Ch 1: Girl’s First Day

jessie 400 subtitle
Let’s face it, high school kind of sucks. People who aren’t the typical jock or cheerleader type tend to have a rougher time because they’re considered outcasts of some sort. Strange, abnormal, or odd in some way. For most people, this goes on unchecked. They just meander to and from class, have fun with their friends, and live their totally normal and largely uneventful high school lives in peace despite not being one of the ‘cool kids’.

It was this uneventful, peaceful and carefree high school life that Jessie Oliver wanted more than anything right now. He’d give anything to just go to class unnoticed, do his school work, read a book at lunch, and go home without any trouble whatsoever. Something poor Jessie had never really had in life, but was hoping would happen today.

“Hurry up, Jessie! You’ll be late for your first day!” a gruff voice echoed up the stairwell, sending a shiver down his spine.

Despite being hopeful that today would be a fresh start, Jessie was still dreading the more realistic probability of what the day would have in store for him.

“I don’t even want to go! All-boys schools suck!” a rather daintier voice whined back down the stairs. “I’m going to get bullied every day!”

“That will never happen,” Jessie’s father said, having climbed the stairs to greet the small boy in his room. Jessie was rather short and had a feminine face to match his voice. With his big green eyes and not-so-short auburn hair, he was more like a doll than a high school student. His father knew that Jessie was a late bloomer but with how girly his son looked, that was a real understatement.

Jessie’s father sad down on the bed next to the feminine boy and put his arm around his shoulder in reassurance, but he knew that he couldn’t completely erase the anxiety of his first day. He still had to try, though.

“That Pierce Private Whatever-Its-Called place is a very well-renouned school, and it cost a fortune to get you in there.”

“I thought I got in on a scholarship,” Jessie said with an incredulous look up at his father.

“I, uh, well, that certainly helped– but that’s beside the point! You’re fourteen now and being around boys your age will be a good influence on you. They have tons of great sports programs and community programs you can sign up for. I’m sure you’ll make friends in no time!” he replied with a smile that Jessie did not find reassuring in the slightest.

“Just like the last school I went to? And the one before that? You know putting me in a place like that is just going to make a repeat of… last time…” he began to trail off, but a call from his mother down the stairs made him lose the train of thought he was about to take a ride on.

“Come on, boys! We have to go or you’ll be late!”

“You heard the lady. Let’s get going,” his father said as Jessie sighed and reluctantly grabbed the strap of his backpack. Seeing the defeated look on that cute face pulled on the man’s heartstrings and he once again placed his hand on the boy’s shoulder. “It’ll be ok. I promise this time will be different.”

“It had better be.” Jessie immediately regretted the acidic tone he said that in under his breath, but his father decided not to scold him. He knew today was going to be a rough one for the cute kid.

Jessie’s gut was sinking with fear as he sat in the backseat of the car. Being a transfer student in tenth grade, just after the start of a new year, was bound to give him all sorts of attention that he didn’t want. ‘And that’s on top of the usual attention I tend to get…‘ he thought to himself.

That sinking dread in his gut lapsed for a brief moment as the car pulled into the gated parking lot in front of the massive campus. He was lost in the moment, taking in the sights of his new school as they rolled slowly forward to the walkway out front. Tall buildings fanned out from behind the nearest in a ‘V’ shape from what he could tell. ‘How many are there? Five? At least!‘ he awed.

The huge campus was surrounded by tall pine trees and in the dead center, at that foremost building Jessie determined must be the office, was a walkway spreading out in front of him lined with ornately trimmed bushes in various animal shapes and a sparkling two-tiered fountain. Surrounding the fountain were groups of kids in light brown uniforms. Some chatting, some playing hackie-sack, and others rushing to and from the office with paperwork in their arms. Among the sea of khakis and blazers Jessie saw something he thought he shouldn’t have, but then he noticed another. And another. And even more. Sure enough, many of the students were wearing skirts as well.

