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.

To prepare for the pretty Sorority Pledge that you see above, I first took a scented bubble bath with lots of bubbles. I then powdered myself with a scented dusting powder, applied red nail polish and then began to put on the appropriate lingerie. I first put on my pink panties to match my dress and a bra with adequate, but dainty medium sized breast forms. Then my corset which I laced up as tight as I could to give me a girlish figure to the point that I could only take little breaths. A proper lady always wears a slip under her dress and I picked out a pretty pink one. The added a pink crinoline to add a feminine full look to my dress.

I was now prepared to go off to my Sorority training and initiation, for better or for worse. One last picture before I start. You must take notice of the beautiful corsage Mistress Rosemarie gave me and loaned me a pretty purse. Every girl must have a corsage when she goes to the prom or in this case a Sorority training session.

My first session was called “Dressed for Dinner” and I had four choices.

1 – I was to wait outside in public view until the Sorority Sisters allowed me in. I declined to accept this challenge and went into the hall throught the back door.

2 – Mush Mouth – A lovely dinner of jars of baby food and large pitchers of formula. I have in the past had to eat baby food and thought that this would not be to hard. I accepted this challenge. My favorite meal is a steak (16oz), mashed potatoes (4oz), no vegetable (Ugh) and a salad (4oz). I felt this would be acceptable and also a quart of formula. I had never really had to drink baby formula. I purchased these at the store and set the table for a lovely dinner.

I completed this test successfully.

3 – Happiness Pie – For desert we would have a whipped cream pie eating contest, but no hands allowed. I like whipped cream, so this would be easy. I also chose this challenge. It was messy, but it did taste good. This was and easy Sorority Training Activity. I can’t believe they actually assigned us something easy.

I have successfully completed this Sorority activity.

4 – A Happy Ending – I have decided not to attempt this activity.

Our next session is what the Sorority Sisters call “Early Punishments” as they laugh and giggle at our nervousness.
We have cuffs and collars added to our pretty dresses and a selection of punishments occurs while still at the banquet hall.

1 – We are to be each locked in a dog kennel while the rest of the punishments are prepared. I do not have a dog kennel, but I try to improvise by using a packing box.

I thought I did a good job of improvising and would hope that the Judges agree and offer partial credit.

2 – For general principle each Sorority Pledge was then give a good paddling.

I paddled myself many many times and feel that I have successfully completed this Sorority task.

3 – Oral Practice I – Next, each gets to choose from a selection of dildos to practice their oral technique on.

I attached a dildoe to a stand, kissed it and began practicing my oral technique.

I sucked and licked and kissed the dildoe for a long time until my throat and lips hurt. The dildoe was sufficiently caressed. I completed my Oral technique practice.

4 – Oral Practice II – there was no sister to pick me and therefore I did not perform this exercise.

5 – Cleaning Up – I was quite messy and the Sisters stuffed a wet juicy bar of pink Camay Soap into my mouth to clean up the mess.

The pink Camay soap was soft and gooey and did not taste very good, but my mouth was clean.

Late Punishments – We were taken back to the Sorority House and told we could remove are pretty fancy Dresses. We then were handed a t-shirt and shorts. First, however, we were given a very large very big super big bra and told to stuff it with the biggest forms we could make. We were then started on our next set of Sorority Treatments. We of course still had to keep on our collars and cuffs.

1 – Exercise Time – Since we had all supposedly eaten so much mush food, we were to exercise and wear off all those girly pounds. I have problems with my ankles and knees, so I choose the Tread Mill, sit-ups and push-ups.

2 – Private Paddling – I had thought we had been good Sorority Pledges/Bitches. But the Sisters thought otherwise and decided a really good spanking was needed to make us cry. Hoods and gags were also brought out in case we could not tolerate our punishments.

I could not stop myself from crying with anticipation of my spanking. Because of my lack of control, the Sisters stuffed a penis gag in my mouth. They then instructed me to begin to spank myself and I did for what seemed like forever. Finally my arm got so tired I had to stop. My hiney hurt very much, so I guess I successfully completed my punishment.

3 – Shower Time I – I was then sent to the Ladies room to give myself a Bikini shave.

It is hard for me to see my crotch, but I believe I have shaved myself as directed. This task is successfully completed.

