The undercover operation felt like the perfect storm because everything seemed far too easy. And in her experience, it was usually the perfect plans that led to the biggest disasters. Taking down a criminal organization is never simple.
Detective Elana Martinez had assumed the secret identity of a high value female target. Someone of great importance to the criminal underworld.
Now here she was, at an exclusive resort in Miami, sprawled across a lounge chair by the pool wearing nothing but a barely-there bikini that highlighted her natural curves. Margaritas and fresh fruit were being served to her by the staff.
She took a moment to enjoy the sounds of the other guests having conversations or diving into the pool. They were completely unaware that this resort was owned by a crime syndicate. And it was a great money laundering operation, too.
A short distance away, just around the corner of this extensive property, she could hear the sounds of people having sex in the open air. This was one of the perks of an exclusive resort. People could do as they pleased, which included having exhibitionist sex in the pools or spa areas.
Before taking this job, she was on the verge of retirement from the police department. She had already accepted an offer working for her sister's design company. Sure, it would be a much less exciting lifestyle, but the money was good and there was little stress.
As fate should have it, she was the only woman who could do this job. Being a middle-aged Latina with the right figure made her the perfect fit. This was a joint-operation with the FBI and the stakes were enormous.
Her concentration broke when an employee of the resort approached her in an unassuming way.
"Ma'am, your appointment is ready," the employee said casually.
Elana maintained the bitch-face of a spoiled rich woman. "Good. Take me there."
"Please, follow me."
She got up and covered her body with a thin embroidered wrap and slipped her feet into designer sandals.
To anyone else, it sounded like a massage appointment or anything relating to the many high-end services this place provided. But it wasn't. Together, they went inside the hotel and took the elevator down to the lower floor. This was a major step towards the detective's penetration into a criminal network.
When the elevator door opened, the atmosphere was totally different from the rest of the hotel. Here, there were blue lights which were dimmed and soft music played in the background. There were hot tubs large enough for groups to use in private, presumably for sex.
They went further down the walkway. There was a door that required a password, which the employee entered.
Inside that room was dark, with blue lights, and what looked like a small pool. Nothing else.
"Remove your clothes," the employee said. "You'll swim in the pool. There's a short tunnel in the water that will take you to the secret room. That's where the main computer is."
"Sure. We can never be too careful about things."
Elana stepped out of her sandals and pulled her embroidered wrap away, letting it fall to the floor since there was nowhere else to put it. She was about to dive into the pool before she was stopped.
"Ma'am, you'll have to remove everything," the employee said calmly. "No bikini. You'll need to be naked and I'll have to give you an inspection."
She gave a bitch-face and glared for a moment. "Excuse me?"
"New security measures. I'm certain you must have been informed of this at some point."
Elena had been briefed on a lot of things, but not this. At that very moment, she could imagine the female prisoner laughing in a small cell, knowing the kind of surprise the detective was going through.
Nonetheless, she was here to do a job. Although getting naked is never part of anything a detective would sign up for, at least no one would know about this. Everything happening here was unrecorded and the employee, who'd be the only witness, wouldn't be arrested.
Detective Martinez kept her game face and pulled her bikini top away. Her role was being a powerful crime figure who was accustomed to accessing this computer, so she acted the part, showing no fear whatsoever. The bottom came off next.
She stood completely naked before this unphased employee. Her brown skin still shining from the tan and sunscreen. Her curves on full display. And her dark nipples even turned hard from the small rush of excitement she got from this.
"Happy?" she asked, hands on her hips.
"Turn around and bend over. Once everything checks out, then I'll be happy."
A smile crept across her lips as she turned around. She had to admire the dedication of this bland looking employee, who appeared accustomed to dealing with powerful figures in the underworld.
Once bent over, she spread her butt cheeks to get this over with. There was no point in arguing anyway. No one would ever know she did this, and this was one small detail she'd gladly leave out of her reports and debriefings.
A finger prodded her vaginal and rectal area for recording devices. When nothing was found, she was given a gracious smile, along with clearance to use the computer.
Elana dove into the pool. Underneath the water was a small tunnel and she swam through it. On the other side, she emerged from the water, into an empty room that was dimly lit. Nothing was there except for a table, a chair, and a computer.
