Undercover Rookie (closed)

Chloe had working for the better part of a year to try to gain a foothold with anyone of importance in the organization. Up until now her efforts had only resulting in her being passed around as a fuck toy by anyone looking for some fun. Had pain and pleasure not been so inextricably linked in her mind she was surely pretty enough to catch someone’s eye. The enthusiasm she showed as she endured their abuse, even when she didn’t want to, forever doomed her to the roll of a play thing though.

When the young Latina slammed her head onto the table Chloe let out a moan then lifted her hips in anticipation of what she knew was coming.

****
After a few tense moments Roberto excused himself to take some calls leaving Manuel and Rob alone in the room eyeing each other. Since Rob had no choice but to with with him, he did his best to bury the hatchet before he was forced to lodge it in Manuel’s forehead.

“Look man, I know the pressure you’re under being the bosses kid. It sucks but it’s time to push past that and put in the work to take the place you want in the organization. I’m willing to do my part, let’s try to make a fresh start alight?” Rob said hoping to establish some sort of workable rapport.

Manuel looked at Rob trying to suppress just how amused he was by his weak attempt at diplomacy. “This dickhead doesn’t even realize he’s already dead.” He thought to himself visualizing the day the Russians make good on their deal and take care of all of them leaving only Manuel standing.

“Yeah, sounds good.” Manuel finally said, extending his hand. For now he’d play along but when the time came he was going to be sure he was the one that finally took Rob out.
 
As the strap on was secured, Dianna gave a little yelp as the woman gave her bum a little tap, but then without any hesitation she buried the toy deep in the blonds waiting cunt. Wrapping her fist further into the blonds hair, she started to pump into the bitch.

---

Roberto cursed as his stupid son had forced his hand this way. He wanted his boy to turn into a leader, but it seemed he would never outgrow his fuckboy faze. Walking out he saw his wife looking at Chloe, and he was surprised to see that cop bitch going to town on the little blonds ass.

Walking up to his wife he swatted her bum, and knowing what he wanted, she immediately kneeled and started to blow him while he watched Rob's girl trying to out fuck one another.
 
Chloe gripped the edge of the table as her eyes squeezed shut. She hated the way her body was responding to the spic bitch fucking her but here she was.

“Oh fuck. Yes! Own that pussy.” She grunted out through gritted teeth as the Latina hit all the buttons to light up her body.

“God she really does love this shit doesn’t she.” Roberto said as he began pumping his cock deeper into his wife’s throat. There were times he loved to watch maybe more than actually do and this was one of those times.

“Tear that pussy up.” He called out urging Dianna on.

Manuel and Rob emerged from the office and were greeted by the scene playing out in the parlor. Manuel let out a whoop then took a step towards the women but was stopped in his tracks by Rob’s hand on the back of his neck.

“This is where it starts. Just watch, it’s not always just about you.” Rob said trying to hold the young man back.

Manuel didn’t like it at all but did as he was told and took in the show playing out before them.
 
"Look that Bitch in the eyes when you fuck her."

Roberto yelled as he roughly pushed his cock deep down his wives throat. He smiled at the awkward moment between the ladies. It was clear that Chloe didn't really want to play ball, but to his surprise the cop knew how to handle herself.

Kicking the blonds leg to the side and flipping her on her back, she waisted no time in grabbing a hair full of blond hair on both sides of her head and start pumping the oversized tool into the woman again.

Chloe still throwing daggers at the spic, yelped as the woman pulled her hair harder and spat in her face.

"Smile Bitch"

She yelled and followed it up with a hard slap as the blond was too slow to comply. D didn't know where the aggression was coming from but seeing the blond break eyecontact before plastering a fake but pleasant smile on her lips fueled her passion, and instead of letting her hand go back to the blonds hair she started to roughly molest the blonds chest
 
“Oh fuck!” Chloe cried out as her body began to respond. She hated that she couldn’t help it. She’d much rather kills this bitch then give her the satisfaction but there was nothing she could do as she gave in to her body.

