SOUTHSIDE GIRL
Summary: based on the theme around the tv show Shameless. Y/N lived in the southside of Chicago all her life with her three other siblings she basically is raising. Getting out finding a nice steady job for once, her boss Negan Smith seems more than happy to treat her like a queen.
Warnings: 18+, smut, major shameless vibes!- I mean if you watch shameless you know, lower income households!, mentions of smoking!, rich Negan!, reader has three siblings!, daddy issues, small daddy kink!, slight mommy issues!, cursing, praise kink!, drinking!, anger issues!, dom negan!, lower income neighborhood!, rough sex!, major family issues!, semi-public sex!,jealous tendencies!,age gap!, cursing, and not fully edited.
A/N: thank you all for 275 followers!! I haven’t been doing this too long and getting support and the love is honestly appreciated!! I am currently working on drafts with the yearly vacation! I lost inspiration for a bit but it’s coming back thankfully!! Now, this is FULLY based around shameless tv show- which I’m currently rewatching! This honestly could be a series
The club was unbelievably loud.
Y/N and Valerie had just left the dimly lit bar and entered the pulsating crowd to join the dance floor. The two had met a couple of years ago in the bustling city of Chicago and had quickly become inseparable best friends. Valerie had been out in the town when she stumbled upon Y/N at a bar, and they hit it off immediately. Despite living on opposite sides of town, Y/N was on the south side of town.
Her life was different.
Valerie and Y/N had been at the club for a few hours. They had been sipping on drinks and swaying to the music on the dance floor, surrounded by a crowd. Y/N had a smoke break, and Valerie finally returned to the dance floor as they danced together. "I noticed that man was eyeing you at the bar earlier," Y/N responded with a smile. Valerie playfully rolled her eyes, "Don't worry, I won't leave you alone. I know plenty of men have been checking you out all night."
Y/N laughed, rolling her eyes playfully. “None on my eyes, though,” Y/N admitted; she was perfectly fine. Usually, they just turned into one-night stands or a fling relationship for a while. “Come on, let's get a drink and sit down for a bit, yeah?” Valrie implied, fixing her heels while the girls walked their way back to the bar, “these fucking heels are killin’ me.”
Y/N couldn't help but laugh as she took a seat beside her friend at the bar. The ambiance was lively, and the bartender greeted them with a warm smile. "What can I get you two lovely ladies?" he asked, his hands resting in front of them on the bar. Valerie, with a playful wink, ordered two vodka shots and two spiked lemonades, handing him the cash and telling him to keep the change. The clinking of glasses, the buzz of conversation, and the soft glow of the dimly lit bar all added to the atmosphere.
Y/N scanned the dimly lit bar, her gaze was drawn to an older, yet undeniably attractive man a few feet away. Leaning casually on the bar, he held a glass of what appeared to be whiskey and his eyes were fixed on her. Despite the distance between them, his gaze was intense and impossible to ignore. Y/N's lips curved into a subtle smile as she turned back to Valerie, who was already gushing with excitement. "He just gave us another round of shots for free!" Valerie squealed, placing two shots in front of Y/N along with her drink.
Y/N gestured to the numerous drinks placed in front of them. “Yeah, no more drinks for me after this." Valerie snorted and responded, "Free shots are free shots, girl!" She quickly grabbed her shot and brought it to her lips, handing Y/N's over to her to take together. The shot was bitter; it made her throat tighten. She sipped her spiked drink a bit, grimacing at the shot, shaking it off rather quickly.
As Y/N and Valerie were enjoying their drinks at the bar, a young man with his eyes on Valerie approached them. He seemed to be around the same age as them, and his charming appearance caught Y/N's attention. He had a drink in his hand and appeared quite confident. Judging by Valerie's body language, it was clear that she was interested in him as well.
"Hey," He spoke to Valerie with a smile. "I was wondering if you'd like to dance with me for a bit?"
Valerie was hesitant to let herself go, but Y/N reassured her with a nod. "I'll be fine at the bar. Go, babe," Y/N reassured her with a confident smile before Valerie took the man's hand beside her and began a conversation. Y/N watched as they made their way to the dance floor, getting lost in the crowd. Suddenly, Y/N felt a presence near her and heard a deep voice she didn't recognize.
