Tag Archives: clitty-cage

Aissgnment # 2A – “sissy billy’s” Ovulation Time

I am a Sissy that is now having her monthly “Period” at a regular Interval. Mistress tells me that it is part of a feminine cycle that I now “Ovulate” each month. I did not really know what this meant and was sent to research it’s meaning by Mistress.

A Women’s Ovulation time is the 2-3 Days each month when she is fertile. It usually falls in the middle of her Menstrual Period which I have now been experiencing. It is also the time of the month when the egg falls and she can become pregnant. Her hormones are at their peak and she feels her most feminine. It is also the time of the month when she will unconsciously dress her prettiest and have her strongest feelings to get pregnant.

At this time of my sissy life I certainly do not want to get “pregnant” or get anyone else “pregnant” and Mistress is “helping” me with contraceptive protection.

As a result of obsession with Cross-Dressing and the Training and Punishments the “Institute” has assignment to me, another phase of my Sissy Life begins.

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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.

4. 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’s Ovulation Time

Now that you are a young “sissy” Lady and are getting your monthly “Periods”, there is also a time of the month where you “Ovulate”. This is usually about two weeks after your “Period” starts each month and after consulting “Auntie Flo” and her menstrual Calendar, it is determined that you will be Ovulating from next Wednesday thru Friday.

This assignment (Let’s call it Assignment 2 A) is in addition to your Assignment # 4 – More Soap Testing which will be issued this weekend and start on Monday.

Assignment # 2 A – sissy billy’ “Ovulation”.

This is a time when a Lady is most susceptible to getting pregnant. We do not want that to happen to you or for you to impregnate anyone else. So your assignment is as follows.

* You are to research and write a paragraph describing a Ladies Ovulating Time.
* When at home (I think you are safe when out in public) you should wear protection. You are to put your sissy clitty cage on and wear it whenever you are home.
* A Lady usually feels sexy and pretty during this time. You should change as soon as you get home into a pretty feminine outfit and then before bed put on a pretty Negligee and wear it until morning. You should wear something different and pretty each night.
* Each night you may (since this is safe and no impregnating can take place) practice your oral technique on your dildo and your vagina.
* After three nights and your “Ovulation” has ended – you are to remove you sissy clitty cage, put on a condom and relieve three nights of pent-up sexual frustration filling it as much as you can. You are then to snip the end and in front of your Mistress such your juices till it is empty.

This should protect your “sissy” virginity.

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 – 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 – 2 “A Pajama Party”

From the time I was young I always wanted to go the Girl’s Pajama Parties. They always seemed like they would be a lot of fun. I would hear my older Sister talk about the Pajama Parties she went to and how all the girls would wear pretty, frilly, lacy sexy Baby Doll Negligees. When my Sister had her Pajama Party I peaked and when I saw all her girl friends wearing those feminine Baby Dolls, I wished from that day to this that I would be invited to one. It never happened, since Pajama Parties were only things that girls did. I was so Jealous.

Naturally, when I had the opportunity to travel to Fantasy Island one of my first wishes was to attend a Girl’s Pajama Party. I was soon to regret my wish.

Mistress bought me a very feminine frilly red Baby Doll Negligee and frilly lace Panties. I got very excited about going to my first Girlie Negligee Party.

Until …………..

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A sissy must be prompt in her assignments – Morning 3

It is Sunday Morning and I have been very busy, but still have not completed my profile. So I am once again completely dressed in the sissy girlie outfit of Mistress Rosemarie’s choosing.

I have rephrased and corrected sections of my profile and added another section. I was certainly hoping to have completed this by now, but I have one question that I must ask Mistress Amber because I am not sure how to do a link. After several months of trying to be a good sissy client you would think that I would know all of these things by now, but I do not. I quess I am still in need of more and extensive training and punishment as a sissy client.

I will, hopefully, finish my profile as soon as Mistress Amber helps me with my question.

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A sissy must be prompt in her assignments – Night Two

It is Thursday night and I am back fully dressed as a pretty sissy. This is definitely not pleasant being dressed as a sissy all evening. Not only I am making dinner for Mistress Rosemarie, but she is making me go to the Ladies Room often during the evening to fix myself – you know – fix my makeup and lipstick and fluff and straighten my skirt and blouse. It certainly is difficult being a girl and looking you best.

I have found and collected training photos and have uploaded them to my profile page. I hope to complete some miscellaneous items of my profile on Saturday and can finally go back to my normal dressing life. I hope

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A sissy must be prompt in her assignments

I was recently, well actually a month ago, assigned a task by Mistress Amber to fill out a profile set up by her and to complete it as soon as possible. Well, I got busy with other assignments and finally pushed Mistress Amber’s patience to the limit. A sissy never has the excuse of being to busy to fulfill her Mistress’s instructions.

Mistress Amber was still very understanding, which I do appreciate greatly, and did not punish as severely as I deserved. I have been directed by her to dress up completely in feminine clothing every night until I completed this task. I further disappointed Mistress Amber by not starting my task immediately last night and now I am also to wear my sissy clitty cage.

