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Man for Hire

Summary: Eager to lose your virginity, you hire Negan who is a male escort to help you with your problem.

Characters: Negan & the reader (OC, second person)

AO3 Link: https://archiveofourown.org/works/55642924

Warnings: 18+, Swearing, Smut, Little To No Plot, Daddy Kink, Unprotected P in V, Oral, No Use of Y/N, etc.

Notes: This is the first thing I've been able to write in a long time because school and work have been taking up most of time. This is really just a filthy one shot. I almost considered making this a short story for a while, but then decided to go with a one shot because...why not? (gif credit: @jdmorganz)

What the fuck were you doing here? That was really the question. The silence was eating away at you. Your heart was hammering inside of your chest and you were nervous. You’d never done something like this before. And you were starting to second guess your decision in making such a bold move.

Looking to the time, you felt the lump in your throat growing and your nerves heightened once you saw how close to the time you were waiting for actually was. This was so outside of your comfort zone. Spending money on something like this just didn’t seem logical in the end. Here you were sitting in the middle of an expensive suite at a very nice hotel in the middle of the city. The sights were beautiful and you were enjoying yourself, but the reason you were here is what had you so nervous.

Truth was? You were meeting someone. Well, kind of. You were paying someone to meet you here. Which was complicated in itself. If people were to find out that you were doing this, it would be hard to explain. At the end of the day, it was something that your best friend had convinced you would be good for you. You were in your early twenties and you were still a virgin. It wasn’t something that you originally felt bad about, but it always made things complicated when you went to date someone. There was always that stigma there of being a virgin. And you were never really comfortable enough to tell someone you were dating that you were one. There was also no one you ever felt comfortable enough with to actually have them take it. Sure, you’d fooled around with a few people, but you never actually followed through with all of it. You were just always so busy working and going to school that you never felt the need for sex. Now that you were older, well, it felt awkward being the only virgin that you knew. It was an embarrassing thing, so the only person who really knew at the time was your best friend. Who convinced you it would be for the best if you hired a professional to help you out with your ‘problem’. That way there was no judgement, it would be done by someone who should know what they were doing and you could hand pick who you wanted it to be. You wouldn’t have to worry about the dating process, you could just have sex and that would be that.

It's just the closer you got to everything, the more pathetic you felt. Your friend had found a couple of sites for you that you looked at together. Then you found one that you felt comfortable with and connected with the woman in charge. The woman was very personable, but straight to business. She sent you a list of men that would be available for you. She had asked you for some details and you were honest with her as to why you were doing this. There was no reason not to be.

After taking some time to look through your choices, you came to a profile that you ended up being immediately enchanted with. Negan. There were a lot of younger, muscular men that they were trying to sell, but you had always been attracted to men older than you. But from the first photo you were immediately drawn to the chiseled jawline of the man sitting on a motorcycle. He was wearing a leather jacket that was opened to reveal a gray Henley that laid underneath. A pair of worn-down leather jeans and black sunglasses. From the confident smile to his salt and pepper colored beard you were hooked instantly. Every photo you saw only drew you further in. In other photos his incredible dimples and gorgeous hazel eyes made you more confident that this would be your choice. Even the tattoos that covered his body made him more attractive to you. This was a man that would have caught your attention immediately if you saw him on the street. To say you were attracted to him would be an understatement.

After looking through the rest of the profiles that you were sent, you returned back to the woman that was in charge with the name that you wanted. At first, she tried to convince you to go with someone else. Even though she admitted Negan was one of their most popular escorts, she tried to give you other suggestions of who she thought would be better for your certain situation. A lot of them were the younger ‘cuter’ boys, but cute wasn’t exactly what you wanted. Once she realized that she wouldn’t be able to convince you otherwise, she agreed and set up this meeting. Negan was more expensive and the prices varied by the amount of time you wanted. Two hours, four hours or the overnight rate. You really thought two hours would be plenty enough, but your friend convinced you to get the whole night. You didn’t know why. You were just going to have sex with this guy and be over with it. Having him there with you afterwards would only make things awkward. You couldn’t change your mind now though. You already paid.

A knock on the door to your hotel room pulled you from your thoughts. It jumpstarted your heart in your chest and you felt incredibly nervous now. Standing up from where you were seated, you adjusted the material of the tight fitting black dress that you were wearing. Making your way over to the door, you nervously outstretched your hand to turn the doorknob and felt the breath leave your lungs when you pulled it open. Leaning against the doorframe stood the man from the profile, his hazel eyes looking over you curiously. A charming smirk tugged at his lips while he gazed over you. What he was wearing actually surprised you. It was a bit different from the photos in his profile, but you didn’t hate it. He was well groomed, his body donned in a very expensive looking black suit that was only buttoned in the middle drawing your eyes to the white button down that was underneath. The first few buttons of his shirt were undone revealing the thick curls of hair over the center of his naked chest.

You were so distracted taking all of him in, that you missed when he said your name. Speaking louder, the tone of his deep, raspy voice sent chills down your spine. In his right hand, he had a single red rose and outstretched his hand to you when he finally got your eyes to lock with his.

“Can I come in?” he questioned, his nose wrinkling in amusement when he realized you must have been gawking at him. God, you must have looked like a fool just standing there in the doorway staring. Pushing the door open, you allowed him into the suite and accepted the rose when he stepped before you.

