Guilty Pleasure

by Jennifer White

  

"So young man" said the DA, you freely admit that you shot Brandon Winters?"

"Yeah, I did it" said the angry teenager. You could see the rage in his eyes.

"And you told the police that you did it because you wanted to prove to the other guys how big of a man you were?"

"On the streets, you've got to prove you're masculine" he said. "But what do you know, you wear a suit."

"Yes I do young man. And soon, you'll be wearing a suit too. A prison suit."

"Objection!" said the court appointed attorney. It was only his second objection during the entire trial. Either through indifference, boredom, or incompetence. Not to mention that his client was guilty as hell, and he hated pro bono work.

"Sustained" said the Judge.

"No more questions" said the District Attorney.

 

The public defender did not put up much of a defense. This client had a previous record of violence, and admitted that he did it. But he refused to take a plea. He insisted on having a trail, so he could tell everyone what a big man he was.

"Son, before I pronounce sentence on you, do you have anything to say?"

"Yeah. I did it, and I'd do it again."

"So you've said. Bill Moore, you have been found guilty of 2nd degree murder. The standard sentencing guidelines say that I should give you 15 to 20 years. You would serve at a youth facility until you turn 18, then you would be transferred to the state prison. You would most likely be put into solitary confinement there, for your own safety, until you are around 21. When you get out, you will be in your thirties, with a felony murder conviction. Your chances of having any kind of life will be very poor."

The DA smiled. This boy was the kind of trash that he was glad to get off the street. A prison term like the judge was describing would be hard time. Prison was not a pleasant place, especially not the state prison. With all of the violent offenders incarcerated there, only the strongest would survive.

"However, I am not willing to just throw your life away. After considering the options, I have decided to turn you over to a hospital, where you will undergo intense therapy for three years. You will be able to get an education, and be back out on the street by the time you are 21....if and only you fully complete the program. You will learn a trade as well, with mandatory classes every day. You will be rehabilitated and educated."

"I object your honor!" said the DA. "This sentence is outrageous!"

"You can't object counselor; this is a sentencing. However, let me add this: if Mr. Moore does not fulfill all the terms of his treatment, he will be turned over to the state prison, and will serve the full term of his sentence, with no hope for parole. Does that satisfy you sir?"

"Thank you your honor. I still think he should do hard time for such a terrible crime. But I defer to your judgment."

"Bailiff, take Mr. Moore to the transfer cell, and have the papers prepared."

 

One hour later, the police put Bill Moore into the back seat of a cruiser, and started the 3 hour drive to the facility where he would spend the next few years. They were upset as the DA about it, thinking that such a lowlife should be going to the harshest prison possible. But they had no idea what was in store for him. Something so terrible that they would tremble in fear if they knew what it was.

* * *

 

After arriving at the complex of low white buildings surrounded by tall fences laced with razor wire, Bill was led into the reception area, then through the secure door that he would not pass through again for years. The paperwork was signed by the staff, and he was now officially a resident of the Felony Eradication Mental Asylum & Labor Education.

They presented him papers to sign, waving all rights, and acknowledging that he was in their exclusive care. Even power of attorney was signed over to them. He didn't care. This was going to be a cruise, instead of doing hard time. He did it gladly.

Bill was led into a room where he was seated, and uncuffed. A few minutes later, a woman in a white lab coat walked in. Wow, they had chicks here! He was going to do her before he left here. She wanted him. He could tell.

"I am Dr. Wendy Hoyt. I will your councilor for the duration of your stay here. I know that you shot that other boy, because you wanted to prove your masculinity. Here, you will learn what it really means to be a man."

"Yeah, I've heard all that rap before" said Bill defiantly.

"Not like you're going to get here. But first, do you want a drink?"

"Are you serious?"

"Of course. Whiskey good for you?"

"Sure thing babe" he said.

"You will address me as Dr. Hoyt."

"For a drink, sure, *doctor* Hoyt."

"That's better. Here you go. Bottoms up!"