“Wait, I thought you said this was an all-boy’s school?” he asked his parents in disbelief as they pulled to a stop right across from the fountain.

“Well, that side is!” his mother said, gesturing to the row of buildings fanning off into the distance on the right side of the office. “The other side is an all-girl’s school. They share common facilities like the office and the gym, but the classrooms and dorms are separate.”

“That’s…. unexpected. I don’t know what to say to that,” he gaped, eyeing all the students wandering about. Every one of their uniforms looked pressed and fitted and really drove in how expensive this school must be to attend. That thought made Jessie’s anxiety return in full swing knowing that wearing his street clothes would just draw even more attention. “Will I be getting a uniform too?”

“They should have it waiting for you in the office, dear” his mother replied. “Today is fine for you to go as you are, but be sure to pick your clothes up before we come to get you because you’ll have to wear it tomorrow, ok?”

“Yeah, no problem. What about the dorms? Did you sign me up for that, too?”

At least the uniforms are distinct. I won’t be mistaken for a girl wearing those slacks,‘ he assured himself. Those dorms in the back scared him, though. ‘Living with guys? Nothing but nasty sweat and muscle.

“Of course, son!” his father cheered. “There’s no better way to make friends! They could help you sign up for a sports team. I hear the gym has a weight room that dorm residents can use in the afternoon, too! You could build up some of that muscle!”

“No. Way.” Jessie proclaimed through grit teeth as he got out of the car. “I don’t want to get all bulky and clunky. I like how I am.” ‘Mostly…‘ he mentally added.

“Don’t worry honey, it won’t be for a little while. We’re waiting for an opening, since you’re a late transfer and all. We’ll pick you up here at three, ok?” his mother said hanging her head out of the window. “Hang in there, ok? Try to have fun! It’s not every day you get to start over and make first impressions, right?”


Unfortunately, his mother’s encouragement was lost on him. He just slung his backpack up on his shoulders and kept his head low as he began making his way to the office building and past all of the curious stares that followed him along the way.

“A hoody and shorts? What is she thinking?” he heard one girl say a little too loudly.

“Who’s the new chick? Fresh meat?” a random boy said.

“I’m not into tomboys, you can have her,” his friend responded before they broke out in laughter.

Jessie’s cheeks tinged with embarrassment as he quickened his pace. ‘Gossip…‘ he thought. ‘It’s already started. Maybe I’ll put that uniform on in the bathroom or something.

Jessie stood outside the noisy classroom trying his best to ignore the snippets of conversations he was hearing through the hall windows. He didn’t want to accept that all this talk about the ‘cute new girl’ was really about him. Denial couldn’t last forever.

The teacher walked in and the bell rang. With a loud WHAP of a yard stick against his desk, the teacher had gotten the full attention of his teenage hoard.

“Listen up, everyone,” Mister Schroeder commanded. “We’ve got a late transfer joining us today. Jessie, step in here please.”

This was it; the dreaded moment come to pass. Jessie tried to shake the embarrassed flush from his face to no avail before walking into the classroom, eyes glued to the floor. He stopped short of the teacher’s desk and turned to face the crowd, but shyly kept his head down.

“Well, go on,” Mister Schroeder coaxed. “Introduce yourself.”

Here goes…‘ he thought before clearing his throat and stuttering out, “I-I’m Jessie O-Oliver…”. He wasn’t good with being put on the spot, and this was making his blood pound so hard he thought he might pass out.

Mr. Schroeder let out an impatient sigh. “…alright boys, this is Jessie Oliver. He just transferred here from Regence High in Loston. He’s a little…” he paused, looking over his glasses at the blushing boy in question, “cute, as you can see, so try not to beat him up or anything.”

Jessie turned in panic at the teacher. ‘‘Cute’?! Is this guy TRYING to get me killed?!

“Any questions for the new kid before we begin class?” he continued, in a disinterested; almost lethargic tone.

