A/N: Ughhhhhh this chapter took way too long to write, and I am tired. I am not entirely happy with it, but no matter how hard I tried I could never bring myself to be happy with it lol I hope you guys enjoy it well enough

The only sound that rang through the halls of the Sanctuary were your own nervous footsteps, each one taking you closer and closer to the very room you were requested in earlier. It took hours for you to finally psyche yourself up, and come up here to the higher levels where Negan and his wives took refuge. You weren't sure if you should honor that request, but once his sheets had dried on the clothesline you decided to do as he said. He only kissed you, it wasn't a big deal you tried to tell yourself, but in all honesty your legs were already shaking. You had no idea what to expect, but if his heated kiss had anything to do with this little visit…you were freaking out already thinking about it.

You stood just outside his bedroom door, the polished wood of it shining in the light. With a deep breath you brought a hand up, stopping inches from it before knocking. And all at once you couldn't do this, you decided. This was crazy; you can't just come up to his room and return his bed sheets. What if he wanted more? What if he figured out you weren't exactly seasoned in these ventures? It was all too embarrassing to think about, so you swiftly took off down the hall electing to give the basket of materials to another girl to bring up because nope, you were not going through with this.

It was only a few feet down the hall when you bumped into someone, knocking you back onto your butt and the basket falling out of your hands.

"Well, I'll be damned."

That voice, that oh so seductively charming voice. You knew it like the back of your hand, and with a pink hue on your cheeks you reluctantly looked up to meet the dark gaze of your boss. "I'm so sorry!"

A chuckle was all he returned with; watching as you frantically gathered his sheets and placed them back into the laundry basket.

"Did you come all the way up here for little ol' me, sweetheart? Well, I am fucking touched."

His hand comes down to assist you, and you take it in yours allowing him to help you up. You clutch the basket closely to your chest; eyes down turned already feeling a bit anxious around him. Negan just grins at your show of shyness, and with the most charming of gestures he turns your hand in his own, lips placing a soft kiss to the back of your hand that made you instantly go weak in the knees. It was hardly fair the man held such power over you.

"Follow me, darlin'."

With shaky legs you manage to follow him back down the hall and towards his room, and you can feel every nerve begin to set fire, every synapse setting off with each step closer you got. And then there was Negan, completely unaffected by the whole situation, all he did was saunter into his room, grabbing a beer from a nearby ice chest and plopping down onto his fancy couches leaving you to stand in the middle of the room awkwardly awaiting his command.

He takes a sip of his beer, casually gesturing towards his bed before swallowing. "I'd very much appreciate it if you fixed up my bed for me, darlin'. If it's not too much to ask."

You glanced over to his bare bed, nodding obediently and setting the basket down as you began to unfold the dry sheets. Before all this, you had never seen his room and it only made sense for him to have the very best one but even so you weren't expecting all this. His bed alone made you envious, the one you had was very basic and there wasn't a day you didn't wake up with sore muscles. While you admired his many luxuries, you weren't aware of the set of eyes that lingered on you, following your every movement. Enjoying the sight of you bending over here and there to properly place his sheets on the bed, your soft hands would glide over the satiny material attempting to smooth out every single wrinkle. The crush of a can caught your attention, but you elected to ignore it and instead focused on your task, it did help settle your nerves after all.

"There's no need for that, sweetheart. Sure as shit gonna be wrinkling them back up soon enough."

Your heart began to beat wildly behind your chest, his innuendo not lost on you. You could hear the sound of his boots touching the ground, bringing him closer to you until he was at your back. All you could do was turn, and look up at him standing there like a blushing idiot.

"Yes, sir."

Negan could tell you were tense, and it only brought that smirk back to his lips. You were far too easy to mess with, and he enjoyed every second of it. His hands came up to your shoulders, rubbing them softly as he calmed you.

"Easy there, baby. No need to be scared of me."

"I know…"

Quite the contrary actually, you weren't scared of him, you were just losing your mind. He was so close to you, it was beyond tempting to reach out and touch him, almost like you needed to make sure this was all real. So many of your fantasies about him started here, in this very room you had only dreamt about. The gravity of this situation was enough to make you lose your breath.

His hands ran down your arms, and you realized then that you were slowly being backed up against the bed, your hips hitting the soft edge. He had you right where he wanted you.

"Then why deny yourself the damn pleasure, baby."

