#upstead x sister!reader

[sarahmadpeople]

Family Dinner

Summary: Halstead’s sister thought that this time, family dinner would be peaceful but boy was she wrong.

Pairing: Jay Halstead x Hailey Upton, Will Halstead x Halstead!Reader, Jay Halstead x Halstead!Reader

Characters: Halstead!Sister Reader (OFC), Dad Halstead, Will Halstead, Jay Halstead, Hailey Upton, Jay’s daughter (OFC)

Tags: light angst, fluff, brother love, family dynamics

Warnings: none

Word count: 1101

Disclaimer: i don’t own any of the characters and this is purely fiction but based on true event ✌🏼

a/n: first chicago med fic although i’ve been watching the series since forever,, jay and hailey have a daughter in here (they deserve so much),, sorry for any mistakes and hope you enjoy this short fic ~~

Masterlist

~

There’s no Halstead family dinner that’s uneventful and that includes tonight. Everyone’s here at dad’s home for our weekly dinner. Will was the one who insisted on having dinners like this to spend time together after dad’s narrow escape from death in the apartment fire (and to watch dad’s diet once in a while, not that Will would admit that).

Dad’s seated at one end of the table and Will at the other end while Jay and Hailey sat at one side of the table and Alina and I sat at the other side of the table. Alina is my niece, Jay’s and Hailey’s daughter, who’s turning 8 years old in a few months.

Our plates were all loaded up with food that Will and I cooked since we’re in-charge of dinner tonight.

“The mashed potatoes are so good! I’m guessing Evie cooked it?” Jay said, in between mouthfuls of mashed potatoes. I laughed, “That’s right, big brother, and it’s mom’s recipe so can’t go wrong.”

There’s a pause of silence after I mentioned mom but that’s normal, we all miss her. Trying to cheer the moment, Hailey complimented the pasta that everybody knew Will made because it was his go-to dish to cook (and his most famous in the family). Dinner resumed and everyone made small talks with each other.

“I want to eat bread with nutella,” whined Alina and I glanced over to see that her dinner was already half-eaten. “Go and take the bread and nutella from the kitchen,” I instructed and Alina smiled cheerfully, skipping to the kitchen and back to the dining table with said items.

I helped Alina to spread the nutella on the bread and continued eating my dinner. Not even 5 minutes later, Alina called out to me, “I want more,” so I said, “You can do it yourself, Alina”. I pushed the bread and nutella to her. I was about to continue eating when dad voiced out, “Why can’t you just do it for her? She wants to eat it.”

Before I could even answer, he continued, “Sometimes, I think that you don’t like Alina. The way you treat her at times is just uncalled for.” I looked at dad, was he being serious? Was he really going to talk about this during dinner? Granted I’m not the kind of aunt who’s lovey dovey with their niece but that doesn’t mean I don’t love her. I’m rough with her because she’s like my younger sister who can tolerate and even return that treatment to me. It was like your typical sister siblings behaviour. Regardless, it was a mutual agreement that we don’t upset each other while eating and dad being dad, went straight to break it.

“Dad, Evie’s in the middle of eating, she hasn’t eaten since lunch and was busy the whole evening, besides, Alina’s old enough to spread the nutella on her own.” I heard Will saying. I felt myself shut down, which usually happens when I’m upset.

“Yeah dad, Alina can do it herself, don’t be mad,” Hailey started before turning to me and apologised, “Sorry Evie”. I shook my head and smiled (more like grimaced) at her, whispering a short “it’s okay”. Then, before Alina could reach the bread, I took it and made one for her. My eyes got teary and I knew if I talked I’d cry so I whispered to her, asking if she wanted more. Alina nodded so I made another piece for her.

I went silent the entire dinner. Having lost appetite after what happened, I ate slowly and ended up picking half of what’s left on my plate. I felt Will nudging my leg from under the table and I looked up to see the concern in his eyes. I smiled and continued picking at my food.

One by one, everybody finished their dinner and I carried my own plate together with what’s left on the dining table to the kitchen. Tonight, it was also mine and Will’s turn to clear the dishes and clean the kitchen. So while the two of us were in the kitchen, the rest were in the living room watching tv.

“I’m sorry about dad. He shouldn’t have said that, especially when we’re eating.” Will said, starting what he hoped to be a conversation that I honestly was not in the mood for. I shrugged and replied, “Whatever, not the first time and i’m sure it’s not gonna be the last. Let’s just clear all these so we can go home.” My tone giving Will no room to retort or continue the conversation. So we cleaned in silence and soon dad’s kitchen was back to its original state, clean and tidy.

‘Hey dad, I’m gonna go home first. See ya around,” I didn’t bother to wait for any replies before heading out the front door.

“Evie!” I heard Jay called out and stopped. I felt Jay approaching before he entered my line of sight. “I want to apologise for dinner, about Alina and Dad. I know you love my daughter, no doubt about that. It’s not fair for dad to say that to you, after what you’ve done for Alina ever since she was a baby. I’m not excusing him but it’s not like you don’t know him, right. Please don’t let this be our last family dinner.” Jay said.

I scoffed because yeah, I know what dad is like, but I thought he could’ve at least spared my dignity over dinner. “Don’t worry big brother, I’m not gonna disappear just because of tonight. I’ve faced worst than this, and I’m sorry too about Alina, I could’ve just prepared more than one piece of bread and no drama would occur. It's my fault too.”

Jay laughed and shook his head, “Don’t blame yourself, we’re Halstead, what’s life without drama,” he paused, then continued, “Okay, not gonna keep you here any longer than you’d want, so see ya around kiddo, and wait for Will, you live with him,” Jay ruffled my hair and went back in. Seconds after, Will was rushing out of the house.

“You’re so impatient, lil sis, left me high and dry in there to explain to dad why we’re rushing back home,” I heard Will and rolled my eyes. As Will turned the car engine on, he looked at me and said, “Dad said he’s sorry for what he said just now,”

I nodded. I looked at the house dad stayed and thought about the people inside and knew that I wouldn’t change this family for anything, even with the baggage it comes with.

“Okay.”

~

thankss for reading!! ❤️

[marvel-and-chicago-fan]

Believe me 

Warnings: Bullying, Arguing,Yelling, Mentions of killing, (Mentions of running away?)

A/n:Just a heads up that there may be some spots that don't make sense because i keep forgetting to fix those spots but anyways enjoy the story

Summary: You get into a fight and none of your brothers believe you until Hailey steps in and comforts you and helps you and your brother's stop fighting. 

------------------------------------------------------------------------------

Word count: 2.0k

Flashback to 12 years old

This is my first time being in the principal's office and honestly I'm scared, not because I could get suspended but because Its will whos coming to pick me up. There's nothing worse than someone being disappointed with you than mad. Will’s the type of brother who will just be disappointed and give you the silent treatment, while Jay will yell at you like crazy, take away your phone, make you file papers at the district and even give you the worst punishments ever for this type of situation but Will is definitely going to yell at me and take away my phone for the rest of my life and i'm probably grounded for 8 years.

End of Flashback

Present time

Today was the day you were really really dead, you got into a fight with this one girl because she said something about your family and you couldn't let that slide so of course you stood up for yourself and your family and punched right in the face. 

The problem is when you tried to tell the principal what happened she didn't believe you because the girl you fought was the principal's niece and “she could never do wrong” or that's what all the staff thought. Everyone knew in school that she was actually the worst student there and she's a huge bully who's spoiled and gets everything she wants. There's even a rumor how the principal pays her teachers to give her good grades. 

***

You were sitting outside the front office when you heard two familiar voices, and immediately knew it was Will and Jay. Now you were in trouble with both your brothers, both of them here means you're probably never gonna see the day of light ever again.

Your brothers walk up to the bench outside the room and either side of you and they don't even speak to you or look at you. You're surprised Jay hasnt threatened to arrest you or put you in handcuffs yet, he's done that before but that story is for a different day.

“Hello Mr, Halsteads” My principal came out of the door. My brothers stood up and shook her hand.

You hated your principal, and she hated you. She always had it out for kids like you. Kids who were better than Milly. Kids who stood up for themselves from Milly. Most especially kids who Milly Hated.

Once you were all seated inside the office she started explaining what happened.

“Y/n got into a confrontation with a girl named Milly and ended up breaking her nose.” She explained.

