***Author's Note:For this one, I allowed a lucky follower on tumblr to pick what type of roleplay AU scenario they wanted me to write. They chose teacher Negan and a student. So keep in mind, this is AU! Although we do know that Negan was a teacher pre-apocalypse, so maybe it's not totally AU ;)***

R is for Roleplay

You walked through the halls of your old high school, a smile on your face as you took in the rows of lockers and classrooms, the last students dwindling out the doors to start their summer vacations. Today was the last day of classes, and in a few days there would be graduation. It had been eight years since you had walked these halls as a student, but not much had changed. Well, except for the fact that you were definitely older and wiser…and bolder.

It was this boldness that caused you to turn a corner and head down a particular hallway, your heels clacking on the tiles and your short, black skirt swinging back and forth as you walked. A white, button-down shirt completed the outfit, and your hair flowed freely around your shoulders. You had wanted to project a "sexy schoolgirl" persona, without it being overly obvious to anyone else you walked past. Thankfully, the halls were empty, but when you arrived at your destination, you found the door cracked open and the lights on.

There he was, sitting at his desk and grading finals, the whiteboard behind him full of numbers and equations. He had on thick, black-framed glasses that gave him a sexy, scholarly look. His once-dark beard was now sprinkled with salt, and you could see that the lines were a little longer and deeper around his eyes. But he was still sexy as hell, maybe even more so now. His hazel eyes lifted from the papers in front of him, and you saw surprise widen them when he saw you standing there. Brows furrowing in confusion, it took a few seconds before recognition lit up his face.

"Well, I'll be damned," he drawled, standing up from the desk. He was tall and muscular, just how you remembered. And his deep, raspy voice was just as arousing now as it had been eight years ago. You felt a shiver go down your spine when his eyes scanned quickly up and down your body as you stepped further into the room.

"Hey, Mr. Negan," you said with a tentative smile.

He came around the desk and leaned against its front, reaching up to pull the glasses slowly off his face and lay them on the desk. You stopped a few feet in front of him, hand on cocked hip and legs crossed in a demure yet, you hoped, sexy pose. He asked how you had been, and you satisfied his curiosity by chatting with him about college, what you had studied, and what you were doing now. You discussed how you were back in town to watch your sister graduate high school, and thought that you would stop by tonight, to see if your favorite teacher was still here.

He smirked at this, taunting, "Oh, come on. Favorite teacher? As I clearly recall, math was not your best subject."

A grin curled your lips at the fact that he remembered just how much you had struggled through his class. Licking your lips slowly, you teased, "Well, it's not because I wasn't any good at it. More so that I was always getting…distracted."

"Distracted?" he questioned, arching a brow in curiosity. "By what?"

Twirling a strand of hair around your finger, you looked at him innocently, and said, "Why, by you, of course."

He stared at you silently for a few seconds before saying, "Me? How the fuck was I a distraction?"

You almost laughed at his response. Even when you had been a student, he had always had a filthy mouth. It didn't matter how many parents called in complaining, Mr. Negan didn't give a fuckity fuck. He had made it clear that if his students couldn't handle his foul language, then that was too fucking bad. You had loved it then, and you loved it even more now.

Deciding to lay your cards out on the table, you took a deep breath and honestly replied, "You were a distraction, because I spent more class time fantasizing about you, than I did listening to your lectures."

He stared at you in stunned silence, and you gave a mental fist pump that you had been able to well and truly shock him with your response. He had always been such a cocky mother fucker, and while you had played the role of the quiet, good little girl when you were his student, it was time to let your naughty side shine. Worst case scenario: he told you to get the fuck out of his classroom, you stayed in town for graduation, and then were gone again in a few days, no big loss. But the best case scenario…well, it was obvious what that would be. It was a long shot that he would reciprocate your feelings, but 'teenage you' would never let you live it down if you didn't at least attempt to make this almost decade-long fantasy a reality.