“Thank you. This is very sweet,” you commented on the gesture knowing that you were expecting a much different scenario than this one. Closing the door behind you, you noticed that he was standing rather close to you and it made a breath catch in your throat. Fuck. That’s when you noticed the smell of his cologne. It smelled amazing and only made him even more attractive. How was that even possible? Stepping forward, his hazel eyes stared down at you and it made you feel incredibly hot with how close he was.

Lowering down, the warmth of his breath lingered over your lips before he pressed a kiss over the side of your face. It drew your eyes to close, your lips parting when the kiss lingered and when they opened again, you could see him pulling back with a big smile over his face. The dimples were even sexier in person. Suddenly, you weren’t regretting your decision so much.

“You look gorgeous,” he started off, immediately complimenting you nodding toward the dress that you were wearing. “That dress looks really nice on you.”

“And look at you,” you waved your hand about pointing toward what he was wearing. “You look really sharp. I wasn’t expecting this whole getup with you showing up today.”

“Oh? This old thing,” Negan smirked, unhooking the button of the suit jacket before pushing his hands into his pockets and shrugging his shoulders. “Let’s just say the woman in charge thought it would be a nice touch considering everything.”

“Oh, so you know?” you paused realizing that of course he knew that you were a virgin. He would have to know since that’s why you were doing this whole thing to begin with. “You probably think I’m a loser.”

“Why would I think that?” his eyebrows furrowed, a muscle in his jaw flexing when he tipped his head to the side. “Every person’s situation is different. Who the fuck am I to judge? That’s not my job to judge.”

“And what is your job exactly?” you spoke quietly and he snickered. God that was stupid. “I mean, I know you’re an escort. I just, should I call you Negan? I don’t even know if that is your real name. It’s probably not, right?”

“No, that’s my real name,” he admitted with a bob of his head, dragging his tongue across his bottom lip in a confident sweep. “I probably should use a fake name considering the job, but I like being authentically me. And to answer your question, my job is different for everyone. It’s my job to find out what someone needs so I can give it to them.”

“Smooth,” you outstretched your hand to his which he accepted and followed you over to the couch. First, he helped you sit before taking a seat next to you. A chill flooded through your veins. You understood why Negan was one of their most popular escorts. He was in here a few minutes and you were already ready to jump him. Setting the rose down on the coffee table before you, you turned toward him and felt bold in the moment. “I don’t know what we’re supposed to do here Negan. I’ve never done something like this before. Obviously.”

“What do you want to do? You have me for the whole night,” he reminded you, outstretching his hand to push a piece of hair out of your face. Sweeping his thumb in over your jawline had you leaning into the warmth of him with your eyes fluttering to a close. “Did you want to go out for a night out on the town? Do you just want to hang out? Or…we can just jump right into things.”

“You mean sex?” you blurt out probably too fast which had him smirking and bobbing his head.

“That is what I mean, yes,” Negan’s deep voice rumbled with him sliding in closer to you. His arm hooked around the back of you with the warmth of his breath hovering over your bare shoulder. Suddenly the smell of his cologne filtered through your lungs. Desire overtook you and you had to keep yourself from throwing yourself at him right then and there. A minty scent also fell from his lips from a gum that he undoubtedly had been chewing on before he had showed up. “It’s all up to you what you want. What your fantasy is.”

As he spoke, Negan’s head lowered closer to the crook of your neck. Nuzzling his nose in against your flesh had you sucking in a sharp breath of air which was followed by him depositing a faint kiss over your neck.

“I can’t believe I’m going to say this, but do you think we can talk first?” you wondered standing up from the couch which seemed to surprise Negan a bit, but he nodded as you headed over toward the bottles of alcohol that were in the corner of the room. You should have just jumped him right then and there, but your nerves were getting the best of you. “Do you want some bourbon?”

“I’m more of a gin guy,” he responded, standing up from the couch when you looked through the bottles and pulled something out that you thought he would like. “Is everything okay?”

“You want me to be honest?” you spoke faintly while you poured both him and you a drink hoping that it would help settle your nerves. With a nod of his head, Negan smirked and stood by the window to look down at the city beneath you. The bright colors were reflecting on the walls and he seemed to be in awe of the lights. Stepping in beside him, you held out the drink you got for him which he accepted, with his fingers brushing up against yours. “I’m starting to regret doing this.”

“Am I not what you expected?” suddenly he seemed almost offended, clutching the glass tightly in his hands when he turned to look at you. “I told Michonne that I should have just warn what I usually do because…”

“No, you’re perfect,” you immediately interrupted him, placing your hand over the center of his chest to get him to focus on you. “God, you are fucking gorgeous. And that’s the thing. You are this beautiful man and I’m a virgin that you are going to have sex with. I’m probably going to be awful and…”

“Oh,” an amused chuckle fell from Negan’s lips when he took a sip of the drink, his free hand placing in over yours to give it a firm squeeze. Swallowing down the sip, he looked to you and shook his head. “You don’t have to worry about that. Please don’t. It’s not something to worry about. People who have sex all the time sometimes aren’t even that good. Plus, my job is to make everything perfect for you. Whether we have sex or not. Don’t let the expectations of sex distract you and make you nervous. I’m a very chill fucking guy. You’ll walk away with a good experience by the morning, I promise you that.”

“Cocky,” you smirked, throwing back your drink in hopes it would give you some liquid courage. “I like it.”

