Twenty Weeks - 1

 

Dr Martin has an opportunity to become Chancellor of one of the most prestigious girl's
prep schools in the country. She's starting mid-year, which causes a problem for her son, Dean.
None of the nearby boys' prep schools will accept a student mid-year.
So... It's only one semester, right? Just 20 weeks?

---

 
Author's Note: This is one of my more recent installments. Again, I want to thank all of you for your lovely comments, especially on a Boy Called Brook! I do have more stories, you know? :) Hint, hint.
This story is more of a character change through realization rather than being influenced by anything else. Let me know what you think about this story, both good and bad.
Please? Leave me a review on this story? I strive towards excellence! ~Clara.
 
This version of Twenty Weeks - 1 has been updated with many corrections towards spelling and grammar.~Sephrena.
 
Image Credit: Image created through the use of ai at https://perchance.org/beautiful-people .~Sephrena.

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Part 1
 

"It is so wonderful to have you here at the Greenwood Academy, Dr Martin," the woman from the school's parent association said as she sipped on a glass of champagne and smiled at the school's new Chancellor. "We were so impressed by how you turned around the last school where you were in charge that we just knew that you were the perfect choice for Greenwood."

The Chancellor, a tall, statuesque woman who always presented herself as a perfectly put together leader, smiled. "Thank you for giving me this opportunity. I am really looking forward to getting to work here. I do wish I'd had the opportunity to start at the beginning of the school year, but starting in mid-year will be a new challenge for me."

"Oh, I'm sure that you're up to it." The woman smiled some more. She looked around the reception as if trying to find someone. "Now, where is this daughter of yours? I've heard so much about her that I feel as if I know her already."

Dr Martin looked about for a moment. "There she is, sulking by the window. The blonde girl in the dark blue dress."

The woman looked to the windows and smiled. "Ahh, yes. It can't be easy for a fifteen year old to move across the country, leaving all her friends behind... I'm sure she'll make lots of friends here, though. A pretty girl like that is bound to be popular."

"Yes, she is lovely." A man from the school's Board of Directors appeared and looked in the same direction. "It is odd that she didn't show up in our background search, Dr Martin. Now, is your son here as well?"

"No," the Chancellor smiled and shook her head. "Dean is staying with his father for the time being. He may join us in the future, though. Deanne was staying with my ex until the opportunity to attend Greenwood arose. I really appreciate you taking her in as a student halfway through the year."

"Oh, our pleasure," the man said. "Her academic record is quite impressive, so we are happy to have her at Greenwood."

Dr Martin sighed. "I do hope that Deedee makes some friends here, though. She was a bit of a loner at her last school."

"Oh, well, let's deal with that right now!" the first woman said. "Let me introduce your daughter to my daughter."

"Oh, thank you, so much." The Chancellor smiled. "Deedee! Deedee, dear. Please come meet some people."

The little, blonde girl in the dark blue dress turned, looking a bit irritated to have been summoned.

The Chancellor smiled, wrapping an arm around the teenager's shoulders. "This is my daughter, Deanne. We call her Deedee."

The two adults said their hellos and welcomed Deedee to Greenwood.

The woman from the parent association looked about for a moment, then spoke to a group of teenagers. "Robin!" the woman called and a good looking girl with impeccably quaffed, long red hair turned and smiled.

"Yes, mom?"

"Come here, dear, and meet someone."

The red head excused herself from her friends and walked quickly to her mother, a huge smile on her face. "Hi," she said as she arrived.

"Robin, this is our new Chancellor, Dr Martin, and her daughter, Deedee, who will be joining your grade tomorrow morning."

"Oh, cool!" Robin smiled at the girl, who was several inches shorter than her and looked a bit younger than most of her classmates. "Come on. I'll introduce you to some of the girls."

Deedee looked at the Chancellor, hoping to not have to mingle with girls in the same grade, but instead, Dr Martin smiled and gave Deedee a gentle, prodding push on the shoulders. "Go on, now, Deedee, and meet your new classmates."

Deedee gave a subtle eye roll, then forced a smile and followed Robin.

"Excuse, me, Dr Martin," an event coordinator interrupted, "but it's time for you to address the people."

"Oh, of course," Dr Martin said and followed the coordinator to the podium.

"Ladies and gentlemen," the coordinator said into the microphone, "I would like to introduce to you, our new Chancellor... Dr Amelia Martin." She stepped aside as the gathered people applauded.

"Good evening," Dr Martin said, smiling broadly, "and thank you so much for such a wonderful welcome to this glorious and historic school. At a time when there are more women than men in the workforce for the first time in history, I am so thrilled to have an opportunity to work with you to offer the young women of Greenwood Academy the finest in same sex education that this country has to offer..."

Deedee was led to the opposite end of the room from the podium where Robin introduced a dozen or so girls by name, but there were just too many names being thrown around for Deedee to keep them straight.

"So, that's your mom?" a dark haired girl said, quietly enough to not attract any attention from the adults.

"Yeah," Deedee nodded. "She's very eager to make a good impression tonight."

"Well, she looks a lot nicer than Mrs Landry, our last Chancellor."

"Where are you from?" Another girl asked.

"San Diego."

"San Diego!?" another girl asked, astounded. "Why the hell would anyone move from San Diego to Massachusetts in the middle of winter?"

Deedee shrugged. "It's not like I had a choice." A scoff escaped Deedee's lips. "I don't seem to have much say in anything anymore."

"No kidding," Robin chuckled. "I can't wait until we graduate and have lives of our own."

"Just two and a half more years," one of the girls smiled.

"... and in conclusion," Dr Martin said from the podium, "let me say that I am very excited to get down to the task of maintaining the excellent reputation of this fine and distinguished institution. Thank you all for this lovely welcome and this amazing opportunity."

"Well, she says all the right things," the first girl who'd spoken said.

"Let's hope she's not a hard-ass like Landry was," another girl said.

"Well," Robin said to Deedee, "is she? A hard-ass, I mean?"

"Only when it comes to me," Deedee said, sounding a bit glum and put upon. "Only when it comes to me."
 

~^~
 

"I hope the move went well," the voice of Amelia's ex-husband came from her voicemail. "Congratulations on your new position. I'm looking forward to hearing all about it. Tell Dean I say 'hi' and that I hope he has a great first day at school tomorrow. I'm off to another assignment in an hour or so. Talk to you soon."
 

