Try Me, Big Boy!

Author's Note: This story is completely fictional and did not happen. All characters and names are fictional and were made up. I do not make money from these stories. Please do not copy and plagiarize my work.

This story was written for Galva82 and is dedicated to him. The celeb choice and themes were his ideas, enjoy!

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Nassau, Bahamas

Loud voices echoed in the distance, with the sound of feet stomping and rolling carts through the main lobby. Friday had come, marking one of the busiest days at the Rosewood Baha Mar hotel. Anyone who worked on staff for longer than a year learned to deal with the many guests at the end of the week. Just as soon as the paychecks were cashed, it was time for a long weekend. Overtime was available if someone was willing to go for the entire seven days. It was easy when you had your own residency suite at the hotel itself. The job had become a walk of life for the employees who had been there longer than twenty four months. From the main lobby to the staff rooms, the giant resort seemed like a small world once someone learned their way around the buildings long enough. Someone who went by the nickname 'Big Boy' understood the size of this place.

Life was good, according to Scott. Or at least that was what he had to tell people who hated this job. After the early morning shift, he was spending his break time across a hall from the main lobby. He stood near the doorway where two vending machines sat. He had just put a dollar in one to purchase a Butterfinger bar. As he stood there, Scott chewed the candy bar piece-by-piece. He did not have a care in the world today. His chubby frame was fully exposed in his work uniform. The buttoned up white shirt was tucked into his black pants. If not for his chubby belly sagging forward, anyone would be able to see the chrome-plated custom belt buckle he wore over a black embroidered belt. In an oval shape, six letters made the words 'BIG BOY' in capital letters across the plate. It was the one piece of custom jewelry he wore as part of his work uniform with a sense of pride.

Few people seen the belt buckle, not that Scott cared. The only person who ever asked him about it was his friend Anthony. He could still see the other man rolling his eyes when he showed him the decoration. Scott could never forget that one week Kate Upton spent at the hotel. She gave him the nickname 'Big Boy' due to his excess weight and the other big thing besides his stomach. He was so proud to know he was one of the luckiest men in the world to bang that busty supermodel. As time went by, he took the nickname with heavy hubris. Only Anthony knew the meaning since the two of them had shared a few affairs together with models over time. Their first adventure involved Kelly Brook. The last one was Kara Del Toro, whom Scott took great pride in knowing he gave her more thrills than his friend achieved. It was a friendly rivalry of sorts in those rare circumstances when they were in the company of certain guests.

Anthony was the only friend Scott had left in life. He could be rude and arrogant at times, but Scott ignored that. He saw something good in Anthony. Most of their coworkers went about their days with no regard for friendships on the job. Scott and Anthony had a different outlook since they lived at the hotel as residents. The job was all they ever knew in the Bahamas. They were both single men in their twenties, quickly approaching thirty before they would know it. On a bad day, they could easily remind each other about the good times that began two years ago. Remember when we banged Kelly Brook? Or what about the time we fucked Kate Upton? How about the time Gianna Michaels was escorting at the hotel? Kara Del Toro was the name they rarely reminisced over. Scott knew better than to rub it in on his friend. He would always have that one over Anthony, knowing he was the better man in the bedroom, according to her.

Two years had passed since their first affair with Kelly Brook. The incident with Kara was a year ago, as it was the last time either of them had gotten laid. Good times did not come often. Scott cured his lonely nights the old-fashioned way. He enjoyed sitting in bed at night with his laptop open as he jacked off to his favorite social media models. He made sure to order Kelly Brook's recent 2024 calendar as a reminder of that lucky weekend. For the past several months, Scott had taken a particular interest in Demi Rose Mawby's massive ass. If only she would check in to the hotel, he may finally be encouraged to lose over a hundred pounds to be able to give that booty the fast pounding it deserved. His phone wallpaper was a picture of her huge tits and lovely face. There were other models Scott took an interest in, but he always went back to the only three he could say he banged. Anthony was annoyed at how much he liked to brag. He enjoyed reminding Scott that no one would believe them if they told their lucky stories.

