Jean Part 6

Valerie 

Part 6

Norma began laying out her ideas for the school. She explained that the students were prisoners and each had signed an early release document. This document witnessed and notarized spelled out the conditions of the program. The prisoners would remain in custody until such time as they were deemed ready to return to society. The determination would be reached solely by the school’s head-mistress at her secretion. They would be subject to rigorous training, both physical and mental. They would also undergo severe dietary changes. They also had to agree to strict obedience at all times. Any infractions would return them to the regular prison with any time spent at the school added back onto their sentence. In essence the prisoners were the property of the school and the school could do whatever they wanted with them.
Norma described the process to us in great detail. Antoinette and I were to remain in our female attire at all times. We were to dress as provocatively as possible without being obvious. Gerda was in charge of the work outs and the dietary plans which included the hormone supplements.
We were all assembled at the front door when the panel truck arrived from the prison. The passenger guard got out of the front passenger seat with his nine millimeter drawn and stood about ten feet behind the truck. The over-weight driver came around to the rear and opened one of the doors. Norma handed his six hoods. He passed the six black hoods to the prisoners telling then to put them over their heads and secure the draw string around their necks. Once that was accomplished, he unlocked a pole and slid it out the rear of the van. He told the three prisoners to stand and get out of the van and form a line. Each one carefully exited the van due to the shackles on their wrists and ankles, and formed a line. The driver repeated the process for the three prisoners on the left side of the van. The driver placed each prisoner’s right hand on the shoulder of the prisoner in front of them. Then the driver led them into the school. The two body builder employees took over from there and brought the prisoners down to their cells. Norma signed the required paperwork and the two prison employees left.
Norma, Antoinette, Gerda and I went down to look over the prisoners. The body builder had each one in separate cells. The hoods were retrieved from the prisoners and most were pacing their cells except one who was sitting on his bunk. Norma offered a short welcome speech to them warning about strict obedience. All six were paying little attention to Norma because they were mesmerized by Antoinette’s and my outfits.  They could not believe their own eyes. They were staring at two beautiful women wearing extremely short skirts and low cut blouses. Norma got their attention back and ordered all of them to completely strip. She claimed that she did not want any bugs from the prison to be brought into the school. Reluctantly but obediently they all striped down and stood in front of the four women and the two guards. Norma pointed to the shy one and told the guard to escort him to the showers. “Antoinette go with them and make sure he is completely clean before you bring him back.
The guard unlocked the cell and pushed the prisoner number one toward the shower room and Antoinette followed. The guard instructed number one to wash and tossed a bar of soap to him. Number one began his shower and lathered up and rinsed off and then turned around to face the guard and Antoinette. Antoinette asked the guard to have number one face the wall and put his hands above his head against the wall and to have him spread his legs two feet apart. The prisoner did so and Antoinette approached the rear of number one. She took the bar of soap and began rubbing it on the small of number one’s back making lather. Then Antoinette took her right hand full of thick lather and slid it down his crack to his scrotum. She then slid two fingers into his asshole and wiggled them for a couple of seconds. She soaped up her hands again and reached through his legs and grabbed his balls and gave a gentle squeeze. She then got her left hand full of lather and reached around his waist and latched onto his penis and began stroking him. Prisoner one immediately became erect. She teased him for about a minute until she was sure he was good and hard. Antoinette stepped away and the guard told number one to rinse off. The three of them returned to the cell area. Norma exclaimed “I see you got him nice and clean. Did you enjoy your shower number one?” “Yea I did.” “It’s Yes Mistress or no mistress and nothing else.”