~^~
 

"Well, that was a lovely evening, don't you think?" Dr Martin said as they entered the big foyer at the front entrance of the Chancellor's house on the campus of Greenwood Academy.

"I guess," Deedee said, sulking and hanging up a winter coat in the hall closet.

"You guess?" Dr Martin shook her head. "Are you just going to sulk about for the entire semester?"

Deedee let out a huge sigh. "Mom... you made me move all the way across the country, away from nice, sunny, warm San Diego to this remote, freezing cold place. I know no one here and then there's..." Deedee used both hands to indicate the dress.

Dr Martin shook her head and folded her arms. "Alright, we've been through this a hundred times. If there was another way of getting you an Ivy League preparation education somewhere else, I would have enrolled you there, but moving in the middle of the school year made that impossible."

"Mom, there is a perfectly good public high school in this town..."

"Perfectly good for someone who wants to go to a public college. Honey, that school has an average or below rating for every important standard."

"A private school, then, mom. Anything would be better than this."

The Chancellor shook her head. "The only boys' schools in this area that even come remotely close to the standards of Greenwood are St John's and St Mark's and neither is accepting students mid-year. I've explained that to you at least fifty times, Deedee..."

"Could you please just call me Dean when we're alone!?"

"NO!" Dr Martin said, emphatically. "Deedee, for the next twenty school weeks, you are not my son. You are my daughter, Deanne and that is that, AND this is ABSOLUTELY the last time that we shall have this conversation. Have I made myself abundantly clear, young lady?"

Dean shook his head and bit his lip. "And when this school year is over, you'll let me attend the computer gaming competition in Las Vegas?"

Dr Martin nodded. "With me as a chaperone, yes."

Dean nodded. "Ok. Then I'll play this dress-up game, but only until the last day of school. Then Deanne moves back to California to live with her dad and Dean shows up to live with you."

"That's the deal." The Chancellor nodded. "Are we on the same page, then?"

A second or two passed before Dean nodded. "Yes, ma'am."

Dr Martin gave her son a hug, then stepped back and moved his blonde hair behind his shoulders. "I know this may not be exactly what you want to hear, but you actually make a very attractive young woman."

Dean smirked and shook his head just a little. "Thanks... I guess."

His mother smiled. "You'll see... the time will fly past. Twenty weeks isn't all that long. It'll be over before you know it."

"I doubt that, mom. I truly doubt that." He laughed and smiled.

She kissed his forehead. "Now, go get out of that dress and into your pjs..."

"You mean nightgown."

"... and meet me in my room. I'll braid your hair before you go to bed. It holds a nice curl all day if you sleep in braids."

Dean shook his head and walked up the stairs. "That is definitely NOT something a mother should ever say to her son."
 

~^~
 

"Are you ready?" The Chancellor yelled up the stairs the next morning. "Come on, I don't want to be late."

Dean stomped down the stairs, not looking at all happy. "Mom... first off, the students don't have to be at the school for nearly another hour. Second... look at me. I look like a moron in this get up."

He was wearing the school's required uniform. A white, long sleeved blouse that puffed up around the tiny cuffs at his wrist and had a soft, little collar that allowed him to wear the navy blue, criss-cross-bow tie, and it had tiny navy blue buttons up the front. Beneath that was a padded bra that gave him a very modest bust. The blouse was covered with a gray-blue and navy blue checked jumper-style dress that also concealed the pink, star adorned panties that he wore that morning. Below that his legs were supplied with plain white, knee high socks and patent-leather, high gloss, two inch heeled, rounded toe shoes with a narrow strap that ran around his ankle and buckled to fit tightly.

"You look lovely." The Chancellor smiled. "And more importantly, you'll look just like all the other girls."

"The other girls." Dean shook his head.

"Yes, the OTHER girls," his mother insisted. She fussed a moment with his hair. "You look perfect, Deedee. You really do. Even with no makeup on, no one would ever think that you were anything other than a normal sophomore at a high end prep school."

She played with his hair a bit longer. "Who would have thought that being petite would be such a benefit to a boy?"

"Yeah, well, I looked like a boy until you started in on me. No one can have their eyebrows plucked, their body hair all removed and their ears pierced and still look like a boy. And look at this hair, mom!"

"Alright, now stop. Your hair was that long before we started all of this."

"This long, yeah, but not sculpted this way and certainly not this light in color. That woman at your salon cut it so that it actually looked like I had more hair than I had before I started , then dyed it so I look like I had spent months on the beach. Mom... I'm a completely different person than I was three weeks ago!"

"That's right, my love. Now... let's get to school."
 

~^~
 

Dean met at least thirty older women that morning. Teachers, teachers' aides and office personnel. He just smiled a lot and nodded at each woman in turn, trying hard to connect faces to names. Several even mentioned that they were thrilled to have him joining their classes. The only woman who stood out was the Assistant Chancellor, Mrs Olsen, a woman in her late fifties or early sixties who seemed genuinely interested in Dean's life, asking questions about his life in San Diego and his aspirations later in life. She seemed very pleasant and caring. Dean liked her immediately.

"Hey," a voice said from the doorway to the office. "You want to come with me and meet some of the girls?" It was Robin, the red headed girl from the reception the previous day.

"Oh..." Dean said, nervous to begin his tutelage at this haven of females. "... I think my mom wants me to wait here until school actually starts."

Robin scowled at that. "Oh... ok... I'll see you in class... I guess."

"Oh, hi, Robin," The Chancellor said, smiling and exiting her office with a handful of paperwork.

"Hi, Dr Martin," Robin replied. "I was going to show Deedee around, but she says you want her to wait here."

"She did?" Dr Martin looked at Dean and made a confused face. "Why would I want you to do that. Go on and get to know some new people." She kissed her son's soft cheek and continued on with her office work. "You go have a good first day, now, Deedee."

Dean shook his head and started to walk around the counter.

"Oh, sweetheart," Dr Martin said with a smile. "Don't forget your purse." She help up a smallish handbag with a shoulder strap attached.

Dean reached back and took the feminine accouterment from his mother. "Thank you, mother," he said in a saccharine voice.

"You'll have to leave that in your locker," Robin whispered as they walked down the hall. "Your homeroom teacher will assign you one. What's your first class?"

Dean looked at his schedule. "Umm... Ms Cohen for Civics."

