Undercover Mother

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A female cop is forced to have sex with her son's friend.
8.9k words
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Part 1 of the 2 part series

Updated 06/09/2023
Created 08/25/2018
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Karen Troy tapped her pen on her desk keeping a steady rhythm while the eyewitness sitting across from her droned on repeating for what seemed like the hundredth time the tale of woe surrounding her neighbor's supposed theft, and vandalizing of her car.

"I know it was him, detective, he has never forgiven me for backing over his prized rose bushes last summer. The bastard has had it out for me ever since that time!"

"So...You think your neighbor stole your car in retaliation for your malicious murder of his roses?"

"I know it sounds a little crazy, but trust me that man is nuts about those roses. I wouldn't put it past him."

Karen did her best not to roll her eyes taking down the victims statement in her tight handwriting. When she had made detective the previous year, she had thought it would be her ticket to a life of more exciting cases, but it seemed as if the only thing her boss was interested in throwing her way was the most trivial jobs he could find. She finished taking down all the pertinent information she could glean from the older lady across from her and sent her on her way with a promise that she would get a call if anything turned up.

"You going to interview the neighbor? It sounds like he had a strong motive," laughed her partner after the victim had left.

"Stick it, Howard! God, just once I would like to get an assignment with some real meat on its bones. You know what I mean?"

"It beats running prostitution stings doesn't it?"

The mention of her past work in the sex crimes unit made Karen wince, and frown sternly across at Howard Mannix. The two of them had been put together just a few months ago, and he never tired of ribbing her about her history before making detective. It was true that her beauty had gotten her tabbed to play the fake whore on many occasions. She had made plenty of arrests while doing it, but it bothered her that she got those assignments more because of how she looked in tight clothes than because of her abilities as a police officer.

Her retort was cut off by a voice from the direction of the captain's office.

"Hey, Troy! Captain Mercer wants to see you!"

Karen rose from her desk and walked briskly across the room with one last dirty look over her shoulder at her partner. She stopped just outside the door to pull herself together hoping that perhaps this time there was a case worthy of her talents waiting for her on the other side.

"You wanted to see me, Captain?"

"Have a seat, Detective."

Rick Mercer looked up from the file folder in front of him. He prided himself on being a fair cop, and an even more equitable boss, but it was hard not to see Karen Troy as anything other than a woman. He had grown up in an old school family where the woman stayed home and raised the kids while the man went out to make money. On paper, Karen had all the right credentials, and her arrest record was exemplary, but he still felt uncomfortable relying on her for the hard cases. Still, the one that was sitting on his desk right now should be right up her alley based on her experience.

"Karen, I have a special assignment for you. It's undercover work, and there is going to be an element of danger to it certainly, but the pay off could be huge in terms of protecting the public."

"I'm listening, sir."

"There is a local gang running drugs, and prostitution rings around the city. Their leader is a guy named Max Kessler. This guy is a real piece of work. He has been linked to a number of homicides, but we've never been able to get any evidence that would stick. Every time we have managed to get a witness to something he was involved in Kessler has gotten to them and intimidated them into not testifying or just removed them from the picture. The good news is we may have gotten a break. An informant on the inside got a tip that there is a big shipment of drugs coming in some time in the next couple of weeks. It's big enough that Kessler is going to be there personally to take possession of it. If we could get the details of that delivery, we could be there to nab Kessler, and likely a good chunk of his gang along with him."

"It sounds very promising, sir."

"There is a problem. The informant doesn't have the time or place. This is where you come in. Kessler's most lucrative prostitution ring is run out of his club, The Dream Room, over on the corner of Stark Avenue. It seems that the madam that was taking care of the operation met with an accident, and they are in the market for a new lady to take care of things. We think our best shot at getting the information we need is to get someone inside Kessler's organization, and this is just the opening we need."

Karen frowned,"You want me to play the prostitute again?"

"Not a prostitute exactly a woman who runs prostitutes. You have plenty of familiarity with how these things work so you should have no problem passing yourself off as an experienced madam."

"I suppose," said Karen doubtfully.

