Prompt #8: "Are you wearing my shirt?"
The first time Jay caught Hailey wearing his shirt they were at work. She had come out of the locker room a few minutes ago with a familiar looking black hoodie on. It was very plain, so it wouldn't have been too noticeable except for the size. It was definitely a little loose and big on her. He didn't want to say anything though because he'd hate to sound like a wishful fool if he was wrong. However he is suspicious because he hasn't been able to find his favorite hoodie in weeks. If he's being honest with himself he would love for her to be wearing it on her own. It would make him feel like it was her way of being close to him without voicing her true feelings. It would also give him another perfect opportunity to tease her. He's been studying her across their desks for the past few minutes trying to analyze inconspicuously, at least he thought he was.
"What?" Hailey pops her head up from what she was doing and looks at him, sensing his eyes on her.
"Are you wearing my hoodie?" Fuck it, he'll just flat out ask.
He catches a slight blush rise in her cheeks and her bite down a small smile that flashes her dimples. She looks almost bashful and he finds it completely adorable.
"Yeah, I uh, I was cold." She finally murmurs.
"Oh, that's fine. But where did it come from?"
She seems to blush even more. "I ended up taking it home that night you let me borrow it at your place. When we were watching 'The Boys' and you wouldn't raise the heat."
"It was on 70, Hailey, for you by the way! Hardly freezing." He teases.
"ANYWAY, I wore it home and washed it that weekend with the intent to give it back. But then I put it in my locker... and was kind of hoping you forgot about it because it comes in handy at times like this." She replies guiltily, but flashing him her widest puppy dog eyes in hopes he won't care.
Jay laughs heartedly. But he doesn't want to let her off the hook too easy. "You know, I've been looking for it for weeks!" He deadpans, which isn't a lie.
"Oh, I'm sorry. I'll give it back to you after shift."
"You know what? Keep it! It looks better on you anyway." He grins at her when her face brightens again.
"Ya sure?"
"Absolutely!"
"Well, now I know you're BSing because I do kind of swim in this, but I really love it. It's very warm, and still kind of smells like you."
She admits that last part before she could catch herself. They share a charged look and Jay can't help but to feel utterly gleeful inside. They only get pulled out of their spell when they hear Kevin and Adam barreling up the stairs debating over something. It's enough to make them remember where they are and for Hailey to try to backtrack.
"I mean, you know, that smell of leftover Portillo's fries and musty cologne." She teases and Jay sees right through it.
"Mhmm. I'm glad you like it. So beer on you for the next month?"
Her eyes go wide and she scoffs. "Fine, but only because my place is warmer!"
Jay grins at the whole exchange one last time before getting back to work. Hoping one day to see her in his shirts for other reasons...
The second time Hailey was wearing one of his shirts it was more known to him. The team had agreed to go to Molly's that night since they hadn't been in a while, but Jay and Hailey were stuck working a little later meeting a CI. When they were finally done they decided to grab some takeout and eat it at Jay's before hitting the bar. They ordered from their favorite Italian place and Hailey ended up spilling some pasta sauce on her white shirt. After having a good laugh together over her attempt to clean it, turning it basically into a wet t-shirt contest look with a faded stain, they knew it wasn't salvageable to make the bar. Since they didn't want to get to Molly's even later, Jay offered up one of his shirts. It was a green button-down that she was easily able to tuck into her jeans and that actually looked pretty good on her slightly unbuttoned, her skimpy tank top working well underneath. Jay tried to contain himself from drooling too much and they finally were on their way to meet their crew.
It wasn't unusual for Hailey and Jay to arrive to places together, especially since the team knew they had been working late. But it didn't stop all eyes from turning to the two of them as they made their way to the table. Adam and Kevin were snickering slightly, and Kim and Vanessa were giving knowing looks. Used to this by now, the two ignored them and Hailey sat while Jay was about to hit the bar.
"Anyone need refills?" He asked.
"No, we're good." Vanessa replied for the group since they were all fresh on their drinks.
Jay made his way over to the bar as Kim started studying Hailey. She did her best to ignore her, but curiosity finally got the best of the blonde detective.
