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.

What she thought was going to be easy was quickly turned around. Mistress Rosemarie drove off and explained to sissy billy as she drove that she was going to teach sissy billy social interaction.

They drove for several minutes and then pulled into the driveway of a house that sissy billy did not know. Mistress Rosemarie stopped the car and told sissy billy it was time for her to meet some of Mistress Rosemarie’s friends from high school. sissy billy turned red as Mistress Rosemarie unbuckled her seat belt and literally dragged her to the door. She knocked on the door, opened it and dragged her inside. “These are two of my friends, sissy billy. Say hello to Lynn and Donna”. “Hello Lynn and Donna” sissy billy stammered. She was immediately corrected and told to call them Mistress Lynn and Mistress Donna which she did with great humiliation. They both laughed out loud and then Mistress Rosemarie ordered sissy billy to tell them exactly why she was now a sissy. Thus began sissy billy’s social humiliation. She was made to serve them as they laughed and giggled as Mistress Rosemarie talked with her friends. Mistress Rosemarie was obviously not going to be kind to sissy billy. The remainder of sissy billy’s three days with Mistress Rosemarie was equally as humiliating as Mistress Rosemarie kept her constantly in humiliating social situations and lectured her on what was to come and the social practices she should expect. There was also a shopping trip and a pajama party on Saturday night which was very exciting. For Mistress Rosemarie, that is – not sissy billy. At the end of the three days, sissy billy stood at feminine attention in the living and waited for a knock on the door and her next training Mistress to arrive.

When the knock came, sissy billy trembled and answered the door. Mistress Jacqueline stood at the door. In a blink of the eye, Mistress Jacqueline grabbed her hand, pulled her out the door and into the yard for even more neighbors to see her. Once again she was seated belted in the back seat and Mistress Jacqueline said in a loud voice: “That’s a good little sissy – sissy billy”. She could hear the neighbors laugh. Mistress Jacqueline said: “sissy billy – it is important to learn the basics first and I am here to teach you the punishments a cross-dressing sissy should expect”. The next three days were consumed mostly with various methods of spanking. sissy billy cried often and long as Mistress Jacqueline administered spankings with several types of paddles, a horse whip, several birch rods and a bamboo cane. Finally she stood crying in the living room waiting for her next Mistress. She thought nothing could be worst, but she was to soon learn that a sore ass is not the worst thing that can happen to a sissy.

The knock finally came and she opened the door and there stood Mistress Jane.

sissy billy quietly walked to the car and very gingerly sat on the seat and cried as Mistress Jane buckled up her seat belt. It was now Friday afternoon and Mistress Jane told her to relax as they had a long three hour drive to a small town in the mountains and her weekend would be spent at Sunday School. Mistress Jane explained that she would take care of her sissy training and sissy service training. That did not sound so bad and sissy billy tried to relax as best she could. Every time she moved, however, she broke into tears once again from a very sore ass. Mistress Jane ignored her.

REVELATION: People are often very different from what they appear to be.

After an hour of driving sissy billy got up enough courage to ask Mistress Jane where they were going. Mistress Jane had always been the quieter and kinder sister whenever sissy billy had gone home with Mistress Marilyn and she thought that Mistress Jane would have a little pity and not be so severe. What Mistress Jane said shocked and terrified sissy billy.

Mistress Jane said: “Do you remember yesterday when you signed up for Sunday School? Well you are going to a school. It is not a Sunday School though, but church will be involved on Sunday. I am the Head Mistress of “The Sissy Training and Punishment School” dedicated to the correction of Cross-Dressing Sissies and their Punishments for such vulgar habits and the Punishment of insolent and Non-Obedient Husbands that need to learn to respect their Wives and the Absolute Obedience of both for all Women. You have been enrolled in the beginner’s Class of disgusting Cross-Dressing Sissies and Disobedient Husbands. You will learn respect”.

sissy billy was shocked into silence and sat terrified and silent for the rest of the trip.

She had never imagined that Mistress Jane (quiet and shy Mistress Jane) was actually the Head Mistress of a Sissy School. They pulled up to the front door of what looked like a Mansion to sissy billy. Mistress Jane unbuckled her and led her into the House.


“I need to go freshen up, but let me introduce you to one of our other Mistress’s which will be assisting me in you weekend training. This is a 24/7 training weekend and it will take both of our sincere and loving efforts to begin your training. Mistress Amber, let me introduce you to our newest pupil”, Mistress Rosemarie said. Mistress Amber just smiled.

Mistress Jane then said: “Mistress Amber, please take sissy billy to the sissy babies room where all our beginning sissies start their training and live for the weekend”. Mistress Amber grabbed her arm and squeezed hard hurting her until she started to cry and led her to a great room. Mistress Amber seemed very strict, which frightened her even more.

