Undercover Short Story Chapter 1

Hey all, here is the final edited chapter of the yet untitled Undercover short story. A few of the Insiders had some good title suggestions for this one that I've noted down, but if any of you have good ideas for a name, let me know!

Anyways, this is a fun story that I enjoyed writing. Originally I was setting up to have the undercover short story to be about corporate espionage with another firm trying to steal information from The Lincoln Group (hint: the character who got Dan to try and plant the USB would be a central character, his wife would be the one undercover).

Anyways, this story follows an Undercover police officer named Riley Cross, who despite her husband's protests, goes undercover inside a notorious criminal enterprise to try to bring her sisters killer to justice.

It's a bit longer than I planned and there is a lot of stuff setting up future chapters (if people want it).

Anyways, here it is:

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The incessant alarm blared, and Riley reluctantly opened her eyes. She groaned as she turned over in bed and silenced the alarm on her phone.

“Is it morning already?” The deep voice of her husband, Luke, groaned from the other side of the bed.

“I know.” Riley rubbed her eyes and sat up, swinging her legs to the floor. “I think we both passed right out after. I don’t remember cleaning myself up in the bathroom or anything.”

Riley stood up and pulled her cozy robe around herself. “I’m going to make coffee before I head out. Do you want some?”

“Sure, but come back to bed first. I want to finish what we started last night,” Luke said with a sleepy grin. Riley smiled and sauntered over to him, bending down and kissing him languidly.

“But I did finish. A couple of times, in fact,” Riley whispered.

Her husband just groaned and pulled her tight body down on top of him, “How about we get you to finish a few more times.”

“Mmhmmm,” Riley purred. “As tempting as that is,” she pushed off her husband and looked down at him, “I need to hit the gym before my shift. Besides, you have morning breath and need to brush your teeth.”

“You love it,” Luke grunted as he rolled over, facing her. His eyes blinked open, and he looked up at her. “I just like having you all to myself,” Luke said. “I hate going to work and pretending like we’re not together.”

“It won’t always be like this,” Riley said. It was your idea that we keep things secret, remember? Anyway, the department has a strict no-fraternizing policy. I don’t want to get kicked out and have to go to another precinct, and I doubt you want to be relegated to cold cases.”

“No, thank you,” Luke chuckled, “I like where I’m at. It still sucks.”

“I know,” Riley said, “But it isn’t forever. It’s just for right now. I need a few more undercover ops, and there’s a chance I’ll get promoted to one of the task forces. Then things will be different.”

“But for now,” Riley said, bending over and grabbing her husband’s face with one hand before kissing him again, “Yes or no to that coffee?”

“Ugh. Put the pot on. I’m going to sleep for a little bit longer. We’re not all machines like you are,” Luke groaned.

“I don’t know,” Riley sauntered to the bedroom door and then turned to face him. “You were like a machine last night.”

Luke chuckled as Riley slipped out the door, shutting it behind her. She went downstairs to the kitchen and started the coffee machine. While it was brewing, she changed into the gym clothes she’d left out on the kitchen table the night before. By the time she brushed her teeth, the coffee was ready to pour into her travel mug.

On her way out the door, Riley checked herself over in the hallway mirror. Not bad for just getting out of bed.

She didn’t wear a lot of makeup. As a cop, it could draw the wrong kind of attention. Not that it mattered much since Riley was a natural beauty that drew a lot of attention anyway. Her piercing blue eyes and shoulder-length blonde hair were always popular with both cops and criminals. She turned, looking over her body. That ass and my breasts sure don’t help either.

Riley had heard more than one of the other officers describe her as ‘stacked’ or ‘fucking bangin’. It was disgusting, but boys will be boys. She had learned to ignore them and develop a tough exterior. This job was hard enough for a woman. She wasn’t sure how Luke put up with those demeaning comments. Since they’d kept their relationship a secret, he’d endured more than his fair share of conversation and crude commentary directed her way.

As Riley headed to the door, her eyes caught on the framed picture of her sister, Nancy, on the hallway table. Her older sister had been about Riley’s age when she’d been killed. Twenty-nine was too young for someone as kind-hearted as her sister to be ripped away from their family. The detectives at the time hadn’t put anyone away for it, but Riley knew who’d done it. She’d fallen for the wrong guy. A dangerous guy. He was one of the more sophisticated gang leaders who was able to present himself as a legitimate businessman.

One day, Riley would take down Elias Monroe and bring his entire criminal empire down with him.

***

“Detective Walker,” Captain Hunt called from across the bullpen. Luke looked up and saw the captain’s eyes meet his. The room was busy. Beat cops hauling suspects in handcuffs toward the holding cells. Victims spoke in hushed whispers with some of the other detectives. The room was alive with energy, the pulse of the city. Right, where Luke Walker liked to be.

Without saying a word, Luke got up from his desk and approached his Captain. They started walking in the direction of the interview rooms. Luke slowed his stride to keep pace with the older captain. A plain-faced black man just starting his fifties.

“What’s up, Captain?” Luke said in a low voice. Even though they were in the station, there were still ears everywhere. Some of these people reporting crimes would happily trade information to the wrong people.

Captain Hunt waited until they were in the hallway with less prying ears, “Uniforms just picked up your friend, The Toad. We have him in interview room three.” Hunt cut off as Riley walked down the hallway from the opposite direction.

“Officer Cross.” Captain Hunt nodded to her. Luke’s heart leaped at seeing his wife here, noting she wasn’t wearing her wedding band. She never did at work. As far as everyone else at the station was concerned, she was single.

“Captain,” Riley said with a flat smile. Then she nodded at him without any hint of affection or familiarity, “Detective.”

“Morning,” Luke said. He watched the captain’s eyes on his wife’s ass as she walked away from them. He shook his head, snapped himself out of his trance, and gave Luke a knowing smile.

“So Tommy The Toad?” Luke said, trying to steer the conversation away from having to make an awkward comment about his wife’s backside.

“Right. Yeah.” Captain Hunt led them over to the door of an interview room. “When the uniforms picked him up, they found a few grams on him. The DA is going to want to charge him.”