“I just know I’m good at my job,” Negan assured you with a wink, finishing off his drink and setting the glass down, taking yours as well. Urging you back to the couch, he sat you down and took your hands in his when he lowered beside you. “I get the feeling you’d like us to get more comfortable with one another, so we will just talk for a while if that’s what you want. Or we can go out.”

“We can talk,” you were impressed with the way he was attempting to calm you down with the rough pad of his thumbs sweeping over the back of your hands. “Michonne tells me that you are one of her top escorts.”

“I told you, I’m good at my job,” Negan winked, his dimples becoming more prominent when he smiled and it took your breath away.

“So you must be really good at sex?” you suggested and it made him smirk again. You probably sounded really stupid right now, but you were curious.

“That and I’m the best at making people feel good. Not everyone that wants to have an escort wants sex. They want to feel special. They want to feel like the center of the universe and I’m good at that. I excel at reading people,” he explained, curling his finger underneath your chin to get you to tip your head back to look at him. With his eyes hooked on yours, you felt exactly the way that he described. Like the center of the world. “Some people are just looking for companionship. And I’m able to give that to them.”

“Fuck,” you exhaled with how close he was to you. Personal space wasn’t something that existed with Negan, but he was right. He was good at his job. “You know, Michonne tried to persuade me to get someone else instead of you. I’m curious as to why.”

“Well, she’s not exactly my biggest fan. Her husband and I have never really been able to get along,” he expressed with a wicked smirk, shrugging his shoulders when he spoke. “When people look at me, they assume that I wouldn’t be a good choice to take someone’s virginity.”

“She wanted me to pick someone like Siddiq,” you explained and Negan scoffed at your response. It felt like he was getting closer to you if that was even possible. “Thing is, I don’t want boyishly cute men.”

“Of course you don’t and you made a good choice,” Negan hushed you, his eyes now focused on your lips which had you frozen in the moment. The rough pad of his thumb drew across your bottom lip and it had you leaning in closer to him. “You want a man to take care of you. Because older men know what’s best. They do it better. And I’ll take really good care of you.”

After the final word left his lips, Negan’s lips hovered in over yours drawing your eyelashes to flutter to a close. Claiming your lips in a faint kiss had you leaning in closer to him. Your body’s reaction to him was almost instinctive when you started kissing him back. The sensation of his fingertips sliding in over the small of your back was felt urging you in closer to him. Every caress of his lips ignited the fire inside of you more for him with the rough sensation of his short beard at your flesh.

Pulling away, Negan’s eyes were closed and he was smirking when his long eyelashes fluttered to an open, “You’re a special one. I can tell.”

“I’m sure you say that to all the people you see,” you commented with a half-smile, finding yourself wanting him to kiss you again with the way he was touching your face.

“We could work on your confidence though,” Negan hushed you, bringing you to him again so he could nip at your bottom lip. Giving it a gentle tug, he flicked the tip of his tongue out over the inside of your bottom lip making you purr. “You are a beautiful, charming, young woman. You could have given your virginity to anyone, and you picked me.”

Instead of responding, you leaned in to desperately bring your lips together again with Negan humming. When his lips parted, you brushed your tongue against his which had him sucking faintly at your tongue when you pulled back. The more you kissed, the more intense it seemed to get with his large palm sliding up over your side.

Hooking your fingers into his dark hair, you tugged firmly at it which had him growling out against your lips. With his tongue flicking out over yours, you found a sense of confidence in stroking your fingers over the center of his chest to tease at the thick curls of hair that covered it. Lifting your hands, you started to open the buttons in Negan’s shirt, eager to see more of him and he didn’t seem bothered by it at all. Instead, his lips just trailed off over your jawline, over the side of your neck and to your shoulder to push at the strap of your dress to get it down over your arm to kiss at the flesh that was there.

Tipping your head back, your eyes connected with his when you got the last button undone and pushed apart the material of his shirt. Palming up and over the center of his abdomen toward his chest, you were in awe of his slender form. His lips were parted, his breathing heavy while you learned the lines of his body. Tracing your fingertips over the detailed tattoo over his pectoral muscle, you didn’t know how you were going to get away with this whole thing considering you were already addicted to this man and you barely knew him. Pushing into his chest, you got him to slide back so you could crawl in over his lap. Looking up at you, you agreed that he was good at his job because he had the look of absolute want in his eyes with you over him.

“You are so fucking gorgeous,” Negan slurred, lifting up to hungrily kiss at the side of your neck, reaching for the other strap of your dress to tug at it. With a grunt, Negan tugged at the material getting it pulled down your body to about your navel which revealed your breasts to him with a bounce. It had him tipping back to look you over with his adoration in his eyes. A wicked smirk tugged at his handsome features when he tipped his head down to start peppering kisses in over your collar bone. Hooking your fingers into his hair, you tipped your head back with his wet kisses covering the swell of your breast. Surrounding your nipple with the warmth of his mouth had your head tipping back with a moan. Sounds of his wet kisses surrounded you, his hands squeezing firmly at your hips. There was no questioning that Negan was very dominant in the way that Negan touched and kissed you, but you liked it.

With a swirl of his tongue over your nipple, he nipped at the sensitive flesh before trailing his kisses over to your other breast where he pampered it just the same. Yanking firmly on his hair, you had him staring up at you with his dilated pupils which took your breath away. Stealing a forceful kiss from his lips had him moaning. You two were just jumping right in, but it felt right in the way that it was happening. Negan’s fingers had dropped to squeeze at the back of your thighs to caress the flesh that was there. Sliding further up, he cupped your bottom under the material of your dress and gave it a firm squeeze.

