Descendants Oneshots and Headcanons!!

Ruby x G!P Kylie~ Quickie 💕✨🖤🏳️‍🌈

Kylie stared at the ceiling, her skin boiling. She was so angry that she wanted to cry, tears pooling at the corners of her eyes before she blinked them away, sighing. It had been so bad recently.. she'd barely gotten any sleep because of it the past week or so, and she was at her breaking point. Her erection pulsed in her boxers, pressing against her pants in an almost painful way, but she just couldn't bring herself to touch it, make herself feel better. In a way, she liked the pain.. it reminded her of how worthless she really was, how she hated her body, and that every waking moment she would be reminded of how much of a mistake she was.

She stifled a sob as she tried to reach a shaking hand down to touch herself one last time, but of course she couldn't do it. She let out a pained whine like a wounded animal as she clutched her hair desperately. "I JUST WANT SOME FUCKING SLEEP!.." she yelled out in the darkness, to no avail. She turned over and squeezed her pillow to her chest tightly, just wishing she had someone to hold her... Wait. Ruby was in this hotel.. she knew about Kylie's... difference... Maybe she could offer some comfort? ......or..

"No!! What the hell?! I've known her for over a decade, she's like my sister.. I'm not asking her for sex!! That'd be weird!...." Kylie sighed as she lowered her eyes, thinking about Ruby. ".....but it'd also be really hot... And.. then maybe I could finally fucking sleep." She groaned at the fact she'd already made up her mind as she put on her slippers and wrapped a dressing gown around herself loosely, to haphazardly cover her erection in case she was to bump into someone in the hallway, even at this time of night.

She trudged her way to Ruby's hotel room, a few tears falling as she stared at her door, her hand in the knocking position but not actually moving, only quivering. She gently tapped a couple times, hoping Ruby would somehow coincidentally be awake AND hear her pathetic excuse for a knock. Kylie's breath hitched in her throat as she heard soft footsteps approaching the other side of the door, before she heard the slide and click of the lock as the door opened and the beautiful blonde's face was revealed. "H-hi Ruby..." Kylie's voice cracked, and Ruby looked very concerned.

"Ky? Are you okay..? You look upset.. come inside." Ruby moved aside so Kylie could shuffle in beside her, and Ruby locked the door as Kylie went to sit on the edge of her bed. Ruby sat next to her, looking her in the eyes with nothing but love and concern for her friend as she gently placed her hand on Kylie's. "What's up?.." she spoke softly, with a voice like honey that caused the dam of Kylie's built up tears to break. She collapsed into Ruby's arms sobbing, all the while Ruby was whispering sweet nothings into her ear and comfortingly rubbing her back through her dressing gown.

When Kylie calmed down a bit and regained control of her breathing, she couldn't use words, so she stood up, untied her dressing gown and let it fall to the floor, revealing her painfully hard boner. Ruby's face flushed, but she didn't say anything at first, a little lost for words. "Uhm.. w-what did.. what did you want me to do about that?" Kylie croaked out a response, "C-could you.. please, rub it? I-I can't.. and I can't sleep.." her face clearly threatened more tears if Ruby didn't react accordingly, so she gently guided Kylie to lay down on her bed as she planted a kiss on her cheek.

"It's okay, Ky.. you know I'll always look after you, even if that includes doing this sort of thing for you.." she giggled sweetly as she gently pulled down Kylie's pajama pants, then her boxers, and gripped her erection before starting to gently squeeze and stroke it with a rhythm. Kylie immediately groaned and softly bucked into her hand, "F-fuck, ..I really need this..~" She continued to moan as Ruby jerked her off, Ruby biting her lip watching her friend desperately buck into her palm like a dog in heat. "You look so cute right now, Ky..." After a few minutes of lustful stroking, Kylie was starting to feel too good to handle, "D-don't stop... Fuck, Rube! This feels so good!..~ ah~, ahhh~" Ruby giggles, "You look like you're enjoying yourself~"