#willhalsteadxreader

*Not my gif*

Pairing: Will Halstead x Reader

Requested: Yes

Prompt: Dirty texts lead to a horny Halstead

Warnings: Smut (18+), swearing, sexting

A/N: Will’s texts are bolded, yours are italicized

It had been too long, way too long since you’ve had the time to be with your boyfriend. You flew home for your mother’s birthday and ended up staying a couple more days than you had originally planned. On top of that your flight had gotten delayed twice thanks to a storm rolling through so instead of getting to spend a few hours with Will before his shift you had gotten home an hour after he already left, and man were you going through some withdrawal. Walking in your shared apartment you dropped your luggage in the living room exhaustion hitting a little. You decided to take a nap knowing full well your boyfriend wouldn’t be home for at least a minimum of 12 hours and would likely be even longer than that. Falling into your bed Will’s minty scent took over instantly relaxing you. Pulling out your phone you pulled his name up typing a quick message informing him you were home safety before drifting off.

Waking up you huffed at the clock not appreciating the time that still stood between you and Will. Dragging yourself out of your bed and into the shower you let the water cascade over your body. A smirk formed on your face as the idea popped in your head. Stepping out from under the water you dried your hands before leaning to grab your phone off the shelf. Pulling Will’s messages back up you began to type,

“The things I would give to be pushed against this shower wall right now is outrageous.” Accompanied by a very tasteful picture.

Setting your phone back down you finished showering wrapping your towel around your body heading towards your bedroom. While getting dressed you heard your phone ping from the bathroom. Smiling you headed to grab it opening Will’s text,

“Holy hell baby. I’m feeling tortured enough. How am I supposed to focus after that? I may have to sneak off to the bathroom here for a second.”

“Don’t you dare. I want it saved all for me. I don’t know how you were focusing before that all I can think about is you.” You replied.

“I miss my girl so much. I can’t wait to get home to you. I have a whole list of things I need to do to you.” Will answered.

“Is that so? Feel free to paint me a picture.” You teased.

“How would that be fair? You’re home all alone able to do whatever you want.” He retorted.

“Alright then..let me paint a picture for you?”

“Baby I’m working and I’m already on the brink of insanity..” Will pleaded. You gave in feeling a little bad imagining him suffering at work between patients. However, an hour later the guilt had faded as you pulled up the texts again to continue the teasing.

“I thought about it and I realized I wouldn’t be a good girlfriend if I didn’t give you a heads up to what’s gonna happen tonight.” A few minutes had passed before you had gotten a reply,

“Well...I wouldn’t want you to think you’re a bad girlfriend or anything.” He answered making you laugh.

“Oh man baby I cannot wait to jump on you. I miss your smell, your lips, your taste, your touch so much. Can’t wait to have my lips on yours, on your chest, on your abs, and most importantly wrapped around your cock. I want your dick shoved down my throat, so rough I won’t be able talk tomorrow.” You started.

“You have absolutely no idea how bad I want that. You’re such a pro at sucking this dick.”

“Practice makes perfect and I think I may be a little out of practice so I better get to work. Can’t wait to tease you a little. Feeling you up outside of your jeans, love feeling your dick go hard in my hand. Use my teeth to pull your zipper down just so you can feel my breath. Want you begging for my mouth baby. Twitching in my hand before it even gets there. Not sure whether I should swallow or not though. Love the taste of you filling up my throat, but also love watching you cum all over your stomach and licking it all up after kinda the best of both worlds..what do you think?”

“Fuck babe...I’m so hard how am I supposed to hide this?”

“Maybe you shouldn’t..let everyone know how bad you need me...especially Natalie…” You couldn’t help but tease him a little knowing you’d probably get at least a small laugh out of him.

“Don’t want her. Only you and that perfect pussy of yours. Can’t wait to get home and eat you up because believe me I’m starving.”

“I’m more than ready. Can’t wait to have that handsome face of yours shoved in my pussy making me feel so fucking good.”

“Hell babygirl. I don’t know how I’m going to make it through this shift. I’m going to absolutely wreck you when I get home.” He replied after a while.

“Is that a promise?” You teased.

“You better fucking believe it.” He texted.

You had finally decided to leave your boyfriend to work turning Netflix on. Drowning the hours away until you finally heard the door of your apartment click. Turning your head to see your boyfriend walking in, dropping his bag at the door, pushing it closed before turning to face you. A smile immediately surfaced on your face, heart thumping faster. It had only been 2 weeks but you swear you had almost forgotten what he looked like. Realizing long distance couples should get all the props in the world. Jumping up off the couch you launched yourself into his arms wrapping yourself around his body. You felt him laugh, wrapping his arms around you to pull your tighter against his body.

“Hi baby.” He whispered into your ear kissing your cheek softly.

“I missed you sooo much.” You whined nuzzling your face into his neck relaxing at his scent too easily.