I accompanied number two and essentially did the same process as Norma had previously instructed.  Gerda did the next and then Antoinette and I followed with numbers four and five. The guard called his other guard for assistance with number six who did not seem to want to cooperate with Gerda. After some commotion the guards subdued number six and brought him back to his cell. Norma had the guards restrain number six to the bars of his cell. They extended his legs away from the bars and secured them to rings in the floor. Norma walked behind number six and put out her right hand. Gerda hurried over and placed the black dildo in her hand. “Because it is your first time I am going to lubricate the devise before I insert it. Next time I will not be as gentle. If you resist it will hurt more” Norma told number six.  She pushed the dildo against his ass hole and slowly inserted the device until it was sucked into his rectum. Number six tried to remain silent but could not. He let out a howl as the devise widened his hole.  “Cuff his hands in front of him and bring him out in front of the others. Norma addressed him “Number six why didn’t you cooperate with your shower? Why did you resist Gerda’s inspection?” “No one is going to grab my balls like that.” Number six shouted. Norma pushed the remote and number six fell to the floor squirming in pain. “Stop, Stop, Stop” he shouted. Norma let go of the button. “Are you talking to me?” Norma asked. “Yeah”, he replied. Norma pushed the button again. When she let up he whimpered “Yes mistress” “Are you going to take a proper shower now?” Norma asked. “Yes mistress” he answered. Norma then addressed the other prisoners. “You see what happens when you do not follow orders now. I expect you all will behave accordingly.” Number four said “Mistress where are our clothes?” “They are being washed and sanitized. You are to remain nude tonight.” Gerda and the guard took number six back to the shower where Gerda told number six to remove the dildo and wash it with soap and water. “You slip your finger into a small ring and steadily pull it out.” Number six let out a moan as the device escaped his orifice. “Clean it very well but try not to get water on the handle end. Hand it to me and I’ll dry it.” Gerda was particularly rough with her inspection. She brought him back to the cell still holding his dick in front of him. “Good night, get some rest you are going to need it tomorrow.” We all went upstairs and the guards stared their rotation of duty over the prisoners.
Day two started with the prisoners be awaken at six thirty and hustled into the showers one at a time. Antoinette and I arrived at seven with their vitamins and hormone supplements. Number three asked what they were and I responded that they were vitamins to help sustain them while they got used to their new diet. Antoinette issued each of them their new uniform. It was simply a spandex thong. There was a different color for each prisoner. They were all pastels. There was light fuchsia, soft pink, baby blue, light lime green, ivory, and light yellow. Number five protested and I warned him that I would find it most satisfying to fit him with a persuader device for the duration of the day. I also explained that we were going to spend the next several hours in the gym doing exercises and I was sure he did not want his junk flopping around.  “You could bruise yourself and it would be painful later.” The two guards then cuffed each of them and brought the prisoners up to the gym. Gerda was waiting for them and explained what the routine was going to be on a daily basis. Within ten minutes she had every one of them sweating profusely. Obviously they were not athletically inclined. I remembered my first encounter with Gerda and how my ass cheeks hurt for days after Gerda’s workouts with all those ass tightening exercises.
Almost two weeks passed when Norma addressed the prisoners telling them that one of them or all of them had brought lice into the school. She instructed all of them to go to the showers and shave all their body hair off and to keep it off for at least two weeks. The following day in the gym was awkward for them as they paraded into the gym. Antoinette and I just stared at the clean shaven bodies. They still only had the tiny thongs to cover themselves. All of them had lost mega pounds and excess fat because of the strict diet and exercise. When dinner time came on the fifteenth day Antoinette pushed a cart containing two grilled hamburgers and baked beans which smelled heavenly. All six of the prisoners were standing in their cells with their tongues hanging out. Norma entered and held up a very sexy, pink baby doll nightie and asked who wanted to wear it tonight. Obviously there were no takers. “That’s too bad because the hamburgers were made just for the one who wanted to please me and wear the nightie.” Norma said tauntingly. Number four said “Mistress I’ll wear it if I can have those burgers and beans.” “And so you shall” as she handed it to number four to put on. After he had the nightie in place she handed number four a plate with two burger and some beans. She then told me to take the cart back to the kitchen. The other five began hollering and complaining. “Silence. You have no say on how I run things here. You all had the opportunity to do as number four chose to do and you refused. Now for your insolence you will be punished. Antoinette supervise the punishment.” Norma barked her orders and left.