The way his little pet name for you rolled off his tongue made you shiver. It was so deep and so sensual; it almost conveyed all the dirty things he wanted to do to you. But, damn was he ever intimidating to you. You wanted to kiss him, you wanted to touch him in ways you've never touched another man before, but how? How exactly do you work up the nerve to do all that to someone like him? For heaven's sake, Negan was the type of man that could make a woman's panties drop with just his voice. And you were nowhere on that level. More so, would he even want someone totally inexperienced in this regard? He had a harem of women to choose from, so why come to you?

"Negan I-"

You couldn't bring yourself to say it; you were at an emotional crossroads right now. Tell him you want him, and he'd take you and probably be disappointed with your lack of knowledge. But say no, and suddenly you'd live with the regret of not having been with him in the most intimate and dreamt about ways.

Negan only grinned down at you, his body getting even closer until his leather jacket is pressed firmly against your chest, making you squirm in his hold. The things he made your body feel, it was all so new and so enticing. The arousal alone was shooting in waves over you causing bumps to rise on your skin and your nipples to harden into peaks that only grew more sensitive as the smooth leather brushed across the thin material of your shirt.

"You what, baby?"

His lips had descended down to your jaw, teeth nipping delightfully at your skin as he glided his hand down to your waist gripping the curve of your body tightly, holding you in place. Desperately, you tried to spit out the words but his administrations on your body was far too distracting. But, it was his words that made you whimper out, his hot tongue coming to lick a path from your jaw up to your ear as he whispered dirty promises to you. In your hazy state you vaguely caught mention of how he was just dying to be inside your tight little pussy, drawing out every single one of his vivid fantasies. If you weren't a puddle of desire before, you certainly were now. Your hands came up to grip at his shoulders, trying to steady yourself as he continued to nibble at your ear. There was no denying what a mess you were down there, you could feel your clit swollen with need, building a pressure down there that made it almost unbearable to deal with. By this point you were sure your panties were soaked with your own juices. All these feelings were new to you, and you weren't sure your own body knew how to react at first. It was overwhelming, and every part of you even if you willed it or not just screamed that you wanted this man.

"I…I…" Your words came out weak and breathless, and a moan slipped past your parted mouth as Negan sucked a mark into your neck, claiming you as his own little mistress. He chuckled when you pushed your hips forward, attempting to make more contact with him, and he obliged generously to your request as he thrust his hips forward and into yours making you gasp when you felt a very prominent bulge push into your stomach.

You realized a little too late what was going on, a sudden wave of panic hitting you as it dawned on you that you were with your boss, in his room, legs spread apart as he leaned you further and further into his bed. It took all your willpower to press your hands to his chest, getting him to stop all his actions as you blushed deeply and glanced up at him in shock. His hands were still on your waist, thumbs gently brushing over your shirt while that grin came back to his face.

"I can see this is hard for you, darlin'. If you're agreeable, I can-" He dipped his head down, bringing his lips to your ear as he whispered the rest of his daring words. "Make it even harder for you." And with that he pressed his throbbing member against you, a groan coming from him as the friction became a bit much to handle.

You squeezed out of his grasp, face turning a bright shade of red. The feeling of his most private of areas pushing into you only caused the heat to grow inside, and you weren't sure you could handle all of this. With a jump, you crawled back into his bed, fingers mixing into the satin of his sheets. This only served to fuel his desire for you, in his eyes you looked absolutely heavenly splayed out on his bed like that, shirt slipping off your shoulder, face a beautiful shade of pink, and your hair a tangled mess. All that was missing in his eyes, was him on top of you. But, that was a problem he could easily remedy.

Negan kicked his boots off, slipped out of his jacket, and slowly began crawling towards you. Much like a predator chasing his prey, he had you cornered in his territory now. Your attempts at an escape only caused him to laugh, making that smug look return to his features like he knew exactly what you wanted to say, but it would only cause him more pleasure to hear you utter it aloud. And you did.

"I'm a virgin!"

Negan stopped above you, his hands on either side of your shoulders as he gazed down at you. His lips curled into a smirk, eyebrows rising as he let out a very amused laugh.

"Well no fucking shit, sweetheart."

To be fair, you had to realize how much of your behavior gave it away. You saw him around his wives, they kissed or touched him with such confidence you had to envy them even a little, and then there was you. A blushing mad looking fool who could barely get a word out around him.