“I am so sorry for Y/n’s behavior today. I will make sure that she will be punished.” Jay replied. “Well i'm not” You mumbled 

“She is going to be suspended for three days and when she returns she's going to have ISS for one week.” She said, “What, thats so fucking dumb she’s the one who started it!” You yelled

“Not from what i heard” She replied “Other kids said that you were bullying her and when she tried to say something you punched her”

“THAT'S BECAUSE ALL THOSE KIDS ARE HER FRIENDS.” You stood and yelled.

“We're going to be going now, I'm so sorry for her actions. Please apologize to Millys family for us, Thank you.” Jay said while we walked out the office 

“In the car now, we’ll talk when we get home” Will whispered in a yell. Although you couldn't care less whatever they were going to do. 

***

“FIGHTING Y/N? WE RAISED BETTER THAN THIS” Will shouts at me. “Well maybe if you would leave me alone you wouldn't have to raise me” you snort “watch your tone young lady” Jay points at me. “How about you listen to me, OVER SOME STUPID GIRL” I say, raising my voice to match wills.

“Thats it, give me your phone and everything else now.”Jay puts his hand in front of me “take it, i dont even want it anymore since everyones gonna blow up my phone about how i lost to fucking Milly Wilson” I say tosing it to the ground and heading up the stairs to my room. “I hate you more than right now than i hated dad, I wish mom was still around.

“You are done for Y/n Halstead you're grounded for two months, be prepared to be at the district and med everyday now” Jay speaks in a serious tone. 

“Don't slam that door Y/n halsted” Will yelled anticipating my move but i slammed the door anyways because i don't care. 

That's when I had enough, enough of the bullying, enough of school, enough of my brothers never being on my side. It started out with small things like pillows, and clothes, then it turned into hard things, shoes, books and even your computer and Nintendo that was lying on your bed. Your room looked like a tornado and a hurricane hit at the same time, and you just sobbed on the floor.

That's when you heard a soft knock on your door. “Go away” you sniffled. “Y/n/n, please open the door” that nickname? Only Hailey called you that you thought. “Come in”

Hailey opened the door and immediately looked around to find you in a corner sobbing. You looked so frail and broken when she saw you. As soon as she held you into her arms you broke down and spilled everything out in a jumbled mess. “It’s ok let it all out” Hailey said in a soft voice.

“No one ever believes me- i-i tried to tell them a-a-and they wouldn't believe me, sh-she was the one who hit me first. She said if i told anyone sh-she would get j-jay fired” You froze, you weren't supposed to say that…There was one thing you hadn't said and that was milly hit first when you tried to confront her on what she said

Milly said if you told anyone she would make your life miserable and she would get Jay fired 

from his job and arrested. 

You stood up from haileys grip and started pacing around your messy room “No,no,no Milly's going to get jay fired or probably kill me now i should probably run away to south america or something”

“Woah woah y/n calm down, what actually happened?” She questioned, and you just started explaining. “Milly said mom and dad deserved to die since Jay takes people away from their families and sometimes hurts them, so i went up to and asked her why she said and she just replied “Don’t put yourself where it doesn't belong, and boom she punched and i just defended myself. You probably can guess the rest.”

“Oh, Y/n its ok i will make sure that milly wont do anything to you or jay, i promise.” She cooed “You promise?” She gave me a smile and a slight nood. “So how about you stay at my place for the night and we can head to the district tomorrow

you packed your bags and headed downstairs with hailey in tow. "Where do you think you're going? Did you forget that you're grounded?" Jay stood up from his chair

i'm taking her to my house   no she grounded  hailey crouched down to your level since you were short for your age "why don't you take my keys and head to the car and place an order for some food" you nodded and left the apartment

"jay don't argue with me the least you could have done is listened and you couldn't even manage that" Sill stood up to back jay up but hailey immediately stopped him "Don't even, i will bring y/n  to the district tomorrow and you will both apologize and listen to her or else" Pointing to two men while walking out the door and slamming it behind her. 

***

It was now the morning and you and hailey were headed to the district. When you tried to close the car door you hissed and immediately pulled your hand to your chest. “What happened to your hand?” Hailey asked. “Nothing.” you didn't want to get into the topic of what happened. Lets just go to the district and get this over with.

“First of all i'm taking you to get your hand checked out and second of all i talked to jay, he's not gonna yell or do anything to you. He forgot that I have handcuffs and can arrest him” You chuckled at that last part, her and Jay didn't always agree. 

Hailey took you to Michigan Arial Hospital (the other hospital in Chicago since she knew you didn't want to go to med) and it turns out you had a sprain, well you had a sprain before but since you didn't get medical attention earlier you now broke your hand. You got a light blue cast because light blue was Haileys favorite color and at the moment you didn't want to please nor even think about jay or will. 

When you reached the district you said hi to Trudy and everyone else but you hid your arm because you didn't want to talk about it. “Hey, mini halsted” Adam greeted you. You didn't even reply and walked straight to the break room where Jay would be found since you didn't see him in the main area.

“Jay you will listen to every word this girl has got to say because if you don't, Voight’s standing right outside this door and he would love to hear how you're treating his Goddaughter,” Hailey says with a stern and serious voice.

All three of you sit down and you explain what Milly has been doing to you and everyone else in the school. And how Milly is the principal's niece so she never gets in trouble. You also get far enough to wear you explain why you currently have a cast on. “And she said if i ever told anyone she said she would get your fired and make your life miserable”

“Y/n- i dont even know what to say, i am so so sorry for not believing you when you first told us. I guess i was just mad you had gotten into a fight and i didnt think about anything else” Jay said as he pulled you into a tight hug

“Jay- careful of my hand” You gasped “and, i forgive you” you said with a soft sweet voice. 

“Now if you excuse me I've got some CCTV footage to look at.” Jay said as he pulled apart from the hug and stood up. You knew Jay was never the emotional type and never wanted one of his colleagues to catch him crying, yet Hialeys saw him cry Millions of times.  

As the team was going through the footage they kept backing up to the right spots until they reached the time of yesterday. Milly punching you in the eye, which explains why your eye looks a little swollen now. 

“THERE! Right there is all the proof we need to prove y/n innocent on many levels.” Haileys shouts. “Alright, find phone numbers, addresses, figure out her relatives before we go for her. I want to make sure this girl gets what she deserves” Voight yells in his raspy voice.

Definitely working on part right now, i must say this is my favorite one so far since i've planned it out i've wanted it to go. Don't forget to read my other stories and look at my crazy wattpad reading lists. Thanks :)

[anotheronechicagobog]

Chapters: 2/? Fandom: Chicago PD (TV) Rating: Teen And Up Audiences Warnings: Graphic Depictions Of Violence Relationships: Jay Halstead & Reader, Jay Halstead/Hailey Upton, hailey upton & reader Characters: Jay Halstead, Hailey Upton, Hailey Upton's Father, Hailey Upton's Mother, Ethan Choi, Reader, upton!reader Additional Tags: Abuse, Child Abuse, Implied/Referenced Child Abuse, Injury, Emotional Baggage Series: Part 2 of Hey There, Sister Summary:

Hailey hasn't spoken to her father since she was 18 and her mom since she was 20. A case in Greektown leads Hailey to a startling and terrifying discovery - she has a little sister, and their father hasn't changed one bit.

Hey everyone, my life has been absolutely insane and it interrupted my time and ability to write. So sorry for making those who were interested wait for this chapter, but I hope you like it regardless! 

[fangirlfrom-hell]

Remember that I'm stupid and accidentally delated my blog and lost all my fics 😭 I found some, and I'll be re-posting them during these days. I'm still positive I will find the rest.

Chicago PD Masterlist

Requests

Becca (Halstead sister) sees her father die

Halstead Sister

Big Brothers' Reunion Goes Worng

Can I do an Experiment?

A Day Full of Emotions

The Funeral

Cool Girl

October 1st and Traditions Gone Worng

Several Missed Calls and a Sprained Ankle

Absolution and Mercy (7x9-7x10)

Marigolds: A Day of the Dead Story

In trouble

Music Fest

One of those days

The Weight Station (S2x03)

Chapter 1

The Fragile Bonds

Part 1 Part 3

Part 2 Part 4

Upstead Daughter

Swearing Jar

When your Parents are Detectives you Gotta try Harder

Jay Halstead x Reader

How Many Detectives Are Needed To Sleep A Baby?

"My Daddy has to Fight Some Bad Guys"

Exciting

[deanstead]

RESA'S 3K FIESTA BINGO MASTERLIST

Posting the masterlist under the cut for all the fics under this so far! Bingo has been extended to 31 Jan 2023, so I'll continue to update as new fics come in as well! If your fic is not here, please let me know! Enjoy!