He downed the drink in one big gulp, and felt it burn as it went down. They had liquor in here too. Cool.

She rattled on about alternative treatment therapy, displacement, and a bunch of things he didn't understand (or care to learn about). He mostly just stared at her tits. He was really relaxed, and soon was almost falling asleep.

"Good, I see the sedative has almost set in" said Wendy. An aggressive young man needed to be tranquilized, to keep him from getting violent about what was to come next.

"Pay attention now, this is important!" she snapped, taking off her jacket, revealing her tight shirt she wore underneath. She had his full and undivided attention now.

"In order to reduce your overly aggressive masculine tendencies, we need to reshape your self-image. We need to take away the negative violent traits, and replace them with positive gentle traits. And in order to do that, we are going to demasculinze you."

"Demasculinize? What does that mean?" he said, barely able to talk because he was so relaxed from the drug.

"It means that one by one, we are going to take away your negative masculine traits, and replace with positive *feminine* ones instead. For example, you will no longer wear jeans and T-shirts; you will dresses, blouses and skirts. You will no longer wear boxers; you will wear panties and a bra. We will change your body, your thoughts, your feelings, and even your name. As long as you are at this facility, your new name will be *Jessica*. The name Bill has no meaning anymore. There is no Bill. There was never any Bill. You are Jessica now. You have always been Jessica."

"No!" he said defiantly, trying to stand up and slap her. But it was no use. He was too weak.

"We will take you to the operating room now. When you wake up, you will find that you have large breasts. They will be your first major symbol of femininity. Then over time, we will add to you, until we turn you completely into a kind, loving, gentle *girl*."

"No...please" he mumbled, even as he felt darkness starting to overtake him.

"Have a good sleep now Jessica. I look forward to seeing you in a few days, when you have boobs."

 

Bill was out like a light, and Dr. Hoyt pushed a button to send for the orderlies.

"They had better use a D cup" she said, writing out her order on a pad of paper. "This one will be a hard cookie to break."

"Or a hard nut to crack" joked the orderly, causing her to smile. There would be much nut cracking for him over the next few days.

* * *

 

When Bill awoke from his drug induced sleep, he immediately wanted to feel his chest with his hands, but he found that they were held tightly in place by metal restraints of some sort. He tried to look down at his body, but his head was held in place as well.

But he could feel something was different. First of all, there was this *weight* on his chest that didn't feel right. And a great soreness as well. He struggled to move, but it was useless.

"Ah Jessica, you're awake" said Dr. Hoyt.

"I'm not Jessica. I'm Bill" he replied defiantly. "I want to see my lawyer, and get me out of here. I want to go to a normal jail. This place sucks."

"I am afraid that you are greatly confused young lady" said the doctor, shaking her head. "You see, first of all, *you* signed the papers handing over power of attorney to *me*. That means that I can conduct legal transactions on your behalf. So really, *I* am your lawyer now. And I've already processed one transaction. Here, let me show you."

She reached into her briefcase, and pulled out several sheets of paper stapled together. She held it up for him to see. He wasn't a very good reader, so the legal mumbo-jumbo made no sense to him.

"What's that?" he said.

"This is a set of papers which I have filed on your behalf. First, we have begun the legal process for change of name. You can see here your old legal name, Bill C. Moore, Jr. And this is your new legal name. Jessica Anne Moore."

"I'm not Jessica!" he protested.

"According to the government you are now. According to the legal system, you are now. According to your new social security card you will be receiving, you are. To the world now, you are Jessica Anne. And soon we will beginning the paperwork to apply for a change of gender status."

"What does that mean?"

"It means that where it says 'Male' on your legal records, we will apply to have it say 'Female' instead. Soon, you will legally be a girl."

"No! Please stop!" cried Bill. Although his legal name was Jessica now, he would still think of himself as Bill for some time to come. But Dr. Hoyt went to work on him, making him say over and over that his name was Jessica now.