"Of course you knew…" You sighed, holding your hands over your face to hide the deep embarrassment and shame you were feeling right now. Negan, however, didn't seem to care in the least. He shifted his weight until he was lying next to you, his hands coming up to grab your wrists and pull them away exposing your face in all its shy glory.

"Re-fucking-lax, sweetheart."

It was more than surprising to you that he hadn't already turned you away, knowing he could run to any one of his wives to please him in ways you probably couldn't.

"You still want me?"

He cocked an eyebrow up in disbelief at your assumption, and he looked down at his own arousal. "The fuck do you think?"

A laugh left your lips, and he was grinning at you now trying his best to calm you down, even though he clearly wanted this to move forward.

"Just sit back, and enjoy the fucking ride. I promise I'll be gentle, unless you want otherwise."

Negan came to rest on top of you again, his lips inches from your own as he slowly dragged one of his hands down your side, slipping his fingers under your shorts and pulling them down in one swift movement. It was nerve wracking to be laid out in front of him like this, but every time he caressed your side it erased all those feelings of anxiety. He was surprisingly caring for a man who could place an iron to a man's face, and if you were going to lose your virginity to someone you were happy it was him.

He captured your lips in a fevered kiss, tongue dipping out to trace the outline of yours, demanding entrance into your mouth which you so kindly offered. His hands were spreading your thighs apart, hips fitting perfectly against yours as he rocked into you making you moan into him. Every touch, every kiss he placed on you was only building the pressure between your legs, and deep down you began to ache for something more, something bigger to fill that desire. Your hands came up to the hem of his shirt, gripping it softly wondering if it would be ok to touch him like he was you, and when he leaned into your fingertips you took that as your green light. With trembling hands, you tugged on his shirt lifting it over his torso and up to his arms until he dared to pull away from you long enough to remove it.

When he was discarded of the garment he went back to your lips, biting gently down on the lower one until he had you squirming beneath him. You bucked your hips up, wanting to feel the heaviness of his growing erection pushing into you again. But, his hands came to your hips, shoving you back down and releasing your lips from his earth shattering kiss.

"Dirty girl, already begging for me to fuck your brains out."

A blush crept to your cheeks at his bluntness, but you only answered him by grabbing at the waistband of his jeans, pulling him forward enough until you could unbuckle his belt. He didn't stop you this time, he seemed too amused at your sudden burst of confidence. And he watched eagerly as you shakily removed the item from him, sliding it through the loops and onto the ground. Negan's eyes never left you, he only stared with desire and mild amusement when you unclasped the button of his jeans, and taking the zipper between your fingers as you edged it down. You had no idea what you were doing, or what you even planned to do once he was free of his confinements all you knew was that you had to have him.

It probably took longer than it should have by the time you worked up the nerve to remove his boxers, and truthfully he had to help you with that. But, he hardly seemed to mind, he even looked rather proud when he finally freed his aching cock. You had never seen one up close before, but all you could think about was all those adult films you had watched back in college in your 'spare' time, and how the women used to please the men with their mouths. You had to wonder if that took any sort of skill, but thinking about that only made you more nervous to try it on him.

"Like what you see, doll?"

His voice cut through your thoughts, and you realized you had been staring at his length for quite a while by now. And judging by the huge smirk plastered on his face, he didn't mind one bit.

"I was just…do you want me to, you know?"

Negan caught on quickly to what you were referring to, and with a chuckle he winked down at your confused face, and got off the bed and looped his arms under your thighs, pulling roughly so your hips could be level with the edge of the mattress.

"Allow me the fucking honors, baby."

Negan bent down, his eyes dancing up to meet your own as he took the hem of your panties between his teeth, still grinning up at you as he pulled them slowly down your soft thighs. The action itself was enough to make you wet, and when he finally pulled them off of you and spread your legs he was pleasantly greeted with the view of your soaking wet pussy.

"Holy crap…" He licked at his lips, gaze turning darker as he drop to his knees before you, more than ready to bury his face into that awaiting heat that burned just for him. You had never been this exposed or vulnerable before, but with him it somehow came a bit natural, and you found yourself spreading your thighs even more as he closed in on your sex. With a single flick of his tongue against your swollen clit, you were already arching off the bed, whining out his name to give you more. And he happily relented to your pleading. His warm tongue slid between your glistening folds, a groan leaving his lips as your taste fell to him. You were everything he expected and more, and the way your hands shot down to grip his hands was making him ache with pleasure.

