Disclaimer: I do not own Oregairu

2 Years Earlier

Johannesburg Juvenile Prison, South Africa

Usually the missions are simple. Find the target and eliminate them by any means necessary. Unfortunately for Hikigaya, his newest target was an idiot and got himself thrown into a prison for minors. This complicated things greatly.

You see the target was 17 years old and has been charged with committing multiple acts of rape for a gang, because of his age and the nature of the crime the judge decided sending him to an adult prison facility was in order. Unfortunately, two prisoner transport buses had recently been stolen so the courts decided to put Hikigayas target in a Juvenile prison close to the court for 2 days while more buses were being imported.

After 48 hours the target would be taken to a proper prison where he can serve his sentence. Normally a random prisoner would be sent by the client to take him out, however the father of the target is a well-known government official and has arranged for his son to be put in a separate part of the prison away from the general population.

Once the target is there he will be untouchable, meaning Hikigaya has 48 hours to assassinate his target from inside the Juvenile Prison. If he does not complete the mission there will be no extraction and he will have to carry out his own sentence for the next two years.

Sensei Ryuzaki had already gotten Hikigaya booked for attempted murder, and because the South African legal system is such a mess, within a hours he was being processed.


Present day

"You coming?" Hiratsuka says walking down the hall.

"Yes sensei."

Hikigaya gets off the floor and catches up to her, once again smelling her hair.

They continue walking until they reach a classroom. Hiratsuka opens the door and Hikigaya sees a girl sitting in a chair reading a book, there is no one else in the classroom.

"Sensei, knock please." The girl says sternly. She has also long black hair but with red ribbons.

"Sorry Yukino but you take too long to answer." Hiratsuka says this as if they've had this conversation many times.

"Well maybe if-"

Hiratsuka cuts her off "Anyway Yukino, I have a request. This is Hachiman Hikigaya, he's new to the school and I'd like you to show him the ropes of being a high schooler and help him out where you can."

'This is ridiculous. Even if I was really here for school I wouldn't need this kind of assistance.' Hikigaya thinks to himself before turning to leave but he is stopped when his arm his grabbed by Hiratsuka.

"You're not going anywhere Hikigaya." Her face is serious but there is levity in her voice.

"Let him leave," Yukino says "I decline your request."

"What?" Hiratsuka asks. There is no levity in her voice now.

"When I joined this club, you told me I had the right to veto one in every 5 requests from you. I chose to veto this one." Yukino looks back at her book, as far as she is concerned the conversation is over.

"Yes I may have said that but can't you do this for me please?" Hiratsuka now clearly not happy with her own promises being used against her was almost begging Yukino.

"But why Yukino?"

"Why would I want to spend my time with this gross looking man, he's probably a pervert."

'WHAT!? I've done nothing!' Hikigaya thought to himself wondering why everyone seems to think of him as a pervert.

Hiratsuka sighs a long sigh in defeat.

"Sensei, if you want to help this man so much, why not do it yourself."

Hiratsuka turned her head and looked directly into the eyes of Hikigaya for a good 6 seconds before her frown turns to a smile.

"I guess you leave me no choice, Yukino." Hiratsuka says now somewhat cheerfully before walking out the classroom with Hikigaya following her.

The teacher shuts the door behind her and once again looks directly at Hikigaya.

"Since Yukino refuses to help you out with school, I have so graciously taken the burden of your problems onto myself." Hiratsuka gestures from Hikigaya then to the middle of her chest while saying this.

"Thanks." Hikigaya says looking to the side.

"So, if you ever need any help with your work or anyone to speak to I'm always available."

"Thank you, sensei."

Hiratsuka doesn't say anything for a good few seconds almost as if she is mulling something over.

There is dead air for a few more seconds before the older of the two decides to speak again.

"Hikigaya, I think it would be best if you gave me your phone number so I can keep in contact with you."

'This is excellent.' Hikigaya thinks to himself, it's clear he's establishing some kind of rapport with her. 'This mission might go smoother than I predicted.'

"Of course, sensei." He responds unemotionally.

They exchange numbers and add each other as contacts.

"And listen here Hikigaya, if you even try to send me something inappropriate I won't hesitate to show you why that's not okay." Hiratsuka raises her fist with a devilish grin.

Hikigaya can see the sun setting from the hallway the two are standing in. He decides now's a good time to go home.

"Sensei, you may think of me as nothing more than a loner pervert but I believe you are way off base and one day may even come to respect me." Hikigaya chuckles at that and starts to walk past her.

Hiratsuka puts her hand on his shoulder causing him to stop.

"If I really thought that badly of you, we would not be standing here Hikigaya."

"I could say the same, sensei."

After saying that Hikigaya heard her breathing change.

'Was that a compliment!?' Hiratsuka thought to herself. 'Was that inappropriate or am I misunderstanding!?'

Hikigaya then put his hand on hers, clutched it, then removed it from his shoulder, and once again started to walk off.

