THE YEARLY VACATION I (Part 2)
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), Samantha (OC), Tina (OC), 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: HELLO! Another over 5,000-word chapter. Oh well, I did feel like I had to rush a few things, but Day two and others should not be like it. Day One is always the hardest, right? NOT FULLY EDITED!
PART TWO OF DAY ONE
Y/N stared into the mirror on her third attempt to tie her slip-on shirt. Y/N groaned to herself, finally getting the perfect tie and letting some of it hang down. It was securely tight on her; the flowy sleeves were a little longer but thin enough for the heat. She twisted her hair locks up into a clip, went into her room, and gathered her purse together to head out for shopping.
She heard her mother call her name for the third time down the stairs, and she groaned at their time schedule. Her father always had to be early to an event, right on time for everything. Her mother always had to keep the same time schedule each year, rest for an hour, then go straight out."Coming, Mother!" She called out, grabbing her sunglasses from the dresser and heading out of her room, seeing Negan exit his room across from her.
"You coming on the annual shopping trip as well?" Y/N noticed his new change of clothing, his black top buttoned up to the last two. His grey sweatpants changed into jeans, still a casual look. His laugh sent a ripple that vibrated to her area, making her toes curl in her shoes. "Yeah, your old man said the mall has a great bar,"
Negan rolled the cuffs of his sleeve up, walking past the younger woman, "We will sit and drink while you use daddy's credit card." Y/N's lips started to pierce with a smirk; she bit the inside of her mouth to stop her laughter. "No, I will use my mother's credit card, Daddy's money." Y/N slipped her sunglasses on, not watching how Negan was eyeing her. The way his lips were brought between his teeth, she had no idea what she did to him.
He wanted to be the one to spoil her, pamper her with everything she could have wanted. Negan knew he could care for her much more than the boys she had been with. The two headed down the stairs, where her family waited for them to head out to the mall. The mall was a huge walk around; all the stores were outside, like an outlet mall."Your father agreed this year to help me pick out some dresses; he agreed to one shop, thankfully." Catherine tried every year to get her husband to go in that dress shop; Y/N could not help but think how her mother brought her father to do such a thing.
He hated shopping.
Y/N's father did not care how much money they spent; he even loved seeing what they bought, but his motto was, 'Do not bring him with you; leave him at the bar.' "Negan, you can chill at the bar if you'd like," William knew his boss probably did not want to shop either, offering him a better solution, "Or when we drop Max off at the arcade. I'll come meet ya' there. Me and Max shoot some hoops for a while."
William rubbed the top of his son's head, messing up his hair a little. Negan chuckled; he couldn't believe how perfect this could be. "Nah, man, it's fine. I'll stick with you there till the girls are done," Y/N could not believe her ears; Negan was going to be with them while they shopped, "Hell, I can pick out some good dresses." Negan's joke made everyone laugh but Y/N as his eyes peered over at her, keeping the smirk plastered on his face. Negan followed behind William's family to the mall. It was about mid-afternoon in Florida; the mall was not as busy as it could be but still covered with people. Y/N felt the whole way; he kept playing a game with this situation.
What if he just did not care, though, just stuck around for the hell of it?
When they arrived at the mall, William stopped by the arcade, dropping off Max with some cash parking near the area of the dress shop. Each year, they went to the same one; Catherine was well-known there, especially with her daughter Y/N. The four entered the shop, letting Negan hold the door for them all. Y/N was the last one to enter; she could have sworn when Negan was behind her, his fingertips brushed the bottom of her back. She could not even react to hearing her mother greet the employers.
"There are my girls, look who actually came to help." Catherine hugged the two older women around the front desk, showing off her husband, "If you could start a dressing room for me and my Y/N." Y/N smiled at the two older women, sisters running the shop locally. They had endless dresses, anywhere from prom dresses, party events, formal events, and wedding dresses. Samantha was the older sister who mainly designed the dresses, a little older than her parents. Tina was her younger sister, just right about her parent's age. The two, in a way, watched Y/N grow up.