@resanoona

Supernatural Elements: There Will Be Peace (Dean Winchester x Reader)

Kids: A Girl (Will Halstead x Reader)

Snowed In: Snowstorm (Jay Halstead x Reader)

Fight that ends in a kiss: Hate Fighting (Adam Ruzek x Reader)

Hurt Feelings: News (Dean Winchester x Reader)

Fake Dating: Private Life (Jay Halstead x Reader)

Waking Up Next To Each Other: Our Little Secret (Adam Ruzek x Reader)

College AU: Change (Jay Halstead x Reader)

Sick/Illness: Vows (Connor Rhodes x Reader)

Hurt/Comfort: Bad Feeling (Matt Casey x Reader)

5+1: Five Times, and then One (Jay Halstead x Reader)

Neighbors: Spare Key (Connor Rhodes x Reader)

Kidnap/Hostage: Coming Home (Halstead!Sister)

Free: Christmas Surprise (Jay Halstead x Reader)

First Fight: The Good, The Bad, The Ugly (Will Halstead x Reader)

Facing Fears: Unknown Threat (Jay Halstead x Reader)

@sheetsonfire

Road Trip: Interstate Intimacy (Jay Halstead x Reader)

Woke up next to each other: Wrong Door (Jay Halstead x Reader)

Supernatural Elements: Thinning Of The Veil (Jay Halstead x Reader)

5 + 1: Five Times and a Date (Matt Casey x Reader)

Free: I Only Want To Be With You (Jay Halstead x Reader)

Fights that ends in a kiss: The Red Strokes (Jay Halstead x Reader)

Sick/Illness: In Sickness and In Health (Kelly Severide x Reader)

Weddings/Proposals: Suspects and Surprises (Jay Halstead x Reader)

Hurt Feelings: Free Will (Will Halstead x Reader)

Hurt/Comfort: Chasing Shadows Away (Jay Halstead x Reader)

@writercole

Kidnap/Hostage: Sacrifice (Dean Winchester)

Free Space: The Way You Look In Black (Dean Winchester)

5 + 1: A Guardian Angel and Her Knight (Jake Seresin)

@afriendlyneighborhoodhufflepuff

5 + 1: 5 + 1 (Will Halstead x Sylvie Brett)

First Fight: First Fight (Rheese)

Free Space: Quiet Nights (Brettsey)

Fake Dating: What Are We? (Will Halstead x Reader)

Sick/Illness: Sicker than a dog (Halstead!Sister)

@wordsandupstead

Bodyguard AU: Bodyguard (Upstead)

Facing Fears: Positive (Jay Halstead x Reader)

Sick/Illness: secrets, soup and sassiness (Halstead!Sister)

High School/College AU: there for her (Upstead)

@district447

Supernatural Elements: Prince of Hell (Kelly Severide x Reader)

@i-like-sparkly-things

Hurt/Comfort: Stay Awake (Burgstead) // Stabbed (Halstead Brothers)

@enchantedblackrose

Hurt Feelings: Not Pretty (Jay Halstead x Reader)

Free Space: Happy Birthday (Jay Halstead x Reader)

@i-spaced-sorry

Road Trip: Optimal Road Trip (Halstead!Sister, Upstead)

Coffee Ship AU: Coffee Shop (Intelligence)

@storiesofsvu

Neighbors: Start of Something New (Derek Morgan x Reader)

First Fight: Journey To The Past Ch 15 (Bryan Kneef x Reader)

Hurt Feelings: Journey To The Past Ch 16 (Bryan Kneef x Reader)

Sick/Illness: Dunbar Magic Hot Chocolate (Heather Dunbar x Reader)

Snowed In: Washington Whiteout (Elizabeth Keane x Reader)

Forced Proximity: Learn to Share (Emily Prentiss x Reader)

Hurt/Comfort: Iowa Chill (Heather Dunbar x Jackie Sharp)

[jayhalsteadsimp2019]

i have wips and ideas i just have no idea what to write.

would yall rather see halstead sister, upstead daughter au, halstead brother au or will halstead x ruzek sister? like idk

and i have two halstead sisters but they're kinda the same plot just a bit different

also I've started writing in 2nd person more, but the daughter au, the brother au, and one of the hasltead sisters are ocs. the other two are in 2nd person. all of them are basically wips except for the oc halstead sister

so yeah which would yall rather see?

[afriendlyneighborhoodhufflepuff]

Who I write for

Upstead

Stellaride

Brettsey

Matt Casey x reader

Halstead Sister

Rheese

Will Halstead x reader

Kevison

Halstett (Will and Sylvie)

[specialagentsoftie]

Faith | j.h. & h.u

*Gif doesn’t belong to me! Credits to the owner <3 Pairing: Jay Halstead & Hailey Upton x Sister!Reader Requested: yes by anon! "I saw you said upstead requests were ok so maybe imagine upstead talking about kids but there's a reader character in it somehow, maybe poly upstead? you can choose how to add it in ❤️" Warnings: none? Word count: 1.2k ish A/N: so this was a concept/drabble request... but it got outta hand. and its now just a shorter oneshot. i have so much respect for char x char writers bc idk how yall do it. jesus. idk what im doing lorddddddd

Y/D/N (your daughter’s name) was born 6 months ago and every weekend since she got here, Jay and Will would take turns visiting you to see what they could do to make things easier. You loved the help.

Jay didn’t start bringing Hailey by until recently, but you enjoyed having your girl time again. It had been a while since you had the mental capacity for it.

This week, you could tell that the detective had something on her mind. Between the baby questions and her asking you when you knew you were ready for a baby… all the beating around the bush, you just decided to get to the point.

“You and Jay ever talk about kids?”

“Yeah, we have. It's just that...Jay would be such a great dad.”

“I agree. We love Uncle Jay, don’t we,” you cooed as you shoveled mush into the baby girl’s mouth. “So what’s the problem?"

“I just— I don’t know. Would I even be a good mom? How would I know if I'm ready? If we're ready? Babies and I aren’t really on the same page… and the job..."

“Oh come on. Hailey." You can’t stop the scoff that escapes from your lips. "You never know if you're truly ready or not, but I’ve seen you with kids, you’re great with them.”

“Kids aren’t the same as babies, Y/N!"

You rolled your eyes, knowing damn well that Hailey Upton would rather chase down bad guys and put people in jail than hold a baby.

“They’re so little and fragile,” she whined, her face twisting in discomfort at the thought of dropping one of them.

“You wanna practice?” you asked as you held out your daughter for Hailey to hold.

You really meant to give her a choice, you think, but you’re placing Y/D/N in the blonde’s arms before she even gets a chance to answer.

A rainbow of emotions appears on Hailey's face from confusion to shock, to panic as she realized there was an infant in her arms.

You let out a chuckle as you watch her mouth something to your brother and awkwardly bounced the baby on her chest. It was probably something like “what am I supposed to do with this”, but you knew she’d get it eventually.

After all, who could resist the sweet facial features you and your brothers seemed to share? Your daughter was no exception to Halstead genetics.

Jay quickly raised his hands in surrender and left the room, that knowing smirk on his face telling his girlfriend that she was doing fine and to figure it out.

Just like you expected, it didn’t take long for Hailey to melt from the happy girl’s giggles. No less than 20 minutes later, someone wasn’t ready to let Y/D/N go.

“Are you ever going to give me my baby back?” You laugh as you see the pout appear on Hailey’s face, hugging the little girl tighter in protest. “I’m just kidding, Hails. I’ve got a couple more things to do before I’ll need the munchkin.”

“She’s just so cute, Y/N. Look at those cheeks. Look at that smile! Oh my god, she’s smiling at me.”

“What can I say, she loves her Aunt Hailey,” you say as you walk over to where Hailey was sitting with your daughter propped up against her legs. You can’t help but admire the sight for a moment, before leaning over the back of the couch and giving her a rub on the shoulders. “And for the record, I think you’d be a wonderful mom.”

Hailey turns at your words, looking at you like you couldn’t possibly know that. But you did because for some people, you can just tell. It's so obvious.

You could tell by the way she looked at your brother, how much love she had for him and the trust they had for each other. When Jay got hurt, she was right there by his side, every second of the day that he had to stay in the hospital.

There was no doubt in your mind that Hailey was going to be the best mom to their kids.

“Really?” she whispers, and the small nod and smile you give her made her heart soar. You didn’t need to say anything else, she understood.

Standing up to return to your chores, you plant a comforting kiss on the crown of Hailey’s head.