As she was led to the room Mistress Amber told her that she would be allowed to protect her identity, although Mistress Amber said she thought that was to kind for a sissy. She would be given a mask and a Ladies scarf to wear, a feminine mask and a pretty scarf. Before we entered the room she was given the mask and told to put it on. She was also told to take off her Negligee, to leave her thong on and to keep on the cuffs and high heels. She was then led into the room. Against one long wall there were 6 small single beds made for little girls and made up with a feminine flowery blanket and separated by curtains and six stools in a circle facing each other. Three other naked male sissies were already sitting upright on the stools. She was told to sit quietly and wait. The sissies stared at each other, but no one talked. Eventually two other sissies were led into the room and sat down. Each sat quietly and did not speak.


Mistress Jane finally entered the room and in a stern forceful voice told the six men that they were now enrolled in her sissy school by their Mistresses and were now under the care and training of her and the other Mistresses. There was to be no backtalk, instant obedience would be expected and there would be stern punishment. They were told that they would sleep in this baby’s room together and maybe if they were good, they would be graduated to the normal double occupancy sissy bedrooms on Monday. They were ordered to stand up and go to their cubicles where each Mistress (each sissy had a Mistress – sissy billy’s Mistress was Mistress Amber). Mistress Amber then told her to strip off her negligee, thong, cuffs and heels and was given a diaper and rubber cover and sissy baby’s romper sleep nightgown and pink feminine low heel slippers to put on. She was then told to bend over her little sissy bed as were all the other sissies.

Mistress Jane then told the Mistresses to each pull down their sissy’s diaper and nightgown panties and administer a stern spanking to each sissy to get their attention. Mistress Amber looked at sissy billy’s already red and obviously hurting ass and smiled. She thought about how easy this was going to be. With a strong smack of the paddle, sissy billy immediately yelped and started crying. The other Mistresses also started, but their sissies did not start crying until the 10th or 12th spank. Mistress Amber smiled as she knew she had a sissiest sissy and spanked sissy billy 30 or 40 times and then stopped knowing sissy billy knew she was the Mistress. sissy billy tried to stay very still, afraid to move, but crying hysterically. At the same time the other Mistresses also stopped and the room echoed with the crying of 6 sissies.

[![](http://cdpunishment.com/institute/images/2009/08/sissybilly_090808-004e.JPG )](http://cdpunishment.com/institute/images/2009/08/sissybilly_090808-004s.jpg )

Finally they were led to the center of the room again as the Mistresses then sat in comfortable chairs with their sissy kneeling before them and began to feed each sissy her sissy baby dinner. Dinner consisted of a huge bowl of mushy gushy sissy baby food and several bottles of baby formula. There was much whining by the sissies as the baby food was spoon shoveled into their mouths. Finally the Mistresses stopped the forced feeding when it was obvious that each sissy had a completely stuffed tummy. Each sissy then had to drink one last bottle of baby formula and there was much gagging as the last bit of formula topped off a stuffed tummy to the point of throw up. They were each then led to their little sissy beds and even though it was only 7:00 PM, they were told it was a sissy baby’s bedtime. Before they were allowed to climb into bed though, each was given four tablespoons of some heavy disgusting tasting medicine that they were told would help settle a sissy baby’s stomach. The medicine was actually castor oil which in reality would turn the baby food mushier and allow it to quickly move through each sissy’s body like diarrhea. The castor oil is a better laxative then an enema, but takes a few hours to work its way thru a sissy’s body. Each sissy was given 10 more spankings to remind them of their obedience and then they were tucked in to bed.

By 8:00 PM the castor oil was beginning to work and a side effect of it is cramping. All of the sissies were beginning to cry and complain and finally Mistress Jane came in and said:

“If you sissies are going to cry, I am going to give you something to cry about. I am going to send each Mistress in one at a time to help you”.

Well, Mistress Amber came in first and took sissy billy’s hand and dragged her to a punishment bench in the center of the room, made her bend over it and gave her 25 spankings. Needless to say, sissy billy was crying hysterically after 5 spankings and when Mistress Amber was satisfied she now had something to cry about, sissy billy was taken back to her bed. As soon as Mistress Amber left, another Mistress came in and did the same thing to her sissy. This went on till midnight and all the sissies were either crying or listening to someone else crying. No one slept for fear they would be next.


At midnight the Mistress all came in and each went to their sissy and told them they had better go to sleep or else. Each then told their sissy that they had something to help ease their cramping. Each sissy had her diaper and panties pulled down and each Mistress inserted 4 suppositories to help their sissy’s cramping. They were then told to go to sleep.

The suppositories where actually glycerin laxatives. By morning each sissy had totally and disgustingly wet and soiled her diaper. The smell in the sissy dormitory was incredibly bad.

It was morning, but each sissy dared not move and each was terrified of what was to happen to them next.

Let me tell you. It was not pretty and if the sissies knew what was to happen next, they all would have fainted from shock.

1 Comment

Got Something To Say:

Your email address will not be published. Required fields are marked *


WOW! Sissy Billy, did You faint yet or does it just keep getting better and better?

Copyright © 2024. Powered by WordPress & Romangie Theme.