#negansmithauseries

THE YEARLY VACATION I(Part 1)

Summary: Each year Y/N’s parents take their vacation down to Florida for ten days and her dads yearly business trip. This time it’s different though, her dads hot boss Negan Smith is staying with them in their condo for the whole ten days. Y/N’s lustful thoughts that she had always were about to grow into something much more than she ever imagined. More than just them coming true....

Characters: Negan Smith, The Reader, Gracie (OC), Calvin (OC), William L/N (Readers Father), Catherine L/N (Readers Mother), Luke (Calvin’s dad),and Max (Readers Younger Brother).

Warnings: cursing, mentions of sexual relations, age gap (the reader is around 21 or 22 and Negan is in his late 30s to early 40s.), flirting, sexual tension, and slight smut.

A/N: I had to break up day one into two parts since it was over 10,000 words!! This is a very detailed chapter, Part Two will be posted VERY shortly. THIS WILL BE THE ONLY ONE DIVIDED INTO TWO PARTS

PART ONE OF DAY ONE

6:45AM

It was so early, but Y/N was quick out of bed for her shower today. She usually hits her snooze button at least twice, but vacations time were different.

The house was more relaxed in the morning, making the hot water feel much nicer on her skin. Y/N had most of her shower products packed, so she mainly just enjoyed the water. After a while, she retrieved from the shower, pulled the glass door open, she wrapped her thicker towel around her body. The bathroom was steamy, leaving her to wipe her mirror down.

Her hair clipped back, had fallen, letting a few pieces damp from her shower. Y/N kept staring at the woman in the mirror, wondering if she could actually be confident around Negan. Usually, she would feel nervous like butterflies, but she had never been around him for this long before. They would share a condo, pass each other in the condo, be on the beach together, and basically be everywhere this man would be. He would participate in activities with her family, from miniature golfing to playing games at night. She just couldn't let that settle how she'd always be around him until she finally got her own time in her bedroom.

Y/N has yet to see the condo; they get a new condo each year for rent during their vacation. Usually, it was a more excellent condo, like a house separated in a neighborhood. She usually was on the top floor in her own room with her brother across from her. Her mother and father would be downstairs in the master sweet. She knows her brother will be downstairs with her parents in his room this time. So that only meant Y/N would be very close to Negan's room.

Of course…

Y/N kept her damp hair up, putting on some grey sweatpants shorts, just comfortable enough for the airplane ride. She decided to pair it with one of her baggy sweatshirts. Y/N knew the airport would be cold, so she still paired it with a colorful tank underneath.

She finally heard noises coming from downstairs, signaling everyone was finally awake. Y/N knew Negan would be there any minute, too; that's when the struggle would begin.

She got ready rather quickly, having everything packed up and ready to go downstairs. Her suitcase and backpack were filled with clothing and necessities for the long trip. She was all ready to go, her hair done, finally drying off. She cleaned herself up a bit, putting her perfume on; packing the rest of her belongings in her backpack.

"Y/N!" The young woman heard her mother down the stairs call for her, "We all need breakfast; hurry down, my love!" Y/N's mother had called her that for her whole life, which still made her smile. The young woman glanced at herself in the mirror; she looked good. Especially to be in her airport attire. Y/N felt her stomach twist in hunger; it was almost now after 7:30. She knew her dad would have them right out of the house very soon, which meant there was a chance Negan was right downstairs now.

Y/N could not fully grasp what made her so nervous for these days and nights with him. They were good friends when he was around; he was a huge flirt. He couldn't be actually for real, though? She took a huge breath, closed her eyes, telling herself, 'She had this.' This would be a good trip; she did not get to go last year.

This was going to make up for it; Y/N just knew it.

Y/N's feet padded down the stairs, running right into her brother at the bottom. "Woah, bud! Slow down!" Y/N stopped her movements, watching her brother run up the stairs. "I forgot my Switch charger!" Max was quick up the stairs turning the corner to his room; she laughed at her younger brother; he was quite the character.

