Detective in Red Lipstick

Naked women slept wherever they wanted. Some laid on the grass outside to cool down from the heat, some laid on couches or beds inside. Most still had cum glazed on their faces or chest. They belonged to this private little island, so they could do as they pleased.

The man smoking a cigar was amused by the sight. A place like this had been a lifelong dream, and what else is a man supposed to do with a billion dollars if not create this kind of utopia?

He walked around the island wearing only shorts. Taking puffs of his cigar, he admired the women who had recently been fucked out of their minds.

It was almost dawn and the sun was rising. He waved at the boat which took his esteemed guests back to Miami. Those men fueled his extravagant and hedonistic lifestyle, and in exchange, he made their most deviant fantasies come true.

"Would you like any refreshments, sir?" a woman in a bikini said, whose job it was to provide service.

The man took a puff of his cigar. "No, darling. I've had a busy night and I need some sleep."

"Understood, sir."

He always liked being called 'sir' by his beautiful employees. It was a sign of respect. He kept his eyes on the boat taking his guests back to mainland America.

This lifestyle almost felt like an illusion. His power brought money. His money made him more powerful. It was a vicious cycle. Politicians, celebrities, and business moguls. The ones that knew him were at his service. And if they didn't play ball, he had his ways of making people obedient....

***

The extent of Detective Elisa Wong's deep cover was unlike anything seen before from a female agent. She would surely be studied by future cadets at the police academy.

For now, she settled on three weeks paid leave, courtesy of her superior. After months of intense stress inside of a criminal organization, she needed to crash. It was all over.

Her raven black hair was a mess when she got out of bed that morning. Her home phone was ringing relentlessly when she refused to answer her cell phone. All she was wearing was a skinny tshirt and panties.

"Hello?" she answered in a groggy voice, without even checking the caller ID.

"It's me, get your ass over here."

The Lieutenant was always a prick, but to call her during their agreed-upon time off was just unusual.

"What's gotten into you?" Elisa asked, quickly waking up.

"It's about the Santino family. I have to show you something. So far, only a few people know about this. You need to be one of them."

With the treasure trove of intel she gathered for the police department, she thought she was done investigating that family, which was South Florida's main organization when it came to sex trafficking and narcotics. She was certain she had provided enough evidence to put away Santino and his associates behind bars forever.

"I'll be there in half an hour," she said.

"See you then."

When the Lieutenant hung up the phone, Elisa rushed to prepare herself for action once again.

***

In her jeans and tshirt, she brisked past all the colleagues she'd normally say hello to and made her way towards the Lieutenant's office. There were two other men in the room, huddled around a laptop.

"What's the latest?" she asked, entering the office.

"Detective Wong, come here and take a look at this," the Lieutenant said, then gesturing to the other men to leave.

When the other men left the room, Elisa made her way around the boss's desk. On the laptop was a paused video. It appeared to be of a man and woman preparing to have sex in a bedroom.

"A blackmail tape?" she asked.

"Something the Feds sent us this morning. They recovered it from a raid in Palm Beach. It was on the computer of one of Santino's associates, who still claims to have no knowledge of this. I'm going to play it so you can see the content. It's explicit."

Elisa raised an eyebrow. "This isn't my first time watching porn. Just play it."

"Tell me if you notice anyone familiar."

The Lieutenant tapped the key and the laptop played the video clip. The man and woman undressed. The woman appeared to be in her early 50's, and the man was in his late 20's or so. They got naked. The woman got on her knees and performed oral sex. Then they had rough sex on the bed with the woman's feet flailing in the air. It looked like a standard affair for rough sex, except for the woman's face.

"Is that..." Elisa's voice trailed off as she squinted. "The Mayor?"

The Lieutenant paused the video. "It appears to be a blackmail recording of Mayor Harding fucking some guy."

"Jesus. And you think Santino is behind this?"

"You tell me. Have you heard anything about blackmail? Do you know of any hidden cameras in any of Santino's clubs? You know his style better than anyone. What do you think?"

Elisa thought for a moment. "No. That's not his style. Santino operates in the shadows. He does whatever it takes to avoid law enforcement. Blackmailing a sitting Mayor? Out of the question. He's not stupid."

