One Chicago Imagines

Middle of the Night (Hailey Upton x fem!reader)

tw: mentioning of some anxiety [ romantic endeavors, romantic feelings, new sexual endeavors ], wlw smut and angst [ mommy!kink, dom/sub, edging, degradation!kink, praise!kink ], wlw fluff [ after-sex fluff, comfort fluff, kissing ], mention of a car accident, cursing

pairings: hailey upton x fem!reader "friend" (lol)

hey babe, don't forget to vote & feel free to comment !! love ya always <3

You had been working at the precinct alongside Hailey Upton for a while now. A few months ago, the two of you were in a really bad car accident together. The car flipped, and although you were able to break free of the seatbelt, Hailey was stuck upside down in her seat, unconscious. You saved her life. Not too long after that life-changing experience together, you realized you had feelings for Hailey. And boy, did you fall for her — hard.

Unable to sleep, you decide at 1:30 am one night to head over to the precinct. A little while after you arrive, you hear footsteps walking upstairs, making you jump and swing around with fear in your eyes.

"Hey, Y/N. Sorry, I didn't mean to scare you!"
"Oh, my God. Hi, Hailey!" you croak, your face turning red.
"You okay, Y/N? You look a bit... flustered," she laughs, throwing her keys on the desk.
"No, I'm fine! W-What are you... doing here?"
"Oh, I couldn't sleep, so I figured I'd just come in early today. What are you doing here?"
"Yeah, same," you say, licking your lips nervously.

Oh my God, oh my God, oh my God! Why does she have to be so hot?

"Y/N? You sure you're okay?" she chuckles, furrowing her eyebrows at you.
"Yeah!" you practically yell, making your face heat up even more.

She shrugs it off, and the two of you sit down at your desks and start working on case files, listening to the radio in case anyone in the city needs you. Being there alone with Hailey is making you feel like puking and jumping for joy at the same time.

At around 2:30, your heart is beating out of your chest as you finally decide to turn over to Hailey, placing some files down first with shaky hands.

"Yes?" she asks, making you blush again.
"Um..."
"You seem off tonight, babe."

Hearing the pet name causes a wave of butterflies to erupt in your stomach. The unexpectedness of it makes you feel uneasy, but... in a good way; in a... seductive way.

You look at Hailey, and she intently stares back at you with those gorgeous, bright blue eyes.

Neither of you smiles or even smirks. You're just staring each other down, watching the love and lust building in the other's eyes without words.

Hailey rises out of her chair, taking a small step closer to you. Your heart skips a beat.

You feel your breath catch as you stand up, too. You feel frozen in place.

Hailey slowly walks up to you, maintaining intense, lustful eye contact the entire time. She slowly wraps her arms around your neck, leaning in to kiss you. She wants you and makes it extremely obvious as she passionately pulls you in closer, clasping her lips onto yours.

You slide your arms around her waist with a sharp inhale, the feeling of her warm body pressed up against yours making you so fucking wet. The two of you fall into a graceful yet powerfully intense rhythm as she begins to add some tongue, causing you to let out a small whimper.

You suddenly get the motivation to do something you've never done before: take control. You spin around and push her up against the wall, making her grunt as she slams back onto it.

She tightens her grip around you, pulling your waist and hips up against hers, both of you gasping for air through your kisses.

You decide to take it one step further by leaving a trail of naughty nibbles down to Hailey's neck. She lets out a soft moan when you find her pressure point, digging her nails into your arms as you suck her, biting lightly.