“Can I buy you a drink sweetheart?”
Y/N's focus was drawn to the rugged-looking man across the bar, who had caught her attention earlier. He was a middle-aged man, clad in a leather jacket that seemed to fit him perfectly. As she took a closer look at him, she couldn't help but notice his rough facial hair. What particularly caught her eye, however, were the intricate tattoos that adorned his hands, stretching up his arms and disappearing under his jacket. Suddenly, he saw her gaze, and with a charming smile, he signaled the bartender to bring them another round of drinks.
Y/N flashed the man a warm smile, finishing the last sip of her drink. "Who says I want a drink from you?" she asked, a playful smirk on her lips. Despite knowing she should not be attracted to this mysterious man, Y/N was drawn to his dark chuckle and intense gaze as they locked eyes. As the bartender placed their drinks in front of them, the man spoke up. "I thought you might like some company. I've been watching you all night," he admitted, picking up his drink.
Y/N scoffed out playfully, her eyes rolling with a smile. “Oh, don't be a stalker. It isn't sexy.” Y/N playfully teased the man, who gave her a warm laugh. “I thought you women liked it when we were stalkierish.” Y/N knew she was blushing like crazy, she hoped the night club lights covered up her reddened face.
“Negan.” The man held his hand out for her to shake, which made her laugh; she couldn't stop laughing with him. “Y/N, you're an oddball, aren't ya?” Y/N teased, sipping her drink and leaning against the bar resting in her chair.
“Maybe so, sweetheart. Only one way to find out: stay talkin’ to me.” Negan smile was even drawing her in; she knew this could be a bad idea. Y/N's lips pierced; she did not want to stop talking to him, but a small voice inside her head was telling her to stop. “Let's see if you can keep my attention, Negan.” Y/N eyes were eating this man alive, and he saw right through her. The older male chucked, sipping his drink.
“You from here?” Negan wondered, his eyes trailing down her body. He'd been watching her for weeks, the only woman that ever caught his attention in this place. “Southside,” Y/N admitted she was never ashamed of who she was. “Southside girl, huh?” Negan's voice was playful, his smirk still plastered on his face, “All you south side girls crazy?”
Y/N snickered at his comment, shrugging and finishing the rest of her drink. “We are bat shit crazy.” Y/N teased him once more, and she couldn't help but flirt with this man. “I think I can manage with that.” Negan gestured to her empty drink, “Want another one, sweetheart?”
Y/N nodded, continuing to talk to Negan. They shared stories and experiences that they would never have revealed to anyone, but in that moment, they felt safe enough to confide in each other. The connection they formed was quick to create, and they both knew that this conversation would stay with them for a long time.
Negan was a successful executive who held a position of authority at a prominent company in the bustling city. Having recently gone through a divorce with no children, he confided in Y/N that his dedication to his work had taken precedence over his relationship with his former partner. Despite his busy schedule, Negan frequently visited the local club with a few of his close poker buddies, hoping to meet new people.
Amongst all the women he had met, Y/N was the only one who caught his attention. As the night progressed, Y/N opened up to Negan about her new job that she recently just got. How she and Val were celebrating, and she started the next day. Y/N needed this job desperately, even expressing some to Negan.
Despite her usually reserved nature, Y/N found herself opening up to Negan and sharing more about her life with him.
“Shit, your parents are dicks no offense sweetheart.” Negan and Y/N were on their fourth drink, Y/N even snorted at his comment not even disapproving of his comment. Her father was in and out of the house, the neighborhood drunk. Her mother went insane taking off when Y/N was young. She barley told anyone about them, how she was at home even still with her siblings.
“I don't take any offense, trust me.” Y/N knew she was feeling the liquor. She felt like her and Negan could continue talking for hours. Valerie was the only thing that helped Y/N return to reality and down to where time existed.
Valerie and the man who offered her dance had been dancing for an hour, which surprised Y/N how long she had been talking to Negan. “We were going to party a bit more; you good?” Valerie asked her best friend, her eyes shifting between the two with a smirk.
“I think I can manage.”