Mistress Rosemarie is delighted with this because she had warned me to get going on my assignment and she so likes me to look pretty. She now forces me to dress as soon as I get home and to stay dressed all night. I make and feed her dinner, clean up and then go to the computer. Mistress Rosemarie tells me to take my time now because she wants me to dress like this every night, but I know I must complete and please Mistress Amber by finishing my Profile.

Mistress Rosemarie laid out a pretty feminine outfit and took pictures for all to see and delighting in my humiliation.


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sissy billy’s Willful Insolence

[sissy billy][] was right when she said “[I must learn to keep my mouth shut][1]”. After reading her new standing rules she wrote “I am currently dressed and am on my way to work and already late, but I will shave my legs over the weekend in preparation for wearing my pantyhose on Monday.” Umm, yeah. Rules can take effect whenever she wants them to.

Well how about this instead: when she gets home from work tonight, instead of shaving her legs in preparation for Monday, she will shave from her neck down. Once nice and smooth, she will lock on her sissy clitty prison. It can come off on Monday, when she is ready to return to work.

Is that better? Or do I need to be clearer?

[sissy billy]: http://institute.cdpunishment.com/profiles/sissy-billy/
[1]: http://institute.cdpunishment.com/2009/11/new_standing_rule_for_sissy_billy#comment-6286

sissy billy Freed from Chastity?

Back when Mistress Amber was in charge of sissy billy’s training, she put him in state of sexual deprivation (which was sometimes enforced by locking up his sissy-clitty). Now that I am in charge of her training, I have decided to lift this restriction. sissy billy will have free access to make love to her sissy clitty if she:

* Wears panties full time
* Wears pantyhose under her suit when she dresses for work
* Keeps a relief diary where she writes down all of the fantasies she has while making love

To make it fairer for sissy billy, I will even give the opportunity to choose her option on a month-by-month basis, starting with November. She can either have unfettered access till the end of the month, or will spend it chaste, locked inside a sissy clitty prison. The choice is hers.


I have been given an assignment by Mistress Amber to discuss Chastity. This is a new condition for me in the past few months and I am learning to understand and deal with. I have not found it easy or pleasant, but I shall relate my experiences to-date. I would be interested in how others have dealt with it and what they feel about Chastity.

To better understand a topic, go back to its origins and history. The concept of Chastity and in particular the use of Chastity belts go back about five centuries. The reason for Chastity as a practice was to temperate sexual behavior of legitimately married spouses or sexual continence of the unmarried child. Since men in the dark ages held the absolute power (except for maybe a Queen – imagine having a Queen as a Mistress. Punishments were severe in those days), this was directed almost solely at women and girl children. I am sure it was reversed at times, though there is little mention of this. An early chastity belt did not look pleasant and if your Master went off to a pilgrimage it could be months.

A Chastity belt was a lockable device fitted over the vagina of a female to ensure fidelity of a wife or guard the chastity of a daughter.

In today’s world a Chastity belt is considered a sex toy. I guess it depends on ones perspective or situation. If you are the Mistress or the Master, it can be fun to have the power of complete dominance and control. If you are the subservient, you may not agree.

This is a sample of today’s chastity belt for a female slave. Girls, does this look like fun or not.

I certainly would not like to be female and be placed in Chastity by my Master. This can not be pleasant to have a plug in her rectum and a plug in her vagina. It must be uncomfortable to walk or move around, but on the other perhaps the vaginal plug may produce an orgasm or two in moving around. Any of you female slaves might be able to give a better opinion on this. While these may be called sex toys in today’s world, they really are a means of dominance and control for an obedient subservient sissy or slave. The sole purpose of a chastity as in old times is to temperate sexual behaviour and to maintain the sexual continence of a Master or Mistress’s subservient sissy or slave.

For you male sissies, the purpose is no different or less terrifying or less controlling. This is a picture of the sissy clitty cage Mistress Rosemarie purchased for my training and obedience.

I had started my application for training as a client in “The Institute for Cross-Dressing Punishment” when on my doorstep was a package ordered by Mistress Rosemarie and strongly suggested by Mistress Amber for my training enforcement. I had heard about a chastity restraint, but had never seen one. It looked terrifying to me. That night I was instructed to model it, take pictures and send to Mistress Amber for approval. I did not know how to use it and it hurt in putting it on. It was confining and pinched everything that was my sissy clitty. Mistress Rosemarie made me wear it the first night. I was afraid even to pee.

The fact that I was to wear this contraption as a training device that took control of my sissy clitty totally away from me was humiliating. I have read back through my responses to Mistress Amber and I am embarrassed by them. If I had only accepted the lost of control of my sissy clitty and accepted that this control belonged to my Mistresses I would have avoided a great amount of punishment training. My whining about how bad it was (it was and still is) just made matters worst.