"Oh, cool," Robin said enthusiastically. "That's MY homeroom. Let me see your schedule." She half-snatched the paper from Dean and read it. "Hey! Your schedule is identical to mine... except Phys Ed. How come you're not taking Phys Ed?"

"Oh, I have pretty bad asthma," he lied. "I have a medical note about that. I do take some training classes outside of school, though. Mostly Pilates and gymnastics."

Robin nodded. "Huh. For a moment there I thought that you were going to say you took dance or something. That would have been weird."

Dean wanted to let that go, but he was curious. "Why weird?"

"Oh, I don't know... I guess I just thought you were... kinda... a tomboy, if you know what I mean."

"A tomboy?"

"Yeah... I mean... and I don't mean to be hurtful at all... it's just that you looked a little... uncomfortable... all dressed up yesterday."

"Well, that's true," Dean laughed.

"So... are you? A tomboy, I mean?"

"Like do I play sports and stuff?" Dean asked, confused. "I just told you that I have asthma. No, I don't play sports?"

"No... I mean... what team do you play for?"

"Team? I don't play sports. I just said that."

"No," Robin laughed. "I mean... do you like boys or girls?"

"Oh. I... don't really... date."

"I didn't ask if you dated," Robin laughed out loud. "Gosh. Have you ever had a conversation before?"

"Not like this one," Dean laughed too. "Are you always this forward when getting to know someone?"

"Yeah, of course. If you're into girls, then I can guide you in the right direction, that's all."

"Are you?"

"Am I what? A lesbian!? Oh, God, no!" She was belly laughing, now. "I'm the opposite of a lesbian. My mom says I'm completely boy crazy! I have been dating since I was in seventh grade, but I don't have a boyfriend right now! If you want me to set you up, though..."

"No, no," Dean said, a bit too quickly. "I don't think I'm really... ready... for dating."

"Ok," Robin smiled. "If that changes, let me know."

"Hey, guys!" It was the first girl to have spoken in the group of girls the previous evening.

"You remember Jade, don't you?" Robin assisted.

"Oh, yeah, hi," Dean said as they all continued down the hallway.

"Wow, look at that uniform," Jade said. "Crisp and stiff. I hate them like that." She laughed at what she'd just said.

"Be nice," Robin said to Jade. Then she looked at Dean and said, "Don't worry. After it's been washed a half dozen times, it won't be itchy any more."

"Then you can wear it without a slip," Jade agreed.

"A slip?" Dean asked. He was moderately aware of the garment, but that was all.

"Yeah, a slip?" Jade laughed. "Don't tell me you're not wearing a slip under that?"

Dean shook his head.

"Oh, God, you're going to be so itchy by the time you get out of that! It's wool!" Jade was laughing, but there was some sympathy in her voice.

"You are," Robin agreed. "Maybe they'll let you run home and put one on before school starts. Your house is just across the drive, right?"

"Yeah, but I don't own a slip," Dean admitted, not sure of how that would be received.

Jade looked at Robin with wide 'can you believe this' eyes. "How can a girl NOT own at least one slip?" Jade asked, laughing.

"I don't think Deedee wore dresses much before she got here," Robin offered as an excuse.

"Not at all," Dean confirmed.

"Well, that's going to change if you hang around this place," Jade said with a chuckle. "It's rare that we're allowed to wear slacks."

"Great," Dean said, shaking his head.

"Oh! I have an idea!" Robin said, excitedly. "Come on! Let's go see Ms Highland. I bet she has a slip you can borrow."

"Ms Highland?"

"Theater teacher," Jade explained. "She has a huge costume room. She probably does have something you can borrow."

By now, Dean was being pulled hurriedly to the theater. "No. That's ok. I'll be fine."

"No you won't," Robin insisted. "By three o'clock your legs will be red and irritated. You need this."

They reached an office door and Robin knocked on it. "Come on in," came a voice from inside. The rather broad, but confident woman looked up and smiled. "Good morning, girls!" She greeted them. "Ahh... I am assuming that this is the new girl. Welcome. I'm Ms Highland."

Dean shook her hand. "Deedee Martin."

"Ms Highland, we have a problem," Robin explained. "Deedee is wearing a brand new uniform and didn't know that she needed a slip under it. Do you have one she could borrow for the day?"

The teacher gave Dean an appraising look. "I think so. Size two, I'd guess. Right?"

"Umm... yes... I think so," Dean said. He'd not paid a lot of attention to his new sizes, but that sounded right.

Ms Highland disappeared into a storage area, but kept talking. "Tell me, Deedee, were you involved in the theater department at your old school?"

"Not really," he admitted. "I was in some plays in middle school, but nothing in high school."

Ms Highland reappeared carrying a piece of beige nylon folded nicely. "Well, here's the deal: I'll give you this half-slip, which you will find that you need for at least a few washings of that jumper, but only if you agree to audition for the spring musical."

Dean looked a bit scared. "Oh, I don't know, Ms Highland. I mean... I just got here and I'm sure that I'm going to have..."

"Irritated legs," the woman interrupted, "unless you wear this under that jumper. What do you say?" She had a playful smile on her face, but Dean could tell she meant business.

He sighed and said. "Ok. I'll audition."

"Excellent," Ms Highland smiled and offered the little, folded item to him. He just stared at it for a moment, not knowing what to do. Finally, the teacher sighed and said, "Oh, for goodness sake. Turn and face the wall."

He did as she instructed, and was shocked when she knelt behind him and reached around to open up the top of the half-slip in front of him. "Go on. Step into it."

He lifted one foot and then the other, slipping his shoed feet carefully into the elastic waist opening. Then, very quickly, the teacher raised the slip up his legs and settled the elastic opening on his waist. She hardly raised the uniform's skirt at all, and he was facing away from everyone, but he still felt extremely exposed by what had taken place.

"There," Ms Highland smiled as she stood and straightened his skirt. "That will feel a lot better."

What it felt was... odd. It was very soft and silky around his legs and nethers, which were just getting used to the softness of the cotton panties his mother had forced him to wear for the past ten days. Even standing still, the feeling was odd and exciting. When he moved to turn around, the feeling of the garment was nearly overwhelming. He looked about the room at the woman and the girls that surrounded him and prayed that his most unfeminine attribute would stay calm and tucked away between his legs.