Mr. Negan cleared his throat and ran his tongue over the seam of his lips. You watched, mesmerized, wanting nothing more than to feel that tongue on your flesh.

"And what, exactly, did you fantasize about?"

You were almost afraid you had imagined his response, that your over eager brain had constructed the words as a hallucination. But one glance at the smirk on his lips and the heated intensity of his gaze confirmed that he had actually spoken the words out loud. That the best case scenario might actually happen after all.

"Well," you purred, walking up closer to him, so that your skirt brushed against his leg when you walked by. "I did fantasize about this desk quite often. Of you bending me over it and giving me a good spanking. Or spreading me out on top of it, while you sat in your chair and ate my pussy."

You trailed your fingers over the wood as you walked around the side of the desk, Mr. Negan's eyes following your every move. "But, I think my favorite fantasy, was this." You stopped in front of the whiteboard and tapped a nail against it. "Yea…imagining you pushing me up against this, flipping up my skirt, and fucking my brains out was definitely what got me off the fastest."

You were beyond shocked and proud of yourself for being so blunt and honest. Your inner teenager was giving a round of applause and nodding in awe. When Mr. Negan pushed off the desk and started walking to the door, you felt your stomach drop at the notion that he might be leaving. Perhaps you had been too blunt…

But then you watched as he closed the classroom door, drew the blind over the small window, and turned the lock. Arousal flooded between your thighs when he turned around, his gaze burning a trail from the top of your head down to your toes, before trailing back up again. He prowled across the classroom towards you, as if a panther stalking its prey, and you almost forgot how to breath.

He stopped right in front of you, looming over you in a reminder of how much taller and broader he was…how much stronger. The thought made your thighs clench. He made sure to enunciate his words clearly when he asked, "Just to clarify, are you fucking sure that this is what you fucking want?"

You gave a whimper and a nod before gasping, "God, yes!"

With that, he grabbed your arm and spun you away from him with a growl. He pushed you roughly up against the whiteboard, the smooth surface cool against your cheek, and the metal bar that held the markers and erasers digging deliciously into your stomach. You let out a shaky moan when you felt a big, rough hand trail up the back of your thigh, lifting the edge of your skirt to expose your bare ass.

"Well well well, what the fuck do we have here," he purred, running his hand over the soft globes. "No panties? What a naughty girl."

Trying your best to keep up with him, to meet his sass with your own, you hoarsely replied, "Are you going to fuck me, or are you going to stare at my ass all evening?"

You let out a sharp cry when his palm came down, fast and hard, on your right cheek, the slap echoing around the empty space. "There will be no back talking in my fucking classroom, is that understood? Otherwise I will pull out my ruler and show you how naughty girls get punished."

You almost collapsed to the ground in a puddle of drool at his words. God, his voice growling those words was almost more than you could handle. No one should have a voice that panty-droppingly sexy, let alone have it attached to those eyes and that mouth.

"Now, are you going to be a good little girl for me, or do I have to punish you?"

You moaned at the images his words conjured. While part of you was intrigued with what kind of punishment he might have in mind, a larger part of you didn't want to play any games. Your pussy had been begging for his cock for almost a decade, and you were so close to fulfilling that goal that you didn't want to wait one minute more than necessary. Wiggling your ass back into his crotch, moaning at the feel of his hard dick through his pants, you begged, "Please, sir. I promise to be good. Please, fuck me."

He chuckled in response, causing goosebumps to raise on your flesh. You heard the sound of a zipper, but when you tried to turn around and look, he pushed you harder into the whiteboard, one hand coming up to grab a fistful of your hair and pin your face to the smooth surface. He inserted a foot between your legs and kicked your feet further apart, spreading you out in front of him. You gave a hoarse cry when rough fingers slid between your legs from behind, rubbing along your slit as he growled, "Fucking hell, you're already soaked."

Trying to arch your back, but plastered between the whiteboard and his hard body, you gasped, "All for you…it's all for you."