Antoinette watched as the guards fastened each prisoner except number four to their cell bars and their ankles to the rings on the floor. She then inserted a persuader device into each of their buttocks. The guards then cuffed each of the five and released them from the floor rings. One by one Antoinette activated their dildos causing all kinds of howling and contortions. Antoinette started getting into it and did a second round of torment. She had them kiss her feet to get her to turn off the devices. She had number six suck her toes. “You will go hungry tonight and I suggest you take the Mistresses offers in the future.” and then she left. The guard told them to remove the dildos and wash them in their sinks and hand them out of the cell.
That night the heat was lowered in the cell area causing the prisoners to shiver throughout the night making a most unpleasant sleep. Satin night gowns in pastel colors to match their thongs were hung in their cells, with no instructions. Each night the temperature was lowered a little more until all the prisoners were wearing the satin sleep shirts out of desperation to keep warm.
After the showers the following morning Norma stood in front of the prisoners and said that she wanted them to wear miniskirts today, but only on a volunteer basis. She added that anyone wanting to wear the skirt all day would enjoy two Sunnyside up eggs and bacon breakfast the following morning. All but number six volunteered. They were each given their little skirts to wear. They went to the gym for their morning exercises and then to the class rooms to learn more about feminine grooming techniques. They practiced sitting, standing and stooping with their knees held together. They practiced walking placing one foot directly in front of the other so that they swayed their ass with each step. They learned to paint their nails with polish, even using cotton balls between their toes to avoid smudges. By the fourth week the prisoner were filing and polishing their nails on a daily basis. Norma never stopped the every other day requirement to shave. All of the prisoners cooperated except number six. Number six wound up with the persuader device stuck in him every day and forced to comply with the orders.
After another week each prisoner was issued a matching bra with insert pockets for bags of gelatin to fill out the cups. “You will wear these every day.  I want you to get used to the slight additional weight on your chest as well as the inconvenience of something in the way when you reach for something.
All of them were developing nicely. All had lost considerable weight and the exercises had trimmed their waists and developed their breasts. The hormone supplements had had the expected results of slightly shrinking their genitalia and messing with their emotions. Now almost three months into the program and they were ready for the beginning of the transformation. Norma stood in front of the prisoners and told them that there were several bedrooms with soft beds and luxurious accommodation that they could move to under certain conditions. “Numbers one through five have earned the right to apply for these nice rooms. Number six will remain here until I am satisfied that you are ready to move forward.” Norma announced. A guard, number one without cuffs and Antoinette went up to a new bedroom on the top floor. Then I escorted number two, Gerda took number three and Norma took number four. Antoinette returned for number five. Each prisoner was told to explore their room and go through their dressers and closets.
Antoinette visited number one while he was exploring his dresser. “Come over here and strip.” She ordered. Number one did as requested. Antoinette walked around behind him and slid her hand over each breast and began gently scraping her finger nails across his teats causing them to become hard and sensitive. She continued toying with him until he was sporting a manly erection. Antoinette walked around in front of him and gave his hard-on a resounding slap causing it to immediately shrink. “I didn’t give you permission to get aroused.” She then leaned into him and planted a sensual kiss ending with her gently biting his lower lip as she withdrew. She reached down and softly stroked his penis.as she began kissing his neck and nibbling on his ears. Again number one could not prevent his dick from rising to the occasion. “I like teasing you. Do you like me teasing you?” she cooed. “Yes Mistress.” “Good because I’m going to do this every day until you stop being aroused my attention.” All the women were exploiting the prisoners in a similar fashion and making a similar promise.
Norma asked everyone to meet in the room at the end of the hall for an explanation. She very matter-of-factly told them she wanted them to become in every way possible young women. “I want you to wear women’s clothes, high heels and stocking and sexy outfits. I want you to walk and talk and act like young women. As long as you do this I will allow you to stay in these quarters. There will be bonuses for those who go beyond what is expected so look for opportunities to excel. You are still serving your sentence and will be guarded so please do not betray the trust I am placing in you” Norma stated.