It was something you started doing after you had your daughter and Hailey shut her eyes at the feeling, thinking about how much your validation meant to her.

You, being the ever-observant baby of the Halstead family, were the first one to notice there was anything going on between your brother and his partner. Since day 1, you were their biggest supporter.

You and Hailey were fast friends and you always saw her as the older sister you never had.

“I’m gonna steal her,” Hailey calls to you as you turned your back.

“Fat chance, blondie!” Your voice echoes down the hall, leaving her to continue playing with your daughter while you got things done.

Hailey, too infatuated by the tiny fingers wrapped around her own, doesn’t hear the soft footsteps making their way over to her.

“See? Even my sister thinks you’d be a great mom.” Jay’s voice broke the silence as he walked into the room, taking a seat next to his girlfriend on the couch. "And Y/N would know because she's one herself.”

“You heard that?”

“Mmhm."

“That was a dirty trick you pulled back there, leaving me alone with this little squish,” Hailey cooed, her finger stroking Y/D/N’s chubby cheeks.

“I knew you had it under control. You always do.”

“How do you Halsteads have so much faith in everyone? You and Will, and Y/N definitely has it the worst.”

Jay chuckled to himself, knowing that you had always been the best pep talker, even when you were a little kid.

“Well, that’s how our mom was and Y/N is, without a doubt, her mini-me if I ever saw one. I just wish mom could have met you. She would have loved you, so much,” he murmured as his hand came up to cup Hailey’s jaw, running his thumb over her skin lightly.

She leaned into his palm as he turned her face towards him and brought her lips to meet his.

Nothing happened, but moms hear everything. Even the almost indiscernible moan that escapes from Hailey’s mouth as Jay bit her bottom lip didn’t go unnoticed by you… all the way from the laundry room.

“I swear to god, Jay, if y’all are gonna make a baby right now, get your asses outta my house please!”

“We should get out of here,” Jay whispered and the blonde nodded eagerly.

Jay got up from the couch with his girlfriend riding his coattails, finding you in the house in record time and handing you back your kid like she was a sack of potatoes.

Y/D/N was giggling like a maniac at her uncle's manhandling and you manage to shoot your brother a "really?" look before you're tackled by another person.

“Thanks for the baby fix, Y/N/N!” Hailey chirped as she wrapped you in a quick, albeit tight, hug and gave a peck to your cheek.

“Go.” You shook your head as you chuckled to yourself and the two were holding in their own laughs as they fled from your doorstep, hand in hand like they were teenagers again.

When did you become the mature one around here?

Upstead Taglist

@sylvieshay

[i-like-sparkly-things]

Just friends

A Halstead!Sister

“We're partners y/n. It doesn't matter if i like her, I don't know if she feels the same way about me !"

Requested : Yes by @allieoop1217 'can I request a Halstead!sister fic where she and Will make fun of Jay being totally in love with Hailey but won’t admit it? 🙂 '

Warnings : idiots in love, underage drinking, friends to lovers, scared to lose Hailey's friendship but Jay's just a dumbass, crack

Note : this took too long but I hope you like it!! its is pretty short and most of it is pure crack lmao 😅once again thank yall for being supportive of my grammar!!

MASTERLIST

---------------------

Your senior year was rough on you with the extra classes and the various coaching centers you had joined to prepare you for college .

But at least once a month you found time, to join Will and Jay for a Blackhawks game and Thai food.

You rang the bell to jay's apartment while trying to dust off some snow from your jacket.

"There you are" Will smiled as he opened the door.

You immediately hugged him, stealing his warmth ''hey''

Will chuckled, patting your back ''how are your classes going ?''

''Ugh, they're boring'' you pulled away ''it's like my textbooks never end'' You complained, making your way into the kitchen.

''Oh trust me, college is going to be a lot harder. You'll barely get the time to do anything'' Will said, following you through the hall after locking the door behind him.

You didn't want to imagine what college would be like, and honestly you didn't think you would survive if it wasn't for your extra classes and Will helping you with your quizzes and notes.

''Whatever I'm not gonna think about that now. I just wanna watch a game and have a beer''

''What?'' Jay turned from his spot at the table where he was unpacking the food, to look at you with wide eyes "you're only seventeen y/n, you are not drinking beer."

“yeah 'cause you and will never drank alcohol when you were seventeen” 

"she's got you there" Will shrugged, he would rather let you drink with him and jay than drink alone or with friends.

"Fine. One beer. And that's it."

You smiled.

Soon you had ditched your jacket and found one of jay's blue flannels for yourself .

You walked out of his bedroom making your way towards the couch where Will and Jay had already began to dig in.

"Hey , that's mine!" Jay accused, pointing his chopsticks at you.

"Nope —" you shrugged, as you squished between your brothers, Will handing you the container of Thai food "—it's mine 'cause I couldn't find the red one. Did you lose it or something?"

"What ? No..... Wait, Hailey must have taken it after she crashed here a couple of nights ago"

Your eyes widened at his nonchalant revelation as your mind did somersaults "Hailey what?"

It was pretty obvious that Jay was into Hailey. You, Will and intelligence had caught them staring at each other one too many times. The longing looks, the eye conversations, the 'are you okay's all seemed like something straight out of a romance novel .

But obviously Jay being Jay just had to make it more complicated.

You're stubborn brother absolutely refused to take any hints. Hailey would openly flirt with him and Jay would laugh it off. Adam and Kevin would send sly smirks whenever they caught a suspect together and he'd smile right back. Kim and Vanessa would holler at Hailey anytime she wore a dress to go undercover but Jay would hand her the mic, smile, and walk away.

Honestly at this point, Hailey could slap Jay straight across his face and yell "I love you" to him and you were sure that he would reply "but as friends, right ?"

All of his "detective" skills would fly out the window anytime Hailey came through the door.

"Oh yeah, it was a crazy case, so I told her she could spend the night, " he said, lowering the volume of the Blackhawks game and taking his the last sip of his beer "—and in the morning she took my flannel. That's all. "

You mentally face palmed at your oh-so oblivious brother and turned to Will only to be met with a similar expression to yours.

"Are you sure that's all?" You prodded, raising your eyebrows.

"Not with this again" he said, walking towards the kitchen counter "I've told you we're just friends"

"Oh my god! Just admit it Jay , you have a thing for her !!" Will stated, putting his food on the table in front of him.

"No , we're work partners and good friends. And we work well together. That's it" He popped his beer open taking a long gulps as if to drown his thoughts away "and talking about all this, y/n don't you have a crush on a guy in your class or something?"

"Nuh-uh!" You quickly interrupted "don't change the subject!!" You and Will promptly made your way to the counter, cornering Jay . "For god sakes, she almost confessed she loved you at the hospital"

"You don't know that. You don't know what she was gonna tell me "

"All you do is talk about her, jay! " Will chimed in "Whether it's here or at my place or at molly's— she's the only one on your mind"

Jay opened his mouth to argue— she wasn't the only one on his mind..... was she? No . He had a busy life. He did lots of things other than thinking about Hailey. He went to work— with Hailey, he realized. He often went to molly's after work as well …. also with Hailey, his mind told him. He went jogging and to the gym —and Hailey's accompanied him there too.

He scratched the nape of his neck and looked at Will who was giving him the 'i told you' so look.

He averted his eyes to his fingers picking the label of the beer "So what if I like her " he mumbled, sounding something like a shy five year old who admitted to having a crush on his classmate.

You and Will smiled knowingly, having waited two years for this moment to come.

"You have to tell her, Jay "

Jay's head snapped up looking at you like you grew three heads "What ?? No !! We're partners y/n. It doesn't matter if I like her. I don't know if she feels the same way about me !"

"Of course she feels the same way about you" Will deadpanned. "Just friends don't crash at each others places and go back home with their clothes.... wait.... some do.... But that's beside the point. 'just friends' don't stare at each other for eternity "

"I don't —"

"Cut the crap Jay!! What's the real reason you can't tell her? Why can't you just ask her out on a date?" You questioned.

"You don't understand. We put a lot of time and effort into our partnership and to gain each other's trust I-I just can't lose that "

"I don't date the people I work with" Those heart wrenching words circled his mind . He had gone through so many scenarios and thought about the hundred different ways Hailey would reject him. How his nightmares would become reality, if he ever told Hailey how he actually felt about her. She would leave intelligence and move to the FBI. She would run away from Chicago and away from him.

She would think that the only reason he got close to her, was to take advantage of her.

