Prompt #22: "Isn't this, like, illegal?" … "Probably."


Quarantine was starting to get the best of Jay and Hailey. It was already August and while things had gone a tiny bit back to normal in Chicago, it wasn't nearly enough. They found they had no time or privacy together, which was ironic because this would seem like the perfect time for the opposite. They were swamped at work because there were massive eyes on the police at the moment, tons of protests- some perfectly peaceful, others not so much, drama surrounding poor Kevin and the corrupt cops now out to get him and the unit, and crime now back on the rise since things were slowly opening and people felt they had to make up for the time they felt trapped indoors for months. Then on the personal front, with not much to do, Vanessa was always home so it's not like they got any alone time at Hailey's. And Jay's also became out of the question because one of his old army buddies was crashing on his couch for the time being. A little after quarantine started he had been shipped home early from Germany and with the pandemic going on he didn't have a place to land on his feet quite yet. Jay felt bad and took him in, to his own dismay, knowing it was the kiss of death of him or Hailey progressing any further in their relationship at the moment. The two of them were exhausted, angry, bored, and sexually frustrated… not a good mix.

It was a bit of a downer because both of them had such high expectations for when Hailey returned from New York. They were finally ready to spend every waking moment together and they couldn't. Maybe it was for the best, they say "slow and steady wins the race" and that statement seemed to encapsulate their partnership to friendship to whatever this was for almost four years now. Still, it didn't make the pill any easier to swallow. Tired of waiting for 2020 to right itself on its own, Hailey decided to take matters into her own hands. She walked to the end of Jay's desk while everyone was wrapping up in the bullpen for the day and leaned in like she was looking over his computer.

"Meet me outside your place tonight at 9, I'm coming to pick you up." She whispered.

Jay raised his brow at her. "To do what?"

"It's a surprise. Just be out front and dress coolly." She said before grabbing her bag across her own desk and turning to head out.

"Okay…" he said questioningly, secretly turned on at Hailey being so cryptic.

Ever so prompt, Jay was sitting outside his apartment complex by 8:45 dressed in shorts and a t-shirt. He was feeling equal parts excited and nervous. It had been weeks since he and Hailey spent any time alone together. He was pretty confidant she still wanted them, but he couldn't help the butterflies in his stomach like it was his first date with his dream girl… which, technically maybe it was, depending on what she had planned. Hailey arrived right before 9 and Jay got up to walk over to her Jeep. He laughed when he saw her extending a coffee to him from the passenger window, but his mouth dropped when he saw what she had on. She was wearing the golf outfit she bought for one of the charity events they went to last year. Jay hopped in the car and stared at her.

"What the…" he started to say, wondering out loud why she was fitted for golfing when it was already completely dark outside.

"Didn't they ever teach you it's not polite to stare?" Hailey teased as she put the car in drive and took off.

"Where are we going and why are you dressed like that, Hailey?"

"I told you, it's a SURPRISE!" she smirked at him. "By the way, the coffee's Irish." She added a wink.

"Spiked coffee and you all cute in golfer's attire? Are you trying to turn me on?" he grinned.

"Wow, Jay, is that really all it takes? I should have done this years ago then!" she blushes when she realizes how that sounds and see his eyes raise at her. "But maybe!" she boldly finishes.

"Huh." He quietly says sipping on the coffee as the two of them get silent just enjoying being in the other's company as Hailey takes them to their secret destination.

About thirty minutes later they're pulling into a golf course right on the outskirt of Lake Michigan. Jay's still looking on in wonder. It's clear and apparent the course has been closed for a couple hours now. Since no one else is around, Hailey could pull her car right up to the entrance gate and park, but she opts instead to park towards the back near some trees in hopes to not draw any unwanted attention.

"I stole your clubs out of your trunk at work today and put them in mine." She says as if it all makes complete sense.

"What are we doing here, Hailey?"

"We're gonna go golfing, what's it look like?"

"At night? Course is closed."

"I understand that, Jay, but you've gotten no time to otherwise. We've been working too late and it's too busy on weekends that even when we're off I know you haven't wanted to go. Plus, this is the perfect time for us to be alone." She smiles cheerily at him.

"Seriously?" he asks still in shock. "You've complained every time I've asked you to golf with me."

"But I've gone, haven't I?" she bites back. "Besides, it makes you happy and we could all use a bit of happiness right now."

"You're something, Hailey Upton. Have I told you that? The more I learn the more…" he lets the remaining thought hang.

"Shutup! Let's go." She says fighting back her blush as they make their way to her trunk to pull out their clubs.

"One of my CI's caddies here on occasion. I slipped him some cash to leave one of the golf carts on the 2nd hole when he left for the night." She says proudly like she's thought of everything as they sneak behind the front building and up onto the course.

"Isn't this like, illegal?" Jay finally voices, thinking it this whole time but trying not to kill the mood.