The following day at breakfast in the dining hall all five of the prisoners were dressed in various sexy outfits with heels and nail polish. Some were wobbling a bit but all were really trying to comply with the directive.  Number six remained in the sub-basement cell.
Another two weeks of allowing the prisoners time to acclimate themselves into living as women in comfortable surroundings appeared to be working as planned. Norma brought in a hairdresser to create individual styles for each of the prisoners and taught them how to care for them. The prisoners would romp around on the tennis court in the cutest tennis outfits and swim in the pool wearing their bikinis. Number two looked particularly fetching in her pink running outfit with micro short shorts, halter top and pink sneakers.
Number three stood in front of his full length mirror and assessed his figure. His waist had shrunk considerably and then he noticed his once hairy chest was stopped sprouting hair between shaves. In fact most of his body hair had stopped growing except for the hair on his head which was now almost shoulder length. Both his breast were swollen and he reach up to caress them. They were sensitive to his touch sending a shiver to his groin. He squeezed them to find them to be full protruding. He then went and examined his bra to find that the gelatin bags were much smaller then what was issued initially. His own flesh was now filling out the cups of his bra.  Back in front of the mirror he continued his assessment to note that his buttock had swollen but his legs had slimmed down considerably.
After breakfast while out on the grounds he asked most of the other prisoner if they had noticed the changes. Most embarrassingly admitted they too had seen the changes in their bodies. That night the prisoners were all preening in front of their mirrors, naked admiring their girlish figures. They were striking posses more like women then men.
Norma decided it was time to advance the training another notch. She invited a female friend of hers over for tea and one by one had the prisoners join them in the well-lit office. Her friend unexpectedly brought her niece explaining that her sister had sheltered the young girl and it was time her niece learned a little more about the world. I or Antoinette would serve the tea and witness the reaction of each prisoner. Norma would say to the prisoner, “Darling would you please disrobe for our guests. They would love to see all of you.”  Shock was the immediate reaction of course. If the prisoner refused I or Antoinette would escort her back upstairs and bring a different prisoner down. A guard would assist in the insertion of the persuader device and we would amuse ourselves with the recalcitrant prisoner later. On this particular day only number three had refused to strip in front of Norma’s guests. Each one would shyly and slowly hand their clothes over to Norma until they were standing in their panties in front of this stranger. Then with a little prodding from Norma would slide their panties down to expose their tiny dicks. Norma would hand their clothes back to them and they were dismissed back to their rooms. The woman confided in Norma why she had brought her niece and what she would like to do. Norma nodded in complete understanding and asked that number three be brought back down.
Norma spoke in a whisper and told number three that she was disappointed in her earlier behavior. “Now I’m going to turn this on at the lowest setting so that it is right between a tantalizing vibration and an annoying grating on your prostate. I am going to leave it on during the entire time you are performing for us. Do you understand? Now I don’t want to have say commands more than once and I expect you to comply immediately. Please take your clothes off very slowly in a strip tease way.” Number three began to disrobe in front of the woman and her young niece without any resistance. When she got down to her little panties she stopped. Norma turned the dial up one notch and number three jerked a couple of times and started humming as she slid her panties down her legs. “Step closer in front of my guest so she can better see your little dinky.” Number three moved within six inches of the woman and the young girl.