"You're not going to lose Hailey. In fact, if you don't do this, what you're going to lose is a future with her"

He hasn't thought about that. Jay never allowed himself to think that far into his life. He hadn't considered the fact that there's a chance that she really wanted to be with him— wanted to be more than friends.

"She's right man. I saw Hailey in the hospital waiting room. She absolutely refused to go anywhere until I gave her an update and she saw you for herself "

"See!! She's not going anywhere. All you have to do is ask her out on a date or even dinner!" You near pleaded until Jay caved.

He shook his head and put his beer down "Alright, alright. Maybe .... I'll ask her out "

"FINALLY!! " You hugged, nearly toppling him over.

"It's about time, Jay " Will grinned.

"Yeah, I know" He patted your back trying to get you to loosen your death grip on him "come on..."

"Now I can rightfully collect my money from Adam and Kev" Will said, but regretted it as soon as he saw Jay's wide eyes.

"YOU MADE BETS ON ME??" he asked in disbelief as the as you and Will shared sheepish looks.

"Uhhh..."

**************

If you enjoyed this fic, please reblog and comment !! You can also read more fics here!!

Taglist : @girlandthemoon @herecomesthewriterwitch @megaliciab @meyocoko @alkadri-layal @let-me-luve-you

[redhairedwolfwitch]

Double Screwed (So Screwed Part 2) - Erin Lindsay x Upton!Sister!Reader - Chicago PD

So Screwed

Summary: Erin has just found out the girl she kissed and stayed over the night cuddling with is Hailey Upton's sister. And now Hailey Upton is at the door, looking for you.

Request: Maybe for the part two of so screwed you could do a time jump where they started dating and somehow Hailey didnt catch them and one day Hailey want to introduce her sister to the team and Erin is there on a case and she is hurt and Hailey doesnt know why her sister is so worried about Erin?

Previously...

A quick comparative glance explained everything as you stirred in Erin’s arms, hearing a knock at the door.

“Y/n? Are you up yet?” a familiar voice enquired from the outside of your apartment. Hailey’s voice.

You were Hailey’s younger sister.

Hailey was at the door.

Erin was in your apartment, in your clothes.

She was screwed.

///

"Ah, shit!" You exclaimed, climbing out of Erin's arms to run to the door, gesturing for Erin to head to the bathroom as you followed after hiding carefully hiding Erin's things.

"Hailey, I'll meet you at the brunch place, okay? I'm kinda... busy, right now..." You grimaced slightly as Erin raised an eyebrow, realising what type of story you were coming up with to deter Hailey from entering your apartment.

"Oh... oh... seriously? I didn't need to know-"

"And I've been scarred for life after walking in on you and Jay, so take that as a courtesy. I'll meet you at the brunch place at 11, okay?" You retorted, hearing Hailey agree before she left, you let out a sigh and crouched down to hold your knees to your chest.

Erin approached you after a moment, crouching down next to you as you looked up at her.

"I'm so sorry, that was so... I'm sorry, I forgot Hailey wanted to go for brunch today since it's her day off." You explained, freezing as Erin wrapped her arm around you to pull you into a hug.

///

"Hey, sorry I'm late, the traffic's just- why are you giving me that look?" You raised an eyebrow, twirling the brunch place menu in your hands as you met Hailey's gaze, whilst Jay just chuckled to himself.

"What?" You frowned as Hailey rolled her eyes.

"We were wondering if you were bringing whoever you had over to brunch." Jay teased, whilst you scoffed.

"At least I gave you a warning. You two have scarred me for life on several occasions." You retorted, looking down at the menu to try hide how much your cheeks felt like they were burning.

/// 6 month time jump ///

You were curled up on your couch, checking your emails when your phone chimed.

Erin<3 - on my way with dinner

Y/n<3 - you're the best

You smiled as you heard a knock at the door, detaching from where you were one with the couch to go open the door.

"You're amazing." You leaned into quickly kiss Erin, letting her inside as she held the takeaway bag with one hand, the other going to hold your cheek as you kissed her.

"How was work?" You enquired as you got the bowls from the cupboard, pausing as Erin leaned into you to reach for the mugs.

"The Intelligence Unit your sister is in, that I was in once, they stumbled across something on our radar, so I have to work with them." Erin explained, putting the kettle on as you froze.

"Isn't that kinda a conflict of interest? I mean, Hailey doesn't know we're a thing, in fact, she hasn't properly introduced me to her team. I've only met Jay because he's her partner, in more ways than just professional." You replied, giving Erin a nervous look as you mentioned Jay.

You knew Jay and Erin were a thing, she'd told you after the two of you had been dating for 2 months. The two of you had been dating for 6 months now.

///

"Y/n? Are you home?"

Erin called out as she returned from her first day at work, working alongside Intelligence, specifically your sister, Hailey, and her partner, Erin's ex, Jay.

"In the shower!"

Erin smiled to herself for the first time since work, putting her shoes away and making a beeline to the bathroom.

///

You let out a sigh as the water ran over your body, facing the shower as you wiped your hands over your face.

Goosebumps trailed across your skin as hands gently wrapped around your waist, lips trailing up your shoulder as you hummed.

"Hello, my love." You cooed, turning around to meet Erin's eyes, your hands resting on her shoulders as the water cascaded over the two of you.

/// 5am next morning ///

The buzzing of your phone stirred you from your shared slumber with Erin, your bodies tangled together under the sheets as you reached over to grab it.

"Hailey wants to go for drinks at Molly's when this case you're all working on is over. Do you think we need to tell her we already know each other?" You bit your lip, leaning down to kiss Erin on the forehead as she smirked.

"We tell her we're already acquainted, well acquainted..." Erin cooed, running her fingers over your thigh as you let out a gasp.

"That's just asking for the shovel talk from my sister, and she probably won't look at me if you tell her how acquainted we are..." You replied, pouting as Erin's alarm began to go off, signalling she had to get ready for work.

Your eyes followed Erin's figure as she trailed over to the bathroom, pausing in the doorway to raise a tempting eyebrow at you, smirking as you bit your lip, throwing the covers off and hurrying after her.

///

You were sat proofreading a draft of a script you'd been working on when you got the call.

The call that had your stomach doing sommersaults as you answered, abandoning everything to hurry to Chicago Med.

///

"Y/n? What are you doing here? Are you okay?" Hailey scrambled to stand up, hurrying over to you as Jay followed, the pair checking you over for injuries. Neither of them saw you looking over their shoulders, trying to get a glance of Erin's condition.

"Is, is everyone okay?" You stumbled over your words, spotting Erin walking out of a treatment room, holding an icepack to her head.

Erin's eyes widened when she realised her emergency contact had been called when she'd gone for a head CT, to rule out a concussion.

The urge to run over to the love of your life overwhelmed you as you met Erin's eyes, seeing her panic before Voight walked over to talk to her.

"Y/n? Hey, are you okay? You look like you're going to be sick." Hailey's hand went to your forearm, her thumb rubbing circles into it as you met her gaze, taking a deep breath.

"I thought, I thought one of you got hurt..." You explained, running your free hand down your face.

"Adam got a few grazes and Erin just narrowly avoided a concussion... I don't think you've met Erin, actually, uh-"

"Hails, it's okay, I need to head back, I have a video meeting about a script..." You stated, watching Erin from the corner of your eye before Hailey hugged you and let you leave.

///

Hailey: case is done, how about we get that drink at Molly's?

Y/n: sure, are you heading there now?

Hailey: Jay and I can pick you up?

Y/n: I already have a ride, I'll see you there!

Hailey: since when?

read: 19:47

///

Hailey and Jay exchanged looks as you walked into Molly's, grinning at something Erin had said as she walked in with you.

"Erin was your sister's ride?" Jay frowned, observing how you and Erin were so wrapped up in each other's worlds that neither of you had realised Hailey and him were there.

"I think she's more than my sister's ride." Hailey pointed out, raising an eyebrow at Erin's hand on the small of your back.

It was only when you looked at Erin, spotting Hailey and Jay from the corner of your eye that panic ran through you.

You were both screwed. Double screwed in fact.

[thebookreader12345]

Major Discovery

Pairing: Halstead Sister! x (Jay Halstead x Hailey Upton)

Summary: Y/N's informed that Jay is in the hospital, and at Chicago Med, she sees that Hailey is just as anxious as she is to find out if Jay's okay, which leads to her finding out about Hailey's feelings for her brother

Requested: Yes, by @stephie123

Warnings: slight swearing, mentions of injuries/near death

Word Count: 1,784 Words

Note: takes place during Mercy, Season 7 Ep 10 of Chicago PD

"Nice save back there," Kelly acknowledged and pat my shoulder. "I didn't know there was someone left in the house."