"Thank you, Ms Highland," he muttered, feeling both excited and a bit violated.

"You are welcome, Deedee. Now, remember, auditions are Thursday, after school, in the auditorium." Ms Highland checked the time on the wall clock. "You girls should get to homeroom. It's getting close to first bell."

"Thank you, Ms Highland," both Robin and Jade said as the each grabbed an arm and towed Dean out of the theater teacher's office.

"Just a second," Jade said, stopping for a moment. She reached into her pocketbook and pulled out a tube of lipstick. She opened it and looked at Dean. "Let me put a little of this on you."

"What!?" Dean was trapped between Jade and the wall. "The handbook says 'no makeup.'"

"Yes it does, but everyone wears at least a little lipstick. This is shade is called 'nude.' It won't be all that obvious. Most of us wear some powder and eyeliner, too. The teachers know that it's part of being a teenaged girl and look the other way. Now, stay still." Jade grabbed his cheeks and forced his lips to open just a bit so she could smear the lipstick neatly onto his lips. She wiped it in several long strokes, followed by a dozen or more little strokes until she was satisfied. "There. Now, you'll fit it. I'll meet you in the girl's room after second and I'll see if I need to reapply it."

Before Dean could reply at all, Robin grabbed his hand and pulled. "Come on. We don't want to be late."

Before he knew it, Dean was being introduced to a middle aged woman with short hair and a mean looking stare. "So, you're the new girl, huh?" The teacher said with a bit of a snarl. "Well... you've got a lot of catching up to do, that's for sure. What do you know about the process of impeaching a President of the United States?"

Dean stared at the woman for a moment, not sure what to say.

"Well? Speak up, girl. What do you know about the process of impeaching a President of the United States?"

"Nothing, Miss," he finally admitted.

"Wonderful," the woman shook her head. "Well, sit down in the third seat in the second row. Have they issued you your laptop yet?"

"No, Miss," Dean replied. "I think they were going to send it to my homeroom this morning."

"Well, we can't wait for 'them' to do their job, now can we? Robin, show her where to sit. Jade, go to the media center and ask for her laptop. I'm not going to have her sitting here wasting her time. She's here to learn and that's what she's going to do." Then she looked at Dean and scowled just a bit. "My name is Mrs Cohen, young lady, and please don't forget it. Being the Chancellor's daughter isn't going to cut you any slack in my classroom. Understood?"

"Yes, Mrs Cohen," Dean replied as he moved to his seat. "I'm sorry if I upset things. I didn't mean to."

The teacher just shook her head and walked out into the hallway to monitor the activity out there.

Dean took a seat at the assigned location, neatly folding the uniform's skirt under his rump as he did so. He took a deep breath and then took note of the odd sensation of being in a classroom dressed as he was and with his lips feeling almost heavy with lipstick. 'Twenty weeks,' he thought. 'Five school days a week. That's about one hundred days. That's all. Just one hundred days and this was day one. I can survive a mere one hundred days.'

"Don't worry," Robin whispered as she took the seat next to Dean. "Her bark is much worse than her bite. She's actually kind of nice, once she gets to know you."

Dean nodded and looked around the room at student projects on the walls and shelves and he was impressed. These projects weren't just the simple poster board projects he'd seen at his old school. These projects were well researched and very professionally presented. The bar for success was obviously much higher here.

"Here you go," Jade said as she placed a laptop onto Dean's desk. "Just log-on with your student number and you'll already have access to all the classrooms."

"Thanks," he nodded and opened the new laptop. He signed into the computer, changed his password and opened the classroom page for Civics. He read the lesson plan for that day and his eyes almost crossed. He knew all those words, but he didn't understand what they meant in that particular context. He had never taken a class like this before.

"Good morning, girls," Mrs Cohen said loudly, calling the class to order. "I'm sure you've noticed a new face in the classroom. Stand up..." she checked her attendance sheet, "...Deanne and introduce yourself."

A little confused, Dean stood and said, "Umm... hi... I'm Deedee."

He went to sit back down, but the teacher stopped him. "And where are you from, Deanne?"

"Deedee," he corrected, not loving either name, but at least Deedee was simpler.

"What your friends call you is up to them, Ms Martin, but I am not your friend. I am your teacher and I will call you by your legal name."

"Yes, ma'am. I'm from San Diego, California."

"Alright," Mrs Cohen said. "Have a seat and we'll begin."

The next fifty minutes was a blur of a subject about which Dean only had a passing familiarity. He was not at all sure that he could get caught up and pass this course, but Robin assured him that she would help him any way should could.

Next came algebra, a subject he at least had done well in at his old school. He decided that this class was at least possible to pass. They were a little more advanced than his old class, but he understood what was being said. I just needed to catch up.

As class ended, Jade slipped her arm into his and said, "Come on. We've only got a few minutes before Phys Ed and I need to touch up your lips."

"I don't have Phys Ed," Dean remarked.

"Yeah, well, I do, so hurry."
 

~^~
 

"Come on in," Dr Martin said when Dean knocked on her office door. She smiled at her son in his pretty uniform. He looked so nice in it. Much nicer than the jeans and tee shirt he wore to his old school. "So... how's it going?"

"Ok," he said, a bit sadly. "Civics looks tough... like I have a lot to learn, I mean. Algebra was fine. I can catch up there."

"Good, good," his mother smiled, but then her eyes narrowed a bit. "Are you wearing lipstick?"

Darn rolled his eyes and nodded. "This girl - Jade - she put it on me. She said that all the students here wear a little makeup and I looked out of place without the lipstick."

"Huh," the Chancellor thought for a moment, "now that you mention it, I think she might be right. I hadn't noticed it, but almost all of the girls are wearing just a little. It looks nice on you."

"Thanks," he shook his head. "So... I'm supposed to be an office aid this period while the rest of my class does Phys Ed. Does that mean I help you?"

"I'm going to say 'not usually,' but right now I do need some help. See that pile over there?" She pointed to a small side desk. "Those are financial reports and they are a mess. I need you to go through them and put them in chronological order. The dates are at the top. Can you do that?"

"Sure."

Dr Martin watched as her son took the seat, smoothing his uniform dress beneath him. She knew that she was asking a lot of him, but she was honestly shocked by how good he looked and how well he had acclimated to feminine movement and behavior. Maybe this wasn't all that fair to Dean, but it certainly was a teachable exercise. He would definitely come out of this experience with a new outlook on life.
 