The two were left alone again; Y/N hated how she wanted to throw herself onto this man already. Hell- that's what most of her one-night stands were. Most of them even have this much talking. Y/N figured this was how the night would end. He would be deep inside of her, pounding her, not that she is complaining.
Y/N's hand was resting on Negan's, and as they locked eyes, chills ran down his spine. He felt his eyes darken with desire, even though he knew he shouldn't be feeling this way about a younger woman like her. "I may be coming on too strong," she spoke out, her grip on his hand tightening. "But we could go off somewhere, too." Her voice was low and husky, sending shivers down his spine. Negan could feel the heat rising between them, and he knew he had a decision to make.
For the past month, he had been frequently visiting this place, but it wasn't until he saw her that he felt truly captivated. Every time she hit the dance floor with her friend, he couldn't help but watch her every move. There was something about her that seemed to radiate an aura of energy and joy, making her stand out from the crowd. Eventually, the moment he saw her alone, he knew he had to make his move and approach her.
He knew she was just different.
The silence sitting thick between the two was suffocating. Y/N and Negan were standing face to face, their eyes locked in a heated gaze. Y/N was well aware of the fact that what she was about to do was not the best decision, but her eagerness got the best of her. Negan, on the other hand, knew that he shouldn't be doing this, but he couldn't resist the grip of Y/N's hands.
Suddenly, Y/N broke the intense silence between them, "I'm gonna go use the little girls' room, wanna make sure no one messes with me?" She pouted her lip, playfully begging Negan with her eyes. Negan's lips curled up in amusement as he saw right through her playful act.
“Lead the way, sweetheart.”
Hand in hand, going through the crowd, they headed off to the bathroom, which Y/N barely saw empty, but this time, they both were lucky with no line to the toilet. Down the hallway, the music silenced; before Y/N could entirely turn around, his lips were against hers as soon as the guilt hit her. Y/N could barely take her next breath and forced her into the bathroom room behind her. He quickly twisted the lock, having Y/N against the door wrapped around his body. He had his hands roaming her body like he had been wanting her for months. She could not say much with how her hands were all in his hair, roaming her nails down his clothed back.
Y/N felt the dress that hugged her thighs trail up along with his hands, squeezing her thighs roughly. The pain mixed with pleasure made her moan into his kiss, his lips resisting to move from hers. Negan had her quickly near the nearest wall, still having him wrapped around him in his lap. Y/N could already feel his thick cock pressing against his core; she reached into his pants to unzip them. Began stopped her hand for a moment, finally meeting her eyes.
Her face flustered, still the prettiest woman he'd ever met. “You did somethin’ like this for?” means words rolled off his tongue, and his eyes were darker and filled with lust. “I don't think that's any of your business, old man.” Y/N teased, getting a chuckle from Negan, squeezing her sides that tickled her slightly.
“Enough with the questions, fuck me.”
“Oh, you naughty girl,” Negan lip rubbed up her cheek, then teased her neck with tiny kisses. Y/N’s head laid back, giving Negan full access to her. Negan placed her hand on the palm of his jeans, letting her unzip his pants, “fucking a stranger In a bathroom. You little slut.”
Y/N whimpered, pulling out his thick cock as his jeans hit the floor along with his underwear. Negan’s fingers work expertly to her drenched cunt, pushing her underwear aside. He then let two of his fingers easily slide inside her wet cunt. “Shit girl, you’re still so fuckin’ tight.” He growls against her lips, Y/N tasting the alcohol on him, gripping his neck, letting his lips move against hers again.
Negan slipped his fingers away just when her orgasm was coming, she growled underneath her breath from the loss of touch. His cock teased her folds, moving to her entrance. His hands dug into her thighs, and she knew that she'd have bruises. “Please, fuck me,” Y/N begged him.
Both groaned aloud as she sank over Negan’s length, stretching her walls. He rocks you in her lap, thumb against her clit. Whimpering, Y/N nibbled on her bottom lip as he fucked her up into her against the wall. She held onto his neck for support, his hands covering her mouth. Negan groaned slightly into her neck; she felt his thrust get sloppier by the second.
They both stopped suddenly; Y/N felt her stomach drop, hearing the muffled music outside the bathroom. The door handles jiggle. Both looked at the door; Negan continued his thrust, getting deeper inside of her. Y/N moaned against his hand that still rested on her mouth, her eyes rolling to the back of her head.
