Chapter 1 - The Mistake

Beep. Beep. Beep. Beep.

Thud.

7 AM on a Monday is probably the worst time of a week. Waking up early for school after a comfortable weekend is the last thing I want to do. My eyelids refuse to follow my brain’s instructions as they slowly shut. I begin to drift into slee……

“Aaron! Are you awake? I don’t want you to be late for school.”

I jump out of bed in a shock. There goes my dream. Ugh.

“I’m up!”

As I walk into my bathroom, I catch my reflection on the huge wall mirror. A skinny and pale boy in pyjamas stares back at me. The only thing about my body which looked lively were dirty blonde hair. If only I had some more muscles or maybe even fat.

I brush my teeth before heading for breakfast. Lily, my sister, has started crunching down on her pancakes without me.

“You could not wait for me?”

“I am sorry. I was too hungry”, she says sliding a plate full of pancakes towards me. Lily is done with her breakfast when I’m only halfway through mine. She puts her plate in the sink, washes her hands and kisses me on my forehead before heading out to work.

After breakfast, I went upstairs and took a shower. I wear a loose white t shirt and some jeans with my favourite black sneakers before heading out to school. Westford High was a fifteen-minute walk from my house and it was something I enjoyed. Those were the fifteen minutes of peace I got before entering the hell that was Westford High.

I was a seventeen-year-old skinny guy who was not popular. I wasn’t bullied because no one does that in these days. I just didn’t have any friends in school and school is boring when you have no one to talk to. I am not a nerd either because I am just an average student who makes sure he doesn’t fail any of the subjects. I just didn’t know why I couldn’t make friends.

I walk into my first class of the day – Literature. It wasn’t something I really enjoyed but it definitely was better than Algebra. I sat in my usual desk and noticed that Miss Wilson was holding a stack of papers in her hand.

‘Holy Shit! I totally forgot I had to prepare for a test.’

I gave the test my best shot and I submitted it. As long as I didn’t fail, I could explain the bad score. The rest of the day passed by quickly and like my life, it was pretty boring.

TUESDAY

After another routine breakfast with my sister, I reached school. Algebra and History classes were quite boring today and I was desperately looking forward to the lunch break. The only thing I could think of during lunch was the results of yesterday’s test. Literature was the next class and this was the first time I had been this nervous about a test.

On my way to the class, I walked past Miss Wilson’s office and noticed that the stack of test papers was on her desk. She wasn’t in her office and a dreadful curiosity arose in me. Making sure no one was around, I sneaked into her office and searched for my paper.

My heart sank at the sight of my score; 12 out of 50. I needed at least 15 to pass the test. I couldn’t face a failed test and I did the most stupid thing possible. I marked a few wrong answers of mine right and changed my score. Luckily, I had found the pen Miss Wilson used to score the answers on her desk. My heart was pounding as though it was going to break through my chest. I was sweating hard and my hands were trembling as I slowly changed the 12 into 20.

“Well, what do we have here?”

I shrieked out of fear before turning around to see that Miss Wilson was standing right behind me the entire time. She could actually expel me from school for tampering with the test scores. I accepted this to be the end of my education and decided that working in the local ice cream shop wouldn’t be so bad.

Lost in my own worries, I didn’t notice that Miss Wilson was now holding my test paper in her hand. She looked at me with a stare that was so scary I almost wet my pants.

“Both of us should be in the class at this moment, so I will take this up with you after school. Don’t be late.”

“Okay, Miss Wilson.”

“You might want pay a visit to a urinal before walking into class.”

I was mortified. I couldn’t concentrate in any of my classes. I was fidgeting and all over the place. My temples hurt really bad and I could notice my body temperature rising.

‘What am I going to do?’, it was the only thought I had in my head as I walked to Miss Wilson’s office after my last class. She was sitting at her desk and I tried knocking the door but my trembling weak hands failed to make a sound. However, Miss Wilson noticed me and beckoned me to come in and sit down in front of her.

“Could you close the door behind you, sweetie?”

Unable to utter a word, I just did what she asked me to do and sat down in front of her. She removed her glasses and placed it on her desk. Her eyes were a very dark shade of brown and they looked beautiful without glasses. She then untied her silky hair which matched her eyes and they fell smoothly on to her sweater vest.