“You don’t kiss like a virgin,” Negan growled, smacking firmly over your bottom eliciting a gasp followed by a moan from you. Staring over your body, his eyes focused in over your breasts and he sucked at his bottom lip.

“How do virgins kiss?” you wondered, dragging your fingers across his wet bottom lip. A snicker fell from his lips before he took one of your fingertips into his mouth. Nibbling faintly at the tip, he followed by flicking his tongue out against it making you purr.

“For the most part? They are shy? Timid,” he slurred, lifting up enough to hover his lips just in over yours. “Inside of you is a dirty girl just waiting to break free from the restraints you put on her.”

“Maybe you can help her break free,” you whispered, caressing over his chiseled jawline and it had him leaning in closer to you. A growl fell from deep within him when you teased the tip of your tongue over his lips and he reached to pull you in closer to him so he could claim your lips again in a hungry kiss. The taste of him was addictive. The more you had of him, the more you wanted him. Your blood was pumping through your veins with your heartbeat hammering inside of your chest. A flush went to your face and a warmth was flooding to your core.

Confidence overtook you and gradually you ground yourself down over Negan. Dropping his head back against the couch, his hands slid down over your hips while you took your time rubbing up against him enjoying the friction that it caused between the two of you. Beneath the material of his pants, the firmness of his masculinity was growing harder and you could feel it pressed against your bottom. It felt good and by the sounds he was making, he approved.

“Good girl. I think we’re breaking down the walls pretty fucking quickly here,” Negan insisted, the vibration of his words against your flesh causing you to moan. Dragging your palms down over the center of his chest toward his lower abdomen had a sharp exhale falling from his throat. His eyes were still locked on yours when you dragged your fingers across the belt in his pants. Lifting his hips, Negan attempted to help you when you started to pull the belt out of the loops. Tugging at the material had a rumble of an amused sound escaping him. Dragging his thumb across your bottom lip sent chills throughout your veins. “Y’know what you want now darlin’, don’t you?”

“Yes sir,” you replied with a smirk when you started working open the material of his pants. How this man looked at you took your breath away. Curling your fingers at the waistband of his pants, he lifted his hips up to help you get the material down his slender body. A surprised breath fell from your parted lips with the way his erection smacked up against his lower abdomen. Licking your lips, you stare lifted to his eyes. Arrogance flooded his features when a crack of a smile tugged at his lips. “And suddenly I see why Michonne suggested someone else for my first time.”

“Does that mean you don’t think you can take it?” he inquired, his right eyebrow arching in curiosity with you reaching down to trace your fingertips over the underside of the shaft. Just the mere touch had his cock twitching and he bit down on his bottom lip.

“I’ve never been one to back down from a big challenge,” you responded and with a bob of his head, Negan seemed proud of you. Teasing your fingertips from just under the head of his cock down toward the base had him licking his lips in a seductive sweep.

“Thatta girl,” Negan snickered with your fingers curling around his shaft, drawing his hips to bounce up toward your grasp. Sliding in further over his lap, you took your time caressing over his body appreciating the way his eyelids grew heavy with lust. Your thumb swept over the ridge of the tip of his cock and he growled out. “I promise you, you’re gonna love what he’s gonna do for you.”

“I’m not scared of him,” you assured him with a wink enjoying the amused sound that escape his lips before his deep, raspy moan followed. Kissing down over his jawline, you took your time pampering his body knowing that while this was technically meant to be about you, you wanted to cherish the perfect specimen of the man beneath you. Nipping faintly at the side of his neck had him hissing out while you pushed his shirt further apart to reveal his chest to you. Adjusting your positioning over him, you started to kiss down over his collarbone and over the center of his chest. Lifting your palms, you stroked your fingers through the dark curls of hair over his chest and swallowed down hard. “You are fucking gorgeous.”

“I was thinking the same thing about you,” he clicked his tongue at the top of his mouth, humming out again when you leaned forward to kiss over the center of his chest. Your kisses tampered off over his nipple appreciating the moan you got when you circled your tongue around the flesh. Whimpering out, it was almost hard to focus when Negan’s palm flattened out between your thighs to caress over the warmth of your body. It had your hips arching in closer to him when you sucked faintly at Negan’s skin. “You are so fucking wet already.”

It surprised him when you pulled away from him and moved so that you were sitting beside him. Lowering your upper half, you pressed tiny kisses over his abdomen and toward the v line over his hips leaving his flesh with hot wet kisses. Purring out, you felt Negan’s fingers caressing over your shoulders and toward your neck with your kisses lowering down. Sinking his fingers into your hair had you mewling out. You liked how it felt like he was being possessive with you. Delicately wrapping your fingers around the thick base of Negan’s cock, you stroked over it a few times before pressing a faint kiss at the tip. It had him growling out and you loved the sound it drew from him. Dragging your tongue across the tip made you purr out when his fingers grasped tighter to your hair.

Flattening your tongue out over the tip collected the taste of him on your tongue. Focusing heavily on the teasing aspect of it all, you pressed hot, open-mouthed kisses over his lengthy erection causing his breathing to grow louder. By the time you finally took him between your parted lips, it drew the most intoxicating moan from him. With his girthy length, you were doing your best to pleasure him to the best of your ability, working to jerk him off at the same time while bobbing your head over his length. The strength of Negan’s hand at the back of your head also helped set a steady pace that you were comfortable with.

