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. It picks up where Try Me Too left off as a direct sequel, enjoy!
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Nassau, Bahamas
Hot air followed anyone inside with the swinging doors left open to the pool area. The back of the Rosewood Baha Mar hotel building led to a massive swimming pool as part of the resort. Sunlight nearly blinded Scott's view as he stepped back outside. Sweat had already formed under the collar of his unbuttoned white shirt. It was possibly the worst choice for a shirt to wear on this hot day outside, but dress wear was rarely something Scott put much thought into. His locks of curly red hair had a heavy orange tint in the sunlight. Today marked Wednesday, and Scott had a rare off day on his schedule. It was the reward of hard work, as he had not missed a shift in over ten months. Unlike his friend Anthony, Scott prided himself on working hard and saving his money. Whatever he planned to spend his earnings on however, that was of no concern.
Living at the hotel, Scott had been working for years with no life commitments apart from leisure spending. He would cash his pay check, pay a phone bill, and other necessities as part of his job. The rest of his earnings were saved, sometimes for the use of fun weekends alongside his friend Anthony. Every once in a while, they needed to unwind themselves with some alcohol and bonding over women. Before last year, the two had a loose friendship, but since the affair with Kelly Brook, Anthony had taken a new liking to Scott's company. Since then, the two men had bonded over babes, counting Kate Upton as one of them, and now another model who occupied his thoughts. Every day they discussed women, Scott had to remind Anthony of his luck in life, but right now he was feeling like the lucky one. After all, he met Kara Del Toro first before Anthony.
Yesterday he could not help himself. Knowing that Anthony had a romp affair with her back in her room, Scott wanted all the details. Anthony scolded him, as he complained about how Kara easily manhandled him. Sometimes Scott felt as if he was being treated as a laughingstock in a room. Whether it was due to his chubby frame or his personality, he did not know at times. From Scott's point of view, Anthony came off as arrogant and headstrong. On the flip side, Scott knew that his friend viewed him as a nuisance from time to time. The men had their differences, but the friendship remained. Deep down, sometimes the resentment was too much for Scott. Anthony did not want to share his luck with him unless he was needed. As Scott remembered, Kate Upton was different from Kelly Brook. She called him the big boy, a nickname he took great pride in because of the size of his stomach.
Below the buttons of his shirt, Scott's stomach barely fit into his pants. Tucking his shirt in was impossible, but he did not care today. Off the clock and not checking in to work, he had no shame in walking out to the pools with his fat belly exposed. The sun was out with no rain on the radar this morning. The outdoor pool at the hotel was massive, leading to a full resort on the other side of the building. Scott could recall his first time working on the pool side. There was an extended walkway through the pool leading to a small tiki bar. On the hottest of summer days, it did not matter if the bar had a roof and active ceiling fans. The heat would find a way to soak in, leaving anyone ready to take off their shirt and dive into the pool. Scott was properly dressed for a swim today if he wanted it. His soles were covered by a pair of white flip-flops, which went with his shorts.
He could not hold back the goofy grin across his face. Today was beautiful, and he was on his way to see something even prettier than what the weather offered. Since yesterday, Scott had been keeping a close eye on Kara Del Toro. Just two days ago, he met her at the reception when she checked in to the hotel. A funny woman who had a history with Kate Upton, eager to trace the other woman's footsteps back to the hotel. Kara knew all about Kate's affairs, spoken from word of mouth. Anthony had reveled in his luck after having a romp with Kara, but the way he talked about her, Scott knew his friend had to be embarrassed about something. The simple fact of the matter seemed to be that Kara destroyed him. Anthony did not want to talk about it at all. 'She was good', was all he could muster out in words when pressed on the issue.
With a watchful eye, Scott knew where Kara was spending her time earlier in the day. Through the hours of yesterday, he had been keeping tabs on Kara. It was easy for him to check the phone logs on a computer and see what she ordered from room service. The option was there for him to come into her room at any time and greet the gorgeous model, but Scott had other ideas in mind. When he first met Kara, they shared a long conversation about what all Kate had told her. The first thing Scott asked was if she referred to him as the big boy. He took great pride in that nickname from Kate, but Kara only laughed in his face when he mentioned it. Maybe Kate did not inform her for a good reason. Kara had at least told Scott that from Kate's own mouth, if she had to pick between the two men, she was going with Scott. Whether she was lying or not, he did not care.