“Yeah? So what’s he offering?” Luke asked, nodding to the room they were outside of.

“Nothing. Not yet. He’s your CI, so he isn’t talking to anyone else. Sullivan’s already in there working on him.” The Captain said. Sullivan, he was one of their piss-poor detectives that somehow managed to fail upwards. He had one of the worst closure rates in the precinct, maybe even the whole city. Luke didn’t like the guy and absolutely hated working with him. Not only was he incompetent, but he was also the worst kind of cop. The kind who made assumptions of guilt on the scene and would happily fudge evidence in its favor. He’d never been outright caught or reprimanded for it, but Luke still didn’t like or trust the guy; he wanted nothing to do with him. His leers and comments about Riley didn’t do anything to help Luke’s opinion of the man.

“I know, I know,” The captain said, seeing the look of disgust on Luke’s face. “Just get in there and see what you can get out of him, okay?”

“Sure thing,” Luke said. He opened the door to the interview room and stepped inside. The large metal table bolted to the floor had two people sitting at it. Both looked up when he entered. Tommy ‘The Toad’ Rybitt sat there cuffed to the table with a bead of sweat running down his forehead. His greasy hair was slicked back to cover the growing bald patch. He smiled when he saw Luke, his jowls visibly quivering. The man was portly and a slimeball, but he was a well-connected slimeball. His information has helped Luke close several cases this year. A couple of grams of coke was nothing compared to the amount of shitbags Luke had put away because of intel from Toad.

“What are you doing?” Detective Sullivan grunted from across the table, “He’s my suspect. We have him dead to rights.”

“Captain sent me in,” Luke said calmly as he walked over to the table. “He wants me to take over.”

“That’s bullshit,” Sullivan said, getting to his feet to look Luke in the eye. Well, up into Luke’s eyes. While Luke was tall and built like a running back, Sullivan was built like a failed linebacker. All pudge and no muscle. When people joked about cops’ addiction to donuts, they were talking about Sullivan. “You can’t just swoop in and take another one off my hands. This one is mine.”

“Take it up with the Captain,” Luke shrugged, “The DA is probably here if you want to talk with her too.”

“I will,” Sullivan pushed past Luke as he stomped to the door. Sullivan left, slamming the door behind him. Luke sighed and sat down in the chair.

“Tommy. What did I say about being more careful? You shouldn’t be here. It’s not a good look for you.” Luke said, opening the folder Sullivan had left on the desk.

Toad just smiled and raised his hands innocently, the handcuffs rattling against the table. “I was just heading to a party. I’m not selling the stuff.”

“Well, possession of a Schedule 2 controlled substance is still illegal. Given that you were on your way to a party, I’m sure the DA can make the case that you also intended to distribute. It doesn’t look great for you.” Luke said, looking down at the case file and feigning indifference.

“Look. Luke,” Toad started. Luke’s eyes snapped up, giving the dirtbag a hard look. “Officer Walker,” The ‘Toad’ corrected himself, “We both know I have a lot to offer, so can we skip this song and dance, please?”

“That depends,” Luke said. “What do you have to offer?”

“Well,” Toad leaned back with a smirk on his face, “We just had a waitress quit at Sidecar. Rico put me in charge of finding a replacement. I know you’ve been wanting to get eyes and ears in there. Is that enough to make these charges disappear?”

Holy shit. Sidecar was one of the Chicago underworld’s seediest clubs, where a lot of backroom deals were said to happen. It was a place no cop had ever set foot in. The guest list was the exclusive domain of dirtbags and shitheads with rap sheets a mile long. If they could get someone in there, the things they could overhear. But it would be dangerous. Elias Monroe owned the place. Mr. Untouchable himself.

“So,” Toad said, “We got a deal?”

***

Riley filed into the small meeting room alongside the other officers specializing in undercover work. She ignored the leering eyes of some of the men in the room and sat near the back. No one was sure why the meeting had been called. It hadn’t been scheduled, which usually meant there was some new development or opportunity the department needed to jump on immediately.

After everyone had settled into the room, Captain Hunt, the woman from the D.A.’s office, and Luke walked in and stood at the front of the room.

“Thanks for dropping everything and getting here on short notice,” the Captain said as Luke closed the door. “First of all, you may notice that there are only a handful of us in the room. We need to keep the circle around this tight. So nothing leaves this room- cone of silence, understood?”

Everyone, including Riley, nodded.

“Good,” the Captain said. We just had a big opportunity drop into our laps, thanks to Detective Walker here. For the first time ever, we might be able to put someone inside The Sidecar.”

The words hung in the room, and every officer understood what they meant. Someone inside one of the most notorious clubs in the city. One of Elias Monroe’s clubs. The man suspected in her sister’s death. Riley cast a glance at her husband, who shook his head at her. He didn’t want her put on this. He would tell her she was too close to this, that her decision-making was compromised. But there was no way she was going to sit this one out.

“The club is looking for a new waitress. And thanks to Detective Walker’s CI, we have an inside track to get one of our people in that position. To be clear, this could be one of the most dangerous undercover assignments we’ve seen in the city. You’ll be walking into the lion’s den without backup or any way to communicate with us. Whoever goes in will have to go in deep. That means putting you up in an apartment to sell your covert identity, working there most nights, and restricting contact with family and friends. You will have to live as this person would. Obviously, there will be periodic check-ins to see how you are doing and if there is actionable intel.”

Riley felt herself perk up in her seat, ready to volunteer. Luke looked around the room before his gaze settled on her, and he subtly shook his head. As much as she loved and respected him, this wasn’t his call. This was her career and her decision to make.

“But to be clear. This isn’t just about going after Elias Monroe. Yes, we think he has shady dealings, but he is also a friend of the mayor. We cannot touch him unless we have an air-tight case against him. Helping to build that case might be part of this, but there is a treasure trove of criminals in there, all of which we need intel on to help us put away. Is that understood?” The Captain asked.

Everyone nodded again.