"One of the perks of having a detective for a brother is that he taught me to observe everything," I tell my lieutenant. "So when I saw that family photo on the mantle, I knew there had to be one more kid in there somewhere. Please don't make it a big deal and tell the rest of the firehouse though. It was just an observation. Nothing huge."

Kelly held his hands up in surrender. "All right. I won't say a word." Just then, my phone started ringing from where I had just placed it on the Squad 3 table, and Jay's name lit up the screen.

"Speaking of the devil," I joke and accept the call, holding the device up to my ear. "Hey, Jay. What's up?" But the voice that responded wasn't Jay. I listened intently as a woman talked to me from the other side of the line, her voice ever so calm while I was freaking out. "Okay. Um, is Will already there?"

"Yes," the woman replied.

"All right. I'll be there shortly. Thank you," I say and hang up. As I lowered the phone from my ear, my hand began to shake, and tears welled up in my eyes.

"Y/N? What's wrong?" Kelly asked.

"That was the hospital," I mumble. "Jay was just shot. H-he's in surgery. I have to go."

Kelly nodded. "Of course. I'll talk to Boden. Go."

The whole drive to the hospital, I couldn't help but think of the worst possible outcomes of the situation. More tears brimmed my eyes, a few even slipping down my cheeks, which I hastily brushed away. In the parking lot, my car lurched to a stop in the nearest open spot, and as soon as I exited the vehicle, I was running towards the ED. Inside, I spotted the rest of the Intelligence Unit, all with somber looks on their faces. Among them was Hailey, Jay's partner, who I had grown close with the past few weeks. Between chatting about anything and everything at Molly's to talking discreetly about Jay behind his back whenever one of us had to go the others' place of work for something, we had developed a good friendship. And then I spotted my older brother Will, his red hair making him stand out easily in the crowd.

"Will," I call out and dodge a few cops to get to him. "Is Jay okay? Please tell me he's gonna be all right."

"I-I can't," Will confessed. "Because I don't know. Dr. Marcel has him up in surgery. He said the bullet grazed an artery, and he's lost a lot of blood."

"This cannot be happening," I whisper as my breaths started coming out unevenly. I wasn't that much of a stranger to panic attacks. I had a few of them in my teenage years growing up, plus a couple here and there as an adult. And right now, I was not looking forward to having one in front of all of these people. Thankfully, Will was there to help me through it.

"Hey," Will murmured and pulled me towards him, wrapping his arms around me to hold me close. "This is Jay we're talking about. He's a fighter. He's gonna get through this. And when he wakes up, the both of us are gonna be there for him, okay?"

"Okay," I sniffle. "But only after we give him hell."

Will laughed. "Deal. I've gotta get back to work now. I'm hoping it'll help me keep my mind off of this for at least another hour. You're more than welcome to stay in the doctors' lounge if you want to be alone."

"Thanks, but I think I'd rather stay here," I admit and glance back towards the packed waiting room, my eyes landing on the blonde detective sitting off to the side by herself. "I should talk to Hailey and see how she's holding up. But I'll see you in a bit."

"All right. See you later," Will confirmed and walked back in the direction of the ED. As soon as he left, I made my way over to Hailey and took the seat next to her, pulling my knees up to my chest so that my heals rested on my chair as well.

"Hey," I greet her. "You doing okay?"

"I should be asking you that," Hailey countered. "Jay's your brother."

"He's also your partner," I retort. "And to me, that means you're basically family. How are you holding up?"

Hailey sighed and rubbed a hand over her face, leaning back against her seat. "I saw him before he got shot. He was right next to me. I was gonna get him to safety, but he said he wanted to go help Angela, so I let him. I should've insisted that he come outside with me. If I did, he wouldn't be in this position."

"Hailey, this is not your fault," I console her. "Even if you insisted you get him back with the rest of the team, chances are he wouldn't have listened. That's just how Jay is. He cares too much for others, even when he shouldn't. So don't blame yourself for something you couldn't have stopped."

"Thanks, Y/N," Hailey mumbled and turned to face me. "Now it's my turn to ask. How are you doing?"

"Well, I'm not feeling the greatest right now," I answer. "This isn't the first time Jay's been in the hospital, and I know it won't be the last, but I just want it to get a little easier, you know? The other two times he was shot, it wasn't anything serious. But now...I knew with him being a cop he'd face danger on the job, but I never imagined that there'd be a time when I'd lose him."

"You're only worried because you love him," Hailey told me.

"So, what? You love him too?" I question playfully.

"Sure, just not in the same way you do. As a friend," Hailey clarified.

"Uh-huh," I hum quietly to where she couldn't hear me. "I uh, I'm gonna get a coffee. You want one?"

"Coffee sounds great," Hailey responded.

............................................

"Crockett, hey," I breathe out and join the doctor by the entrance to the ED. Hailey was a few feet behind me, also ready to hear the news about Jay. Unfortunately, the rest of Intelligence had a case, so they had to leave, but I was sure Hailey would deliver the news. "How's Jay?"

"I managed to stop the bleeding, so he's out of surgery and in recovery," Crockett informed me. "He's also awake and alert, but for the time being, only family members are permitted to see him."

"Go," Hailey urged. "I can wait."

"Okay," I say. "I'll come get you in a little bit. And then you can lecture Jay about never getting shot again."

Hailey cracked a small smile. "That I can do." So Crockett led me up to Jay's room, and when I got there, I saw that Will was already inside.

"Man, I thought someone finally managed to kill him," I joke to Will.

Will chuckled. "I know. Such a shame that he's alive."

"I hate both of you," Jay grumbled.

"No you don't," Will disagreed and turned to me. "I've got patients down in the ED that I've gotta get back to, so would you stay with him?"

"Boden gave me the rest of the shift off, so I will not leave his side," I announce. With that, Will left the room, leaving me all alone with Jay. I took the seat next to Jay's bed, and my eyes glanced at the sling my brother's arm was in, which didn't go unnoticed by Jay.

"What?" Jay quizzed.

"Nothing," I mutter and tear my eyes away from his bandaged shoulder.

"Y/N," Jay coaxed.

"You could've died, Jay. We just lost dad last year, and to lose you too..." I trailed off, unsure of what to say. But Jay understood, and with his uninjured arm, he reached out and took ahold of my hand.

"Listen to me," Jay requested. "You and Will are never gonna lose me. Never. Cause I'll always fight to stay alive for the both of you."

"And Hailey," I add in quietly.

"What was that?" Jay asked.

"Nothing," I lie and stand up. "I'm starving. Hailey's still down in the waiting room, so I'm gonna see if I can convince Crockett to let her up to see you while I'm eating. I don't trust you in hospitals by yourself. One way or another, you'll find some way to leave."

"Hospitals are terrifying," Jay defended. "I don't know how Will works in one. And Hailey's still here?"

"Of course she's still here. She's your partner, Jay. And she cares about you a lot. Now, I really do need to get something to eat, so I'll see you in a bit. Don't die while I'm gone," I call out playfully as I exited his room.

About half an hour later, I finished up my lunch in the cafeteria and went to go sit back with Jay, and when I got to my brother's room, I saw him and Hailey talking. The way Hailey was looking at him now, and the way she was talking about him earlier...I was pretty sure she had feelings for him. When Hailey noticed my presence, she drifted away from Jay.

"I uh, I've got to get back to the district," Hailey declared. "I'll talk to you later, Jay." Hailey then walked past me, but I knew I couldn't let her go. Not yet.

"Hailey wait!" I shout and follow after him. Hailey stopped in her tracks a hundred or so yards beyond Jay's room, and I was able to catch up with her. "You love Jay, don't you?"

"W-what?" Hailey stammered.

"I saw the way you looked at him. It's the exact same way my dad used to look at my mom," I explain. "I like you a lot, Hailey. And you'd be really good for Jay unlike Erin, who left him unexpectedly when he was going to propose. Just don't hurt him, please. I don't know how much more pain he can take. Physically and emotionally."

"I won't. I promise," Hailey pledged. As Hailey took off to get to work, I went to rejoin Jay in his hospital room.

"What was that about?" Jay implored.

I waved him off. "Nothing you need to worry about. So, dear brother, what are the two of us gonna do for the next day or two to keep busy in here?"

