 2009-May-25

sissy billy’s Standing Training Rules had only been issued last week, but already I am in trouble and must confess to Mistress Amber. I love a pretty negligee, but I can never sleep at night while wearing one and that should be easy for a sissy. This was true with my diaper training and now more so with the selected activity of having to wear wrist and ankle cuffs while in the house. I sleep in the house, so therefore I should wear them to bed as a reminder that I am the sissy in training and Mistress Amber is in Control. Mistress Amber has thoughtfully tried to help in my learning to sleep as a sissy by constantly assigning sleep time activities. Since last week I have worn the cuffs while in the house, but have had to remove them to sleep. Last night I laid in bed until 1:00 AM trying to learn to wear them and sleep, but could not. I took them off. Today was a Holiday, so it was not bad. I do need my sleep during the work week though. Per Mistress Amber’s assignment, I am to propose a punishment and then carry it out if I am naughty. The last time I tried to do this in my Modified Wedding Punishment it was a disaster for me as I thought I could accomplish a lot and impress Mistress Amber, but to no avail. Thankfully she took pity on me and made my punishment less severe. This time I think I will propose punishments more in line with my abilities to accomplish them, I Hope.

The only portion of the activity that I failed to obey was the cuffs and only at night. sissy billy would like to propose the following punishment scenarios.

In the case where sissy billy does not wear cuffs so she can sleep during the work week, this should be a lesser punishment as she does need to work and get some sleep and so is only a naughty sissy.

Since sissy billy needs her sleep, she can remove her cuffs before bed. However, to reinforce that she is still a sissy, on the nights she does not wear her cuffs, she will no longer be treated like a sissy, but like a sissy baby. Baby’s do not take showers in the morning, but sissy baby’s take baths and so sissy billy will take a bath and a sissy when taking a bath should always take a bubble bath. Tomorrow sissy billy will start taking bubble baths each morning she does not wear her cuffs. Additionally, since sissy billy is still trying to learn to wear her sissy clitty cage, she will be required to wear it whenever she is wearing her cuffs. sissy billy will owe four additional bubble bath mornings when this assignment is completed.

The second part is for a very naughty sissy. Since this activity may go on for quite some time, I will offer some options for myself so as to vary the punishment. The following punishments are also punishments that sissy billy has had in the past and does not like. So by offering a variety, she may learn how to deal with her punishments.

On non Work Week nights like last night when sissy billy did not need her sleep and did it for her convience, the following punishments will be carried out the next day before she goes to sleep. There are six punishments and only one will be awarded to her when she is a very naughty sissy. sissy billy will take a single dice, roll it and whatever number appears will perform that punishment. Listed below are the punishments listed 1 thru 6

  1. sissy billy is to wear High Heels, a water balloon stuffed big bra, cuffs, sissy clitty cage, and a thong and stand in a corner for 10 minutes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  2. sissy billy will stuff a bar of wet Pink Camay soap into her mouth, put clothespins on her nipples, High Heels, cuffs, sissy clitty cage, and a thong and stand in front of the mirror for 5 minutes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  3. sissy billy is to make a bedtime snack of Level 1 and 2 baby cereal, vegetable, fruit and while wearing cuffs, sissy clitty cage, Stuffed bra and a thong eat the whole snack. After she has finish the baby snack she may take off her sissy items and climb into bed with a 4 oz bottle of baby formula and drink it. The sour taste of baby formula all night should remind her of being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  4. sissy billy is to put a bar of Pink Camay soap into water for 5 minutes so it is wet, soapy and gushy, get ready for bed by removing her sissy items and shove the Pink Camay into her mouth for 1 minute (enough time for the gooey soap to fill her mouth). She is then to take the bar of Pink Camay soap out, but is not allowed to spit any of the gooey soap in her mouth out, but must keep it in her mouth for another minute, get into bed and then she is to swallow it. The soap taste will remind her to think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  5. sissy billy is to put on High Heels, a water balloon stuffed big bra, cuffs, sissy clitty cage, and a stuffed diaper and rubber diaper cover, her teal Jumper to package it all and then using the treadmill in the basement walk for 1 mile waddling like Mistress Amber likes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  6. This is a Mistress Amber lucky – out of the goodness of her heart – get out of punishment card. There is no punishment, but sissy billy will kneel by the bed for 5 minutes before going to bed and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night. sissy billy gets to roll again and double the length of the punishment she gets on that roll. once completed, sissy billy will go to bed with all of her cuffs locked on anyway.