“Good. Now, understand that this may be a months-long assignment. Potentially longer. We don’t know yet. I am looking for a female volunteer who is willing to do this. One willing to put their attachments on the back burner for an indeterminable amount of time. Everyone else will play a support function behind our lead person inside,” Captain Hunt said.

Riley didn’t want to seem too eager, but after a few seconds, she raised her hand, “I want to do it, Captain.”

“Good,” The Captain nodded, “Okay then, I think we can move on to –”

“Sir,” Luke cut in, stepping forward. No disrespect to Officer Cross, but for an op as important as this, don’t you think we need someone more experienced? Someone who has done a long-term undercover assignment before?”

He was trying to cut her out of this. That loving, stupid man was trying to protect her. But she was a cop just like him and didn’t need his unsolicited protection. As much as she loved him, she wasn’t going to let him dictate her career like this.

“Captain, Detective,” Riley said, standing up, “With all due respect, Detective, I’m perfect for this op. I’m comfortable handling myself undercover with lowlifes like this. Just like I did with the Street Kings last year, which led to one of the largest drug seizures the city has ever seen, I can improvise and think on my feet. I won’t freeze up like we’ve seen other times. I have no attachments. No boyfriend or anything and no family in the city. I can go undercover for months without an issue. And there is another factor that hasn’t been brought up yet.”

“Enlighten us, officer,” Captain Hunt said.

“These guys only hire pretty, young women. I’m not saying I’m the most beautiful woman in the world, but I’m not an idiot, either. I have the experience, and I have the look for his assignment. And besides, no one else volunteered,” Riley said.

Captain Hunt nodded and looked at Luke, “I’m sorry, Detective, but we’re going with Officer Cross on this one.”

Luke was not happy that Riley had volunteered for the assignment. Or the fact that she had so strongly advocated for herself. They'd fought the last night she had spent at their home before she had to go undercover. Luke was well-intentioned in wanting to protect her, but she wasn’t a damsel in distress who needed protection. She had risen through the department's ranks, shaped by the mean Chicago streets just like he’d been. He couldn’t see that his actions undermined her autonomy and career aspirations.

Besides, she was a big girl who could handle herself. Sure, she’d be walking into a lion’s den full of predatory men, but she wasn’t a rookie anymore. Undercover work required one to be more flexible with their moral compass, but it wasn’t like she would let these guys anywhere near her, especially since she was married. Despite her tough exterior, she was still a faithful wife at her core.

As the loud bass of the music drummed in her ears and she filled a tray full of drinks, she couldn’t help but miss her husband. For as stubborn as he was, she still wished that he was close by. Luke wasn’t allowed to contact her, and no one at the precinct was. She met with her secret liaison in the undercover unit every few days, giving him updates and any potentially actionable intel she’d gotten.

She’d only been working in the club for about three weeks, but the information she had already gathered tipped the police off to a few things that weren’t even on their radar, leading to multiple arrests.

The club was always packed with lowlifes and their entourages. Even tonight, almost every table and booth was filled with men. The occasional woman sat amongst them, likely someone’s girlfriend or, more likely, their girl of the week. The music pulsed, but most people stayed seated, drinking, talking, yelling, and occasionally fighting. Those fights broke up quickly, and the combatants were never seen again.

Riley quickly realized that most of the men here were the low-level muscle of their respective organizations. Some were sons of someone important with their own entourage of sycophants. The real business happened upstairs or back in one of the private VIP rooms. Riley hadn’t been allowed into either place yet.

She dropped the drinks off to a group of men who got quiet when she approached. Their eyes appreciatively drank in the curves of her body. Riley steeled her nerves and plastered on a blank, bimbo-like smile as she reached across the table to set the drinks in front of their respective patrons. Some of the guys elbowed each other and glanced down the valley of her exposed cleavage. The one thing Luke’s CI had failed to mention was the dress code for the waitresses.

Each night, Riley had to pull on a pair of short, black booty shorts and a tight, black t-shirt with a plunging V neckline that showed off the bulging tops of her breasts. It was humiliating to put her body on display for these dirtbags. Letting them leer and drool over her with their crass comments. Occasionally, one would get too handsy, and she had to summon every bit of willpower she could not to put them in an armbar and slam them into the table.

It was frustrating, spending night after night being ogled by these hooligans when she could be at home with Luke. But this was the assignment. Still, she wasn’t happy. Yes, she’d helped get a bunch of people arrested or put under surveillance already. But most of them were low-level criminals who were expendable. She was here to take down Elias Monroe but hadn’t gained anything insightful so far. She itched to do something more, to be productive.

Her handler wanted her to keep doing what she was doing, but that wasn’t enough for Riley. She needed to take down Nancy’s killer.

Riley smiled at the group of immature men before sauntering back to the bar. She could feel their gazes on her ass with each step. As she began filling her tray with more drinks, Luke’s CI, Tommy ‘The Toad’, slid up next to her at the bar.

One thing was for sure: He did look like a toad, with his fat, protruding stomach, large eyes, slicked-back greasy hair, and multiple chins. The only thing about him that was unlike a toad was the dirty mustache he kept over his upper lip.

“I’m giving your tables to Sherry,” Toad said. He oversaw the bar area and the general running of the club. “I need you to take care of some VIPs.”

“Who?” Riley asked. She didn’t like that Tommy ‘The Toad’ was her closest thing to a real contact here. He was the only one who knew she was a cop and, at any second, could reveal that information to anyone. It would be his word against hers, and if she was dead, he could feign ignorance. She didn’t trust him and hated putting her fate in his hands. But if something happened to her, Luke would annihilate him. Not that Tommy knew that. No one knew about her marriage to Luke, and she sure as hell wouldn’t let some greasy CI be the first to know.

Toad nodded towards the back of the club. Riley’s eyes followed his, and she felt her blood run cold. There at the back of the club was Elias Monroe, glad-handing with other men as he passed through the crowd. Elias was in his fifties, in a sharp suit and well-groomed. He was black, 6’1 ", bald, and had a notable chin scar. He looked more like a politician or a businessman than a criminal mastermind.