Y/N had a natural bond with her brother; they were really close. He would stay with her some nights when she moved out with Calvin. He had his own little spot on the pull-out couch in the extra bedroom little gaming setup too. The whole family had a lovely bond; her family was in a good place. Y/N and her mother loved going shopping together and grabbing a bite to eat at their local favorite restaurant. Of course, sharing gossip about anything they had their hands on, there was some juicy stuff to in the upper community. She would help her some mornings with breakfast and ride to school with her dad singing the old eighties hits.

William adored his family, and he spoiled his family. He didn't do it to buy their love; he did it out of love. William started out as an intern in the business, working on trying to get him and Catherine married. They lived in a one-bedroom apartment when Y/N was born; they made the best of it. Some nights William would work longer and more complex hours, but it all became worth it in the end. He got to be everything he could for his family, even though he did get the children spoiled.

Y/N had to have her own way most of the time; she was a brat at times. You can not honestly help how you've raised them sometimes, but she was very respectful towards her parents for it, at least when she got more mature.

She turned into the kitchen, seeing Negan with a cup of coffee. She couldn't help but absorb his features. His black glasses tipped down his nose, and he wore an old band tee. Y/N could barely see the Guns N Roses logo from the wear on the black tee. She let out a quiet gasp but caught her mother's attention.

"Ah! There you are!" Her mother rushed to her giving her plate, "Your father is already packing the travel vans out there." Catherine chuckled at her husband, causing her daughter to snicker. Y/N's eyes peered over, watching Negan's eyes on her sipping his coffee.

She knew he had a smirk under that glass and turned her attention back to her mother; she looked suitable for her age. Catherine's smile brightened her whole face.

Her mother was an angel; she did most of the cooking and cleaning. They did have a housekeeper Nina who's been with them since Y/N was eight.

Her mother continued.

"Sweetheart, grab a plate. Fix what you like! Nina coming by later to clean, so just put the dishes in the dishwasher!" Catherine moved past her daughter out of the kitchen, having her alone with Negan.

"Well, there she is!" Y/N let out a small laugh shaking her head and heading her blush. She moved, seeing the feast her mother had cooked for them; she felt awful but couldn't dig into it all. Y/N always stuck with her bread and jam and eggs. She started fixing her breakfast, leaving her ears open for Negan.

He was always so full of things to say.

He moved up from his seat, revealing he was in sweatpants, and he kept sipping his coffee. "How have you been, doll?" The nickname sent chills down her spine, biting into her toast. "I've been good, finals were awful, but I passed." She smiled softly, holding her hand over her mouth and covering her mouth, "How about you, doll?" She threw back at him, causing a deep chuckle from Negan, moving his glass to the dishwasher.

"Oh, you know me. Busy as a bee." Negan leaned against the counter, crossing his arms. His tattoos peaked out of his shirt sleeves, the cross of his arms showing his tonearms. The tattoos ran down his arms, and Y/N kept eating, trying to focus; she wanted to hit herself, "It's going to be a great little trip, ya know?" The young woman gulped her food, watching the man shoot her a playful wink.

Her cheeks turned pink, hearing her father and mother enter the kitchen behind her. "Alright, we need to get this show on the road," Her father said, coming up to his daughter, still kissing her forehead, "Good morning, sweetheart. Do you have everything?"

"Yes, Dad, I am as ready as you are." She playfully rolled her eyes at her dad, throwing her dish in the dishwasher. "We have our first dinner tonight at 8PM!" Her father started to lock the back doors around them, shutting the blinds on their open windows, "Once we land and settle in, you girls will have to do some shopping!" Her father pointed his finger at the women like he was scolding them, causing a laugh from both.

Each year when they arrived, they had to do the "annual shopping trip," her mother called it. There were three "dinners" or "parties" throughout the ten days of being down there. The first was the welcome of every part of the company; the highest people in the company would meet down in Florida. The first dinner was usually at a fancy hotel, and dinner was usually catered. The second dinner was the main event on the eighth day. The place changed each year. It usually started around mid-afternoon, which that night was the third event; the after-party.

The less fancy..party.