~^~
 

The last period of the day was labeled as 'Conservatory' on Dean's schedule. He had no idea what that meant, but he followed Robin and Jade down the hall and into the school's smallest theater - it had three. There he saw the teacher who'd given him his slip earlier in the day inviting all the students to sit cross legged on the stage.

"Come on, girls," Ms Highland said in a big voice while she was clapping her hands. "Sit, sit, sit."

When all the students were seated, Ms Highland began her lesson. "So, your homework for last night was to watch the first act of the Broadway production of 'Into The Woods' that I put into your online classroom. Did anyone NOT watch act one?"

The word 'not' was said in such a way as to indicate that Ms Highland expected that everyone had watched the homework. Still, Dean had no choice but to raise his hand.

"That's ok, Deedee," she smiled. "You can watch act one tonight, then we'll be watching act two on Tuesday in class."

"Yes, ma'am," Dean nodded.

They went on to discuss the pros and cons of Stephen Sondheim's popular theater piece with all of the girls giving incredibly well thought out critiques of the piece, the actors, the music, the singing, the set, the lighting, the costumes... every aspect of the production was under discussion.

Dean was fascinated by the passion of the girls' responses and how they defended their opinions with words, rather than emotion. Ms Highland was like an orchestral conductor, keeping the conversation going and on track so well that the class flew by and Dean was surprised when the teacher said, "Alright, that's all for today, but before the end of the day, I just want to remind you all that Thursday is audition day! Remember, I want all of you to audition for the spring musical. 'Chicago' is a very 'woman heavy' script with lots of roles for women. The boys from St Mark's and St John's will be auditioning for the male parts, I'm sure."

"And for the chance to paw us," Jade whispered.

"Shh," Robin whispered and giggled back.

"So," Ms Highland continued, "make sure that you are familiar with the show and that you have a song prepared. I'm sure that Mrs Tracy would be willing to run through your audition piece ahead of time if you talk to her. If you don't prepare a song ahead of time, Mrs Tracy will teach everyone a little of one of the songs from the show and you'll have to sing that by yourself when your name is called. Doing it that way is fine, too. Questions?"

One girl raised her hand and when she was called on, she asked, "All the upperclassmen are going to get the leads, right? So, can we just audition as dancers?"

The teacher smiled. "To answer your first question, No, the upperclassmen will not necessarily be cast in the leads. I know it might seem that way, but usually there are only a few women's roles and the older girls have the advantage of experience. This year, there are lots of women's roles, so prepare your audition well and we'll see how the cookie crumbles. To answer your second question, No. The point of this class is to prepare you for the real world of theater, even if you never live in that world. So, if you audition, you do it all. You sing, dance and you act and if that makes you uncomfortable, then that means I'm doing my job well." She smiled at the students and then said, "I think that about wraps up the period..." a bell interrupted her, "... have a good day, girls! See you tomorrow."

As Dean walked down the hallway to his locker, he was surprised that so many girls not only said goodbye to him, but they also recalled his name, which was more than he could say about himself. Were they just being nice because he was the child of the new Chancellor, or were they being nice because they were... nice?

Most of the girls, including Jade and Robin, hurried to the front of the school in order to be picked up, while some went to sports practices or club meetings. Dean had nothing to rush to, though. He meandered to the main office and knocked on his mother's office door.

"How did it go?" She asked, standing and coming to the doorway to hug him - a very unusual thing for her to do.

"It wasn't as bad as I expected," he sighed as his mother played with his hair a bit. "The classes are really challenging, so that's a good thing, and the girls are all pretty nice."

Dr Martin smiled. "I saw you with the same two girls several times. Did you make some friends."

"I think I might have," he smiled, the lipstick making the smile all the brighter.

"Oh, good," she said, patting his cheek - again, a very unusual thing for her to do. "Listen, Deedee, I need to put in a few more hours here, why don't you go ahead back to the house and do your homework. If I don't get home before five, you go ahead and fix yourself some supper. Ok?"

"Ok," Dean said.

"Give me a hug," Dr Martin said, putting her arms around her little son.

Dean wrapped his arms around his mother as well. "Who are you and what have you done with my mother?" He teased.

"What do you mean?" She asked as she hugged.

"I mean... in fifteen years, you've never once played with my hair, rubbed my cheeks or hugged me before I walked home. What gives?"

She chuckled. "I don't know. I guess it's just different when you have a daughter. I feel more inclined to hug you when you're my little girl."

"Ok, enough of that," Dean laughed and pushed her off of him. "I'm not your daughter, mom. Remember that."

"You keep telling yourself that, Deedee, but when I look at you, I don't see a boy at all. You're just too, too cute."

"Yeah, well... I'll see you at home." Dean grabbed his jacket and headed out into the cold Massachusetts air for the short walk back to his new home.
 

~^~
 

"I'm home," Dr Martin called as she entered the house.

"In the kitchen," Dean called back.

She entered the kitchen to find her son standing at the counter, his computer open, papers spread around the counter. She could only see his upper body from where she stood, but he was wearing a San Diego Padres long-sleeved tee shirt that fit him rather snugly around his padded bra. A voice was coming out of his phone, which was propped up against a glass of water.

"... so if you read chapter twenty one and do the questions at the end of it, then Mrs Cohen will probably be satisfied that you're trying to get caught up."

"Ok. Great," Dean replied. "My mom's home, so I should probably get going. I appreciate all your help."

"Hey, no biggy," the voice said. "Is your mom in the same room?"

"Yeah."

"HI, DR MARTIN!!!" The voice shouted.

"Hi!" Dr Martin replied, walking around the counter. "Who am I talking to?"

"It's my friend, Robin."

The Chancellor looked into the phone's screen and waved to the red haired girl on the screen. "Hi, Robin. Thank you for helping out my daughter."

"No problem, Dr Martin. Any time."

"Thanks again," Dean smiled and waved. "I'll see you at school tomorrow."

"Cool. Bye-bye." Robin waved back and ended the call from her end.

"Your friend?" Dr Martin asked. "That's encouraging."

Dean blushed a little and shrugged. "I guess. I mean... she's very nice and very supportive and she called me to see if I needed any help. At first I thought that she might just be being nice to me because I'm your... kid... but she was really nice and made me laugh a lot. She also stayed on the phone with me for almost an hour and a half. That seems like she actually likes me."