"Negaannn…" His name wasn't meant to sound so whiny coming from you, but god was his tongue working wonders. It's like he knew exactly how to lick and lap at you, and the way his mouth clasped around your clit was enough to bring you close to the proverbial edge. Your lower back lifted from the bed, mouth hanging open in a silent scream as he lapped hungrily at you, it was like he couldn't get enough and his fingers were digging harshly into your hip bones keeping you in place.

"Fuck you taste like goddamn heaven, doll."

A moan escaped you, and you felt your orgasm approaching at a fast pace, in your pleasured state you had crushed your thighs together, trapping Negan between your legs until you finished riding out your ecstasy. Of all the times you had brought yourself to the brink, this was by far the most intense one you've ever had, courtesy of the man currently lapping up the remnants of your orgasm. Negan slid his hands up your legs, fingers finding the buttons of your shirt and undoing them one by one until he had it completely open, exposing your tempting chest to him. He took your breasts in each hand, massaging them softly as he planted a trail of hot kisses up your stomach, enjoying the way your muscles quivered under his touch.

You were a sweaty mess by the time he was done with you, and when he finally reached your lips he was laughing, clearly entertained by the exhaustion you already felt.

"I'm not anywhere near done with you, darlin'."

With a small whimper, you threw your arms over his neck, bringing him down for a kiss. The taste of you was still lingering on his lips, and it made you blush deeply, this was by far the dirtiest thing you've ever done, and the intimacy of it all was absolutely wonderful to you. He pulled away after a moment, his hands grabbing yours as he laced your fingers together. His knee pushed your legs apart once more, hips shifting between yours until you could feel his hot length pressing between your folds. He kissed at your sweaty forehead, brushing aside some wet strands of hair as he settled himself at your entrance. You had heard stories of this hurting, and apprehension was coming over you but the need to feel him inside was far more overwhelming at the moment.

"Please…"

It was all he needed to hear, and he gripped at his cock, pushing the head of it into your warmth stretching your inner walls until they fully accommodated him. A growl came from deep in his throat, the heat of you enveloping him almost driving him to the end already, but he stilled inside of you not wanting to cause you any unnecessary pain.

"Shit, baby." He rasped out, and it took everything in his power not to thrust forward harshly. He wanted nothing more than to take you hard and fast, making you cry out until you lost your voice, but he denied himself the pleasure of that experience, and instead withdrew from you slowly allowing your body to get used to the feeling. You pawed at his shoulders, nails digging into his skin as he buried himself back inside of you in an unbearably slow pace. It hurt, but not as badly as you had thought it would. It was a mild burning sensation that lingered, but with every snap of his hips it began to fade into rippling streams of bliss.

You wrapped your legs around his waist, the sweat that formed on his body causing your thighs to slide effortlessly against him. His hand grabbed at your thigh, using it as leverage as he quickened his pace. The sound of skin slapping against skin filled his elegant room, accompanied by the gasps and pants that fell from your lips with every thrust he made. He pushed your leg down, flattening it against the mattress as he pulled his hips down harder, eyes transfixed on your chest as it bounced up and down with his movements. Even though you had cum earlier, your clit was still sensitive, and with every push of his hips his abdomen would brush dangerously close to it, causing you to twitch in both pleasure and pain. It was too much to handle, and the sensations were enough to make you want to cry out, but you bit at your lip, fighting back the urge and instead ran your fingers up his arms, taking in the way his muscles clenched and worked at setting the rhythm. But, he was close and judging by the way his hips began to falter it would be coming anytime now.

Negan nuzzled into your neck, trying to muffle his own groans of pleasure as his climax hit him, and he bit down onto the soft skin, soothing the wound with his tongue as he pulled out of you, spreading his seed all over your taut stomach. He stayed above you for a minute, catching his breath while you did the same, and with a spent sigh he fell beside you, his arm coming to curl around your waist and pulling you closer.

"Fuck…you are never leaving this bed, sweetheart. You understand?"

You laughed at his words, a smile resting on your features as you snuggled next to him. His arm tightened around you, keeping you possessively close to him as if you'd run off in a heartbeat. But, you had no plans of leaving his side anytime soon.