Kendall Jenner Imagines

Musician

Requested by @Lisapaul55 : Could you do one where Y/Nis singing in a park and Kendall comes up to her after a show

Singing, it was your passion and you had hoped you could get somewhere with your voice. That's right you're like all the other aspiring singers and actors in Hollywood. You had gotten yourself a bit of a following though, 50k Instagram followers. Tonight you were playing a show in the park, anyone was free to come.

Your best friend aka "manager" as she likes to call herself was helping you make sure you have everything. "Y/N aren't you going to change?" She looked at you in disapproval and you looked at her confused. You had on a red flannel, blacked ripped jeans and a beanie. "Why would I? I think I look great" You stated and she turned the other way grabbing your guitar. "Whatever you say Y/N here's your guitar" She handed you the instrument and you put it in your car.

"Oh Y/N we need a photo to promote your show" She advised and you nodded. She grabbed her phone and snapped a photo of you and handed started to type in the info. "Thanks Chloe" You hugged the girl as she smiled to you. The two of you got in the car and you used bluetooth to play music and both of you were jamming to whatever was playing.

You both started setting things up when her boyfriend came to help you guys out. You guys were laughing and fucking around while setting up and once you guys finished you guys all sat in a circle as you strummed on the guitar. "Ooh make a song about me" Carter asked and you nodded. You started to play the guitar "Carter you smell really bad, and you are really stupid and you think that you are perfect but-" You sang but you were cut off by Carter tackling you. "Shut up" You all broke into laughter.

30 minutes before the show you actually started to practice when Carter made conversation with you. "Hey maybe you'll see a hot girl here" He said wiggling his eyebrows suggestively, you shoved him softly when he smiled at you. "Y/N I know you'll be big one day" He patted your back getting up and going to Chloe.

When their was 15 minutes before seven a couple of teens started to show up. You decided to talk to them and some of them had listened to my music before and some hadn't. They were all very sweet and you guys snapped a few photos when you saw it was time. You looked to the crowd and saw about 20 people. You were happy that people showed up.

"Hey guys I'd like to thank you guys for coming, I hope you enjoy" You flashed the crowd a smile as you started to play the guitar and you sang. 10 minutes later 20 people turned to 50. Everyone seemed to be enjoying it, people had their phones out some were taking videos some were taking photos and others didn't even have their phones out.

You were shocked by all the people crowding, you were taking a quick 5 minute break and you had Carter entertain the crowd. You ran to Chloe as you started to freak. "Chloe that's well over a hundred people" You jumped and so did she. "Go back out there" Chloe turned you around and pushed you back to the stage. Carter smiled at you and sent you a thumbs up and walked off the stage.

"Before I proceed I'd like to thank you all for being here this means the world" You resumed singing your next song, you hadn't even noticed but you saw Kendall Jenner, Hailey Baldwin and Gigi Hadid in the crowd dancing to you. This had put you in a state of pure happiness.

"Thank you guys for coming out here and listening to my music, you guys are the fucking best" Everyone cheered out and you smiled. "If you guys want I'll be taking photos and stuff" You hopped off the stage and a bunch of people lined up and started taking selfies with you.

"Your music is the shit" A girl said and you smiled at her, after everyone was done taking photos you were met face to face with Kendall Jenner. "Hi, I'm Kendall" She stuck her hand out and you shook it nodding. "I know you're Kendall Jenner, I'm Y/N" She smiled at you. "You're really good at singing, my friends and I enjoyed the show" She complimented and you sent her a big smile. "Thank you so much" She nodded and pulled out her phone. "Put your number in and we can hang or something" You nodded and typed in your number and handed the phone back to her. "Well I've got to go, I'll see you around" She walked off and went with her friends when you ran to yours.

"Kendall fucking Jenner came to my show!" You exclaimed and the three of you started to fangirl. You grabbed your phone to see that your follower count went up, you were now at 200k. Your eyes widened as you showed your friends. "We need to celebrate" Carter said and you and Chloe both nodded in agreement.

The next day you were sent a text from the model, she wanted to hang out. You of course responded yes and you were going to meet up at her place. You got in the car and drove to Kendall's, on the way you thought about how lucky you are for this.

When you got there you knocked on the door, she answered and smiled bringing you in. You were met with the one and only Justin Bieber. "Y/N meet Justin, Justin meet Y/N" Your eyes widened as you shook the pop star's hand. "Ken showed me a vid of you singing, it's really dope. I was wondering if you'd wanna collab?" He asked and you tried your hardest to contain your excitement. You saw Kendall smiling as she stood in the door frame.

The three of you sat down and talked, came up with ideas for your collaboration, both of them were very laidback and chill. You knew you were definitely going to get along with them. You started to write some lyrics that sounded good and by the end of the night you had a song written. You checked the time and it was around 2am. "Hey guys wanna sneak in the studio and record a demo?" Justin suggested and the two of you nodded getting in the car.

When you guys got there Justin pulled a key out. "We shouldn't be in here but whatever" You guys slipped in and turned on the lights. "We need proof we were here" You said pulling out your camera, before you took the photo Kendall pressed her lips to yours right as you snapped the photo. "We have scandalous proof" Kendall smiled and took a seat. You on the other hand stood there in shook bringing your hand to your lips, Justin smirked at you before walking into the recording area.

When you showed the demo everyone loved it and wanted to start promotion. Photoshoots, interviews and things like that. You spent most of your free time cozying up with Kendall. You were really into her and you were contemplating wether you should ask her out or not. You came to a decision that you'd do it big; you were going to ask her first time you preform the song with Justin.

The media went crazy seeing you, a new upcoming star and Justin the biggest star making music. The song and the music video was going to be released today and it had Kendall in it. Today you were preforming it live so you were planning to ask her out, if she said no it would be embarrassing but you have to take risks in life, right?

You and Justin were back stage as you felt your heart racing and Kendall started to comfort you and she was rubbing your arm. "It's ok, you're gonna do great out there" You looked up to her and smiled, you wish you could tell her that wasn't the reason why you're such a mess.

When you got out there you and Justin had a good time, dancing and all. The crowd seemed to enjoy it and everyone was having a good time. When the two of you finished the song you started to talk. "Hey everyone, I'd like to talk for a moment and thank you guys for one and I have a question you guys know Kendall Jenner, right?" The crowd cheered and you smiled, you were gaining confidence from the crowd. "Well let's bring her up here" She came out on stage looking a bit confused. "Kendall I was wondering if you'd like to go on a date with me?" You asked and the crowd roared and she nodded pressing her lips to yours.

"I'd love to go out with you" She smiled.

(A/N: I'm going to see ARIANA TONIGHT WOOO, anyways I'm back and updating so hope you enjoyed this)

REQUESTS ARE OPEN!