So, I actually wrote this over a year ago, but at the time Simon wasn't even a character option for on here, and so being unable to tag him as a character in the fic meant I didn't see the point of putting the story up on here. Well, now he is finally an option on the character list on this site, so I guess it's past time I put this 2-chapter fic up on here for y'all to read, if you haven't seen it on other sites already. Enjoy!

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You were standing in the front entryway of Gregory's house, along with Jesus and a few other members of the community. However, you were vastly outnumbered by the Saviors, who filled the usually large-seeming space, their serious expressions and weapons making you feel small and insignificant.

Gregory was currently inside his office with the door closed…and he was in there, as well.

You had been Gregory's housekeeper for months now, so you should probably feel some sort of loyalty towards him, seeing as how he was the leader of Hilltop and all. But, if you were being honest, Gregory was a real douche. He was condescending to everyone, and he never thanked you for your hard work. Well, unless being constantly looked up and down salaciously and called inferior nicknames such as "honey" could be considered a thank you.

Now, Simon, on the other hand…there was a real man. It was your dirty little secret that you had it pretty bad for Negan's right-hand man. Every time he jumped out of that big, blue pickup truck, you felt your breathing accelerate in excitement. He wasn't handsome in the stereotypical way that had been revered by post-apocalyptic societal standards. His hairline was receding, and he had a handlebar mustache that would've been humorous-looking on a less intimidating man. But there was just something about him that made your thighs clench and clit pulse every time you saw him.

Maybe what you found so attractive was the way he carried himself, all self-assured and full of confidence. Or maybe it was the way his arms bulged in that button-down shirt, giving just a taste of the lean, corded muscles that were hiding underneath. Heck, maybe it was even the way he had Gregory cowering before him with every visit…the way he gruffly told him to kneel at his feet…which caused you to then imagine your own knees hitting the hard floor, so that you could unbuckle his pants and….

You were distracted from your internal fantasies by the study door opening. Gregory came out first, with Simon following a few steps behind. Your breath caught in your throat when Gregory made a beeline for the closet where Maggie and Sasha were hidden. Glancing at Jesus, you saw panic and helplessness cross his face. Everything seemed to stall, as if it were happening in slow motion. And when Gregory's hand reached out for the closet doorknob, you felt yourself take a step forward, mouth opening without you even fully processing what you were about to do.

"Wait."

Gregory froze, his head turning and eyes looking at you, both confusion and annoyance crossing his features. But you weren't really paying attention to him, because Simon had also turned his head, and his gaze was fixed on you, as if unsure how to react to your interruption.

Realizing that you needed to get him away from the closet, before Gregory went through with opening the door, you nodded at Simon and hurriedly stated, "I need to speak with you…alone."

Surprise widened Simon's eyes slightly, his lips pursing thoughtfully before he nodded. Lifting his arm back in the direction of Gregory's open office door, he announced, "Well, alright then. After you, darlin'."

Turning, you caught Jesus' gaze, his expression questioning, but there was no way for you to respond without seeming suspicious. Walking across the foyer, you entered the study and walked over to stand in front of the large, mahogany desk. Shifting nervously, you watched as Simon closed the door behind him, then took a couple steps into the room.

He stopped a few feet away from you and cocked his head curiously before saying, "So, girlie, what was so important that you had to interrupt?"

Shit. You hadn't really thought this far ahead. Searching your brain frantically, you tried to think of a plausible excuse for this "meeting".

"I, uh…there's something you should probably know about."

"I'm all ears, sweetheart," he replied.

You tried not to blush at his endearment. While Gregory's pet names always sounded creepy and slimy, Simon calling you "sweetheart" and "darlin'" sounded endearing…and even sexy.

Deciding on what was hopefully a plausible explanation, you shifted your eyes down to the floor and divulged, "Gregory has some supplies that he hasn't been telling you about. He, uh…he has a whole cellar full of alcohol. Boxes and boxes of it. Scotch, mainly, but I think there's some gin and whiskey in there, as well."

When there was no immediate response, you lifted your gaze and saw that Simon was looking at you, almost scrutinizing in his perusal of your face, as if he could discover all your secrets if he stared hard enough. For the first time ever, you had his full and undivided attention...and your body's traitorous response was to blush. The heat that flared on your cheeks had to be apparent, and you swore that Simon's lips twitched upwards briefly on one side, as if in amusement.