“I’ll be with you in a minute. I just don’t like to look like a teacher once school is done.”

She unbuttoned her sweater vest and took it off to reveal a silver silk blouse with a plunging neck. She adjusted her blouse and revealed the lace trim of her black bra. I devoted all the energy I had left in me into keeping my head down and not looking at her.

“So, Aaron White, what should we do about you? I could get you expelled right now for doing what you did.”

“Miss Wilson, I’m sorry about what I did but I just couldn’t fail a test.”

“I looked into your record and I know you are a good kid. So I will offer you a way out.”

“Does that mean I won’t be expelled?”

“No. If you take my deal, I will not only not expel you but also increase your score to 40.”

These words gave me some confidence and I lifted my head up to look at her. She was a beautiful woman who dressed like a sob in school. Why would she hide her beauty?

“The deal is I let you stay in school without informing anyone about the incident and increase your score in the test to 40. In return, you have to wear panties to school every day.”

No way was I going to do that. I may not be the most masculine of boys but I sure as hell wasn’t a sissy.

“I don’t think I can do that, Miss Wilson.”

“Aaron, think about it. Your parents got divorced and you were left with your mother who had cancer. She fought through her illness to send your sister to college so she could get a good job. Now your sister works nine hours a day to keep a roof above your heads after your mother’s death. Do you really think she would appreciate you getting expelled?”

After that I couldn’t disagree. She had looked into me and knew everything about me. I was not in a position where I could afford getting expelled.

“Okay. I’ll take the deal, Miss Wilson. It’s just that no one can know about this; Not even my sister.”

“I won’t tell your sister and you don’t have to worry about the other students as you don’t have any friends. As long as you tuck your shirt in properly and wear your coat, no one will know.”

I nodded my head and sighed.

“Aaron, I am doing this for your own good. It would be best if you offered zero resistance and fall in line. I will need you start wearing panties from tomorrow. You will have to come in early and show them to me before attending your first class. You will also have to show them to me before heading home after school. Do we have a deal?”

“Yeah.”

“You may leave now.”

“Thank you, Miss Wilson.”

“Call me Rebecca in our private conversations.”

After that I went home and just lay down on my bed. I couldn’t get myself to do anything and luckily, I had no homework. I didn’t know how I would get a pair of panties. I couldn’t buy it from a store and even if I order online, it won’t arrive by tomorrow morning. My only option was stealing from Lily and on Tuesdays she has only a 5-hour shift; Meaning she was home and wouldn’t let me go anywhere near her room.

Soon, Lily called me for dinner. When I walked into the kitchen, my hair was a total mess and I looked crestfallen.

“You look like shit. Bad day at school?”

“I don’t wanna talk about it.”

“I got a message from your school about that Literature test you had. Good job getting a forty.”

“Thanks”, I said with a forced smile. If only she knew what I had done to get that forty.

“Aaron, did you fold up the clothes after the machine was done with them?”

“Oh shit! I forgot to put the clothes in the machine.”

“Are you kidding me? I don’t have any clean underwear for tomorrow. You will make sure all of the clothes are washed, dried and folded before you sleep tonight.”

“Okay.”

This was my chance. If she didn’t have any clean underwear for tomorrow, it meant that I had the opportunity to look through all her underwear and sneak one pair of panties to my room.

After dinner, Lily went to her room and I loaded all the clothes in the washing machine. Lily insisted I wash all underwear separately so I left them out. I waited for them to be washed before going through them. I didn’t want to get my hands deep in my sister’s dirty panties. I folded all the panties one by one and examined them. Lily owned a lot of sets and almost every pair of panties had a matching bra.

I knew I had to take a pair which didn’t have any matching bras and I picked out three of them. A yellow one with a lace hem, a navy-blue hipster panties and a simple black boy shorts. I wanted to go with the black boy shorts as it was the one which was very similar to my regular boxers but Lily was a size smaller than me and they definitely didn’t look like they would fit me. In the end, I decided to go with the navy blue one as it looked less feminine.

“At least, it matches my school uniform.”

I hid the panties in between a pile of my shirts and took them to my room. As I lay on my bed, ready to fall asleep, I just hoped that the next day doesn’t come.