"Look, detective, you wanted to get a real assignment, and this is a high profile case. If you can help us make this arrest, it would go a long way toward getting folks around here to take you seriously."

"I hear you, boss. O.K., I'm in."

"Good. We will set up a meeting for you at Kessler's club tomorrow."

The office door shut slowly behind her as Karen left. Captain Mercer watched her walking away with an uneasy feeling in his stomach. She had the background to pull this off, but if anything went wrong, and Kessler figured out she was a cop, then she wasn't going to get out of there alive.

Traffic was light on the way home, and Karen drove with the radio turned down thinking about what she had just volunteered to do. The captain was right that she had the knowledge to pull this off, but it was going to be very dangerous, and she had more than herself to consider. Ever since her deadbeat husband had left with his secretary five years earlier, she had been raising her son, Charlie, on her own. He was a fine boy, kind, and handsome with a talent for music that impressed her all the more since she couldn't carry a tune. They had just celebrated Charlie's eighteenth birthday the previous weekend. He had been devastated when his father left, and she hated the thought of what it would do to Charlie if something happened to her on this job.

She had to park in the street when she arrived home because there was already a car in her driveway. The battered-looking old Ford Mustang belonged to her son's best friend, Ronnie Foreman. Karen shook her head as she walked past the car, and took the steps up to her modest one-story home. The truth was that she didn't approve of Ronnie. He was a bit of a troublemaker and was always getting himself into messes. There had been more than one occasion that he had been arrested for petty theft or driving while intoxicated. She knew he had a tough home life with an absentee father, and a mother with a severe drinking problem, but it didn't excuse his behavior. The only reason she hadn't banned Charlie from spending time around him was that the two got along so well, and she hated to disrupt Charlie's life more than it already had been.

The music was blaring down the hallway. Karen laid her purse on the table near the door and walked toward her son's room.

Ronnie Foreman sat on his best friends bed reading the lyrics to the song they were listening to from the insert he had pulled from the scratched up CD case.

"Man I tell you, The Monks are an amazing band. These lyrics are like poetry, dude!"

"I think you might be overstating their abilities just a little," laughed Charlie.

"I grant you they lack your God-given talent to spin words into song, my friend," chuckled Ronnie in reply.

"I think Charlie has them beat hands down," said Karen from the door.

Ronnie lowered the sheet of paper in his hands and felt his heart rate rise in the opposite direction. No matter how many times he laid eyes on Charlie's mom, he never got tired of looking at her. She was the very definition of an M.I.L.F as they say on the street, a mother I would like to fuck! Her dark brunette hair surrounded her perfect oval face in long waves setting off her green eyes. As she moved across the room to hug Charlie, she smiled pulling her full lips back from her even, white teeth. The conservative outfit she was wearing didn't show them off, but Ronnie knew she had a spectacular set of large, round breasts that on the rare occasions he had seen her in a bathing suit put most other women's to shame. Even in her late thirties, Karen Troy was a looker, and his fantasies about her had been many and varied.

"I'm going to start some dinner. Are you staying to eat, Ronnie?"

"Thanks, Ms. Troy. I would appreciate it."

When she left the room, Ronnie took a long look at her tight ass as it wiggled its way out the door.

"Damn dude your Mom is so..."

"Don't say it, Ronnie! I've been listening to you pine for my mother since we were in middle school. It's starting to get old."

"I can't help it if your mom is a gorgeous lady!"

"You could at least keep it to yourself," said Charlie tossing a pillow at his old friend.

"Ha! Whatever, man. I hope she makes spaghetti. That woman can cook almost as good as she looks."

Dinner was, in fact, spaghetti, and Ronnie scooped a generous portion from the bowl on the table. Karen watched him shovel the food away like it was his last meal. She strongly suspected that he didn't get fed regularly at home. He was a little on the thin side, though he ran track at school which might explain it as well. Ronnie was quite a handsome young man, with the curly dark hair around his swarthy face revealing his Italian background. His dark eyes shined in the light from the candles on the table. In a way, he reminded her of her college boyfriend, Jimmy, who had also been a tall, thin Italian. They had dated for a couple of years before his family had moved back to the old country, and Jimmy had decided to go with them. The one thing she remembered very clearly about him was the large size of his sex organ, and how well he could use it. For a moment she caught herself wondering if it was an Italian thing, and if so would Ronnie be as well endowed, but she quickly crushed that thought.

