1
Chance Encounter

“That concludes this class,” Ms. Castillo said. She set down the marker under the whiteboard and lumbered over to sit down at her desk. She landed on her chair without a moment of hesitation before making an announcement. “Make sure to read two more chapters of Pride and Prejudice and complete the short argumentative essay by the next class. You are all, officially, dismissed.”

Chatter filled the room without a moment’s hesitation as people began to pack up their things. English was the last class of the day, and I was exhausted. 11th grade started only two weeks ago, but it felt like an eternity already although the beginning of the new school year. It started off strong immediately now. There were no more icebreakers and fun activities to get to know each other, it was just straight into work. English went from fun creative writing to literary analysis. History went from exciting events to civics. Science went from interesting experiments to memorizing electronegativity values. Math. Well, math just got even more terrible.

“Psst. Hey, Jacob,” I heard a voice call to me. I snapped out of it and looked to my right to see Ryan looking at me with a smile. “You’re going to do that for me, right?”

“Well, that is what you pay me for,” I sighed. Ryan and a few other people in my grade gave me money to complete their homework for them. It was a chore but I needed the money. Ryan was one of the most popular guys in school, but I did not understand why. Everyone else seemed to love him while I found him annoying. Nevertheless, he was a frequent customer of mine.

“Do I get a loyalty discount? I swear I’ve given you a thousand dollars at this point,” he asked with a lopsided grin. He leaned back on his cheap plastic chair, putting his hands on the back of his head. “A family discount would be nice too since your brother and I are on the football team. Since the team is family, we’re basically brothers. By extension, that makes us brothers too.” He shrugged as if he just made a great revelation. “Flawless logic.”

“Sorry, no discounts,” I said with a shrug. “Also, that line of logic makes no sense in the slightest.”

“Hey, I was just joking,” he said as he playfully punched my arm. “You’ve gotten me past a lot of classes, you know.”

“Sure.”

“I swear, there’s no way you talk this little all the time,” he said with a sigh. He looked up at the ceiling a little bit in frustration before looking at me again. “I’ve known you for two years now, and all I know about you is that you’re good at studying. Underneath that mask, there has to be something, right?“

“Ryan!” someone called out. I looked over at a doorway to see someone with a bulky build leaning against the wall. “Come on! We have to get to football practice. We have a game today, remember?”

“Oh shit, yeah. See you, Jacob,” Ryan said. He swung his gym bag over his shoulder and briskly left the room.

I waited a few minutes until the classroom was empty. Students trickled through the doorway until I was the only one left. I never liked wading through crowds, and the empty hallways were well worth the wait. I finished packing my bag and stood up when the teacher called out to me.

“Mr. Parker, come up here. I have something to discuss with you,” Ms. Castillo said, waving me over. A bead of sweat dripped down my forehead. Did she figure out that I was selling homework? I could get suspended or even expelled for, as the principal always said, “violating academic integrity.” I nervously stood next to her desk and watched as she took off her glasses and idly cleaned them. After a few seconds, she finally began to speak. “I’m a little concerned about you, Jacob. You’re clearly an excellent student, but I always see you isolating yourself. I was just wondering why you don’t make an effort to socialize with other people.”

“I’m fine, Ms. Castillo. I just don’t like talking much,” I said with a sigh. I preferred keeping my head down and completing my work. I viewed school as a place to do my studies, not socialize. I just wanted to get in and get out without being distracted by other people all the time.

She frowned, looking disappointed by my answer. “I understand, Jacob. But please do let me know if you need any help. There are many good extracurriculars, clubs, and social groups at this school if you ever want to join.”

“Okay. Thanks, I guess.” I made my way out of the classroom, annoyed by her concern.

* * *

Cheap chlorine and air fresheners were just about all you could smell in the school bathroom. I did my best to hold it until I got home just to avoid it, but today I was a little desperate. After finishing up, I was washing my hands when the bathroom door opened beside me.

“Oh shit, I’m sorry,” a guy said as he stepped outside to check the bathroom sign. “Wait a second,” he paused before laughing. “My bad, I thought you were a girl. You’re Daniel’s younger brother, right? Jacob? I’ve seen you around before.”

Daniel was my older brother and was a year older than me. We were so different I often couldn’t believe we were siblings. He was a tall, athletic football player, and I was so small and feminine that I got mistaken for a girl. He was an extrovert, and I was an introvert. There were so many differences that it would take me a week to name them all.