“Fuck off!”
Y/N couldn't help but let out a laugh which Negan shared with her continuing his thrust, holding her now by the jaw and continuing to fuck her.
“Oh god— oh god—”
“Yeah, baby girl, that’s it,” Negan whispers huskily into her ear. His pace magnifies, thrusting up into her so hard that he can also make her scream. It was thick and hot, and Y/N could feel sweat all over her. “Good fuckin’ girl, that’s it; come round Daddy’s cock nice and hard.” Y/N soon slumped in his lap, uneven breaths rattling in both of their throats, feeling Negan come inside of her, her nails dug into the back of his neck, pulling his curls. Negan’s hands continued to roam her thighs, the words sending her over with her orgasm.
Both quickly cleaned up; Y/N wiped the running mascara down her face, trying to straighten up her dress. “After that, I think I need to ya again.” Negan laughed, pulling her to him and getting himself back dressed. “I am not a normal girl, Negan.” Y/N tried to tell him warmly how she felt, “I'd love to see you again, but I think I'd have you running off in a heartbeat.”
Negan kissed her cheek, and a smirk widened across his lips. “Don't worry, sweetheart; I think you'll see me again.” He left her in the bathroom alone. Y/N finally let herself come back down to earth, breathing and looking into the mirror.
She definitely was a different girl.
Y/N didn't even have time to think about last night.
“You guys, the bus leaves at 7:10AM sharp, let's go!" Y/N frantically yelled. Her little sister, Hannah, was brushing her teeth beside her, while her twin brother, Hayden, was still in his underwear, refusing to put on his pants. Y/N tried to reason with Hayden, "Hayden, pants now!" Meanwhile, Kevin, their other brother, was chasing after Hayden, causing chaos in the house. Y/N had to be careful not to get knocked down by the running boys as she grabbed clothes from the bathroom hamper.
Y/N couldn't resist a small smile as she made her way down the stairs, the sound of her sibling's roughhousing filling the air. "Boys please!" she called out, her voice firm but gentle as she attempted to restore some order in the chaotic household. With a bundle of clothes in her arms, she continued on to the laundry room, hoping to get the chore done without any further interruptions.
Her life was definitely different.
Y/N did a lot for her siblings, maybe too much. But her parents weren't around to help. Since Y/N could remember, it had always been like this.
Y/N, a woman in her twenties, was the eldest among her siblings. She assumed the role of taking care of her younger brothers and sisters. Her siblings were everything to her.
Hannah and Hayden are identical twins; both just started the sixth grade. Y/N had some help from their other brother, Kevin. Kevin was 15 years old; he was such a bright kid.
After struggling with the washing machine, she had breakfast already prepared for them, with eggs and toast neatly arranged on the kitchen counter. The bags containing their lunches were already packed and waiting for them, wrapped in brown bags.
Y/N was in the kitchen, cleaning the dishes and exchanging greetings with her siblings. As she worked, she could hear the sound of footsteps coming down the stairs. It was Kevin, her brother, who walked in and grabbed a couple of clean glasses from the cabinet. "Everything's ready to go, try to eat up quickly," Y/N said with a warm smile. Kevin poured himself and his siblings a glass of juice and then turned to Y/N.
“You're starting your new job today?" he asked with a curious look on his face. Y/N nodded, feeling a hint of nervousness in her voice. "Yeah, my shift is at 9 AM. Supper may be a little late tonight," she admitted. It had been a long time since she had worked a 9 to 5 job, and the thought of it made her feel a bit anxious. For the past few months, she had been doing odd jobs here and there to make ends meet.
Y/N got lucky with this job, she knew she could not fuck it up.
"Hey Kevin, do you think you could come up with a dinner?" Y/N requested as she looked at her brother hopefully. Kevin gave her a quick nod and patted her back, offering to help with the breakfast plates. "Go get ready for work, I've got this. Don't worry about dinner tonight," he reassured her. Kevin was proud of his sister for landing a job that made her so happy, and he was willing to take on multiple jobs to help pay the bills and support their family. He was glad to be able to contribute in any way he could, including taking care of their siblings.
