NITW boyfriend/girlfriend scenarios and oneshots

Gregg x shy nonbinary reader part 1 |Sleepless Nights|

(Yes I changed the reader to non-binary since Gregg is gay and I wanted to make sure the actual game characteristics were still there)

You woke up at 3:30 a.m...again. This was the third time this week and it was only Thursday! You went over to your computer and saw three messages from Gregg. Gregg was your bestie but after the years you began to gain a bit of a crush on him. It was a mess since you knew he would like you back. After all you're a shy individual, who could like someone as pathetic as you? Nobody. That was the answer...nobody.
(Ding)
Your computer set off again, a message from Gregg read-
"Dear (Y/N), I'm free today if you would like to come over to the apartment. You can come over anytime you want to even right now if you want! I know you've been having problems with sleeping and Angus and I know some things that could help! Seeya in a bit!
-Greggory"
Wow. I can't believe he would actually message you this early. Maybe someone doesn't pity you and instead cares somewhat? Maybe he does care, maybe he doesn't you didn't care. You packed your stuff in your old school backpack and snuck out the window of your room. Being on a higher floor always had advantages since you could climb straight on to the power lines.

You arrived at Gregg and Angus's apartment and knocked on the door once. The door swung open to reveal Gregg standing in front of you with a happy and excited smile.
"Geez (Y/N) I didn't think you got the message! Thank god ya did though! I was so bored! Now we can do whatever we want!" Gregg almost yelled.
"Other people are here so please keep it down. And my parents don't know I'm here so try not to make it seem obvious." You said thinking about your parents yelling at you even though you were old enough to move out. You shivered are this though which Gregg seemed to notice immediately.
"You ok buddy? I'm kinda worried about you and your sleeping issue though all jokes aside." Gregg said in coaxing manor. He sat down on couch while you sat on the floor. Gregg seemed super surprised by your action and stared at you for a minute. You recognized this almost immediately.
"Is something wrong Gregg?" You asked calmly.
"Yeah! Sorry for staring...I know a way we can both get some sleep! I'm not sure if you would enjoy it very much though because of how shy you are typically..." Gregg said somewhat sadly.
"Actually anything would help...so shoot!" You said excitedly.
"Well...I'm gonna sound so dumb asking this but...would you...like...to..." He didn't say anything for a minute lost in though but eventually just asked it up front.
"WOULDYOUMAYBELIKETOSLEEPTOGETHERORCUDDLE???" Gregg spat out quicker than he usually spoke which was pretty fast.
"Ummm...actually yes I would like to try it or...something..." you said shyly. You had never dated anyone before so this was a bit sudden. You hadn't had your first kiss, cuddled, or really even shown or been shown any affection from or to anyone. It also surprised you how Gregg for once was being shy like you usually were, it was a nice change of pace.
"So...umm..." you said nervously not knowing what to do or say.
"If you've never cuddled I can teach you if you'd like..." Gregg said calmly. It was surprising how Gregg could be shy one minute calm the next, and then back to his normal self. Wow.
"You wanna sleep in the bed...or the couch...umm..." you said stuttering constantly.
"How about we cuddle on the couch and move it to the bed once we get tired ok?" Gregg said back to his normal self.
"Umm...sure..." you said stuttering.