Norma then had number three restrained to the coffee table. It was a substantial table and number three was spread-eagled on top of it with the device still humming away inside of him. The woman reached out and stroked number three’s penis and brought it to life. “Oh look how cute his penis looks. You touch it dear” she said to her niece. Norma stood and excused herself saying “I think it would be appropriate if we left you and your niece alone to play and learn at your own speed and pleasure.” After Antoinette, Norma and I had left the woman and her young niece alone in the room with the restrained number three; the woman showed her niece the intricacies of the male genitalia. Where it was sensitive and how it filled with blood to become erect. She instructed her on where the sperm was stored and how it came out through ejaculation. The woman took the blindfold that Norma had provided and tied it in place on number three followed by a gag that silenced any noise that might come from him. The woman then helped her niece disrobe and straddle number three. She gently rubbed number three’s cock against the young girl’s clitoris causing her to gasp. “Oh his dick is vibrating.” The Niece exclaimed. “That’s because of what they put in his ass to make him cooperate.” the Aunt explained. She kept at it until see saw the tell-tale sticky fluid seep from the young girl. The woman encouraged the girl to continue using the erection against her clit to achieve even more pleasure. The woman rolled a condom onto number three’s erection. The woman then had the girl rise up onto her knees and place herself directly over the throbbing penis. “Now I want you to lower yourself onto him until you feel discomfort. Go slowly and enjoy the feeling you get from sliding down his shaft. The girl did as requested letting out little yelps of delight as she descended. “Oh this is so neat and feels so good,” the Niece whispered. The young girl actually moaned as she rose back up number three’s shaft. The woman encouraged her niece telling her to increase the tempo a little and possibly twist herself left and right and to squeeze her vagina as she continued her up and down motion. The girl tried all sorts of contortions and began squeezing her vagina on both the up-swing and the downward motion. “This feels really good Auntie. Why can’t I go all the way down on him without it stopping?” the niece asked. “That’s because you are still a virgin. You have not been penetrated yet. That is what we are doing today so that you can start enjoying the pleasures that await you without the embarrassment and pain of your first time looming over you. The woman explained. The young girl continued to please herself on number three’s erection and was going faster and faster. The niece was panting, moaning and yelping as the pulse quickened. Suddenly the girl screamed and stayed perfectly still for a moment. The girl then let herself slide the rest of the way down number three’s penis until she was firmly ensconced on his pole. There was a tear on her cheek and her Aunt whisked it away and told her to ride up and down without any further displeasure. The girl did so with complete abandon until she experienced her first climax. The girl had experienced very similar feelings alone in her room when she would play with herself, but this was somehow different. The woman helped her niece off number three. “Look at the blood on him and on me. What happened? Did he cut me?” the girl asked in terror. “No, no my dear. There is a small piece of skin that was growing across your cervix preventing you from enjoying yourself. It is now gone and you are free.” The aunt explained. Norma had the forethought to provide a basin of warm water and wash clothes in the corner of the room. They cleaned themselves up and threw a towel over number three who was still restrained wanting a release. The aunt picked up the little tea bell and rang it. Antoinette arrived at the doorway asking, “Did you need something madam?” “Yes. We’re finished here. You may clear the mess from the room thank you.” The woman grumbled.

Two days passed and Norma instructed the prisoner how she wanted them to expose themselves when ordered to do so in the future. “I want you to covertly push your penis and scrotum between your thighs, while pressing your thighs together, so nothing is exposed in the front. You are to do this as you lower your panties so that even when your panties are around your ankles you will still appear to be a young woman.  She had all the prisoners practice until they all could do it perfectly. Norma invited a male friend to the school. She then summoned the prisoners, one by one, to join them. She ordered them to strip in front of the man. She had them stand coyly in front of the man with their penises hidden between their thighs for several minutes. She then told them to turn slowly around three hundred and sixty degrees. As soon as the prisoners began their turn their penises would spring loose and not be seen until the prisoner had completed the full turn. She then had either Antoinette or I bring them to ejaculation with our mouths while the man watched. Fortunately all of the five complied with the instructions and no punishment had to be administered. I was disappointed. The following afternoon Norma invited two couples over and summoned two prisoners to join her and her guests at the same time. Norma instructed the first prisoner to remove the second prisoner’s clothes, except for the panties, very slowly and provocatively. Then she had the second prisoner strip the first prisoner down to her panties. “Now I want you both to take each other’s panties off. They both expertly did as instructed hiding each other’s penies as they slid the panties down and off. She then told them to smell the musk from the panties crotch.  She then instructed tem to lie on the floor in a sixty-nine position and give each other pleasure with your mouths to the point of a rock hard penis without ejaculation.” Norma commanded. Not one of the prisoners wanted to give a blow job to their fellow prisoners and all had to be fitted with persuaders. In the end all five of them complied with Norma’s wishes and gave a stunning performance for the guests. The first set tentatively took the others penis into their mouths and had to have the remote activated until they began giving an earnest blow job. You could see the revulsion on their faces as they sucked each other. Norma had them stand next to each other with their hard-ons protruding out in front of them. “Now was that so difficult? Perhaps next time you will enjoy it more without the pain of the persuader.  Go to your rooms” Norma barked.  It was fun watching the reaction of each prisoner allowing a penis to slip into their mouths and then watch as each one began to suck on the penis as it grew in their mouths. This was the point where their male spirit was surrendered to the female life. This was when they gave up their resistance to the idea that they were now and forever she-males.
