Charles Thorton is a fourteen-year-old boy who was shopping at Taylor's department store at a Mall not far from his parent's home. He's at the jewelry counter to find just the right necklace for his mom's 35th birthday. Unknown to Charles, three boys were caught shoplifting over $1000 worth of gaming equipment, and stopped just outside the store by store security. As they are taken back to the security office, the leader of the three boys sees Charles, and decides to get Charles in trouble by pointing a finger at Charles as being the mastermind of the theft. The head of security for Taylor's Department store at the Mall, James Conner, never identifies himself as he slaps a hand on Charles' shoulder, telling him, "You're coming with me you little bastard." That turned out to be a mistake as James found himself face down on the floor with his arm twisted behind his back and Charles' knee on the back of his neck. James is screaming at Charles to let him go, making threats about what he will do to Charles once he's let go. The commotion brings the Manager and Assistant Manager for Taylor's to the scene but they are unable to convince Charles to let go of their head of security; Charles doesn't believe anything both Managers say.

Officers William Weber and Robert Hansworth arrive, verify that James Conner is the head of security for Taylor's Department store at the Mall, and both Managers are who they claim to be. Charles finally releases James, who after getting his arm working again, almost succeeds in going after Charles, if it wasn't for Officer Weber stepping in between James and Charles. Officer Weber warns James about Charles' abilities to defend himself. Charles is told why he was 'attacked,' and told he will have to go to the security office. He makes a phone call to his mom, who tells him not to say anything until she, his father, and a lawyer from his father's firm arrive. Charles tells everyone what his mother told him, and he follows everyone to the security office. James still tries to get at Charles as they walk to the security office, but the Officers intercede, placing themselves between James and Charles, again. James won't be denied his prize, making Charles talk and getting back at Charles for how he was treated. Instead of just putting Charles in the holding room and waiting for Charles' parents, James lets Charles enter the room then he quickly goes into the room, slamming the door and locking it from the inside.

James' mistake was to take a police baton in the room with him, which he then slams down on the table in front of Charles in an attempt to intimidate Charles. Doesn't work, Charles is calm and concentrating on James. Charles responds to James shouts and threats by repeating what his mother told him about being questioned. As the Officers and Mary Myles watched on the other side of the one-way window, James starts to reach for the baton, only to see Charles holding it in his hand, and he had snapped it open. Charles warns James, but it does no good as James then tries to lunge across the table to grab Charles. James ends up with a broken collar bone and the ulna and radius in his right arm. Lynn and Jeb Thorton arrive with Terry Morgan, a lawyer in Jeb's firm. Officer Hansworth explains what happened, Mr. Obler returns upon hearing James screams and demands Charles is arrested for assault. Mary Myles proceeds to put Mr. Obler to sleep with a shot to his jaw, after being told by Mr. Obler she's fired. Officer Hansworth explains they have to take Charles in because of the charge against him, and he is put in the same holding cell as the three boys.

The next day Charles goes before Judge Ruth Walinkiewicz, who has reviewed the case and finds that the charges against Charles are lies. She is about to dismiss the case when George Strom, CEO of Taylor's, stands up in the gallery and tells Ruth if she dismisses the case Taylor's will take Charles to Federal Court and add additional charges. Recess is called and Ruth, Terry, the Prosecuting Attorney, and Charles meet in Ruth's chambers. There they discuss what additional charges could be brought against Charles if it's taken to Federal Court. Ruth has an idea to solve their problem, but it depends on Charles. Charles doesn't plead guilty, but accepts the punishment of the Court. And soon Charles finds himself on a train to Kingston, RI and Jane Thompson. It's there that Jane feels it's wrong for Charles to be with her, until she talks with Ruth and learns the whole story. Jane hatches a plan to help Charles clear his name, but only if Charles agrees to help show the leader of the three boys a side of himself he never knew existed. And Charles replied, "When do we start?"

After Jane explained what she needed Charles to do, and he accepted, plus continue helping Francis, she and Charles left the Library and went to the dining room, where Francis had set the table for their noon meal.

Francis was waiting at the dining room table as the two approached, and after being told by Jane, "Francis. Please tell Marie we are ready to eat,"

"Yes, Aunt Jane," she replied, and went into the kitchen to inform Marie. When Francis returned, she was carrying a turine of soup, which she sat in the middle of the table. Marie then came out of the kitchen carrying a platter of fresh baked bread, which she also placed in the middle of the table. Jane then indicated where Charles was to sit, but not before he helped all three ladies with their chairs; though to Francis it seemed strange for a soon to be girl to do something such as that.