He was headed towards a private door at the back of the club where a large bouncer was standing. Riley knew that behind the door was the staircase up to the second floor where big deals were ironed out.

“You want me to go up there?” Riley asked, holding back her excitement. The prospect of overhearing something and finally taking that bastard down made her beam. This could be it. Her chance to find out what happened to Nancy once and for all. To bring Elias down, earn her a promotion, and allow her to return to her normal life with Luke all at once.

“No. No way,” Toad said quietly. “We don’t bug the boss.” Toad gestured to a few men who peeled off from Elias’s entourage and went to their own table. They were a handful of his lieutenants. The most notable was Rico Garcia, who ran several different businesses like The Sidecar and Kurt “The Hammer” Donovan, who had a long list of prior offenses. The detectives suspected that ‘The Hammer’ was one of the people who handled the more violent aspects of Elias’s criminal empire.

Toad made a gesture, and the bartender mixed several drinks and put them on a tray. “Bring this over to them. They’re your main focus for the rest of the night. Got it?”

She knew he was talking to her like he would the other waitresses, but Riley despised being talked to like this, especially from a piece of shit like him. She smiled at him, knowing the bartender was watching, “You got it, boss.”

Riley took the tray and headed towards the private booth where Elias’ lieutenants were seated. She weaved her way through the throngs of people while subtly keeping an eye on the door Elias had gone through. Maybe there was some way she could get up there and plant a bug? She shook her head and focused her eyes on the table where the lieutenants sat. No. That was a good way to get herself caught and killed. Maybe Luke was right. Maybe she was too eager to take Elias down. She needed to take a beat and be smart about this, not rush headfirst and go after the big boss right away. Riley narrowed her eyes as she approached the table, taking in the lounging men.

This may be the path forward. The lieutenants. They might say something she could use, or maybe there was some way to entrench herself with them. Riley suppressed a shudder of disgust, knowing what that might mean.

“Hey there, boys,” Riley said, pure sex dripping from her voice. She lowered the tray to the table, and the men reached out to grab their drinks.

“Are you Toad’s new waitress?” Rico asked. He was just a few years older than she was, but his face looked middle-aged. Maybe it was alcohol or a hard life. She wasn’t sure. But there was something else to him. His eyes trailed up her body, sizing her up as a smile spread across his face. He had dark olive skin and seemed to be of Latin descent. The sides of his head were shaved in a high fad,e while the hair on top of his head went from the back of his neck all the way to just over his eyebrows. It looked like a piece of roadkill had landed on top of his head. He looked at her with an intense gaze. There was something behind his dark eyes that intrigued Riley. He was an ugly man but had an unnerving, rakish charm.

“Mr. Tommy?” Riley asked. “Yes, I just started a few weeks ago.”

“What’s your name?” Rico said loudly over the music.

“Riley,” she answered. Normally, for an undercover op, she would be sliding into the role of a buyer or some other contact their suspect was expecting but hadn’t met before. For this assignment, she and her team decided to keep things simple and use her real first name. Not her real surname, just the same first name so that there was one less thing she needed to worry about remembering. This assignment was complicated enough with all of its moving pieces.

“And how’s it been so far? Everyone treating you well?” Rico asked expectantly.

“Everyone’s great. And the tips are really, really generous here,” Riley said. That part wasn’t a lie. The alcohol plus her skimpy waitress attire made for a lot of heavy tippers.

“I’d like to give you more than just the tip,” The Hammer said, his large hand running up the naked flesh of her thigh before grabbing one of her ass cheeks. The large bearded man chuckled at what he’d done. He was bald with a salt-and-pepper beard. He was a giant of a man; even sitting, he was at her eye level. The sudden imposition caused anger to flash across her face for a brief moment before she could compose herself. Unfortunately, she was sure that Rico had noticed.

Riley faked a giggle and twisted herself out of The Hammer’s grip. “I’ll bring another round of drinks over in a bit.” Riley turned and walked back towards the bar. She held back the revulsion from appearing on her face. Letting a convicted felon feel her up like that made her skin crawl. But she would endure it if it meant getting intel that could take his boss down.

As she walked back to one of the bars, she saw Toad with a bemused smile on his face. She shot him a death glare, but it didn’t wipe the smirk off his face. He must’ve seen what had happened.

“Enjoying yourself?” Toad said in a low voice without looking at her.

“They’re a bunch of pigs,” Riley said, low but loud enough for him to hear.

“Well, this is what you wanted,” Toad shrugged, turning back to the bar, “Heads up, you have incoming.”

Riley didn’t immediately look up. Instead, she turned towards the bar and grabbed some washcloths to clear the tables. Her eyes flicked up to the mirror behind the bar, and she saw Rico striding towards her, his eyes planted on her supple ass. She wanted to roll her eyes but controlled herself. The Latin man composed himself and stepped up next to her at the bar. Riley cast him a glance, and he gave her a warm smile.

He leaned in, “Sorry about that. About what Hammer did back there. He’s… not always a gentleman.”

“It’s fine,” Riley said as Toad took a sip of his drink and walked off, leaving her alone with this man. She felt uneasy that her only support had just left, but this was the job. Besides, having Toad for support was basically useless. Riley turned back to what she was doing, feigning indifference. This was a big opportunity to get in good with a key lieutenant in Monroe’s operation. She needed to play it exactly right.

“It’s not, though,” Rico said, leaning in again. “That shouldn’t happen. Not in here. Not while you’re working. When you come back to the table, Hammer will apologize.”

“That’s not necessary,” Riley said. While she wanted to get closer to this group, she also didn’t want to attract too much attention to herself so quickly. “Thank you, though. I appreciate it.”

Rico blatantly looked her up and down. Then he smiled at her. There was something warm and inviting about his smile. It was incongruent with the rest of his features.

“Say,” Rico said, smiling. The smile now had a different intent behind it, and Riley knew all too well what was likely going on behind those dark eyes. “Why don’t you put those wash clothes down and dance with me?”

Riley turned towards him, and his eyes quickly fluttered down to her cleavage before looking back up at her face.”I’m sorry, I can’t. I’m working, and we’re really busy,” Riley said, gesturing to the crowds of people in the club. “Besides, my boss says I can’t fraternize with our patrons.”

