You were out on a run with Simon and a few other men when you came across a warehouse a few days away from the Sanctuary. You found it was stocked full with all sorts of items for a super-center from before the apocalypse. You and his men started to go through all of the boxes and found there was a lot of useful stuff to bring back to Negan. You were just about to start loading up boxes in the trucks, but Simon ordered everyone to leave it for the morning. It was late, and you had all day tomorrow.
Locking the doors and double checking that the warehouse was safe, the handful of men that were with you were relieved to even find a few mattresses at the back of the warehouse. Setting them up and eating their packed dinners, everyone visited a bit before turning in. After an hour, the warehouse was filled with snores from all the Saviors. You laid awake staring at the ceiling, and felt a shiver run through your body. You were freezing and couldn't sleep.
Getting up and grabbing your flashlight, you carefully moved off your mattress and stepped around your sleeping comrades. One of the men had a leather jacket that he had set down on a box, and you picked it up and pulled it on. In a few moments you were feeling much better and warmed up. Being wide awake and curious, you made your way through the rest of the large warehouse and decided to look for anything else that you could bring back to the Sanctuary.
You came across a sporting goods section and saw a long box. You set the flashlight down on the floor and opened it. Inside, you found a wooden bat and you removed it, taking it into your hands. You swung it around a few times, imagining you were playing softball like you had when you were a child. Then, you looked down and realized as you stood there with your bat and jacket that you looked like Negan.
You laughed to yourself and decided you were going to complete your outfit. Heading to where the clothing was, you rummaged through some boxes until you found a long red dress. Taking out your knife, you cut a long strip from the fabric and tied it around your neck.
Looking down and feeling amused with yourself, you started to swing the bat back and forth and said in your best Negan voice, "Fucking fuckers!" and giggled.
Suddenly, you heard someone clear their throat from behind you, and you spun around to see who was watching you. Your cheeks turned bright red to see Simon standing there with an amused look on his face and his arms crossed.
"Having fun?" he asked, leaning to the side and taking in your little cosplay.
You narrowed your eyes and pointed the bat right at him.
"Kneel!" you ordered, in a commanding voice.
Simon laughed low.
"Seriously?" he asked, cocking his head to the side and looking at you amused.
"I said kneel!" you said louder, and he put his hands up in mock defense.
"Alright! Alright! I'm kneeling!" He started to get down onto his knees and looked up at you. You marched over and glared down at him.
"Don't fucking talk back to your fucking leader!" you ordered, doing your best to keep a straight face, but struggling to do so. Simon was pressing his lips together tightly, trying not to burst out laughing at your attempt to sound like Negan. You felt your lip twitch or a brief moment, but held it together.
"I expect better from my right-hand man," you scolded, and started to pace in front of him. You put the bat over your shoulder and then moved back in front of him and leaned back very dramatically.
"He would beat your skull in if he saw this right now," Simon sneered, shaking his head and grinning.
You leaned your face very close to his, your expression sour.
"I'm talking, Mr. Mustache!" you barked.
Simon let out a loud laugh.
"Mr. Mustache? Really?"
You couldn't help but break character to smile as he teased you for the crappy nickname. Negan had always been able to come up with such colorful lingo, and you were doing your best to impersonate him.
Simon continued to laugh for a while and then he looked up at you, still very amused.
"So, my big scary leader… what would you have me do?" He raised an eyebrow at you and then you watched as his eyes trailed down your body, only stopping to linger on your exposed cleavage.
"I'm up here, mister," you growled, moving the bat underneath his chin and lifting his head up so he was looking into your eyes.
"Yeah, but those tits are right there," Simon said, pointing right at your chest. You rolled your eyes and moved the bat away from him as he continued to ogle you.
"You stare at Negan like this too?" you teased him, and gently hit his arm with the bat. He licked his lips and continued to stare.
"Negan doesn't fill out a leather jacket quite like you."
His compliment made you blush, and you looked away from him, but he still noticed.
"Tell me what you want me to do," he whispered in a low voice, making you turn back to him. He was looking at you in a new way, like he wanted you. His eyes were filled with lust. As you stared down at Simon, you wondered if it was time to cut this off. You had worked with him for months and things could end up getting complicated.
"Stand up," you ordered, and he did, eyes never leaving yours. Once he reached his feet, he took a few steps towards you and you got back into your Negan character.
"I want you to-" you started to command, but you were cut off as Simon cupped your face with his hands and kissed you hard. The feeling of his lips against yours shocked you at first, but a second later you realized you wanted this.
No, you needed this.
You kissed him back and felt the prickle of his mustache against your soft skin. You dropped the bat and it clanged against the floor loud as you wrapped your arms around his neck and pulled him in closer to you, making him groan.
You had just started to trail a hand down his chest when someone coughed from across the room, making you both turn your heads to the sound. Not wanting to wake anyone up, he grabbed your hand and led you outside in the cool night. You looked at him as he pulled you along towards one of the trucks and walked around to the backside. Opening the truck bed, you both climbed up into the back and continued where you left off inside the warehouse, wrapping your arms around one another and kissing passionately.
You went to remove the leather jacket, but Simon's lips left yours.
"Leave it on," he ordered, moving a hand to your chest and pressing so you laid down. He leaned over you and his mouth found yours again, and he started to suck against your bottom lip. As he continued to kiss you, you felt yourself get more turned on. Lifting your legs up a bit, you pressed your lower half against him and felt his firm erection.
As if the contact gave him the go ahead, Simon sat up and moved a hand down to unzip your pants. He pulled them down your legs, and then his fingers slid against your panties. They were absolutely soaked and as he felt the dampness through the thin fabric. He hissed through his teeth.
"Roleplay turn you on?" he asked, turning to look at you with a wide grin.
"Shut up," you groaned, lifting up on your legs so your bottom half brushed up against his hand.
Simon rubbed his hand against your panties making you moan loud. He covered your mouth with his other hand as he continued to rub.
"We still gotta keep it down. Don't need those roamers crashing our little party."
You nodded and watched as he moved his hand away to unzip his pants, his cock practically jumping out hard as a rock. He moved his body so he was over yours and took his hand to move your panties to the side a little bit. You couldn't help but cry out as he pressed into you.
Simon was big and as he moved in and out, your walls clenched around him tight. You moaned even louder than before, not being able to control the sounds of pleasure. Knowing you needed to keep it down, you moved the red makeshift scarf towards your mouth and bit down against it to muffle your moans. The sight seemed to turn him on even more, because Simon sped up his thrusts and started to fuck you even harder. You cried out into the scarf as he filled you entirely and then pulled back out, only to push in again and again.
Your hands gripped the truck bed desperately trying to find something to hang onto as Simon continued to thrust. You looked up to see he was watching your covered breasts bounce up and down as he moved you with every push. The look of desire, and the feeling as he hit every right place brought you over the edge and into the abyss of an incredible orgasm that travelled through your body like a jolt of electricity.
Simon's movements started to become erratic, and you felt him thrust one last time and then pull out. Holding his dick, he lifted your shirt to expose your stomach and came onto your skin. Once he finished, he pulled the red scarf away from your neck and mouth and used it to clean you. He tossed the scarf away and collapsed next to you; you both were breathing hard as you laid in the truck bed.
You were surprised that you weren't regretting this at all. At first, you had been worried that this would make things complicated with Simon, but when you were with him, all your doubt faded away.
Sitting up a bit, you turned and looked at him.
"Not bad, Mr. Mustache. Not bad," you said teasingly.
Simon let out a loud laugh and turned to look at you.
"Sure, but next time I wanna be Negan," he insisted "and you can kneel."