Kara checked into the hotel solely from word of mouth from Kate Upton. That made Scott and Anthony both wonder if Kelly Brook had any modeling friends back home in England. Would she sing praises to her female friends about the two men? Anthony figured it was a long shot, but not Scott. He was a dreamer and preferred to live in fantasy while stuck at this job. They had to have made an impression since Kelly and Kate wanted more than a single night with them, or so he told himself. As he stood against the wall, finishing the Butterfinger, a mischievous grin ran across his chubby face. He was thinking about his friend, whom he had not heard from in four days. Anthony had to leave work for a family related emergency involving his father. It would be his first trip back home to the US since leaving college. Scott did not envy him, for neither of them wanted to go back home any time soon. With Anthony gone, he had no one else to socialize with in the passing days at work.

"Hungry again?"

A voice alerted Scott as he turned to see his supervisor, Dave, standing next to him. The older man looked unimpressed as he gave him a dirty look.

"Yeah, I'm on break right now."

"So, I've heard."

Dave was known as a stern, rude manager. Scott sighed in anticipation of the usual lecture and cheap joke about his weight. The older man enjoyed bragging about how he could still surf in his sixties and was in good shape. It was just another way of reminding Scott how obese he was. Not that he cared to be lectured by this old fart.

"Do you need something, Mr. Dave?"

"I'm looking for someone to take over room service duties for the evening. Gerald got sick and had to call off a few minutes ago."

Gerald was one of the many employees, like Scott, who worked alternating shifts. His name was familiar, but Scott was rarely on shift with him.

"Can you finish the day on room service?"

"Yeah, sure."

The old man nodded with a little smile. He knew Scott would never say no. That was the only reason he went and bothered him on break. At least he did not make any more remarks about his weight. When he walked off, Scott sighed and tossed the candy wrapper into a trash bin close by. A few guests walked past him. A man and a woman wearing swim trunks and a bikini. The woman gave Scott a dirty look as she caught him gazing at her ass in a red two piece swimsuit. All he could do was grin back at her. On a boring day like this, he wished Anthony was around to shoot the breeze with. Even if they just talked about the normal day-to-day shift, it beat having to do everything on his own. At least he was getting paid, or so he had to remind himself. Anthony liked to miss days and even break on shifts sometimes when he would just skip time. Scott never did that. He only took sick days off if he truly came down with something contagious. This was simply one of those days on the job where time could not go by faster.

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2 HOURS LATER

Loud clanking echoed down the hall for no one to hear in the empty silence. Scott sighed as he checked the rolling cart. The sounds belonged to a metal tray filled with a bucket of ice and a bottle of wine. Dave did not inform him that no one else was working room service on the lower floors. Scott was stuck all by himself, tending to various calls that required him to make routine stops in guest rooms. It would have been nice if someone else was sharing the shift with him, but he knew better than to complain. The last thing he wanted was to get publicly chewed out by a manager. This was not the first time Dave had stuck him on a shift where he had to do everything by himself. Scott fell for it time and time again, never thinking when he accepted that this would be another day of hard work. Much of his frustration had to do with a cart with a loose, squeaky wheel. It made matters difficult to turn around in halls and leave elevators.

Replacing the cart would require a phone call and a trip to another floor. Scott hated bothering the other employees on room service duty. He tried to make due with the cart by pushing it at slow paces. This only made the squeaking sound louder. The noise was grating to the point of sounding like fingernails scraping across a blackboard. A few hours into the shift, he noticed that the time was 3:14. Just a few more hours, and he could clock out since his regular shift was from seven in the morning to five in the evening. He reminded himself that things could be worse as he opened the door and carefully pushed the squeaky cart into the hall. A short trip to the elevator was in store. Luckily, no guests would be joining him since the hallway was empty. This only made the squeaking of the cart sound more irritating as it echoed in the distance. Scott let out another sigh once he reached the elevator and pressed the button for the fifth floor.