"When you hear someone on the staff call out the name 'Jessica', you will respond to them. If you are ever caught referring to yourself as 'Bill', or even responding to that name by mistake, then you will be punished."

"Punished?"

"Yes. You will not like the punishments here. If you behave like a good girl, then you will find that when you leave here, all the changes to you will be reversible. We will turn you into a girl on the inside, but you could always get your boobs removed, and live out the rest of your life as a man. I think you will come to prefer being a girl though."

"Never!"

"We will see about that. Anyway, at the stage you are at, if you do anything that forces us to punish you, we will respond by doing something to you which you cannot reverse. Something to make you more feminine, but in a *permanent* manner. If you behave very poorly at first here, until we have had a chance to feminize your mind, then you will soon find yourself in a girl's body."

"What?"

"You heard me. If you are disobedient, if you don't follow orders, if you are late for class, if you act aggressively, or in a masculine fashion, then you will be turned more and more into a girl. So really, you would be doing it to yourself. So go ahead, be defiant! I would love to inject you with female sex hormones. I would love to retrain your mind to make you desire boys. Just give me the chance by acting poorly."

Bill just looked up at her. She was crazy! But she wasn't kidding around. She meant what she said.

"I think that you will come to like being a girl Jessica. I think that before you leave here, you will *beg* us to complete you as a girl, by giving you a real vagina of your own."

He shook his head, or at least tried to.

"Now Jessica, you understand the rules. I am going to release your bonds. You can decide what to do next. You can go put on the bra and panties that I've laid out for you over here, then put on your dress, and join us for lunch. Or you can disobey me, and be punished."

"Sounds like a punishment either way" he replied.

"Except that wearing a bra, or wearing a dress doesn't make you a girl. You can do those things, and still be a man. That is what you need to really learn. Being violent doesn't make you a man. Being aggressive doesn't either. You can be calm and gentle, but still be a man. But it is a hard lesson to learn. You can start learning how to be a gentle man, or you can start to become a real girl. Your choice."

With that, she got up, and left the room. As she walked out the door, there was a buzzing sound, and the metal restraints opened up, then retracted into the side of the bed. Bill was free to get up.

 

He didn't realize that he had been asleep for days, enough time for him to mostly heal from his breast implant surgery. He took off his hospital gown, and looked at himself in the mirror.

They had removed all his body hair, plucked his eyebrows, and even given him big tits. His chest still ached, as did the spot in his belly button where they had gone in to do the surgery. He just could not believe that when he looked in the mirror, he had breasts!

They were so big! He got hard just looking at them, then felt ashamed that he was excited about looking at *himself*. And he was cold. He needed to put some clothes on.

He looked in the closet, and it only contained one thing: a white dress. The bra and panties that Dr. Hoyt had promised were laid out on the table. He had a choice to make now: put it on as she told him, or call her bluff and see what they really did for disobeying the rules.

She had to be lying. They wouldn't do something like that for punishment, would they? It had to be illegal or something. But as he crossed his arms, and felt the large firm mounds under them, it sunk in that these people meant what they said. They had done *this* to him, so they certainly wouldn't hesitate to shoot him up with hormones.

The scariest part was it sounded like she *loved* the thought of doing that to him. What kind of sick person would want to do that? He took the only choice that he had: he walked to the table, put on the panties, then struggled for five minutes to get the bra on. It was hard enough taking one off a girl. But they were even harder to put on.

He felt ridiculous after he put on the dress. He almost died looking in the mirror. He was going to walk out of the room now, and let people see him like this? No way!

He peeked out the door to see if the coast was clear. He saw several women doctors talking in a group down the hall to the left. There was one chick walking the other way. Then he realized: it was no chick. It was a guy, with long hair, makeup, and a dress.

Then he saw another. And another! Bill realized that all of the inmates here were like him. They were all violent boys, who were being turned into girls. His face was beet red.

"Come on Jessica, lunch is getting cold!" said Dr. Hoyt. "Its all right dear. You can see that you're not the only one here. Don't be embarrassed. None of the other girls will make fun of you. They all went through the same thing when they arrived."

