Crystal's StorySite


My First Day at Understanding High School

by Jennifer Allison


"I want to welcome all of you to Understanding High School." said Ms. Roth-Morton, my new school's principal. "This is a new school in an old school building, but a school set up for the needs of all its students."

Let me explain how Understanding High School came about and the reason I am attending. First the school. The city I live in has a population of around a half million. This city is also one of the richest in the country, so the school system gets all the money they ask for.

Understanding High School came about after the third lawsuit brought by the parents of a student that was hassled or harassed just because they were different. We all know the types: The Nerds, geeks, undersize boys who couldn't defend themselves. The gay students and the students that everybody thinks are gay. Boys aren't the only ones who have these problems, tomboys and the girls who dress like a butch do, too.

So this high school was set up for these students so they could go to school without worrying about a football player beating them up cause they refused to do the team's homework. A student caught hassling another student is automatically sent back to their old school. They fixed their first problem before school started. Understanding High School would have no athletic program. Physical Education yes, but no after school teams

As for me - have two problems that I know for sure Understanding High will help me with. I stand 5 foot 3 and weigh in at 120 dripping wet. I spent so much time locked in my own locker the teacher working the room next to it had the extra duty of checking to make sure I wasn't still in there before he left for the day.

I also like wearing women's clothes. This problem has given me so much trouble. A couple of times I almost wore a pair of panties to school. These were the reasons I put on the Understanding HS application. My parents knew about the first problem but not the second. If my dad ever found out I'm afraid of what he would do.

July 27th will always be a holiday for me. On that date Ms. Thornton, a counselor at Understanding High, invited me to attend the school.

"Dean, first things first. You have been selected to attend Understanding High," she informed me. "Do you have any questions before we go any further?"

"Was I selected for my size or my other problem?" I needed to know.

"For both," Ms Thornton told me. "But either one would have qualified you."

She explained more about Understanding High. "There will no hassling or harassment like your last school. If a student is caught they will be sent back to their old school. From what we have heard from the schools, anybody sent back will be considered gay whether they are or not."

"You won't have to worry about me going back." I said.

"That 's not the only rule that will have you sent back to your old school. We will not tolerate anything of a sexual nature on school grounds. Kissing is allowed but that's far as it will go. Off school grounds we cannot control." Ms. Thornton told me.

"You still won't to worry about me on that part. I've never even had a girlfriend." I said.

"Anything means heterosexual or homosexual in nature. Around 40% of our students will be gay." she said with a stern look in her eyes. "There will be no relationships between students and teachers. The main reason behind this is that the teachers also filled out a request like you did. Some are gay, others like wearing women's clothes. Most of them who like dressing will be teaching in any type clothing they like."

"I understand." I said. then I asked "What about my other problem?"

"We're working on that. Some of the male students will arrive dress as girls. Something will be worked out for others like yourself whose parents don't know their secret."

As Ms. Thornton finished saying this, she stood up and offered me her hand. "I want to welcome you to Understanding High. I have another student arriving in five minutes."

"I have a question before I leave. How many others are like me. The ones that their parents don't know about the need to wear women's clothes?"


I got up and left.


First day of school. Here I sit along with 200 students listening to Ms. Roth-Morton in the school's cafeteria.

"Understanding was setup to help those kids who do not fit in any place else. Each of us has our problems - teachers, students and administrators alike." Said Ms Roth-Morton.

A voice in the back said in the back, "Administrators?"

"Administrators, and that includes me. I asked for this job. When I stated my qualifications I was immediately accepted. Would you like for me to tell you about my special qualifications?"

There was a chorus of, "Yes!"

"I have the body of a woman except one piece of equipment between my legs. I love the way I am. Most, if not all, of your teachers have some of the same problems you are having, that's why the threat of being fired was always on their minds. As with you students, no sexual activity will be allowed among the teachers, between teachers and students or among the student body. I want you all to remember this school is on a trail basis. If you mess it up so the school board decides to close Understanding, you will be putting the students in later classes through the same hardships and problems we are trying to eliminate.

"In closing, I want to say this. Follow the rules set forth in the Understanding handbook and there won't be any trouble. Then in twenty years, at your class reunion, you'll be proud to be the first class of many graduating from Understanding High School."