“You’re telling me.” He smiled pulling your face up to meet his lips, humming at the feeling. Your hand instinctively wrapped around his neck pulling him down enough to your height to deepen the kiss. Biting your bottom lip, his hands moved down to your thighs, getting the hint you jumped letting him support you as you wrapped your legs around his waist. Moving his lips down your jaw to your neck he pressed you up against the nearest wall nipping at your collarbone in the process.

“Not wasting any time are we?” You teased starting to unbutton the front of his shirt.

“I may actually explode if I wait any longer. Which is all your fault. Thinking you’re so clever making me suffer at work all day. I had to hide my hard on for hours.” He admitted tugging at the hem of your shirt, before you discarded it on the floor leaving you left in only your panties. “As gorgeous as ever.” He smirked lips moving to your breasts making you moan softly at the contact as he circulated between your nipples. Taking it in and enjoying it for a second before reaching between the two of you working on his belt and jeans, struggling at first in the position but not too long after getting them pushed down along with his underwear. He adjusted his grip on you stepping out of them and kicking them to the side before moving his hand down to your core, gently rubbing on the outside of your panties. Whimpering you tried to push your hips stronger against his fingers making him chuckle. “And I’m the impatient one.” He joked leaning in to capture your lips with his, moving your panties to the side to properly rub at your clit before slowly inserting a finger into you. Moaning into his mouth he took this advantage to sneak his tongue in quickly taking dominance of the kiss. Curling his finger up to hit your sweet spot before inserting another, working you open again. Looking down between you, you see his dick upright, tip swollen red with precum already dripping out.

“I haven’t even touched you yet, what is this?” You smirked collecting the precum on the tip of your finger before putting it in your mouth to lick it off, chucking at Will’s whimper as he watched. Pulling his hand away from you, you gave his shaft a few tugs before moving your panties to the side again rubbing his tip up and down your slit a few times to collect the wetness before slowly starting to push him into you. Will’s eyes closed at your movement, breath trying to steady as you let him take over. Regaining control his nails digged into your thighs watching your face as he slowly pushed into you letting you adjust every couple seconds. Bottoming out his face moved to the crook of your neck before starting to set a steady pace as your hands rested at his shoulders trying to keep yourself up. Feeling the pleasure start to course through your body your head fell back against the wall, moaning out loudly without shame. “Man did I miss you and your dick.” You whined.

“I missed this pussy baby. Always so fucking good.” Will grunted into your ear tugging at your earlobe making you bite your lip sighing heavily, but quickly yelling out whenever he hit your g spot after adjusting slightly.

“Mmm, right there babe.” You informed nails digging into his shoulders. Your muscles were starting to burn so you could only imagine how Will was feeling but you were into much pleasure to care as his thrusts started to speed up, small grunts and moans filling your ear. Feeling your pleasure building you reached down between the two of you starting to rub your clit in time with his thrusts taking you to a whole other level. As you felt the knot in your stomach grow stronger and stronger you pulled Will in closer to your body raking your nails from your free hand down his chest leaving marks, crying out with every thrust.

“Come on baby, let go for me.” Will huffed out between ragged breaths. Seconds later you gave in screaming out Will's name, trying to grasp for him as your limbs shook, white covering your vision, going almost completely limp in Will’s hold. Coming back to reality just in time to hear Will screaming your name accompanied by a few curse words, muffled into your shoulder, his cum filling you completely. Will took a few deep breaths trying to regain control before slowly pulling out and gently sitting you back down on your feet where you grasped onto his biceps still wobbly on your feet. Chuckling he swiftly picked you back up bridal style before walking over and dropping you on the couch where you pulled him down with you. “In hindsight probably would’ve been less physically exhausting to just do it here but hey desperate times call for desperate measures.” He joked kissing your cheek and making you giggle.

“Can always be put to use in round 2.” You shrugged smiling up at him.

*Not my gif*

Pairing: Jay Halstead x Reader

Requested: Yes

Prompt: Sequel to Part 1 // Part 3 here

Warnings: Swearing, cheating

A/N: Jay’s texts in bold, yours italicized

You were woken up the next morning by soft kisses being pressed along your neck and shoulders. Whining a little you turned to face the man that lay behind you.

“Goodmorning gorgeous.” He smiled pushing the hair out of your face. Huffing you shoved your face into his bare chest causing him to chuckle, “still not a morning person I see.” He joked wrapping his arms tighter around your body. Gladly letting you sink back into his warmth.

“You’re hard.” You mumbled against his chest feeling the boner pressing against your leg.

“Do you blame it?” He smirked moving his hands up and down your body laughing when you nodded your head against his chest not moving. “I know. I know. No morning sex unless I’m willing to do all the work.” He kissed your head before flipping you underneath him, “Lucky for you I’m feeling quite energized this morning.” He smiled nuzzling your neck to kiss it. Humming you opened your legs wider to let him slip between them letting Jay take complete control of you. Just getting to the good part when your phone dinged a few minutes later. Huffing loudly in protest you reached over to pick it up squinting to see a message from Will. The guilt overtaking you as you then recalled the events from yesterday. “Who is it?” Jay asked, pulling your hips back towards him.