Bill gingerly started to walk down the hall. Dr. Hoyt led him to the cafeteria, where there were 30 or 40 other youths. They were all in various stages of feminization. Some looked like real girls, with pretty faces, curved hips, and long hair. Some looked like guys in dresses, with big tits. Just like him.

He also realized that all the doctors and workers here were women too.

"Come on Jessica, eat up. You have ballet class in 30 minutes" said Dr. Hoyt. "You don't want to be late do you? Oh and remember, eat like a girl. Mind your manners, and I won't have to punish you."

Bill took a small bite of the salad, and tried to look polite as he chewed it quietly.

* * *

 

Bill's schedule every day was quite full. First thing, he would rise at 6:30 in the morning, and start his 'beauty ritual' that he had been taught. He showered, shaved (including his legs and underarms when need be), put on his schoolgirl uniform, makeup, jewelry, cute shoes, and all the other required accessories. He didn't think to wonder why he never had to shave his chest hair. While he had been under the knife, they had used a special laser to permanently remove the hairs on his chest. The hair on his head was still short, but they told him that in time it would grow out so that he could have a prettier hairstyle.

After breakfast, he had regular school from 8:00 until noon, when they broke for lunch. He had to learn math, English, history, and other classes. It was just like being in high school, except that it was more intense, faster paced, and he was in the class as a girl.

Bill had to remember to hold his schoolbooks up to his chest, like a real girl would, so that he would avoid punishment. He had talked with several of the other students, and confirmed that in fact they *did* dole out serious punishments. The boy named Marie told him that after being injected with estrogen for the third time, he could not longer 'get it up'. The thought of losing what he had between his legs really scared Bill, and he tried his best not to break any rules.

After lunch, it was time for "Fem Ed", where he learned how to be a girl. There were classes on how to put together a cute outfit for one's self, fashion rules, styles of clothes, what was appropriate for a given occasion, and even how to shop for bargains.

Then there was a class where they worked on the proper way to walk, talk, sit, stand, move...how to act like a girl. It was difficult, but the ballet class that followed helped greatly with improving posture, grace, and poise (although it was the height of humiliation to wear a pink tutu).

The next class taught women's history, as well as topics such as how to care for and raise your baby. They even had dolls with motorized mouths that were used to learn how to breast feed.

Finally, there was a class on makeup, painting your nails, plucking your eyebrows, doing your hair, and all that. It was in this class that they pierced his ears the first day, and put in a pair of dangling gold ear rings with diamond chips.

After classes, it was time for dinner, then finally some recreation (ballet didn't count, in his book). They showed a movie every night, but it was always what he would call a 'chick flick'. Stories about girls. Or about romance. Or about relationships between women and their friends, or their families. There were no car chases, no explosions, no special effects. At first, he was completely bored. But after a few weeks, he started to understand some of the subtleties to it, and his interest started to grow.

After a snack, there was an hour of free time, before they went back to their rooms to study. This went on six days a week, with only Sunday providing a day of rest. It was exhausting, but for the first time in his life, Bill was starting to really apply himself to studying, and was beginning to really learn.

Unlike Bill's public high school, there were no fights here. Fighting would cause the stiffest of punishments. It was whispered among the students that if you fought, they would cut *it* off of you. None of them wanted to end up like that! So Bill, along with the other 'girls' learned to control their inner rage, and storm off in a huff instead of lashing out physically at someone.

* * *

 

There was no summer vacation for the students at the Felony Eradication Mental Asylum & Labor Education. It never let up. After ten months, it was becoming routine. Jessica was even used to being called by his new name now. He answered to Jessica Anne Moore every day at every class when they took attendance. And he had written his new name over and over, on every school assignment, using his new feminine handwriting they had taught him in Fem Ed.

He had only been tardy twice, in all the time he was there. The first time, they gave him a warning. The second time, they made him swallow a birth control pill. He never was tardy again after that.

