Jessie Ch 8.4 – Closer Than Ever


“Tell me again why we’re doing this?” he asked, almost under his breath, as the two of them hopped off the bus.

“Because, Jessie, you don’t have any proper underwear,” Ashley said matter-of-factly as if the answer was obvious.

“But did we have to go to the mall to do it? It’s just so… public.”

Jessie looked up from under the bill of his baseball hat to see the wide looming entrance to the shopping center that seemed to him like a monster that fed upon the many shoppers pouring into its mouth. The more he thought about it, the more he decided that was about as accurate as it could be.

The corporate creature fed on people by the hundreds and yet it could never be satisfied. And here Ash was, ready to throw Jessie into the gaping maw sacrificially. And why? Because he was on his damn period and needed some clothes.

“Relax, it’s not like anyone’s going to recognize you. We came to Loston for a reason.”

“That’s what I’m afraid of.”

Jessie hadn’t told Ash that he was from Loston, a town quite far from Pierce Private Academy. This is where he grew up and where he spent his worst years. Should he tell her? What if they ran into some people he used to know? The thoughts danced across his mind as they entered the mall.

He tried to reassure himself that nobody would recognize him in a hat and baggy clothes, but he couldn’t shake the feeling that something bad could happen. Of all the places they could have gone, they went to the biggest hangout spot in his old town.

Jessie made sure to keep his head down as they bobbed and weaved through the crowds towards a big flashy clothing store that caught Ashley’s eye. The windows were lined with the hottest new outfits that the mannequins could muster, begging for acknowledgment lest the plastic people come alive and start killing for the attention they desire.

“I’ve gotta stop watching British sci-fi before bed…” Jessie trailed off, staring at the displays.

“What?” Ashley asked, wondering why he’d stopped.

“Oh, uh, nothing. Sorry.”

With a tug on Jessie’s arm, Ashley pulled him out of his thoughts and into the store.

“People are staring…” Jessie noticed as they wandered their way to the lingerie section.

“It’s because you’re dressed so weird. What’s with the getup?” she responded without looking away from the racks.

Jessie decided it was time to come clean. The sooner she knew, the faster he might be able to get out of here. And the faster he got out of here, the less chance of someone bumping into him.

“I used to live here,” he sighed, “and I don’t want to be recognized by people I went to school with.”

“Hate to break it to ya kiddo, but you stand out like a sore thumb. The outfit isn’t helping.”

“W-what? How do I stand out?” he had to keep himself from shouting.

“It just looks strange on you. You’re slender and feminine and those ugly baggy clothes just don’t suit you at all. That, and wearing baggy stuff and acting so weird and fidgety is just drawing more attention to yourself. The staff is staring because they probably think you’re a shoplifter.” She had to stop and point to the girls at the counter who awkwardly turned their eyes when they were caught staring.

Ashley had a point, he did look a bit suspicious sulking around and following his friend. But did she have to add that he was still girly? He’d bought a breast-binder and tried his best to look cool. Did she even notice?

“What is it about me that looks girly, huh?” he asked.

“Well…” she finally turned to face him, giving him a once-over. “You’re shorter than me, you have a cuter face than me, and without the hat,” she paused, pulling it off to Jessie’s dismay, “you have a cute pixie cut going on.”

“It’s not a pixie! I’m a guy, guys are supposed to have short hair!” he whispered, embarrassed to be overheard.

“And who told you that? Guys can have long hair just fine. You don’t have to force yourself to be such a stereotype. Just be yourself and stop trying so hard. And what kind do you prefer?”

Ashley ended the conversation by holding up two different types of panties, one far more frilly than the other.

“…I told you, I wanted boy briefs,” he quietly seethed.

“And that’s what these are, boy-cut briefs,” she said, pulling the frillier pair away and handing the others to Jessie.

He didn’t know what to make of them. Sure, they looked like boy briefs a bit, but there was no opening in the front and they had cute patterns running down the sides.

“…Do I have to wear girls underwear?” Jessie sighed, already accepting the inevitable.

For five days a month, ya do,’ Ashley’s mind retorted immediately, but the tone in Jessie’s sigh made her think twice. “Not necessarily but we’re here, those will work, and they’re eight for twenty-five dollars. There’s a bunch of different colors and patterns, too. Take a look.”

