Here's my first Simon imagine. Enjoy!
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You have been at the sanctuary for a couple of months now. You have been best friends with Negan since we both were twenty three. You knew everything about each other. He knew of your crush on his right hand man, Simon. He was funny and you loved being around him when you would go to The Hilltop. Negan always teased you when you would get back. You was sitting in his office one day.

"Negan, why must you tease me so badly about my crush on Simon every time we come back," you asked.

"Because it's fun to see you red as a tomato and can barely form words around Simon when I joke about you two fucking and that's why you was gone so long," Negan explained.

"Well, can you put a stop to it?" you asked.

"(Y/N), (Y/N), (Y/N), where's the fun in that?" Negan said, laughing.

"Well, if you know what's good for your manhood, you'll stop," you said," It's hard enough talking to Simon without your little jokes."

"Whoa, there's my fiery best friend," Negan said," Now, go tell Simon how you feel."

"You like Simon?" Amber asked, laughing.

"Yeah, and if you don't want a beating from me, you'll kept your mouth shut," you said, as you left.

You walked to your room and stay there all day. Simon tried to get you to go to The Hilltop, but you lied and said that you was feeling sick. He looked a little upset, but left anyway. It was dinner and you was hungry from not eating on day. You was walking down the hall to the mess hall. You saw Simon walking towards you. You froze when you saw him. Your heart beat faster as he stopped in front of you.

"So, a little bird tells me you have a thing for me," Simon said, smirking.

Simon got closer towards you but you kept backing up until you hit the wall behind. Simon got close and put his hands on by side of my head. You started to feel scared being this close to Simon. He got close to your ear.

"Well, sweetheart, I have a thing for you, too," Simon whispered.

You smiled that your long time crush on Simon and you finally knew that he felt the same. Simon kissed you and you giggled as his moustache tickled you face. He pulled away and smirked.

"What's so funny, sweetheart?" Simon asked.

"Your moustache is very tickled my face," you answered, giggling.

"Maybe I should shave it then," Simon said, touching his moustache.

"No, I actually like it," you said, putting your arms around his neck.

"Really?" Simon asked, hands on your waist pulling you closer.

"Yeah, I kind of have thing for guys with facial hair," you answered.

"Good to know," Simon said, before he kissed you.

You two pulled apart when you heard clapping. You saw Negan was standing there. He put his arms around you two and smirked.

"It's this nice, my right hand man and my best friend together," Negan said," Glad you two are happy together."

"You're okay with this?" you asked.

"Who do you think told Simon about your thing for him?" Negan said, walking away.

"Okay, then," you said.

"So, will you be my girl?" Simon asked, pulling you closer to him.

You pulled away and walked away. You turned and walked backwards.

"You coming, boyfriend," you said," I'm starving."

Simon chuckled as he caught with him. You two ate dinner together. You felt more relaxed around Simon, now that your feeling are mutually out there. You was happy spending everyday with the one you care about. Things was tough with the walkers around, but you and Simon enjoyed every second of every moment of everyday together. You knew that there would be chance that you both would die from the walkers or people in this crappy world, but he made sure you was happy everyday. You was glad that he finally knew your secret crush on him.

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I enjoyed writing this one. Comment and let me know what you think. Oh, leave your requests in the comments and I'll get them done as quickly as I could.