"And do you like her?"

"Yeah. Sure."

"Ok." Her eyes narrowed a bit. "But... you don't... LIKE-like her, right? I mean... you're not falling for her, are you? Because that could cause some problems."

Dean started gathering some of his papers as he let put a snicker. "Yeah. That COULD cause some problems, but don't worry... I'm not 'falling' for her. She's just my friend. Just like Mable was back home."

"Uh huh..." his mother smiled. "Well, whether you want to acknowledge it or not, Mable had the hots for Dean."

"No she didn't, and stop talking about 'Dean' in the past tense, as if he's never coming back, because he is."

"Alright... now, with that in mind, can we discuss this outfit of yours?" She indicated how he was dressed, which was the Padres shirt on top, but down below he was wearing a very lacy, beige slip that was thin enough to allow the star decorated panties beneath to show through and the thin nylon. Below the slip were the white socks he'd worn to school. "It's an interesting dichotomy. Tomboy on the top and girly-girl on the bottom. I like it, but I don't fully understand it."

Dean rolled his eyes. "I had run up stairs and was taking off my uniform when my phone rang. So, I grabbed this shirt off my bed and pulled it on. Then I carried the phone down here so I could work with Robin. Then you came in. End of story. No dichotomy or anything symbolic going. Ok?" He turned and walked away to put his computer and homework into the backpack he'd pulled out earlier to use for school.

Dr Martin smiled at both his defiant answer and his girlish appearance. "You know, I don't recall buying you that slip, and, considering how adamant you were about getting the plainest bras at the store, I am a bit surprised to see you wearing so much silk and lace. It's not very macho, after all."

Dean looked down at the slip, which he'd kind of forgotten about. The top half, from the waist to the halfway point, it was plain, beige, shiny material, but from that point down, it was very sheer and lacy.

"Well, I don't think it's actually silk... Nylon, I think, but YOU didn't consider what wearing a brand new, itchy wool jumper all day might be like. My new friends did and they brought me to see Ms Highland who gave me this from her costume room."

"GAVE it to you? She doesn't expect it back?"

"Nope. She said I could keep it as long as I auditioned for the spring musical."

"Oh?" The Chancellor laughed a little. "Do you know what the spring musical is?"

"Umm... I think it's called 'Chicago' or something."

"That's right. And have you ever SEEN 'Chicago?'"

"No... why?"

His mother shrugged, innocently. "No reason. I suggest you watch it before you audition, though. You may find it... eye opening."

"I'll try," he said, shaking his head, "but I'm already buried in work. Tonight, I have to watch act one of a Broadway production of something called 'Into The Woods." You want to watch it with me? It's on my Conservatory classroom, but I can link my computer to the TV."

"Sure. Let me grab something to eat. Have you had supper?"

"Yeah. I made some Ramen before Robin called and ate it while we talked."

"Ok. Let me grab a little salad and I'll be right in."

She grabbed a bag of pre-made salad and poured some into a bowl, then added some dressing and a few croutons before grabbing a bottle of water and a knife and fork and walking into the TV room where Dean, still dressed as he had been, was sitting on the couch and calling up the assigned viewing.

They sat in silence, watching the filmed version of the Broadway production. Eventually, Dr Martin said, "I've always loved Bernadette Peters. She's so pretty and has such a great voice."

"Which one is she?"

"The witch."

"Oh... yeah, she is pretty, now that the wig and makeup are gone."

She glanced over at her son and saw that he was kind of huddled into the corner with his arms crossed. "Are you cold?"

"A little."

She got up and pulled a large blanket out of a trunk in the corner, then came back to the couch, sat and spread it over her legs. She held up the side and said, "Come on over here next to me. We'll cuddle for warmth."

Dean got up and moved next to her, sitting against her, pulling the blanket over him as well.

Dr Martin put her arm around her son's small shoulders and pulled him close so that his head rested on her breast. She kissed the crown of his head and smelled the flowers in his shampoo and hairspray. It was odd. Dean probably would never cuddle like this, but Deedee was different. She seemed... just different, that's all. And that was kind of refreshing. Dean was standoffish and sarcastic. Deedee was... well... a girl. And that was kind of nice... for as long as it lasted.
 

~^~
 

Tuesday morning went, pretty much, without a hitch. Dean thought less about his clothes than he had the day before and he was able to relax a bit more since no one saw him as anything other than another girl. He did work hard to try to memorize names so that when a girl spoke to him, he could reply using her name.

Mrs Cohen was actually impressed that he had taken the initiative to do some work to get caught up in Civics class and she even complimented him. "Well done, Deanne. Very well done." Then she winked at him. "Perhaps there hope for you, after all."

Last period, Conservatory class, was even better than the day before because he was able to join in the conversation, and act two of 'Into The Woods' turned out to be completely unexpected and really surprised him. He actually loved it and found himself sniffling back some tears a few times.

"Two day warning," Ms Highland said as the class started winding down. "Remember, auditions right after school on Thursday! I can't put on a show without you, so get your pretty butts into the auditorium as quickly as you can. I expect a big turnout for this one."

When the bell rang, Ms Highland called out, "Oh! Deedee, please stay for just a moment."

"We'll wait by the door," Robin said as Dean walked over to speak to his teacher.

"Yes, Ms Highland?" He asked, politely.

The teacher smiled. "How's it going, Deedee?"

"Oh... umm... fine, I guess, Ms Highland," he replied, surprised by the question.

She nodded, then sighed and crossed her arms around her midsection. "Look, Deedee, I know I put you on the spot yesterday morning when I kind of demanded that you have to audition for the musical. I shouldn't have done that, but... Deedee, you've come here from a very popular, trendy city and we're... well, we're kind of isolated out here in the sticks and that goes double for you. All of the girls leave the campus and go home every afternoon while you are kind of stranded here on campus - which is even more remote than the rest of the town. Do you understand what I'm saying?"

"Not really, Ms Highland."

The teacher shook her head. "No... of course not. My point is, Deedee, that the musical will give you an opportunity to be amongst your peers in a more casual, friendly and creative way than a normal school day would offer." She smiled. "I just think... it would be good for you to be involved. So... please... audition."

Dean smiled at his teacher's stammering. "Ok, Ms Highland. I will."

"Have you acted before, Deedee?"