The annual shopping trip meant dresses for every three parties. They would also get what they wanted today while shopping; the boys usually hung around playing the arcade shopping for Max games. Of course, Max and William had their outfits ready for each party; imagine taking a twelve-year-old boy for a fitting tux on vacation.

Yeah, not the brightest idea. Still was hard to do back home.

"That's my time with my Y/N; how would I forget." Y/N felt a little embarrassed, but her mother meant well. "Mother, please." She said through her bright smile, hearing Max's feet flee down the stairs. She kept wanting to shift back over to Negan to see if he was looking at her.

Y/N bit the inside of her mouth, letting her thoughts wander for a brief moment.

It was broken quickly by her younger brother.

"I found it," Max held up the charger, breathing fast, trying to catch his breath, and throwing it into his backpack.

"Alright, make sure you guys have everything and head to the car; the drivers have our stuff in the cars!" William instructed his family; Y/N knew she needed one more thing before she left.

Something she had always grabbed before the vacation since she was sixteen.

One of her old friends taught her how to get away with it for so long; a little risky, but who her father was, she felt safe.

"I'll be there just a second, Dad. I'm gonna run to the bathroom!" She headed for her room, hearing her dad telling her to be quick; Y/N quickly moved to her room, pushing it cracked.

Inside her vanity, a black box was found. It was metal, keeping the rolled-up blunts she had for the trip.

Y/N never hardly smoked marijuana, primarily through her late high school and college years. She stopped for a while just doing it during her vacations; it was relaxing sometimes.

It was easier to hide each year, keeping the black box in her makeup bag attached to her backpack. Usually, security scanned all of them through since each year they all went; it was more accessible than ever now. Y/N heard her door crack, which made her jump throwing it down into her bag.

She turned quickly, seeing the tall man in front of her; he eyed her keeping his smirk to himself. "Your dad is killin' me out there," Negan laughed, seeing her shorts ride up; on her knees, "You doing more than just using the bathroom?"

"It's none of your business," Y/N playfully replied, standing onto her feet and zipping it up her bag, "Maybe women's things." Negan snorted out a laugh, shaking his head at the young woman.

His hands tucked into the pockets of his sweatpants, leaning against her bedroom door, eyeing her room down.

"Cute."

Y/N playfully rolled her eyes, pushing him out of her room; shutting the door behind her. "Cut it out you ass!" Negan laughed at her playful push; they always nonchalantly flirted.

I mean, wouldn't you?

He was so fucking hot; Y/N didn't care if he was her father's age. She had a tiny crush on the older man; she also had to remember that it couldn't happen.

But at the same time, she wanted just to see, maybe.

It wouldn't hurt.

Y/N kept a gaze on her dad's boss for a moment, her hands still on his arm. The young woman realized pulling back from him was not too fast for him to notice her nervous actions. "I-uh-.." Y/N felt like she was in high school again; she couldn't even talk to a man, "We need to get going." She quickly smiled at Negan; he stayed in place for a moment. Which twisted up her stomach with butterflies, wondering about his next move.

Realizing how close he actually was to her.

Negan cleared his throat; he knew what he wanted. It was her. She had been seeing him for years; she was always beautiful. When he didn't see her for her eighteen and nineteen years, she changed so much at twenty.

She was absolutely stunning, with perfect curves. An ideal woman's body was a sight for sore eyes. Y/N was also easy to talk to; she had a boyfriend over those years.

Negan hated the jealousy he had; he couldn't help but ball his fist seeing his hands on her during that one trip. Negan knew Calvin's family, his dad, Luke, was a part of the business down in Gregoria. That's why Y/N moved down with Calvin to Georgia; he had a perfect job opportunity with his dad waiting.

Luke was over the company down in Georgia; Calvin was an only child. Negan always found him a man who wouldn't treat a woman right. His father wasn't much more different than that either; he cheated on his wife numerous times. She stayed honestly, probably for the money, acting like nothing had happened.

He knew Y/N and Calvin was not together anymore; he never knew the reason. He knows Y/N didn't go last year because of Calvin.

Negan missed her that year.

