Try Me, Pay to Play

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

This story was written for Galva82 and is dedicated to him.

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Nassau, Bahamas

Rays of light reflected across the marble stone of the front receptionist desk of the Rosewood Baha Mar hotel. Down in the lobby, it was a usual Monday afternoon. Anthony had just wiped the surface of the counter clean from where a drink had spilled minutes earlier. Standing in his freshly made white company uniform, Anthony let out a sigh as this was seemingly a time of break from the usual guest check ins. A slight beard of black hair had grown on his face after three days of forgetting to shave. It came as a result of hard partying, in consecutive off days from work. Spending a Saturday night drinking with his good friend Scott had come with consequences, as both men spent their Sunday evening with a hangover. The least Anthony could say was that he was feeling better to start the work week, but the feeling of Monday blues had only now just begun to set in.

His eyes scanned down across the flat screen of the desk computer. The phone had yet to ring for another new guest check in for the past twenty minutes. Another lucky break, or so it seemed. Checking the clock for 12:35 at time, Anthony decided to wait until the clock struck 1 PM before he went out on his luck break. He couldn't complain about today's schedule, as he wasn't stuck doing clean up maintenance or working in the spa room. Across the right side lobby was a familiar face, though Anthony could only catch a glimpse of the figure walking from the corner of his eye. Sighing and then breathing heavily, Scott walked as if he had been in a hurry, glancing around the lobby in hopes of finding someone. The chubby red headed man walked with his obese stomach wobbling around, barely contained with his buttoned up white shirt tucked into a pair of white pants.

Like Anthony, Scott was also on duty for the day. Some time ago, Anthony would've found the fat man to be annoying and embarrassing. Scott still had the talent in making loud remarks that would irritate Anthony to a degree, but times had changed through their friendship. It came out of the bond they shared from experiences alongside two famed models who had checked in to the hotel last year. Kelly Brook had given Anthony a weekend he could never forget. That final day where he shared the busty British beauty alongside Scott had forged a new level of friendship between the two men. That union had only grown stronger since then, when Anthony checked in Kate Upton for a week stay at the same hotel. Time had went by since their time with Kate, but Scott made sure to bring it up as a fun memory on weekends like the last few days when they shared beers.

"Hey man!"

Scott called out to Anthony. Not expecting to hear that voice, Anthony, turned to see his chubby friend. A big shocked grin moved across Scott's silly looking mug, as if he had just heard some unsettling news. His eyes widened while stepping closer to the receptionist desk.

"Dude! You aren't gonna believe this!"

Before he could finish speaking, Scott pointed his right hand towards the computer.

"Type in the name Gianna Michaels."

Confused at how he had yet to explain himself, Anthony gave his friend a puzzled look.

"The fuck are you talking about?"

"Gianna Michaels, dude! Don't tell me you don't know who she is! She's got huge boobs, let's just put it that way."

Just like that, Scott had easily annoyed Anthony right from the start of this conversation. Rolling his eyes, Anthony knew precisely who he was talking about. Gianna Michaels was a porn star legend and Anthony could easily recall several nights watching her scenes on a laptop back in college. Now was not the time for that conversation, Anthony snarled back his response.

"I'm at work right now. I don't know what you're doing, but if you think I'm looking up porn, you must still be fucking hung over from yesterday."

Unbothered by his attitude, Scott just smiled and leaned down across the receptionist desk. Still keeping that same goofy grin, he quirked his eyebrows up at Anthony and spoke in a low voice, almost as if he were speaking of a secret.

"Put her name in the computer and pull her up. She's open for business, escorting at the hotel. She must've checked in over the weekend."

Anthony's eyes enlarged, as he felt his heartbeat begin racing in his chest. The legendary Gianna Michaels escorting at this hotel today? No, that had to be too good to be true. Scott wasn't known to lie about such things, but Anthony still had some doubts.

"Really? Who told you that?"

"Trey told me on my lunch break. Dude, he spent his whole week pay check to get a chance with her!"

Leaning back, Anthony rolled his eyes and sighed at the mention of Trey. He was another coworker, similar to Scott as he shared shifts alongside Anthony. A tall black man with short dark hair, not a man who socialized or enjoyed much conversation among the staff. To think about Scott getting along with Trey sounded almost as unbelievable as Gianna escorting. Anthony could easily see Scott aggravating Trey with his personality alone. Before he could make a comment, Scott continued speaking.

