Try Me Too Pt. 01

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Anthony makes a daring bet with Kate Upton for an affair.
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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.

******************

Nassau, Bahamas

Water sprayed from the sink faucet, creating a high pressure noise that filled the quiet room. Trickling drops covered the white ceramic surface of the sink bowl. No reflection came from that water, but a shadow hung above. That was until Anthony glared back at his true reflection in the mirror. Starring into his own dark brown eyes, then glancing up to make his short blonde hair was fixed up right. His face was clean shaved just hours ago when he first awoke on this Monday morning. Yet another start to the week, he could feel those blues kicking in after what had been a long weekend of sleeping in. Working at a luxury hotel resort, such as the Rosewood Baha Mar had come with a price as part of the job. Despite an ugly start to a Monday morning, Anthony was in no position whatsoever to complain about his place of work or where he lived.

Just a month ago, he had hit what was the dream of a lifetime. The memories were fresh on his mind, regardless how many days were passing by. Kelly Brook had arrived at the hotel resort last month. It was a chance of a lifetime to be of her service in the massage room. One thing leading to another as they played a game together. He had accomplished what so many young men at his age would only dream of. Those who had lusted over the English glamour bombshell from her magazine shoots and media presence. Though a month had passed, that weekend still felt as if it was yesterday. Three solid days of playing lustful games with Kelly and all around the clock fucking. His twenty-seventh birthday was on the horizon in a few weeks, but Anthony felt he had already received the perfect present.

To make up for days missed on work, he had to complete some overtime shifts, but was well worth it. The thoughts of having Kelly all to himself and lusting over her giant tits were enough to wash away the negative thoughts when stuck scrubbing floors and cleaning up after the other masseurs who worked in that room. The funny thing was that his friend Scott didn't have to take any overtime schedule to make up for missing work on his Sunday afternoon. Anthony had shared a few beers and had conversations with his chubby friend after their lucky day with Kelly. To see that goofy grin across his face and hear him brag about how amazing Kelly was, didn't make Anthony cringe in the slightest. If anything, he felt he had a better friendship with Scott now after that eventful threesome.

With the weeks passing by, he had only brushed shoulders with his friend occasionally during the middle of the week. They passed by each other on Wednesdays and Thursdays. Scott had been moved to handle a cleaning crew to make up for staff leaving unexpectedly. Anthony had guessed it had to do with some recent firings, so he couldn't complain about getting off lightly after the work he missed last month. Adjusting his uniform in the bathroom, he took another glance at his hair in the mirror, just to make sure it was slicked back far enough. Appearance was important for the day, as this was his second week starting at the reception desk for morning check ins. Anthony hated having to adjust his sleep schedule, as he preferred beginning work around the afternoon, rather than clocking in at eight. Nevertheless, he was not in a position to complain.

Check ins were often scheduled in advance by the new guests who were arriving, logged into the work computers behind the desk. The Rosewood hotel was part of three wings connecting to what was a massive luxury resort. Usually it was families who had deep pockets and could afford a weekend or week long stay to go out and explore the Bahamas. Other times, Anthony had noticed quiet guests that checked in. Men coming and going in pinstriped suits and older women. Nothing could top that weekend with Kelly Brook, as yet again he was starting to daydream about her. He forced himself to drop those thoughts after stepping out of the bathroom. Anthony didn't check the computer to start the day, instead having a printed sheet of check ins with randomly assorted names. The papers were attached to his clipboard behind the reception desk.

So far he was starting the day alone behind the desk. This was not an idea way of beginning a fresh Monday morning at work. Check ins were over logged with a long list and Anthony was hesitant to begin through the list. The phone would be busy, he could only assume. So far in the morning, he had checked in four guests and knew there would be more coming along. Sitting down in the chair beyond the desk, he took once glance at the flashing computer monitor. A black keyboard was down below, with the clipboard off to the right side of the desk. Anthony noticed a yellow sticky note slapped down on the desk with names jotted down for reception work. He easily recognized three of the four names as coworkers. Anthony figured they would be stepping in as the hours progressed. He had other work to do besides check ins.