When the soup course was finished, Marie and Francis cleared the table of the soup bowls and the turine, returning with bowls of potatoes, vegetables, and meat. While they had been in the kitchen, Jane had gently schooled Charles about helping a lady to sit at the table, saying young ladies don't do such things. So when Francis and Marie returned from the kitchen, Charles had to stop himself from standing and helping to seat the ladies. Jane, seeing Charles stop himself as he was starting to rise out of his chair, and the consternation written on his face, chuckled inwardly. Charles was going to be a great asset in not only helping Francis, but in clearing his name.

When they'd all had dessert, Marie went into the kitchen and returned carrying a tray with four small glasses and a decanter of wine. Francis had seen this ritual several times before, and knew what was about to happen next. Or thought she did, until she noticed all the rims of the glasses were pink, instead of one being blue. And she was further confused when after they'd drank a toast for Charles being with them, Jane told her to help Marie clear the table and then help in the kitchen. She'd take charge of Charles. But, Francis did as she was told, without her sometimes sour face showing.

It was after they'd all risen from the table that Charles said, "Marie, Francis, Aunt Jane, thank you for a lovely dinner. It was extremely enjoyable." This was something else Francis thought strange, since none of the previous boys had ever said anything so kind on their first day with Aunt Jane. Marie did give Jane a questioning look, to which Jane imperceptibly nodded toward the Library. Marie then told Francis to carry on with Jane's instructions and she'd return in a moment, as she and Jane went into the Library, where Jane told Marie her complete plans to help Charles clear his name by getting the boy coming next week to confess the lie he told in the beginning. A lie which caused Charles to be arrested, stand before Judge Ruth, and if not punished, would be taken to Federal Court by Taylor's Company. Where he could face additional charges brought by Taylor's, charges which would put Charles in Juvenile Detention until he was eighteen, then transferred to a Federal Prison.

Marie had been with Jane from the start of her Winsome Girl's School for Wayward Boys, and Jane knew the look on Marie's face said she was beyond angry at the injustice perpetrated on Charles. And like Jane, the boy coming next week was going to learn a lesson he should have learned some years ago. And they were going to learn a lesson about the boy.

When the two ladies left the Library, Francis had the table cleared, and from sounds coming from the kitchen, was starting to put things away and start washing the dishes. Charles, on the other hand, not given any instruction, stayed where he was by the dining room table, and stepped in beside Jane when she told him, "Charles, please come with me."

As she had told Charles, any time Francis was near, they both had to act as though Charles was just another boy Jane was going to teach, so Charles responded with, "Yes, Aunt Jane." As they walked out of the dining room and toward the stairs, Jane explained, in a voice only Charles could hear, what they were going to do when they reached his bedroom. And that he had a lot to learn in the short time they had before the ringleader of the three boys arrived the following week. All Charles said when Jane became silent, was, "This ought to be fun."

When they reached Charles' bedroom, Jane had him sit on the bed then sat beside him. Charles looked at Jane as she told him, "Charles, the first thing we'll do is choose your feminine name, which I believe should be Charlotte. It's close enough to your own name so you shouldn't get confused when addressed." Charles simply nodded his head in agreement. "Next, and if you'll follow me, I'll explain everything that's in that chest of drawers," and she pointed to the chest of drawers against one wall. They got up off the bed and walked over to the chest of drawers, where Jane started in the top drawer of panties, and proceeded to explain them to Charles. She told him about the style, when a particular style should be worn, or could be worn before opening the second drawer containing bras. Again, she explained styles, which bra should be worn with which panty, and when and where they should and could be worn. When she was certain Charles understood what she had told him, she opened the third drawer, which contained stockings and garter belts. She explained how to put on a garter belt, how to put on stockings and how to attach the stockings to the garter belt.

When she looked at Charles' face, she noticed it was slightly pink, causing her to chuckle inwardly at the sight. She then put her hand on his shoulder before she saw the single tear slide down his right cheek. She knew how hard it was for the boys sent to her to become young ladies and wear what they were forced to wear, so it wasn't hard for her to understand how much harder it was for Charles to do something he'd never done but volunteered to do so. She told him, "Charles, I realize this is all new to you and you're starting to have second thoughts. But if you'll trust me, really trust me, you'll get through this and perhaps learn something you'd not have learned any other way. And Charles, we will get your name cleared, I promise you." For the first time since this whole mess had started, Charles reached out and hugged Jane then started crying. As Jane held Charles she vowed that someone was going to pay for involving this sweet child in their vicious plans.