With water dripping from her naked body, she sat in front of the computer and had access to a fully encrypted network. This was where international drug gangs communicated and listed their routes, prices, and distribution methods. Using a method like this was a lot safer than meeting in person or using other forms of electronics, but it made them vulnerable to women like Detective Martinez.
She always had an excellent memory and she tried to remember as much as she could, repeating key points in her mind. There were tens of thousands of different messages and she focused on what she could. An undercover job like this was left to her discretion.
'You people are fucked,' she whispered beneath her breath, taking a final round of memorization from the screen.
Her role was essentially that of an IT (information-technology) woman. Someone who made sure the computer and mainframe ran smoothly. It was clever to have a woman do this job, she thought, because no one would ever suspect a woman of having this much knowledge about the system.
Returning to the other side, she was greeted by the employee who was holding an outstretched towel for her.
"Such good service," she smiled, wiping water from the eyes as she stepped out of the water naked.
"Anything for you. Will you be returning? Or is the job complete?"
"I want another look tomorrow. I'll come up with a specific plan to find security flaws in this system. Once I'm satisfied, then I'm done."
Elana kept her hands up while the employee wiped her body dry with the towel. She put her bikini on, and while still feeling titillated from her nudity, she went straight to her suite to transmit the information.
Diego leaned back and took a puff of his Cuban cigar while watching the monitor. Not many people on the hotel staff knew what this office was for, because this was a very unofficial job from the hotel's upper-management.
The man's dark, cold eyes examined the naked woman on the screen, watching this woman drive into the water to perform maintenance on the organization's computer. In this line of work, everyone must be closely watched.
"Come over here a minute," Diego said to his right-hand man. "Anything catch your eye?"
The other man was named Cutter. They both watched the screen as a mature Hispanic woman, water dripping from her body, performed maintenance service on the machine which contained information that could put hundreds of people in prison for a very long time.
"Nothing unusual, boss. Other than that nice set of tits."
Diego puffed his cigar. "She's too calm. Too collected. Too fast."
"Ain't that what she's paid for?"
"Look at her hand speed. Notice her face glued to the screen. Maintenance people usually work slowly and carefully. This woman is looking through our files."
Cutter looked again. "You've got a point. Feds?"
"I've never heard of a Fed or a cop getting naked to perform a job. That's partly why we have the nudity requirement."
"It could be our enemies, then."
"We can never be too careful," Diego said, taking a long puff of the cigar.
"How should we handle this, boss? The bitch is staying in a suite. I can go over there with a couple guys to sort things out. Make sure everything is square."
"That could be dangerous. We don't know who she's associated with. She doesn't look like any cop I've ever seen, but she moves like one. Quick hands and fast eyes."
"A cop with tits and ass like that?" Cutter smirked.
"They're desperate. Anything's possible. We have to be careful."
"I can call our friends below the border and see what they think."
They both knew that it would be pointless. In this business, hiring a tech person can be like hiring a hitman. It's often anonymous so there's always deniability if anyone gets caught. Besides, he didn't want to seem jumpy in case he was wrong.
"Ask our friends down south about this woman," Diego said with his eyes sharply fixated on the screen. "There's gotta be something that identifies this woman. Maybe a weakness of some kind. Or a trademark."
"You got it, boss."
Before Cutter made the phone call, both men observed the screen and watched the naked woman dive into the water, exposing a rear end which they found to be delicious.
The nightlife of the resort was something to behold. The joint task-force was thrilled with the information she had sent and the plan was still operational. She remained in character as she enjoyed the nightlife. She knew she was being watched since the moment she had arrived. Detective Martinez was playing a high-flying woman of expensive taste, so she acted like it.
On the government's dime, and wearing a tiny black dress, Elana ordered the most expensive drinks and did plenty of gambling at the cards table, losing a few thousand dollars in the process. Then she went outside to enjoy the ocean view. Music played while the guests flirted and spent time in the outdoor hot tubs and pools.
She ordered another drink and laid across a lounge chair to observe the party. In truth, this was the best vacation she'd ever had, as a place like this was far outside her financial range. And if she were truly honest with herself, she'd miss the thrills and danger of this job. So she took a moment to enjoy the final assignment of her career.
"Having a good time?" a man asked.