"Lead the way, Ms. L/N." Negan motioned for her to go first, and the butterflies slowly disappeared in her stomach with relief but also disappointment.

The two got into the cars leading them to the national airport in Chicago. It was a one-flight ticket down to Florida, about a three-hour flight to Miami. Three hours elbow to elbow with Negan.

When they arrived, the two drivers escorted them out of the vehicle; Y/N's sunglasses rested on the edge of her nose watching the men roll their luggage away to be put on the plane.

She was very used to planes, but they still made her nervous for the takeoff, which was the roughest for her. "Okay, dolls," her mother turned to her family, "Our terminal is 5. Have your tickets ready; they should just scan us through security."

"Looks like I'm sitting with you, sweetheart," Negan stood beside Y/N; she placed her glasses on her head. "Oh, I didn't notice." She poked her bottom lip out, pretending to reread her ticket; NeganNegan's lips curled up, snickering at her.

That was his friend and also co worker's daughter. He had to remind himself that at times, but something kept drawing him in. "Hm, it seems you are," Y/N glanced over at his ticket, "I bet you're so excited."

"You have no idea, baby." Y/N quickly heard him whisper under his breath, and her face went bright red.

Maybe she didn't hear him right; perhaps she was delusional.

"What?" Y/N quickly choked out; Negan knew he could get to her. "I said you have no idea! You're my buddy, right?" Negan raised his eyebrow smirking at her; her face was still red.

"Yeah, best of friends." She muttered softly, following her parents inside the airport doors. She must have heard him wrong; he would not call her baby. Especially her family feet away.

They were quickly escorted through security, heading to their terminal.

See easy..

The airport was busy; it was always busy this time of year and especially Christmas. They boarded the plane not long before, first in line heading to the aircraft's upper.

"Alright, sweetheart, you want the window seat?" Negan asked her, the two staring at their seats. They were three seats down from their parents. She knew she would need a drink for this trip, no matter how early it was.

"I would not mind the window seat; I mostly will be reading." Y/N wiggled her book up from her backpack, squeezing in to take her seat. Negan took the seat beside her, causing a chill down her spine. His arm grazed hers, setting her bag down below her legs. "What? Are you reading one of those sex books?" Negan leaned over and quietly whispered playfully to her; Y/N's face squinted with a giggle.

"Every good book has a few steamy scenes." She shrugged, piercing her lips to hide her blushing smile. Y/N started buckling herself up, and when going to make it tighter, the band was stuck. She pulled harder, fighting with the belt around her waist.

"Do you need help with that?" Negan teased; she just kept pulling the belt.

These stupid damn belts.

Negan's hands went to her waist, instantly pulling it tighter. Her hands were not far from his, and Y/N was not totally caught off guard by his help. "Thanks." Negan's arms returned to resting on the armrests, and Y/N tried to start her book. She kept observing the first chapter of her new book, You Shouldn't Have Come Here. She still could feel his arms close to her own, giving her the butterflies once more boiling in her stomach. How was being close to him making it feel like she had never been touched? How could he have this much of an effect on her?

"You like the reading thing, huh?" Negan pondered on Y/N and bit her lip, breathing out a laugh. "The reading thing?" The young woman questioned his wording, "That is what you call it?" Negan shrugged, his mouth curling up into a smile.

"Yes, I am into the reading thing, now shush." She gestured with her hand with a 'shush.' Finally, actually trying to start her book, turning to the next page.

"What am I supposed to do?" Negan broke out; her gaze moved from the words to his eyes. God, that beard made that man attractive; she wondered how he looked with no beard. "Maybe you should get into the reading thing," Y/N suggested, keeping her book between her fingers closed. "I have other things for my hobbies, doll." Negan eyes observed her own, moving down to her hands where she nervously dug into her sleeves.

Negan thought she looked cute; she was not wearing the usual revealing dresses. He knew those nights would come. Y/N always looked stunning during those events; her body showed through each dress. Each one always complimented her curves; red especially was her color.