Rico’s smile grew even wider. Riley knew Toad worked for Rico, and she just gave the man an in to make him feel like he was the one in control. The one making the decisions.

“Do you know who I am? Any idea?” Rico asked.

“Hopefully, a good tipper?” Riley asked. Light flirting would seem natural for a waitress while also stroking this guy’s ego.

“I’m Rico,” he held out his hand. Riley politely shook it with a loose grip. When she tried to reclaim her hand, Rico held onto her gently, his thumb caressing the back of her hand, “Rico Garcia. This is my club.”

“Really?” Riley feigned surprise, “I thought it was Mr. Tommy’s?”

Rico chuckled and gestured to Toad, who had been watching from across the room. The short, chunky man waddled over, and Rico put his arm around his shoulders. “Is this your club, Toady?”

“No sir,” Toad shook his head, “This is your place, Rico.”

“So I’m the boss then, right?” Rico said.

“Yes, sir,” Toad said, looking up at the younger man.

“So if I wanted to say, give one of our waitresses a break, I can do that, right?” Rico asked.

“You can do whatever you want. You’re the boss.” The Toad answered.

“Whatever I want. Hear that?” He smiled at Riley before patting the Toad on the back and dismissing him. “So, about that dance?”

Riley felt her skin crawl. She glanced at the dance floor. This wasn’t a club where people line-danced or even slow-danced. It was a full-on grind fest. Ass to crotch, grinding on each other. Dirty dancing. That wasn’t something she thought she’d signed up for. But she knew undercover work involved all kinds of activities that sometimes strayed too close to the lines of one’s morals.

“I would,” Riley said in an appeasing tone, “But I still don’t think it's right. All the other girls here are going to see me dancing with the boss. They’ll hate me.”

“Fuck ‘em,” Rico said, “Who gives a shit what they think?”

“I do,” Riley said. “You’ve never been a woman. The glances, the shit-talking behind your back. I don’t want that.”

Rico pursed his lips for a few seconds before his infectious smile returned. “I got an idea.”

He pushed close to her and put his arm around her shoulders, turning her around to face the back of the club. He pointed towards the door in the back wall, the one she’d seen Elias disappear through.

“See that door?” Rico asked. Riley nodded. “Toad’s office is back there. Let’s go back there and dance where no one can watch us.”

It was a stupid idea. All her coworkers would see her going back there with the boss. It wouldn’t help with the issues she brought up just a second ago. But she needed to get behind that door and might not ever get another chance. She knew what Rico was angling for, but she’d figure a way out of that once she got back there. Still, the idea of being alone with a criminal like this anywhere besides an interrogation room unnerved her.

“Okay,” Riley said, returning Rico’s smile. The grin on his face widened, and he reached over the bar and grabbed a half-full bottle of Tequila. She’d figure something out. She wasn’t about to debase herself with this degenerate. Unlike some other couples, her marriage vows to Luke meant something more to her than just words she’d spoken on a special day.

“Let’s go then,” He said, his hand pressed into the small of her back. He guided them through the club to the reinforced steel door at the back. The bouncers nodded to him and opened the door. Riley doubted this was the first time they’d seen Rico do this with a girl.

The hallway behind the main room was dimly lit. There was a concrete stairway leading up to the second floor. This is where Elias had gone earlier. Rico guided her away from the stairway and down the dark hallway. Several rooms were lining the hallway, the loud sounds of the main part of the club somewhat muted. Her team suspected the whole place was a front for other activities, but nothing back here seemed illegal. If there had been so much of a hint of a money laundering operation or a drug lab, she could have had the whole place shut down and Elias in handcuffs within hours.

Sadly, there wasn’t anything evidently criminal in the hallway. She couldn’t see behind the closed doors - they each had a window, but they were too dark to see through. Rico led her around a corner. The hallway ended at a small office that he guided her into. A large desk that took up most of the room was piled with papers and bound documents. A couch and table sat opposite the desk.

Riley stepped into the room, her eyes gazing over its contents. She stepped towards the desk, scanning it quickly, trying to catalog anything important. A shipping manifest was sitting out in the open, and she memorized the ship's name and part of the bill of lading number. Then, she turned and looked at Rico. “Nice office.”

“It’s a dump,” Rico said, moving behind the desk. “You should see my place in midtown sometime. It's much nicer.”

He pulled open a drawer, brought out two dusty glasses, and poured a generous amount of tequila into each. He handed one to Riley and raised his glass. She returned the gesture and put the glass to her lips, drinking back the tequila. Rico smiled at her and topped up both of their glasses.

“There’s not much room here to dance,” Riley said, looking around. Rico just smirked. The bass of the music could still be heard through the walls. Beating as if the club had a heartbeat.

“I’m sure we can make something work,” Rico said, putting the tequila bottle on the table. He took her hand and led her over to the couch. Rico sat down and insistently pulled Riley down onto his lap, facing away from him. His hands went to her hips, gripping them firmly, and he started moving her side to side in time with the beat. Riley glanced at the door, which was partly ajar, knowing she was entirely on her own with this hardened criminal.

Riley finished her drink and set the glass down on the table. She followed Rico’s lead and swayed her hips back and forth in his lap. It didn’t take long before his calloused hands ran up her back, going to massage her shoulders and then caressing her bare biceps. Riley continued to sway with the beat as the heat of the tequila settled into her stomach.

Then she felt it.

Rico’s cock pressed up against her bubble butt. He groaned deeply behind her as he pushed his growing cock against her backside. Riley steeled her nerves as she ground her perfect ass against this man. A man who wasn’t her husband. A criminal. The kind of person Riley and her husband had dedicated their lives to putting behind bars. What would Luke say if he saw her right now? She cringed at the thought. But she had vowed to do whatever it took to figure out what had happened to her sister and bring her killer to justice. Rico was just a stepping stone she needed to get to Elias.