A woman ordered a bottle of wine a few minutes ago. To compliment her request, Scott scooped enough cubes to fill a small metal bucket of ice. A simple wine goblet was wrapped in a fancy napkin, also sitting on the tray next to the bottle and bucket. When the doors to the elevator opened, Scott braced himself for the screeching sounds that would soon be heard. The hall was empty, like the last one he departed from. He let out a sigh as the loud noises annoyed him to no end. Forcing a smile, he continued to slowly push the cart as he turned his head to look at the numbers hanging on the doors. Once he reached room 532, Scott sighed in relief. He stopped pushing the cart and walked around it. As he turned, his fat stomach rubbed against the side of the tray, nearly knocking over the wine bottle. Due to the squeaking sounds, he did not want to push the cart into the doorway. Raising his hand, he cleared his throat and began to knock on the door.

"Room service!"

"Come right in!"

The same voice he heard on the phone called out to him, this time in a more high-pitched tone. Scott turned the doorknob with his right hand. As the door opened, light shone through the crack, and the sound of hip-hop music could be heard. Bass beats combined with the flow of a rapid lyrical delivery. No one was seen in the room. Scott glanced across the white walls, hoping to see the woman make an appearance. After a few seconds, he turned around and carefully grabbed the metal tray from his cart. Focusing his eyes on the wine bottle, Scott had to make careful steps to turn back around and re-enter the hotel room. The loud music was no distraction as he watched the wine bottle slightly move with each step. In the living room sat a glass oval shaped table near the black leather couch. Scott placed the tray down on the table and leaned up to see the figure of a curvaceous woman standing across the room.

"Sorry, I couldn't get the door. Thank you for bringing that in."

Her voice was high pitched, almost bubbly, in a unique tone. Scott's jaw dropped as he stood there, captivated by the beauty in his line of sight. A woman stood wearing a silky white robe that covered her buxom body. Her skin was tanned to give the impression that she had seen a healthy amount of sunlight. Huge breasts were encased in a blue bra. Below, he could see a matching blue G string. Jet black hair was curled in a high ponytail to show her full face with plump pink lips and emerald eyes. From the minute he saw her, a sense of familiarity struck him. Scott was sure he had seen this woman somewhere before. As she stepped closer, her breasts bounced in the bra. She saw the shocked look on his face and curled her lips into a smug grin, as if she were proud to have that effect on him. His eyes were almost glued to the sight of her jumbo boobs.

"Uhhhh, yeah. No problem! If you ever need anything, just call me anytime."

As he spoke, Scott's eyes shifted from her boobs up to her face. Something about her looked so familiar. She giggled at him and stepped closer.

"Oh! You brought me some ice too, thank you!"

When she smiled again, it finally dawned on Scott just where he had seen this beautiful woman. Many nights he had spent in bed scrolling through social media looking at her photoshoots. There was no mistaking that voluptuous body and cute face. Scott knew he was standing in front of Abigail Ratchford.

"Oh shit, you're Abigail Ratchford."

He gasped after uttering his words. She grinned, quirking her eyebrows at him. Scott was grinning like a winner now.

"You know who I am?"

"Yeah! Had I known I was bringing you wine, I would've sent you a free bottle and some flowers too!"

She began to laugh loudly. Her high pitched voice was only adding another layer to how turned on he was by her appearance. Abigail seemed to be impressed that he recognized her. She pressed her left hand on her hip, not even bothering to cover her body in the robe.

"I'm shocked someone knows who I am. You're the first person to notice me since I left L.A. I guess I'm not famous enough for anyone else working here."

"How long have you been staying here?"

Tilting her head, she teased him with a smirk.

"This is my third day here. I'm on a little vacation by myself. Sometimes you have to get away from work, you know?"

Scott could not contain his grin.

"I've been following you on Instagram for almost ten years now."

"Really!?"

He nodded in response to her question. Abigail cracked up, laughing loudly at him.

"I guess that makes you a big fan."

"Oh, yeah! I'm a big fan, alright! You're fucking hot! Your tits are HUGE!!"

It was impossible for him to contain his thoughts. Scott did not think twice to blurt out what he was thinking. Most women would have been instantly offended by his rude remark. Abigail was visibly blushing, trying to contain her laughter.

"Thank you. What's your name?"

"If I can call you Abigail, you can call me Scott!"