Once you seemed to have a handle on things, you felt Negan’s palm sliding down over your shoulders, over your back before extending out over your bottom to give it a firm squeeze. Another smack over your flesh had you moaning around his cock. It had him twitching beneath you. The wet sounded of your mouth filled the quiet hotel room. Pulling away with a wet sound, you stroked your hand over his body when you lifted your stare to see that he was watching you with awe.

“Lay back,” Negan instructed, getting up from the couch with his hard cock bobbing with the movement. Carefully pulling off his jacket, he set it on the back of the couch and eagerly slid out of his button-down shirt. Tossing it with the jacket, Negan took his time to shimmy out of his pants after managing to pull his boots off. Snapping his fingers, you obeyed his order when you carefully lowered yourself back against the couch. Your heart was hammering in your chest when Negan grabbed a tight hold of the material of your dress to get it down your body leaving you laying stretched out on the couch in just your black panties. Getting to his knees, he hooked his fingers loosely into your panties, urging you to lift your hips with the tug of them. “How did you know black was my favorite color?”

“Lucky I guess,” you whispered, a tingling sensation at your skin with the way that he was looking over you as he unhurriedly pulled the material from your body. Tossing the material aside, Negan brought your leg up depositing a gentle kiss over the inside of your ankle with his eyes locked on you. Gradually, his kisses raised further up your leg having you a breathless mess when he got to your knee.

“If you’re ever uncomfortable, just let me know,” he slurred, nipping faintly at your flesh before lowering down onto the couch getting himself comfortable between your thighs. Curling his arms around your thighs and under your hips, Negan pulled you in closer to him getting a gasp from you and it made him smile. “You have a very pretty pussy. It’s a shame you haven’t been letting someone pamper it like it deserves.”

Reaching up, the roughness of the pad of his thumbs traced a line over your sensitive folds and it had you dropping your head back, biting down on your bottom lip with a mewl. Down his fingers went over the lips, toward your entrance before circling back to go up and sweeping over your clitoris. It had you panting, his eyes watching you closely to see how you responded to things.

“Good girl,” Negan hummed, lifting his fingers up to suck faintly at the tips. “Daddy is gonna take real good care of you.”

Hearing him refer to himself as daddy sent a jolt straight to your core and you purred out, your hips arching up toward him with him releasing a sound of approval. Doing the same dance over your sensitive flesh, Negan started to pepper kisses over the inside of your thigh. Your breath was hitching in your throat and you wanted to tip your head back, but you couldn’t. You wanted to watch the beautiful man between your thighs that was there solely aiming to do nothing but please you.

Each kiss grew closer until the wet sounds of him kissing over your heated flesh was heard. Licking your lips, something that resembled a whine fell from them and he smiled against your flesh. Dragging out his tongue, he flattened it over the length of your folds dragging it from your entrance which had you tremoring upon contact up to your clitoris where his tongue circled before back again.

It was about learning your body and Negan was doing just that. Paying close attention to everything that made you react. With his lips surrounding your clitoris you found the cries that fell from you involuntary. Each sound you made seemed to fuel him only enhancing the sensation of what he was doing. And by the sounds he was making against your flesh? He seemed to be enjoying himself just as much, finding pleasure in the sounds he could draw from you.

Grunting out, he pushed into your thighs to lift your hips in closer to him. Dropping your fingers down, you hooked them into his dark hair when you felt his tongue circling your entrance before dipping inside of you with a strong sweep. Cooing out, you tugged firmly at his hair having him groan against your most sacred parts. A wet sound filled the air when Negan pulled back away from your body, licking at his wet lips.

Adjusting his body, he hooked his arm around one of your thighs while his free hand lifted to drag his fingers over your sensitive bundle of nerves. Sliding them down, Negan lifted his head when his middle finger circled over your entrance. Tipping your head back against the couch, you whimpered when he took his time pressing his long slender digit inside of you. A raspy moan fell from his throat when he felt the warmth of your body surround his finger and it made him smile.

“You okay?” he confirmed pressing a wet kiss at the inside of your thigh, leaving a tiny nip at your flesh when he pulled back. Nodding, you didn’t have much that you could say because you were so focused on the sensation. When he had the okay that you were comfortable enough, he started to drag his finger back before pressing forward into your body again. Biting down onto your bottom lip, you whimpered as Negan’s lips surrounded your clitoris sucking at the sensitive nub. Every part of you felt hot. He was taking his time with you, not trying to rush things and he was doing a hell of a job with it. Your body was already trembling and he knew what he was doing to you when he inserted another finger into you. One thing about Negan’s fingers? They were big and he knew just where to caress inside of you to have your writhing beneath him, your hips arching up toward the talented caress of his lips and tongue over your clit.

“Fuck,” you gasped, lifting your head to watch him while he pumped his fingers inside of you, hitting a certain spot that had your toes curling, your fingers clinging tighter to his hair and your cries growing louder. Loud, wet, slurping sounds were filling the air and an occasional moan from Negan would vibrate against your flesh. Your thighs tensed up, starting to twitch when you tried to hold back, but with what he was doing at feasting on your body had you moaning out his name. A pleased groan pressed against your flesh when the thrusting of his fingers grew stronger when he clearly got you to an orgasm. Your muscles tensed up, a rush flooding to your head leaving you absolutely breathless. “Oh my God.”