When Charles' crying slowed, then stopped, he got the hiccups, which caused him and Jane to start laughing. As his hiccups slowly stopped, Jane then took him into the bathroom so he could wash his face and get it ready for what Jane was going to do next. When she was sure he was alright, she took him back into the bedroom and to the chest of drawers, where, after opening the top drawer, she had him pick out a pair of panties. After seeing which panties he chose, she opened the second drawer and took out a matching bra and something else Charles hadn't seen before. She then explained how to put a bra on, then showed him the inserts he would wear until he visited her salon, where he would have breast forms glued to his chest. Jane had him put the bra on, then take it off and put it on again, so the action would start becoming ingrained in his mind. She then took out a garter belt, which matched the bra and panty he was wearing, and showed him how that was put on; again having him remove it and put on several times for the same reason. She'd chosen a nude pair of stockings, explaining how to bunch up one, place it over his toes, then slowly pull it up just as though he was putting on his socks. Of course, she had to get another pair, as he ran his nails through the first pair he tried putting on. His second attempt was more successful, as Jane then showed him how to attach the stockings to the garter belt; he took off and put on the stockings several times, without ruining the pair.

With his robe on, Jane took him over to the vanity, had him sit down and began a dialog about his hair and the different ways his hair could be worn. Because his hair was to his shoulders, Jane told him it was possible to have it cut in a more feminine style when they visited her salon. But for now, she was going to show him ways to make his hair look more feminine. Jane had Charles watch in the mirror as she did this and that in order to make his hair look more feminine. And when she'd finished 'fiddling' with his hair, he was shocked at the change of his appearance by just changing the look of his hair.

Jane walked over and picked up the chair sitting in the corner of the room and brought it back over where Charles was sitting. She looked Charles in the eyes and told him, "Charles, many boys have never thought of using makeup, unless they were cast members in a play, know nothing about makeup or how to apply it properly. And if they did, it was done in secret, lest they be found out by others. By your facial expression, you too find this thought difficult to accept, but for us to get your name cleared and to find out the whole truth of this matter, you must learn how to apply makeup to your face and do so in a proper manner. A proper manner which makes it appear as though you are not actually wearing makeup. When applying makeup, less can make all the difference to a girl's appearance, unless she's attending special occasions, which requires a different application. I want you to watch me in the mirror as I show you the proper way to apply your makeup. Then I'll have you clean your face and have you work through the steps I show you."

As Charles watched, Jane opened and closed several drawers in the vanity, taking out items from each drawer, and sitting them on the vanity counter. She would then pick up an item, show him the label on the bottle or kit, explain its use, and as he watched in the mirror, Jane would apply it to his face. All the while reminding him less is more, unless it's a special occasion. As Jane applied the second coat of mascara, and told Charles she was done, she watched in amusement as Charles marveled at the face he saw in the mirror. The face of a young, fourteen-year-old girl. Charles had totally disappeared. He was so mesmerized by what he saw in the mirror, that Jane had to finally shake him to get his attention.

Jane then picked up a package of cleaning wipes and told Charles, Charlotte, to follow her to the bathroom, where he was to clean off his makeup before washing his face. When his face was clean to Jane's satisfaction, they returned to the vanity, sat down, and Charles was instructed to apply his makeup following the steps Jane had just shown him. When Charles would make a mistake applying this or that to his face, instead of having Charles erase the mistake, Jane would again take him into the bathroom and have him clean his face. They'd return to the vanity where Charles would begin again; starting over after each mistake would help Charles gain muscle memory. After several false starts, Charles was finally amazed as he looked into the mirror and saw the young, fourteen-year-old girl stare back at him, the one he first saw after Jane applied his makeup. And he'd done it all himself.

Jane was pleased with how Charles, Charlotte, had progressed in such a short amount of time. Unfortunately, s/he had a lot to learn in a rather short amount of time, if her plan was to succeed. "Charles, Charlotte, I'm pleased with your progress so far, but there is much you have to learn if the plan is to succeed and your name is cleared. So, please follow me," Jane told him/her, as she stood up and walked to the closet. When Charles, Charlotte, was standing beside her in the closet, Jane began explaining about the different pieces of clothing hanging up on the clothes rack. She explained the type of material each was made of, the proper name for the color of the material, when and when they shouldn't be worn, and the requirements when Charles, Charlotte, was not in his/her room. Jane then turned her attention to explaining the shoes on a shelf at the back of the closet, and explained them in much the same way as the clothing. And again, Charles', Charlotte's, requirements when not in the bedroom.