The tequila started to calm Riley’s nerves. Over the course of the next ten minutes, Riley swayed and ground her ass on Rico’s lap, her hands perched on his thighs for support. One song ended, and another began.

“Get up for a second,” Rico grunted behind her, “I want a drink.”

Riley stood up, and Rico reached past her to the tequila bottle on the table. He grabbed it and took a healthy swig before passing it to her. She did the same. That same mischievous grin spread across his homely face as he boldly reached up and hooked his fingers into the waistband of her black booty shorts. Riley swayed, unsure if it was due to her unconsciously still moving to the beat of the music or if the strength of the liquor was moving the room around her.

“Let’s get more comfortable,” Rico said and slowly peeled down her body shorts, revealing her black thong. His eyes lit up like a kid on Christmas. The sheer material fell to her ankle,s and goosebumps were visible on the skin of her bare thighs. Riley paused, wondering how she was going to get out of this. Her phone was in her locker, so she couldn’t call for backup. She was alone. The Toad wouldn’t come to her aid – not when Rico was his boss. She’d have to come up with –

Rico quickly undid his belt and slid his pants and boxers off in one swift motion. A menacingly large cock jutted out, staring right at her. Bigger than Luke’s. The thought popped into her mind before she had a chance to process the scene. She chastised herself for the errant thought, no matter how true it was.

“Do you always bring your employees back here like this? Show them what you’re showing me?” Riley asked, taking another sip from the bottle.

“I’ve never had an employee as sexy as you before,” Rico grunted, seemingly reaching for the tequila bottle. But instead of grabbing it, he grabbed her wrist and clumsily pulled her back down on top of him, straddling his lap.

Riley let out a soft, unintentional moan as she felt his engorged cock pressing up against her thong-clad pussy. The only thing between her and this criminal’s cock was the thin, sheer material. The heat of it against her sex made this unimpeachably clear.

“That wasn’t an answer,” Riley challenged.

“No, it wasn’t,” Rico muttered, taking the bottle from her hand and gulping more of the potent liquor down his gullet. He handed it back to her, his eyes trailing over her partially exposed body. His hands ran up her smooth thighs before each grabbed a handful of her flawless ass cheeks. He pulled her tighter against him, his cock pressing hard into her pussy, pushing her lips apart. His hands moved deliberately, rolling her ass cheeks, making her hips follow his motion. Riley resigned herself to this, acquiescing and grinding into his cock with her body.

She tried to compartmentalize what was happening and detach herself from the situation. This could actually work in her favor. If Rico wasn’t drunk yet, he was well on his way there. And his mind was clearly occupied with other thoughts.

She’d make this into an interrogation.

“So you’re the big boss, huh?” Riley said in a low, sultry voice.

“I am. Wouldn’t you agree?” Rico said, staring at her cleavage. He thrust his hips up, pushing his hard cock against her. “Nice and big,” he raised his eyebrows playfully.

Riley shuddered. For the first time, she was beginning to feel like she was losing control. Her body was actually responding to this fucking asshole. It wasn’t just the alcohol that was making her chest warm. She could feel herself getting turned on. Maybe it was the situation. Or maybe it was because she had been apart from her husband for several weeks, and she was extra sensitive and needed contact. Or maybe it was just the basic biological fact of having a large, hard cock pressing against her clearly responding vagina. Whatever it was, Riley needed to get her head on straight and fast.

“Mhmmm, that’s hot,” Riley moaned, unsure how much of that wanton moan was an act. “Having the boss all to myself. Are you really in charge, or do you have a boss, too?”

Rico looked up at her, his face going from chill to discerning, “Why does that matter?”

Riley leaned in, bit his earlobe, and whispered, “Because it makes me wet.” She ground against him as she spoke.

“Fuck,” Rico muttered ,laying his head back on the couch, “Everyone’s got a boss. But you don’t need to worry about that.”

He tugged at her black shirt and pulled it up over her head. The part of Riley that was detached from the situation realized that she was in her black bra and panties, grinding herself on the lap of a known criminal.

“You and your friends looked so dangerous,” Riley said in a low voice, “So sexy. Are you really a bad boy or just someone who likes to play pretend?”

She continued to grind herself against Rico’s cock. She could already feel the precum oozing out of it and staining her black panties. She needed to be careful. Riley was walking a dangerous line with a dangerous individual. Back here, with no witnesses, he could kill her or something worse, and no one would ever know. She wasn’t sure he was that much of a hardened criminal, but she still needed her questions to seem innocent. She couldn’t sound like a cop. Or ask questions like a cop. She needed to lean into being playfully curious and seductive. Even more dangerous was how horny she was feeling at the moment. Weeks of pent-up desire, and there was a hard cock right here, constantly pressing into her. But she wouldn’t cheat on her husband, even if it might get her closer to her goal.

Rico grinned, and a dark expression passed behind his eyes. He grabbed her hand and pulled it between them, placing it on his cock. He closed his fist, making her fingers grasp his hard shaft. Riley opened her mouth in surprise, and Rico’s lips were on hers. Kissing her hungrily.

In all her time undercover, this had never happened. Riley didn’t know how to react. Her brain told her to rely on her training. Go back to her fundamentals and extract herself from the situation. But her body melted into his. Her lips kissed him back. Her fingers raised and fell on his cock, stroking it. Through the fog in her brain, she realized something. Something dangerous. That she shouldn’t be doing this. A cop with a criminal? It was wrong. It was taboo. It was….getting her off?

Riley tried to pull back, but Rico’s strong hand held her head in place as his tongue pushed into his mouth. He tasted like tequila as his tongue ran over hers. She could picture how angry Luke would be walking into this situation.

“Mhmmm,” Riley moaned again unintentionally. The sound mortified her. She shouldn’t be enjoying this. That moan wasn’t part of the act. Her body was betraying her. She needed to find a way to take back control of the situation.

Just then, Rico’s phone rang. He broke the kiss and grabbed his phone, looking at it.

“Shit, I got to take this,” Rico muttered, looking worried.

“Okay, I should probably be getting back,” Riley said, sliding off his lap and picking up her booty shorts off the ground.