Ashley pulled him by the arm to face the bin full of underwear in a handful of sizes and a truckload of colors. His embarrassment was getting the better of him but Ash tried her best to help calm him down by putting her hand on his shoulder. It didn’t help.

“Just pick out eight you like. They’re all the same cut so focus on the designs, ok?”

Jessie didn’t need to. He just wanted this part of the trip to be over as fast as possible, so he grabbed a few random pairs, making sure to get nothing pink or overtly girly, but one pair caught his eye and made him flinch. They had a light blue trim and, on one cheek, a matching bunny drawing printed on the fabric.

“That’s… kinda cute…” he whispered aloud without realizing it. “It looks like my rabbit at home…”

“You have a pet bunny?!” Ashley squealed, nearly jumping at the potential of cuddling a cute little fluffy animal.

“No, no, it’s a stuffed animal. One I’ve had since I was really little. It’s the same shade of blue, too.”

“Then you owe it to your bunny to buy those!” Ash demanded.

Together they gathered their booty and made their way to the register, Jessie blushing all the way with his eyes down on the ground. Several minutes and two bags later, they were out of the store and Jessie finally caught his breath at a bench.

“I can’t believe I just bought panties. Me, Jessie Oliver, panty-owner, heh,” he sighed.

“What’s so bad about that? It’s just underwear,” Ash said, joining him on the bench.

“It’s the principle of the thing. I just… I’m supposed to be a guy, y’know? And here I am having to buy form-fitting girl-underwear because of my…” he looked around making sure no one could hear before whispering, “my period.”

“I already told you, it’s nothing to be ashamed of. We all go through it. The hard part’s done, though. We can enjoy the rest of the afternoon exploring! We could try on clothes, get something to eat… it’ll be fun! And it can cheer you up!”

Jessie couldn’t believe how cheery this girl could be. It’s like nothing in the world could get her down.

“…sure, as long as I don’t have to try on girly stuff,” he sighed.

“We’ll see.”

After several minutes relaxing at the bench, the ‘girls’ were off again, first stopping to grab some cookies from a nearby shop to have a little snack as they wandered the crowded white walkway between shops.

They passed The Edgy Emo, a store specializing in black studded clothes, belts, and pop-culture printed shirts that Roger would have felt right at home at, or so Jessie thought. He didn’t stop long to stare at the dark cave of depressed middle schoolers for very long before Ashley pulled him away towards a video game store just a few shops down.

“You’re into video games?” Jessie asked, surprised as ever, and yet somehow the idea seemed to fit Ashley.

“Yeah, why not? We won’t be in here long, I promise. I just wanted to see if they had any cheap used stuff I might like.” She bee-lined towards a wall near the back, past the kids playing the demo units and still more kids crying at their parents to buy them games.

Jessie didn’t feel as anxious in a place like that because, in a way, games were like books. His little brother had always been excited for whatever the most recent console was or whatever the hottest new online shooter was, but those sorts of games never appealed to Jessie.

He’d yet to find one that could really draw him in, but from the few people he’d talked to at school, it seemed like some games could be just as rich as books for some people. In a way, he’d found respect for the medium despite never giving it an honest try beyond the occasional time-waster.

He began making his way to Ash’s side as she moved mechanically through shelves lining the wall, occasionally grabbing a box and reading the cover before putting it back and muttering to herself under her breath.

“Found anything neat yet?” he asked, folding his hands behind his back. He didn’t really know where to be looking, so he opted to just stand by Ashley as she browsed through the hundreds of game boxes. “There are more games than I thought.”

“Heh, and this is just one platform. There are so, so many more, especially if you go back in time a bit. Do you have anything?”

“Any what?”

Ashley turned to look at the confused boy standing behind her. “Any systems, man!” she cried. “C’mon, you must have something, right? Everyone does.”

“Uh, well, my brother has a Super Playtendobox 64 or something…” he faltered, trying to remember the name of the console. Ashley, and everyone who overheard Jessie, facepalmed at the statement.

“Oh Jessie, you can’t be that out of the loop…”

“You know I’m not really into games, Ash.”

“But you like reading, right? What about an RPG?”

“A what?”

“A role-playing game. The type that’s got a heavy story and the gameplay is all in the battle system. You’re basically just moving from plot point to plot point, saving the world or something. If there’s any game you might like, it’s an RPG. Or I guess that Liz Darren game that’s coming out, but that won’t be for a while.”