Chloe’s fingers strummed at her clit as she bit down on her lip. Her body started to shudder as it started to hit her.

“Aaaaahhh” she cried out as her muscles attempted to clamp down on and halt the assaulting member.

“Yeah, fuck that whore!” Rob called out as he watched Dianna pound the blonde through her orgasm.
 
"Don't you fucking dare easing up on that Bitch!"

Roberto called out, so between that and Rob cheering her on, she grabbed the girls hand to push it away from her clit and D sounded into her even harder, she almost felt sorry for the girl as she knew how sensitive this could be.

Pulling off his belt, Roberto tossed it to the women, and as his wife kept impaling her throat on his cock said.

"Did you give this whore permission to cum?"

Looking at Rob for guidance on what to do, D saw the cruel smile on Manuel's lips and the fear in the blonds eyes and knew what she had to do. Rob had warned her to never hold back or things would turn against her, so grabbing the belt and looping it around her fist to shorten it, she started to lash the woman's stomach and tits as the girl tried her best to suppress the visible ques of her orgasm.

Pulling out his cock out of his wife's hungry mouth, Roberto moved closer to the two women. His cock coated in saliva as he stepped behind D, whispering surprise at the disrespect she was tolerating.

Manuel, seeing a chance to get involved again, got stopped by Roberto's wife, who smacked his leg with her strapon.

"Last warning" she said as it seemed the kid was having a hard time learning
 
Chloe had seen this scenario play out before and could recognize the mob mentality start to take hold as the men began to encourage the Latina to be rougher and rougher. One day she hoped to be on the other side of things but it never seemed to work out that way. Her well know penchant for pain and pleasure virtually assured they'd continue to use her as their toy.

"Is that all you have cunt. My mom hit harder than that!" she spat out trying to urge her one but at the same time letting that Latina know just what she thought of her.

"Oh shit! That sounded like a challenge." Roberto whispered into Dianna's ear as he wrapped his arms around her and start to roughly grope her breasts.

Rob was encouraged that the first real taste of power Dianna has had since this whole ordeal started might help move her in their direction some. He was eager to see just how carried away she'd let herself get with Chloe.
 
"You Bitch"

Dianna spat out as the girl challenged her and she found herself slapping the belt down hard. Feeling Roberto molest her small breast as he lifted up her skirt to push his wet cock up against her soft bum, she made sure not to recoil but seeing the blond smirk at her, she started to see red.

---

Chloe smiled as she saw Roberto move in on the Latina, while her lashes were not soft, they did not compare to anything the men of this gang had put her through already. Seeing the anger contort the little bitches face her smile grew even bigger as she could see she was losing control.

She bared her teeth as the Latina clearly frustrated clenched a fist and seemed to try and hold back, but as Roberto smacked the Latinas ass, she brought down her fist on her stomach. For a second the whole room was silent apart for the gasps of Chloe trying to catch her breath. Then under a string of Spanish expletives Dianna started to rain down hits on the woman as if they were in the UFC.

---

Seeing what she thought was a relatively vanilla woman snap under the pressure, Tia winked to her husband as she knew just how much he enjoyed this, then not wanting to be left out of the fun, she pushed her ribbed strapon in Manuel's hand, who recoiled at once, before taking a hood grip on it and stroking it, knowing he didn't want to have to be ordered by his dad to do so.
 
Rob had assumed that everyone had gotten this stuff out of their system the night before but it was becoming obvious that wasn't the case. He reflexively winced with each blow Dianna delivered to Chloe and he was starting to worry that she was going to revisit all the abuse she'd endured the last few days on that little blonde.

Manuel was kind of shocked when Tia guided his hand to the strap-on and forced him to start stroking it in front of his father. For as long as he remembered Tia had made it her mission to try to keep him in line when his father had failed and he wasn't eager to admit to his father the methods she used.