"Oh my, there is our girl." Tina smiled, hugging Y/N. She knew they probably missed her last year, "You're growing into a fine woman." She playfully winked, Y/N filled with a compliment but, in a way, embarrassment. "We will get you two fitting rooms, dear." Samantha smiled, heading to the back way to the dressing rooms. Tina pulled Y/N away to a bunch of isles of rather colorful dresses. "These are some of the newest; look this black." Tina pulled out a plunging black dress. It was elegantly long, with a cut up the leg. It was a very tight-fitting dress with ties complimenting the back area. It was about perfect for one of the nights.
"Do not try to win me over with the first dress; I'll buy out your whole shop." Y/N snickered, glancing over to see everyone gone from the front of the store. She knew Negan was probably following her father like a lost puppy in this dress shop; she hated it, but she wished he would help her pick a dress.
Maybe a dress to fuck her in… way too overthinking it all.
Y/N's fingers rolled over the plastic protecting the dress; she knew that was one she had to try on. "Pull it." Tina smiled at Y/N, taking the dress to her dressing room and letting Y/N continue shopping. Her fingers went through most dresses, none calling her like the first one. Y/N still needed one more elegant dress; the party dress was easier to pick. She was pretty picky with dresses, clothing specifically.
“Your mother is already on her fifth dress, and you’re still looking?" Y/N heard Negan's deep voice echo behind her; she shrugged, keeping her eyes on the dresses. "What can I say? I am a very picky woman." His voice was deep, and his presence made the air seem thicker around her. The hangers clicked with the silence between the two; all the dresses seemed too plain for Y/N. "Is that just in dresses?" Standing beside her and going through the dresses, he seemed calm with the question. "I can be picky with other things," Y/N mumbled, moving to the other rack. Y/N watched Negan like he was actually paying attention to each one.
Maybe admiring her in each one.
"What about this red one?" Negan pulled, and Y/N pivoted her head toward the older man. Instantly, the dress caught her eye; the brighter red dress was more extended and elegant, just like the black. The red also had a slit but with ruffles all the way up the leg.
It was beautiful.
"Maybe you can pick out a dress." Red was her absolute favorite color; it complimented her well. Negan smiled, handing her the dress for her eyes to scan. "Don't you think my parents will find it weird that you helped me pick this dress?" Y/N wondered, adding a little amusement to her voice; she tried not to bite her lip, eyeing the red dress, "Don't you know what red can stand for?"
"They won't know, doll." He called her 'doll' and 'sweetheart' so much more different than how her parents called her. Hearing him say Negan knew the nicknames got to her was satisfying. He wished Y/N would say to him the way she said, Daddy.
Just her voice sometimes would make his dick twitch.
Y/N looked around, ensuring no one could see them down the tight isles around them, keeping them close together. "What? Do you want to help me try it on?" The younger woman bravely asked. Negan's face was pure red, but his lips turned into a smile. It seemed she could be joking with the tone of her voice, but her face spoke otherwise.
Her movements.
"Your parents are going to be right beside us, Y/N." Negan seemed a little flustered; he was turned on by her confidence. He hated that he could not try and make the first move on her. She let her eyes trail over his features, down his body. He seemed to have such a nice body under all those clothes he always wore. How his tattoos would peak out, his veins trailing down his arms.
Negan was definitely intimidating.
"So.." Y/N paused, stepping closer to the man, "You agree you'd want to help me?" Y/N bit her lip in curiosity; maybe she knew he wanted her. Perhaps it was just wanting her to hear him say it out loud. Negan's mind wandered off momentarily, wondering how honest he should be with her. He knew he had ten days with her, ten days to be with her in any way possible he could want.
"I could help you with anything you want, darling." His reply made her feel weak to her knees without even a touch from her. Y/N felt like she could not breathe, feeling the air thick again. She shifted in her spot, clinging to the plastic around the dress. Y/N let her eyes wander around her, ensuring the coast was clear of her parents.
"We better not do this here, Negan." She tried to walk past him, but he grabbed her wrist and stopped her. Y/N's eyes shot up to his own eyes; he looked down at the face he was lusting over. She felt herself tingle down in her area from his touch; the grab was not aggressive but enough to make her heart pound,
She could not believe it was turning it on.