"Thanks, alright you two I love you, have a good day." Y/N gave a quick hug to the younger twins, "I better not get any calls of any fires Hayden." She rubbed the top of her brothers head playfully messing up his hair. "No promises." Hayden playfully pushed his sister away with a laugh, holding his plate of breakfast.
Hannah, with a hint of anxiety in her voice, “Any news on dad?” They were all seated around the kitchen table, the smell of freshly brewed coffee filling the air. Y/N and Kevin exchanged a meaningful glance, and then Y/N turned to Hannah with a reassuring smile. "I have a feeling he'll be back home in a few days, Hannah," Y/N said in a gentle tone. "Val mentioned that she saw him at work last night at her bar, so he's probably just taking some time for himself."
Y/N had a heavy heart as she thought about her father. She knew that he was probably sleeping beneath a bridge with a terrible hangover, but despite this, he seemed invincible. Nothing could take him down. She had long stopped worrying about him and instead focused on taking care of herself and her siblings. She knew that their well-being was now solely in her hands, and the weight of that responsibility was heavy.
Y/N had a cup of coffee, heading upstairs to prepare for her first day at work; she finally had time to reflect last night. She and Valerie went out just to party at that nightclub just to celebrate her getting a new job, yet she ended up fucking someone in the bathroom.
A stranger.
Maybe this was not new to her, but she at least never had sex in public- not with a stranger. All she knew was his first name, Negan. All she could think about was his hands over her mouth, covering her whimpers from moaning his name. Y/N groaned to herself looking at herself in the mirror trying to get ready for the day.
She knew she couldn't fuck this job up, this was the best place she had her self yet. Y/N kept telling herself, not to fuck up.
The city was about 30 minutes out from the Southside, Y/N did it every weekend usually with Val. The city was always busy, no matter the time of day.
As Y/N got ready for work, she wore her office attire that Valerie had kindly lent her from the goodwill. After driving around for a while, she finally managed to find a parking space in the crowded parking garage. With her belongings in hand, she made her way to the elevator, ready to start her day. Y/N's office was located on the 12th floor, and she knew that she would have to start small. She wasn't even going to have her own office yet, and would spend most of her day sitting in front of a computer screen.
Y/N's heart was racing,she desperately needed the job, but she couldn't shake off the feeling that she didn't belong here. Growing up in the rough neighborhood of the southside, she was used to a completely different atmosphere. The thought of being surrounded by snooty, high-level executives made her feel even more out of place. She prayed that she would never have to go up there and face their judgmental eyes. Despite her nerves, she took a deep breath and walked into the building, hoping that she could prove herself.
Y/N walked into the building with nervous excitement. The woman at the front desk looked up and greeted her warmly. "Hi," Y/N said, "My name is Y/N L/N and I'm here for my first day. Tony told me to ask for him at the front desk." The older lady smiled and paged Tony through the intercom. Y/N knew Tony was the boss on the floor, and the Vice President of the company. She was sure it would be a while before she met the big boss, who probably wouldn't even give her the time of day. "He will be with you shortly, sweetheart. Please have a seat," the woman said, gesturing towards the chairs behind Y/N. Y/N sat down, her leg bouncing with anticipation.
Y/N’s thoughts wandered off to the man she met last night, Negan. His name echoed through her mind, refusing to leave her thoughts. She felt silly for constantly thinking about him, but the desire to talk to him again was overpowering. She despised how badly she wanted to bump into him at the bar again.
As Y/N walked into the office building, she felt a sense of excitement and nervousness. She had been eagerly waiting for this day for weeks, and now it was finally here. As she entered the reception area, a man approached her with a warm smile. It was Tony, the Vice President of the company, who looked like a kind and welcoming person. Tony greeted her, “Welcome Y/N!” Y/N returned with a smile and thanked him for the opportunity, feeling grateful for the warm welcome. Tony then led her through a long line of desks, where she saw people working diligently on their tasks. Some of them looked up to see her, but most of them were engrossed in their work. Y/N felt a sense of excitement and anticipation as she followed Tony.