For last nights indiscretion sissy billy rolled the dice and the number two came up. I performed the punishment and will document it to Mistress Amber.

Of Course Mistress Amber has the option of modifying or changing any of the punishments above as well as deciding the length of this assignment. The next non work day is Saturday and so the very naughty sissy scenario will be decided after Friday night. Hopefully I do better this Friday Night.

Updated by Mistress Amber on May 28, 2009

The Actual Wedding Punishment – Sunday Night

It is Sunday Night and I have taken off my Sissy Maid Outfit.

Mistress Amber – I am sorry, but I must give up. I can not do this. I am so tired that I can not continue. I am sending this as a confession and an admission that I have failed to complete this assignment. I will send the rest of the photos tomorrow.

I apologize to all the other sissies as being a poor example of what a good sissy should be.

When I was young my mother would tell me that my eyes were always bigger then my stomach and I would always order more then I could eat.

Well, that is just what I did when I submitted this punishment to Mistress Amber as something I could accomplish. Mistress Amber even made it less severe and I still could not accomplish it. I am a poor excuse of what a good sissy should be.

I apologize Mistress Amber

sissy billy

The Actual Wedding Punishment – Saturday Night

I am home from my humiliating trip to the mall. It was a disaster as related in the previous post. It is now Saturday night and I am tired and humiliated and know I am already failing my overall assignment. I will continue in an effort to improve. I am back in my diaper and my collar, ankle/wrist locks and I am nothing more then a sissy baby. I did have to change my diaper before getting back into my sissy baby wear. The good part of milking my sissy clitty is getting harder. I am not as young as I use to be and it took a long time to milk into my diaper. This is embarrassing as every other thing I have to do. I am crawling around like a little baby. I am trying to start my posts, but am making little progress. I have put the baby food low enough so that I could reach it and I have made myself a sissy baby meal. I am hungry, but this does not look good. Let me just say, that I now know why a baby spits out its baby food when you feed it to her. It tastes horrible and even though I was really hungry and did manage to shove it all down my throat, I could have thrown up several times. If I was allowed to fast, I would not be eating. The baby formula was also terrible. I did manage to water it down so I could at least get it down my throat.
I am so tired that I will be going to bed early, although I do not imagine that I will sleep well or much.
Good Night Mistress Amber, I will see you in the morning.

The Actual Wedding Punishment – Letter of Apology

I finally got home (It was a long drive and my hangover still had not got any better – even with anacin) and started my next punishment. I am to write a letter of apology to Mistress Amber for being a naughty sissy unable to follow simple instructions and for causing her a lot of extra work. I went to my bedroom and took off all of my clothes and first had to change my diaper. I had managed to wet it on the drive home. With the penis plug in my mouth, I performed one of the pleasant duties of this punishment and milked my sissy clitty into a new diaper. I then put on my 4XL rubber diaper cover, a big bra stuffed with ballons on the verge of exploding just like Mistress Amber has said she so likes in many of the comments made to this site and my new teal jumper to package it all together. I then put on my collar, ankle and wrist cuffs locked together and with a penis plug in my mouth crawled to my desk to write my letter to Mistress Amber. I was not allowed to stand, but with the ankle and wrist cuffs locked together, all I could do was crawl like a sissy baby should. I climbed into my desk chair and began to write my apology.
This was not a quick letter as I was to first compose a draft and then rewrite it in good handwriting so everyone could read it. It was also very difficult, because with my wrists locked together, I had to constantly pick both up and re-position them on the paper so I could write neatly.
Mistress Amber does think of little things to add to each punishment. The penis gag in my mouth was gagging me and I almost threw up several times with my upset stomach. I wanted to write fast, but had to slow down so the letter could be readable. Below is me locked and gagged in my sissy baby diapering and also attached is my letter to Mistress Amber which I sincerely mean. I hope she can forgive me for all the additional work and effort I have caused her. If only I could be a better sissy.

Farewell to Arms

If you have problems with your sissy putting her hands right in front of the paddle and don’t want to bother with hold them away yourself, you can try this little trick: take an extra pair of ankle cuffs and put on on each arm, just above the elbow. Clip each wrist to the opposite elbow, and she won’t try to block anything. She won’t even be able to push herself up off the couch you bent her over.

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