Ms. Thornton then took the stage. She announced, "I have no speech prepared" and the sound of clapping filled the cafeteria. "I just have one announcement. Will the following students report to room 26." She then read twenty-two boys, my name was included on the list. "Also will the following students report to room 19." Ten girl's names were read off. "The rest report to your 3rd period class. You are now dismissed."

Five minutes later there twenty-two boys standing outside the locked door of room 26. From the maps we were all given, room 26 was about three times larger than any other classroom. A minute later Ms Thornton showed up. As we gathered around, Ms. Thornton said. "During your interviews last summer you were told we were working on your problem of wanting to dress like a girl and go to school, but were unable to due the fact your parents don't know about this. I hope you all love the way we settled your problem." she said as she unlocked and opened the door to room 26.

The shock of seeing Ms. Roth-Norton's dick was nothing compared to the shock the twenty-two of us had when we looked inside room 26. We just stood there and stared. Our brains couldn't comprehend what our eyes were seeing. Along the wall across from the door stood vanity mirrors, the type you would find in a teenage girl's bedroom for applying make-up. Along another wall stood racks upon racks of dresses, blouses, skirts and sweaters, too many to count. There also five chests of drawers.

"These are the clothes you can wear while you attend Understanding High. If you want to dress up, you can come early enough to get dressed be on time for your first class. After your last class you can change back into the clothes you wore to school. The chests of drawers will hold your training bras, panties and the other undergarments that a girl needs to wear."

Before another word could be said, a few of the boys started to unzip their pants.

"Hold your horses."

"Yes ma'am." the boys replied.

"There are twenty-two racks. Each one has a name on it, those clothes were set aside for that person. You have two drawers set aside for your own undergarments."

As Ms. Thornton was telling us this, we all lined up like the drivers in a motorcross, just waiting for the gun to go off.

"You may begin."

Most of the boys ran to the clothes rack. Me, I headed for my undergarments. I wanted the feel of panties around my dick and I wanted it now. Within a minute there were twenty-two naked teenage boys laughing and giggling like twenty-two teenage girls.

I paused to enjoy the feeling being caused by my bra and panties. This also gave me time to watch the other girls, I should call us girls now, as we tried to decide what to wear for the for the first day of school.

"Come on girls, make up your minds. We don't have all day." Said Ms. Thornton. "Pick something nice to wear. Tomorrow you can match everything up perfectly."

When the crowd subsided around the dress racks, I went over to pick out my dress for the day. It only took me moments to decide which one. It was an exact copy of a dress I have seen my mom wear. I have had many daydreams about wearing this certain dress. I was one of the first to sit down at the vanity tables, still in just my bra and panties. I didn't want to get any make-up on that beautiful, wonderful dress.

"Dean, wait until the others are sitting down." Ms. Thornton told me. "Then I will only explain only once on how apply your make-up."

I had to make a decision. So finally put on the dress I had dreamed of wearing. It wasn't as much as people would think, just something a high schooler could wear. Not wanting to put a run in my first pair of panty hose, I chose to wear knee high socks that matched the dress and a pair of Mary Janes. By the time I finished tying my shoelaces, everyone else was dressed.

"First, I want each of you to take a hair brush. Then use it to make your hairstyle more feminine." Ms. Thornton walked down the line of girls, helping those who couldn't get their right. "Since there isn't much time before the bell, I will show you how apply your lipstick and rogue. Tomorrow, during PE, your instructor and I will go into more detail about make-up and other things a girl needs to know."

I went with a conservative look concerning my lipstick and rogue. Then the bell rang.

"Remember, tomorrow when you are scheduled for PE, report here to room 26 instead." Ms Thornton told us as we were leaving. "Also don't forget your purses."


There were no stares or rude comments directed at me as I walked to my next class. The students of Understanding High accepted a person for what they were inside, not the outside. My next class was history, followed by economics; they were in the same classroom but had different teachers. As I entered the room, one of the other students waved me over to take a chair next to her. She wasn't one of the twenty-two.

"Hi Dean." she said as I sat down.

I knew the voice from somewhere but couldn't place it.