"Sick Karen! Thinking sexy thoughts about an eighteen-year-old!" she admonished herself.

It was most likely because she hadn't had sex since Charlie's father had left. Most of the time she didn't even think about it since she was so busy with work, but every once in a while her body would remind her that she was still a woman with needs.

"Well, that's what they make vibrators for after all," she thought as she took a bite of spicy meatball.

"I hear the track team is looking sharp this year. You guys might even have a shot at a state title," remarked Karen.

"We will see. I've been working out extra hard to get ready, but you never know. It's a long journey," replied Ronnie.

"Ronnie's just pissed because the coach told the team no sex during the season," joked Charlie.

"Dude!"

The whole table dissolved into laughter as Ronnie turned bright red.

The boys helped clean up afterward before they went back to Charlie's room while Karen sat on the couch going over a dossier on Matt Kessler. He was a real slimeball with his fingers in many illegal pies. It would be a pleasure to get him off the streets. She was lost in thought, but her attention was drawn to the hallway when the boys went walking by headed to the front door.

"You guys going out?"

"Yeah, Mom. We're just going to meet some folks down at the record store to hang out."

"Don't be too late it's a school night."

"No worries, Mom."

Charlie and Ronnie walked side by side. The record shop was only about five blocks from Charlie's house and given his interest in music they spent quite a bit of time there. As they crossed the street near the intersection where the store sat, Charlie couldn't help but notice how rough his friend's shoes were starting to look with the sole of one flapping loosely with each step.

"Hey...Uh...Ronnie. You know I have an extra pair of shoes you could borrow if you want."

"What? Are you saying my shoes are looking raggedy," said Ronnie in mock horror.

"Well..."

"Don't worry about it. I have a line on a new job that is going to have me flush."

"Is that right? Where? Like at the pizza place or something?"

"Please! Pizza delivery! I am so far above that sort of manual labor."

"Then what do you have lined up?"

"Just you wait, and see...the money is going to be rolling in," said Ronnie cryptically.

Charlie grinned indulgently at his friend letting the subject drop when they entered the record store.

THE LIONS DEN -

The room was smoky, and it burned her eyes a bit as Karen Troy stood across from the oak desk where Matt Kessler looked at her carefully. He gave off the appearance of an old-world gangster with his nicely tailored suit, and a long cigar burning between his fingers. His hair was slicked back on his head making his large, hooked nose even more prominent than it was already. The most striking thing about him was his eyes that were cold looking, like the eyes of a plastic doll. If there was a flicker of humanity in there, Karen was at a loss to find it.

"So, Holly...Herman here tells me that you ran a very profitable brothel in Nevada,"

"Yes, that's right. My girls played the game the right way. No skimming, and we kept the clients happy," said Karen answering to her undercover name.

"I need someone I can trust in this position, and I don't know you which makes me nervous. That being said, Herman here has served me loyally for many years so if he vouches for you I guess we could try this on a trial basis."

"Hey, I'm just asking for a foot in the door. If you like the results, then we can talk about a longer partnership."

"Very well. Herman, take her around to meet the girls, o.k.?"

The hulking gentleman next to her led Karen from the room shutting the massive oak paneled door behind them.

"I guess you're in the door," said Herman who in reality was the very informant who had tipped the police to the impending drug deal.

"Why didn't you just get the information we need since you're so close to Kessler?"

Herman shook his head slowly,"Too many eyes on me. That's the problem with being close."

"I see. Then how about the grand tour?"

The pair left the hallway and descended a flight of stairs down to the club proper. Their exit came just in time for them to miss a second group approach the same door they had just left. Three boys stood shoulder to shoulder in front of Kessler's desk a moment later, and he looked them over dispassionately.