Jessie perked up at hearing the name of his favorite book’s protagonist. “There’s a Liz Darren game, too? What sort of game would that be? An RPG?”

“No no, it’d be more along the lines of those Tomb Charter and Unraided games. You’ve heard of those, right?”

“I think I’ve seen Jason playing one before. There’s one with a girl who climbs a lot of stuff and then shoots people, right? Sassy old father-figure guy follows her around everywhere?”

“Yeah, that’s the one. What’d you think of that?”

“Well, it looked fun I guess, aside from the killing people part. It was like a big action movie.”

“Yeah, but the story was good, right? It’s right up there with Liz, just with a lot less detail. I assume her game will be like those.”

“But with less killing,” Jessie was sure to point out. That’d be very out of character for his favorite heroine for her to just be mowing down wave after wave of people.

“Naturally. Until then, try…” Ashley trailed off, moving to the next wall and quickly scanning the alphabetically aligned shelves, pulling a box out, and returning to Jessie, “this one. It’s for a portable, so you can just borrow mine and keep it in your room.”

“Is this an RPG? What’s it like?” he asked, taking the box and giving it a once-over.

“Yeah, and one of the best ever made. It’s an old game but they updated it for this version. It’s about a mute girl who runs into an excentric prince, but he doesn’t tell you he’s a prince, and then they meet up with her childhood inventor friend and then there’s time travel and these people can use magic and–”

“Ok ok, I’ll give it a shot. You don’t have to spoil it for me,” he said, cutting her off.

“Heh, sorry, I got a little excited. I just really love that one, is all. And it’s used, so it’s cheap. I’ll buy it if you want, I wouldn’t mind having the portable version for myself.”

“No no, that’s ok, I’ve got plenty of money. I work all the time and don’t really do anything with it.”

“Well be careful, Jess. If you get hooked on this stuff, say goodbye to whatever it is you’re saving for. What is it, anyway? College?”

“That or a car or something, I don’t know yet. It’s just nice to have money put aside and not have to worry about needing any, y’know?”

“…Remind me to hit you up next time I need a loan.”

“No way, you’d just buy this whole store and never pay me back!” Ash let out a hearty laugh at the idea and Jessie joined her.

After calming down, her smile never fading, Ashley grabbed a box off the shelf she’d been looking at earlier and they were out the door, each with a new game in hand. What they didn’t see was two boys staring at them from the opposite side of the demo unit they’d been playing.

“Hey, doesn’t that short kid look familiar? The one in the hat?” the taller of the two said to the shorter.

“I guess a little bit, now that you mention it. Do you think… could that be Jessie?” the shorter boy replied.

“Yeah, it does kinda look like him, huh? Should we go over and say hi?”

“No way, Brett. If that is Jessie, I think we’re the last people he’d want to see. He probably hates us for what happened last year. Remember?” he said, going back to his game with a sigh of guilt.

“Oh yeah, I almost forgot about that. But we’re not to blame, right? It’s not like we made him dress like that in front of the whole school.”

“Yeah, but still. Isn’t that why he transferred? Pretty sure he’s holding a grudge.”

“I bet you’re right,” the taller boy said, returning to the game alongside his friend. “It’s a bit of a shame, though. He was really cute wearing that. Almost like a real girl.”

“Dude. Gay.”

“What would be gay about it if he was a girl?” No reply. A moment passed with only the sound of buttons mashing and the din of the crowds before Brett suddenly paused and turned to his short friend. “Wait, what’s wrong with being gay anyway?”

“N-nothing, I just meant it as a joke. It’s just a saying. Everyone says it,” he plead, seeing the anger in his friend’s face.

“Then don’t say that like it’s wrong. That’s why we can’t have nice things.” After giving another dirty look to his friend, he turned back to the game and unpaused it.

Jessie and Ash passed by a few more shops, including a book store that cost almost an hour of time, and passed by a peculiar looking black stage in the middle of the floor with chairs all around it, but nobody there in the roped-off area.

“What do you suppose that’s about?” Ashley asked as they passed by.

“I have no idea…” Jessie trailed off. “Must be an event or something.”

“I guess so.”

The two had found another bench to take a breather from exploring after grabbing a couple of drinks. As soon as they sat down, though, Jessie dug out the video game he’d bought and started reading the manual, to get an idea of how to play something so completely new to him.