“And that’s just the start,” Negan snickered after pulling his mouth away from your body. When his fingers left you, a whimper followed. Seeing him using those same fingers to drag them across his bottom lip had your heart hammering harder inside of your chest. Sucking at his fingers, Negan groaned at the taste of you over them before reaching for you. Managing to pick you up and throw you over his shoulder had you gasping and clinging tightly to him. A firm smack was placed to your bottom and it made you moan. “Daddy’s got you darlin’. Don’t worry.”

Once Negan made it to the bedroom, he was careful in the way that he lowered you at the center of the bed. That’s when the room started to spin around you. Suddenly this was becoming all too real what was about to happen. Your eyes fell to Negan’s swollen cock and you felt your mouth go dry looking at it.

“I’ll be right back,” Negan held his finger up, going into the sitting area to grab something before returning with a condom and some lube. Getting onto his knees at the bottom of the bed had a breath catching in your throat when you pressed up onto your hands. Outstretching your hand, you palmed in over the center of his stomach, dragging your fingers down over his navel to tease through the dark curls of hair that were there that led to the base of his thick cock. Stroking his fingers over your shoulder, Negan hummed when you started kissing at the area right below his bellybutton. Grasping his shaft firmly, you took the tip back between your lips with your eyes staring up at him hoping to see his reaction while you pleasured him. The vein at the side of Negan’s neck was slightly bulging when he dropped his head back and moaned out. “Fuck.”

Allowing you to give him a blowjob for a few moments led to him curling his fingers into your hair to pull you back. A wet popping sound followed when your lips pulled from his cock and he stroked the saliva over his body.

Reaching for the condom, Negan urged you to wait. Still caressing over his hip, you wanted to make sure to still touch him when he went to open the condom.

“Do you use a condom with everyone?” you questioned noticing the smile that tugged at Negan’s lips when his thick eyebrows bounced up.

“Kind of the rules, so yeah,” Negan answered you, licking at his lips when you wrapped your fingers around his cock to stroke over it firmly. “Why? Do you want me to do it without a condom?”

“You’d do that?” you were almost intrigued when he smirked, his hips bouncing up toward your grasp.

“Well, you’re a virgin. I know I’m clean because I have to make sure of it,” Negan bobbed his head back and forth, sucking at his bottom lip when you dragged your tongue out over the length of his cock again. It had him moaning out, his long eyelashes fluttering to a close again. Truthfully? You didn’t care what he did. You just wanted him and you wanted him bad. “I can make an exception for you if you can keep a secret.”

“Keep a secret?” you mused, kissing at the underside of his cock having him humming out when his eyes came to a close. “Will your boss really get that upset with you for having unprotected sex with someone? You’d be willing to get in trouble for me?”

“Would Michonne get pissed at me? Probably. But you’re worth the risk,” Negan’s fingers curled around your throat, leading you back against the bed. A sharp exhale fell from your throat when he set the condom beside you on the bed and reached for the lube that he brought. Releasing your throat, he opened the bottle and poured a significant amount into his hand before stroking it over his cock slicking his girthy length with it.

“Is there much of a difference?” you whimpered when Negan very slowly crawled in over you, covering you with the weight of his body. The warmth of it radiating against your flesh.

“It’s more intimate,” Negan started peppering kisses over your lips, nipping at your bottom lip. “Some men like wearing condoms because it prolongs their orgasm, but I last long regardless.”

Lifting your head, you looked between the two of you to see that his cock was resting against your lower abdomen and it made you lick your lips. A sense of panic filled your veins in that moment, but Negan reached for your jaw to get you to rest your head back.

“Are you on the pill?” Negan confirmed and you nodded your head, feeling a rush of excitement with the smirk he gave you. Balancing himself on his left arm, Negan reached down between the two of you and you felt him dragging the swollen mushroom tip between your lips causing you to whimper. “It’s okay. Don’t get worried now. You’ve been such a good girl so far. Daddy is gonna take good care of you.”

Smacking sounds filled the air with Negan tapping his heavy cock against your sensitive clit getting you to arch up toward him. Hovering his lips in over yours, Negan adjusted himself before lining himself up with your entrance. Lowering over you, he reached for your wrists to pin them beside you on the bed. Squeezing firmly at them at first, Negan had you shaking beneath him when he slid his fingers to tangle his with yours. Pushing forward had the swollen tip entering you pushing past the ring of muscle that was there. It had Negan’s lips part, his jaw lowering and his eyelids growing heavy. Your cry followed with Negan dipping down just enough to press a faint kiss over your lips.

“Fuck,” Negan nipped at your lips when he pushed his hips forward just a bit more leaving you with a completely foreign sensation. It hurt at first, but you assumed that was normal since Negan from what you knew was bigger than most men were. “Look at me.”

Your eyes connected with his when he filled you with just the first few inches. His fingers squeezed tightly to yours, your whimper falling from your lips. Allowing you to get used to just that, Negan started to pamper you with kisses, pulling his hips back slightly allowing the tip to pull from you before pushing it back in. It was a unique feeling, but with every motion, you found your hips raising to meet his movements.

“Tell me if you need to stop,” Negan growled, the warmth of his breath hovering over your lips, but you didn’t want it to stop. No, you wanted more of this. Lifting your hips up higher toward him, you gave him a nod letting him know you wanted him to give you more and it made him smile. Rolling his hips, Negan filled you completely leaving you to let out a moan. God, you felt so fucking full with him inside of you. And you liked it. It was uncomfortable, but you felt like in that moment you belonged to him and every part of you was his. “Fuck, you are so goddamn tight.”