"My parents, Negan," Y/N spoke once again; she felt herself trying not to pounce on him right then and there. All this sexual tension was building up into so much more. His grip became a little lighter on her wrist, and his eyes never once moved from her E/C eyes. "Get to trying on some dresses, doll." He moved away from her, and Y/N felt glued to the floor.
There was no way this could be real; she must have fallen asleep on the plane. Y/N finally gathered herself, moving from the floor to find more dresses. She knew she would not like some but needed to get to a dressing room. Maybe she can gather her nerves to prepare for a long night at a classical music party tonight. Y/N also knew Calvin would be there, along with his own family. She would have to face him again, along with having the man beside her she wanted to fuck till the end of the night each night.
Y/N walked near another hall of dressing rooms, closing it rather quickly, seeing her black dress hanging there waiting for her from Tina. She leaned against the door, clenching the dresses close to her. She just breathed out, trying to make herself try on the hundreds of dresses she had clenched in her hands. Hanging one by one up on the rods poking out of the wall, she decided to try on her party dresses first.
First, she had a blue that was relatively shorter on her, maybe too short. Y/N noticed, turning around, how her ass almost poked out of the bottom; not only would her father kill her. The way Negan was being, he might kill her. She could not help but want Negan to be jealous of her, like her all to himself.
Y/N was quickly unchanged, leaving her topless with black lace undies. She didn't wear a bra with her outfit; none of her bras went with it. She also knew she did not need one to try on the dresses. She threw the blue dress back on the hanger, grabbing the longer white dress. It was a brighter white, a bit longer than the blue, a few inches above her knees. Her hands rubbed the sides of her curves, the dress complimented in each way. Sometimes, the way she moved the dress would sparkle with the light, causing her to smile, feeling like a princess again when she was little.
She knew it was perfect for the after party, not too much of a party dress like the blue. Y/N put it aside for the first dress she wanted to keep; her eyes kept fixating on the red Negan picked out for her.
She did not care how it looked; she just wanted to buy it because he picked it out for her. Still, Y/N had to know what it looked like on her. She quickly took it off the hanger, covering her half-naked body. She watched the red dress slip over her body like it was made just for her.
The ruffles made the dress so cute.
It was so soft; it felt like she was wearing nothing. Y/N smirked mischievously to herself in the mirror, knowing how perfect it would be for the first night tonight. She did not even have time to hear the dressing room door open behind her; she quickly reached to try and shut it, realizing it was Negan.
Y/N gasped as he locked the door behind them, placing his finger on her lips to keep her quiet. "Ssh, your parents are close." He whispered; she was utterly stunned to even speak. She felt him push her against the mirror behind them; they barely had room in the tiny box of a fitting room. She could feel the dress slipping off from her, starting to take it off before Negan entered.
"Leaving the dressing room unlocked, naughty girl." His breath was near her neck, breathing down. Y/N closed her legs to keep the pressure down her legs at ease. She clinged onto the ends of her dress nervously. The younger woman was still at a loss for words, her head resting against the mirror. His thumb rubbed over her lips, moving his eyes down to her more exposed chest. Negan could not hold himself back; he wanted the entire ten days with her.
"Tell me, sweetheart," Negan whispered, his thumb dragging her bottom lip down.
God, she was so hot.
The way the dress was hanging loosely around her, the red complimenting her so well. She looked so submissively at him the way he had her pressed against the mirror. Her knees felt like Jell-O, and she shrunk underneath his touch.
"Do you want me?"
Y/N thought she could get Negan to admit first, but she was about to give in to what she had wanted for years. She tried to gather her words together; her pride wanted to get the best of her.
"Do you want me?" Y/N fired back; his lips were relatively close to her own. His fingers rested on the bottom of her chin to keep her looking up at him. "I have a proposition." The older man murmured, her nails digging into the dress's ends, "We have ten days together, and it seems we both wanted this awhile."
She kept quiet, letting the man speak before her, who had her pinned against the mirror.
"I say we fuck every day until we get off that plane back at home," He came closer to her lips, his hands cupping the top of her throat. Negan causally laughed, resting his forehead on hers, "Excuse me for being so blunt, darling." Y/N let her hands travel to the open buttons of his shirt, starting to pop the first one not opened. His eyes watched her hands, giving a deep, dark chuckle to her actions.