Hiratsuka now trying to hide her flustered state, walked off in the opposite direction.

'A pretty good day at school,' Hikigaya thought to himself 'and an excellent start to the mission.'


2 Years Earlier

In handcuffs, Hikigaya walks with about 50 other boys in a single file line. Usually he tries to not draw attention to himself but the colour of his skin is far too different from the rest of the inmates to go unnoticed. The line stops and a different guard walks up to the inmate and takes 31 of the boys onward. Hikigaya (along with 19 other kids) is told that this is their dorm, and that their curfew is 21:00.

"Failure to comply will result in punishment." The guard escorting them says this in 3 different African languages, as well as English. Then taps his baton

"Do I make myself clear!"

"Yes sir." The boys all answer individually in their respective languages. Hikigaya answers in English.

The inmates are uncuffed one by one and sent into their room. The door shuts behind them and is locked.

Hikigaya looks around the room, it is unclean and has a greenish tint. Everyone including him is wearing a navy blue jumpsuit, the clothes are clearly unkempt and unwashed. There are 4 bunk beds, some with blankets and some without.

'8 beds, 19 people?' Hikigaya knew the prison was overcrowded but this was crazy considering most of the inmates would have to sleep on the floor. He could only imagine how bad the other dorms were.

'Doesn't matter I have more important things to think about.'

Since the target is 17 years old, he's being kept two floors up.

'If I can get out of this room at night I could get to his cell and pick the lock, however the guards patrolling may be a problem. I could take the first one I see down fairly easily but if one of the guards further away decides not to fight and opts to sound the alarm, then I'll be in trouble.'

Hikigaya continues to think.

'The only time the older inmates and the ones from my age group see each other is when they eat, but there are tons of guards in the mess hall. If I even got up from my seat at least one of them would have their eyes locked on me. I can't do anything to upset the guards or they'll probably send me to solitary confinement. If that happens extraction will be impossible.'

Hikigayas planning is interrupted by two of his peers getting to an argument.

"That bed is mine! Stay off it."

"Fuck you asshole, find another bed!"

Hikigaya watches the two inmates be separated by their peers and then thinks for a bit longer, before deciding on a plan.


Present Day

Hiratsuka sat at home at her desk looking at her reports and marking things off a checklist. Even though today was the first day of school and there wasn't anything to grade, she still had to make sure the schedule for all her lessons was in order, then print all the work for each student and get all the information necesary to teach them how to do the work. It was a pain but Hiratsuka always told herself that what she was doing was noble: moulding young minds and creating a better future for Japan, however just because that's what she told herself doesn't necessarily mean she bought into to it. She knew full well in 10 years she would go to a mall and see one of her students manning a cash register. 'Not that there's anything wrong with being a cashier.' she thinks to herself 'I mean a job is a job, and someone has to do the low-income ones, but is it my fault if they're lives only turn out mediocre?'

Hiratsuka sighs. The question was rhetorical, but she still wanted an answer. She gets up from her desk and walks over to her bed tiredly falling down on it.

She looks at her watch.

"Almost eleven o' clock." Hiratsuka mutters to herself. Her bed is comfortable but definitely too big for just her. She looks around her room, it's plain as ever. The walls are light grey and the floor is made of wood. There is a small cupboard next to her bed with a lamp and her phone on top.

Hiratsuka grabs her phone and unlocks it to see if she has any new messages.

She sighs, then frowns.

Hiratsuka plays around with her phone and absent-mindedly opens up Hikigayas chat.

'It's okay to text a student to see if they're alright, right?' She rationalizes to herself. She looks at the chat for about 30 more seconds before deciding against it and locks her phone.

'Don't be stupid Shizuka Hiratsuka!' She continues to berate herself in her head until she hears her phone ding from a notification.

The phone is unlocked and she has opened Hikigayas chat in what feels to her like half a second. In reality, it was probably even less than that.

Hiratsuka looks at the chat confused. There was no text from Hikigaya. She backs out from the chat to see the text was from someone else.

'It's the guy that stood me up yesterday! How dare he message me! I bet he thinks he can sweet talk his way out of it and get me to agree to go on another date with him! What a pig I could never love a man like that!'

Hiratsuka now fired up and confident, says "What do you want?" to his "Hey."

Four texts later, she agrees to go another date with him.


2 years earlier

Hikigaya and his dorm-mates are on their way to the cafeteria to eat. There is a bit more freedom to walk as the dorms are right above the mess hall. Hikigaya makes his way over to one of the two kids that were fighting earlier.

"That totsi over there has been talking shit behind your back." Hikigaya says as he shifts his gaze to the other kid from the fight.

"He's a little bitch and he knows it." The shorter of the two is smug and clearly over-confident.

"Everyone's going to think you're the little bitch if you don't stand up for yourself and show that kid who's boss. Just looking out for you man."

Hikigaya gives the inmate some distance and observes him riling himself up.