The entire class had been staring in wide-eyed surprise and complete silence at the kid in front of them. After a few seconds of silence, one random boy from the second row finally raised his hand and asked what the rest of the class seemed to be thinking. “Yeah, I got a question. Why’s she on our side?”

Jessie blushed and a few more boys chimed in with snickering and questions about why ‘she’ wasn’t in uniform. “I-I’m a guy!” Jessie nearly shouted back.

“For real?” the boy responded, letting his hand lower limply and giving Jessie a very quizzical look. Not a harsh look, Jessie found, but one of complete surprise and some curiosity as well.

“Umm… yeah?” he said, trying his best to keep his cool. It was clear to Jessie that the guy wasn’t making fun of him, but that worried him just as much. He tried to keep his hair fairly short and keep his body language decidedly masculine whenever he was made aware of it, but at the end of the day he was still a slender short boy with a cute face that betrayed him. “I’m just a… what’s the phrase?” he pondered aloud mid-sentence before it came to him, “late bloomer! Yeah, that’s it. I’m a late bloomer. Haven’t hit my growth spurt yet is all.” He was completely red in the face as he stumbled through his excuse before turning to the teacher and asking if he could sit down yet.

Schroeder was eager to get the day over with just as much as Jessie, so he obliged. “Yeah, whatever, just take that empty seat by the window in the back.”

You don’t have to tell me twice,’ Jessie thought as he shuffled his way past the silent inquiring stares and plopped down in his seat. However, the moment he sat down, his nearby desk neighbors all turned to him with question after question.

“Are you really a guy?”

“Why do you look so girly, you got a hormone disorder or somethin’?”

“Dude, I think he’s blushing…”

Jessie sank down into his seat, his face getting redder and redder with every question posed to him. He wanted anything to escape the barrage of comments and questions and his salvation came in the form of another loud WHAP of Mr. Schroeder’s yard stick.

“Shut up and pay attention! Class has started! You can all harass your new little ‘princess’ afterwards.”

Everyone snapped to attention and faced forward in fear, including Jessie who was glad to finally have the heat off of him. ‘This teacher’s either protecting me or trying to kill me!‘. He couldn’t decide which.

Class continued with no more problems, but when lunchtime rolled around it was question after question after question. Being his first day, Jessie had been expecting this, but it didn’t make it any easier.

“Where are you from?”

“Why’d you move here?”

“Why do you look so weird?”

“Planning to try out for a sports team?”

“Wanna join our club?”

All questions Jessie was hoping to avoid because he had no clear answers to any of them. Well, most of them.


“I dunno.”

“I dunno.”


“I dunno.”

Every question dodged, he finally found a place to enjoy the rest of his lunch reading his favorite book in peace, but soon after the bell rang and with it he had to shuffle back to the classroom. Mr. Schroeder stalked in a few minutes late, but class immediately resumed with the next subject of the day and Jessie could dive straight into his new schoolwork. It was a nice escape to pass the time. Before he knew it, a bell rang at ten minutes to three.

“Alright, that’s it for History. Before you start cleaning up, I have a reminder for you all,” Mr. Schroeder announced.

A ten minute clean-up period before we can leave? The students clean the room? That’s weird…‘ Jessie thought.

“Keep in mind that the school-wide ‘open house’ carnival is coming up soon. I think it’s…. Friday? Perhaps the one after that? Or was it a Saturday?” he started trailing off before coming to a conclusion with the shake of his head. “No matter, I don’t really care. The point is, bring your parents and your friends from other schools to check it out. It’s a fund-raiser and open house event, but we’re also trying to rope in new kids like Jessie there.”

A few random eyes turned to Jessie, and he just smiled sheepishly and found something very interesting out the window the stare at.

“The fund raiser part is done on a class by class basis. All of the proceeds will go towards the class. It’s technically optional, but I highly recommend you do it,” he seemed to warn with the tone of his voice.

One random boy wasn’t intimidated and had a burning question he just had to have answered, so he shot up out of his seat, hand in the air, and asked before getting permission, “I-is this thing going to be mixed? Are we gonna be able to hang out with the girls?”