"Well, as it just so happens, Detective Wong, it's more than just the Mayor."

"Who else?"

"The Mayor's husband, fucking some Hispanic piece of ass. It looks like the same type of residency, the same location. They're a pretty kinky couple. There are a few other hidden sex tapes and we're working to identify the parties involved."

"Who's working on it?" she asked.

"The Feds, me, and you. The DA and the US Attorney's office are hustling to get more warrants. We're working quietly and we're hoping to avoid the media."

Elisa took in a deep breath. "This is some serious stuff."

"Still burnt out from your last job?"

"I'm fine."

"Good, because you don't have a choice," the Lieutenant said. "We need you to go deeper undercover. I know this isn't what you signed up for. I acknowledge that it could be very dangerous. But if we're going to solve this discreetly, it's the only way."

A touch of fear crept through Elisa's spine. She was thankful she hadn't burned her bridges with the Santino organization. She had only disappeared from their radar for two days.

But regardless, she knew them well. As quickly as possible, she contemplated the blackmail sex tape on the laptop screen. Something didn't seem right.

"It won't work," she said, as if thinking out loud. "Trust me, I got all the information I could. These people are careful. I've gone as deep as I could go and I hadn't found anything like this."

"Do you have a better idea?"

Elisa went with her gut instinct, which had never let her down. And if she was right, then she'd be on the verge of uncovering a massive criminal conspiracy.

"We find out who Santino works for," she said firmly. "I'm almost positive that when it comes to this recording, he's just the middle-man."

The Lieutenant kept an open mind. "You're suggesting we cut him a deal."

"Yes, it'll work."

"You must really like the Mayor if you're willing to cut Santino a break after all the shit you went through building the case against him."

Elisa gave a short sigh. "The job is the job."

***

By the next morning, everyone was on the same page. The investigation was kept as tightly-knit as possible. Secrecy was a top priority, and since Detective Elisa Wong had the most experience dealing with this criminal organization, it was only natural that she was the lead person on the ground.

She wore her bright red lipstick, the kind that made her so popular with Santino. For the past few months, she had been an accountant for the mob, assisting to balance their financial books and help launder money.

Her silky, long dark hair was free, instead of the neat ponytail she had worn everyday while undercover. Instead of a suit, she wore a tight tshirt and blue jeans. She preferred casual attire and she always hated the business look.

It was 8 am when she parked in front of the small restaurant Santino owned, where he always ate breakfast alone.

She entered and saw Santino eating by himself. She approached him.

"Ella, my financial girl," he said, taking a sip of coffee. "What brings you here? Can I get you something to eat?"

She stood in front of him, cautious but brave. "My real name is Elisa. And I'm not your financial girl."

It only took a moment for Santino to put everything together. As his facial features moved, Elisa was prepared for any situation. Santino wiped his mouth and put the napkin down.

"I should have known," he said calmly.

She nodded. "Yeah, you should have."

Gently, Elisa put her badge on the table for him to see.

"Sit down. I guess we have plenty to talk about."

Detective Wong sat across the guy whom she had been targeting. "I'll get straight to the point. We have the recording of Mayor Harding."

"Recording?" he calmly said. "I don't know what you're talking about."

"Of course you do. But I don't think that you're the person who made the recording. I think you just transfer the women to someone else, someone with real connections. Someone who can get certain people to feel comfortable, then captures them in compromising positions."

"Now you're talking crazy, detective."

Under normal circumstances, she would have let this banter continue while she slowly reasoned with the suspect. With time of the essence, she needed a harder approach.

"I have an immunity deal for you," she said plainly. "It's best if you get an attorney and start cooperating immediately. If you don't, you're looking at serious prison time. How long do you think you'll survive in prison before your boss decides you're a loose end? Think about it."

"What am I facing?" he asked with a scowl on his face.

"A life sentence, and a seizure of all your assets so there'll be nothing for your family. Because a sitting mayor is involved, they want to give you the stiffest sentence possible so you'll cooperate. And in case you were wondering, yes, I gathered most of the evidence myself."