"I did not say fuck right now, sweetheart." Y/N groaned softly at the man's words; she wanted him to press her against this mirror. Wrap her legs around his waist, and let him fuck her like there is no tomorrow, "It's just too risky, baby." It may be too risky for sex, but Y/N knew it would not kill them to kiss him. She cupped his cheeks, bringing her to his lips; Negan could taste her lips gloss, rubbing his tongue against her bottom lip. "God, you better get this dress doll so I can rip it off of you tonight," Y/N moaned against his lips quietly, her hands all over his clothed body. "But it's a gorgeous dress." She whined, not that Y/N would not love for him to tear it off of her like a wild animal.
"I can buy you a thousand more like it; let's wait for tonight." Negan's full grip was now completely around her throat. Negan pushed her head to where her neck was exposed; all she could see was some of his face in the mirror behind her. "I want you all the ten days," Y/N admitted, turning her head back to look her in the eyes. Y/N kept her legs squeezed together, feeling a pool between her legs forming.
"Check to see if it's good for me to walk out, doll," Negan smirked, "Don't want to get caught on the first day." He pecked the tip of her nose, letting go of her neck. Y/N held her dress with one hand, feeling exposed, opening the door slightly to see her mother and father turning the corner with dresses in hand.
"You should be good.." She mumbled, moving out of his way for him to exit. Right before leaving, he clicked the dressing room door locked. "Make sure not to lock your door tonight, doll." He winked, closing the door shut, locking her in whenever she was ready to exit. She turned to the mirror where smudges formed from her body against it. Y/N noticed her lips swollen; her lip gloss glistened on her chin. The back of her hair stood a little like she had sex with him. She ached for him; she hated how he left her here in this state. It was going to be a very long night.
Hours Later...
Y/N dug through the jewelry she had backed up in her little pink box; she found the diamond earrings her father had bought wrapped up perfectly broken.
They were a gift to her for her sweet sixteenth birthday.
She could have sworn she packed them in a zip-up perfectly for nothing to happen to them.
"Sweetheart, it's okay." She sat beside her daughter on the bed, who was upset. Catherine wore a darker navy blue dress wrapped with a blue silk drape around her. She sat beside her daughter on the bed, who was upset. "I feel dumb being this sad over earrings," Y/N laughed at herself; she was already dressed. Her makeup was done nicely, a little. She complimented the red dress with lighter lipstick. Her hair was curled, lying down above her exposed chest.
"They were special honey to you; I remember when I first lost my bracelet your father gave me." Her mother laughed, wrapping her arm around her daughter, "I was so upset that I cried; it was the first thing your father ever bought me."
Y/N had the matching necklace of the earrings around her neck; she just felt so empty without them. "How about I go grab a pair of mine to borrow?" Catherine smiled at her daughter, closing the pink box for her daughter, "I have the perfect ones to go with the necklace." Y/N smiled, letting her mother go off downstairs for her own pair. They were beautiful earrings, just like her father got her; they were a little shorter than hers but complimented her well.
Y/N is up close in the mirror in her own room, fixing the earrings in her ears, her mother behind her, trying the rest of her dress. "It's a beautiful dress, honey." Her mother complimented her daughter, playing with the curls of her hair, "Tina, pick it out?" Y/N looked down for a moment, knowing the truth of who picked it out for her. What happened when she tried it on in that dressing room? A lump formed in her throat, trying not to think about the kiss that Negan and her shared.
"Yeah, she helped me mostly." Y/N cleared her throat, eyeing her appearance in the mirror, "I'll meet you out there, Mom. Grace gonna want pictures." Catherine laughed at the girls, shaking her head, "We will be downstairs, baby. You look beautiful." She kissed her daughter's forehead, heading out of the room, leaving the door cracked.
Y/N snapped pictures of each angle of the dress she could send to Gracie quickly, seeing the images delivered and walking down the stairs. Her mother was waiting down the stairs, with the boys outside getting the cars ready. Y/N was nervous walking outside, seeing Negan leaning against the car and talking to her dad and brother. His words just kept singing in her mind from this afternoon. She knew he wanted her, and he knew that she wanted him. Y/N felt like she would be eye fucking him all night, hoping her parents and others would stay oblivious to it all.