4 – Shower Time II – I was now directed to give myself a complete leg wax until my legs were smooth and clean. I had purchased a leg wax kit, but I had never done this before. I proceeded as directed.

I proceeded as directed on the box. I pulled the strip off and immediately let out a cry. I pulled the other strip off and tears came to my eyes. It really hurt and I don’t have a lot of hair on my legs. I do not know how a women can tolerate to have her hair removed by waxing. They must really cry a lot.

I stopped this task after two wax strips and admit that I have failed in this task.

5 – Shower Time III – Sisters then talked among themselves and could not agree if my mouth was sufficiently clean. So to ensure my mouth was clean, I was to again practice my oral technique, this time on a wet bar of soap lubricated with dish washing soap. I cringed at the thought of how terrible this would be, but I had to try.

Bedtime – Finally and end to this Sorority Pledge Night. The last assignment was to pick how we would sleep. It was recommended that I pick one of the hard assignments, but that entailed all sorts of bondage and I knew that I would not last the night and fail the test anyway. I tried to be creative and pick an easy task of wearing panties and a nightgown for 5 consecutive nights. I had never been successful in doing this, but this was my best chance. I then thought if I coupled this with a medium hard task of wearing a diaper for an entire 3 consecutive nights that it would equal a hard task. I started.

Night One

I was dressed in my nightgown and I went to bed. I was so tired from all my Sorority activities that I thought I would fall to sleep instantly. I have such trouble sleeping in the negligees that I love. It arouses me and my adrenaline starts flowing. Two hours later I was totally awake and with having to go to work, I needed sleep. I took off the Nightgown, panties and diaper. I concede that I get no points for the first night. I decided to complete the five night activity hoping that I would get partial credit.

Night Two – I put on my dark blue panties, pink Nightgown and diaper with pink cover again.

I went to sleep and while I did not sleep soundly, I was doing well till about 3 in the morning. My stomach had been nervous and upset and all of sudden I had diarrhea and urinated in my diaper. By the rules I could not change it till morning and after an hour it was so disgusting I was going to throw up. I had to get up and take it off and shower.

I concede again that I get no points for Night two.

Night Three – I decide that I will not try the diaper again and will try only for partial points for wearing a nightgown. I put on my long pink nightie from Sunday which I had washed along with blue panties.

I suceeded. I wore my negligee all night long and finally completed a portion of this task.

Night 4 Tonight I would wear my lavender shorty nightie, tourquise shear top and white lacy panties. I hope I can wear them all night again.

I did it again. I am so happy and pleased. I feel I really accomplished something. Now for the end of this Sorority Training assignment.

Night Five – I chose a new and very pretty peignoir set for extra luck. It is a lavender long negligee with a lavender sheer overlay. I wore tourquoise panties to match. I hope they match. I really do not know how to match colors.

I feel very pretty in the negligee. I hope it brings me luck and I succeed again in sleeping in my negligee. It is morning after the 5th Night and I have worn my negligee all night again. I am so excited and since it is so difficult for me, I have had a major success.

While I have not totally been a success with this Bedtime activity, I hope the Judges will consider partial credit for me.

This was a really difficult Sorority pledge night and days. I tried really hard to be the best pledge I could and I think I succeeded in almost everything I attempted. I only gave up on a few tasks and hope that I get partial credit on the other Pledge activities I chose that I wasn’t totally successful with.

Thanks Goodness this is finally over. It was as difficult writing about it and doing it.

I hope the Judges are considerate and that I receive a passing mark.

Thank You – sissy billy


Got Something To Say:

Your email address will not be published.


Mistress Katzenburg, I so enjoyed myself on Sunday and these last few days. Once again I applaud you. Your assignment was extraordinary. In one of your comments to sissy billy you told her that you would consult me and if I was dissatisfied, it would mean automatic failure for her. I have read sissy billy’s post and I could not wait for your request of comments and my enthusiasm to “Tell All” has overcome me. I am sorry. I just had to add my analysis after reading her post.

I had stepped back and would not offer or request that certain assignments be performed and I will try not to offer an opinion of whether she has passed or failed the assignment. But that may be difficult. I will, however, offer a point of view from my observations. Sissy Billy, as anyone would, looks and judges things from her point of view. She does live in her own fantasy world. I would ask that the Judges make their own decisions as I do not want sissy billy to blame me for her failure. I would also admit that I am her most severe critic, so please take my statements of fact in that light.