______________________

Tag List:

@prettypyschoinpink @securityfriendly-jay @scarletsoldierrr @lorenakaspersen @virtualreader @carnationworld @caitsymichelle13 @ncostin2001 @dreamingmanip @campingmonkey @winterberryfox @nevertoofarfromivar @anotherfan07 @giagma @mrspeacem1nusone @i-like-sparkly-things

[wandawxdow]

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[deanstead]

Hi, can I request 31. “I need you to run.” with Jay Halstead x sister!reader? Luv ur fics!

Pairing: Jay Halstead x HalsteadSister!Reader

#31: I need you to run

A/N: Surprise! This is probably not the fic you expected HAHA

This was requested more than once!

You stared down at your notes, which were now literally drowning in coffee.

You looked up at Jay who gave you a sheepish look.

“Y/N, I’m sorry, I was just trying to…”

You took a deep breath. You’d told Jay a billion times not to bring you coffee when you were studying. You’d told him you’d ask if you needed coffee and you’d definitely told him to use a freaking tumbler.

Now, thanks to your overly helpful brother, your notes were ruined. The notes you’d spent hours on.

“I need you to run.” You said, very slowly.

Jay looked back at you in semi-confusion.

“Before I fucking kill you.” You snarled.

[redhairedwolfwitch]

So Screwed - Erin Lindsay x Fem!Reader - Chicago PD

Summary: Erin returns to Chicago too late. Jay has moved on and is in a happy relationship with Hailey. Now, Erin is left to her own devices in a city she used to know.

Erin didn't expect to end up being transferred to the new Chicago branch of the FBI.

But heading back to Chicago gave her the opportunity to see the people she left behind, over five years ago. Turns out a lot can change in five years, including people.

Intelligence weren't at the district when she stopped by. An individual from patrol was on the desk, explaining how Platt had said it was beer o'clock and that Intelligence were at Molly's.

The hustle and bustle of the crowd at Molly's gave Erin the perfect cover as she glanced around for any of her former co-workers.

Kim and Adam were talking quietly about something, but Kim had a child's toy in her hand as Kevin was just chuckling and talking to a woman she'd never met. Voight wasn't at Molly's, but then again, he never really went to Molly's.

Jay was a different story though. He was nowhere to be seen until Erin spotted Hailey. Hailey was chatting to Will as Jay approached, beers in hand.

Despite the pang of her heart, a soft but sad smile crept its way across Erin's face as she watched Jay kiss Hailey.

Turning on her heel, she headed out of Molly's, not wanting to ruin the moment as the ex who just turned up from out of town after leaving years ago.

That was what she was, but her former co-workers didn't need to know that. Maybe if she had actually kept in contact and maintained/developed friendships with them, things would be different.

///

Taking a cab, Erin ended up at a different venue entirely.

The venue was different to Molly's. It wasn't a bar for firefighters, police and medical staff. This one had a completely different theme.

"First time here?" Your voice over the music snapped Erin out of her staring contest with the neon sign.

"How could you tell?" She rasped, noticing how your eyes were e/c, despite the tinted heart-shaped glasses you had on.

"You froze at the 'girls, girls, girls' sign. Either you didn't know this was a gay bar, you're a baby gay or you just needed somewhere else to be besides where you were before." You explained, leading Erin towards an area where the two of you could properly hear each other.

It was a balcony that looked over the dancefloor, leaving you to chuckle as Erin's eyes went wide.

"I take it that it's all three? Don't worry about it, this is a safe space. I'm going to get a drink, do you want anything?" You enquired, leaving Erin to pause, her mouth dry as she glanced around for a drinks menu or something.

"I'll have whatever you're having."

You nodded, giving her a soft smile before heading towards where you knew your friend was working the bar.

///

Erin glanced around as she watched you disappear.

This place was nice, regardless of the cheesy sunglasses that a few people were wearing.

"Hey, here's your drink." Your voice caught her attention as you presented the drink to her.

"Thanks." She smiled, watching you sip your drink before you paused.

"Oh, yeah. Your cheesy sunglasses." You grinned, leaving Erin to quirk a brow as you passed her a pair of heart-shaped glasses with purple-tinted lenses.

"What is with the sunglasses, by the way?"

"Uh, it's like a pass to get in, you have the sunglasses, you get bonus stuff... the bonuses are more useful during the day though. This place is a safe space, day and night. Makes a cute cafe/library thing too. I'm Y/n by the way." You explained, leaving Erin to nod at you.

"Erin."

"Erin is a pretty name." You smiled, sipping your drink before diverting your attention to the floor below.

"Thanks, I think," Erin replied, sipping her drink and admiring the taste, "you're not so bad yourself."

"Cheers, I think." You laughed, leaving Erin to chuckle in response.

"Sorry, I'm really not good at flirting." You admitted, swallowing nervously as Erin laughed.

"Oh, so you're flirting with me."

"It's not my fault you're pretty and I want to know you, even if you don't want to be more than friends." You retorted, fiddling with your sunglasses as Erin tilted her head to the side.

"That was actually kind of adorable." Erin confessed, chuckling as your jaw dropped in shock.

The two of you were sat talking and drinking your drinks until you realised what time it was.

"Did you book a hotel room to stay in whilst you're in Chicago or is all your stuff still in New York?" You enquired, noticing how Erin was giving you a look.

"I... I'll sleep on my couch if you don't have a hotel room booked." You explained, leaving Erin to chew her lip.

"Honestly, I had a hotel room booked but I don't remember the name. It was one of those places that don't have a generic name-"

"Yeah, you're not going to find where you're staying if we have to search google maps for it. Just crash at mine."

"How do I know you're not a murderer?"

"Well, besides the fact you could kick my ass in five seconds. I'm a writer-filmmaker-actor who also works as a lifeguard and used to work as this cafe, not a murderer." You retorted, leaving Erin to chuckle.

"True, I could kick your ass in five seconds."

///

"So... this is my place." You gestured around as you unlocked the door, leading Erin inside. The two of you were tipsy, but not enough that anything would happen.

Your place was open plan, with the kitchen table being behind the couch that Erin had noticed you slipping towards as she spottted your bedroom.

"Ah, no, your back will be killer if you sleep on that. We can share the bed?" Erin tilted her head to the side as she gently took your wrist into her hand.

"Fine, but be warned, I tend to sleep-cuddle." You retorted, rolling your eyes as Erin smirked.

Her smirk was washed off her face as you threw an oversized t-shirt and pair of shorts to her whilst you beelined to the bathroom.

The room wasn't very bright, as fairylights and two small bedside table lights. This meant that the photo frames weren't easily seen as Erin slipped into the clothes you had provided her with.

///

Erin let out a breath as she exited your bathroom, feet treading across the mat you had on the floor near your bed as you lay in bed, reading a book.

"Sorry if this is weird... if you want, we can treat it like a sleepover and just play twenty questions until we fall asleep?" You suggested as the lights were turned off and Erin was laying in bed next to you.

"Sure... you start, I guess." Erin replied, leaving you to shuffle onto your side.

"You've never played twenty questions before, have you? Or did you not have sleepovers as a teen so this is technically your first one?"

"Am I that easy to read?" Erin responded, debating whether hitting you with a pillow would stop your telepathy.

"I think we had similar childhoods... anyway, favourite movie?"

You were cut off as Erin rolled over, pressing her lips to yours for a moment before she rolled over, facing away from you. Her face burned as you giggled.

"That's not a movie!"

///

The sun peeking through the blinds had the two of you stirring from your shared slumber.

Erin's head turned to the side as she tried to stretch, finding the weight of your head on her shoulder preventing her from fully moving her arm.

However, something on the bedside table caught her eye.

Three framed photos were chilling with a pile of books.

One photo included a young you, with your sister and brothers.

A second photo included your pet that you had after graduating college.

It was the third photo that had Erin's stomach churning.

You and Hailey Upton.

You were Hailey's younger sister.

A quick comparative glance explained everything as you stirred in Erin's arms, hearing a knock at the door.

"Y/n? Are you up yet?" a familiar voice enquired from the outside of your apartment. Hailey's voice.

Hailey was at the door.

Erin was in your apartment, in your clothes.

She was screwed.

[deanstead]

Reinforcements

Pairing: Will Halstead x HalsteadSister!Reader x Jay Halstead

Requested: yes, by anon

Summary: Y/N gets jumped on the way to meet her brothers. After her brothers arrive to help and take her home, she shuts them out and Jay has to call in reinforcements.

Characters: Jay Halstead, Will Halstead, Hailey Upton

Word Count: 1,604

Warnings: attempted sexual assault, language

A/N: This is primarily a Halstead!Sister fic, so I left things between Upstead kind of vague cos er I don’t really write for them lol. But I thought this was a good idea for a oneshot so I ended up writing it anyway. This is also the last of the old requests!

