Jessie Ch8.2: The Fresh Prince of Pierce


A car pulled up to the school and out stepped a short, baby-faced punk with short gel-mussied hair and a devil may care attitude. His khaki slacks were pressed and his shoes shined to perfection. As he walked past the fountain and the delicately landscaped bushes, all the guys arched their brows and all the girls whispered amongst themselves at the sight of the mysterious boy’s swagger.

With his blazer cavalierly held by two fingers over his shoulder, he sauntered down the path to the school like he owned the place. Passing by two girls who stared, he slicked his hand through his hair and made a gun with his finger.

“Lllllllladies~” he quipped and with a click of his tongue, fired the imaginary gun. The girls blushed at the shot of love and ran off giggling. “Oh yeah, I got this.”

Eric arrived at the classroom once more to find Jessie still hadn’t shown up. ‘This is the second day in a row… where could she be?‘ he worried. ‘I guess she’s taking it pretty hard.

Eric had just settled down into his seat when the classroom door swung open to welcome the pimp among pimps, the fresh prince of Pierce himself, Jessie Oliver.

“Sup bitches,” he said to curious stares, lifting his head in a sup nod, a move he thought was an aggressive show of dominance that he’d seen a dozen times from the more insecure of his male classmates.

The class stared in silence. No one knew how to interpret the sight before them. The rolled up sleeves, the loose tie, the short hair, and the look of indignation on Jessie’s face was just too hard to comprehend. Their princess was no more.

“Aight, aight, take a picture, it’ll last longer,” Jessie said before swaggering his way over to his seat and plopping down. He leaned back in his chair with his feet kicked up on his desk.

Eric picked his jaw up off the floor and walked over to the would-be baller.

“Hey, where have you been? Are you ok?” he carefully asked.

“Yeah, what of it?” Jessie just sneered at him.

“Well, I was– Duncan and I were worried when you didn’t come back to the dorms on Saturday.”

“Pff, ain’t no thang. ‘Chyu worried for? You gay or somethin’?”

Eric deadpanned in disbelief. “…You know I’m not. Why are you talking like that?”

“Like what? A man’s gotta talk like a man if he’s gonna earn some respect and I’ve been disrespected ’round here way too much. It’s time that changed.” Jessie glared at Eric as he spat the words. A piercing glare that shot straight through him. Jessie was clearly holding a grudge.

“Whatever,” was all he could muster before heading back to his own seat.

It wasn’t long before the bell rang and Mr. Schroeder began urging the class to calm down. He raised an eyebrow when he looked up from his desk to see Jessie’s new look, but only asked him to sit properly before he addressed the class as a whole.

“It’s October now,” he started, “and as some of you might remember from last year, that means the annual Harvest Ball is coming up. And, since we’re on the subject of school events, I might as well remind everyone that the school trip is scheduled for winter break at the start of December. Looks like we’re heading to a ski lodge, if I’m to believe the talk around the teacher’s lounge.”

“How the hell are we supposed to find dates in time? We only see the girls in gym or after school,” one boy responded, joined by agreeing nods and shouts from others.

“Well you can start asking today, then. I’m sure the girls in Stable’s class were told today as well.”

“Nah, don’t deflect it like that, seriously- why are the schools not mixed? What’s the point? We have all the same classes and hell, even Jessie does gym with the girls,” the boy shrugged, pointing in Jessie’s direction.

“H-hey! That’s only because HE made me! And believe me, it’s never happening again!” he shouted back, much to everyone’s surprise.

Mr. Schroeder was perhaps the most shocked by the sudden uncharacteristic outburst from the usually quiet and shy kid.

“Is that so?” He asked, crossing his arms. “Did you get a proper gym uniform, then?”

“Yeah, bought it yesterday. I can’t believe I let you humiliate me like that to begin with. I’m not putting up with that crap anymore.”