“But you already have one to hang out with right here,” another boy replied, gesturing to the tomato that seemed to have replaced Jessie in the seat by the window. The class erupted in laughter as the boy sat down and Jessie tried to hide his tomato behind an open textbook on his desk.

“Leave him alone already, it’s only his first day.” When Mr. Schroeder told the class to do something, very few had the guts to say no. The laughter immediately died, leaving Schroeder to continue his announcement. “Yes, the girls will be there. If you make enough money with whatever fund-raising event you decide to put on, we can go on a week-long field trip during the first week of winter break. Or, you can let me have a relaxing week without babysitting you brats before I spend my Christmas in Hawaii. Your choice. With that, I’m out of here. See you all tomorrow.”

Mr. Schroeder walked off and the boys all went back to packing up their books and binders while a handful groaned their way towards a broom closet to get some cleaning supplies. As everyone started to leave, Jessie was reminded that it was finally his chance to end this stupid day and go home. He just wanted to go home, get some rest, and forget this day ever happened.

He pretended to be buried in his book while waiting for everyone to leave until it was just him and the cleaning crew. Before anyone could take a break from their chores to harass him with more questions, Jessie was packed and gone. He found himself walking behind a group from his class down the halls but tried to make sure nobody knew he was standing right behind them.

That may or may not have been for the best, as Jessie caught wind of everything they were saying about him.

“So what’s the deal with the new kid? No uniform? The dorm head didn’t say anything about a new arrival today,” one boy asked to his friends.

“Got no room, right?” the shortest of the three replied.

“Or maybe she just doesn’t want us to find out her little secret, heh…” said the third.

“Yeah! The dorm thing might just be an excuse!” the short one added, laughing along with his buddy, but the first and tallest of the trio ended the joking pretty quickly.

“Calm down guys. He looks like a girl and all, but you saw how upset he was. He probably hates being called that.”

“OooOOh, Eric the white knight rides up on his trusty steed to save the princess~!” the short one cooed dramatically, causing the other friend to laugh and Eric to sock the short one in the arm.

“Knock it off, man. Don’t bully someone for something they can’t help,” Eric lectured while the short one rubbed his sore arm.

“Fine, whatever,” the third one said.

None of them noticed that Jessie had been walking just a few feet behind them, awkwardly trying his best to conceal his presence. Jessie couldn’t help but be grateful that this Eric guy stood up for him. ‘I guess they’re not all bad,‘ he thought. Finally out of the building, the group of boys veered off to the left, no doubt heading for the dorms, leaving Jessie a clear path to the office.

Minutes later, Jessie was walking out of the building and towards the fountain with a brand new uniform in a bag. Sadly, the trip from the office towards the parking lot was met with even more questioning stares and whispers from the dozens of students, boys and girls, who were hanging out in front of the school.

Jessie could feel his face tinge at the attention, but kept his eyes down and moved briskly forward trying to get away. ‘Why do they keep staring at me?! What is WRONG with me?‘ he cried internally. ‘Why is it always like this at every new school I go to? Why can’t I just be nor-‘OOF!!

“What the hell was THAT for?!” a pony-tailed girl yelled from down on the brick pavement. She’d been knocked flat on her butt when Jessie slammed into her, scattering her books and papers all over.

Jessie panicked, and immediately started gathering up the girl’s papers while stammering, “I-I’m so sorry! I didn’t mean to! I wasn’t w-watching where I was going, a-and I-”

“Woah, that’s so cool!!” the girl said.

“Huh?” Jessie blurted, confused by what he’d heard, and turned to see the girl examining Jessie’s new uniform that had fallen out of its bag in the impact. She had a smile on her face and sparkles of envy in her eyes.

“Your uniform! Lucky! I wish I could wear the boys’ uniform to school! Or at least the slacks, anyway…” she trailed off.

Oh, not again…‘ “I am a bo–” he started to correct her but she cut him off again.