Ashley sat quietly for a moment, sipping her straw as Jessie read, but was quickly bored by waiting around. It was nearly lunchtime and aside from the underwear, she hadn’t done any real clothes shopping at all, which was her whole reason for coming along. That, and to find a new game to pass the time.

“So, hey,” she started after a few minutes. “Do you want to go try on some outfits next?”

“No,” he sternly replied, not looking up from the manual.

“Why not? C’mon, it’ll be fun.”

“You’re just going to make me wear girly stuff, and I don’t want to do that.”

“It’s not my fault if it looks good on you”

Jessie frowned, closing the booklet and turning to glare Ash in the eye, but not saying a word.

“Oh come on, I was just joking. Why does it make you so upset? You didn’t seem to mind it much before, but then you went and cut your hair and are trying so hard to be a bro that you’re really not acting like yourself.” There it was, she finally blurted out the topic that’d been on her mind for a few days now. Ashley hadn’t exactly been dodging the elephant in the room all day, but she’d accidentally called it out before she could think twice about it and maybe plan for a better moment to bring it up. Might as well be now or never. “What’s going on?”

“Pff, you don’t understand. You couldn’t.”

“Doesn’t mean I can’t listen. Maybe just talking about it will help you feel better. Please, Jessie. I want to know what’s going on in your head but you keep pushing me away every time I mention something girly. Just talk to me.”

Closing his eyes and letting out a sigh, he decided he might as well. Ash had been the closest friend he’d made at Pierce and with how much she’d helped him with his biological issues, he felt he at least owed her some sort of explanation. It’s not just any friend who would buy him pads so he wouldn’t have to buy them himself. She’d been there to help him from the day they met, and he never could figure out why. Opening up to her was the least he could do. He didn’t want to lose his last friend.

“Well, it’s just that…” he breathed deep, trying to pace his thoughts, “All my life, people have looked down on me. Made fun of me. Called me all sorts of names and put me in a lot of… situations I didn’t want to be a part of, all because I looked like a girl.”

“Situations like what?” she dated to inquire.

“…I don’t want to go into detail, but I’ll leave it by saying I had to leave my last school and go to Pierce for a reason.”

“Sounds rough.”

“Yeah, it was. I spent all this time combating that treatment; fighting to prove to the world that I am a boy afterall. I spent years doing this, in every aspect of my life, so people wouldn’t look at me like that, and it never took. I tried to be myself while holding onto that image and all it got me was more namecalling and beatings and stuff like that. My parents always told me to just be myself, and that’s what it got me.”

“…I can’t say I don’t agree with them, but it’s terrible that we live in a society that punishes that individuality. Teenagers are horrible human beings.”

“You got that right.”

They paused in a moment of silence while memories raced through Jessie’s head. Memories Ashley immediately regretted bringing up, judging by the expression on his face. As guilty as that made her feel, she didn’t want to lose this rare opportunity to see what made Jessie tick. After a minute she pressed on as light-heartedly as she could.

“…So what caused the sudden explosion of broitude this week?”

“When the night of the carnival happened, I thought I could just go along with it like nothing had changed. I didn’t look any different, sound any different, and my chest is small enough that it’s not exactly hard to hide… so I kept going by that golden rule of being myself, and…” he stopped. ‘Jeez, should I even tell her? It’s so embarrassing…

“Go on, it’s ok,” she encouraged. She didn’t quite understand what her friend was talking about, but the only change she could think of was that Jessie’s parents learned he was a girl the hard way. They all had to acknowledge Jessie’s body in a very public setting, and as sweet as the moment was in Ashley’s eyes, she still felt as if she were partly to blame for making Jessie so uncomfortable.

Jessie felt a reassuring hand on his thigh and, his voice cracking a little, he continued, “L-last weekend I went out with Eric and Duncan to try and get them to be friends; to stop fighting with each other. But it turned out they were fighting over me.”

“Fighting over you?” she paused, wondering what that meant, but then it hit her. “OOOOoooohhh…”

“So I ran. I.. couldn’t ignore being a girl anymore. I thought I had friends but they only liked being around me because of what I am, not who I am.”

“IIIIIIII really doubt that, but continue.”

“Then shit really hit the fan that night when I ran into Rachel and her brother, and I-, er, they…” he choked, biting his lip in shame and hiding his face in his hands. “…stole my first kiss.”