With explanations over, Jane took a simple dress off the clothes rack, and shoes to match, and led Charles, Charlotte, out of the closet. She laid the dress on the bed and the shoes under the chair that held the robe, before having Charles, Charlotte, follow her to the chest of drawers. All Charles, Charlotte, saw when Jane opened the fourth drawer was what looked like folded up pieces of a soft material. As s/he watched, Jane took out four of the folded up pieces of soft material, closed the drawer and bid Charles, Charlotte, to return with her to the bed. Once they reached the bed, Jane sat the four on the bed, picked up the top one, unfolded it and began telling Charles, Charlotte, what it was.

"Charles, this is a slip, a garment worn under a dress. This one can be worn for everyday dresses, dresses you'd wear shopping, etc. These straps can be adjusted by pulling the strap through these metal pieces until the slip is positioned properly on your body. This slip, because it's white, can only be worn under light colored dresses. If you wish to wear this style under a dark colored dress, then a darker colored slip should be worn. That isn't to say a woman isn't daring, once in a while, and wears a dark colored slip under a light colored dress and a white colored slip under a dark colored dress, but you won't be daring while you're here at Seasons House. You WILL be properly dressed at all times." Jane watched Charles', Charlotte's, face for any signs of stress, and seeing none, laid that slip on the dress lying on the bed. Picking up the next slip, Jane went through another explanation of whens and wheres, do's and don'ts, before folding up the slip and setting it back on the bed. After showing Charles, Charlotte, the third and fourth slips, and an explanation for each one, she took the three slips back to the chest of drawers and returned them to the fourth drawer. It was now crunch time.

Jane studied Charles, Charlotte, as she walked back to the bed. It struck her that it wasn't Charles she saw any more, but Charlotte, a young, fourteen-year-old girl, and it was time she was treated as the young girl she appeared to be. Steeling herself, Jane said, "Alright, Charlotte, I want you to put on the slip so we can get it adjusted correctly." Jane watched as Charlotte gently picked up the slip and examined it, running her hand over the material to feel its softness. She watched as Charlotte bunched up the slip and was about to put it over her head, and told her, "Ah, dear, you're about to put THAT slip on backwards. Much like the shirts you wear, that slip has a tab at the collar in the back." Jane inwardly chuckled, as she watched the 'duh' look form on Charlotte's face, before she turned the slip around, bunched it up again, put her arms through the straps and let it fall over her body.

Jane stood back and examined the slip hanging on Charlotte's body. She saw it needed to be adjusted, and proceeded to show Charlotte how to adjust it so it hung correctly. She then loosened the straps and had Charlotte readjust the slip until it hung correctly on her. Jane then picked up the dress and gave Charlotte another explanation concerning the dress. She then had Charlotte put on the dress and zip it up, only to watch as Charlotte fought to get the zipper all the way to her neck. She didn't give up, and found her own way to complete the task. Jane then had her unzip the dress, take it off, and put it on again. This she did several times until Charlotte had little trouble putting on the dress and zipping the back closed.

Jane crossed her fingers mentally, as she told Charlotte to sit in the chair the robe was on. As Charlotte sat down, she sat as a boy would sit, causing Jane to gently admonish her to sweep the back of the dress under her as she sat, and to keep her knees together after she sat down. Jane instructed Charlotte to sit up straight and not to slouch as she sat, proper ladies always sat up straight. Jane then had Charlotte repeat the exercise of standing up, sweep her dress under her as she sat down, and keeping her knees together as she sat, several times until she saw it had become automatic with Charlotte.

Charlotte was then instructed to reach under the chair and take out the shoes, and to put them on her stocking covered feet. Charlotte had done well with her attitude so far, and Jane was hoping it would continue with what Jane was going to have her do next. "Have you ever worn heels before, Charlotte? Be honest with me. Have you?" Jane watched two things occur with Charlotte. The first was the shake of her head, indicating she'd never worn heels before, and the second being a questioning look on her face. Jane was not going to let the question go and asked, "You have a question, Charlotte?"

Jane believed she knew the question but let Charlotte ask it anyway. "Aunt Jane, you're now calling me Charlotte. Why?" Charles' question was sincere, without malice or anger. He was simply asking a question.