He gave a strangled moan, and his fingers disappeared, to be replaced a second later with his cock. You mouth dropped open as he breached your opening. Jesus fuck, but he was big! You whined and tried to spread your legs further as he stretched your walls to their limit. Never in your life had you taken in a cock this big, and when he finally buried himself to the hilt, you felt so full, so stuffed, that you didn't know where you ended and he began.

"Christ, you're so fucking tight, sweetheart," he groaned, leaning forward and nipping at the back of your neck with his teeth.

You only moaned in response, unable to form a coherent sentence if your life depended on it. All that currently mattered in this world was Mr. Negan's cock in your cunt and his voice in your ear. When he slid his other hand around to grab your breast through the thin shirt, you shivered and felt your walls contract on his cock.

And then he started moving.

He didn't start out slow and gentle, or warm you up to a faster rhythm. He immediately set up a quick and brutal pace…and you loved it. You cried out with every thrust, his cock slamming into you and pushing you up harder against the whiteboard. The metal bar at your stomach pressed into your flesh in a way that would've been painful, if you had enough brain cells to care.

Between the feel of Mr. Negan's big, hard dick driving into you, and the grunts and growls that were a constant litany from his lips, it wasn't long before you felt your orgasm start to build. It coiled inside you tighter and tighter, the pressure becoming almost unbearable. And yet, at the same time, you never wanted it to end. When the hand in your hair tightened sharply and the hand at your breast lowered to your clit, you whimpered at the mixed sensations of pain and pleasure. His masterful fingers started to work your clit at an expert pace, and you were pretty sure you were whining and panting and begging him incoherently at this point, but all that mattered was that he not stop. When he tightened the hand in your hair yet again, jerking your head back and sinking his teeth into the soft flesh of your shoulder with a growl, you went up and over the edge. A scream left your lips as your pussy contracted around his cock, shudders wracking your body as the orgasm rolled through you. If it wasn't for Mr. Negan's hands and cock holding you up, you would've slid to the floor in a shuddering, heaving pile.

Right when you were coming down off your orgasm, you felt him reach his own peak. He groaned and gave a few quick, jerky thrusts into you as the pleasure overtook him. You gasped at the feel of his hot cum spurting deep inside you, his hoarse moans in your ear. The two of you stayed locked like that for a few long moments, his dick twitching inside you while you both tried to catch your breath and slow your heart-rates down to a normal pace.

When he slowly pulled out his cock, you gave an involuntary whimper of disappointment. He backed up a step, finally allowing you to turn around. You watched as he tucked his dick back into his pants and pulled up the zipper. Your skirt had automatically fallen back into place, and just like that, the two of you were once again presentable. Well, presentable if no one noticed the way your hair was tangled around your face, the red bite mark on your shoulder, or the streak of cum that was slowly rolling down your inner thigh.

Taking a deep breath and reaching up to run his fingers slowly over his beard, he looked you up and down slowly, before his eyes captured yours and a slow smirk crossed his lips.

"Well, was it as good as you fucking imagined?"

Mirroring his smirk with one of your own, you gave a light laugh and forced shaky legs into motion. It wasn't until you made it to the door, unlocked it, and were about to leave the room, that you turned around and bit your lip seductively before purring, "It was even better than I imagined. In fact, I think that's the best god damn lesson you ever did give me."

With that, you walked out of the classroom and started down the hall. When you made it home, your sister asked why you had red streaks on your cheek. Confused, you looked in the mirror, then burst into a fit of laughter. It was from one of the math equations written on Mr. Negan's whiteboard; the marker had smeared onto your cheek when you were pressed against it. He had to have seen it, but the cheeky bastard hadn't said a word, instead letting you drive home with his physical mark on your shoulder and his educational mark on your face.

But that was okay, because you knew he would be at graduation in a few days, and that between now and then he would be at the school, grading papers. That gave you plenty of time to pay him another visit, to let him teach you another lesson. And next time, you'd make sure that he was the one who was left marked by you.