Taking a step closer to you, he hooked a thumb in his belt loop and drawled, "Now, why would you tell me that, hmm? What would make you wanna sell out your pansy of a leader? Because I can't imagine that you're telling me this just out of the goodness of your heart."

Much as you wanted to come up with some elaborate excuse, one that would quickly get him out of the study and away from Hilltop, you realized that this situation could also go an entirely different route. That this could be your one and only chance to make all your hidden fantasies and secret lust a reality. You could get the satisfaction you had been craving, Maggie and Sasha would remain safe, and Gregory would take a hit to his pride with all the liquor gone. Win-win all around.

Gathering some courage, you replied, "I was hoping that in exchange for that information, you might give me something I've been wanting for a while now."

Curiosity lit up Simon's eyes, and he chuckled before cocking one hip and taunting, "An exchange, you say? Well fuck, sweetheart. Tell me what it is that you want, and we'll see if we can't strike a deal."

You swallowed nervously before squaring your shoulders, looking him right in the eye, and saying, "What I want…is you. Right here, right now. One hell of an orgasm in exchange for all of Gregory's liquor. That sound like a fair trade to you?"

From the way his mouth silently parted in surprise, you could tell that he hadn't been expecting such an offer. Suddenly, you felt self-conscious. What if he wasn't interested? What if he laughed in your face and walked out?

You were about to backtrack and try to turn it all into some big joke, when you saw his eyes finally leave your face. They trailed down over your body, which was modestly covered in a navy-blue t-shirt and jeans, before slowly scanning back up again. When his gaze connected back with your own, he had a fiery glint in his eyes, and a smirk slowly spread across his face.

"Darlin', I do believe that's the best god damn offer I've ever received." Flickering his eyes down over your body again, he licked his lips and drawled, "How about you go ahead and show me what kind of high-quality goods I'm dealing with here."

Arousal flooded you at his words, at the fact that the offer had worked…that he wanted you, too. Hands trembled slightly as you reached down and grasped the edge of your shirt, pulling it up and over your head in one smooth motion. Thank god you had put on a clean bra today, this one a soft peach color that complimented your skin quite nicely. You unbuttoned your jeans and pushed them down your hips with a wiggle before kicking both them and your sneakers off, leaving you in a pair of light pink panties. The underwear didn't exactly match the bra, but hey, you hadn't exactly expected to fuck your apocalyptic crush when pulling them on this morning.

Simon's eyes were fixated on your body, and he gave a breathy, "Fuck," before he reached up and started undoing the row of buttons on the front of his tan button-down. You watched greedily as his chest was revealed. He pulled the shirt free, shrugging it off his shoulders, before then pulling his thin, white undershirt up over his head.

You almost stumbled at the sight of him naked from the waist up. Jesus fuck, he's ripped! You had guessed that he was in shape, but you had no idea that he was hiding such a fine physique. His biceps bulged as he started undoing his belt, his chest muscles and six pac abs flexing underneath a layer of dark hair. He was so strong and masculine that you almost forgot to breathe…and you hadn't even seen his cock, yet.

He walked towards you, belt undone but pants still on, his arm reaching out and wrapping around your waist to pull you in against him. Your palm collided with his warm chest, and you shivered as the soft hair on his abs teased your sensitive stomach. You tilted your head up towards him just in time to meet his lips with your own. You had never kissed a man with a mustache before, and the sensation was a bit foreign, but not unpleasant. His tongue danced with yours, and you gave a soft moan when he gently captured your bottom lip between his teeth.

He reached down and cupped his hand over the curve of your ass before murmuring against your lips, "Yep, I'd say that you're by far the finest quality of woman I ever have seen…and felt." With that, his hand gave a firm squeeze, and you pressed closer into him, giving a hum of pleasure as you ran the hand laying on his chest down his taut stomach and over the front of his pants.

"Feels like you've got some high-quality goods, yourself," you purred, cupping his hard dick through the fabric.

He rewarded you with a groan, hand coming up to grab your wrist and lift it away from his dick, while he spun you away from him to face the desk. You felt his hands unhook the clasp of your bra, brushing the straps down your arms and flinging it across the room. You gave a moan of appreciation when his big, warm hands wrapped around your torso and cupped your breasts, the nipples instantly hardening for him. He rolled the swollen nubs between his fingertips, his lips and teeth nipping at the back of your shoulder.

"Fuck," he rasped. "Much as I'd like to spend all day like this, if I don't get back out there soon, they're going to think something is wrong."

You smiled at the tone of his voice. He actually sounded rueful that he couldn't stay in here with you, which gave you some hope that maybe this could be more than a one-time thing.