Manuel gave Tia a nervous look over his shoulder as he felt her fingers close around the back of his neck.

"No, not here." he pleaded in a hushed tone before she shoved him toward the table next to Chloe.

Manuel knew better then to fight back. His only hope now was that his father would see what's happening and put a stop to it. Tia stepped in behind Manuel then let a long drip of spit fall from her lips and land between his tanned cheeks before pressing in with a strong thrust.

"Aaaaghhhhh" Manuel cried out as his step mom's assault began.
 
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Roberto smiled as his hand reached between the girls legs to find them dripping wet. Whispering in the cops ear he said.

"You are a nasty little slut, to get this aroused by her pain."

The words of the man sunk deep into Dianna's gut as she realised she was indeed turned on at the moment as the marks on the body of the girl started to pile on. She wanted to say it wasn't because of that, that it was because of Rob's attention earlier this morning, but as the man roughly curled two fingers I to her, she found nothing but moans escaping her lips.

Without thinking she grabbed the blond by the hair and pulled her off the table as Manuel stumbled up against the table next to them. Then spat at the blond and said.

"Suck my cock! Putta"

And as the girl took the strap on in her mouth she understood why guys like the sight of a woman submissively on her knees like this. Pushing her against the frame of the table, Diana started to thrust into the woman's face as she used Roberto's finger who had stopped moving, to get her off.
 
It took everything Rob had not to bust Manuel’s balls for getting pegged by his step mother but one thing he knew he couldn’t do was get in between Manuel and his parents. In order to keep from laughing he turned his attention to how Dianna was brutalizing Chloe.

Chloe let out a scream when the Latina slammed her to the floor and began pumping the dildo onto her throat. Ever time she thrust it in it felt like it was tearing at her esophagus and ripping her vocal cords. She’d had plenty of cocks shoved down her throat but nothing ever compared to the pain she was feeling now. She out every ounce of energy she had left into trying to get away but it was no use.

Finally the searing pain caused her to black out and she crumped down only held upright by the Latina’s grip on her hair.

“Holy shit, I think she may have had enough.” Roberto said when he noticed the girl was unconscious.
 
Having been to busy looking at how Manuel was being fucked by Tia, and working her own pussy on the crime bosses fingers, D had not noticed the lack of resistance as she had started to rythmicly knock the blonds head into the table. Only when Roberto of all people said something about it, did she looked down and stopped.

Pulling out her strap on and letting go of the blond hair that was now stained with some red, for a second she feared she had killed the girl, but as her head hit the floor, everyone could see her chest rising and falling shallowly.

"Holy shit Rob, that is only little slut you brought home."

Roberto exclaimed and to her horror Dianna, noticed she was still grinding on his hand, worse as he took his fingers away a disappointed whimper escaped her lips.

"Take that killer shlong off and get into position."

He growled as he noticed that Manuel was actually rock hard as Tia was fucking him, and he had to hold back from shooting both of them.


Obeying the order, D undid the strap and placed in on the table. Then not knowing what side to offer up to Roberto, she kneeled to all fours in between him and Rob, but faced Tia's ass and Chloe's unconscious body, so the men could choose what they wanted.
 
Manuel couldn’t believe this was happening in front of everyone. He tried his best to will down his erection but it was no use. As much as he hate when she did this to him there was little he could do to stop it from happening. He cursed under his breath as her thrusts got more forceful.

Rob looked down a Chloe’s unconscious body and laughed.

“Damn, remind me not to let you get the upper hand on me.” He said as he kicked her limp arm out of the way. “Don’t worry, I’ll be a little gentler.”

Unzipping his pants Rob produced his cock and teased it across Dianna’s lips waiting for Roberto to make his move.

Roberto seemed fine with Rob’s selection as he kneeled down behind Dianna then gripped her hair and pulled her head back as he shoved his cock into her. With her head tilted back it provided Rob the perfect angle to push his cock down her throat.
 
