Slenderman~ You were having terrible insomnia one night, causing you to wake Slender. "Dear, I can't sleep..could you sing me a song?" Slender smiled to himself with a blush before bringing you closer to him. He began to sing Sweet Dreams (Are Made of These) by Mariyln Manson, which instantly lulled you to sleep.
Jeff the Killer~ You and Jeff were out late on a date, which made you exhausted. The two of you crawled into bed, Jeff's arm snaked around your waist while his other hand stroked your hair. You were almost asleep when Jeff starting to sing Heart Shaped Box by Nirvana, making your night even more perfect then before.
Ben Drowned~ You were resting your head on Ben's chest, trying to take a nap. Ben continued to play his game, resting his chin on your head. He noticed you having troubles sleeping, making his lips come to your ear "Need help falling asleep cutie?" He asked. You nodded and smiled, causing him to sing Time of Your Life (Good Riddance) by Green Day.
Eyeless Jack~ "Jaaaaackkkk, I can't sleeeeeeeeeppp." You whined. Jack chuckled and hugged you tighter "I'll make you go to sleep." He jokingly threatened. "Yeah, you should. Sing me a song Jackie, pleeeeeeeeaaaa-" "Okay okay , I'll sing you a song babe." He said defeated before singing Fairely Local by Twenty One Pilots.
Laughing Jack~ You were laying in bed, waiting for Jack to come home and trying to take a nap. You pulled the blankets closer to you, when you felt someone pull you into a sideways cuddle. You smiled knowing it was Jack while he softly rubbed your back. He kissed your cheek and began to sing you asleep with The Joker by Steve Miller Band.
Masky~ "Sing me a song babe?" You asked Masky as you cuddled on the couch together. He brushed your hair back with his fingers, shaking his head. "Nah, I'm not that good.." He admitted. "What are you talking about, you're amazing!" You exclaimed. Masky chuckled and sang Sirens by Pearl Jam for you, making you instantly fall asleep.
Hoodie~ You two were at the park late at night, thinking that it would be fun for the two of you. He pushed you on the swings for a little while, before the two of you layed on the grass, your eyes threatening to close. Hoodie smiled under his mask, carrying you home and singing Diamond Eyes by Shinedown to you, making you fall asleep before you even got home.
Ticci Toby~ "Whatcha doing YN?" Toby asked, laying down next to you. You pulled the pillow off your head before sighing "Trying to sleep, but I can't.." Toby hugged you close and kissed your forehead. "Maybe a song will put you to sleep." He suggested before singing Bring Me To Life by Evanscene.
Lost Silver~ You were cuddled up on Silver's chest, almost asleep. You felt his lips softly touch yours, making your eyes fly open. "Y-You're so cute.." Silver admitted. You blushed "Do you want a song to fall a-asleep to?" He asked. You smiled and nodded before he sang Me and Mary Jane by Black Stone Cherry.
Homicidal Liu/Sully~ "Goodnight baby." Liu said, kissing your head. "No no no, I can't sleep yet." You protested. Liu raised an eyebrow "Why not?" He asked. You smiled "I need a goodnight lullaby to fall asleep to." You said. Liu snickered before singing Lips Of An Angel by Hinder to you, making you instantly fall asleep.