"There's always next time," you teased. "Right now, I just want you to fuck me against Gregory's desk and make me scream."

He gave a strangled moan, and a second later you felt his hands leave your breasts, trail down over your sides, and hook in the sides of your underwear. He slowly pulled the panties down your legs, bending over to help you step out of them. You gasped when he rubbed his face up the back of your thigh before gently biting your left ass check. You were pretty sure you'd have a mark from that, and the thought sent a fresh rush of arousal between your thighs.

The sound of Simon's pants unzippering gave you a quick jolt of awareness, and you tried to back up, which was impossible since you were pressed between a hard desk and an even harder man.

"Condoms," you stated, your brain not quite able to form coherent sentences at the moment.

"What?" he huskily replied. Apparently, you weren't the only one who wasn't at full cognitive capacity.

"There's condoms in Gregory's desk," you urged. Much as you wanted him to just dive right on in, that would be an irresponsible move on your part.

You were grateful when Simon backed up a step, giving you room to move around the side of the desk. You quickly opened the middle drawer where Gregory kept a box of condoms. You had no clue why he had them, seeing as how it was unlikely anyone wanted to sleep with someone so distasteful. But, you had found them once while organizing his desk, so it was about time someone used them.

Grabbing one out of the box, you turned back to Simon, and promptly felt a throb of heat rush down your spine and settle on your clit. He had taken off his pants while you retrieved the condom, and now stood unabashedly naked in front of you. He had long, muscular thighs that were covered in a sprinkling of dark hair. But it was what was between those thighs that held your attention.

His cock jutted straight out from his body, long and thick and hard. He wasn't intimidatingly large, but you were probably going to feel the residual ache from taking in such a well-proportioned cock for days to come. Rounding the desk, you tore open the corner of the condom wrapper. Before you could pull it out, he reached out and plucked it from your grasp.

"Darlin', if I let you touch my dick now, this'll be all over before we've even begun."

You smirked at his words, proud to see that his eyes couldn't stop trailing over your body, couldn't stop taking in your curves. It had been way too long since you felt confident and sexy, but standing there naked in front of Simon, you felt just that.

You walked back over to the front of the desk, bending over and bracing your hands on the cool, flat surface. You slowly rolled your hips from side to side while looking back over your shoulder and purring, "Ready when you are."

He paused, almost as if he was taking you in and savoring the moment. Then, he confidently strode up behind you, his large, warm body blanketing yours. He inserted a still-booted foot between your legs and pushed your feet wider, spreading you open before him. Rough, calloused fingertips traced down your spine, causing you to shiver and gasp. His other hand curved around your hip, coasting over your stomach and through soft pubic hair to cup your mound. You whimpered when his fingers parted your sopping folds, two of the thick digits entering you slowly, as if to test your readiness.

"Shit, sweetheart, you're already soaked," he groaned, starting to pump his fingers in and out of you in a slow, unhurried rhythm.

Mewling, you arched back into him and panted, "Simon, please, fuck me…make me yours."

You felt his warm breath puff over your shoulder before he trailed his tongue up the side of your throat and whispered, "Oh, trust me, darlin'. You are most certainly mine now."

With that, he removed his fingers, positioned his cock at your entrance, and started to push inside. You whimpered at the sensation of your walls stretching as you took a man inside for the first time in way too long. Hell, you were pretty sure that you had never taken in a cock quite this big. Nails dug into smooth wood as your world dwindled down to Simon's mouth on your neck, his hands on your flesh, and his dick sinking deep inside you.

"Fuck," you breathed as he bottomed out, his balls warm against your ass.

"You ready for that one hell of an orgasm, darlin'?" he taunted, his own voice breathy and low.

"Yes! God, yes!" you begged, giving a whimper of gratitude when he pulled out of you slowly, before pushing back in.

His right hand snaked around your waist, lowering to center on your clit. You keened as his fingers started up a precise, circular rhythm that was perfectly timed to the pace of his thrusts. His left hand came down over top your own, anchoring it to the desk, the palm and fingers so large that it completely dwarfed yours. The contrast between your bodies ramped up your desire; his body large and hard where yours was small and soft. His, rough and full of sharp edges, where yours was pliant and curved.