“Will.” You mumbled moving to open it.

“What’s he want?” Jay sighed running his fingers over your thigh, and instantly you were wide awake pushing him off of you and jumping out of bed.

“He’s on his way over, he just got off.” You hurried looking around for your clothes before remembering half of them still lay in a trail to your bedroom, in plain sight. Grabbing Jay’s jeans you threw them over to him as you wrapped a robe around yourself. Running out of your room to start the clean up tossing Jay articles of his clothing as he followed behind you, “Fuck!” You exclaimed reaching your kitchen where pieces of glass were shattered along with dried wine that had splashed on your floor and cabinets.

“I’ll sweep if you mop.” Jay bargained, nodding your head you quickly dumped out the little bit of beer Jay still had left when he sat his beer down the night before tossing it in the trash as he followed you over to your cleaning closet that was directly located behind your front door, jumping a thousand feet when there was a knock. Opening the closet you got out the broom and mop before you shoved Jay in just as the front door opened.

“Hey.” You said calmly, trying to slow your breathing from the panic.

“Hey.” He smiled stepping in and kissing you on the forehead, “sorry I didn’t give you more of a heads up I just figured since neither of us work tonight we could spend the day together. Talk some. But I definitely need a shower and nap first.” He laughed turning to walk into your kitchen to presumably get a drink when he stopped looking back at you, “what happened?” He gestured to the mess on the floor. Making you swallow hard,

“I was drinking last night and I never finished it. I must’ve knocked it over in the middle of the night when I came to get a drink.” You cover easily as he nodded,

“Here I’ll help-“ He started reaching for the broom but you cut him off,

“No. I got it, go ahead and get in the shower I’ll be in bed waiting for you after I get this cleaned up.” You forced a smile starting to feel a little light headed at the anxiety coursing through you. Will stopped to give you a light kiss before heading to the bathroom where you watched him intently only hurrying back over to the closet once you heard the water start, “okay you have 2 minutes get out, get out.” You started to push Jay towards the door.

“Okay, okay. But when are we going to talk about this?” He asked, stopping in front of the door, making you groan your eyes flickering between him and the door of the bathroom.

“I don’t know. Not now though I can tell you that!” You whispered as he pulled his phone out handing it to you,

“I’ll text you.” He informed you as you got the hint putting your new number in and handing it back.

“Okay seriously you got to go.” You reached around him to open the door quietly. He walked out into the hallway before turning back towards you. “Jay I’m not kidd-“ you started again before he quickly pulled you into his lips for a short but deep kiss.

“I’m sorry I wasn’t leaving without that.” He explained, making you shake your head but smile at the same time, “I love you.” He whispered looking into your eyes.

“I love you too.” You sighed reaching up to give him another quick kiss before successfully pushing him out this time, quietly closing the door after him. Earning a breath of relief your head fell back against it, “I’m the worst person alive.” You groaned to yourself before moving to clean up the mess that was made in your lust filled state.

Climbing into your bed you quickly did a double check that everything was as it was supposed to be switching the pillows in fear of Jay’s smell still permeating off them. Before relaxing or at least pretending to and waiting for Will to come in.

“I was hoping you would come join me.” Will playfully frowned walking into your room hair still wet.

“I was cleaning.” You laughed nervously.

“I know but a guy can fantasize.” He smirked, climbing into bed next to you and pulling you closer before leaning over you and capturing your lips. Rigidly you kissed him back begging your mind to relax when he pulled away looking down at you concern on his face, “Are you okay?” He asked. Swallowing hard you nodded,

“Yeah. I’m sorry I just didn’t sleep well last night I guess.” You answered making him sigh,

“Look [Y/N] I’m sorry I didn’t-“ He started before you cut him off,

“You’ve been awake for over 24 hours go to sleep.” You smiled at him leaning up to kiss his forehead. Nodding he turned back over to his side getting comfortable before quickly falling asleep. You were in the kitchen making breakfast as Will slept in your bed when your phone buzzed. A text from an unknown number popping up. Sighing you opened it carefully after making sure you were alone,

“You’re going to get me caught.” His text read accompanied by a picture of his back where numerous scratches clearly covered it.

“Oh fuck. I’m sorry...kinda..” You replied.

“Yeah didn’t think you would be 😏.” He answered before another text came through.

“Listen I think you should know that Erin and I aren’t together. Everyone thinks we are but we aren’t. It’s...complicated.”

“Oh good so I’m the only cheating bitch?”

“Along with a backstabbing brother I guess.”

“What if this is a bad idea? Maybe we should just let this go. Move on.”

“[Y/N], come on. Stop that.”

“I’m just saying is it really worth all the damage this is going to cause?”

“Absolutely, and I don’t care how terrible that is of me to say. There’s a reason he didn’t want us to know. He did this to himself.”

“Yeah okay Jay let’s see how well that argument will go over.”