Jessie tried his best to stare down his would-be enemy but Mr. Schroeder was more surprised by his sudden backbone than intimidated by the cute puppy’s growling.

“Well well, seems our princess has become a prince. Do as you like, I don’t care.”

“Good,” he said in a huff, plopping back into his seat and scowling at some far-off object beyond the window.

“The schools aren’t mixed because that’s how the school founders wanted it,” Mr. Schroeder said, turning to the boy who posed the question. “It keeps the focus of the class on education without the distraction of horny pubescent teenagers ogling each other.”

“Then why is gym always mixed with Mrs. Stable’s class? That doesn’t make sense! Doing gym with the girls, seeing how their stuff jiggles as they run… that’s way more teasing than just having them sit at their desks in the same room as us,” the boy shot back.

“Yeah!” the class cheered.

“I can’t say I don’t agree, but that’s just how it is for now. If it’s honestly that big of a deal to you all, talk to the student council and they’ll bring it up to the powers that be.”

The boy sat down and the room filled with chatter on the subject until the bell finally rang, signaling the change of classes.

“Alright, you know the drill. Hit the lockers and I’ll meet you in the gym. I have to run to the office really quick so start without me. Split up into small 2-on-2 teams for basketball and if you have odd numbers, just throw that person in a random team as an alternate. I’ll see you in ten minutes.”

Jessie strutted along as the boys all filed towards the locker rooms, never once faltering. He took with him a small duffel bag, which no doubt held his new gym attire.

Eric, on the other hand, was a bundle of nerves at the idea of Jessie changing with them. ‘What if they find out he’s a girl? What would they do to her? More importantly, what the hell has come over her today?!‘ he thought to himself, looking around to meet the eyes of the other students who were just as curious, if not as worried.

Jessie casually pulled up to a locker that’d been empty and, pulling the clothes out of his bag, stripped down to his muscle shirt and boxers. The thick binding tank top provided him a perfectly flat chest, much to Eric’s curiosity, and within moments Jessie was decked out in the loose-fitting boys’ gym attire.

“What are you all lookin’ at?” he shouted when he noticed everyone had stopped to watch him change.

They all snapped away immediately, going back to their own tasks in a fluster.

When they entered the gym, the girls were already there on the opposite side of the courts, playing at five or so of the many retractable basketball hoops that lined the walls. Many of them stopped to watch the boys enter the gym, giggling amongst themselves and gossiping about who they might ask to the dance.

The furor didn’t go unnoticed by Mrs. Stable, who looked towards the gaze of her flock to see a rather peculiar sight.

“Well that’s quite odd… I wonder what made that kid switch sides…” she murmured to herself.

“Seems the odds have turned in my favor!” a voice called from Mr. Schroeder as he approached his other half. “He strode into class today like he’d been reading a manual on how to be a man. You should have seen it, it was hilarious.”

Mrs. Stable grinned at the picture that filled her imagination of poor little Jessie trying so hard to be a man and failing in the most adorable way.

“As funny as that sounds, I still feel bad for laughing. That kid’s probably got all sorts of gender issues to deal with. Is this a cry for help? Should we maybe send him to the guidance councilor?” she replied.

Mrs. Stable may have had an open bet running on the strange student but that didn’t mean she didn’t care about Jessie’s well-being. If Jessie was seriously struggling with something, Samantha would have preferred he talk to someone rather than bottle it up, but she wasn’t about to broach the issue directly for fear of rejection.

The timing just isn’t right,’ she thought to herself. ‘But I’ll probably have to have a one-on-one with the kid eventually.’

“Hmm… I’m not quite sure yet. He needs to find himself and as long as he doesn’t burn the school down trying, I think it’s best we let him deal on his own for now. Let him come to us.”

“I hope you’re right,” she sighed. “But I’m going to get that five bucks, y’know. Try as he might to lie to himself, I still think he’s probably a girl. Even if he doesn’t know it yet.”

“We’ll see about that,” Mr. Schroeder smirked.

