This was requested by xx_MissInsanityXD_xx! I hope you enjoy it!!
Jeff:
It was New Year's Eve, and you and Jeff had been best friends for awhile now. Of course, you had always been secretly attracted to him, but you never told him for, well, obvious reasons.
"Hey Y/N, the ball is about to drop! Come watch!" Masky shouted to you from the living room. You ran in, taking a seat beside Jeff. The countdown started, and then, everyone shouted, "HAPPY NEW YEAR!" "Y/N?" You looked over to see Jeff staring at you. Before you could answer, he grabbed your face and smashed his lips against yours. Needless to say, it was going to be a good year.
BEN:
You were sitting on the couch next to BEN, your boyfriend. You two were playing some video game when suddenly, he paused it and looked at you with a devilish grin. "Lets make a bet." You raised your brow, coaxing him to continue. "The loser has to do whatever the other tells them to. Deal?" You shrugged, agreeing. Moments later, BEN knocked the controller out of your hand, causing you to lose. "Hey, you cheated!" you pouted. "I still won," he beamed. "Fine, what do I have to do?" you sighed. "Kiss me." You stared at him, making sure you heard him right. Once you realized what he had said, you happily obliged, smashing your lips against his.
Slenderman:
You and Slender we're walking through the forest, admiring nature when he stopped, grabbing your hand in his. "Y/N, there's something I want to do, but I feel as if I need to ask you for permission." "What is it, Slendy?" You asked, tilting your head slightly. "I just..May I kiss you?" His question caught you off guard, but you soon nodded, allowing him to softly press his lips to yours.
Masky:
You and Masky we're playing the question game, asking each other everything and anything. "Who's your best friend ever?" you asked him, even though you knew the answer. "Hoodie!" he grinned behind his mask. "I knew it!" you giggled. "Who was your first kiss?" he asked curiously. "I um.. I've never kissed anyone before." you blushed, looking down. "Well..May I be your first?" he asked you before raising his mask slightly, pressing a gentle kid to your lips.
Lost Silver:
You and Silver had been together for a month now, and you were starting to wonder why he hadn't kissed you yet. There had been plenty of opportunities, and you started to wonder is he was attracted to you anymore. "Silver, can I ask you something?" He nodded. "Why haven't you kissed me yet? Is it because you don't like me anymore?" He froze in his seat before answering, "N-No! That's not the r-reason at all! I really, r-really like you Y/N. I-I've just been too scared.." You smiled at how cute he was, leaning in and kissing him softly. He kissed you back happily, and you were both grinning afterwards.