This went on for about a week. Sneaking around, avoiding Will as best you could. You and Jay talked numerous times about how you were going to tell him, but you couldn’t ever come up with a good enough plan. One that wouldn’t end in a huge argument and inevitably hurting Will once again. You and Will both had off tonight for the first time in a week so he had come over to help you make dinner and watch a movie. You were almost to the end of the movie when Will moved slightly on top of you leaning down to kiss you deeply. Not wanting to be suspicious you kissed back only pushing him away when his hands started to move up your shirt.

“Will. Stop.” You said, halting his hands. Sighing, he rolled back to his side of the bed shaking his head.

“Am I doing something wrong here?” He asked, laughing a little.

“What do you mean?” You replied not meeting his eyes.

“I just mean we’ve been together a few months now and you push me away every time I get even slightly touchy. Not that I need sex. I just don’t understand.” He answered.

“I’m sorry. I’m just not ready. I’m not someone who can just jump into bed with someone.” You explained.

“I didn’t realize doing anything more than kissing would be considered jumping into bed. As if we just got together and I’m some horny teenager. I’m just saying it wasn’t like you made Jay wait.” He huffed sitting up fully.

“Excuse me?” You said appalled, Will quickly catching on at your offended tone.

“Okay, wait that’s not what I-“ He started to cover his tracks reaching for you as you got up walking away from him.

“I want you gone by the time I’m out.” You interrupted slamming the door of your bathroom. You were fuming when you got in the shower only calming down when you realized maybe this was your way out. Maybe you could break up with him now and just play it out. Pulling on a tank top and shorts you walked out, drying your hair happy to see Will still seated on your bed.

“[Y/N] I’m so-“ He walked towards you.

“No, it’s okay. I just overreacted.” You shook your head, tossing the towel into your hamper and walking closer, “but listen. It made me realize that-“ You started going to grab his hands when he cut you off,

“What’s on your chest?” He asked pulling the neckline of your tank top lower to reveal more of the bruise. You gulped noticeably, looking down, racing for any excuse. “[Y/N]. What’s on your chest.” He repeated looking up at you but you started to panic backing away from him, “Tell me that’s not a hickey. Just tell me it’s not and I’ll believe you.” He pleaded pain in his voice.

“Will, just hear me out.” You begged voice shaking.

“You have got to be fucking kidding me.” He laughed bitterly running a hand down his face, “it was him wasn’t it?” He asked, looking back up at you, anger starting to seep into his features. Sighing you felt the tears start to prick your eyes,

“I don’t know what you want me to say.” You finally choked out.

“I want you to tell me you didn’t have sex with my brother. That you didn’t cheat on me with Jay. That’s what I want you to say.” He yelled. Shaking your head and looking down you whispered,

“I can’t do that.” The tension in the room was thick when he knocked a picture on your nightstand across the room in anger making you jump.

“I’m going to fucking kill him.” He growled walking out of your room, slipping on his shoes, and grabbing his keys hurrying out of your apartment as you yelled after him.

“Will come on! Wait!” You called following his lead and running down to your own car slipping in just in time for you to see Will spinning out of the parking lot. Speeding right behind him you tried to grab for your phone before you realized it still lay in the bathroom now panicking more unable to give Jay any kind of heads up. You were in front of Jay’s apartment building within minutes turning your car off just as Will entered. You were hot on Will’s heels following just a beat behind him. Rounding the corner of the stairs just in time for you to witness Jay opening his door and getting knocked back by Will’s fist.

“Will!” You screamed running the rest of the distance to Jay’s apartment.

“No. You stay out of this.” He growled, grabbing Jay by the front of his shirt and slamming him against the wall. You quickly stepped inside shutting the door behind you in fear of any nosy neighbors.

“Will. Let go of him now.” You ordered trying to pull him away from Jay.

“No. It’s okay. He wants to hit me? Go ahead. I deserve it. Just as long as he knows this is his fault too.” Jay challenged hands up in the air not backing down.

“My fault? Yeah cause I distinctly remember telling you to climb into bed with my girlfriend.” He growled slamming him back into the wall again knocking the breath out of Jay.

“You can act like a badass all you want, but there’s a reason you hid everything from both of us. You were bitter that she picked me and knew she would again. You were too scared. This is your fault too Will and you know it.” Jay said.

By now there were tears running down your face and Jay’s eyes kept flickering to you pain and worry on his face as blood ran down it.

“Will...please. Just please let him go and we can talk.” You begged, reaching for his arm again. Will looked between the two of you dropping his hands and laughing bitterly stepping back.

“Whatever. Neither of you are worth it.” He shook his head, moving to the door and slamming it behind him. Sighing you moved to Jay hugging him.

“I’m sorry. I tried to call you but I left my phone and I-“ You cried still sniffling against his chest.

“It’s alright. It’s okay. It’s going to be okay.” He promised rubbing your back. Leaning back you seen blood beginning to dry on Jay’s lip, the bottom of his eye starting to darken.

“We have to get you cleaned up.” You sighed wiping at your face and pulling him off to his bathroom dabbing at his lip before forcing him to hold frozen peas against his eye.