“No, just one second,” He grabbed her wrist and brought her hand to his cock again. Riley knew she could still bolt out of there. She was about to, but then Rico answered the phone.

“Hey Bossman, what’s up?” Rico said. Riley froze with her hand wrapped around Rico’s thick cock. He was talking to Elias right now, right in front of her. The man she’d vowed to take down. No warrant or wiretap needed. At that moment, Riley knew she couldn’t leave. But she also knew she could just stand there bent over with her hand around Rico’s cock, actively listening to the conversation. That would be too suspicious.

Riley dropped to her knees between Rico’s legs. Hoping that Luke would understand, she began to pump Rico’s thick cock with her fist. The man laid his head back on the couch and stifled a groan.

“Yeah, the Colombians are arriving at 4 a.m. Our guys will be there to meet them,” Rico said.

Oh my god. Elias’s group is working with the Colombians? No one in the department knew that. She couldn’t leave now. She needed to hear the rest of the conversation. She realized she was making it too obvious that she was listening; her hand barely moved.

Riley gripped the criminal’s cock with renewed determination. It was fucked up, but she needed to keep her cover. She thought of her sister and focused on the task at hand. She licked her other palm and brought both hands up to begin working on Rico’s cock. She could feel his heartbeat pulsing in her hands.

“Yeah, Hammer picked them up today,” Rico said, looking down at her. She looked back up at him seductively. Then his other hand reached out and rested on the top of her head, gently pulling it down.

Riley’s eyes widened as the olive-skinned cock grew closer and closer to her face. She wanted to run. To preserve her marriage vows and not touch any part of this fucking criminal. But she needed to hear this intel. Needed to know what they were planning so she could take them down once and for all.

Riley braced herself and pushed everything else out of her mind. She opened her mouth, and Rico’s thick cockhead passed between her lips and disappeared inside. What would Luke think? The other guys in the department? If they knew, she would never live this down. Their already leering eyes would likely intensify when they saw her. Jesus, what would Captain Hunt say?

“It’s, it’s ah, coming up through Panama. It’ll be here in a couple of days,” Rico said. Panama, like the Panama Canal. Maybe this had something to do with that shipping manifest Riley had seen on the desk.

Rico kept his hand on the back of Riley’s head and firmly guided her mouth down onto his cock. More and more of the thick column of flesh went into her mouth until it pressed against the back of her throat. She braced herself on his thighs, and his hand eased up but stayed where it was. He guided her head up and back down.

“Mhmmmm,” Riley moaned around his cock. Goddammit. Don’t enjoy this.

Riley’s thighs clamped together. She could feel that the front of her thong was wet. She told herself it was just from Rico’s precum earlier, but she knew the truth. She was wet from this fucked up situation.

Riley pulled her mouth off Rico’s cock and licked the entirety of his length. She licked him all the way down to his balls, thankful that the man shaved his cock just like her husband. She hated pubic hair. It always got in the way. Rico’s hand pressed against the back of her head, forcing her mouth onto his large balls. Riley lapped at them, her tongue dancing across the little bumps dappling his heavy ballsack, tracing each of his balls with the tip of her tongue.

Both of her hands continued to stroke Rico’s throbbing member. It felt so hard and inflexible in her hands.

“Once we have them, we’ll run this city. No one will be able to stop us,” Rico said. Then he added, “Yeah, I got something to finish up here. I’ll be up in a few minutes.”

He tossed the phone aside and said, “Fuck baby, that feels fucking good.”

“I want to teach you how to suck a cock properly and fuck you all night, but the boss needs me,” Rico said. He pulled her back up to his cock where her lips parted and took him in her mouth again. Her hands still stroked him, feeling the contours of his cock in her palms.

“Mhmmmm,” Riley moaned again.

“I only got a couple minutes,” Rico said with a groan, “Fuck. I knew when I saw you tonight that I had to have you. I can’t wait to fuck you.”

Riley didn’t know how to respond. She just focused on the task at hand. The faster she finished him off, the faster he’d leave. Her shift was almost up. She needed to get out of here and report what she’d heard to her handler.

“Rico,” A voice said, “The boss is waiting – oh shit.”

Riley pulled herself from the cock. Her head spun to look at the door. There, The Toad was standing with a bewildered look on his face at the scene before him. Then, it broke into a wicked smile. Shit, Riley thought. He knew she was a cop, and now he saw her in this compromising position. He looked at her, and his smirk spoke volumes.

“I’ll be up in a minute,” Rico said, “Just finishing up here. Close the door, Toad.”

Toad didn’t break eye contact with her as he closed the door and left.

“Now, where were we?” Rico said, putting his hands on the back of her head, “Oh yeah, you were just about to beg for more.”

Riley swallowed. Even though it was embarrassing and compromising that Toad had seen her, she’d hoped Rico would’ve left with him. She eyed Rico’s throbbing member in front of her and the angry purple vein running up its considerable shaft. Her stomach turned in revulsion at the inevitable conclusion her mind had reached. She would have to finish this. If she walked away now, it would look suspicious and might close the door to future intel.

“Don’t worry about Toad, baby,” Rico cooed. “He’ll probably jerk off to the image of you in your bra and panties later. But he’s harmless.”

“Now,” he added, stroking her cheek, “Time to open up.”

Riley steeled her nerves and tried to suppress the dread and arousal coursing through her body. She gripped his cock in both her hands and lowered her mouth on it, tentatively swirling her tongue around the head.

“Fuck. Yeah, baby,” Rico murmured, stroking the back of her head, “You like that?”

“Mmm-hmmm,” Riley moaned in confirmation.

“Look up at me, baby. Tell me how much you like it,” Rico groaned. Riley was torn on what to do. She was holding back her arousal at the situation. At touching this…criminal. She felt betrayed by her body but still had a mission to fulfill. She didn’t know what was better. Engage him a bit and try to get this over with, preserving what was left of her dignity and marriage vows. Or lean into it more to turn him on, and hopefully, he’d bring her around again where she could gather more intel. She didn’t know what the right decision was.

Riley thought of her sister. There really wasn’t a decision to make. I’m sorry Luke….