Slowly, his sour expression turned into a smile. "Good girl. Brains, beauty, and you're slick as hell. You're the perfect package."

"What can I say? They put me undercover for a reason."

Santino's face suddenly morphed and he pulsed with fury.

"Fuck, fuck!!!" he screamed, slamming his clenched fist on the table several times with all of his might.

From the backroom, a burly looking man rushed in and approached their table.

"Everything okay in here, boss?" the large man asked.

"Back off," Elisa shot back, without even looking at him.

The man squared up into a hostile stance.

"Listen bitch, I don't like it when...."

In a flash, Elisa pulled the gun that was holstered from the back of her tshirt, tucked behind her jean pants, and pointed it at the burly man. Her grip was tight enough to suggest that she was willing to pull the trigger.

"Take another step," she said coldly.

"Okay, alright," Santino said to calm the tension, then gesturing to his henchman. "You, wait in the car. Elisa, or whatever your name is, let's talk in the back."

She put her gun away as the man stepped outside. Santino stood up, and without emotion, headed to the back where they could have some privacy.

*

Elisa stared at this once powerful figure, who remained silent for nearly ten minutes with his head hanging down, with a typed letter from a US Attorney offering him an immunity deal for full cooperation.

"I'll do this on one condition," he said in a nearly broken voice.

"You're not in a position to bargain."

"We both know that I'm fucked anyway. I'm compromised, no matter what I do. I've lost my business, my lifestyle. Might as well go out with a bang and maybe repent for my sins. And I want to see how tough you really are. You've got to earn this."

There was a look in Santino's eyes and Elisa knew that this man wanted revenge for having been betrayed by a cop. She knew that powerful men tended to be furious when cornered like this.

She was unmoved. "How?"

"I'm meeting with the guy you're after. The guy who recorded the Mayor getting fucked on video."

She felt the hairs standing on the back of her neck. This was it. This was a major break in the case and she was pleased with her instincts. Being this close to the endgame, she felt a rush of adrenaline and now she was unstoppable.

"When?" she asked.

"Today. I'm supposed to be making a delivery for him."

"Get your fucking lawyer on the phone," she said forcefully. "Take the immunity deal. Then tell us everything."

Santino gave a slight sneer. "Here's what's going to happen. You're coming with me. No police backup or recordings. No guns. Nothing. On the boat ride there, I'll tell you everything. Then, you'll get to meet the person you're after."

She knew Santino well enough to know that this was a final decision. You can't be the head of a criminal organization unless you're ruthless. And this was the most ruthless Santino could be to a police detective. This was clearly Santino's idea of a revenge fantasy, to make Detective Wong step into the heart of the unknown.

"What happens there?" she asked, keeping a straight face.

"Exactly what you'd expect. I want you to see the world he's created. The clients? That's the best part. If I said it, the police might not believe me. But if you saw it with your own eyes, then that's another story."

It was, without a doubt, the biggest decision of Detective Wong's life, and she made that decision in an instant. This was her job. This was everything to her.

"If you try anything..." she said, with her voice trailing off.

"I would never dream of bringing you harm."

Slowly and eventually, Elisa gave a curt nod.

***

Her sights were now set on a man named Rothstein, a man who had been in and out of jail for the past several years. Various prosecutors have gone after him for nearly a decade, but when you have a Guardian Angel looking after you in the form of influential government bureaucrats, avoiding any type of lengthy prison sentence is doable, no matter what the evidence is.

During the boat ride away from the Miami coast, Elisa contemplated everything. Her mind was in detective-mode as she wondered how Rothstein made his vast fortune. No one seemed to know, as far as media reports were concerned.

The sun was in her eyes and the wind was in her hair. She had been given a form-fitting, strapless black dress to wear. It showed off her skinny figure.

And her lips? Before leaving Miami, she put another touch of her famous bright red lipstick, which men seemed to be attracted to. Yes, she was back undercover again. She knew this character by heart. Once again, she'd be playing the role of an accountant.

There were two speedboats which traveled together. Elisa was on the boat with Santino and a few associates. The other boat had the women, who would be providing the sexual entertainment for the night's guests.