*Not my gif*

Warning: 🍒 18+ Please note that whenever you read these works, you acknowledge you are 18+ and can view such works. 

Withdrawal 🍒

*Not my gif*

Pairing: Kelly Severide x Reader; Jay Halstead/Will Halstead x Reader (Sister)

Requested: Yes

Prompt: What happens when you start having feelings for someone else aka a certain firefighter

Warnings: None

A/N: I’m sorry this sucked

Part 1 here // Part 3 here

It was approaching a year since your boyfriend, Derek’s death. So much of your life has changed since that day. Your brothers had been there for you through thick and thin. One thing was for sure though. You were sick of others opinions. If you went out on a date you were moving on too quickly. If you stayed at home you weren’t letting things go. If you went to a bar with your friends you were drinking your grief away. No matter what you did everyone had an opinion on what you were supposed to do and how you were supposed to feel. The only thing getting you through were your brothers and friends.

You had just walked into Molly’s when you spotted Jay and Will sitting at a table. Walking over and casually sliding onto a chair. They continued their conversation pulling you into it like it was nothing. A few minutes later you decided to go get a drink walking up to the counter.

“The usual?” Hermann asked pulling a cup from the shelf as you nodded smiling sweetly. He made your drink handing it over to you, thanking him as you made your way back to the table. Your night had went by smoothly. Mingling with your friends and drinking anything they handed you.

“I have early rounds. I better get going.” Will announced a few hours later, getting up to grab his coat.

“Can you drop me off at my apartment?” Jay asked moving to stand up too. Will nodded turning to you.

“I’m gonna stay for a little longer.” You replied to his unspoken question.

“Okay. If you need anything my phone’s on.” He reminded you, both him and Jay hugging you before leaving.

You looked around smiling to yourself when you spotted Kelly Severide sitting at the bar watching the game on the TV in front of him. You snuck up behind him quietly, wrapping your arms around his waist making him jump.

“Jesus Christ!” He huffed turning to look at you laugh escaping your lips. “Not funny.” He glared.

“Sorry.” You shrugged still smiling as you sat on the stool beside him. Kelly Severide had quickly turned into your best friend since your boyfriend's death. Besides Will and Jay, Kelly was there to be your rock on your worst days. You had been good friends with Kelly since you had first met years before and he had hit on you before finding out one, who your brothers were and two, that you were taken. There was just something about Kelly that made it so easy to connect with him. So easy to feel comfortable around him. You had sat there talking to him for the remainder of the night until Hermann announced last call, something that was not uncommon for the two of you.

“Alright come on.” Kelly said once the game had finished picking his coat up off the back of his chair. You got up heading towards the door. “Where is your coat?” He asked following behind you.

“It was warm out when I got here,” you explained stepping out the door and immediately shivering, “and it is not anymore.” You laughed. Severide shook his head slipping off the coat he had just put on and threw it over your shoulders. You tried to fight him, but he just shushed you. You gave up quickly knowing it would be a lost cause following him to his car. Starting his car you sat back relaxing in the passenger seat. He turned the radio on as you shut your eyes sitting in comfortable silence. One of Kelly’s hands were gripping the steering wheel as the other was rested on your neck his fingers rubbing in soft circles. In the last few months you and Kelly’s relationship had gotten more serious? Not that it wasn’t serious before it just felt more serious beyond friends, more intimate maybe without the actual intimacy. You had grown to rely on him, and he had grown to be part of your routine. Him driving you home from a night of hanging out at Molly’s was certainly not something new, and you had grown to feel stronger about him. Starting to notice the way his jaw tensed whenever a guy would hit on you or the way his brow furrowed whenever the Blackhawks were losing. Jealousy coming over you for a split second whenever you witnessed a girl hanging on his arm. Feeling more protective or anxious every time you knew he was out on a call. You had felt these feelings before. You had noticed these things in only one other person before and that realization was scaring the hell out of you. The warmth of Kelly’s hand disappearing drew you out of your thoughts. Opening your eyes you realized you were parked in front of your building. You moved to take his jacket off but he stopped you.

“Keep it. I’ll get it whenever I come over next.” He said. You smiled adjusting it back on your shoulders. He was turned trying to fish something out of his door whenever you leaned over to give him a quick kiss on the cheek. He clearly didn’t get that hint whenever he turned to face you again his lips accidentally meeting yours. You both froze feeling the heat take over your body. Giving in to the spark that moved throughout your body you moved your hands up to cup his face pulling him into you for a full kiss now. At your movement you felt Kelly relax into the kiss leaning closer to you. His lips moved gently along with yours. Feeling the most whole you had in awhile. He nipped at your bottom lip before pulling back to get a breath. He smiled at you running his thumb along your cheekbone. You adjusted yourself in your seat

eyes locking with the clock on his dash in the meantime. Immediately feeling your breath hitch you backed away from Kelly. He followed your eyes to see the clock read “2:13am” sympathy washed over his face reaching out to you, “Hey..” he whispered trying to get your attention, but you shook your head.