“Your cock is so big,” you whined against his lips, lifting your head up to meet him in a desperate kiss that he was eager to reward you with. You wanted him to move, but you knew that he was giving you time to get used to him. To feel him and be close to him. A loud, throaty moan escaped his lips with his eyes squeezing shut and you purred out. “Please…”

“Move your body with mine,” Negan instructed, his hips rolling back before pushing forward again. Doing what he said, your hips eagerly met every one of his thrusts and you winced when each movement started to get harder. “Do you wanna stop?”

“No,” you shook your head. You knew the pain would subside because with each movement the pleasure started to grow. The friction from his groin rubbing up against your clit felt incredible and you rocked into every movement he made. Plunge after addictive deep plunge had you moaning out, whimpering out his name and enjoying that he was just as much verbal as you. Burying his nose against the side of your neck, Negan kissed over your flesh and the smacking of your skin together felt incredible. “Do you like that tight little pussy?”

“Fuck me,” Negan pulled back with a wicked smirk, his left hand pulling from your hand to slide up over the side of your neck to grab a firm hold of your jaw. “I think you just might be my favorite.”

“As long as I’m yours,” you exclaimed, dropping your head back with the incredible sensation that Negan thrusting inside of you was giving you. Once he found a certain spot, his thrusts were planned and meticulous.

“You’re so fucking wet,” Negan hissed, dropping his head to watch his cock already coated in your slick while he thrust into you time and time again. The tip of his cock was rubbing up against your g-spot in varying different speeds and it hand your toes digging into the back of his thigh muscles. Your cries turned to breathless pants, with you trying to lift your head to watch what he was doing, but he shook his head. “How do you feel?”

“So good,” you answered with a whine knowing that at this point it was true. Whatever Negan was doing, he was doing it right leaving you with a tingling sensation flooding your body. Desperately reaching up, with your free hand you brought Negan to you to kiss him with his tongue brushing up against yours and his fingers squeezing tighter where he was still holding your hand. By the sounds you were making, Negan must have picked up on the fact you were about to come because his thrusts grew more determined. With a wail, you pulled your hips up and away from Negan, which was followed by a proud, amused sound. Your eyes slammed shut, your hips shaking with Negan’s free hand dropping to caress over your sensitive bundle of nerves, enhancing your orgasm with his caress. “Fuck! Fuck…”

“Look at you,” Negan snickered nuzzling his nose against the side of your neck with your coos of pleasure surrounding him. “Your first time and you’re already soaking daddy’s cock. Kissing up over the side of your neck, Negan let you take a moment to gather yourself before hovering over you again. “Put your arms around my shoulders. Hold on tight.”

Nodding, you did as he instructed and gasped when he pulled you up and got into a kneeling position on the bed. Getting you to straddle his hips, Negan reached between the two of you and helped you lower down over his cock while you braced your feet on the bed with Negan’s hands bracing against your ass. Dropping your head back, you cried out at the way he filled you.

“You like the way that feels?” Negan slurred against your lips, starting to use his strength to help you bounce yourself over his cock. Your right arm stayed hooked around his shoulders to keep you up, while you balanced yourself back on the bed with your other hand to help your movements. “Fuck, your tight virgin pussy feels so fucking good around my big cock.”

“Yes,” you gasped out, following the way that Negan was instructing you to move your hips over his cock allowing you to take all of him again and again. You probably sounded like a broken record with how many times you were saying it, but it felt so good at this point. Bracing your left hand now instead on Negan’s thigh, you angled your hips hoping to get as much of him as you could. The wet sounds along with the two of you breathing heavily together filled the hotel room. “Your cock feels so good inside of me. Oh my god.”

Every roll of your hips over his length grew harder with his moans matching yours, “That’s my girl. You’re doing so fucking good.”

Whimpering out his name as he kissed down over the side of your neck, you couldn’t help but cry out with his right hand squeezing over your bottom to bring you over him while his left hand caressed up and over the small of your back. Pressing his forehead to yours, Negan made sure to keep the both of you close. Once your moans started to become closer together, Negan worked harder to bounce you over his cock.

“Are you gonna come?” he whispered and you nodded quickly, dropping your head back in ecstasy with the way he continued to fill you. Pulling your hips up and away once you hit your next orgasm led you to a euphoric sensation flooding your body. “Fuck, you’re just loving this aren’t you?”

“So much,” you whined when Negan seemed to easily grasp a hold of your hips to flip you over onto your stomach. Lifting your hips up just enough, Negan lowered down behind you with his tongue lapping at your body. His rough grasp palmed at your bottom having you crying out at the sensation. Not only was Negan doing what you paid for, he was going above and beyond to bring you to as many orgasms as he could. Curling your fingers around the comforter, you dropped your head and enjoyed the slurping sounds that came from Negan.

“Lower down baby,” Negan bit at your bottom making you purr as you felt his hands helping you to lay flat against the bed. Crawling in over you, Negan hooked his arm around your waist to pull your hips up slightly before leading his body back into yours with a wet sound. It had you both moaning out in unison with him nipping at your jawline when his steady thrusts started back up again. “I’m so happy you saved this tight little pussy for me. It’s like you were made for me.”

“All for you,” you hummed, happily accepting his fingers hooking with yours with the sounds of his hips smacking up against your bottom filling the air. “It belongs to you.”