"So you boys want to work for me, huh? Doing a little of this, and a little of that? I think something can be arranged. If you three do as your told, and keep your mouths shut you will do quite well for yourselves. Fuck up, and I will have your balls in a sling!"

"We got it covered," said the tall, dark-haired young man in the middle.

Ronnie Foreman looked around the ornately decorated office, and swallowed hard. It was clear that this Kessler guy was no one you wanted to mess with, and he was starting to have second thoughts about this whole deal, but it was too late to back out now. It seemed better to at least put on the face of a confident man whether he felt that way or not.

Kessler continued to pull away at his cigar a bit longer before dismissing the trio with a wave of his hand. The scar-faced redhead that had led them in took them out, and down a back stairwell where he gave them each a bag of illegal drugs, and careful instructions on what they should do with them. Ronnie took his parcel slipping it under his jacket and left hoping he wasn't making a grave mistake.

Karen spent the day meeting her charges. It was the typical group of women beaten down by life and haunted by a combination of bad luck, and worse choices. She was glad this was a short-term assignment, and with any luck taking down Kessler's operation would free these women from the prison they had been consigned too. She returned home taking great care to make sure that no one followed her. It had been a long day, and she was looking forward to a nice hot shower, and a good nights sleep. The boys were cranking the music as usual when she came in, and she stopped briefly to check in before slipping off to her bedroom.

Ronnie watched as Charlie, and his mom talked in the doorway before she left with a wave. He had spent his afternoon trying to spread the product he was carrying around campus without drawing suspicion. So far he had been fortunate, and the large roll of money in his pocket was evidence of the success he had enjoyed. Excusing himself to hit the restroom he took a long piss cleaning his hands carefully. He was about to head back to Charlie's room when he heard the sounds of Ms. Troy shuffling around her bedroom, and noticed that the door was cracked open. The temptation to take a peek inside was too much, and he slipped quietly up to the door placing his eye close to the crack. He was disappointed to see that she had already put a robe on before heading into the bathroom, but at least he got a look at her long, slender legs, and a hint of her full chest pressing at the folds of cloth holding them back.

"Just my luck. I would give my right nut to see that woman naked," he thought.

IT TAKES TWO TO TANGO -

The investigation went better than Karen could have hoped, and by observing Kessler's movements, she had been able to ascertain when his office would be empty. She knew from experience all the places a person used to hide valuable information and finding the false bottom in his desk drawer had been child's play. The timetable for the drug shipment was in her possession now, and all she had to do was get out of here with it. The simplest thing would be to wait for the lunch break, and that was precisely what she was doing just killing time when Herman found her.

"The boss wants to see everyone in the conference room," he said nervously.

"What is going on?"

"He thinks someone was going through his desk. I guess he has some way of knowing. I don't know, but he is pissed. It wasn't you was it?"

"No," lied Karen not wanting to tip her hand. She had been so cautious she couldn't imagine how he had known she had been in his desk.

They filed into the conference room along with six others. It was pretty much all the high ranking employees working in the club. Kessler came in smoking one of his foul-smelling cigars as usual.

"I'm glad you all could make it," he said sarcastically as he sat at the head of the table.

The look of fear in the eyes of everyone around the table made it clear that this was not a meeting to take lightly.

"We have a rat in our midst folks. Someone was going through my private files. Everyone in this room has been with me for quite a while. I know that sadly that doesn't guarantee loyalty, but it is a place to start. That means the most likely suspect would be you, Holly.

Karen tried to stay calm,"I can see how you could think that way, but I assure you I haven't been anywhere near your office."

"Hmm...I think a proof of that loyalty is needed here, Holly. You say that you are the obedient servant, well, let us find out."

Kessler pushed a button under the table, and a moment later the conference room door opened. Karen kept her face impassive, but it wasn't easy because two men entered the room, and one of them was Ronnie Foreman! He glanced over at her, and she just managed to shake her head softly hoping he would get the hint not to let on that they knew each other.

"Ronnie, my boy, have a seat," said Kessler.

One of Kessler's men pulled a chair away from the table setting it back toward the wall, and pushing Ronnie into it.