"Probably… what, are you scared of getting caught, Detective?" she teases.

"Oh, it's so on. And you're so losing!" Jay says excited now that they're up at the 1st hole and he knows he's finally completely alone with her without invasive coworkers, sweaty criminals, or always-home roommates.

They enjoy the walk over to the next hole, casually and purposely walking close and along each other, their shoulders brushing on occasion. By the time they get to the cart and start driving the rest of the course they're laughing and carefree, feeling lighter than they have in months. They're halfway through on the 9th hole when Jay realizes he's only a little ahead of her score wise. He starts to get fake pouty as he drives them over to the next hole.

"I can't believe I'm only a few strokes ahead of you. I'm the one who actually likes this sport. Is there nothing you're not good at?"

"Aww, don't be a sore loser, Jay. Besides, you've never complained about my strokes in the past." She leans in over her seat and whispers as they both laugh.

"This is true. But it's been a while… I think you may have to show me those strokes again." He says huskily ever so close to her lips.

"Is that so?" she murmurs into his mouth as he nods excitedly, neither caring where they are anymore.

He brings his hand to her head and pulls her in for a kiss, hot and full of fury, releasing all their tension of the past few weeks. They both moan into each other's mouths as Hailey leans over more and straddles him on the seat. The kiss seems to go on for hours, even though it's only minutes at most, they're stuck in their own little world. Hailey starts moving her hand to his shorts when Jay moves his along her bare thighs under her skirt and up to the thong she purposely put on when she changed. Jay lets out a guttural moan at feeling so much skin and things are about to tick up a notch further when they sense a light shining on them. They quickly break apart once they hear the shout of a security guard.

"HEY! What are you guys doing here? This is private property."

"Shit!" Jay gasps and slams on the cart accelerator the second Hailey adjusts her skirt and hops back into her seat.

"HEY, GET BACK HERE!"

They hear the guard yell again, his cart coming closer and Jay speeds back to the beginning of the course, cutting in and out of trees to get there faster; all his years of defensive police driving coming in handy. The guard is close, but not close enough. They make it back to Hailey's car and throw the clubs haphazardly in her back seat as she grabs her keys and they speed out of the lot just as the guard hits the pavement of the entrance. Now back on the main road and in the clear they burst out laughing.

"Oh my God, we just got caught necking like teenagers!" Hailey exclaims.

"Yeah well, my hormones are feeling like a teenager right about now." Jay jokes.

Hailey smiles back and gives him a mischievous look as she takes a quick turn leading towards the lake instead of back to Jay's. She parks along the water and Jay gives her his millionth surprise stare of the night.

"I brought a beach blanket too." She shrugs nonchalantly, like she literally planned for everything.

Catching on quicker this time, Jay grabs her hand as they get out of the car and starts dragging her towards the beach. They decide on a secluded area together to finish what they started; not wasting any time adjusting clothes and attempting the backstroke this time. It's nearly an hour later when they're finally catching their breath again, and it having nothing to do with the adrenaline of out running the golf security.

"Mmm, this was definitely illegal." Jay manages to say while nuzzling her neck, his arms wrapped tightly around her, enjoying her quiet contentment as she trails her fingers along his arm.

"Oh, definitely. But it would be the funniest call to Voight we would ever make." She joked. "Remember when Vanessa almost caught us on my first night back?"

They both smile at the memory of knowing they left their clothes strewn about her living room, barely making it into her bedroom before Vanessa unlocked the front door. Her roommate gave her such shit the next morning, not even caring to catch up over the teasing.

"I do. I think the fear of getting caught turned me on even more, if that's even possible around you." He said, pulling her even closer against him.

"Maybe we should buy a sleeping bag and make this our weekly spot?" she finally replied, listening intently to the calm of the waves crashing in the distance.

"Weekly!? Unt uh, Hailey, I hope you mean nightly. I don't know how I made it this long between times before tonight. Longest. Summer. Ever. After waiting for you for the longest time ever. We have to up our alone time game!"

"So demanding after sex, Halstead. I am going to need a bed eventually."

"Fine, I'll buy us a cheap hotel room." He grins against her ear.

She laughs hysterically. "Classy!"

They chuckled softly into the night, falling asleep in each other's arms. They woke before dawn and made their way back home before getting caught. As fun as a headline of "Naked Detectives Captured" would be, they decided their coworkers will have a field day teasing them enough when they fess up they're together. And honestly, they can't wait.


[A/N: Well guys, this was the fourth prompt, #22 requested by: "yournameisyours," "chicagogirl2," and a "guest." Sorry I haven't done combos yet or connecting storylines really, but maybe one day, we'll see. Thank you for such positive response to these, I'm so happy you're enjoying them. Hope everyone is staying safe, sane, & well!

*The list of prompts are at the bottom of the first chapter if anyone wants to request one.]