Looking up, the detective was unimpressed by what she saw. The big guy looked like a classic sleaze. She had been hit on several times by men since the moment she had arrived here. This was different. The man clearly wasn't a guest because he didn't look sophisticated. She remained on guard.
"Seems like it," Elana said, taking a sip of her drink.
"That's good. You're a beautiful woman. You look lonely, sitting here all by yourself."
"I'm here on business. And I'm doing just fine."
Elana knew that this man was part of the organization, just from the way he presented himself. The man was a brute. Pure and simple.
"Computer business, by any chance?" the man asked.
There was no point in denying it. "Yes, I work in technical assistance."
"My name is Cutter," he grinned. "Pleasure to meet you."
"Hello, Cutter. What can I do for you? For the record, I don't usually speak directly with clients."
Cutter sat on the empty seat next to her. "Relax, honey, this ain't about business. This is about, let's say, your comfort. I'm a customer service guy."
Having been in this line of work for a long time, Detective Martinez knew that this wasn't good. She saw the gleam in Cutter's eyes and noticed a slight tenseness in his voice, as if he was planning something. Remaining calm, the detective projected coolness.
"I'm fine," she said in a reassuring tone. "The drinks they serve here are divine. And the atmosphere? I could get used to this."
"Ah, but there's always more. I know your reputation, Rosa."
A chill went down her spine when the man used the code-name. She had already gone over the ins-and-outs of this character. The real Rosa had already given up so much information while in police custody, but Elana knew that criminals always held back information.
"Oh? Hopefully you haven't heard too much about me."
Cutter remained vague, "Don't worry, hun. I know how this works. No one knows your real name. It's all hush-hush. I love a woman of mystery."
"Then it should stay that way. I'm here to do a job. I've conducted a preliminary review of the mainframe and I'll delve deeper tomorrow."
"Sure, but I've been told you enjoy a good time," Cutter replied. "And I've also been told to be at your service. You know, compliments of the resort."
Elana held up the glass. "This drink is more than enough. Thank you."
"I heard the real Rosa fucked all the nearby men on her last job. You know, a nice hard group fuck. Porno style. She apparently said she can only get off if she's got multiple dicks in her."
There was a twisted grin on Cutter's face, which only meant bad news. This was a topic that Detective Martinez had been briefed on. She knew that their subject was heavily into group sex. Everyone in the department knew it because it had been caught on surveillance weeks before the big arrest.
Familiarizing herself with every detail was part of staying alive for an undercover operation of this level. That's why she didn't deny anything. She had to remain cool. And more than anything, she had to remain firm and in control. Experienced operators like Cutter can smell fear a mile away.
"Are you saying I'm lying?" Elana questioned.
"I'm saying Rosa is a classic Gangbang Queen type of lady. And since we're such gracious hosts, we figured we'd extend you a little courtesy."
Despite the lascivious grin on the man's face, the detective knew a veiled threat when she heard one. Somewhere along the line, something had gone wrong. Now suspicions have been raised. And with men as dangerous as this, she had to make the right moves.
In her experience with undercover work, maintaining a strong position is essential. When criminals raise suspicions, it's because they aren't totally sure if they're being betrayed or not. Because if these people were certain, then she'd have already been killed in the hotel room earlier.
"Yeah, that's me," she said firmly. "But I don't fuck around with strangers. I don't mix business and pleasure. I'm not an idiot."
"So you're a business woman?"
"I'm being paid to do a job. Just like you. Got it? I don't fuck at work. And I certainly don't fuck because you're telling me to."
She made her point loud enough that a few nearby people had heard the comment, but she didn't care. Being raised in the streets of Los Angeles, a woman like Elana knew how to handle men like this. For a few seconds, she thought it worked. Cutter looked dazed and outwitted. But then again, men like Cutter follow orders. They don't give up because they aren't allowed to.
"Alright, listen," he said, enjoying the woman's feistiness. "We can compromise. I'll get some of the hotel workers to come fuck you. Everyone wins."
"Is this a test? Are you testing me?"
"It's our gift to you."
Knowing he had the upper-hand, Cutter reached out and gently used a finger to trace the curves of Elana's breast through the thin black dress. It was brazen and anyone could see it, but this was an exclusive resort for adults and there was already lots of friskiness going on around them.
"I don't like having my integrity questioned," she said, in a tone which suggested that she knew this was inevitable.