Meanwhile the girls had turned their attention to the familiar looking new kid on the other side of the gym; his cool confidence radiating across the hall.

“Who is he? Doesn’t he seem familiar?” Kate asked no one in particular.

“Must be a new transfer. We always have gym with Schroeder’s class,” Sherry replied, taking the bait.

“And with Jessie missing today?” Kate realized before her own words caused an epiphany. “OMG, don’t they look alike?! Do you think she’s got a brother?!”

Ashley, overhearing the ball-hogs on her court, sighed when she recognized the situation for what it really was. “I wouldn’t be too sure of that…” she said before hiking off to Jessie’s court.

He jerked to the side, dribbling the ball around his opponent while his teammate blocked, and found an opening. He jumped, carefully aiming his arc, and fired the ball only to have it bounce off the backboard but his teammate Jack was literally on the ball and jumped for it, making the tip-in.

“That’s 12 to 6. Great teamwork, lil’ prince!” his new friend Jack cheered, sharing a high-five with his comrade.

“C’mon, no fair! My teammate sucks!” a boy on the opposite team said, earning a shout from his partner. “Best two out of three.”

“You’re on,” they replied in unison.

Back and forth they went with the ball, each team occasionally scoring a couple points. After a few rounds, they gained a spectator, but nobody seemed to notice.

“Oy!” she called from the side, hoping to catch Jessie’s attention. Sadly, he was too involved in the game to acknowledge the outside world.

OY!” she called again, louder. It didn’t take long for Ashley to get annoyed and yell even louder with a stomp. “HEY, JESS!!”

“’Jeff?‘ Ash knows him?” Kate whispered back to her friend, the two of which had been watching Ashley from across the gym since she stormed off.

“Maybe it’s her boyfriend,” Sherry quipped coyly, mostly in jest.

“No way, he’s mine!” a certain charming accent chimed in over the other girls.

“Hm?” Jessie turned, finally paying attention to the exasperated ponytailed girl.

“Look out!” Jack called, but it was a moment too late.

The ball came hurling out of nowhere straight into Jessie’s hip, knocking him right into the bleachers. The players all ran to help but it was Ash who got there first.

“I’m so sorry,” she said, helping him up. “Are you alright? Do I need to take you to the nurse again?”

Jessie groaned and rubbed the sore spot where his head hit the wood, replying, “No, I’m fine. I just… I think I’m going to sit the rest of this one out…” He used his other hand to rub the sore pain in his gut that suddenly came back with the fall.

“Alright, well as long as you’re ok… Take it easy there,” Jack assured. He and the two from the opposing team went off to find a fourth to continue the game, leaving Ash and Jessie to themselves.

He waited until they were out of earshot before snapping on her.

“Why is it when you’re around I always get hurt? If it’s not bumping into you at the fountain or falling down that stupid well, it’s being knocked into some damn bleachers…” Jessie berated.

Ash flinched at the unexpected attitude from her usually quiet friend and ducked her eyes down in guilt before snapping back, “Jeez, I said I was sorry, didn’t I?”

“Whaddaya want anyway? Shouldn’t you be prancin’ around with all the other girls?” Jessie snapped, still sore.

“You mean other girls like you? What’s with the get-up?” Ash fired back with hands on her hips.

“SHH! Keep it down, would ya? This is how I’m supposed to be, you know that! I’m a man among men! They’re even calling me a prince now!” Jessie said, puffing out his chest like a proud lion.

“Y’sure that’s not just because you’re too cute as a boy?” Ash’s sudden quip deflated Jessie’s ego in an instant.

“Sh-shut up! It’s because they respect me as the man I am!” Jessie struggled.

“Riiiiiiiiiight. So what’s with the sudden change? You weren’t like this when I saw you on Friday. Did something happen over the weekend?”