Across the hotel lobby, a tall blonde woman made a grand entrance into the hotel. Anthony wasn't paying attention but he caught an image from the corner of his eye. Large black sunglasses covered her eyes as her hair was waving in the distance. A blue dress covered what appeared to be a curvy figure. Heavy cleavage was visible up front with big tits that bounced and shook with each step she made. Matching dark blue high heels clicked and clacked with booming sounds across the marble floor below. The noise was slightly muffled with wheels to a rolling backpack. Without a care in the world, the woman marched her way directly to the reception desk in the center of the lobby. Before Anthony knew it, her towering figure had cast a shadow over where he was seated and he was forced to divert his attention up to the face starring down at him. She pulled up her sunglasses, revealing soul piercing blue eyes and then spoke.

"I'm here to check in. Are you the man I spoke to over the phone about booking a room for the week? What's your name?"

There was something about her face that was familiar. Soft pink lips with a beauty mark above the right side of her upper lip. Her massive rack nearly hung over the desk counter. Anthony shook his head, answering her back.

"I'm Anthony and no. I don't think that was me you talked to, but what name am I looking for? I'll go ahead and get you checked in."

"Look for Verlander."

She answered quickly, as Anthony was considering to himself that he thought he had seen her face somewhere before. As he glanced down the printed sheet of guests to expect, he used his right hand index finger to look through the brackets. Sure enough, he found the name Kate Verlander and then suddenly it hit him. He did know the woman standing in front of him. His heart began to race as he glanced up and then the words fell out of his mouth.

"Oh shit, you're Kate Upton, right?"

Not realizing how he spoke to her, he tried to smile as he suddenly blushed and became embarrassed. All she did was curve her lips into a smug grin.

"Yeah, that's me. I've already paid for a week's stay and my credit card was billed last night. Can I have the keys to my room, please?"

"Sure, sure! Hold on, let me check where you're booked in the computer. If you paid in advance, then you should already be logged into the computers here. Hang on, just a second."

His eyes shifted to the computer screen as Kate stood there awaiting her room key. Anthony raised both hands, swiping his fingers across the keyboard as he went through screens to check the logs. Kate had been booked to room 743. Sitting on the desk on the left hand side was a box of keys that had arranged for the early check in guests. Anthony was trying not to begin thinking of his memories he had of looking at Kate Upton in those glorious Sports Illustrated swimsuit magazines. It had been many years, but he couldn't forget those days in college of treating himself to gaze at her beauty while sitting naked in bed. It was impossible to stop those memories from flooding into his mind now that the woman was standing before him. Once he grabbed her key, he offered a smile and got up from his chair.

"Here you go. I'd like to help you get checked into your room."

This was a risk Anthony was willing to take. Stepping away from his receptionist duties to spend some time with one of the most beautiful women he had ever seen. Such a chance like this was rare in life. That weekend he spent with Kelly Brook had only boosted his confidence to act in such situations like this. Anthony believed at this point that most people didn't recognize golden opportunities when they fall in their lap. This was one and he wasn't going to let it go as he wanted to try his luck with the one and only Kate Upton. When he handed her the key, she smiled and nodded.

"I'd like that. Mind getting my luggage?"

"Yeah, that's no problem."

Leaving the reception desk without another coworker to manage it was enough to get an infraction written up on him. Anthony didn't care. Kate Upton was worth getting into trouble at work. He walked around the circular shaped reception desk and then joined Kate. She let go of the black handle to her rolling backpack and then Anthony took over as he began to roll it. Together, they marched to the elevator with her stepping in front of him. Luckily there wasn't another person in sight as they stepped through the open doorway. Anthony pressed the button for the seventh floor as Kate's eyes rolled over and she gave him a smirk. Without saying a word, he stood there and tried his hardest not to look at her heavy cleavage down below. Perhaps that was why she was smirking. After his experience with Kelly Brook, Anthony had to wonder about a woman like Kate and the temptations that she knew she commanded over hot blooded men like him.