"Oh Fuck... "

Dianna said just before Rob muffled her, by stuffing his cock down her throat. The young lesbian was not sad about this as she was about to demean herself as the crime bosses cockpit hit the spot. She couldn't believe just how desperate she was for an orgasm and she didn't care if it came at the hand of a man.

As the men started to pump into her, it was clear they had done this before as their rythmes worked perfectly off one another.

---

Tia smiled, for years now she had groomed the little dipshit to submit to her, knowing her husband would never let a man who gets pegged take over the organisation , leaving her unborn child as the logical heir. But as she would start to show and her manulipulations would be too obvious to pull off.

Pulling out of the thight buns if Manuel, she pulled him down to his knee's and shoved the dildo into his mouth, the moment amplified by the tears in the little pussies eyes. After a few strokes she told him to lay down on his back and grab his ankles, a position she know he hated even more.

Kneeling in front of him, she locked eyes with him as she pushed back into his ass, and started to fuck him again, making his cock flop obscenely with every stroke, knowing that when he blows he will shoot his load onto his own face.

Hearing the flesh slapping against flesh sounds of the men fucking Rob's new toy, get harder and harder, she almost felt sorry, the girl was going to be Roberto,'s anger relief for seeing his sun take it like this.
 
Manuel felt it building and tried to fight it off as hard as he could. It was a position he knew well and it always seemed to happen. That constant pounding into his prostate sent him over the edge every time whether he wanted it to or not.

Within minute's Manual let out a pained grown as streams of cum jetted from his flopping cock coating his chest and splashing across his face.

"What the fuck?" Roberto growled out as he continued to pound into Dianna.

He wasn't quite sure what he'd witnessed but it was definitely something he'd need to address later. After he was done with the cop.

Rob had largely missed the spectacle that Roberto had witnessed and continued to fuck Dianna's mouth until he felt his balls begin to tighten and his back hunched. He repositioned his hand to the back of her head then thrust deep into her mouth one last time as deep has he could get before dumping the second load of cum down her throat for the day.

As Rob stepped back and leaned against the table Roberto, unencumbered by Rob on the other end of her, pressed Dianna's face into the floor as he pumped into her.
 
Tia smiled as Manuel splattered his semen all over his chest and face. She had often used this type of climax to gaslight the man into thinking he enjoyed the pegging, knowing he would probably never google the phenomenon that inevitably triggered the orgasm.

"Stay like this and don't you dare whipe that cum off"

She said as she stepped up to Rob to watch Roberto fuck, leaving Manuel soiled and holding his ankels by his head.

---

Dianna relaxed her throat and made a swallowing motion as Rob grabbed the back of her head and pushed his cock all the way in her throat, knowing this made it less painful. She moaned as the man coated her throat in his hot semen.

When Rob took a step back, she took a deep breath and yelped as Roberto pushed her head roughly into the floor, bumping her nogging. But a chuckle of Roberto, made her blush as she realised he was not moving anymore, and all of the fucking was because she was throwing her ass back on him.

Fighting against the urge to beg, she bit her lip but after what felt like an eternity she broke down.

"Please pappy, please fuck me harder.!"

She called out, but again Roberto only laughed and spanked her gyrating ass.

"Tell me what you are!"

He said as he firmly took hold of her hips with both hands, part promise to what was going to happen, but also forcing her in place and in doing so frustrating her build up. Whiteout any hesitation the cop said.

"I am your whore!... please just use me as your lucky meat... please"


She said and more, shocking herself in how much she was debasing herself but also with how easily it was. But as Roberto squeezed her hips hard and launched into a rough assault of her private part, she didn't care and kept telling him what he wanted to hear.