She was going to need lots and lots of champagne.
"Well, don't my two girls look gorgeous?" William complimented the woman, wrapping his arms around his wife and kissing her cheek.
"Finally ready; took you long enough." Max groaned, putting his black jacket around him, "Y/N is always the last to be ready." The young woman playfully pushed her brother; he loved teasing his older sister.
"You girls, do you look great tonight." Negan came up, complimenting both ladies, shifting his eyes to Y/N. She stood tall in her black heels with the dress he picked. The dress was gorgeous on her; Negan knew he could not keep his eyes long on her here, "I'll let you guys follow me." Negan headed to get the first car, walking past Y/N, fighting his gaze with her eyes.
He looked so hot in his black pants and white button-up; he had the long black tie, a few buttons open still. He kept his jacket in his hand, probably from the heat; his cuffs rolled up halfway up his arms.
Why was everything about him so sexy?
"Alright, load the car up!" Her father opened the passenger and back doors for his wife and children.
When arriving at the party, valets were waiting to park their cars. The hotel was massive outside of Miami. Lights lit up the streets; people were dressed up all around them. Inside was a fancy check-in area; the staircase was huge and bought out for the event. Most of the people attending these parties stayed at this hotel, but her father wanted more privacy.
Y/N's heels clicked into the hotel's party room; it was huge, just like a ballroom. Negan could organize a party well; he hired good planners for each one. She knew Negan would be off talking to basically everyone there; he was the host of the party, the boss. Y/N quickly walked over to a table and grabbed a tall glass of champagne, her nerves getting the best of her. She barely knew anyone there, and Y/N always stayed quiet, usually at these events. "Y/N?"
She heard behind her; Y/N's stomach dropped, hearing that familiar voice behind her as she sipped her drink.
"Cal."
She turned to see her ex-boyfriend, hands in his pockets; Calvin smiled like he had never done anything wrong. "You look great." Y/N scoffed slightly at his comment, chugging the rest of her drink, already grabbing another glass. "I wish I could say the same." Her hands gripping the mirror more, her eyes searching her for parents, even Negan. Calvin chuckled at the young woman, going by the girl to grab his own drink. "I guess I deserve that." He shrugged it off, keeping his distance from her. "Yeah, saying the last time I saw you, you were fucking a bimbo in our bed," Y/N growled. She wanted to throw the drink in his face but did not want to start anything at the first party.
"Well, I can agree she was a bimbo," Calvin smirked. Y/N rolled her eyes, walking past him, her name rolling off his tongue, stopping her. "I want to talk." Calvin continued; Y/N's face twisted; she could not believe her hearing. "You can fuck off." She growled out loud enough for him to hear, rushing away.
Y/N just arrived a few moments ago and ruined the whole night. She should not have come this year; she just took a trip with Gracie. She rushed to the nearest bathroom; it was nice and quiet. She checked the stalls; each one was empty. Quiet music rang through the speakers; it was a very bright room. Y/N just needed to breathe momentarily, checking her makeup in the mirror.
She checked her phone from the tiny purse on her shoulder to see Gracie sent her three messages.
Y/N heard the bathroom door open. She was about to leave when she saw Negan locking the door. "I-uh- you are in the women's restroom." Y/N stuttered out, hearing the lock click.
"What did that asshole of a kid say to you?" When he asked her, Negan's voice was dark; he unloosened his tie a little from his neck. Y/N kept her eyes locked on his actions; she felt her toes dig into her heels. "He just wanted to talk to me." She admitted being quick with her words, her nerves bubbling up again. Negan kept leaning against the door; she felt his eyes burning through her. "What did he even do for you to leave his ass?" Negan crossed his arms, curiosity getting the best of him.
"When I moved to Georgia with him, after a while, he became distant when I was busy with classes," Y/N replied, "I caught him in bed with someone else one day after getting out of a class early."
"You're telling me someone wanted to cheat on you?" Negan chuckled, shaking his head in disbelief, "He must be the dumbest boy I ever met." Y/N blushed at Negan's comment towards her, her back resting against the counter behind her.