Tony escorted Y/N to the elevator while explaining that she would mostly be working at her own desk. As they stepped into the elevator, Tony pressed the button to the top floor, leaving Y/N confused and with a twist in her stomach. “The big boss was wanting to meet ya.” Tony informed during the interview that she may never have the opportunity to meet him. The big boss was a mysterious figure who never came down from the top floor. Only Tony and the employees who worked on that floor had ever had the chance to meet him or even catch a glimpse of him.
“I-uh, May I ask why?” Y/N didn't want to seem rude, but she was nowhere ready to meet this man in this vast company, just some little employee. “Think he thought to be a perfect position for a job up there, wanted to talk to you.” Y/N's face widened, and she was utterly stunned when the elevator dinged; Tony escorted them off the elevator, going up to a woman at the front desk.
Y/N was nervous as she stood in front of Tony's office. She laughed nervously and shook her head when Tony suggested she meet Mr. Smith inside. "I- me? I don't think I am qualified for a place up here," she declared, her eyes falling to the younger woman at the desk. “He was pretty adamant about talking to you. Don't doubt yourself.” Tony quickly encouraged her, assuring her that Mr. Smith was interested in talking to her. After a moment of hesitation, Tony instructed the woman sitting at the desk to announce Y/N's arrival to Mr. Smith. The woman exited her seat and greeted Y/N with a warm smile.
“Ms. L/N follow me down this way.” The blonde lady gestured down the longer hallway leading to a tall black door. Y/N heels clicked along with the other ladies, she was beyond confused on why she was up here. She did not feel like she belonged where she was at right now. The lady opened the door for her to enter, Y/N watched behind her as she closed it turning to the man at the desk in the middle of the room.
“Are you fuckin’ with me right now?” Y/N couldn't help herself; she could not believe who sat at that desk. That smirk on his face grew, which drew her in the first place.
Negan was Mr. Smith.
The man from last night.
The man was her fucking boss, and she done fucked him in a night club bathroom.
“Language, is that any way to talk in front of your boss, sweetheart?” Negan questioned, teasing the younger woman. She scoffed with an eye roll, crossing her arms, clearly annoyed with the older male. “You knew, didn't you? The whole time- what, you just fuck all of your employees before they get on the job?” Y/N was furious; she felt like she was fuming. Negan, however, sat in his chair comfortablely with a playful smile and look.
“Wipe that smirk off your fuckin face! God, does it ever go away?” Y/N growled as Negan just chuckled at the younger woman. “You were right; you southside girls are crazy.” Negan stood from his chair, and his appearance was more formal than the last time she had seen him. She shouldn't still find this man attractive; she can not do this with him. But man, didn't he look good in a suit.
“I want to offer you a job up here, doll. I think you'd fit in well.” Negan offered to her, Y/N scoffed shaking her head. “I fit in? You have no idea who I am okay?” Y/N knew this would not be right for her, it felt she fucked her way to the top, “I just got here and your trying to put me up here with a bunch of snooty ass business women who if figured out I fucked you would leave nasty notes and trash on my desk til I quit.”
The young woman stood before Negan, her eyes meeting his as he regarded her with amusement. His gaze seemed to sparkle with a mischievous glow, and she couldn't help but feel a sense of unease. Despite this, she found herself drawn to him, captivated by his magnetic presence. As he pierced his lips and gave her a slight nod, she could sense that he was lost in thought for a moment, considering something important.
"This isn't about that," he said, his voice softening as he moved closer to her. She could feel his breath on her cheek, and her heart began to race. "I'm trying to help you out, sweetheart. You would have your own office, your own space, and more pay. And let's not forget, I would be the one bossin' ya around, doll."
Negan's words were suggestive, and he winked at her with a devilish grin. The young woman tried to hold back a smile, but couldn't help feeling a twinge of anger towards him. It was a struggle for her to maintain her composure in front of him, her mind racing with conflicting emotions. Despite everything, she couldn't deny the attraction she felt towards him, even as she tried to resist his advances.
Negan towered over Y/N, his voice echoing in the quiet room. "Let me offer you this, sweetheart. Stay where you're at for a couple of weeks and see if you want to change your mind, that good?" His words hung in the air, heavy with tension as Y/N met his gaze. She found it difficult to breathe, watching his eyes grow darker by the second. Y/N simply gave him a quick nod, keeping her lips sealed tight. "I told you, doll, I'd see ya again," Negan joked, and Y/N couldn't help but burst out laughing, shaking her head at him. "Come on, you won't even let me take you out on one date?" he asked, a playful grin on his face.
