The Cabana Boy

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Status: Finished  |  Genre: Other  |  House: Booksie Classic

A manipulative young man gleefully exploits the rich and elite. But what motivates his sinister actions?



Caleb stepped off of the ferry that brought him to Bald Head Island. It was a bustling holiday weekend. The island was packed with vacationers and residents looking to enjoy the Forth of July and the hot sunny weather that accompanied it. Caleb made his way past the droves of people to a golf cart that would take him to the Bald Head Island club. A club reserved for the rich.


Caleb was only 17 years old, but he looked older than that. He used this to his advantage to pass himself off as 21. Caleb had a busy day a head of him, and one that would likely prove to be very profitable. For today Caleb was working as a masseur. Caleb grabbed the last seat on the golf cart bound for the club. The driver set off as soon as Caleb boarded.


The driver was forced to slowly meander around the crowds of people spilling out from the bars and restaurants. Live music filled the hot summer air which was complemented by the smell of grilled burgers and hot dogs. American flags proudly wafted in the gentle breeze from each and every bar and restaurant.


Finally the driver was able to get clear of the crowds with mostly an open road ahead of him. This provided a welcoming breeze as he sped towards their destination. Caleb's thick mane of dark brown hair blew around during the windy ride. Caleb was dressed in a crisp blue polo shirt and cargo shorts, along with a pristine pair of athletic sneakers.


Finally they arrived at the club house. Caleb stepped off of the golf cart, his shirt already sticking to his back due to the midday heat of July. He headed towards the pool where he would meet his first client of the day, Dorthy.


Dorthy raised her glass upon seeing Caleb. “You are finally here!” Dorthy exclaimed with a lecherous tone. Caleb responded with a smile that masked his discontent. As Caleb approached Dorthy he could see she was already inebriated, and it was only mid afternoon Caleb thought to himself.


Dorthy laid down on her Beach lounge chair in a almost sexually suggestive manner. As Caleb readied himself for her deep massage, Dorthy barked out a drink order to the nearest cabana boy. Caleb dug his strong fingers into her lower back. As Caleb moved his hands further up her back he noticed her overly tan skin was dotted with sunspots, or maybe they were age spots as Dorthy was well into her fifties. Dorthy turned her head to the side and rested it on the chair. She was grinning from ear to ear. As Caleb continued with the massage Dorthy's already loose grip on her drink loosened even further as she sank ever more deeply into the lounge chair.


Caleb brought his hands up to Dorthy's shoulders and massaged them deeply. Causing Dorthy to exhale “Mmmmm...” Caleb stared at Dorthy as he worked over her body. Her age showing even more through the wrinkles her leering smiled produced. A feeling of revulsion crept into Caleb. He imagined his hands wrapping around her neck and wringing the very life out of her. Just then the drink slipped out of Dorthy's hand and shattered on the stone patio ground. Agitated Dorthy again ordered a cabana boy to immediately bring her another drink.


With her massage session concluded Dorthy sat up and composed herself. She reached into her purse and pulled out a large sum of cash. She brazenly pulled Caleb to her by grabbing the waistband on his shorts and stuffing his pay into them. “You better go now.” She said breathlessly. Caleb thanked Dorthy and as he walked away she ogled him until he was out of sight.


Caleb made his way to his appointment with Mrs. Davenborough. She was the 4th wife of the extremely wealthy Mr. Davenborough, a man well into his seventies. Like many of the Caleb's clients Mrs. Davenborough was much younger than her husband, by well over 20 years. Also like many of Caleb's clients Mr. Davenborough could no longer please his wife. Caleb provided his “services” to Mrs. Davenborough as well as other wealthy women who were enduring the same embarrassing flaccidity suffered by their husbands.


Caleb took great pleasure in exploiting the rich. His involvement in extramarital affairs brought him a great sense of schadenfreude, because he knew he would play a part in ruining their marriage. He would please these women in ways they have never before experienced, or ever would again. He would toy with their emotions and manipulate their behavior until he had these women completely under his control, whether it be brazenly or with subtlety. And then he would spring his trap, unveiling his guise.


Caleb himself was born to a very wealthy, but very married woman. An extramarital affair that threatened to humiliate the esteemed and respected Potts family. Caleb never knew his father. There were whispers he may have been a care taker or even a cabana boy. There were even rumors that he was paid an extravagant sum of money to simply disappear.


Caleb was the dirty family secret. A reprehensible stain to the families reputation. He was discarded like trash and passed from one family member to the next, they all rejected him. Caleb was bounced around from one orphanage to another, even foster homes. But he would never enjoy any kind of normality in his broken upbringing.


As Caleb continued on to his destination he thoughts were interrupted by the sound of music. A authentic calypso band was playing under a pavilion outside of the hotel he was heading to. It was a large band and though Caleb was no expert when it came to music, he could tell the band was talented.