“He got tired of me; our relationship was struggling anyway.” Y/N declared, trying to hold a smile; maybe more of her felt tired of him sometimes. She tried to stay busy with her classes, mainly in the library. Reading was a way of escaping sometimes; she loved the darker romances. People could not understand why she got such a high education with her father's wealth; he had her set for life all the way to his great-grandchildren.
Y/N liked being in college, attending classes, making friends, and partying a little. She loved that life, but she knew she was growing up; mostly, she had grown up. Negan walked closer to her; she had nowhere to back up. All she could do was watch his movements.
“You're missing your party." Y/N pointed behind Negan; this was all in celebration of his company. "They are not missing me much, darling." He was now inches away from her, her back digging into the counter's edge.
"I thought you wanted to wait til tonight." Y/N stammered, his hands trailing up her bare thigh. Her eyes closed, feeling her legs becoming weaker by the minute. His lips rested against her ear, and she felt his breath down her neck. "The sun is down, isn't it, doll?" His words sent chills down her spine; he had her wrapped around his fingers already.
"When did you get so brave?" Y/N's lips parted, her eyes still closed, falling upon his touch. His hands finally stopped at the top of her thigh, where the slit of her dress started. "Why do you think I said yes to your daddy when he asked me to stay with you guys?" Negan whipped back, hands fingertips wrapping around her underwear.
Her mouth parted, but she couldn't let the moan out that was hanging down in her throat. Y/N wanted him to rip the lace off of her quickly; he was moving so slowly. "Sure, I am buddies with your daddy, but when I heard his fine-ass daughter was going to be right beside me, I couldn't say no." Negan chuckled, leaving kisses trailing down her neck; she moved, giving him more access. "Let me show you how real men treat women," The older male whispered against her neck, sending vibrations down to her pussy. Pulling the black lace down her smooth legs, she felt her become wetter by the second, "I will treat you like a queen for this whole trip."
Y/N lifted her leg, letting the black thong go over her heels into his hands. He was still placing kisses down her neck, moving down her collarbone and to her chest. The young woman kept letting out quiet moans, opening her eyes and watching Negan stick her underwear into his pocket. He quickly picked her up, placing her on the sink.
Y/N wrapped her legs around his waist, the heel of her shoes pushing him closer, feeling his member rise underneath his pants. He cupped her cheeks, kissing her like a crazed animal. Her hands ran into his once neat combed hair; how his kisses moved down her neck back to her lips was just enough to drive her mad. The kisses on her neck made her toes curl, his beard tickling her neck. His fingertips brushed over the tip of her clit, his hands pushing up her dress.
"God, I've never seen a woman as hot as you." The comment made Y/N snicker at him, his hand fully cupping her between her legs. The pressure was almost unbearable, and he felt barely a touch from his cup. She moaned out, digging her nails into the back of his neck. Her hands went to the zipper of his pants as he swatted it away. "It's only about you tonight," Negan winked at her, cupping her more, causing another whimper from her lips. He wanted to see her break underneath his touch all night long, "Play with your pussy in the bathroom outside of my own party; eat your pussy out tonight before you sleep."
Y/N hummed, wanting to speak, but no words could form. He had her in a state of shock and pleasure. Finally gathering her words, she did not care if it was the first night.
"I want you to fuck me."
Negan chuckled; it sounded like a sinister chuckle. A laugh she never heard from the man before. No matter if it sent fear through her, she still felt her pussy ache."Not on the first night, doll. I won't have you fallen' in love with my dick just yet." Negan snarled playfully, biting her bottom lip. He started sending more kisses down her neck.
"You could have any woman you want, Negan." Y/N whimpered, his finger slowly playing with her clit. Her hands held on to the collar of his shirt, her other hand letting her nails dig into him. Negan's hands cupped her face, squishing her cheeks together. He kept playing with her clit slowly, allowing only his fingertip touch her.
"And I am having her right now."
A/N: Below are links to this story and the complete master list to follow to keep up with the story.
Other Links for Story:
AESTHETIC
THE NIGHT BEFORE
DAY ONE (PART ONE)
MASTER LIST FOR STORY