“Yeah, that’s me.” Daniel often invited his teammates over for practice as we had a large backyard. Most of them pretended I didn’t exist, and that was good enough for me. I didn’t leave my room much when they came over except to get some water or food.

“That’s right. I’m Chris by the way,” he said with a dumb smile. “Shit, you two really don’t look alike,” he said. “What are you, 5’6?”

“5’4,” I said.

“Damn, when Daniel said he had a brother, I expected you to be just like him. I thought you’d be some big and tough guy following in his footsteps.”

Before I could respond, the bathroom door opened once again. My brother walked in, having to duck a little to even make it under the door.

“Speak of the devil,” Chris said, clapping. “What’s up, man?”

“Hey, Chris,” my brother said. The two grabbed each other’s hands and pulled into a quick hug. They laughed a little before Daniel spotted me over Chris’ shoulder. “Oh, Jacob! Are you going to come to the game today?”

“Sorry, I have to study today,” I said. “The AP Biology test is coming up soon.”

“Oh,” Daniel’s face fell a little. “You really should come to one of my games someday. It’s pretty fun, I promise.”

“I’ll try,” I gave a weak smile. “Need to keep my grades up, you know.”

“Yeah, I get it. I just wanted to see my little brother in the stands.” He looked dejected, and I felt bad again for just a second before I shook my head. I couldn’t go, not today.

* * *

I exhaled a deep sigh of relief when I arrived home. Today was a stressful day, but I couldn’t help but smile. I knew my family would be at my brother's football game today, which gave me a few hours of alone time. I took my phone out of my pocket and dialed my mom.

“Hi, Mom, when are you coming home today?”

“Probably at around 7. Your brother’s football game might take a while. Why do you ask?”

“Umm, I’m kind of hungry, so I was just wondering,” I said. I hoped that hasty excuse would be enough to assuage any suspicion.

“Oh, don’t worry about that!” she said. “We’re going to have a family dinner today after the game. Grab a snack from the fridge if you can’t wait.”

“Okay, thanks.” I quickly pressed my finger on the end call icon. I only had three and a half hours until my parents would come home and I intended to use every second of that time well. I felt bad about never showing up to Daniel’s games, but this was the only time I had for my favorite hobby.

I grew an interest in crossdressing a year ago after watching a video of someone doing it online. I felt drawn to it for some reason, and I figured since I already looked feminine I might as well try it out. I’ve been crossdressing whenever I had the time since then. For a few hours a month, I was allowed to be a whole different person, someone who was much more confident than me. I never quite liked who I was so it was exciting to become someone else, even if it wasn’t for long.

I rushed to my closet and opened it to be met with the same boring mess of denim and t-shirts. “I can finally wear something nice today,” I squealed as I pushed through to the back of the closet. I picked out a black skirt and a really cute blouse I bought a few days ago. I made sure to pick up my makeup kit as well, placing it on my desk. I had bought all of these in secret using the money I made completing people’s homework for them. It was a lot of work but definitely worth it.

I quickly took off my clothes and left them on the floor. I put on a padded bra to make it look like I had boobs. The skirt slipped on easily, I pulled it up to my waist and pulled up the zipper in the back. I put on the blouse and tucked it into the skirt. I stared into the mirror and saw a cute, slightly boyish girl with a low ponytail staring back at me. I frowned, it was close but not exactly what I wanted.

It was time for step two. I sat down, took off my glasses, and began applying some makeup. I never did anything complicated, but some foundation, eyeliner, lipstick, and blush did wonders. In a few minutes, I accentuated all the feminine features I had. I took off the simple black hair tie I always had on, and let my hair fall. It measured 3 inches past my shoulders, and I secretly had it styled as feminine as I could under my mom’s watchful gaze the last time I went to the barbershop. I brushed it a little and nodded. I didn’t have a hair iron, but it was good enough.

Now the mirror showed a very cute teen girl in an adorable outfit. Her black hair draped down her back, her azure eyes looked wide and innocent, and her makeup was subtle but effective. I smiled and made a quick twirl, watching my skirt spin. I giggled, it felt so nice to be her again. After a month of saving up money, I finally had enough to afford another trip to the mall. I hurried down the stairs with a spring in my step and opened the front door. I slipped on the white shoes I always wore and breathed in the warm air. It was time to go.