Y/N tried to keep quiet, only answering Negan's random questions, most of which made her laugh. She was getting deeper into the book and the plane ride. They were finally served refreshments; she was on her second Memosia for the day. Negan ordered a glass of whiskey on the rocks, still sipping his first glass.

Y/N knew she was nervous; she needed adrenaline to kick in; or the alcohol. Negan would joke about how she would be stumbling off the plane; Y/N knew she was pretty good with alcohol.

Most of the time.

Y/N also could have sworn she felt Negan's fingers graze hers sometimes; she kept her eyes on the words. She could not help but peer over sometimes, seeing if he was any closer. Sometimes it was hard to tell, but Y/N felt like he was closer to her than the first hour of the flight.

Finally, the words were music to her ears, and they were finally landing after three hours. Y/N glued her eyes on the outside, watching them get closer to the ground. "What are you most excited about the trip, doll?" Negan asked the younger woman; the plane shook slightly while the wheels rolled finally onto the ground.

"I always love the nights on the beach, even from the condo. Hearing the waves on the deck is nice enough." She admitted to Negan their conversations had been casual. He would shoot her a few questions here and there just to be able to talk to her. Negan just wanted to tease her; he loved watching her squirm, especially when she tried to hide it.

The pilot finally announced for them to depart from the plane exiting the terminal; Y/N saw her little brother waiting there for them. "You're so lucky you got to sit in first class; I had to sit beside this old man!" Max cringed, talking to his older sister while they waited on their parents.

"Well, I had to sit by an old man too." Y/N teased the man beside her, his face filled with a smile, but he pretended to be hurt by her comment holding his chest. "Man, sweetheart, breaking my heart." He put his own carry-own around his shoulders.

"There's mom and dad!" Max ran up to them just like they had been gone themselves on vacation. "Hey! How was it for you guys?" William wondered out loud to the others, wrapping his arms around his wife and son. "It was fine, Dad. I had a couple of drinks to keep me calm." Y/N grinned, "I guess I had pretty good company too." She motioned off to Negan.

"I had to sit beside an old man with long ear hair!" Max cringed once more, causing a laugh from everyone. Her fathers glanced over the information for them in his emails.

"I got us two cars for rent, sitting outside in parking spots 2A and 2B." Her father pointed at the map for everyone to see, "If you guys get the luggage, Me and Negan will get help to move cars around."

"Sounds good, man," Negan replied, hitting the back of his shoulder friendly, "We will see you guys soon." Negan turned to where Y/N saw his wink, following her dad. Her face couldn't help but beam red with a blush.

She loathed this man.

Not really, just his actions, his looks, his face…

He knew what he was doing; he had to, right? Y/N knew he wouldn't act like this, right? She literally let the anxiety and overthinking get to her.

"Come on, my loves, we have to go downstairs." Catherine grabbed Max's hand, and Y/N followed behind her mother and brother. The airport was crowded, she stayed close as possible. No matter how often they have been here, she still would get lost.

They made it to the escalator, escorting them down the stairs where each gate was for suitcases. "Remember, terminal five was ours." Catherine reminded her children, leading them off to where their luggage would be. One by one, they got their suitcases, along with Williams and Negan's.

Y/N noticed he just had a small carry-on, along with the bag he had with him now. Her luggage was half the size of his, probably everyone's luggage, to be honest. She could barely get it off the floor.

Negan and William found them beside their terminal exit arriving with a luggage carrier. Negan would be driving the black SUV to the condo while Y/N's family would operate in the red SUV. Her father would get two vehicles each year, especially since Y/N started to drive.

Y/N was so excited to see the condo; they always were so beautiful and secluded.

It was mid-afternoon. It was sunny out and extremely hot outside. This caused Y/N in the car to remove her sweatshirt; she was ready for a shower before going shopping. Getting into a new change of clothes sounded lovely, too; Y/N was glad she packed so much.

When they arrived at the condo, pulling up the long driveway, the gate let them in with the code. It was the most beautiful yet.

It was all white with wooding boarding on the sides. Lights hung on the front porch, bunch of cute chairs were very welcoming. From what she could see, the top floor had a whole round of a deck for them to watch the ocean behind them. The size was big, seeing a pool off to the side when pulling into the garage.