---

Roberto smiled at Tia and Rob as the cop submitted fully to him and intermediatly gave his son glances everytime he felt like he was about to blow his load. Then as the cop announced loudly that she was cumming he slammed his fist hard on her kidney, making her seize up around his cock. The girls hips collapsed to the floor, but with his cock in the vicegripp of her pussy he followed her down and kept jackhammering her hip into the floor in the pronebone position, until finally his balls exploded and je shot his semen deep inside of the girl.
 
The awkward silence in the room was only broken by the sound of Dianna's gasping breaths. Roberto stood up then pulled his pants up. He had no idea what to say about what he'd just witnessed and decided it was better to address that with a cooler head.

"I'm going back to my office." he said before storming off.

Rob looked down and noticed that Chloe still wasn't moving.

"Tia.... um, you might need to get her checked out." he said noticing the patch of crimson hair on the back of her head was getting larger.

He knew he needed to start getting Manual up to speed on his takeover plans but, looking at him, it seemed like he needed some time to get himself together after his ordeal.

"Manuel, why don't you come by my house later after you get.... ummmm.... cleaned up. We can talk about things then."

Grabbing Dianna's arm he started to pull her from the floor to get her moving.
 
"Ally I know you want to nail those assholes but you need to pull your asset out. The Russians are just welcomed some ex spetznas, and that means only one thing."

Ally cursed, she knew Trask was probably right but there was still a part of her that didn't want to take any risks with this case, even if it cost another cops life.

"I understand, I will set up a meeting so I can get you the Intel to fix your leak, and extract the asset."

Quickly texting Dianna, she asked them to meet at a highend sex club, and she added a Selfie with the quote that Rob knew what to bring to the party. Dianna would also know that this meant trouble as this was an emergency address.

---

D was wobbly on her feet as her side still ached from the donky punch, worst off all she still felt horny as if the orgasm had only made things worse, not better, but all that went away as she saw Ally's text. She showed it to Rob as apparently there was also a message for him, but the rookie worried as this was about the last place she wanted to meet her handler as it meant that there was some big issue going on.
 
Rob looked at the phone then nodded silently before looking at what each of them were wearing.

"We probably need to stop by the apartment and change." he said, manufacturing an excuse to go back by the apartment and get the drive from the safe. He knew the less Dianna knew about his and Ally's side arrangement the better although it was possible she was going to find out at the club anyway. If she did, that was going to be on his handler, not him.

The two of them climbed into the Range Rover and drove back to his apartment in silence. He could tell Dianna was still trying to process what happened. He didn't know her extremely well but he was pretty certain she was as caught off guard by her aggression as everyone else was. He gave her the space to process that as they drove.
 
D was stressing out in the car as the two of them drove in silence. Rob had not commented on the situation and that made her nervous, she had expected him to make a joke about her being a good girl or something in that treat, but his silence on the matter twisted her gut painfully.

She had wholly crossed the line with the blond and she felt sickend by what she did, but somehow knowing Rob also thought she went too far made it so much worse. She also worried the hell out of the meeting with Ally, she could not know about what had happened yet, still the timing made D nautious with stress.

As they arrived at the apartment, she remained in the car, telling Rob that since it was a meeting in a sexclub, the underwear she was wearing would do. It was only when he had left the car, and she had checked if she had a matching set on, that she noticed how soiled her panties were with her own juices and Roberto's load.

So sliding them off she unconsciously started to play with her clit, as she waited for Rob to get back down.

---

Antoine, the maitre d of the club, shook his head when he saw the hottie requesting a playroom for her, Rob, and his girl. He knew that the crime boss was good with the ladies, but he was surprised at just how many women would throw everything away to be with him.

Giving them the gangbang room, he send the man a message to see if he wanted an audience watching them or privacy. After all the girl asked for a private room, but a beauty like her would draw in a lot of eyes.
 
Upstairs Rob changed into something a little more stylish even though at that place he didn't expect his clothes to be on for long. He pulled out a fresh black silk shirt and some nicer slacks before opening the safe and pulling out the drive. He knew Roberto wanted Ally taken care of but he got the sense that now wasn't the time. He needed to see what the meeting was all about first before he could act on that.