After so much practice, he was getting good at walking and talking like a girl. The way he sat, stood or ran was different now. And it was almost to the point where he wouldn't have to think about it; he just did it that way.

 

As he filed his nails one evening, preparing to put on a new coat of nail polish, he reflected on how it didn't even bother him anymore to be wearing a skirt all day. At first, it was terrible, and he was aware of being in it all the time. But now he was *used* to it. He had grown accustom to how comfortable it was, and he didn't know if would like going back to wearing pants.

His hair was getting longer now too, almost down to his shoulders. Now there was enough to work with, and make something pretty out of it. He felt somewhat jealous of Marie, because his hair was a good six inches longer. But he knew it was just a matter of time before his hair got like that too. He wanted to dye it red, if they would let him. That color would help bring out his eyes he decided.

As the polish was drying on his nails, there was a knock at the door.

"Jessica, Dr. Hoyt wants to see you. Now."

"I'll be right there" he replied, grabbing his purse as he left the room. After all these months, it was another automatic reaction now. He walked down the corridor to her office, knocked, and entered.

"Hello Jessica. You look lovely today" said Dr. Hoyt.

"Thank you. You look very nice yourself Dr. Hoyt."

"You may call me Wendy, now that you're a girl too."

"Thank you Wendy" said Jessica. "Why did you want to see me?"

"To assess what progress you've made. From all reports, you have been a very well behaved girl."

"I try my best."

Wendy smiled at her.

"Now Jessica, I am going to give you a test, so we can measure where you are. The first part is a questionnaire. Please answer truthfully."

She handed over a booklet of questions, along with a form with little circles to fill in, and a #2 pencil. Jessica opened the book, and read the questions.

Most were easy. There were questions from the women's history class, like the fact that 'Bloomers' were named after the woman who helped change the rule that forced women to only wear dresses and skirts. Or easy questions about makeup and fashion.

There were math problems too, and questions about word definitions, or parsing sentences. But sprinkled in were some strange ones, like:

 

-True or False: I have male thoughts in my head.

 

-I wish I was a mommy:

A - all the time

B - sometimes

C - rarely

D - never

 

-Which is more important when going out?

A - to be on time

B - to have your makeup done just right

C - to have just the right outfit on

 

Jessica answered the questions, then passed the test back to Wendy. She walked over the a computer scanner in the corner, fed the sheet in, and studied the results.

"Very good Jessica! Your reading and arithmetic scores have gone up two grade levels since you entered this facility. And your femininity index is off the charts. I think you might be ready to advance to the next level already."

"The next level?"

"Yes. There is another building in this facility that you have not been allowed to enter yet. That is where we house the advanced students. I think you may be ready to graduate from this part of the school."

Jessica looked pleased to receive such high praise.

"I have a visitor waiting at the door. Go let him in" she said.

Jessica walked across the room, opened the door, and watched as a teenage boy walked in.

"Kevin, say hello to Jessica."

"What, another dumb girl?" said the boy.

"I'm not dumb" replied Jessica.

"What, you upset? You chicks are all alike. Just because you all want me, and I don't fall all over you, just because you got big tits."

"You are wrong. I don't want you. I want someone who is grown-up and mature. You're just a *boy*. I need a *man*!" sneered Jessica.

Kevin got a very hurt look on his face, and walked over aggressively.

"Even if you are a girl, I'm going to smack you for that!" he said.

Jessica cowered as he raised his hand, but Dr. Hoyt stepped in between them.

"Kevin, that will be all."

He raised his hand again, like he was going to slap Jessica, then stormed out the door.

 

"He was so horrid!" said Jessica angrily.

"Jessica, Kevin is not that bad. He is actually an actor we have hired. This was part of your test."

"Test? To treat me like that was a test?"

"We needed to test your reactions. And Jessica, you scored an A+."

"Really?" said Jessica, clasping his hands together over his chest.

"Yes. You have shown that you react to such a situation in a calm manner. Your emotions were strong, but your brain was stronger."