"I bet you don't recognize me underneath my feminine grab." she said.

Finally the 2x4 came crashing down. "Sam, is that you?" Sam Crawford is my best and only friend from my old high school.

"When I am dressed like this I prefer Sabrina."

"Why didn't you tell me about your dressing?" I asked.

"The Rules. When My parents caught me all dolled up, they set up some ground rules. I could dress up as much I like as long as I didn't tell anyone." she informed me.

"How are they about you attending to Understanding?" I asked.

"I didn't even have to sign up, my parents did it for me. I was one of the first students registered. Your parents don't about your need to dress up, do they?" she asked.

"No, they don't." I replied.

We had to stop talking. The History instructor came into the room.

"Students, please take a seat. Anywhere you would like. I don't arrange seat assignments." He informed us. "My name is Mr. Foster, I will be your history teacher." He stood in front of his desk. "I want to tell all of you why I am teaching here at Understanding. I am gay; I didn't come out of the closet until after I was accepted to teach here at Understanding, so I will do nothing that will jeopardize my job here."

This happened with all of my classes. Each instructor told us their reason for being a teacher at Understanding.

Sabrina and I had only history together, but we usually got together at lunch. We sat with a few other students that we met in our other classes.

"Dean - Oh I forgot to ask your femme name." Sabrina said to me.

"Is it that important?" I asked.

"It is. You're dressed like a girl, you should use a girl's name. Dean just won't do."

"I've always liked Jennifer." I told her.

She then introduced me to the others at the table as Jennifer.

"Hi, my name's Brock. You're one of the twenty-two boys who haven't told their parents they like to dress in girls clothes, aren;'t you?" Brock was dress as a boy but she was obliviously a girl underneath. "Don't worry, I have the same problem. I haven't told my parents that I'm a butch, so I have dress like a girl before I leave the house. When I get to school I change into these wonderful clothes."

After lunch I found out that the students weren't the only ones who had to hide their secrets from their family. My English Lit. teacher Ms. Jamison explain hered problem to us.

"I am a closet crossdresser. If my wife every found out about my problem, she would be just a streak on her way to see a divorce lawyer. So like some of you students, I will change here at school." she said.

So that's how Understanding High School came about. A school where students, teachers and administrators could be what they are or want to be without having to worry that others would hurt them. A place where teachers teach and students learn in a healthy environment.

It was one sorry sight in room 26 after the last class, as the twenty-two of us removed our feminine finery. The only thought that stopped me from bawling was that tomorrow I could again become Jennifer. By sheer luck Mr. Jamison, my English Lit teacher, lived only about four blocks from my house. Since we both needed to come in early and leave late we decided to carpool, but since there was no way I was going to be sent back to my old school and Mr. Jamison didn't want to get fired, that was all of it.


As I walked through the kitchen door. My mom asked, "How was school today, dear?"

"Great! For once I won't mind going to school." I replied.

"You had better go wash off your face before your dad gets home." she told me.

"Why?" I asked.

"You didn't get all of your lipstick off." pointing to her lip as she said this.

"MOM!!!!!" I almost screamed.

"Don't worry, I know all about room 26." she informed me. "Why do you think that all of your clothes fit so well? Then there's your favorite dress of mine. How do you think it came to hang on your rack? I'll lay you 10 to 1 that was the dress your wore today."

"Yes it was. How do you know about all of this?" I had to know. "Does dad know?"

"No he doesn't, and that is the way I want it." she told me. "I've known for years about your crossdressing. You weren't as careful as you thought you were. I found my clothes out of place or with unsightly bulges where there weren't supposed to be bulges."

"Why didn't you say anything?" I asked.

"I just figured you'd work out of your system. When the school district set up Understanding, I knew it was the perfect high school for you. Remember last June when your father got so mad at me for going over my budget? I wasn't buying clothes for me, but for you. I knew you would be accepted at Understanding last May."

Kissing her on the cheek. I said, "Thank you." and went off to wash my face.

As I walked away she said. "Dean? You'll still have to use room 26. We don't your father to find out about my daughter, do we?"

"We certainly don't." I answered.




2003 by Jennifer Allison. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of StorySite and the copyright holder.