Where was Kate's husband? That was one question Anthony quietly asked himself. It was strange of her to book a week's stay but not have him along with her. The last Anthony had read of Kate Upton on celebrity gossip sites online was that she had got married, had a family and stepped away from modelling. From that alone and her name in the hotel records, he expected to see her husband alongside her for this trip. Something wasn't right, but Anthony was not prepared to ask the question. He simply stood there, awaiting the elevator to reach the destination of the seventh floor. When it did, he stepped out and into the hall, rolling the backpack as he led Kate to her room. She offered a smirk as she handed him the key back. Anthony slid it through the knob, making one turn and then handed it back. With a smile, he nodded to her before speaking.

"Welcome home, you're all set."

"Only for a week this is my home."

Kate was quick to correct him before they stepped through the door. Anthony shut the door after stepping in as they now had some privacy together. Her heels clacked loudly across the wooden floor below. Every room in the hotel had a similar look with the same wooden floors and white walls. Kate stood there, glancing around the living room as Anthony rolled the backpack in.

"Where do you want this?"

She looked over at him, then realized he was talking about her backpack. Kate took another glance around the room.

"Oh, uh... run it to the bedroom, please. I've got clothes in there. I wouldn't mind getting changed now that I'm settled in."

Upon her request, Anthony rolled the luggage into the bedroom and picked it up. He placed it down over the bed and then checked to make sure her sheets were fresh. He could hear her heels clicking and clacking off in the distance and then she stepped behind him.

"Thanks."

Kate stepped past him and then grabbed at her backpack. Anthony watched as she bent down, giving a terrific view of her full cleavage. The sound of the zippers sliding down and buttons popping had made his imagination begin to run wild. Even after having one weekend with a famous model, he still had this shocked feeling bottled up inside that he was in the presence of another one. Now seemed like an ideal time to begin a conversation with her and see if he had a chance like he had with Kelly.

"You know, I'm a huge fan of yours. I still remember when you did those Sports Illustrated shoots. I gotta say, those were some great times back in the day."

Her eyes shifted at him and then Kate smiled, flashing her teeth while clutching some clothes in her hands.

"Thanks. I used to get that a lot."

"Get a lot of what?"

"Guys like you who recognize me and call yourselves big fans. It's been a while since I ran into someone like you."

Anthony blushed upon hearing her words, trying to hold back his smile. Kate smirked back at him. Her heels were muted into thumping sounds with the red carpet floor down below. She stepped around Anthony and went to the bathroom connected within the bedroom.

"You mind if I call you Kate?"

The door slammed shut and Kate had only given him silence at first for several seconds.

"Yeah, you can call me that."

Swallowing his breath, Anthony didn't want to stammer out any words and trip over himself. He thought now was the ideal time to mention her husband and perhaps figure out her intentions of staying a week in the Bahamas.

"So, I saw you were married. Kate Upton wasn't the name in the computer when you checked in."

"Yeah, and?"

She yelled her response from beyond the bathroom door. Anthony was forced to think for a few seconds before he replied.

"Well... usually couples check in together. Should I... uh... make reservations for him to join you tomorrow or something?"

"No!"

Kate's reply came out loudly as she to talk from behind a closed door. Knowing that he didn't have to worry about her husband showing up, Anthony was beginning to feel he had a chance. A few seconds passed when the golden knob to that white bathroom door began to turn. His eyes gazed forward, noticing the veil of light as the door came cracking open and then Kate made a reintroduction before him. The dress was gone and instead she stood in a white one piece swimsuit hugging all of her curves. Anthony's eyes immediately glanced at her giant breasts that seemingly were ready to pop out of the tight outfit. Shoulder straps hung over, as her hair was still parted down the middle with swiftly waves. Her lips curved into a grin as she spoke.

"Well, how do I look?"

"Are you wearing that for me, Kate?"

She giggled at him, placing her hands onto her hips and turning around to show her buttocks. It was almost as if Kate were modelling before him. When she turned to face Anthony, she replied to his question.

"Maybe. You did say you were a fan. So do I look like a woman who has went through pregnancy or not?"

"I don't think that matters, Kate. You're in killer shape."

"I know I am."