“EH?! Really?! Wait, which one?”

“…both of them.”

Ash had to stop and think about that again before coming to a conclusion on her own.

“That’s… is Rachel a…?”

“No, no, she thinks I’m a guy. Er, KNOWS I’m a guy. Damn it, now I’m doing it too. I can’t even talk about myself as a guy anymore.”

“But her brother obviously doesn’t know. He’s definitely not gay. I’ve seen him around here and there and girls at school are always trying to watch him practice or ask him out but he just brushes them off. He’s pretty cold despite being pretty cute.”

“I disagree on both counts,” Jessie said, remembering how warm Daniel was when they first met in the music room. “He was really cool at first, but then at karaoke, he… did that to me. And then I ran into him at school right after Rachel asked me out.”

“No way! Did he recognize you?”

“Sort of. He thinks I have a twin sister now.”

Ashley couldn’t help but cough out a humorless laugh. “This just keeps getting more and more complicated, y’know?”

“Yeah. It’s killing me.”

“Well, let’s put your mind off it for now. There’s no one from school here and you’re pretty androgynous, so you can wear whatever you like and it’d probably look good on you either way. This is an instance where being yourself is the best way to cheer you up.”

“Were you even listening?” he wondered. “That’s never helped me.”

“But right now, right here, it’s just you and me. You don’t have to bro it up for me, and you don’t have to wear a princess ball gown either. I just want you to smile again, and being an angry ‘man amongst men’ clearly isn’t healthy for you.”

She had a point, Jessie thought, making him question his antics at school this past week. Sure, it was rocky at first, but the boys in class had generally been quick to adapt. He still got a lot of awkward stares from everyone in the other classes as he wandered the halls, and it was pretty annoying that he only got stares from the boys’ class and never from the girls’ class, but he wasn’t planning to have class with the girls ever again. His macho attitude also seemed to buy him some respect from the teachers, but at what cost?

He was putting on a front. A character he thought he had to play to fit in, and it was working, to an extent. But was he losing himself in that, just as bad as he was playing ‘Jessica’? Class with the girls as one of the girls was never uncomfortable, at least not after he got used to it. Not the way gym was with the boys. Maybe he was overcompensating a bit too much to make up for his lack of a manhood. He had one friend left and was constantly putting on this angry air at school to push people away, and really thinking about it, he was acting like someone he didn’t particularly like.

But what should he do? He put all this effort into re-imagining his persona to fit in as a guy, to be a guy nobody would want to mess with, and that left him with only one friend left. And she was clearly taking issue with it, too. ‘Not that I’ve ever had a lot of friends,‘ he corrected himself, ‘but it was… kind of nice there, for a while.

“…Why do you care so much about me?” he ventured, wondering why she’s stuck around despite his abrasive behavior and attitude at school. “What’d I ever do?”

Ashley paused and for just a moment and, just for a split second, Jessie thought he saw the light fade from her eyes as she turned pensive and stared off into space. She just smiled and calmly said, “Why, indeed?” and paused again before finishing, “We all have things we’d rather not be reminded of.”

People she’d rather not be reminded of.

Jessie was shocked to see Ashley pause and stare off into the distance. She didn’t blink and she didn’t seem to be breathing either. She was just lost in her own mind, in some distant memory. Jessie didn’t know what could possibly have triggered such a reaction from Ashley, but thought it best not to open a door that’d rather remain closed.

A moment of silence passed before Jessie stood up and held his hand out in front of Ash. “I think you’re right, these baggy clothes look awful on me. Besides, I have a date this weekend, I could really use a new outfit or two. What do you say?”

Ashley slowly snapped back to reality, focusing on the hand she was surprised to find in front of her face before taking it and standing up alongside Jessie. “Sure, that sounds good.”

Together, they went off towards one of the many clothing stores chosen at random. Really thinking about his situation made Jessie feel a bit better like Ash said, and he was glad to get a little closer to her. To have a friend he could really be that open with.

Though she didn’t say it aloud, Ashley was thinking the same thing. Finally, she’d gotten Jessie to open up a bit. She kept replaying the conversation over in her mind as they walked into a store, wondering at what specific moment she checked out, before one part caught her attention and made her suddenly stop and shout, “Wait, did you say you have a DATE?!”

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