HALSTEAD!SISTER MASTERLIST

You glanced at your watch. You were already late so Jay was going to nag and you really couldn’t handle that today. What you really needed was a drink. Which was why you were glad that at least you’d agreed to meet your brothers at Molly’s.

As you spotted the lights of Molly’s, right on cue, your screen lit up with Jay’s name flashing across it. You rolled your eyes just as you answered the call.

“Yeah, I’m like five minutes away. Maybe three if you hang up. Can you just…”

You didn’t manage to finish your sentence as you felt someone grab you from behind. You gave a yelp of surprise as you your phone clattered down against the concrete pavement. You weren’t sure if it had been picked up by your brother on the other end of the line but you could vaguely hear Jay calling your name through the speaker. Whoever had grabbed you didn’t seem to care, Jay’s voice fading as the strong hands pulled you deeper into the adjacent alley.

Whoever this was was strong. Even as you fought with all your might, you felt yourself getting dragged deeper and deeper away from the street. You could smell stale alcohol even though he had a hand clamped over your mouth and nose, his other arm looped around your front.

As he pushed you against the wall of the alley, you saw him for the first time, feeling panic mixed with fear pulsate through your body. His eyes looked glazed over, except for the dangerous look in his eyes as they swept across you.

“Just my type.” He drawled.

Fuck.

You tried calculating your chances of escape if you hit back now but it was difficult even threading together a singular coherent thought as your brain felt just as paralyzed as your limbs. You could hear Jay’s voice from a distant memory, walking you through what you should do when you found yourself in such a situation, as your attacker trailed one hand down your side, the other hand clamped around your throat threateningly.

Now, Y/N. Move, fight, do something.

Your body wasn’t exactly cooperative, but you had to do something, especially now as you felt one of this thumbs hook against the garter of the trousers you’d put on this morning.

No fucking way.

The desperation had overtaken the fear and allowed your limbs to move again. You tried to pull your knee upwards, the way Jay had taught you but he seemed to anticipate your moves, leaning his weight against you now so you could barely twitch your legs. He let out a chuckle that sent a shiver down your spine.

But that wasn’t all Jay had taught you.

You pushed your palm hard into his face, pulling back your other arm and hammering against his wrist that was around your neck. Surprised by the sudden motion, his hand slid off you as he stumbled backwards and you took off.

“You bitch!”

You could feel the tears prickling in your eyes but you couldn’t do this now. Not until you were safe.

“Jay! Will!” You screamed, only hoping they’d already come out to find you, pumping your legs harder as you felt him gain on you.

You tried to step off to the side to avoid him but you were a second too late as he dragged you down onto the concrete ground. You felt the wind knocked out of you for a second before the panic overtook again as he pinned you down onto the ground.

If your brothers didn’t arrive soon, you were screwed.

But your brothers had never disappointed you even once in your entire life.

“Y/N!” Will’s voice, followed closely by Jay’s furious roar.

You felt the pressure lift off you as Jay pulled the guy off you violently, and you heard the obvious sounds of Jay throwing punches.

Your breath felt like it was stuck in your throat as you heard extra voices join the scene but you couldn’t process anything right now. Even Will’s voice sounded like it was coming from far away.

“Y/N. Y/N!” You blinked, realizing your oldest brother was right here, he was here.

“Will…” Your voice shook with the effort it took.

Will nodded back at you, his hands holding your shoulders gently. “Breathe. Breathe.”

You frowned until you realized that you weren’t breathing. It was like your body forgot how to do it automatically and you inhaled now, consciously.

Will exhaled with relief. “You’re okay, alright. I got you.”

The tears now streaked across your cheeks as your body shook and Will pulled you into him protectively, a hand resting gently on your head like he had when you’d had nightmares a long time ago when you could still jump into his bed.

You turned your face into Will, just as you felt someone else touch your shoulder. You almost jumped out of your skin, curling further into Will’s embrace before you heard his voice.

“It’s me.”

You turned your face upwards now. “Jay?”

Jay’s green eyes were still laced with rage, mixed in with worry, and his knuckles were bruised. “Let’s get you out of here, alright?”

You nodded, as Will helped you up and your knees almost buckled before you realized they were shaking.

Jay reached out for your hand and squeezed. “You’re alright.”

“He…”

“Adam is hauling his ass where it belongs.” Jay just answered through clenched teeth.

“Y/N, will you come out, please?” Will pleaded for like the tenth time since you’d gotten home and shut your brothers out, both literally and figuratively.

You’d always loved having two brothers you were close to. The only time you hadn’t was when you needed a girl to talk to. How were you supposed to explain the fear you’d felt in that moment when you knew what he wanted, the disgust you felt as he held onto the garter of your trousers knowing that in a second….

You closed your eyes, trying to wipe the image, the feelings, everything out. You knew you needed to get it out, but you didn’t know how to tell your brothers.

Besides, you were pretty sure if you did tell them, Jay would be out of the house in a second to literally kill someone. And you couldn't let him do that, not to himself.

“Y/N? It’s me, Hailey. Can I come in?”

Your head jerked up in surprise to hear her voice but you managed to find your voice. “Yeah.”

The door cracked open and Hailey moved in towards you, Jay following on her tail.

You gave him a look and Hailey glanced over her shoulder. “Out.”

“I asked you to come and help, I didn’t…”

“So let me help, Jay. Out. No guys in here.” Hailey said, before she threw both the Halstead boys out, shutting the door in her partner’s face.

“Hey.” Hailey called, before she perched herself next to you, still keeping a small distance between the both of you.

You didn’t answer and Hailey didn’t push, just sitting next to you in silence, waiting for you to be ready.

“Jay called you?” You asked quietly after a beat of silence.

Hailey nodded. “Yeah, he was worried.”

“He’s always worried.” You shot back, which made Hailey smile.

You let the silence fall again before you started talking, telling her practically everything that had happened and Hailey reached over for your hand now, squeezing it, not even letting go as you finished recounting the night’s events.

“I just… I shouldn’t have been late. I should have left earlier, I…”

Hailey shook her head. “Y/N, stop right there. You didn’t do anything wrong, alright?”

“And Jay taught me a bunch of stuff in case I got stuck in a situation like this but I just… I just froze. If I had fought harder… I shouldn’t even have let him drag me into the alley in the first place, I should have….”

“Y/N. Look at me.” Hailey said, her voice firm.

You glanced up at her.

“You did nothing wrong. Sometimes when we’re hit with a trauma, when fear takes over…” Hailey paused, clearing her throat before continuing. “Sometimes our bodies just react. It’s instinct. And it’s not your fault.”

You swiped off the tear that traveled down your cheek. “Is Jay disappointed?”

Hailey frowned. “What?”

“He taught me everything. How to get away, what to do and I just…”

Hailey squeezed your hand again. “Right now, Jay is just glad you’re not hurt alright? And from what I heard you fought pretty damn hard. I’m sure Jay’s proud.”

You glanced up and Hailey smiled. “You think you up to seeing them now?”

You nodded, so Hailey reached over to give you a hug, before going to open the door.

“You okay?” Jay asked, the moment he barged in.

You nodded, but then shrugged. “Kind of, but not really. I…”

“You don’t have to tell us anything, you don’t have to say anything. But we’re here.” Jay said, reaching over to envelope you into a hug.

You could even tell the gentle hand that was patting your back was Will’s, even as you closed your eyes against Jay and you nodded.

“Thank you.” You whispered, feeling the safety of being with your brothers overtake the fear that had still been lingering just a moment ago.

Jay glanced back at Hailey, with you still pressed into his side, making you once again feel like that little girl that used to sit on her older brother's shoulders. “Thanks, Hailey.”

Hailey just nodded and smiled as she leaned against the wall, watching the three of you. "Anytime, partner."

You smiled back at Hailey and she gave you a smile. "Anytime." She repeated at you.

THANK YOU FOR READING!! PLEASE TELL ME WHAT YOU THOUGHT OF THIS!!

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[specialagentsoftie]

I saw you said upstead requests were ok so maybe imagine upstead talking about kids but there's a reader character in it somehow, maybe poly upstead? you can choose how to add it in ❤️

I usually write x reader fics and this one was different for me, so I didn't go straight to poly Upstead (maybe in the future)! I just did Halstead!Sister reader x Upstead for this one since idk what the hell I'm doing.

I did make it a longer fic though because it kinda got out of hand. Hope that's ok!

You can find it here.