"He paid for two hours with her this morning. I don't remember how much he said she charged, but it was a lot. He told me he just about broke his dick off in that ass! Dude, you should've seen him staggering! He could barely fucking walk!"

Scott's voice began to elevate as he told the story, becoming more animated and causing a random person to pass by and give strange looks at the two men. Anthony became more curious as he told the story, forcing him to focus his sights back on the computer screen as he proceeded to type in the name. As the results flashed across the screen, Scott leaned in a bit more across the desk to read the screen. Unable to contain his grin, flashing his full white teeth, the other man pointed his finger at her name.

"See, I told you!"

Reading the name across the screen, Anthony could see Gianna had checked in under that name Saturday. If only he or Scott had been working that day, perhaps they would've learned of this sooner. Surprised by this, Anthony leaned back in his chair, almost in complete disbelief while Scott was still grinning.

"I forgot to tell you, she's hanging out down in bistro."

"Really?"

Scott nodded his head. While the two men shared their conservation, no one approached the desk to check in. Anthony was grateful for that, as it left him a small window of time to consider his options. Knowing that he had already found himself lucky in the past with two busty models, it was easy to feel confident about this one. The one thing Anthony had to think twice on was the costs of Gianna. He glanced down at his reflection across the marble top of the desk. Barely able to see his short blonde hair, now wishing he had shaved his face to start the morning. Since Scott was still standing there close to the desk, Anthony stood up and smiled to his friend.

"I'm heading out for lunch, you wanna take my shift?"

Letting out a sigh, Scott shook his head.

"Oh come on, man! Are you serious?"

Smiling back to his friend, Anthony couldn't hold back that grin. He didn't want Scott following him for this trip to meet Gianna. Even though the two men had come together and shared experiences with Kelly and Kate, Anthony had other ideas in mind. The last thing he wanted was Scott there, offering to pool money together to pay for them both to get a lucky chance. There was always the possibility that for a threesome, Gianna would charge more. More than anything however, Anthony didn't want to share if he could afford her. Standing up from the desk chair, he patted his hand across the desk.

"Come on, someone's gotta check people in. I'm on lunch break and you're the only person here active, so it's your shift now."

With a frustrated sigh, Scott just gave Anthony a pouty look. The tables were turned, putting the other friend into a position of work. Anthony expected Scott to make a comment as he began to walk off from the receptionist desk, but the other man didn't. Forced into a spot he didn't want to be, Scott stepped behind the desk and took Anthony's place, now working behind reception. It seemed convenient that only now, the phone was beginning to ring, but at least Anthony didn't have to take that call, he thought to himself. By this time, he was long overdue for a lunch break after skipping morning breakfast. Walking through the lobby, he began to think about many possibilities when it came to this lucky chance with Gianna Michaels. There was much to think about due to the simple fact she had already booked a stay over the weekend.

Why escort on an island in the Bahamas? Maybe Gianna had some rich clients who would be flying in. Guys who would be willing to pay serious money to spend a few hours with her. Upon another thought, perhaps she was more risking and daring. If Scott was indeed telling the truth, Anthony could only think that she had already went through more than one man at the hotel. There wasn't much he could say about Trey, though Anthony had spent a lot of time with him as a coworker. Not everyone was social and friendly towards conversation like Scott. all that time walking through the halls of the main floor, Anthony thought about how he would approach Gianna. Would she be worth spending an entire paycheck on for the week? It was a one chance opportunity and he felt that it was impossible to pass up. By the time he reached the open entrance into the restaurant, he took a quick peek inside.

Dark red bricks were outside the restaurant inside the building, once housing a McDonalds. The contract between them and the Rosewood Baha Mar had long expired, leaving the hotel with their own bistro inside the main building to be renovated. They still served a similar menu of fast food, but much better cooked and a few dollars more expensive. At least for employees, it was only half price. Anthony stepped through the door way, glancing around the black tables of the restaurant and matching chairs. Off to the right side of the room, he spotted a woman who looked like his last memory of seeing Gianna Michaels on screen. Dark red hair pinned up in a pony tail, showing her pale skin. The woman wore a black top, but it still wasn't enough to hide her massive breasts from underneath. An easy guess that this had to be the legendary porn star herself.