“Kel..I..I..” You tried to get out, giving up and opting to just get out of his car. You swallowed hard rushing towards your building not looking back. As soon as you closed your door you sank to the floor head falling into your hands. “I’m sorry D.” You mumbled into your hands feeling the guilt sink in deeper.

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

“[Y/N]!” You heard Will’s voice bound throughout your apartment. Groaning you buried your face deeper into your pillows. You heard him sigh heavily before feeling your bed sink. “You have to get up.” He stated moving his hand up and down your back.

“I don’t have to do anything.” You retorted curling further into a ball.

“Jay’s on his way. If he gets here, and you’re-” He started making you huff loudly throwing the covers off of you.

“Fine. I’m up.” You growled. You already knew how this day was going to go. You had been dreading it since the first of the month. At 2:14am Derek would’ve officially been gone for a whole year. 365 days of living your life way differently than you had planned for so long, but you knew the cycle. You knew that if you refused to get out of bed and push on that would only cause a quick downhill slide for you. So, Jay and Will had promised to pull you out. Whether you wanted to or not they were dragging you out of the house. You stomped to your bathroom jumping in the shower refusing with all your power to let the swirling thoughts take over. Whenever you were dressed and ready for the day you walked out to find Will and Jay scrolling through their phones on the couch. Jay heard your footsteps looking up to see you walking into the living room.

“About damn time. Let’s go.” He complained making you roll your eyes and gather your things before following the two out the door.

They had dragged you numerous places throughout the day keeping your mind occupied when all you really wanted was to go home and curl up in bed with piles of food. However, you knew your brothers weren’t about to let that happen. You were sitting in your favorite diner waiting for the waitress to come over with your food when the table started buzzing. Picking you phone up and turning it over Kelly’s name flashed on the screen, for the 5th time that day. Sighing you silenced it sitting it back down on the table.

“Okay that’s like the 10th time that’s happened who’s calling you?” Will asked.

“Nobody.” You grumbled playing with the straw on your drink.

“Is there a particular reason you don’t want us to know?” He pushed.

“It’s not a big deal. Just cause you're my brothers doesn’t mean you have to know every little detail of-“ You began to rant, but were cut off whenever Jay reached over the table grabbing your phone from under your hand. “Hey!” You screamed moving to grab your phone from him but he was already looking through it.

“Severide? Why’s he keep calling you?” Jay asked confused turning your phone towards Will.

“And why do you keep ignoring it?” Will interrogated handing your phone back to you. You stared at them not answering.

“You know we’re going to find out anyway so might as well just tell us.” Jay shrugged making roll your eyes. But their accusing stares refused to leave you. “Fine. Okay. Whatever. Kelly and I kissed last night.” You mumbled as the waitress walked over to give you your orders. You thanked her since Jay and Will seemed to be rendered speechless. You began to eat as they looked at each other in confusion.

“Alright. I’m super confused.” Jay finally admitted breaking the silence. “Since when? How?” He shook his head trying to get out the million questions.

“I don’t know. I guess I’ve been having feelings for him for a while.” You shrugged looking down at your plate.

“Did you know about this?” Jay asked Will pointing at you.

“No, but you’re the detective. Aren’t you supposed to pick up on shit?” Will retorted causing Jay to glare at him. “Okay but..this still doesn’t answer why you’ve been ignoring his calls all day.” Will added.

“I’m avoiding him obviously.” You answered picking a fry off his plate.

“Why?” Jay asked.

“I ran off after we kissed.” You said.

“Can we stop acting like all of this is obvious and normal?” Will scolded you making you roll your eyes. “I’m serious. For what reason did you run off?” He pushed making you sigh heavily.

“It’s not like I can date the guy okay? I shouldn’t have done it and now I’m not sure how to handle it.” You admitted.

“Didn’t you just say you like him?” Jay asked trying to keep up.

“Listen guys a year ago today my life was flipped upside down. Derek was my person. My one. And now he’s gone. I know it sounds crazy, but I felt guilty. I felt like I was betraying him somehow. Maybe all those people were right maybe I was trying to let go of him too fast.” You swallowed hard.

“[Y/N], Derek wouldn’t want you to do this. He would want you to be happy and I know that probably sounds really cliche, but it’s true. He loved you. A lot and there is no doubt he would want you to live your life to the fullest, and that means finding someone who loves you at least half of what he did.” You sat back running a hand down your face taking in Will’s words.

“Can we just drop this for now? Please.” You begged as the nodded changing the subject quickly. After paying you hopped into Jay’s truck heading towards your next stop. You leaned back closing your eyes listening to your brothers bicker about who got to play the music. Feeling Jay put the truck into park about 20 minutes later you opened your eyes to see you were stopped in front of Kelly’s building. “What the hell?” You asked panic rising within you.

“We’re not going to force you to go in, but we really think you should.” Will answered. You looked between them and the building in front of you. You sighed heavily moving to open the door.

“You’re not leaving right?” You asked.