The following week was spent teaching each prisoner how to butt fuck each other. Obviously this took countless trials and errors and lots of moaning from the persuaders. By the end of the week Norma had each of them bringing their assigned partner to full erection so that they could insert themselves into their butt holes. It was sheer pleasure watching the expressions on their faces as they pushed themselves into the warm tight confines of their partner’s nether hole. They went from horror to sensual pleasure. Norma told the fuckee to clench his cheeks like Gerda had taught them. Norma enticed the prisoners by giving the first prisoner who mastered the task a special show. She had Antoinette and I perform a strip tease act behind sheer curtains down to our panties and the do a sixty-nine routine with our panties still in place thus not divulging our true gender. That was all the prisoners could talk about when they were returned to their rooms. All the other prisoners could not wait to be asked to perform so that they too could witness this special show.   It didn’t take all that long for both the fucker and the fuckee to actually enjoy the sensations of the act.
The next week was spent training the prisoners on the art of catering. They were taught how to take drink order, serve cocktails, serve different dinner courses and generally be a servant. All prisoners were given little French maid outfits with the usual frilly petticoats and exposed lace covered ass cheeks. All had black four inch heels and white lace head pieces. The cocktail party and dinner was scheduled for Saturday evening. The prisoners were told that each had a chance of being graduated from the school with a new identity. Each could receive a new name, social security number, drivers’ license, and passport if they were selected. “Be on your best and obedient behavior tonight. This could be the first day of your new life.” Norma encouraged.
Throughout the evening there was plenty of grouping and feeling up by both the men and the women at the party. None of the prisoners resisted at all, not wanting to be disqualified for possible graduation. After dinner Norma addressed her guests, “I have invited you all to my school tonight to not only witness what I have been able to do in a very short time but for you to have the opportunity to purchase one or more of these well trained and obedient she-males. There is a thirty day money back guarantee and I’ll throw in a unique persuader device that I am sure you will not need but only as assurance of implicit compliance. Now the asking price is twenty-five thousand dollars but tonight I will accept a mere twenty.” Norma then had all five of the prisoners line up in front of the guests and the guests were encouraged to come forward and make a closer inspection of the merchandise. The guest came up to the prisoners and began lifting the hem of their skirts and some slid their panties down to reveal their little penises.  Norma asked all the guest to retake their seats. “I would like to demonstrate the persuader device for you. We have a prisoner who has been extremely difficult to convince of his true destiny.” Norma gestured toward the doorway where number six was standing nude except for the protruding device in his ass. “Number six Come over here and kneel down. Number one stand in front of number six and remove your panties. Number six give her a very nice blow job and swallow his cum for our guests viewing pleasure.” Norma ordered. Of course number six refused to even move. So Norma pressed the button on the remote and number six bucked and squirmed until he raided his cuffed hands in surrender and began giving number one a blow job.
“Number two seeing as you now have the largest of the cocks here, I want you to butt fuck number six. Again number six resisted and received more agonizing torment. Number six was required to give blow jobs, and ass lickings and to receive butt fucks and facials. Number six was then returned to his cell.
“There are contracts between you and your new acquisition that provides for only humane treatment of the specimen in exchange for complete compliance and enduring entertainment.  I will now accept your orders. All sales are final and the first guest to select a particular she-male will win that specimen. So please hurry filling out the order forms that are on your tables in front of you.” Norma explained.  All five of the graduating class were purchased and taken to their respective mistresses homes.