"What?" She asks Kim.
"Is that Jay's shirt?" She asks back while Vanessa nearly gets whiplash moving her head back towards their conversation.
"Uh, yeah. I spilt some pasta on my shirt at dinner so Jay gave me one of his."
"Oh, is THAT what we're calling it now?" Kim jokes cracking her and Vanessa up.
"Shutup!" Hailey laughs slightly embarrassed, even though she knows her answer is the truth.
Jay comes back over with their beers and Kim can't wait to tease him too. Hoping there's more to the story.
"That's a really nice shirt Hailey is wearing. Interesting you never offer me or Vanessa to borrow your shirts."
"I was going to give her pants too, but then we thought it'd be more obvious." Jay cracks up at his joke as the girls' eyes go wide.
"JAY!" Hailey scolds. They'll never hear the end of this now.
"I'm kidding, I'm kidding. She got sauce on her shirt, what do you want from me?" He backtracks so Hailey doesn't kill him.
"What kind of sauce?" Vanessa wiggles her eyebrows.
"Oh my God! That's it, I need a shot!" Hailey says suddenly hot and hopping up to head to the bar.
"She really does look good in your shirt." Kim tells Jay.
"I know, that's what I said!" He grins wickedly, egging them on even more. Hey, maybe one day they'll get their scandalous reason...
The third time Jay caught Hailey wearing one of his shirts they had been undercover as a couple for a few weeks. While they didn't have to stay in their UC apartment too often, they did have to keep up appearances on certain nights. They were trying to infiltrate a drug den that was working out of a bar, and the police department had found a way to get the bar owner to rent them the upstairs apartment as their in. It had been working marvelously. No one questioned that they were a happy couple willing to settle for a crappy apartment, especially when unlimited liquor was a walk down the stairs. And secretly Hailey and Jay were having a blast with it. There honestly wasn't much to "sell" of them being a couple, they practically were.
They were about to head down to the bar for the night when what Hailey was wearing caught Jay's eye. He smiled to himself and thought, again! This time he didn't even have to study her for long knowing he instantly recognized that flannel she was wearing over her crop top. His pulse raced not only from the sliver of her abdomen showing, but seeing her in his clothes yet again. It was starting to become a habit. Still, he can't help but to tease her every time.
"Are you wearing my shirt?"
She smiles at him through the bathroom mirror as she applies the last of her lipstick. "Yeah, I figured it would help further sell how legit of a couple we are. I hope you don't mind I grabbed it off the top of your duffel bag."
"No, no, it's fine. It looks good on you. In fact, all my clothes look good on you. I'm starting to really like it." He replies with a little bit of huskiness to his voice.
Hailey tries to stifle her small gasp. "Jay..." she softly warns.
The past few weeks of playing these rolls have started to blur the lines of their friendship even more. Nothing has fully happened to cross them yet, but they've been close. There was one drunken night after all their brief kisses for show down at the bar that they almost went further in "their apartment." But luckily (or unfortunately to both their subconscious's) Jay's personal phone started ringing with Voight calling in for his nightly check-in. They sobered up after that.
"I'm just saying, I don't mind seeing you in them..." he whispers his reply.
"We should head downstairs. Tony should be dealing with his regulars by now." Hailey tries to stop the beating of her heart and move another almost-moment along.
"Yeah..." he lets his reply hang as they both stare at each other and grudgingly start to make their way down to the bar.
A few hours later they were satisfied that their hidden cameras recorded a lot of useful info on Tony and his for-show bar staff. He was in jovial spirits tonight, so his guard didn't seem to be as up as normal. They had been playing along with the drinking for a while now and Tony came over to start to bullshit with them.
"I'm glad you guys took my Ma's piece of shit apartment up there. I like you! She was begging me to fill the vacancy and there's not many I trust, but you guys have been solid!"
Jay takes that as his cue to keep up the ruse and drapes his arm around Hailey, pulling her closer. She smiles up at him as they both nod back at Tony.
"You know us, all we need is a warm bed and we're happy!" Jay grins wickedly at the drug dealer and gives Hailey a wink.