“Not unless you tell us to.” Jay smiled at you. Taking a deep breath you got out of the truck. You knocked lightly on Kelly’s door, hearing shuffling from inside until the door swung open to reveal Kelly.

“[Y/N]! I’ve been calling you all day I was-“ He started before you cut him off.

“Can we talk?” You asked.

“Yeah of course.” He nodded moving out of the way for you to make your way in. Shutting the door behind you he was closely following behind you to his living room where he sat beside you on the couch close enough that his knee was hitting yours. Looking at him you began to play with your hands. “I’m sorry.” You finally mumbled.

“For what?” He asked looking at you confused.

“Running off, avoiding you. I just don’t know.” You admitted. Sympathy took over his features as he reached for one of your hands. “I’m scared. Really scared. Kissing you made me feel something that I haven’t felt in a long time and then...I don’t know I just panicked. I felt so guilty.” You explained. “Everyone had so many opinions on what I should be doing with my life. How I should be handling things. How I should be feeling, and everyone tells me Derek would want me to be happy. To move on. But how am I supposed to know that? He’s gone. It’s not like I can ask him!” You squeezed Kelly’s hand getting worked up. “It’s just one thing after the other and it’s like a nightmare that keeps coming back and-“ You started to breathe heavily.

“Hey. Take a deep breath.” He encouraged. Making you whimper at the thoughts filling your head. “I’m not here to make you feel guilty. I’m not here to rush you. I just want to be here for you. In whatever way you need. Obviously I have feelings for you. I’m not going to deny that, but I’m not here to push you. If you’re not ready the-“ He promised before you jumped in.

“But...I want to be. I loved Derek. I still love Derek. That will never change, but I can’t keep doing this to myself. I can’t keep getting stuck in this cycle of grief or whatever it is. I just...want to be happy again.” You bit your lip looking down in your lap. Kelly’s hand moved to cup your jaw tilting it so you could meet his eyes.

*Not my gif*

Pairing: Jay Halstead x Reader (Sibling)

Requested: Yes

Prompt: Jay is having a hard time after Erin leaves

Warnings: Swearing

Author’s Note: Refers to things in my other imagine “One Day”

“He’s lucky we have our own keys or I’d be breaking the door down.” You sighed to Will unlocking Jay’s front door. You swung the door open and heading straight for the living room as Will followed where you knew Jay would be seated with a few beers, and your assumptions were confirmed as you walked into that exact scene. You went over opening the curtains, letting the sunlight in causing Jay to groan. “Really?” You asked picking his phone up off the coffee table that was set right in front of him.

“What.” He grumbled.

“Your phone is right in front of your face and you’re just going to pretend you didn’t get any of our calls or texts?” You scolded gesturing to Will who sat on the love seat. 

“Just because we don’t have a mom anymore doesn’t mean you need to take over the role. Just because you couldn’t be alone whenever Derek died doesn’t mean I can’t.” Jay said harshly sitting back further into the couch. Will sighed heavily running a hand down his face knowing that Jay should’ve thought before saying that.

“Maybe if you weren’t acting like a child, I wouldn’t have to you jackass. I know you’re having a hard time, but that doesn’t mean as your siblings we aren’t concerned about you, but if you’re going to act like this whatever. Drink yourself to death. See if I care.” You spit out throwing the phone into his lap before turning around and leaving. You just made it downstairs whenever you felt a hand on your shoulder. You turned to see Will.

“You know he didn’t mean that.” Will gave you a look. “You know what it’s like to talk out of hurt.” Will continued.

“Maybe, but that was low.” You huffed.

“Yeah, and you’ve said some stuff just as bad. He’s hurting and he needs us. You know that.” Will reasoned.

“Fine. I’ll be back later, but I need some space right now.” You gave in which Will took as a win kissing your cheek and heading back upstairs. You had left and ran some errands, getting the three of you dinner after you reminded yourself that Will was right and you had said some pretty hurtful things to the both of them in your stage of grief. You cared the food upstairs opening the door that was still unlocked and walking in to lay the food on the counter in the kitchen. From the kitchen you could see Jay and Will seated beside each other on the couch watching the Cubs game, but also in conversation. Jay seemed to be in better spirits since before you left, no doubt thanks to Will and his smooth, intelligent way around words. You cleared your throat as they both looked up at you. “Brought food.” You mumbled pulling it all out of the bags. They both got up walking over to help you. The room was filled with awkward silence until you made your way into the living room sitting down in your normal seats. Jay on the far end of the couch, you on the other end, and Will on the love seat beside you.

“I’m sorry.” Jay sighed looking over at you.

“No, it’s alright. I understand.” You answered.

“You were right I was being a jackass and I shouldn’t have brought that up.” He said taking a bite of his food.

“Yeah, but I get it. You’re hurting, you’re going through some stuff, and sometimes you can’t control what you’re saying. Obviously I’ve been there. That doesn’t mean we’re going to leave you alone though. It’s part of the sibling handbook.” You laughed making Jay smile slightly.