“Mmmhnmmmm,” Riley moaned. Her eyes snapped up to meet his as she took her mouth off of him. “I don’t like it….No. I love it.”

She knew what got men like this off. Power.

“I love how big and strong your cock is. It feels so powerful in my hands,” Riley said, stroking him with one hand while the other cupped and massaged his balls. She slowly licked up the length of his unyielding cock, her tongue running over the angry purple vein.

“Bigger than your boyfriend’s?” Rico asked. Riley thought of Luke’s perfect cock. It had always been enough for her. But she couldn’t lie to herself. Rico’s was bigger. Not that things like that mattered.

“Who says I have a boyfriend?” Riley challenged.

“I can tell. The way you carry yourself. You’re not like the other girls in here,” Rico said. Shit. It wasn’t good that he saw her as different from the other girls. Yes, she wanted to get further in with them to gather intel, but she shouldn’t stand out unintentionally like that. She hadn’t realized it, but maybe she was behaving a certain way because she was married.

“We broke up a couple of months ago,” Riley lied. I’m still not over it.”

“I’ll help with that. Don’t you worry,” Rico chuckled, “Fuck baby keep that up.”

“Like this?”

“Just like that.”

Riley continued to delicately massage his balls while eagerly licking and sucking his cock. Her other hand had an iron grip on his shaft. Stroking him non-stop. She wanted to get this over with. She knew the words. They were in the back of her throat, but she hesitated to say them. Finally, she summoned the willpower and uttered, “Cum for me Rico. I want it. I want your cum. Give it to me.”

Riley pulled back and kept stroking him. Staring into his eyes. She’d make him cum all over himself before his meeting with Elias. Despite her own arousal, she couldn’t let him finish in her mouth. She couldn’t let that happen. It was crossing a line. Both professionally and in her marriage, she couldn’t –

“Oh Fuck!” Rico groaned, his hips rising off the couch, “I’m gonna cum.”

His hand on the back of her head pulled her forward, and his cock spread her lips open. Riley was about to object when the first rope of cum blasted against the back of her mouth. She held onto his shaft, feeling the cum pulse in her palm for a few seconds before rope after rope of his hot sticky jizz filled her mouth.

Rico kept groaning, holding his hand on the back of her head. His hips raised, and his cock twitching in her palm. There was so much fucking cum. Her entire mouth felt filled. It was leaking out of her mouth and dripping down his shaft, over her fingers. Over her bare ring finger.

She wanted to spit it out, but Rico was groaning in pleasure, unaware of her plight. She needed to breathe. Riley swallowed, almost choking on his hot cum as it poured down her throat. She swallowed again, taking more and more of this criminal bastard’s illicit seed into her own body. Revulsion turned her stomach while her pussy soaked her panties. What the fuck is wrong with me?

Finally, Rico slumped back against the couch while Riley gasped for breath. Her mouth was still sticky with the remnants of his load of cum. She couldn’t believe how much he had cum. Riley could still feel the heat of his load in her stomach, a cruel reminder of the price she’d paid for the intel tonight.

A thin line of cum ran from the tip of his cock to her lips. Her hand was drenched in the sticky substance, and she was amazed at how much more had leaked out.

“Ugh,” Rico groaned and stroked her cheek. “That was amazing. But next time, I’m gonna teach you how to suck a cock properly.”

Riley felt a strange sense of sadness at his comment. Disappointed that it came right after she had just blown him. As if in violating her vows, she hadn’t blown him good enough. Like her skills weren’t up to his standard for cock sucking. She was confused, sad, and upset but had to remind herself that this was just an assignment. It wasn’t personal.

Rico groaned and stood up. He pulled up his pants and headed towards the door. “Come on, let’s go. I can’t leave you back here by yourself.”

Riley quickly got dressed and followed Rico back out to the club's door. He gave her a long, wet kiss before heading up the stairs to meet Elias alone. Riley pushed through the doors and felt the eyes of the other waitresses on her. Toad stood by the bar with a calculating look on his face as if he were assessing something about her.

Riley put her head down and tried to keep the details from the shipping manifest and the conversation she had overheard fresh in her mind. There was only an hour left in her shift, and then she could signal her handler for a meeting.

***

“This is big,” her handler said from the other side of the booth. They sat in a 24-hour diner on the other side of the city, far away from Elias’s known territory. Riley had just finished explaining everything she had overheard and the details from the shipping manifest. Her handler was a cop she hadn’t worked with before—an older man named Jim who had done plenty of undercover work before her time.

Riley had taken an indirect route to the dinner and doubled back a few times to ensure she hadn’t been followed. The entire time, her mind was ablaze with the memory of Rico’s face as he busted into her mouth. The overwhelming amount of criminal cum she’d been forced to swallow.

“I need to get to the station so the team can start processing all of this. Great work, Riley. Really great work. How did you get all this?” he asked her.

Riley felt her face blush at the memory of sucking Rico’s fat cock in the dingy club office. She tried to ignore the pangs of sexual desire that still coursed through her.

“It wasn’t anything special,” Riley said. “I saw the manifest on a desk in the backroom.”

The right thing for her to do would be to tell him it was Toad’s desk. That they should press Toad for more information. But if she did that and Luke went and talked to him, he would likely reveal what she had done to get the information. She wanted to be the one to tell Luke the truth first. Still, it didn’t sit right with her. This would be a good source for Luke to squeeze and chase down, but she was putting herself and her marriage first. Maybe she could push Toad to get herself back there again.

“And the rest I overheard from a conversation at the club,” Riley said. It was technically the truth.

“Well, kid, you’re a natural at this,” Jim said, standing up and putting on his coat. Keep it up. Whatever you’re doing to get us actionable intel like this, keep on doing it. Understand?”

“Yes,” Riley whispered and nodded. Jim left, and Riley took a sip of her coffee. She opened a pack of creamer and went to pour it in before deciding against it. She couldn’t stand the sight of it. She could still feel Rico’s load warming her throat and stomach. Little did Jim know exactly what he was asking her to keep doing.