"Max doll, your room is right from ours," Catherine said, knowing Max was the first out of the car, running to his room to set up his games. They were quick out of the car, running to the door, "Alright, Y/N love, your room is left on top."

Y/N got out slowly, seeing Negan getting his stuff out of the car behind them. She held her sweatshirt close going inside where the kitchen was. It was a kitchen that reminded her of back home, very modern. The stairs were towards the front door, which was solid black.

She followed up the stairs turning left, seeing an open room filled with sunlight. Y/N entered the room; her bed had thick white sheets. Filled with bunches of pillows, mostly beach themed.

Beside the bed complimented wooden bed rests with shell-shaped lamps. The closest was beside the bed, still covered by the fuzzy rug underneath the bed. Beside the closet was a door to a master-size bathroom containing a walk-in shower.

The bed was pretty big, she guessed, a king, and the windows were wide big, letting her see the deck she had outside. There was a flat-screen above the full dresser in front of her bed.

After glancing over her room, she jumped on the bed, feeling herself sink in. She hummed slightly, closing her eyes and absorbing the comfort of the room. "You pack this much stuff and just gonna lay in bed?" She heard a playful grunt come from the hallway; Y/N sat up, sitting Negan placed her suitcase in her room, huffing out. She giggled, watching his hands sit on his hips. "You seem to have it." Y/N snickered, Negan rolling his eyes at the spoiled girl.

"Your daddy got you spoiled, huh?"

"Just a little." Y/N stood up, rolling it over to her closet, "I'm not as bad as Max." Negan stepped further into her room, gazing over her room. "By the looks of this room, sweetheart, you're the most spoilt." Negan chuckled, sitting on her bed; Y/N tried to swat him away with her hands.

"You're going to stink up my sheets with your sweaty self." Y/N laughed while Negan blocked her playful slaps to move. "Oh, you don't think you stink after the long trip?" Negan watched the young woman give up, sitting beside him on the edge of the bed.

"No, I'm not the one was is wagging in luggage," Y/N smirked; she was leaning over, letting the tank reveal some of her cleavage. Negan's eyes tried to keep a gaze on her, letting his eyes wander back up. Her smirk seemed more seductive like she caught him looking at her chest.

Negan's mouth parted, not knowing a word to say. This wasn't their first-time inches apart today, but they were on a bed. "Don't you have more to help with downstairs?" Y/N mumbled; she pulled her bottom lip between her teeth.

"Huh-uh-yeah," his eyes still locked with hers, answering her question, "Your dad probably wondering where I'm at." Negan rubbed the back of his neck, for his nerves were getting the best of him. He stood from the bed, leaving Y/N sitting alone. Negan stood in his spot for a moment in the room.

"Yeah, don't want daddy seeing you in here." She said seductively, gazing over at Negan and watching him walk out. His face was red; he felt like he could feel the sweat drip down his forehead.

Y/N watched the older man leave, feeling the confidence sentence turn embarrassing; maybe she should not have said that. She covered her face, falling on the bed. She knew her parents would be ready soon to return to the shopping area, so they could be back in time to all get ready for the big dinner tonight at 8PM. Y/N gathered herself, finally getting up, going over to her suitcase, and hanging her clothes up. She had anything from comfy attire to cute little sundresses for days and nights out.

After getting her clothes into her closet, Y/N laid out a pair of blue jean shorts and a tied-up Hawaii-themed shirt to shop today. She desperately needed a shower, so she shut the door to her own bathroom, toiletries in hand.

All she could think of starting her shower was Negan. How tense it was becoming with him, how his attractiveness had grown.

The water was scolding hot, hitting her skin. Keeping her hair up still from not getting wet, she let herself relax there for a moment. Steam started to collect around the room, covering the glass around her. Maybe Negan was not attracted to her like she was to him? Or maybe Negan was too scared of what would happen if they messed around?

Maybe he was just a tease.

But what was Y/N?

A fucking tease as well.