“I wish you were my mom, Miss Celia,” a thirteen-year-old Jackson once said to her.
“Now that’s not a nice thing to say, Mr. Jackson,” Celia tucked him into bed, “your parents are doing the best that they can.” It was a lie but Celia had to play the role of supportive house servant, and not therapist. She knew Jackson’s parents mistreated their son by doing the worst thing a parent could do—ignore. Nothing hurt a child worse than having an absent parent—emotionally and physically.
Celia sighed and said a small prayer. “Your parents are good people.” That was another lie. She’d found Jacqueline drugged up to the point of incoherence more times than she could remember. She’d discovered Don’s infidelities by doing the laundry and seeing empty condom wrappers fall out of his trousers. She’d worked for the couple long enough to know they barely could stand each other and only appeared as a loving couple in societal functions. Their marriage was very much in name only.
Jackson smiled at his caretaker. She was never a good liar but he knew better than to argue with her. The last thing he wanted was to get swiped with a wooden spoon. “I love you, Miss Celia.” He hugged her.
“I love you, too, Mr. Jackson. Now, go get some rest. You have a big day tomorrow at the game. You’re going to hit a homerun for Miss Celia?”
“I’m going to hit several of them!” Jackson smiled.
“That’s my boy!” Celia got up and turned off the light. “Sweet dreams, Mr. Jackson.”
“Sweet dreams, Miss Celia.”
The memory faded into the background as Jackson stared at the photo of him and Miss Celia he carried in his wallet. He briefly wondered how she would react if she knew what he had become.
No kid grows up and dreams about becoming a pimp. Sure, it sounds fun and it’s the latest thing in pop culture to declare something as cool and hip. Men wearing long fur coats with fingers full of jewelry, a single feather in their hats, and a Cadillac full of scantily-clad women with heavy makeup and the same amount of jewelry as the driver—the pimp—in front.
That wasn’t Jackson, not by a long shot.
He grew up in Calabasas, home to CEOs, Hollywood stars, and famous athletes. His father, Don, was a busy CEO who was never home and traveled twenty days out of the month and entertained his mistresses the remaining time. His mother, Jacqueline, was a socialite who spent more time keeping up the perfect image of loving mother and devoted wife, while nursing a prescription drug and alcohol habit, rather than partaking in any interest in her only child. Jackson could frequently recall the numerous Botox parties his mother had hosted at his home, charming the equally-plastic mothers of his classmates.
It wasn’t always that way. From what he understood from other family members, Jacqueline and Don were brought up in humbled beginnings and were partiers when they were young. Then Don got a fast-track to an investment firm straight out of college and that’s when it all started. He worked his way up from being mailroom boy to CEO within twenty years. During that time, he and Jacqueline conceived their first and only child. Don wasn’t too concerned about being a father as he was about potentially ruling the world and poured all of his energy into the firm. He felt his multimillion dollar paychecks he was bringing home every year was sufficient enough to keep everyone happy and quiet.
It was no surprise that Jackson toed the line of sweet angelic son in front of his parents and hell raiser in the community. With his mother emotionally absent, and his father physically gone, it was money that had really raised Jackson. Whenever Jacqueline wanted him out of the home, she literally threw dollars at him so he could go ‘be busy somewhere and out of her sight.’ Don would shower Jackson with expensive and rare gifts whenever he felt guilty about his actions and, fortunately for Jackson, that was often.
It was his nanny, Miss Celia, an older Southern Black woman who nourished him and taught him right from wrong. She was the one who took him to his baseball games on the weekends and picked him up from school during the weekdays. She helped with his homework and found tutors for him when the assignments were beyond her reach. If Jackson was being rowdy, she was the first to swat him with the wooden spoon she kept tucked away in her apron. Jackson felt closer to her than to his own mother—a fact that had never left his thoughts once he reached adulthood.
When Celia died years ago, Jackson was crushed; crying for days and huddling in his room. He cried at her funeral and found comfort in Celia’s family when his mother shunned him, stating she didn’t want him to ruin her cashmere sweater with his tears.