Cutter leaned forward and whispered, "Too. Fucking. Bad. Rosa has a reputation for being a sex maniac. So that's what you're gonna get. Shouldn't be a problem, right?"
"You have no idea what I'm capable of."
The intensity of the detective's gaze matched this mad man's. Even at her age, she still had her edge. If she had shown an ounce of fear, then it would all be over for her.
"Take it all off," he said, licking his lips. "Right here, right now. Get comfortable someplace. I'll be back with a few friends, since obviously you love a good gang-fuck."
Surely this was a bluff. It had to be. It seemed illogical that a sophisticated criminal organization would draw so much attention to themselves. But then again, the stakes were high and her undercover identity seemed in doubt. This was a surefire way to find out if she was really who she claimed to be.
Keeping the same intensity, Detective Martinez stood up with her eyes still locked on Cutter. Then she pulled at the shoulder straps of her dress, letting the expensive attire fall to the floor as if it were cheap fabric.
But when Elana unclipped her bra and shimmied out of her panties, heads turned. She stood naked in her heels for people to admire. She ignored everyone. Her audience was Cutter and whoever in the organization was watching. And she was certain that other associates were watching.
"Even better in person," he grinned widely, eyes going up and down.
She kept her hands on her hips. "So you watched me on a hidden camera earlier. It's not very polite to spy on a woman while she's naked."
"Hey, we can never be too careful," he shrugged, but not caring at all.
"Fair enough."
Hoping to call the man's bluff, she turned around and walked over to the pool area. Eyes leered in her direction from men and women, but she kept ignoring them. This was work. This was her life on the line and she had to play her cards right.
She knew the risks before accepting this job. No one could have predicted a situation like this, however.
Taking a naked walk to the pool area, Detective Martinez took solace in the fact that she'd never, ever see these other guests again. This was a one-time deal and she'd be gone after tomorrow. In a couple months time, this organization and its affiliates would all be arrested.
Standing in front of the pool, Elana took her heels off and entered the shallow end of the pool using the stairway. She figured it would be a slight deterrence for whatever Cutter was planning. She was still fairly certain that this was a bluff. If it wasn't, then she did everything she could to avoid being killed by these men.
Elana could feel many sets of eyes gazing at her body. It was an exhibitionist rush to be admired this way. She had never done public nudity before and kept reminding herself that no one would recognize her. No one would ever see her again once she quit the job and returned to civilian life.
In the background of the outdoor beachside party, she could hear the sounds of sex. Other couples, perhaps swingers on vacation, or people trying it for the first time, were having intercourse.
Detective Martinez felt nerves in her stomach. She couldn't bring herself to look at Cutter. She did a seductive twirl in the water to show that she was the real deal. The woman she was posing as had a reputation for having a ravenous sexual appetite. Everyone in the Department knew it. So she had to play the part.
After several moments of entertaining the guests with her tits, she wondered why Cutter had gone quiet. Had the henchman had enough of these games and just left without saying a word? Doubtful.
That's when she saw it. Cutter had returned with 4 men who were still dressed in their employee uniforms. Two were white, one was black, and one was hispanic. The men looked excited at the prospect of getting to fuck her, but also had a sense of disbelief that this would actually be part of their jobs.
"The pool, eh?" Cutter smirked. "That'll do."
Detective Martinez sucked in a deep breath and forced herself to give these men a smile. In a split second, she had resigned herself to the fate of having sex in public with a group of strangers.
Her pussy clenched in anticipation. This had long been her fantasy, but under much different circumstances. She had always imagined a group sex setting to be tender, romantic, and great fun. Most importantly, in the privacy of a room.
Ignoring all the resort guests who were watching this, Elana turned around and laid her forearms on the concrete, resting her chin on her arm. She was in the shallow end of the pool and she stood with her legs spread apart, offering her pussy to these men should they accept it. A part of her still wanted to think that this was still a bluff, but that seemed unlikely at this point.
Listening to the background music, people having conversations and sharing laughter all around, along with the distinct sounds of sex nearby, Elana also heard the sounds of these men undressing. Belt buckles were being undone and there were clacking noises from the buckles hitting the concrete.
Water splashed and waves struck her body from the men entering the pool. They moved towards her direction.
"You guys have her pussy," a man with a deep voice said. "I'll sit on the edge of the pool and take her mouth."