Standing in the distance, Anthony casually observed that Gianna seemed to be finished with whatever food she had ordered. An empty tray only contained balled up napkins and a plastic cup sitting next to it. Her eyes were peering across a smartphone with a large black leather purse sitting next to her. Maybe she was arranging something with a client about now, that would have been his first guess. While he felt confident from his experience in the past with Kelly and Kate, this was a whole different ball game to Anthony. He wished he had worked over the weekends, then he could have had the opportunity to check the woman in himself. The last thing he wanted to do was make a rude introduction for her to blow him off. This was already a chance he had to take. Stepping a bit closer, Anthony decided quietly that he would simply begin a conversation with a friendly smile. As he stepped closer, a pair of big blue eyes shot up towards his face. Gianna had noticed him, prompting Anthony to smile.

"Hi, you're Gianna Michaels right?"

The woman leaned up from the table, smugly grinning as she maintained eye contact and nodded.

"Yeah, that's me. I take it that you're just passing by and noticed me?"

Anthony shook his head.

"To be honest with you, no. My name's Anthony, I work at the hotel."

"Are you some kind of big fan here to offer me room service?"

He laughed.

"No, I heard something about you from the grapevine, let's just put it that way."

Reaching for her drink, Gianna sipped from the straw as her eyes never left Anthony. She pulled it away after swallowing down whatever beverage was contained in that cup.

"I haven't signed any autographs for anyone at the hotel or done selfie photos, if that's what you're about to ask for."

With a slight chuckle, Anthony shook his head.

"Oh no, I wouldn't bother you for something like that. I just heard from a certain someone that you're open for business today."

Her eyebrows quirked as Gianna smugly grinned. Anthony spoke again.

"He just didn't tell me how much it would cost, so I'm left wondering, was he pulling my leg?"

Giggling at his words, Gianna flashed the front of her pearly white teeth.

"It's not gonna be cheap, that's all I can tell you. Are you gonna make a big deal over how much I'm charging like he did?"

"I already know you're gonna break my wallet."

That remark made Gianna laugh again as Anthony forced a smile. She grinned back smugly, flashing her full teeth as if she were hinting to the fact she could eat a man like him alive.

"The going rate is six hundred dollars per hour."

A hefty amount, indeed. Anthony tried to keep a blank face in reaction to hearing that sum. Gianna continued on.

"If you want two hours, I don't want to hear a single word about how I'm getting your whole pay check. My arranged clients have yet to book their stay and I'm charging much more for them. You working guys are getting a discount, if you really think about it."

In silence, Anthony weighed in the options in his mind. Two hours with her, would indeed reduce his paycheck down to breadcrumbs, leaving him with little money until next week. Six hundred bucks being spent on an hour with one of the greatest female porn performers of all time however, was a different tale. That was money well spent, at least in Anthony's eyes. He didn't need to ponder more thoughts to make a decision.

"Six hundred dollars for an hour. Do you take cash or-"

Shaking her head, Gianna cut him off by speaking over him.

"No credit cards or gifts. Cash only. Can you handle that?"

Anthony nodded at her.

"Yeah, but I don't have it on me right now. Can you wait on me to come back with the money?"

She got up from her seat, tossing the plastic cup onto the tray but not picking it up. Instead, Gianna grabbed her purse, slinging the strap across her right shoulder and then clutching her phone. Standing face to face with him, Anthony could now see the dress she wore. It hugged over her curves, pulled just above her knees. Down below, Gianna had on a pair of black high heel pumps, shiny from the lights above. She didn't bother with her trash on the table, almost as if she expected the man employed at the hotel to dispose of it for her. As her blue hues glared back, Gianna's pink lips curved into a grin as her eyes surveyed his body, looking him over. He may have been paying for her services, but Gianna clearly had other ideas in mind.

"I'll give you an hour if you show up to my room with the money. What we didn't talk about was what kind of services you want. I assume you want to do more than just fucking, right?"

Nodding at her, Anthony figured now was the time to get into the hard details of their hour. Of course he wanted to do more than just fuck her.