Jackson shouldn’t have been so surprised when the very next day, a new caretaker by the name of Ana, showed up at his front door as if Celia and her many years of service had never existed. Jackson could honestly say it was that moment troublemaker Jackson died and a new, rebellious, Jackson was born.
He was in and out of trouble starting in his late teens—smoking pot, staying out past curfew, and petty theft. Each time he had gotten caught by the police, Jacqueline would simply roll her eyes and drag herself back upstairs to consume more pills. Don sweet-talked whatever police officer caught Jackson and offered some bribes. And Ana played the role of good house servant and kept her mouth shut.
Jackson decided to get even bolder with his antics, going so far that he needed an attorney to answer charges of DUI while joyriding in his father’s fancy cars. All the attorney did was keep him out of jail and running an expensive tab for Don.
Some called it White privilege or affluenza. All that Jackson knew was he was a rich White kid who had a lot of money and time.
It also made him feel invincible and untouchable.
He grew up watching many of his classmates grow up to become reality stars or famous in some other aspect. Whoever didn’t become famous, became lawyers, doctors, or executives.
And then there was Jackson—rich and bored. His MIT-worthy intelligence could’ve gotten him into any prestigious school in or out of the United States and his trust-fund wealth would’ve kept him afloat forever. Jackson didn’t want to be like everyone else. He just didn’t know what it was that was his passion.
He could vividly recall the moment his life changed forever. One of his friends became a world-famous actor, and hired Jackson to be his personal assistant. Jackson ran errands and did whatever his friend wanted; from grabbing lattes to picking up designer suits for award ceremonies to making late-night drug runs. In exchange, Jackson had unlimited access to other celebrities. He quickly discovered that behind the stage makeup, designer wardrobe, and numerous awards were people who were broken and battered, fragile egos damaged by horrible childhoods and haunting career choices.
He also discovered the same people had kinks that needed to be met.
It was one night after a sex marathon with a Hollywood starlet that a new untapped resource was born. “Jackson,” the young woman moaned and writhed beneath him as he kneaded his hands into her supple flesh, “you have the hands of an angel. I would pay to keep you around just to massage me.”
It was an idea Jackson wished he’d thought of sooner. He loved sex and he loved massages. What better way to combine them both?
So it began—a quest to make his prostitution business legit. First, he would have to become certified in massage therapy. Then, he would have to find the perfect women. They would have to be weak, down on their last dollars, and desperate. Mentally-strong women wouldn’t do because he didn’t want to keep a rotation. No, he wanted these girls to need him and be their brain when they didn’t want to think. He would also have to approach these girls as someone who would legitimately help and not hurt them.
It was by luck that he looked like a Ken doll—blond hair, cobalt blue eyes, a muscular, tawny build, and a schoolboy charm that would make any woman want to drop her panties for him. Many of the items he owned—clothing, cars, and expensive trinkets—were given to him for free, simply because of his looks.
No woman would look at him and think he was a fast-talking pimp who had hoes on a corner. Instead, they looked at Jackson as the guy next door. He was convincing, letting the girls know that he was only trying to help, and if they wanted to leave, they could anytime they wanted. He was the shoulder to cry on, the counselor whenever there was a problem, the disciplinarian whenever there was an issue with the girls. With the perfect smile and soft dimples in his face, Jackson looked endearing and safe.
Of course, being reckless in bed didn’t hurt, either. Jackson had a reputation of bringing his conquests to multiple orgasms and making them sore for days long after a night with him. His oral skills were as legendary as his cock, making a woman sing as she held his face down in her nectar and rode his tongue to many orgasms throughout the night.
He wasn’t a pimp. He was a stockbroker, if you will. Just as a person would watch the stocks to see how their money is doing, Jackson eyed his girls to make sure they acted right. To him, he was merely a protector of his investments.
And his investments were managing his personal massage business. High-class executives, Hollywood actors, musicians, athletes, and regular Joe Schmoes would call up Jackson’s service to set up an appointment. The girls would go to the client’s house, render any services, and return home to Jackson, with a large wad of cash in tow. It was always discreet and untraceable, especially back to Jackson.
He was sure some person in a white coat with a couple of letters at the end of their name would tell him that his issues with women were related to his mother and the massage business was a fuck you to her in some form. They were probably right.