She was still laughing as he extended his left arm for her to shake. Abigail shook hands, allowing him to feel the warmth of her palm. After the brief moment of silence, her expression changed. The smirk on her face was smaller as Abigail shifted her demeanor in a matter of seconds.

"Thanks for the wine, Scott. It's always a pleasure to meet one of my fans."

Her voice became more seductive, still carrying that bubbly, high pitched tone. Scott was still smirking like an idiot. The more he looked at her wonderful body, Scott could feel his dick beginning to grow inside his pants. Here he was thinking to himself if he had a chance with this busty beauty. Unlike his affairs with the previous models he met, Anthony was not here to compete with him. His confidence was sky high, regardless of how fat and ugly he looked in comparison to this gorgeous vixen.

"If you need anything else, just call and ask for me. I'm still on shift for another two hours."

He winked at her in a vain effort to flirt. Abigail quirked her eyebrows to tease him in response to that slight gesture.

"You get off in two hours?"

"Yeah. I usually work morning shifts."

"Oh, really? I guess that's why you've never brought me anything. When I call room service, it's usually a... slim guy that visits me."

Her eyes moved to his sagging stomach when she finished those words. Scott did not let her remark prevent him from smiling. Nothing could bring his confidence down in this moment. All he did was laugh at her, wishing she could see his custom belt buckle, which he was so proud of.

"I'm guessing that's Terry. Or maybe it's Gerald."

"I don't know their names."

"But you know mine! That makes me special!"

Scott laughed at his own joke, while Abigail grinned at him. That look on her face told him he had a chance with her.

"Are you single, by any chance?"

Giggling at him, Abigail blushed for a moment. His question took her by surprise.

"You're really curious?"

"Yeah! A hot woman like you needs a good guy to keep her company."

He winked again, but she did not laugh that time. Scott decided to joke about himself to try and crack her up one last time.

"What's the matter? Am I too big for you?"

Laughing again, Abigail shook her head.

"You're a working man, Scott. Don't you have other guests who might be trying to call for room service right now?"

Oh shit, he thought to himself. He lost all train of thought and completely forgot about the job. Abigail finally managed to wipe that goofy smirk off his bloated face.

"You're right. I better go check. Sorry for wasting your time, Abigail. You're like... super fucking hot, though. Sorry if I'm being rude, but I just have to say it."

If only she could see the bulge in the front of his pants. All this time, he had been standing in her room; his cock had erected to the point where his pants had tightened up uncomfortably. His stomach prevented her from witnessing it. Scott had no filter in his words as he blurted out his true feelings. He turned his back to her and hurried out the doorway to reunite with his squeaky cart.

"Bye bye, Scott!"

The sound of her voice made him turn to see that woman one last time. Abigail pressed her puffy lips together and raised her right hand to blow him a kiss. He grinned at her and waved back at her before grabbing the doorknob. As he stepped out, Scott shut the door behind him. The loud music was now muted, as he was alone again. With a sigh, he tried to gather his thoughts while his heartbeat was racing at a fast pace. It did not matter if he had a realistic chance of banging her or not. Scott was just happy to meet Abigail and flirt with her a bit. He knew deep down that he most likely did not give her a good impression, but at least she laughed. It was worth flirting with her just for that alone. As he pushed the squeaking cart, Scott began to laugh. The squealing sounds did not bother him as he rolled the cart towards the elevator.

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1 HOUR LATER

"Those titties were so huge. Ohhhh man, I thought they were big just from looking at pics. But they're way bigger up close. I mean, GODDAMN, I want to fuck those titties so bad! Ohhhhh, yeah!!"

Scott groaned as he studied his reflection in the mirror. His pants and underwear were pushed down to his ankles. He was standing on a wooden step ladder. It was the only way to elevate his height in the bathroom to such a level that he could see his cock at the bottom of the mirror. His right hand fingers were tightly wrapped around his long, thick pole. After returning to the staff room, Scott could not control his arousal. The job no longer mattered. He ignored any missed calls and immediately pulled his phone from his pocket and began scrolling through old photos he saved of Abigail. His bulging cock was begging to be released, hence why he hurried to the personal bathroom and locked himself inside. No one could bother him as he masturbated in this tiny white room. So many dirty thoughts ran through his mind.