“Let me guess. New girl? Haven’t seen you around today at all. That’s gotta be why you’re wearing normal clothes, right?” she bubbled at a mile a minute. “Looks like the office gave you the wrong uniform, eh? Don’t you have the girls’ uniform yet?”

This girl was ignoring him, and Jessie was sick of being mistaken for a girl yet again today. And this time by an ACTUAL girl! He’d had enough. He composed himself and sternly started as coldly as he could, “No. I don’t have the girls’ uniform because I am NOT a gir–” but she cut him off again, completely impervious to the assertive attitude.

“Well, no big!” she kept herself from shouting as she got up and dusted her rump. She held out her hand with a gleam on her face. “The name’s Ash, by the way. Short for Ashley. I’m in Mrs. Stable’s stables! Heh, get it? Stables? ’cause her name is Stable and her classroom is like a… Oh, nevermind. Nice to meet you!”

Jessie couldn’t believe this girl. She must have had sugar flowing through her veins with how energetic she was. Jessie saw her hand out and paused from picking up her books to really take in what he was seeing. ‘She’s got to be a candy addict or something,‘ Jessie thought, cautiously taking her hand. The second it met hers though, she yanked him up to his feet with a hard jerk.

“I-I’m Jessie,” he said, finally getting his hand free after she shook it violently. He winced as he rubbed the sore joints that were finally free from her iron grip.

“Jessie, eh? It’s a pleasure to meetchya! What class are yo–” she began to ask before being abruptly interrupted by the blare of a car’s horn.

“Jessie, get over here! We’re in a hurry! You can talk to your girlfriend later!!” his father shouted from the driver’s seat of the only family sedan in the lot.

“Oh, how rude to interrupt someone while they’re talking!!” Ashley scowled at the car, completely unaware of the hypocrisy of her statement.

Or maybe she’s just an idiot…‘ he decided. “T-that’s my dad, I gotta go. Nice meeting you I guess! Sorry for bumping into you!” Jessie grabbed his uniform and stuffed it in the bag, running off towards the car. He even gave a small wave goodbye.

It happened so fast that Ashley was astonished at Jessie’s speed. It’s almost like ‘she’ was trying to get away from her as fast as possible or something. All she could do was wave goodbye in return as the car took off.

“Wait, did that guy say ‘girlfriend’? Does Jessie swing that way?” Ashley pondered aloud, going back to collecting her things. “Good thing this isn’t a Catholic school anymore! If that got out back then, there’d be hell to pay! Literally!”

She was a tad disappointed that nobody was around to laugh with her.

Jessie slumped down in his seat at the dinner table, ready to put the day behind him as his mother placed some pots on the table and father passed around dishes.

“Hurry up, hurry up!,” Jessie’s little brother pounded with knife and fork in hand. “I’m starving, you’re taking too long!”

“Well I guess we know who’s setting the table tomorrow night!” their father said with a scowl as he handed the boy a plate.

“What?! Why do I have to set the table? That’s womens’ work! Make Jessie do it!” he shouted, earning a nasty look from his brother. Before Jessie could say anything back though, his mother was already on the case.

Jason!! Don’t be sexist!” his mother snapped, causing him to flinch and quietly apologize.

“What, my little man here? Jason, you’d better look up to your big brother, he’s going to be a real man among men one day, just you watch! His new school will make sure of that! How did your first day go, anyway?” He beamed at Jessie, thinking his praise would go appreciated, but it was completely lost on the boy. Sure, he wanted to be treated like a normal person more than anything, but to be a big sweaty hairy nasty ‘man among men’? He wasn’t very enthused about that idea. He may have disliked his girly appearance, but only because of how people treated him over it. He didn’t want to change into something he’s not.

“Well, about as expected, I suppose… not that great, not terrible.” Jason finally had a grilled cheese sandwich on his plate alongside a bowl of stew and was noisily going to town.