A heavy set black man who looked to be well into his forties was playing lead guitar. He was actively engaging with the rich elites who had all gathered around the pavilion. Strutting into the seating area he playfully showed off his mastery of the guitar for the hotel patrons. His fingers were almost a blur as they effortlessly strummed the guitar strings. He was grinning from ear to ear as he played, exposing a full set of white teeth.


But it was then Caleb noticed a rather subdued young man who was maybe the same age he was. He was playing bass guitar under the shade of the pavilion. He lacked the older man's enthusiasm and a look of revulsion soured his face. Caleb figured he was likely the older man's son. Caleb would be correct.


The young man's name was Benjamin, but he went by Ben or affectionately by Benny. He like his father was a talented musician. However Ben resented his father for the way he played into the hands of the rich, much like a toy for their amusement. To Ben his father reminded him of an organ grinders monkey and he loathed him for that. He stared at his father as he continued to play with the sweat collecting in his furrowed brow and the weariness in his eyes. Finally Ben turned away a look of discontentment mired with shame set upon his face.


Caleb understood what the young man was feeling. He felt that they had a sort of bond, even if the young man was completely unaware of it. Caleb made his was into the hotel. It was time for his appointment with Mrs. Davenport.


Caleb knocked on the door of the hotel room and Mrs. Davenborough immediately answered. She was clad in only a sheer nightgown and upon seeing Caleb she smiled excitedly as her face flushed red. She offered Caleb a drink which he politely declined.


Despite her age Mrs. Davenborough was still an attractive women. Though this was most likely due to her numerous cosmetic surgeries and dental work. She had however kept herself in shape. Her revealing nightgown showed off her toned thighs and firm, flat midriff. She smiled at Caleb as she threw back her drink and then walked up to him, embracing him like a lover.


She pressed her body firmly into Caleb and slid her thigh up against his crotch. She wrapped her arms around Caleb's shoulders and kissed him deeply. Her breath was warm and Caleb could smell the alcohol on it. In another moment they would fully engage in their act of infidelity.


Their bodies were intertwined under satin sheets. They lay there together for a moment before disengaging from their lustful embrace. A sheen of sweat covered their tone bodies as they slid out of bed and began to get dressed. Mrs. Davenborough giggled as she slipped on her nightgown.


She stood on the side of the bed and was about to embrace Caleb when she was hit in the chest. A spray of crimson splattered onto the pure white satin sheets. Shocked both Caleb and Mrs. Davenborough looked up and saw Mr. Davenborough standing just inside the room holding a gun with an Obsidian silencer. Mrs. Davenborough was about to say something, but before she could get the words out Mr. Davenborough fired again. This time he hit her right in the head. Her lifeless body slumped to the floor.


Mr. Davenborough said nothing. He lowered the gun and seemed to be in shock over what had just transpired. But then he regained his composure and fixed his aim on Caleb, though his arm was noticeably trembling. Caleb however stayed calm and did not move.


I can understand you being upset Mr. Davenborough.” Began Caleb. “You have every right to be. However what you have done here is murder. This cannot be undone, but it can be made worse. You see I am only a minor. Murdering me would only further sully the prestigious Davenborough name. Caleb slowly walked a few steps closer.


Yes I am well aware of the Davenborough name.” Continued Caleb. “Your family has lived here for generations. Pride and prestige accompany it. But you are still a murderer. Though with your wealth and social standing it is probable you will avoid prison. Despite this you will probably see time in court. Additionally you will still have to endure the humiliation you have brought to your family. Your peers will lose respect for you. People will talk, word will get around. You will very likely be ostracized by your family. Maybe even committed to house arrest for your remaining years, the few that you have left.” Caleb hesitated to let his words sink in.


Though there is something you can do, something that will lessen the shame you have burdened your family and name with.” Added Caleb. You can take your own life. It would be a brave and honorable course of action. It would spare your family of disgrace and preserve the integrity of your name.” The elder patriarch didn't say a word. He still had his aim fixed on Caleb. The sound of the calypso band could be heard ever so slightly as the two men stared back at each other in silence. Suddenly Mr. Davenborough raised the gun to his temple and pulled the trigger, killing himself instantly.

Caleb stood there for a moment to collect himself. He finished getting dressed and turned to the night stand next to the bed. There was a envelope stuffed with cash. Caleb's eyes widened as he was quite surprised by how much Mrs. Davenborough had paid him. Caleb carefully stepped over the Davenborough's bodies and quietly exited the room.


Outside Caleb observed the calypso band still going strong. Though some band members had changed the father and son were still playing. The father appeared exhausted, yet he played on with that smile fully intact. Caleb walked up to pavilion and upon observing the tip jar he shoved several hundred dollars into it.


Benjamin looked at Caleb with shock written all over his face. He responded with a friendly nod. Caleb then stepped away from the pavilion and walked away into the starry night as the music faded away behind him.





Submitted: May 23, 2021

© Copyright 2021 Jason Scott. All rights reserved.

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