"Yeah, is a blowjob on the menu?"

Gianna nodded, quick to response.

"And what else?"

He blushed, upon admitting his next fetish.

"Tittyfucking, that's something I always dreamed of doing with you."

"Anything else?"

"Do I get to cum on your face or tits? Or maybe both?"

She laughed at his request, once again flashing her teeth.

"Yeah, you can do that. If that's all you want, this is gonna be quick an easy. I'll give you an hour to meet up at room four-oh-seven."

Turning away, Gianna left him standing there as she began to walk away. Anthony's eyes turned as he watched her thick ass, barely contained within that dress. Cheeks pushing together as she sway her hips, making an exit as the purse dangled beneath her right arm. Outside from the doorway was a chubby man, standing there and peeking in. The dumbfounded expression across Scott's face was enough to annoy Anthony as he let out a sigh and walked closer. Turning to look at Gianna, Scott's lower lip fell again and then he grinned wide.

"Wow! Does she got a big ass or what?"

Anthony didn't hesitate to give Scott a dirty look. The other man was still grinning wide, acting immature for the moment being. When he turned back to Anthony, Scott spoke again.

"So how much is she charging?"

"Eight hundred for an hour."

It was a lie, but Anthony figured his friend wouldn't know the difference. The last thing he wanted was to have to share this woman with Scott like the last two they had encountered.

"Damn, that's fucking expensive. I thought she'd be more mindful to guys like us and give us some kind of discount."

Relieved that he fell for the lie, Anthony just shook his head.

"No, she wants to earn top dollar. I can't help but respect that."

Scott shrugged his shoulders and then slowly curved his lips into a smile.

"I know what room she's at. So are you gonna go up there and spend an hour with her?"

"Yeah, I have to go and get my money to make the payment."

Eyes widening again, Scott dropped his lower lip once more, looking as if he were so shocked.

"Dude! What did I tell you? I swear, you've got all the luck in life. If I had eight hundred dollars, you can bet I'd pay for a good titty fuck and to see that ass clap!"

Random guests walking by turned their heads at Scott's loud words of sexual fever. It was an embarrassing moment, causing Anthony to begin walking forward in a hurry to leave. Scott followed behind him and it was only a matter of time the question came up. Anthony was anticipating him to ask about joining in.

"You think she'd take a discount if I pitched in some money too?"

Shaking his head.

"Fuck no, I already asked. She's charging more than double for threesomes. Sorry man, I tried to get you in."

Another bold faced lie that only made Scott sigh in defeat. Hopefully that would be enough to discourage his pursuit of finding a way to shove himself into the situation. Anthony turned to his friend, offering a subtle smile and nodding.

"Look, I only have an hour with her. Make up the rest of my shift and I'll pay you back later, alright?"

"How are you gonna pay me back?"

"We'll think of something. Don't worry, Scott. I got your back, man."

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1 HOUR LATER

A journey back up to his own room in the hotel had come and gone. Anthony liked to keep spare cash in his wallet, just in case he ever spent it outside the resort. It was rare for him to do that, but for the time being, he was thankful to have enough spare fifty dollar bills to make up a full six hundred dollars. He folded the bills up with a rubber-band and then changed out of his work clothes. The thought of showing up and knocking on her door in the work uniform was a little too much for his mind. More than anything, he didn't want to accidentally bump into a supervisor on his way up to the fourth floor. Changing into a plain old red T-shirt and a pair of black leisure shorts was just enough to make up for clothes that could easily be taken off once he was alone with Gianna. Anthony slipped his feet into a pair of brown leather flip flips before hurrying out the door.

The thought crossed his mind, if he would bump into Scott again. The last thing he wanted was to deal with his friend trying to shove himself into a situation like this. As Anthony walked, he could feel that bundle of cash moving around in his right side pocket, where his phone should have been. Skipping work to complete a deal exchange for casual sex came with the risks, but at least he wasn't missing an entire day like when he was banging Kate Upton. It was good to learn from those past experiences, another reason he felt so confident about trying Gianna Michaels of all women. When the elevator stopped and Anthony stepped out into the halls with other people going about to their destinations, he softly grinned to himself and made the walk up to the door with the numbers 407 hanging above. Anthony raised his hand and knocked three times.