It was only a compliment to make him smile, rather than a massive ego boost that such words would have been to Anthony. For once, Scott felt like climbing over his friend and proving that he was more than just three-hundred pounds of joy. By chance, if Anthony had not given Kara a memorable affair, Scott was ready to prove that he was better at fucking than his friend. As he walked his way around the pool section, he kept that same silly smile across his chubby mug. Without a care in the world, Scott was excited about going out to meet Kara today. The only reason he knew she was out at the pool was due to some sneaky peeping. Scott watched Kara's door on the seventh floor. He was off work for the day, so he used a free maintenance cart to pretend he was doing something in the hall. Kara left her room in a robe, clutching a towel. She never seen him on the other side of the hall, as Scott easily ducked behind the large cart and hid himself.
That was an hour ago, a few minutes past two PM. Kara was still outside near the pool, relaxing in a lounge chair with her feet propped up. Scott had walked through so many people, taking a moment to remember how many guests checked in during the week. The pandemic had changed things for a time. Scott could remember all through the 2020 year as fewer guests were arriving. Two years after that nightmare had ended, the hotel was seemingly more packed than ever. As he walked, shirtless men passed by. Scott offered a friendly smile to an older woman he noticed to his left. Her eyes did not cross his, as she was laughing at a man who must have been her age. Unable to resist, Scott took a peak at what only he would declare to be a set of 'big ass titties' bouncing in a loose black top. His eyes narrowed across a row of white lounge chairs on the eastern side of the pool.
Scott grinned when he noticed Kara Del Toro was still there. She may have switched chairs to go for a swim, but he could recognize her in a row of only four women. The chairs on both sides of Kara were unoccupied, offering a spot for Scott to have a seat. Rather than join her in what appeared to be a sunbathing session, She was laying across the chair, feet dangling from the edge. A leopard-patterned top covered her busty tits, tied around her back with no straps. The same print pattern covered her bikini bottoms. Her long blonde locks of hair were flowing from the chair. Dark sunglasses shielded her eyes, and sitting next to Kara's right side was her cell phone and a towel. Her tanned skin was so beautiful in Scott's eye. Since he had nothing on him, he glanced around an empty chair and noticed a spare bottle of sunscreen someone had left behind. Grabbing the bottle, Scott shook it up as he called out to Kara.
"Hey Miss. Del Toro! Having a fine day?"
She turned her head, glancing in Scott's direction. Without answering at first, Kara raised her sunglasses as if to get a better view of him. He began to shake up the sunscreen in his right hand while Kara's eyes locked on his face as he spoke again.
"You look like you could use some company today. You mind if I help you out with this?"
He showed her the bottle of sunscreen. Kara flashed her teeth as if she were about to smile, but instead rolled her eyes. It gave the impression to Scott that he was probably annoying her. That was a reaction he was used to seeing from people.
"Aren't you supposed to be at work, Scott?"
"Not today. I've got the day off. Would you like some sunscreen on your legs?"
Laughing at him, Kara leaned up and grabbed her phone. She bent her knees, pulling her legs up and then extending them back out. With a smug grin, she replied back to him.
"I've gotta respect a man who asks if he can make himself useful."
The tone in her voice echoed with such arrogance. Scott knew he was stroking her ego by offering her service like this, but what did he care? He could easily guess that from his body size, he was not her preferrence of a man. Falling down to his knees over the concrete, he positioned himself at the edge of her chair. Kara took her sunglasses off, leering her big brown eyes at him as if she had absolute control of this chubby man already.
"Did you come all this way out here to meet me today?"
Kara spoke while shoving her left foot out. Scott shook the bottle once last time, then squirted out the white liquid substance into the palm of his left hand.
"No, I came out here to go for a swim."
"With no towel?"
That smug look remained on her face. Scott figured that she knew he was lying, so he offered a smile as he began to rub her left foot.
"No, I was only kidding. I really wanted to come out here and ask you something."
"What?"
While quick to reply, Kara still seemed bothered by his presence alone. He took his time applying the sunscreen on her foot and then up her leg.
"It's a personal question about my friend."
"Go on."