On the way down to the garage he got a text from his guy at the club.

"By all means. I think she's going to want as many people watching as possible. She really likes an audience." he replied before slipping the phone back into his pocket.

Entering the garage he waved Dianna out of the Rover and directed her to the Lambo. There was no need for the extra space and he liked the eyes on him when he rolled up in it. She grudgingly climbed out after fiddling in her lap for a minute then walked over and climbed into the other car.

15 minutes later they were pulling up in front of the club. Rob tossed his keys to the valet then walked inside with Dianna not far behind.
 
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Dianna followed Rob to the entrance of the club and wad surprised at just how highend the place was. Being from a small town she had very much different ideas of how a sexclub was supposed to look.

Once inside though she was greeted with a mix of a highend hotel and a sexshop, with way more people inside than she thought possible. Arriving at the counter, she started to take off her dress, joining the many nude women already in the hallway. Then grabbing a leashed chokerneckless, she put it on, handing Rob the leash and dropping on all fours.

She had no idea why she did this, but seeing the men look at her and Rob appriciatly, as they past others in a similar position, she figured she chose right.

---

Abby was surprised that the small playroom she had booked, had turned into a larger one. The room had mirrored walls and ceilings, beds, sofa's beanbags, and all of the toys she knew, and some that were new to her.

Looking around she was startled when an electric sound was heard and every other mirrored wallpanel turned to glass. Looking at the other side of the one in front of her she saw a young girl being fucked by several older men, who merrily waved at her. She awkwardly waved back and moved away, only to be greeted by a bunch of black guys who were softly stroking their oversized members while looking at her hungrily through the glass.


Not knowing what to do exactly she just gave them a long look over as if she was sizing them up, which in all honesty, she was. Then hearing the door behind her, she turned around and was surprised to see Rob walking in with a naked Dianna, crawling sensually on all foors to the delight of another gentleman who kept walking, but almost dislocated his neck to keep staring at the Latina's bum for as long as he could
 
Rob walked in and glanced around the walls seeing how many people were watching them.

"You feds really know how to conduct clandestine meetings don't you." he said noting how public the place was. He knew that nobody outside could hear them but there were definitely enough watching to make the risks very real.

Rob led Dianna to the center of the room then sharply tugged at the leash causing her to rise up on her knees in front of Ally.

"Should we put a collar on you too?" he asked looking over her outfit then up through the glass behind her. "I think that guy might like it."

Rob nodded his head toward one of the black men that had walked close to the window and was stroking his oversized cock starting at her.

"You think you want some of that?" He continued with a smirk.
 
"It would clash too much with my outfit."

Abby said as she took a seat on a chair, motioning Dianna over to her. Thinking it would be better to keep up the act, even if it was clear Rob thought it was safe to speak openly.

As Dianna crawled over to her, she looked at the woman and beside some bruising that clearly showed she had been active, she seemed alright.

"You have a Russian problem Rob."

She said, but not offering up more as Rob would milk her dry and leave her to hang if she let him. To her surprise she felt Dianna's warm tongue on her snatch as the rookie had pushed aside her bodice and had started to eat her out skillfully. So putting a hand on the ladies head, she acted as if it was all part of the plan for their viewers
 
“Russians?” He said trying not to move his mouth much suddenly more aware of the risks of talking about this with people watching.

He’d been so preoccupied with the various cartels he hadn’t even thought of threats from the East. It was only a matter of time though before they used their extensive resources to muscle in on their turf.

Rob circled behind Ally and gathered her hair in his hand before yanking it back then leaning into her ear as his other hand groped her breast.

“If you’re intent on taking us down, it sounds more like you have a Russian problem.” He hissed in her ear. “If you don’t like how we operate your sure as hell not going to lie how they operate when they move in to fill the void.”

Rob punctuated his words with a firm pinch of her nipples causing her to let out a squeal.
 
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