I had to wear it to work. I was so afraid that some one would know that I was wearing it. Every time someone looked at me I felt humiliated as if they knew and were laughing at me. It also hurt to move around in. Mistress Amber’s comment did not help. I was told that sissies sometime had to wear their sissy clitty cage for months at a time. That did not make me happy. I wore it to work, I wore it at night and did not sleep, I wore it every time I had a desire to wear a pretty negligee and I wore it every time it fit a punishment that Mistress Amber devised. It did help me in curing my desire to touch myself. Good for Mistress, bad for sissy billy.

I complained about how it pulled my pubic hair. Mistress Amber helped me solve that problem. I shaved my sissy clitty. This was the first time I ever had to do this and it was humiliating. It did stop the pubic hair pulling.

Dealing with the mental side of my sissy clitty cage was by far the most difficult. It felt like old fashion armour hanging from my sissy clitty. In reality it was very light, but I could feel the weight between my legs. I was always self conscious when wearing it in public. It was well hidden by my pants, but I imagined a huge bulge that hung there for all to see.. I was constantly afraid of being discovered. I felt it always and each time I felt it my subservience was the first thing I thought of. It was humiliating. It did cure me somewhat of scratching my balls. Difficult to due with it on. Mistress Amber delights in referring to this as my battle of the bulge.

It has now been three months of training in how to wear my sissy clitty cage. I do better in putting it on and wearing it for extended periods of time. At the start of my last assignment I wore it for three days straight both at work and home and in public. I took it off and accepted part two A of my latest assignment for reasons other then the cage.

After three months the physical side of subservience and confinement in my sissy clitty cage is bearable. The mental side has not changed. It is still uncomfortable and clunky and wakes me up at night when I turn over and pulls my pubic hair, but the most difficult mental part of this, though, is that I have no control over my sissy clitty and I am constantly reminded of this humiliating aspect. Control belongs to my Mistresses and is always there as a containing punishment for when I am naughty. I still have a long way to go in mentally accepting this.

I accept that I need help and would appreciate others suggestions and comments on how to do better in wearing my sissy clitty cage.

sissy billy

sissy billy’s Standing Training Rules – Punishment Completed, I Hope – 2009-June-04

How I hope I have pleased Mistress Amber

On 5/18/09 Mistress Amber established Standing Training Rules for sissy billy. I was unable to obey these simple sissy training rules and was punished in various ways proposed by me as a training exercise and modified and approved by Mistress Amber. I have endured these punishments since that time as the sissy I am should. This past Saturday I was able to complete the non work week assignment and since Monday have also obeyed and followed the work week assignments.


As a sissy I should not brag about completing a simple assignment which any sissy should accomplish easily. As a new sissy in training I have had great difficulty with this. I proudly write that I have nothing to confess and I have accomplished the non work week and work week assignments.


For a work week assignment not followed. 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. Each Day sissy billy will take a bubble bath each morning she does not wear her cuffs the night before. 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.

Completed Punishment:

Since Monday I have obeyed the assignments and therefore did not incur additional punishments. I did, however, owe three days of punishments for days that I did not follow the punishment assignment at the beginning of the training. Therefore, each morning before I went to work this week I did not take a shower. I filled the bath tub for a sissy bath and put lots of bubble bath in it so there were lots of bubbles. I then took a bubble bath like a sissy baby. When I was done I patted my self off with a fluffy towel like a sissy would do. I was also wearing my sissy clitty cage whenever I was in the house and I had my cuffs on. This was typical of what I have done each day to complete my assignment.

Of course this punishment is not complete unless Mistress Amber concurs and tells me that it is.

I hope she does since I really will sleep better without my sissy clitty cage on and I am so looking forward to a shower like a normal adult again.

I, of course, am still bound by the rules as originally stated in my Standing Training Rules and will wear cuffs when I am in the house (I am doing so as I write this post) and will abide by the dress rules.

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sissy billy’s Standing Training Rules – Back to being Punished – 2009-June-01

How I have disappointed Mistress Amber

Well I am sorry to say that after a single night of success, I am back where I started. It was Sunday Night and I had all intention of wearing my cuffs and sissy clitty cage, but after an hour of laying in bed and thinking too much about my obedience and servitude trying to please Mistress Amber two nights in a row, I broke down and took off my cuffs so that I could go to sleep. I again have a busy week at work, but that is no excuse to disobey Mistress Amber. A sissy should be able to follow and complete simple assignments and again I am not up to my punishment.

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. Each Day sissy billy will take a bubble bath each morning she does not wear her cuffs the night before. 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.

Completed Punishment:
Each morning before I go to work I do not take a shower. I fill the bath tub for a sissy bath and put lots of bubble bath in it so there is lots of bubbles. I then take a bubble like a sissy baby. When I am done I pat my self off with a fluffy towel like a sissy would do. I am also wearing my sissy clitty cage whenever I am in the house and I have my cuffs on. This is typical of what I have done each day when I have not worn my cuffs to sleep and that has been every night during this work week.

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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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