It was mid-afternoon when the boats arrived at the shore. The island was tropical and private. No one else was there besides employees and guests.

Following the lead of the sex works, Elisa took off her heels and decided to walk barefoot on the island. Heels would only slow her down. Being barefoot seemed like a more logical approach.

It was her first time laying eyes on Rothstein, who seemed much older now than in the previous mugshots which had been featured on the news years ago. She felt an ominous feeling as they all walked towards each other.

"Welcome to orgy island," Rothstein said in a way that resembled a doorman at any 5-star resort.

The men greeted each other with hugs and handshakes, while Elisa stood closely and observed the small talk.

Rothstein then gestured to her. "And who's this pretty little thing?"

"Her?" Santino asked with a smile. "That's Elisa. She's my accountant. I brought her so she could learn a few things about how a big organization is supposed to be run. You could say I'm grooming her for big things. I hope you don't mind."

"Santino, my friend, you have the best taste in women. You always have."

She watched the grin on the boss's face as he approached her. Their first official meeting. They shook hands warmly. She smiled back.

***

Most of her time was spent in the administrative area, going over finances with Rothstein's people. It was a treasure trove of new information that she had unlimited access towards.

Afterwards, she was free to enjoy herself in designated areas on that gorgeous tropical island. Elisa felt anxiety in her bones as 'orgy island' was underway. The sun was going down. The atmosphere was lively as she could hear laughter from afar.

She got to see everything, except for the rooms and the docks on the other side. A handful of guards kept everything secure. She could hear more boats arriving and her curiosity was at an all-time high. People were fucking already, but who? Who were the clients? Who were in the inner-circle?

Most importantly, she wondered if Mayor Harding had been here too? Was this island the source of the blackmail video which had pulled her back into the undercover assignment?

As she walked barefoot on the grass, contemplating the darkness of this case and how vulnerable she was being alone, a door to a bungalow opened and two women went outside while showing each other affection.

She had met the woman named Mindy earlier, a bronze skinned socialite who kept her brown hair pinned upwards. Mindy was unabashed, wearing a see-through white tshirt with matching see-through pants that showed off her red thong. She was braless and her nipples were hard. There was also a free-flowing Mediterranean style scarf around her neck. She held hands with a college-aged blonde.

"How do you like it here?" Mindy asked, shooing away the college girl, who headed to the main party. "To me this place is heaven."

Elisa politely smiled. "Well, I moved to Miami several years ago for a reason. I love this environment. It's a joy and I can see why you spend so much time here."

"Do you spend a lot of time in the business?"

"It's a new career. The money is good."

"Ever partake?" Mindy asked, raising a suggestive eyebrow.

Elisa pretended to blush. "I've never mixed business with pleasure."

"That's my sin," Mindy winked. "It's all the same to me. I'm in the business of pleasure, so why not indulge?"

In that moment, Elisa realized that she was dealing with the madam of this island; the woman who purportedly ran things and made things possible. The woman who procured and trained women to be sexual servants.

As an undercover agent, Elisa knew how to be smart and keep calm in situations like this. The stakes had never been higher.

"That was an attractive blonde you were with," Elisa said. "So I totally get why you'd indulge."

"Interested?"

"Me? Oh, no. I don't know. I mean, this place seems like a man's paradise. I've heard that things can get.... I don't know... a bit depraved around here."

Mindy laughed. "I'd say that everyone has their inner sexual demon -- both men and women -- and it's something private within that person. Here, we simply give people a chance to live that out. Believe it or not, many of our clients are powerful women who want to play with other women. Everyone has one life to live."

That word triggered something in the detective's mind. Clients. Just who were they? Did any of them know about the secret recordings? Even more desperate for answers, Elisa could feel herself salivating. She was so close, yet so far, to finding out the truth behind this exotic island for the elites, whoever the elites actually were.

"That's a good point," Elisa said shyly. "But I'm the financial woman. I do accounting."

"But you're human, too. A very beautiful human. What's your pleasure? Other women? Mature or college-aged? Cocks? Gangbangs?"

Elisa blushed, genuinely this time. "Cocks."