Jessie blushed as flashes of Daniel’s kiss appeared from his memory. “N-Nothing happened, this is just how I’m supposed to be! This is how I’ve always been. Lately I just seem to have lost sight of that is all. No thanks to you.”

“Or your parents. Or those boys you’ve been makin’ eyes at lately.” she spat back.

Jessie glared and with a steely growl bellowed, “I AM ALL THAT IS MAN!!” holding his arms in the air in a grand display of victory, earning dozens of stares of confusion from both sides of the gym and a single ‘HA!’ from Mr. Schroeder before Mrs. Stable smacked him in the arm.

Ashley was completely nonplussed by the statement.

Jessie’s triumphant pose was quickly warped when a strange look twisted his face and with a start, he glanced down at his leg. Ashley, confused at the sudden change of expression, followed Jessie’s eyes to a see a small trickle of blood running down Jessie’s inner thigh.

Ashley instantly blushed out of embarrassment for her friend. “Is that– can’t you feel it coming?! And let me guess, you’re wearing those stupid boxer shorts again, aren’t you?! Come on, we have to hurry before someone sees!”

Ash grabbed his wrist and dragged him to the door but didn’t make it through before they heard a shout from Mrs. Stable across the way.

“Where do you two think you’re going in the middle of class?” she shouted, curious to see what Miss Jones was planning to do with her strange friend.

“Meet me in the locker room– go!” she said in a loud whisper before pushing Jessie out the door and turning to meet her teacher. “H-He got knocked into the bleachers and I was just helping him to the nurse!!” she shot back, trying her best to hide her fluster.

“Don’t take too long, then!” the teacher shouted across the gym, and with that, Ash ran off to the lockers.

“That’s right, the two of them are friends, aren’t they?” Mrs. Stable pondered aloud, catching Mr. Schroeder’s attention. He gave her a quizzical look, so she explained, “Oh, I’ve just noticed the two of them hanging around a lot. I was thinking that maybe it’s good for Jessie to have a female friend, y’know? Someone empathetic to talk to.”

“If you say so,” Mr. Schroeder replied. “I was worried the kid didn’t have any friends, so I guess that’s a bit of a relief. And if she can help him, more power to her.”

“Yeah, for sure,” she agreed before they both went back to the books they were reading to avoid paying attention to the kids. Gym days were their favorites for a reason: neither really had to do any work.

Ashley entered the locker room but Jessie wasn’t at his row. It took all of two seconds to guess where he might be and, gathering some supplies from her own locker, she made her way to the bathroom where she heard muted sniffles coming from a stall.

“Jessie? It’s ok, it’s just me,” she said in a soothing voice. “Are you ok in there?”

Jessie stayed silent. Well, aside from the sniffles, at least.

“Did you forget what day it is? I get you’ve got some identity issues going on, but you can’t neglect your biological situation when it comes to something like this.”

“I didn’t know this would happen… My gut’s been hurting since Saturday afternoon and the thought did cross my mind yesterday, but I was hoping I was wrong. I never thought in my life I’d ever have my pe- m-my per-…” he crackled through sniffles.

“Period. It’s ok, you can say it. It’s nothing to be ashamed of, we all go through it, Jess.” she assured her friend.

They sat in silence for a minute while Ashley dwelled on a way she might cheer her friend up before remembering something important.

“Wait a minute, don’t tell me this is your first, is it?” she said in surprise, remembering the conversation between Jessie and his mother at the carnival. “Aren’t you fourteen?”

“Yeah…” Jessie sniffed. “I told you, I haven’t always been a girl.”

Ashley was just as confused as ever at the notion, considering the situation they were in, but decided not to rub salt in what was clearly an open wound for her friend.

“…we can talk about that later, when you’re feeling better.” After waiting a moment and getting no response from the bathroom stall, she continued, “On a hunch, I assumed you didn’t have any supplies so I went and grabbed some from my locker. What kind do you want?”

“Huh? Supplies?” Jessie asked, confused by the proposition.