Cutter answered, "That's how this woman likes to cum. With her holes filled at the same time."
There was a wicked sense of delight in Cutter's voice, like he now cared more about watching a group-fuck than actually doing his job to find out if she was an undercover agent. That wasn't a big surprise. Sex is the downfall of a lot of powerful men.
Detective Martinez arched her back so that her ass would be pointed to them. Her legs were in the water but her shapely rear-end was sticking out. She didn't bother to entertain them or do anything sexy. Her big ass was enough for their enjoyment. It always was for any man.
On cue, a set of hands clasped her waist and moved down to her butt, cupping her bottom. She was given a good squeeze and she knew she was moments away from behind fucked by this guy. Whoever he was.
"I'm a busy woman," she said to the mystery man, still looking away from the men who'd fuck her. "Be quick about this. Have your fun and appreciate that you've ever had me."
"Lady, with a body like yours, no one can last long."
"Same as it ever was."
Detective Martinez laid her head to the side, on her curled arm, and felt the man penetrating her pussy. The guy did what he could to make an easy entrance, but clearly he was in a rush, either because of her warning or because he had to go back to work.
While the man started fucking her pussy, Elana did what came naturally to her -- she focused on her police training. Years in the police academy had taught her that her body and mind were capable of anything. That she could endure all sorts of physical and emotional stresses.
Pool water splashed and waved all around her as the stranger fucked her from behind. As much as she tried to focus on her training, this was uncharted territory for any officer on the job. Getting fucked in public was nothing like enduring a grueling physical exam or getting shot at on the streets.
Her pussy was on fire and she was a woman in heat. She tried not to fuck back. She tried not to give in. But why fight it? She was playing a role and she needed to look the part, allowing her hips to bounce back, fucking the man in return. Allowing herself to moan and enjoy the raw feeling in her pussy.
Elana's trance was broken when a black man, who was naked from the waist down, sat on the edge of the pool, right in front of her. She had to move her arms to make way for the man to sit. His erection was pointed in front of her face.
"The boss says you love to suck," he said. "And that you like your holes filled at the same time. Well here you go."
Still being pummeled from behind, Elana remained steadfast. She needed to act like this was the most natural thing in the world for her. She needed to project confidence and experience, the way any seasoned porn star would. Because the woman she was posing as -- Rosa -- was well-known for an insatiable sexual appetite.
"Let's hope you taste as good as your margaritas," she answered with a steady voice, suppressing her moans.
Her body was still rocking back and forth, and when she took the hard cock in her mouth, it was the first time she'd ever had two men at once. She sucked the dick with the same diligence as she was handling the cock in her pussy. Her head bobbed up and down with the same rhythm that she pushed her hips back.
The line between her personal life and her undercover assignment had been destroyed. This was dark territory. Something seared into her memory and it would always be a part of her. She could feel herself starting to sweat from the intensity in her core. She could hear the chatter from the guests who were observing the show.
But in her immediate area, the loudest noises were the splashing water, the guy slamming into her backside, and her own slurping noises. Sounds which would forever remain in her thoughts.
"You've got one hell of a mouth, babe," the black man said, using both hands to stroke her long hair, pulling her head down even deeper.
Elena had always been fine with this sort of foreplay and even a little rough sex. But when she felt the other men mauling her breasts with their hands, it became overwhelming. Her senses were under assault. The hands became rougher on her body, twisting her big nipples, squeezing her hips, pulling her head down so that she'd suck it even deeper.
When she heard grunts coming from behind, she knew the man was about to cum. She didn't say anything. Not with a cock buried in her throat. She didn't want to make a scene either. Being anything other than a gangbang lover would make her look suspicious.
So when the grunting man ejaculated in her pussy, she allowed it. She kept on sucking while being pumped rapidly from behind. It was the most degrading experience of her life, but somehow, the thrill of it made her heart race.
"As expected," the man said, finishing off his last set of thrusts. "Your cunt made quick work out of me. Enjoy the rest of your night, ma'am."
When the man pulled out and slapped her butt, Elana felt a gaping sensation in her pussy, along with cum leaking from her vaginal canal, down her thighs. She knew globs of cum would soon be floating on top of the pool.