Eventually they arrive at the cafeteria and take their seats. The older kids are on the far right of the hall whereas the younger ones stay to the left.

Hikigaya sits next to the taller kid from the fight and says the same things as earlier. This kid gets riled up as well.

'The plan is going smooth as ever.'

Scanning the cafeteria, Hikigaya spots his target.

'There are about 4 cafeterias in this Juvenile centre, each designed to hold 90 kids, however due to South Africa's high crime rate there are close to 150 kids per cafeteria. Once our time to eat is over, there will be a lot of people getting up and moving around, the guards will be too distracted maintaining order to notice me slip into the line for the older kids and because this prison is so poorly managed and over-crowded the guards wouldn't notice that there is an extra boy in the line. Thankfully puberty hit me pretty early, and my usual deadpanned expression isn't making me look any younger.'

Hikigaya looked over at the two kids that were arguing earlier. They are starting to get heated with each other.

"You're the only bitch here!" One of them yells.

"Say that again." The taller of the two says coldly pushing the other one to the ground.

The guards start to take notice.

The boy on the floor then launches at the kid who just pushed him. They begin to have a proper fight and inmates circle around him cheering.

Hikigaya reaches under the table and starts unscrewing a bolt with the side of his tray. Before getting put in the prison Hikigaya had looked up the type of tables used in the cafeteria and found that there was a bolt connecting the leg to the skirt. You'd never find it unless you knew it was there.

Even though Hikigaya only had a few hours to prepare he had a fair bit of contingencies just in case his main plan fell apart. Getting out of the cell at night would be difficult due to the patrols and he'd have to bump a key off a guard, which in itself could get tricky, however it was possible and if that's what it took he'd do it.

Hikigaya continued unscrewing the bolt as the cafeteria got louder with cheers and yelling.

'No need to worry at the moment, the plan is going fine, if I can get the bolt out in time and get to my targets line then everything will be perfect.'

The bolt loosens and Hikigaya pulls it out, he uses his teeth to make a small tear on the inside of his jumpsuit and the slides in the weapon.

At this point the guards have broken up the fight and some of them are banging their batons on trays trying to get everyone to go back to their dorms.

'This is my chance.'

Hikigaya heads over to his targets line pushing through a bunch of hyped up sweaty teenagers.

The guards lead the line back to the dorm paying no attention to the assassin amongst the inmates.

Once locked inside Hikigaya makes a place for himself in the corner, eager to complete his mission. Sensei Ryuzaki would be visiting him tomorrow, if the target is eliminated by then arrangements will be made to have Hikigaya removed as soon as possible.

"Who's that Chinese kid in the corner?"

"Never seen him."

"Yeah now that you mention it he does look new."

Hikigaya ignores them.

"You wanna go show him a good time ayy Thando?"

"Yeah."


Present Day

Hikigaya wakes up early, getting in some push-ups and breakfast before taking a bath and preparing for school.

Hiratsuka also wakes up early. She eats her breakfast then goes to take a shower, whilst inside she looks at her shampoo. She has two bottles. She can use her regular one or try something new.

She decides trying something new wouldn't hurt. While shampooing her hair she wonders what it'd be like to have someone wash her hair for her. She never had anyone do it for her, and always felt like she was missing out.

'It must be nice.' Hiratsuka thinks while using her new shampoo. She frowns. 'Maybe my date with Shuu will go better this time, maybe he'll even show up. Then he can come and wash my hair for me.' She smiles to herself, imagining her perfect date.

At school Hikigaya sits alone at his desk reading a light novel as Hiratsuka does the register. Occasionally she'll glance over at him wondering if he's making any friends. He's not.

'Maybe if you didn't spend your time reading trashy books you'd be more popular.' Hiratsuka thought to herself ignoring the stacks of manga and empty cigarette packs in her desks drawer.

The day continued as usual. Hiratsuka had other students to care for and Hikigaya had other teachers to deal with. It wasn't until school was over they saw each other again.

Hikigaya was walking from his class to the exit whilst Hiratsuka was walking from a another class towards his.

Both see the other walking towards them and their eyes lock as they pass by with no words.

Hikigaya stops.

"Sensei?"

Hiratsuka stops as well.

"Yes?"

"Your hair smells different."


Authors Notes: What's up everyone, so it appeared the first chapter sparked some interest in people which is great. At this point, you've probably read chapter 2 so feel free to tell me if you like the flashback format. I think it helps pace out the story so things in the present day don't move too fast, plus I have a lot of ideas for 8mans adventures pre-Hiratsuka. Anyway I'll guess I'll address some possible questions you may have.

"Why is 8man 14 years old?"

The answer is I don't know, I just chose an age that I thought would be good, however if it is a big issue for the 'realism' in the story I'll figure something out.

"Will Yukino and Yui be in this story?"

Yes but 8man and Hiratsuka are the main characters.

Anyway if you have any other questions leave them in reviews and I'll answer them in the next chapter.