"I've been in a few school plays, but that's all."

"Well, that's a start? Do you sing or dance?"

"I mean... I sing along with the radio, but that's about it, and anyone can sound good singing along with Taylor Swift. I've never danced, though. I did gymnastics from the time I could walk until we moved, but that's about it."

Ms Highland smiled. "Also good starts." She patted Dean's shoulder. "That's all I wanted to say, Deedee. I just didn't want you to feel like I was forcing you to audition." She snickered a little. "I guess I'm just trying to guilt you into auditioning instead."

Dean laughed. "Yeah... I guess."

"What was that all about?" Jade asked.

"Nothing, really," Dean smiled. "She just felt bad that she made me promise to audition in exchange for the slip she gave me yesterday."

"You are auditioning, though, right?" Robin asked, almost panicked at the thought of Dean not auditioning.

He shrugged. "Sure. I guess so."

"Good," Jade said, sliding her arm under Dean's and leading him down the hall. "Now, let's talk about something really important. What are you doing Friday night?"

A bit surprised by the change in subject, Dean said, "Nothing. Why?"

"Because Robin and I are going to see that new spy movie at the cinema down in the city. Want to come?"

"Sure!" Dean replied, a bit excited at seeing the high budget, blockbuster. "I'll need to ask my mom, but I think she'll let me go."

"Cool. My mom will be driving. We'll pick you up around five thirty."

"Great!" Dean smiled.

"Tell her the rest," Robin said.

"The rest?" Dean asked.

"Ok..." Jade smiled. "We'll be meeting some other kids there."

"Oh," Dean shrugged. "That's ok. Are they girls from Greenwood?"

"No," Jade smiled. "They don't go to Greenwood..."

"Oh, for crying out loud," Robin said, impatiently. "They're boys, Deedee. We're meeting up with my cousin, Willie, and his friends. They all go to St Marks. It'll be the three of us and five of them."

"Oh..." Dean was suddenly hesitant. "Are you guys... dating these guys?"

"Oh, God, no!" Robin laughed. "Willie and I were brought up like he's my twin brother or something, and the other guys are all just his buddies. We meet them at the movies a lot. Our moms don't like us going into the city alone, so Willie and his friends are kinda like our chaperones. That's all. I just felt like you needed to know."

"Oh... ok..." Dean was not at all certain if this was good idea anymore.

"Oh, come on!" Jade laughed. "Don't wimp out on us just because there will be boys there! Come with us."

Dean must have looked a little pale, because Robin said, "I think we scared her. Honest, Deedee... they're nice boys and we always have fun with them, but they're just boys."

Dean put on a brave smile. "Ok. Let me talk to my mom."

When they reached their lockers, they each took their winter coats out of their lockers. "Yikes!" Robin said, looking at her phone. "My mom's outside and she's not happy that I'm keeping her waiting. Gotta run! Love you guys! Deedee, I'll call you in an hour or so to check on your homework."

"Bye!" Both of them replied.

"I should go, too," Jade said. "I'm not even going to look at my phone, because I know that my mom is probably ticked off, too, and I don't want to deal with it. You're coming Friday, though, right?"

"I'll ask my mom."

"You're coming, though. Have your mom call mine if there's any problem." She waved and hurried down the hall.

Dean waved, then sighed. "Great," he muttered. "Just great." How had his life gotten so complicated? He really liked these girls and he wanted to be their friend, but... just eighteen days ago, Dean had been just a regular guy. Small and scrawny, yeah, but pretty much, a regular kid. Then, out of the blue, his mother announced that she had a great job opportunity on the other side of the country.

"It's a great opportunity, Dean," she had said at the dinner table at their home back in San Diego. "It's a lot more money than I made at my last position, a chance to lead one of the most prestigious schools in the country and they'll provide us with a house - a big house. I know that leaving mid-year isn't ideal, but I really can't say 'no' to this."

Dean had nodded. He certainly understood why she wanted to take the job, but he really didn't want to go live in Massachusetts. It was cold there and the school seemed really old and stodgy. He didn't want to leave warm, hip San Diego.

"Ok," he'd said to her, "I get it, but... would it be possible for me to stay here and live with dad?"

His mother had let out a big sigh. "I don't think so, Dean. I spoke to your dad and he's traveling even more for work now than he was when we were married. It just wouldn't work out. I'm sorry."

There wasn't a lot left to discuss, then. Dean was only fifteen and his mother had been out of work since the end of the previous school year. Her idea of being an educational consultant hadn't worked out all that well and this job seemed pretty awesome.

"Ok... so... if this is an all girl's school... where will I be going to school?"

Two days later, his ears were pierced, his eyebrows plucked, what little body hair he'd had was gone, his hair had been treated, colored and styled and his Aunt Melissa, his mother's best friend who also happened to work in the lingerie department at a local store, was fitting him for a padded bra and providing him with a 'fun selection of panties.' At first he thought his life was over, but since then he'd kind of gotten used to this new life of his. Yeah, the clothes were very different and a lot higher maintenance, but they were also a lot softer and kind of interesting... no... that wasn't the right word. They were kind of... wonderful... to wear. In fact, now that he was a few weeks into acting like a girl... he was actually kind of enjoying it - especially now that he had some friends.

Now, though...

...boys.

He'd hoped that, being at an all girls school, other boys wouldn't be a part of his twenty week life as a girl. Now... they might just be. "Ugh..." he muttered as he headed to his mother's office.
 

~^~
 

"So, what did she say!?" Robin asked, excitedly, as they FaceTimed.

Dean was still in his uniform while he could see that Robin was wearing a hoodie and pajama bottoms. "She said she'd think about it and we'd talk about it when she got home."

"Seriously, though, Dee, they're good boys and they're all very nice. Nothing would happen."

The microwave started beeping. "Keep talking," Dean said, "I have to grab my popcorn."

"Tell her that Willie is my cousin and he wouldn't let anything happen to us. He's like my own personal body guard."

"Yeah, I know, but you know how mom's are," Dean called from the microwave. He pulled open the top of the single serving bag and pulled his head back to avoid the heat rising from the bag. "I've never gone out on a date or anything before."

"For crying out loud, it's not a date, Dee. It's a movie. Just tell her to pull that stick out of her butt and let you go."

"Whose got a stick up her butt?" Dr Martin asked, entering the kitchen.

