One Chicago x Reader

First Time w/ Matt Casey

Pairings: Matt Casey x Fem!Reader

Featuring: Matt Casey, Y/n

Summary: Matt pops y/n's cherry.

Warnings: first time, sex, smut, unprotected sex [wrap it before you tap it], errors I missed.

w/c: 848

His touches were delicate. Taking your clothes off gently. Laying you down on the mattress like you were made of glass.

Kisses ever so soft, yet passionate.

Both of you were naked. Your hands trailed down his exposed chest. Gulping slightly. This was your first time.

Matt grabbed underneath your chin. Bringing your head up to look at him. You stared into his blue eyes which held concern.

"Are you sure you want to do this? we don't have to if you aren't ready or scared or have any doubts, I don't want you to feel pressured," Matt asked.

"I want to, I want you to be my first," you responded. Matt still looked unsure.

Your hands cupped his jaw. As you starred into his eyes.

"I want to do this Matt, I am hundred per cent sure," You reassured him. Never breaking eyes contact. Matt smiled at you. Still worried.

"It will hurt," He spoke. He was worried you would freak out as soon as he slide into you.

"I know, but I know you would never hurt me, and you will be as gentle as you can, please Matt," You begged. Matt still looked concerned.

"Okay, tell me to stop if it gets too much for you," Matt spoke. As he looked at you once more. Seeing if he could see any signs of regret.

Matt grabbed his shaft, aligning it with your entrance. he looked at you s his tip touched your wet folds. You let out a whimper. Nodding your head.

Matt slowly entered you. Making your face distorted into discomfort. It broke his heart.

"Maybe we should do this another time," He spoke.

"No, keep going," You spoke.

Matt slowly slides into you. Making tears fall from your eyes.

"Y/n, I-" Matt started to say but you cut him off.

"It's okay, baby," You sniffled out. Grabbing a hold of his forearms squeezing tight.

"Your crying," Matt pointed out. at this point, he bottomed out.

"It's just, it is uncomfortable, but don't worry," You spoke.

Matt grabbed a hold of the side of your head. Lowering his lips down to yours. Kissing you softly. trying to distract you from the pain.

Which worked. You were the first one to pull away from the kiss. Making Matt open his eyes. Looking at you. He thought you were in pain still.

"You can move," You reassured him. Matt stared at you for a second. Studying your facial features.

"Okay but tell me to stop if you get uncomfortable. I will go slow," Matt spoke ever so softly. you smiled at him.

Matt slowly pulled out the thrusted back in gently. One of his hands grabbed your hip, while his other hand held your hand. intertwining his fingers with your fingers.

Matt slide into you again, till he bottomed out.

"Just remember it's all about you, don't worry about making me come," Matt spoke, as he looked at you. you nodded your head.

"Just tell me to stop, if it gets too much for you," Matt reminded you. Making you smile.

"I know," You responded.

"I'm going to pull out, then enter you again," He informed you. as he pulled out slowly then entered you gently.

Matt Thrusted in and out of you at a slow pace. Trying his best not to moan.

You felt slight discomfort first till the pain and discomfort faded into pleasure.

You wrapped your legs around his waist, as quiet moans escaped your mouth. Head lolling back. Closing your eyes.

You begged Matt to go a little bit faster but his thrusts were still slow.

"Please," You begged him. Matt gave in. Slightly spending his pace up a bit, but not too much.

Grabbing the side of your face with both hands, he moved your head so he could kiss you.

Kissing you passionately. You felt your stomach tighten as an unfamiliar sensation formed.

Moaning into his mouth. As intense waves of pleasure pulsated through your body before you came. Slightly dazed from your orgasm.

Matt wasn't too far behind you. climaxing hard. His moans were muffled by your lips.

Matt pulled his lips away from yours, pressing a soft kiss on your shoulder, as he gently pulled out of you. Making you tense slightly.

You turned your head to look at Matt. Noticing that he was already looking at you.

"How do you feel?" He asked you. Grabbing hold of your hand. Intertwining his fingers with yours. Bringing your hand up to his lips. Pressing light kisses on your knuckles.

"Great, tired, thank you, that was truly amazing, I can't wait to have more intimate moments with you," You replied. Making Matt smile.

"Do you want water? Do you want me to draw you a bath or turn on the shower?" Matt asked. You shook your head no.

Snuggling into his side. Resting your head on his chest. Matt let go of your hand.

"I just want to take a nap," You spoke, As you closed your eyes. Matt wrapped his arm around you. Kissing the top of your head....

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