“Yeah, pads or ‘pons. Pick your poison.” Ash dangled one package in each hand, shaking them on display over the stall’s door for Jessie to see.

“I uh…” Jessie trailed off, still unsure of what she meant. “What’s the difference?” He’d of course heard of the products before but never knew how they were used.

“Pads go on your undies to catch blood whereas the tampons catch it from the inside,” she candidly announced.

It didn’t take Jessie much thought before deciding on the less intrusive of the two. “Pad then, please.”

Ash pulled away the slender package leaving the small folded square for Jessie to take.

“Umm… how am I supposed to do this?” he called after tearing open the packaging and examining the cotton pad.

“Huh? You just take the paper off and put the sticky side down on your– oh, you’re wearing those boxers, aren’t you?” she remembered in the middle of her explanation.

“…they’re ruined.”

“Hold on, I have a solution for you. Temporary, but a solution.” Ash ran off leaving Jessie to stare at the messy remains of his boxers. He’d tried soaking as much blood out as he could with toilet paper but it was useless. There was no way he could hide the stains on laundry day, much less explain them. They were lost.

“Wear these. Stick the sticky side of the pad down in these, and they’ll keep it in place.” Ashley handed him an odd-looking pair of thick black panties under the door, which Jessie was reluctant to take.

“A-aren’t these your u-underwear? I can’t wear your underwear, that’s just too weird…” he blushed, but luckily it went unseen past the stall door.

“They’re compression shorts, you wear ’em over panties. They’re new, they’re clean, and they’re yours. You can pay me back later if you really feel the need to. It’s the best I can do for you right now since you have are those loose boxers. It’s either that or the tampon.”

Jessie weighed his options quickly before sighing and responding with a simple, “thank you.”

“It’s no problem. What are friends for?” she seemed to smile with her voice. “If you have any questions about anything, just ask. And here I thought I was a late bloomer!” she gently laughed, but it was silenced by the flush of the toilet.

Jessie emerged from the stall with a stained plaid bundle of cloth and wad of packaging in his hand. He met Ash’s concerned gaze with a pale look of defeat and, throwing the mess in the trash can by the door, went to wash his hands.

“I just… never thought this would happen to me. I don’t know what to do. I don’t know what to do with myself,” he sighed, not looking Ash in the eye.

“It’ll all be over soon. Meet me after school and I’ll give you some more pads to get you through it, ok?”

“Yeah, whatever.”

“…and I’m serious about the shorts,” she added. “I really don’t want those back after this.” She meant it in a playful tone but Jessie was really not in the mood for it at all.

Together, they left for the nurse’s office and after Ash told the nurse about the situation, she let Jessie lay for a rest on a cot behind a privacy curtain. Jessie sat up on the bed, propped on the pillows and grabbing his aching gut before Ash appeared behind the curtain and sat down next to him.

“I’ll come check on you after gym, ok? Just take it easy for now. And take this…” Ash said, handing him a little red pill and a bottle of water.

“What’s this?” he said, examining the pill.

“Just some ibuprofen to help with the cramps. Don’t buy that Bridol stuff, generic ibuprofen is way cheaper and has the same ingredients.”

“Bridol?” Jessie asked, opening the bottle of water and popping the pill.

“Y’know, Bridol, Feauxtrin, and Cramprin; that crap drug companies try to say helps with cramps and stuff? It’s just ibuprofen but they gave it a different name and charge way more for it so they can exploit women for more money. It’s a freakin’ scam.”

“HEAR, HEAR!!” the nurse shouted from across the room. “Fight the power, kid! Spread the word!”

Jessie and Ash couldn’t help but giggle at the sudden unexpected show of support from behind the curtain.

“Take care. I’ll see you later, k?”

“Sure. Thanks again, really.”

“What’re friends for?” With a smile and a pat of encouragement Ash left for the gym, leaving Jessie to take a much-welcomed nap.

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