“I just can’t believe she’s gone you know? Like I know she’s not gone gone, but she’s not coming back.” He sighed playing with his food a bit. “It’s just the little things that remind me of her. Like her shampoo she left here, or the way her pillow still smells like her.” He swallowed.

“I liked Erin. I did, but if she’s okay with leaving like that, without a single word to you-” You started before he cut you off.

“But I left her first. I can’t really blame her.” He answered.

“Jay, we all have issues with relationships, none of them are perfect, none of us are perfect, but how you guys went about your relationship, how you guys dealt with things it wasn’t healthy for either of you. You have to work together and you guys didn’t. In your relationship at least.” Will contributed.

“I just miss her.” Jay admitted.

“You loved her. That’s not going to go away, but you will get through it. So many people go through heartbreak and they come out stronger on the other side, and you’re not going to be any different. You’ve been through much worse.” You added.

“Let’s be real bro you’re a catch. You have girls throwing themselves over you all the time. You’ll have plenty more to choose from.” Will pointed out making Jay smile bigger.

“You’ll move on. You will. It might take a while, but you will. You just gotta have faith in the process.” You reassured squeezing his shoulder.

“You’re the little sister. Aren’t we supposed to be giving you advice?” Jay chuckled seeming more relaxed now.

*Not my gif*

Pairing: Jay/Will Halstead x Reader (Sister)

Requested: Yes

Prompt: Brothers are there for everything

Warnings: Death by drunk driving, grief, mourning

Part 2 here // Part 3 here

This couldn’t be happening. Not to you at least. Will had tried everything he could. You knew that, and you also knew he didn’t want to be the one to tell you that Derek didn’t make it. Yet he was. He got stuck with that job. You knew it wasn’t good coming in, you could hear it in Jay’s voice, but you just didn’t want to accept it. Even when Will told you he was gone you still didn’t want to accept it. You had gotten mad at Will. It was his fault. He could’ve saved him. That’s what he went to school for. That’s what he’s supposed to do, and yet he let your boyfriend die. Eventually though you realized that was all just your anger speaking. The denial of the situation coming to a head and you had quickly apologized to him knowing that it wasn’t his fault and knowing he did everything he could have possibly been able to do. Regardless you just couldn’t figure out how to move past it. You had planned to spend the rest of your life with Derek, and now you were coming home to emptiness. You were coming home to his dirty bowl still laying on the table, his shirt you had discarded off of him the night before that never made its way back on or off the floor, his toothbrush still in the bathroom, his clothes still in your closet, the side of his bed still disheveled from that morning. You couldn’t bring yourself to pick up any of it. You couldn’t bring yourself to get rid of him. It was all you had to feel like you were still connected to him. Yet you couldn’t bare to look at these things. You couldn’t handle realizing that this was all you had left. So, your brothers offered you a place to stay and you were taking turns staying at Will’s and Jay’s depending on their schedules. They had done everything they could to make sure you weren’t alone. To make sure they were there for you through it all.

“Are you sure?” Jay asked again as the three of you stood at the door of your apartment. You had not been in your apartment since the night it happened. You just nodded your head not trusting yourself to speak, not really knowing if you were actually sure. It had only been a few weeks, but you were doing your best to move your life forward piece by piece. Will sighed at your hesitation opening the door walking in before you. You followed him in slowly taking a deep breath looking around. You noticed that the bowl was no longer on the table. That broke you a little, but was something you could move past. The blanket that was thrown on the floor from the night before in your lust state was now neatly laid on the back of the couch. You swallowed hard at that one. You walked around looking and taking it all in. It was as you had left of him for the most part, but everything that had him in it was now gone. As you walked into the bathroom you noticed his toothbrush was no longer set beside yours, and that as stupid and little as it may seem was your breaking point as you let out a sob that came all to quick. Jay and Will were at your side in seconds guiding you over to the couch.

“How could you do this?! How could you get rid of him so easily?!” You screamed at them through sobs. They didn’t answer knowing that you didn’t mean to put the blame on them. They were just the only ones there you could blame. They sat beside you rubbing your back taking turns soothing you. Once you ran out of tears you ran a hand down your face looking at the floor. “I’m sorry..” You whispered as they both assured you it was okay. ”I’m so angry.” You admitted sitting back up. “I’m so angry that someone took him away from me all because they wanted a few drinks. All because they decided to get behind the wheel when they couldn’t even walk straight. It’s all his fault and he gets to live without more than a scratch. It’s not fucking fair. I don’t get it...how am I supposed to move past this…” You asked head in your hands.

“Just like you have been. One step at a time.” Jay replied.

“The pain is never going to go away. We all know that, but one day it won’t be as strong. One day you will be able to move on. One day you will be able to smile again, and one day you will feel whole again. I promise…” Will said pulling you into a hug. You leaned back in between them looking up at the ceiling.

“Thank you for being here for me, and thank you for cleaning up the mess of my apartment.” You joked leaning your head on Jay’s shoulder and wrapping an arm around Will’s bicep.