In general, sissy billy tried very hard and did look very pretty in her dress and all her under lingerie and accessories.

Dress for Dinner.

I had wanted her to go outside and wait with the other Sorority pledges, but with her shyness for exposure she declined. There was no one around and she could have done this easily. Such a sissy. I did not make this a request though, just a suggestion.

Mush Mouth – Take a close look at the last Picture. The plate still has a lot of uneaten mush and almost a 1/3 of the pitcher of formula. She stopped at that point with a big Ugh and how terrible it tasted. She certainly could have eaten more.

Whipped Cream – too easy. I am sure pieclown did better with this.

Happy Ending – sissy billy, why didn’t you try this. You always liked the first part of this activity, don’t you like slurping and sucking. Any good sissy pledge would have picked this challenge. You never had any problems with me doing this a long long time ago before the tables were turned. Don’t like the opposite position. Are you to good to be a girl. Oh well, she didn’t pick this and I didn’t push her to.

Early Punishments:

Dog Kennel – get a bigger box next time sissy. She really didn’t spend a lot of time looking for one.

Paddling – 10 with the big paddle and 10 with the little paddle. I didn’t hear any crying or see any tears.

Oral Practice – what kind of dildo is that. I told her many times that she must go and boy a real big one at the adult store for practice. Worthless practice – only 5 minutes. Any girl worth her salt would have done 2 or 3 times that.

Oral Practice on a Sorority Sister. What – no volunteers. What about the fake vagina you have that you use to play with until I made you stop. You could have practiced on that.

Soap in the mouth. She has her mouth washed out fairly often and she could only do a few minutes of cleansing.

Late Punishments:

Exercise – You did not say how much you did. Judges – 5 minutes on the treadmill, 4 push-ups and 10 sit-ups.

Paddling – The gag was for her whining and then she gave herself less then 20 whacks. She is a sissy.

Bikini shave – sissy billy needs glasses to see.

Leg wax – It is a good thing you are not a girl. You even make a poor sissy. No tolerance for the pain a girl goes through.

Soap to practice oral technique. There was not sucking or slurping or oral technique. In less then 2-3 minutes she was gagging.


You are such a sissy, sissy billy. Pick an easy and a medium activity and can’t pass either the first two nights.Then you wear your nightie for three nights. Don’t know what you are so proud of.

Judges – please excuse my anger at her, she makes me so mad sometimes. Do not downgrade sissy billy to severely because of my statement of the facts. I am sure pieclown will be totally honest, but she may not have as severe a critic as I sometimes tend to be.

I wonder what is next for you, sissy billy. I think you may have a tough time getting a passing grade. If you were pledging my sorority you would undoubtedly fail and have to repeat the entire pledge course, but that is me and that is off the record.

Sorry sissy billy, but I must be honest for the sake of the assignment.

Mistress Rosemarie

Oh my Gosh. Oh my Gosh Mistress Rosemarie. That was so mean. This is so unfair. Everyone now will think that I did so bad. You make it sound like I failed every activity that I attempted.

I tried so hard and I think that I did really really good for a sissy. I tried to do more tasks then I was supposed to and I worked really hard at them and I did good on a big part of them. You are being so matter of fact and everyone will not think about my efforts.

Judges = Please think about how hard I work at being a good Sorority Bitch.

Please pass me, sissy billy

I see they sure don’t miss those mouthsoapings here. I know how yucky that pink Camay is when it’s all soft and gooey. Fascinating! Guess I’d try to keep my mouth shut most of the time. But wow, what a clean mouth ready for oral service to the girls. I’d be afraid to join that sorority. I’ve been known for sometime as the “Camay Kid” – bet they’d have fun with that nickname. Hazed with Camay…mmmmmm no thanks

Hello Sweetsuds,

Yes, It is disgusting. At least now I am only made to suffer with pink “Camay” mouth washings. When I first joined “The Institute” I was made to keep the icky “pink” in my mouth for an hour as I wrote out my assignments. I could not do it and would gag and have to spit it out. Then I would have to start again inserting the “pink” again. You can guess how long it took me to complete that assignment.

It is so much fun here at “The Institute”, but that is why my Mistress submitted my application and that is why it is call the “The Institute for Cross-Dressing Punishment”.

sissy billy

Copyright © 2022. Powered by WordPress & Romangie Theme.