* * *

A gust of air-conditioned wind hit my face as soon as I stepped through the entrance of the city’s mall. I took a second to breathe in the crisp air, it had taken 20 minutes to walk here, and the August heat certainly didn’t do me any favors. I looked at the mall’s map to get my bearings and immediately found what I was looking for. There was a store I saw a month ago I wanted to check out, and now was my opportunity. I was a little nervous at the abundance of people, I usually crossdressed within the comfort of my home, but my excitement more than covered it up. I hurried inside and looked around, a grin growing on my face. All the dresses, skirts, and tops looked cute, and I couldn’t wait to check them out.

I hadn’t noticed that a woman was adjusting some of the clothes racks until she began speaking. “Hello! What can I help you with, young lady,” the attendant asked.

This was the moment of truth. Until now, I’d been mute when crossdressing because of my voice. I didn’t like the dissonance between my appearance and voice. No matter how feminine I looked, a male voice would out me as a guy in an instant. I’ve been practicing my voice for the past few months by watching guides online, and I finally had a convincing voice. Larynx up, keep the tongue positioned high, and open your mouth wide. I repeated the chant a few times in my head before speaking.

“Umm, are there any dresses or skirts you think would fit me well?” I asked. I immediately blushed and looked to the side. I couldn’t believe I just asked for that.

“Of course!” she said, taking a quick glance at me. “Aren’t you a cute little thing? How old are you?”

“I’m 17,” I said.

“Ah, to be young,” she said with a laugh. “Okay, follow me here, and I’ll show you some.”

“Thank you!” I said with a beaming smile on my face.

* * *

I rushed around the mall, checking the time constantly. I wanted to make the most of the little time I had. I was walking past a store when a dress caught my eye. It was a soft shade of blue lined with white dots and a cute ribbon around the waist. My eyes widened; I really wanted that. I walked inside the store to ask how much it cost.

The closest employee I could see was leaning on the counter near the register. She had one elbow on the counter, propping her head up with one hand while looking down at her phone with the other. She didn’t seem to notice me even though I was within a few feet of her.

“Excuse me,” I said to get her attention. She sighed and looked up at me, giving me a look on her face that said “make it quick.”

“Hi, do you know how much that dress in the front costs?” I asked, pointing to it.

Without a single word, she walked up to it and pulled back the collar to look at the tag on the back of the neck.

“125 dollars.”

“Oh,” I said. My face dropped. That would take a long time to save up for. I had already spent all the money I had earned in the past month. I looked at the two bags of clothes in my hands with a frown. I should have circled the entire mall once before buying anything.

I turned around and headed out the door, looking longingly back at the dress as I walked past the store. I checked the time, 6 o’clock. I had to get back home to avoid getting caught by my parents. They certainly wouldn’t like me doing this, let alone getting them to buy a dress for me. I started walking towards the exit. I only had an hour left and had to get home. Washing off makeup, doing my skincare, and hiding all my clothes would take a while. I looked down at the floor, calculating how much homework I would have to sell to afford the dress.

I bumped into someone all of a sudden. “Ah, I’m so sorry,” I said. I stumbled back a little and dropped one of my bags. “I wasn’t looking, and I-” My heart suddenly stopped. The guy in front of me was Ryan Morgan, the school’s football star, a regular client of my homework business, and someone who I talked to just a few hours ago. What was he even doing here? He was supposed to be at the football game with my brother. I immediately looked to the floor again, hoping those few seconds hadn’t revealed who I was.

“Jacob?” he asked. His eyebrows furrowed as a look of confusion covered his face. “Wait, is that you?”

“Umm, I don’t know who that is. Sorry, bye!” I blurted out. I picked up my bag and turned around, making a beeline toward the mall’s entrance. My heart was pounding so hard it was about to burst out of my chest. There was no way this just happened. There was no way I just got caught crossdressing by Ryan. This wasn’t real, it couldn’t be real.

“Wait, hold up!” he yelled. I could hear his voice faintly but I was already far gone.

* * *

“Damn it,” I said. How could I have been so stupid as to go to a mall ten minutes away from school? I never considered that someone from school would recognize me there. I swung open my home’s front door and sank to the floor. I was so screwed.