"Oh, no!" Robin shrieked. "Dr Martin, I didn't mean that! We were just talking..."

Dean's mother looked at her son with a 'what's this all about' look on her face. "Talking about what?"

Dean sighed. "The movie Friday night," Dean said loud enough for his friend to hear, while simultaneously indicating to his mother that he wanted her to say 'no' by pretending to cut his own throat with his forefinger.

The Chancellor squinted at her son and finally said, "Oh... the movie..." She still sounded a little confused. "I guess that Deanne and I need to talk about that before I make a decision."

"I understand," Robin said, imploringly, "but, Dr Martin, I swear they are nice boys. Nothing will happen. We're just going to see a movie and maybe have an ice cream or a burger afterwards. I promise, Dee will be as safe with us as she would be at home. Please let her go."

Dr Martin eyed her son with suspicion. "I'll tell you what, Robin, let me talk to my daughter about this and she'll get back to you later."

Dean ran over to the counter top and stuck his face into his phone's camera. "I'll call you back later, Robin... or maybe talk to you tomorrow in school, ok?"

"Yeah, ok," Robin said, then quietly continued, "I'm sorry that I said that about the stick."

"Uh huh," Dean said, glancing at his mother. "That's ok."

"Alright," Robin said. "Love you, Dee. See you tomorrow."

"Love you, too," Dean said. "I better hang up." He pushed the 'end' button and the call completed.

He looked at his mother who did not look happy. "'Love you, Dee?' 'Love you, too?' 'Boys?' If I might ask a question, What the hell is going on here?"

Dean sighed. "Robin and Jade want me to go see that new spy movie with them on Friday night."

"And you don't want to go?"

"No, mom, I really do want to go. I want to see the movie and I'd like to go out for night, but..."

"Ahh," Dr Martin said when Dean didn't continue. "That's where the 'boys' come into the equation, I'd guess."

Dean nodded. "Yeah. Robin's cousin Willie and his friends are going. They all go to St Marks..."

"And that scares you?"

"Well, yeah, of course it does, mom! I don't want to be with a bunch of guys who think I'm a girl. Who treat me like I'm a girl."

His mother nodded. "Ok... I get that, but if you ask me, I'd say that spending time with boys around you is unavoidable, so it would probably be best to get your first encounter with a boy - or a group of boys - over with sooner rather than later. I won't force you to do it, though. I'll leave that up to you, but if you decide not to go, then I don't want you to blame it on me. Understood?"

Dean's face screwed up into a look of complete bafflement. "Don't blame it on you!? Mom, this is all YOUR fault."

"My fault? What are you talking about?"

He shook his head. "Look at me, mom! I'm wearing girl's clothes. Like, all the clothes I'm wearing are for a girl. This dress. This blouse. These shoes and socks and the bra and panties underneath the dress, too. Mom, I was perfectly happy as a skinny little boy. You turned me into... this. How can it not be your fault?"

Dr Martin nodded. "Ok. I'm sorry, Deedee, but..." she sighed. "You know that I needed this opportunity and that we didn't have we didn't have a choice about your situation. You know that. I didn't CREATE this situation, it's just where we find ourselves. Now... this is January and you are going to be a girl until at least June and there is no way that you are going to be able to avoid contact with boys until then - ESPECIALLY not if you do that after-school play. So, my advice is to go out with your new friends, meet this group of boys in a safe environment and... well... have good time just like any other young lady would."

Dean looked away from his mother and steamed a bit.

"It's your decision, though, Deedee. Do whatever you want. Just don't make me the bad guy in front of my students."

She started to walk away, but he stopped her with a stern word. "Dean."

"I beg your pardon?"

"My name is Dean, mom. Can't you just call me by real name when we're at home?"

The Chancellor shook her head. "Dean is gone, Deedee... at least until June. That's all there is to it. So... the decision is yours. Enjoy being Deedee and have a nice night with Deedee's friends or sit home and mope by yourself."

She waited for Dean to say something, but he remained quiet.

"Now," she said, "if you'll excuse me for a few minutes, I'd like to shower, then I'll be back down and I'll make something light for dinner."

She walked away.

Dean shook his head and muttered, "No, mom, it's not your fault. Any good mother would turn her son into a sissy for her job. Yeah... sure. This is all my fault. I get it."
 

~^~
 

He put on the long sleeved nightie that his mother referred to as his pjs and crawled into bed. The nightie was made of very soft cotton that was very comfortable, but he was still getting used to sleeping in such a loose garment. He still woke up with the nightie sort of twisted around him from time to time.

He laid there and stared at the ceiling, taking account of his situation.

The downside? He wasn't a guy any more. Even if he went back to being Dean after his twenty week agreement, he'd never REALLY be a guy again. He will have been in dresses and lipstick for at least twenty weeks. No GUY is still a guy after that. From now on, he'd always be a sissy.

The upside? He was really getting used to these soft clothes and he liked how they felt. Being a short girl wasn't so bad. There were a lot of short girls in the world. No one really noticed and he wasn't feeling as out of place as he always had as a boy. He had friends, too! That was new and very welcome. He liked them all a lot, too, especially Robin and Jade. They not only hung out with him, they took care of him. That was welcome, too.

But the boys. That scared the bejeezus out of him. His mother had talked about him going to St Marks in the fall. Could he hang out with these guys as Deanne, then show up as Dean and expect them to not figure it out?

He didn't know.

And what if one of them tried something? Then what?

He wasn't even sure what 'something' meant, but he was pretty sure that if someone tried something and found out that he was really a boy, they'd be pretty darned ticked off about it.

He got out of bed and turned on a light, then stood in front of the mirror. His hair was braided, his face was clean, but his lips seemed to have plumped a bit, and he was wearing a soft, pale yellow nightie that hung prettily over the bra that his mother insisted he wear twenty-four seven in case someone should ever come by.

He sighed and thought about which life he liked better - the one in San Diego or the one in Greenwood. Greenwood was the answer but...

"Why couldn't I have just been born a girl?" He muttered, but having muttered it, he was shocked to have even thought it, let alone said it out loud.

He looked at himself a bit longer and sighed. "Everyone seems to like Deedee a lot more than people seemed to like Dean," he said, in a low voice. The really big problem was... so did he.

"Damn it, I wish I'd been born a girl," he said and a tear formed in the corner of his right eye.
 
 
To Be Continued...