They had never been through a class to get trained for something like this. Jessica wondered where it had come from.

"I have one more question for you. Tell me now; if Kevin was a nice young man, kind and gentle, educated and articulate, would you be willing to go out on a date with him if he asked you?"

"Me? Go on a date with Kevin?"

Jessica's heart raced. It sounded so *exciting*, yet scary.

"He would never want to date me" replied Jessica. "I'm stuck here in this place, and he would want someone he could see on the outside."

"You don't have to stay here anymore, if you don't want. As long as you are willing to sign this paper, agreeing to under go one final surgery, we can send you home."

Jessica looked up, stunned.

"But I've only been here a few months! They said that I would be here for at least three years!"

"Jessica, you've been here for two and a half years."

"That's impossible! It wasn't that long ago the this all started...."

"No Jessica. The first week you were here, you broke a major rule, by threatening a teacher. We pumped you full of female hormones, and gave you an intense session that you might call 'brain washing'. As part of what we did, we made you believe that it was your first day here. You started again at square one."

"No..." whispered Jessica.

"Then the second time, you refused to obey a direct order from me. Again, we inundated your brain with female hormones, enough to alter how your body functioned. And we worked on your mind some more. Again, you thought it was the first day here when you woke up."

"It couldn't be."

"The third infraction was for going to class without makeup for two days in a row. The fourth was for failing math class. The fifth was for not shaving your legs. And the last time, it was because you didn't coordinate your outfit properly."

"No..."

"Each time, we gave you higher and higher doses. We put you on 'the pill'. We reprogrammed your brain. And now you are complete. You are a woman inside."

"That's not true!" said Jessica.

"Really? Tell me: you weren't upset at Kevin for calling you a girl; you were upset because he called you dumb. You told him you didn't want *him*, because you needed a *man*."

Jessica was stunned. It was true. Those were the words.

"You are a girl inside now fully, and you haven't even noticed. Now complete yourself, by signing this form. We will operate on you immediately, and as soon as you have recovered, we will release you. You are free to go. Just sign there. Or stay here longer if you would like."

With a trembling hand, Jessica signed the paper. She realized it was true. She really was a woman now. What did she need a *male* body part for? It didn't feel right anymore. And how would it go on a date if her boyfriend discovered what she had? No, Wendy was right. She *needed* to get this surgery done. It was the only logical choice.

Dr. Hoyt smiled. Jessica was about to become a real girl.

* * *

 

The taxi driver loaded Jessica's bags into the trunk, and they drove down the road to the campus. Wendy informed Jessica that she was to receive a full-boat scholarship at the state college, including housing at the women's dorm. She could pick her major, and gain the skills needed to start her career.

There would be plenty of guys there if she wanted to start dating, or find one to marry if she preferred to be a homemaker. They told her that unfortunately, she would never be able to get pregnant, but she could always adopt. Jessica wanted to be a mommy some day, so she hoped that she might even find a man who already had children from another marriage.

She got out of the car, wearing her best skirt and fall sweater. She pulled her long hair back, and admired the first view of the campus. She was ready to start her new life as a coed student.

* * *

 

Dr. Hoyt smiled as she filled in the final paperwork. Jessica was the 47th graduate of the program, and so far the success rate was phenomenal. They had taken troubled boys, who were destined for a life of violence, crime, drugs and prison, and turned them into intelligent women, destined for a career, and a happy family life.

There had only been one failure: Cheryl had dropped out of school, and was turning tricks for a living. But the other 46 women they had helped to create were happy and well adjusted.

But she had no time to rest on her laurels. There was a bus arriving soon with three more youthful male offenders, and she needed to start the preparations for their arrival.

"Get the OR ready, we have three new patients today" she said over the phone to her assistant. "And order some more bras. We're running low, and we'll be needing more soon."

She started the paperwork for the new arrivals, and smiled as she imagined the looks on their faces when they would wake up for the first time, and realize that they were being slowly turned into girls. She loved her job!

  

  

  

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