"Sometimes just a clean floor!" Hailey adds in, playing along.
Tony's eyes go wide in approval. "Oh, to be young and in love, and still so naive! You better hold onto this one, Ryan." He says to Jay using his undercover name.
"I intend to!" Jay replies pulling her even closer into his side.
Tony gets pulled away by one of his staff after that, so they just hang amongst themselves and play along a bit longer. Closer to the end of the night Jay is playing pool with some locals to gather more intel while Hailey is hanging with a couple of the other girlfriends. A guy they've never seen before starts making moves on Hailey and Jay notices instantly from across the room. He gives her a few minutes to try to wean him off herself, but when she seems to be unsuccessful he's by her side in brisk strides.
"This guy bothering you, babe?" He asks while possessively grabbing onto Hailey again and giving the dude a menacing look.
"I tried to tell him you were my boyfriend, but he thought I was making an excuse."
"Is that so?"
Jay raises his brow and then does something he wouldn't be as brazen to do if it weren't for their covers. He grabs her neck and pulls her towards his face as he leans down and kisses her, throwing all of his pent-up longing into it. This wasn't one of their quick and brisk for-show kisses they've been doing, this was passionate and intense and for a moment they forgot that they were playing as Ryan and Kelly. This was all Jay and Hailey. They were so lost in each other they didn't even notice the guy had walked off in disgust already, moving onto the next girl along the bar. After a couple minutes they finally broke away breathlessly and looked at each other with want and confusion. Eventually it was Hailey who spoke first.
"You don't think that was a little bit of overkill?" She whispers, biting down on her lip and trying to hold in her smile.
"Maybe... but that guy and everyone here should know it's MY shirt you're wearing!"
He smiles back affectionately at her. And it's not until they're back upstairs in their fake apartment that Hailey realizes he never let go of his possessive hold of her for the rest of the night...
The fourth time Jay caught Hailey wearing one of his shirts she was finally his. They had been together about a month now and he'd never been happier. After years of friendship, trust, and longing, they fit perfectly together in this new role. Everyone at work and those they were closest to were happy for them as well. Today had been one of those rare Sunday's they had nothing going on; and after Hailey wore him out the night before it had also been one of those rare days of him sleeping in a little later. He woke up to an empty bed and the smell of coffee and bacon wafting from his kitchen. He made his way over to it and took a moment to ogle Hailey. She was turned away from him at the stove wearing nothing but his Blackhawks jersey. It was so big on her it practically reached her knees and he had to gulp hard. He swears it's the sexiest sight he's ever seen.
She hadn't heard or sensed his presence yet so he decides to use that in his favor. He slowly walked up behind her to wrap his arms around her waist and tuck his face into her neck, kissing it gently before whispering in her ear.
"I see you're wearing one of my shirts again..."
She shivers and giggles loudly. "Yup! You have a problem with that?"
"Nope! This one looks even better on you than the others." He says while kissing along her jaw.
"Good because I really don't intend to give this one back!" She teases.
He lowers his hands to her thighs and starts running them under his jersey, slowly dragging it up her body. "I'm more concerned with taking it off of you!" He chuckles softly, teasing back.
She feigns trying to shoo his hands off of her and focus on the sizzling bacon in the pan, trying to speak sternly, "After breakfast."
He reaches his one hand back up to turn off the stove completely. "Breakfast can wait!"
He barks out before turning her to face him, lifting her and wrapping her legs around his waist.
"JAY!" She screams out in laughter.
He moves her to sit on the counter and then leans in to silence her with a passionate kiss. She doesn't need much convincing after that. Jay pulls back eventually to lift his jersey off of her, finally doing what he's wanted to do since he first saw her in one of his shirts. As good as she looks in them, she looks even better out of them... and he's never been happier than being able to show her just how much he loves it, and her!
[A/N: This prompt was requested by "cpd5021" and two "guests." I actually wrote this one on my phone's notepad app while at work, so hopefully it turned out ok. So excited that filming will be starting in a few weeks & episodes are back in November! FINALLY! Thanks for reading and hope all is well.
*List of prompts is at the bottom of first chapter*]