“Oh yeah?” Negan’s free hand curled around your jawline to put a firm pressure on it having you wincing out in pleasure. “Who does this tight little pussy belong to?”

“You,” you whined with his thrusts growing stronger from behind you. “It belongs to you.”

“My name,” Negan demanded, his lips claiming yours having you crying out against his lips.

“Negan. It belongs to Negan,” you gave him what he wanted to hear, nipping at his bottom lip when he released an amused rumble of a sound. “I’m all yours.”

Snickering against the side of your neck, Negan chuckled before quickening the pace of his cock thrusting inside of you. You couldn’t believe how quickly you became addicted to the sensation of him stretching you and filling you completely.

Your moans countered each other’s with the sound of the headboard smacking against the wall. You wondered if anyone would complain considering you knew that the two of you were not being quiet. At all. Cooing out, your hips tried to pull up and away from Negan’s feeling that same build up he had done before inside of you so many times, but his hips followed your movements doing his best to keep moving inside of you until you pulled away with a whine.

“Christ,” your body shook and Negan moaned against the side of your neck. Just his body weight over you felt good and you didn’t know how you weren’t going to want this constantly now that you’ve had it. “Negan.”

“Come here,” he instructed, nudging your hip and getting you onto your back again. Getting comfortable, Negan braced his weight and got you to hook your legs around his waist. Your bodies were pressed together with his fingers sweeping over your jawline and his hazel eyes locked on yours. “You are so fucking perfect.”

Gasping out as he entered you again, your fingers slid up the lengths of his back before sinking into his hair. Smiling had his dimples even more prominent than before when he took his time rolling his hips back before forward again. This time it was about closeness and the connection between the two of you. Gradually with each thrust, the strength grew harder and quicker. Desperate to have him near, you pulled his lips to yours demanding the attention you wanted. Winces started falling from Negan’s throat with his moans growing louder.

“I’m going to come,” he grunted against your lips, his thick eyebrows furrowing with his lips parting and his moans becoming even raspier. Arching your hips up toward his thrusts, you lifted your head just enough to meet his dominant and forceful kiss. Each thrust became rough, with your winces against his lips drawing him to growl out. Biting at your bottom lip, Negan’s moans grew closer together when you felt the throbbing of him inside of you followed by the first sign of the warmth of his release. The expression over his face as he continued the rolling of his hips over you only turned you on more when you pulled him closer to you kissing over the side of his neck. After a few final thrusts, Negan’s breathing grew loud and he nuzzled his nose against the side of your neck with you clinging tightly to him. Negan pumped you full of his cum, his cock still throbbing inside of you after he reached his orgasm. You were surprised how much you enjoyed the feeling of it. “Fuck.”

Stroking your fingers through his damp hair, you felt like the world was spinning around you. Your body ached in the most amazing of ways and you loved the sounds of Negan’s deep breaths against the side of your neck.

With a throaty groan, Negan pulled his hips back and away from you allowing his softening cock to pull from your body. Whining out, you hated the empty feeling it left you with, but you felt the warmth of his release spilling out of you and sliding down your thighs.

With a grunt, Negan got up from the bed and you felt your heart sinking. Throughout the whole thing, Negan made sure to make everything very intimate between the two of you, so when he stood up you almost assumed that he was already getting ready to leave. He had done what you had asked of him of course, so what more did he need to do?

Closing your eyes, your breathing started to calm down with your skin feeling like it was on fire. As the bed dipped, you found yourself surprised to feel the warmth of Negan beside you again. Opening your eyes, you felt him wiping at the mess he made over your thighs with a tissue and you reached up to stroke over his jawline.

“I thought you were leaving,” you declared while Negan finished cleaning you up. Tossing the tissue into the garbage, Negan crawled in over you again and traced over your features with his rough fingertips. The way he looked at you took your breath away and you stole another kiss from his lips.

“Nope,” he shook his head with a smirk, peppering playful kisses over your jawline then your shoulder and then to your breast. Nipping at your nipple had your back arching up toward him and he growled. His left hand caressed in over the side of your body and you hummed. “You did so good. How do you feel?”

“I feel good,” you answered with a hum as hand lifted and his thumb swept over your bottom lip. “I mean, I ache, but I feel really good.”

“Good,” he slurred with a happy smirk, pressing another kiss to your lips before rolling onto his back and pulling you with him. Resting your head over the center of his chest, you stroked your fingers over the damp hair that were over his lower abdomen. Pressing a kiss to your temple, Negan squeezed you in closer to him and it made you both smile. “Do you regret your decision?”

“Not one bit,” your answer was immediate, drawing what sounded like a snort from his lips and it made you lift your head from his chest to stare up at him. “The only thing I’m starting to regret is that this will be over soon.”

“Not that soon. You have me all night,” Negan reminded you with a wink, his raspy voice drawing you in to kiss him again. With an arrogant bob of his head, he gave you another one of his sexy smiles before squeezing over your bottom. “Which means I’m yours until morning.”

“Oh yeah,” your eyebrow arched in curiosity and he nodded his head.

“And lets not pretend that this is gonna be the last time,” Negan declared, his nose nuzzling in against yours when he claimed your lips in a kiss again. “We both know that after tonight, you belong to me. All of you belongs to me.”

----

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#hELLO????¿#x reader #notsfw #ive seen this prompt before and listen its my Favorite

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