“I can't date Negan; men don't want what my life is, Negan. My life is fuckin’ ridiculous,” Y/N admitted, “I'm still at home raising my siblings like they're my kids. My father, when he comes home, will sometimes be passed out in our kitchen or, even better yet, our fuckin’ yard.” Y/N’s life was nowhere like his life; she saw the tall buildings out behind him. The huge glass windows surrounded his office, which was huge and filled with books and awards.
“Look at your life and mine; it would never work.” Y/N was interested, but she could not bring herself to put himself in this life, her situation, “You could have anybody, Negan, to these people, I am just run down Southside chick.” Negan shook his head, disagreeing with the younger woman. “I don't think that, sweetheart,” Negan addmited, “You're different, that's for sure, but that's what drew me in.” Y/N’s eyes scanned over his for a moment, letting out a laugh rubbing her forehead.
“Fuck it.” Y/N lips instantly shot to his lips, catching him off guard for a moment. He pushed her back closer to his desk keeping his lips locked with hers.
"Sit your ass on my desk." He ordered as he pointed towards his deck. “Here, Now?” Y/N's voice cracked, her nerves settling in. “Don't make me ask again, doll.” Negan's voice was demanding. Y/N didn't question him, so she sat on the cold wood, chilling her spine.
Y/N’s free hand curled a finger into his belt loop and pulled him closer. She wrapped her legs around his hips, gently grinding into his significantly hardened cock in his black pants. “Shit, we need to be quick but not too quick, sweetheart,” he warned, tearing her wandering arm away from him and yanking it behind her back. She chuckled, gently wincing at the roughness, but it crumbled as soon as his lips found her neck.
Y/N’s back instinctively arched and rested on the desk underneath her. She kicked her head back a little to allow him access. Negan was greedy yet smooth, carefully working down to the low neck, ripping off her top. She let him pull her skirt down her hips, his satisfied smirk growing when her panties came into view. The thick pad of his finger found her clit through the thin fabric, slowly circling it. Her hips softly bucked in response as a cry ripped from her throat. Negan took the opportunity to latch onto her bare chest, teeth nipping at a mark he’d already planted.
“Fuck, you’re already so damn wet.” he panted, not wasting another second to slide her panties to the side and run his middle finger teasingly up her soaked cunt. He dipped his fingertip in, watching how she writhed at the sensation. “Fuck me, Negan, please,” Y/N begged, shoving her pride down her throat. He teased her folds with the tip of his dick, her back arching from the desk.
Everything necessary was not her right now; all she wanted was him. “Better fuck me before someone catches us.” Y/N pulled him back down into a kiss, which was rough and sloppy.
Negan snaked his hand to the back of her neck, pulling her deeper into the messy kiss. The feeling of his tongue on Y/N’s and his beard softly scratching her face made her whimper. His other went between her thighs, keeping them wide pushed his dick inside of her. She moaned against his mouth, steadying herself. “Negan,” Y/N’s knuckles turned white from how tightly she held onto his arms, gripping the other hand on the desk.
“Fuck,” Negan cursed when he felt how tight she was, practically squeezing around his cock. Both of them knew it wouldn’t last long, and if they kept knocking on the desk, the wall, and the volume, it would not be long til someone walked in. She could not get caught; they could not get caught.
Y/N would go down, and she would take this man down with her, but they were both consisting of adults. He hooked the backs of her legs underneath his arms and pounded into her, the angle hitting a spot that made her body go completely loose. Y/N’s head slid on the desk under the moans tumbled past her lips.
Negan's thrusts went deep and slowed down so subtly she almost didn’t notice.“That's it, let go, baby.” Negan’s voice rumbled in her ears, nearing a low growl. “You're gonna be mine, baby.” His voice sounded exhausted, chucking in her ear.
Y/N kept telling herself she would end up fucking this all up; she didn't expect to fuck her boss though. And him to actually wanna date her, stay with her. Her breathing was hard to catch up with, cupping his cheek and pulling him into a kiss.
“I'm yours.”