Everything One Chicago — Always Have, Always Will ~ Part 2

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Always Have, Always Will ~ Part 2

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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.

“I didn’t mean for this to happen.” You shook your head, dropping it into your hands. This was not how you planned for this to go down.

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