You started to feel the coil of pleasure tighten as he continued to fuck you, both his cock and fingers moving at a rhythm that was guaranteed to make you come in record time. You bowed your head with a moan when he trailed his lips over the curve of your shoulder, his hips snapping against you sharply as he bit down on your oversensitized flesh. The fact that he would now leave behind two bite marks, as reminders of this moment and his possession, caused you to tremble and moan loudly.

You raised your head so that it was pressed back into his throat, his rough pants and deep grunts playing in your ear like a symphony. You were so close that you could almost taste it, your body ramped up to the edge of pleasure, only one small push away from flying over the edge.

He must've been able to tell, because he gave you that push in the form of his low, husky voice. "That's it, darlin'. Come all over my cock; let them all hear you scream."

As if his words facilitated the response, your orgasm smashed into you like a tidal wave. Your body dissolved into shockwaves of pleasure as you rode out the most intense orgasm of your entire life. Vision blurred and loud cries fell from your lips as you shivered and shook and came all over Simon's cock. You heard him groan loudly behind you, giving a choked, "Fuck!" as he reached his own peak.

You both stood there for a minute, panting heavily as your heart rates slowly returned to normal. Your body gave a residual shudder when he moved his left hand up over your arm and shoulder before trailing it down the left side of your torso. His other hand was rubbing soft circles on your stomach, and it was almost as if he didn't want to stop touching you. Didn't want to let you go.

But, sadly, the moment couldn't last forever, and too soon he stepped back from you. Turning, you leaned back against the desk, the two of you scanning the other's bodies, drinking each other in. He had a sheen of sweat across his chest that made your mouth water and clit twitch, as if your body was already forgetting that it just finished having an earth-shattering orgasm.

You both smiled at each other silently before reaching for your clothes. You grabbed the pink panties off the floor and pulled them on, before walking over to where he had tossed your bra onto a nearby chair. When you turned around, he was standing there with his pants pulled up but not buckled, holding out your t-shirt. You walked up to him and took it from his grasp, slowly pulling it back down over your head while he watched. You licked your lips and gazed up at him, wanting to say something, to ask if this would happen again. However, you didn't want to risk ruining the moment, so you turned to pick up your jeans, instead, while he pulled on his undershirt and button-down.

When you were both fully dressed, he gestured for you to proceed him out of the study. You opened the door and stepped out into the foyer, and it was almost as if you had completely forgotten just how many people were waiting out there. Heat flared on your cheeks at the sight of Gregory, Jesus, and every single Savior staring at you with various expressions ranging from shock to smirks. Walking back to where you had previously been standing, you glanced over at Jesus, who was looking at you bewildered, as if unsure what to think of the situation.

Simon, on the other hand, had a huge smile on his face as he walked up to Gregory and announced, "Well, I think that about concludes our visit."

Turning to his men, he ordered, "Go to the cellar and bring me all the boxes of liquor you can find. Turns out ol' Gregory here has been holding out on us."

You watched in satisfaction as Gregory sputtered and looked panicked as the group of men walked past him to carry out Simon's orders.

After the Saviors had brought up all the boxes and taken them out to load into the truck, Simon put his hand in the air, as if he had almost forgotten something important.

"Oh, one last thing, Gregory."

Walking up and putting his hand on Gregory's shoulder, Simon gave a happy grin and said, "Can I just get a kneel out of you?"

"Excuse me?" Gregory asked, seemingly confused by the request, as if he were still trying to process the fact that all his liquor was now gone.

Simon moved his face closer, grin disappearing as he stared dominatingly at Gregory and ordered, "Kneel."

You felt way more satisfaction than you were willing to admit when Gregory nodded and slowly lowered himself to the floor. And you felt a tingle of arousal go up your spine when Simon bent over so that his face was right in front of Gregory's, providing you with a spectacular view of his taut, muscular ass.

Giving a slow smile, Simon praised, "That's a solid kneel, Gregory." Patting him on the head, as if he were a loyal dog, Simon added, "You remember that for next time."

He then turned and started for the door. He caught your gaze on the way past, giving you a wink and smirk before he headed out the door. When Gregory had risen back to his feet, his gaze fixed on you, anger palpable in his silent glare. However, you found that you honestly didn't give a shit what he thought. Nothing could ruin the post-orgasmic high you were currently riding. And even better than that, you were pretty sure that it wouldn't be the last time you got to make such a pleasurable deal with Simon. You knew a lot of Gregory's secrets, from being his housekeeper, and you would gladly give them up to Simon, if it meant feeling his cock inside you again.

Smiling, you turned and walked away from Gregory, your body already tingling with excitement at the thought of Simon's next visit.