Hands released her breasts, and while still sucking on a cock, she could feel water waving from the men shuffling around. Presumably the other men were figuring out who'd fuck her next. Elana wondered if they'd be squeamish being inside of her now, since another man had already cum there. But then again, she knew what kind of body she had. She knew men would be forgiving of that, just to be inside of her.
In a matter of seconds, she was being fucked again. The next guy didn't care that her pussy was filled with cum. It was back to the same sexual routine. Her breasts were mauled, nipples pulled, and she swirled her tongue around the head of the dick.
For the next few minutes, these men used her however they pleased. Elana would never admit it, but this was a life changer. It was one thing to have to fuck a criminal, but doing this for hotel staff was something she could live with. And doing it for the audience around the pool was euphoric. She had never felt so dirty in her life.
The inside of her pussy was overflowing with cum when the men took turns filling her up. Her labia felt glazed and she already had two orgasms. Meanwhile the guy in her mouth took his time, slowing things down whenever he got close. He wanted to savor the experience of fucking Elana's beautiful face.
When the men finished with her pussy, all that was left was the dick in her mouth.
"I'm going to cum," the man pumping her mouth said. "Look me in the eyes. I love that."
Elana looked up while sucking, giving the man what he wanted, which was power over her. He stroked his dick while sitting there, and soon, the detective's mouth was filled with cum. The first shot hit the top of her throat and the rest coated her tongue.
She waited until the man finished and stuck her tongue out, showing a mouth layered with cum. Then she swallowed most of it with one gulp. The second gulp cleared her tongue and she licked around her lips.
"Get back to work," she said with a slight attitude, sticking to her role. "I'm sure you'll always remember this night."
The men tried thanking her, but she didn't care. Instead, she leaned back into the water and did backstrokes in the pool, letting cum ooze out of her pussy and float all around her.
Cutter stood watching, "You live up to your reputation. I'm impressed."
"Like I said, I'm here to do a job. If you wanted a show, you got one. But don't ever question my integrity again."
Elana sat on the stairway at the shallow end of the pool, with only her feet and calves in the water. Her breasts were on full display as she outstretched her arms alongside the concrete. Her legs were open and her pussy showed. It was the final act of easing whatever suspicions this organization had of her.
"Yeah, alright," Cutter nodded, accepting everything he had seen. "I can respect that."
"Good, because your network needs more work, and I'm the woman you need."
She licked the excess cum from the sides of her lips to spellbind him. In her post-orgasmic haze, she looked away from Cutter and towards the guests of this resort. They all had a good time with their drinks in hand, enjoying the lavish lifestyle, and being thoroughly amused by the public gangbang they had just watched.
The information received was a treasure trove. It was far beyond what anyone had expected and they were thrilled. There'd surely be several rounds of big promotions after all the major arrests have been made.
Detective Mason kept a straight face watching the live surveillance stream of the resort. Everyone in the operations room kept a straight face, too. But during break or after hours, all anyone could talk about was Elana.
They watched their undercover agent sitting naked under the morning sunlight, sipping a margarita by the pool. Every man in the department had long wanted to fuck her. None succeeded. This was the next best thing. They were eager to see if she'd perform another 'test' as the organization liked to throw bait her way.
Sure enough, to the delight of every man in the operations room, they watched a resort staff member approach their undercover agent. The man was in his late 40's and placed a drink beside her. Standing beside her, the staff member undid his pants and freed his erection.
There were a few deep breaths in the room as they watched Elana sit upright on the outdoor lounge chair and began sucking the man's dick. This was what the men in the room had been waiting to see yet again, but of course, no one could say that out loud. Not during working hours.
"Is this really necessary?" Agent Patel asked, cringing at what he saw on the big screen.
Detective Mason was unphased. "You want a promotion, don't you? Trust me, Elana knows what she's doing."
The room was dead silent as they watched Detective Martinez sucking and stroking a hard dick on the live feed. Elana appeared comfortable doing this for her job. The man came in her mouth while she rapidly jerked the shaft with her lips sealed around the head. She took a sip of the margarita afterwards, letting the flavors mix.
Elana remained naked when the staff member guided her inside the resort to access the computer mainframe. All eyes in the operations room were fixated on her shapely body and bare butt. When the detective was off-screen, men in the room released quiet exhales after the sexual depravity they had just seen.
The End