Jane smiled, walked over and knelt down before Charlotte, took both her hands in hers and told the girl, "Because we have so little time to get you used to presenting as a girl, and your girl name. Charlotte. You must be able to answer right away to that name so you don't give anything away when that young man arrives next week. It isn't to demean you in any way, just to help you adjust to something I see you've never done."

Jane could see Charles mull over what he just heard, then nod his head and tell Jane, "I guess you're right, Aunt Jane. After being called Charles for fourteen years, I wouldn't recognize who's being addressed if I was called Charlotte out of the blue. Besides, it's a rather pretty name." Jane squeezed Charlotte's hands before standing, and gently pulled Charlotte up out of the chair by her hands.

Because Charlotte kept her knees together, when she stood up her feet were together. Jane stepped back and observed Charlotte for a few moments, noticing how steady she was standing. It was rather strange that Charlotte should be steady, since she was balancing on the balls of her feet and the tiny two inch heel, and could only do so if she'd worn heels before; it was something Jane had to ask about. Something else struck Jane as being odd, as she noticed Charlotte had her hands together and hanging down in front of her. Just as though it'd been something she'd done her entire life. Standing before Jane was a beautiful fourteen-year-old young girl, there was no longer a trace of Charles Thorton. And there was no way, other than being undressed, would Charlotte be found to be other than a young girl. A young girl who was going to turn heads. Jane took several steps back then said, "Charlotte, walk over to me." She watched as Charlotte dropped her hands to her side and as though she'd done this before, walked over to Jane without so much as a by your leave. Charlotte had taken small steps, without hesitating. She'd been steady with each step, something that shouldn't have happened if Charles had never worn heels before.

Jane was suspicious Charles hadn't told her the truth, and when Charlotte was standing directly in front of her, her voice was anything but kind. "Charles, I believe you haven't told me the truth about not having dressed and acted like a girl before. I believe you've lied to me. None of the boys who came to me in the past have been able to act like the girl I've just watched you portray. You stand as a young girl would as she waited. And you walk in those heels as though you've done that before. I do not tolerate lying by my girls, it's the quickest way to have them sent home exactly as they are dressed. Or not dressed in anything."

When Charlotte had stopped in front of Jane she'd kept her eyes on Jane's eyes, watching as they changed from sympathetic to angry. An anger Charles had seen on the faces of those at Taylor's. An anger which meant his chance of clearing his name could only happen if Jane was on his side. He gave Jane a half smile then said, "Aunt Jane, I've taken self defense and Martial Arts since I was six years old. As I got older some of my instructors, and senseis, felt I could benefit from taking dance, which I did, and it helped with my balance. My standing as I did, was just a ready position when confronted by an aggressive person. I don't look threatening, so I don't give that person a reason to attack me. However, I'm in a position to act if necessary. As to walking in these heels," and Charles looked down at the heels he was wearing, "it's more of my training. Taking large steps puts a person off balance if they should be attacked. Smaller steps keep the body balanced and will allow me to react as needed. I haven't lied to you, Aunt Jane, and I never will."

Jane saw Charlotte's eyes get moist, and told her, "If those tears leave your eyes you will have to redo your face. I am sorry for being rough with you just now, Charles, but I had to know the truth. All of the truth." Jane walked over to the vanity and came back with a tissue, which she gave to Charlotte, telling her, "Blot your eyes gently, don't rub them or you'll smear your eye makeup." When she could see Charlotte had herself under control again she told her to stay where she was and not turn around, as Jane walked over to the closet door and opened it wide. When the door was in position Jane told Charlotte to turn around.

At first, Charlotte was confused as to why she was standing where Jane had told her to stand. But it didn't last as she caught sight of herself in the full length mirror on the inside of the closet door. Or rather, he caught sight of a young girl staring back at her from the mirror. Jane chuckled as Charlotte turned this way and that, all the while looking at the mirror and the reflection she saw. Charles was acting just like a girl would who was making sure she looked good for her night out. Jane chuckled even more as Charles said, "Wow, that's me? All me? I never considered how good I'd look dressed like this. In fact, I don't even see me in that mirror, just a young girl looking back at me."

As Charles continued to primp in front of the mirror, oblivious to anything around him, Jane smiled at what she saw. Charles had taken to dressing as a girl much quicker than others who'd not been given the option, and she knew right then that her plan to clear Charles' name had a chance of succeeding. What she didn't know was how he would react in front of Francis when they started their play acting, and he was punished for his attitudes. She only hoped his balance wasn't only in his posture, but his mind as well.