"So is that why you arrived here without your husband? You planning on getting someone like me to stare at your beautiful body?"

Once again, she smirked before shaking her head.

"Maybe, maybe not. I've got a photoshoot planned this week for an old friend. Let's just say I'm getting warmed up after checking in to my hotel. So where's the pool?"

Anthony smirked back at her.

"You're gonna go down to the pool and see if any other guys recognize you?"

"Maybe... I've gotta say, it feels good to be out and about like my old self. I haven't felt sexy alone in a few years now."

"Is that the result of being stuck at home all the time with a family."

With a nod, Kate bit down on her lower lip.

"Yeah, I guess you can say that. Not that I don't appreciate them, but since I'm gonna be modelling again... maybe I just wanna feel like my old self."

"By having men lust over you, is that right?"

Blushing, she grinned with a flash of her teeth. Anthony stepped closer to Kate, gazing back into her beautiful blue eyes. If there was any chance he had with this woman, now was the time to take it. Bold steps had to be taken and he was willing to go that extra mile for her. After his time with Kelly, he had gained such confidence, he was no longer afraid of finding himself in situations like this.

"Why don't you let me be the first. If it's something like a one night stand you're looking for, I can tell you right now Kate, you won't be disappointed."

After uttering his speech, Anthony had to consider the possibility that she would slap him across the face. He knew it was a rude manner of trying to seduce her, but there he was trying to play his cards anyway. Kate stepped back and smirked before responding in a low tone.

"I wasn't planning on climbing into bed with the first man I met out here today."

"I'm not just any man though. Try me, you won't be disappointed."

Still smirking, she quirked her eyebrows up. She glanced down to read the name tag on his uniform before stepping away from him.

"I'll think about it. You're cute Anthony and you've got balls. I like that in a man."

He turned around to face her, trying to conceal his smile but not without blushing. As his cheeks flushed red, Kate caught his eyes glancing down at her heavy cleavage.

"Give me some time to think about this. If no one catches my eye down at the pool, I'll call for room service and ask for you personally."

Anthony shook his head.

"Nah, I think you're just trying to brush me off. What would you call room service and request?"

"Wine. I'll be wanting a bottle come evening time when I'm ready to unwind."

"I think I know where I'll wait for you tonight then."

"If it's you over the phone, I might just request you deliver it to me in your birthday suit."

Kate licked her lips after responding. Anthony simply nodded before letting out a slight chuckle. He waved his hand at her, ready to leave.

"I'm just gonna hope you really do call since I'm about to move down to the housekeeping unit."

"Don't waste your time, if you've got a lot of work to do today. Think of something to impress me and then... maybe I'll try you."

She winked at him before waving back and with those words, Anthony didn't see a need to say goodbye. As he marched back to exit her suite, he began to think how he was going to slip out of work today and try to wiggle his way into bed with Kate Upton. If he had accomplished something with Kelly Brook, then he believed it was possible for this woman to fall in his arms too. Back down in the lobby, there would undoubtedly be a manager or some coworkers to complain at him for leaving the desk unattended. Life came down to taking risks and jumping at golden opportunities, as Anthony reminded himself. Kate wanted to be impressed, so he began thinking of just what he could do to leave her wanting more. Then again, what if she did go out to the pool and found a much better looking man than him to bring back to her room? Hard questions lingering about almost brought stress for an adventure that would result in some repercussions from skipping work.

******************

3 HOURS LATER

Avoiding the hotel lobby, Anthony wanted to run away from his work duties for as long as he possibly could. Thoughts of Kate were at the center of his mind and he was willing to forget about everything else in the day and try to impress her. Outside the hotel building was the pool and he expected to see her there, but Anthony didn't go out to take a peak. Instead, he shifted across the building as if he were running away from something. Work was the only thing he was avoiding as the day began to carry on. His cellphone started to ring and vibrate from within his pocket. With no doubt it was a supervisor requesting to know his whereabouts. For now, Anthony ignored the phone. He went back to his personal suite and changed out of his work clothes to put on something that was more fitting for leisure and to blend in with the regular guests.