“Are you making lots of new friends, sweety? What about that girl we saw you with after school?” his mother asked, while patting Jason on the back as he choked on a bit of his sandwich.

That’s what you get for eating so fast,‘ Jessie thought. It was nice to have a little divine revenge on the brat.

“That’s my son, getting a girlfriend on his first day of school! You’ve got your father’s genes, that’s for sure, HAHA!” his dad shouted in jest with a smile, making Jessie sigh and Jason snicker.

“She’s NOT my girlfriend, just someone I bumped into on the way out. Besides, I think she’s got a screw loose or something.” That girl was just way too hyper for his tastes. If there was any consolation with going to the all-boys’ side of the school, it’s that he’d probably never see her again.

“I didn’t know your school allowed for lesbians!” Jason laughed. Jessie hated that little prick. He was a few years younger and still in junior high, but he made fun of poor Jessie every chance he got. At home, when Jessie was at his part time job, it didn’t matter. Jason was always there to push buttons. ‘Another consolation of living in the dorms, I guess.

“Jason, that’s not nice! You apologize to your sis-, er, brother, right now!” their mother commanded, resulting in a laughing fit from Jason. “Sorry dear, it was an accident, it just slipped out…”

Jessie rolled his eyes and sighed, focusing on his dinner without acknowledging his mother’s apology.

“Cheer up, champ! You have a new school life ahead of you. A whole new chance to shine. So what if you’re a little feminine looking! In another year or so, the girls will be falling all over you and the guys will be jealous of your good looks. I guarantee it!” If Jessie’s father was anything, it was optimistic.

Unfortunately, that trait wasn’t passed on to the next generation. “I’m almost fifteen and I haven’t gotten any more masculine. If anything, I’ve just been getting more girly-lookin’. A year from now I’m more likely to be in a skirt than a suit at this rate.”

“Don’t be so down on yourself, Jess. Things will get better. You’re getting older now and everyone around you is maturing. If you just be yourself, they’ll see you for who you are and not what you look like,” he said putting his hand on Jessie’s shoulder.

Jessie looked up at him with worry and disbelief, then back down at his plate. He knew what his dad said was supposed to be true. That’s what they always say in the books and movies. But does it ever happen in real life? After a day like today, Jessie was convinced that it was just a hopeless dream. But then he remembered something that gave him hope.

“Well, there was one guy who stood up for me today. His friends were joking about me and he got them to knock it off,” he recalled aloud. “That and the teacher kind of told everyone not to pick on me… after he called me ‘princess’, though…”

“See? Things are changing. Maybe that boy can be your first friend at Pierce!” his mother optimistically suggested.

“Yeah, your first BOYFRIEND!!” Jason chimed in, but Jessie wasn’t having it anymore. He turned and socked the younger boy in the shoulder as hard as he could, but ended up hurting his hand more than he hurt him. He wouldn’t show it, though. He just kept his cold glare.

Mooooom, Jessie’s hitting meeeee!” he whined, but their mother just took a casual sip from her glass.

“You deserved it,” she casually replied.

Later that night when Jessie finally made it to his bed, he took solace in the fact that the first day was over and, theoretically, it should be easier from here on out. He had his uniform so nobody would really be able to question him anymore, and even had someone at school who might have his back.

“Maybe this won’t be too bad afterall,” he quietly thought to himself, climbing into bed and looking over at his plushy stuffed rabbit.

There was one girly thing that Jessie secretly enjoyed, and that was his little blue rabbit named Jack that he’d had since he was four years old. The cute little bunny had brought him comfort in hard times for over a decade now, and it was a little sad that he’d have to say goodbye.

“I’m going to live in the dorms eventually,” he whispered to the doll, “so we don’t have much time left together. It’s going to be hard without you buddy, but I’ll be back someday. Be good, ok?”

With a light kiss to the bunny’s plastic nose, Jessie snuggled it tight and drifted off to sleep. Tomorrow was a new day, and his first real chance at a new life, and he was going to try and take it.

——————– <Next Chapter> ——————–