Rookie Lawyer – Part 4

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Title: Rookie Lawyer – Part 4

Author: The Chemist

Celebs: Anna Kendrick

Codes: M+F, Anal, DP, Oral

Disclaimer: I do not know Anna Kendrick. This is a story of fiction. I make no money from this.

When Anna Kendrick received the text from the man she had recently been fucked by in the bathroom of a fancy restroom, she was thrilled. The man was dangerous and edgy, making Anna wet at the thought of it. He explained that he would send a limo (a limo!) to her work to pick her up that evening and take her to a location.

With him, Anna was more carefree and liberal then she normally was, but she needed to know where they were going. He complied easily enough, informing her that they were going to the edge of town to a private establishment. She would be his arm candy for a game of high stakes blackjack.

“Hey Zooey, I’m going to knock off around 9 tonight,” Anna informed her boss.

“Really burning the midnight oil. Well, 9pm oil I suppose,” the quirky brunette commented.

“You know me,” Anna grinned. “I have a key and all the alarm codes.”

“Good. I’ll inform the security guard on the way out that he’ll have someone up here working until then,” Zooey replied. Impressed with the work ethic Anna, on a Friday night no less.”

The rest of the day seemed to crawl by but by 7pm most of the office had emptied out. Being the boss, Zooey knocked off even earlier, especially since it was a Friday and the rest of the group soon followed. That suited Anna just fine, as it allowed her to get some more work done since she knew the weekend may be a write-off depending on how tonight went.

The free time in the office also allowed the auburn-haired lawyer to alter her outfit and make it a bit more sexy. She had donned a form fitting pant suit today and though it hugged her body, it wasn’t the hottest outfit in the world. Taking a risk, whipped off her jacket and removed the white blouse she wore underneath then returned the blazer.

“Kinda slutty…but very sexy,” Anna observed.

Her statement really hit the nail on the head as she stood in front of the mirror. Her slender legs in high heels lead into her ass, which wasn’t a massive ass by any standards but was well formed with a cute little curve and roundness. Her eyes traveled further north where the only thing keeping her bare tits from being exposed was the button of the jacket. She’d removed her bra as well so her blazer gave off a massive plunging neckline with the lawyer able to pull it off on the fact that her tits were large and perky.

Anna couldn’t even remember how she killed the rest of the time, likely through a mix of paperwork, fixing her auburn locks that hung over her shoulders, and fixing up her smoky eye make-up. Around 9pm she started to close up, powering down her office, locking the office and making her out out front of the building.

“Ms. Kendrick?”

The voice came from a man in a uniform, standing in the front atrium of the building her law office was situated in. He wore typical limousine driver clothing, namely a decent suit with one of those weird hats. She followed him out, climbed into the back as he held the door open for her, then they were off.

It wasn’t a very far drive, maybe 20 minutes, but the entire time butterflies were fluttering in her stomach. She wasn’t nervous per se, more like she was curious. Anna had an idea of what would be waiting for her, namely Sam and his massive cock ready to fill her up again and have her scream his name. What she didn’t know were the details and that’s what was driving her crazy with assumptions.

“We’re here,” the limo driver’s monotone voice announced.

Anna hadn’t paid attention throughout the short drive, though now she was aware that her subconscious must have been. She remembered leaving the bright lights of the city and for them to be replaced by the desert-like environment that she currently found herself in.

“So happy you could make it,” Sam said after the driver helped the younger woman out of the vehicle. “You look sexy.”

“Flattery will get you everywhere,” she smiled as she accepted his kisses to each of her cheeks. “Just out of curiosity, where are we?”

“This,” Sam said, spreading his hands out to illustrate the building behind him. “Is the clubhouse of the golf course that I patron often. The owner of which is an excellent friend of mine.”

Anna nodded her head before reaching out and taking his outstretched arm. He tucked her dainty hand into the hook of his elbow, paid the limo driver discreetly with the other then lead the gorgeous lawyer inside. As he opened the door and took a step inside, Anna realized that there wasn’t a light on in the entire building.

Right on cue Sam withdrew a regular-sized flashlight and started walking further into the darkened space. Anna noted that they winded there way through a few corridors before entering a room that was as large as the atrium they first encountered when stepping inside the building. This room was different though for two reasons. Firstly because it was where Sam stopped their forward motion and secondly because there were three other flashlights roughly 20 feet away.

“What’s going on,” Anna asked, more intrigued then worried.

“You said you were very open minded sexually…I plan to satisfy that itch of yours,” he told her.

Anna was so focused on the implication of his words that she didn’t realize that her date had put down his light onto a nearby table. With his free hands he used them to wrap around the lawyer’s tiny frame and find her tits through her jacket. It wasn’t the first time he groped and kneaded her breasts but Sam was still shocked and impressed in equal measure of how a tiny girl like Anna Kendrick could have such big pillowy boobs.

She was disappointed when his strong hands left her tits after only a minute of playing with them, but he had his eyes on a different prize. They traveled over her flat stomach and into the waistband of her buisness suit pants, unclasping the button in the process.

“Mhmm…yes,” she moaned as fingertips rubbed over her snatch.

It was only a graze through panties but to Anna it still felt amazing. Sam repeated the trick once more before hooking his digits into her pants and pulling them down to her knees, exposing the black stockings the lawyer wore which were held to her slender thighs via an elastic. He showed off his multi-tasking skill by using his right hand to run through her underwear-clad pussy while his other went back to her great rack.

And Sam felt it was time to release her exceptional tits to his guest who were slowly creeping forward. Her lack of blouse or bra meant that once her jacket was open and rolled from her skinny shoulders then she was completely topless, her small pink nipples already pointy with excitement.

“Wow,” one of the men opposite the couple exclaimed.

Anna couldn’t help but smile as the unknown man complimented her sizable breasts. Sam allowed the three men an unobstructed view as he folded her expensive jacket and placed it on the table as well. The lawyer could still feel his chest against her back so she turned her hand so that she could rub his crotch through his trowsers, which instantly hardened.

“Mhmm…so skilled with a dick,” he whispered in her ear.

Let’s see if that skill translates to pleasuring 4 cocks at a time,” Anna thought to herself.

Sam helped out the disadvantaged woman by removing one of his hands from her tits in order to fish his cock out from his pants. Anna showed her appreciation by instantly wrapping her fingers around his thick member and stroking his length in slow pulls. Anna was pleased when he returned the favor in kind, albeit with his fingers gliding over her pussy through her panties.

Anna couldn’t take anymore of the slow build-up that bordered on teasing. She decided to do something about it so she spun around and kissed her date on the lips before dropping down to her knees seconds later. For as many times in two days, Anna found herself kneeling in front of the thug in a public place although this time she had an audience.

Hoping that she nor Sam would have stage fright, Anna didn’t let his rock hard cock go to waste as she took his head in her mouth and used her tongue to play with his slit. It gained a grunt from the much taller man as well as a fist balling into her long auburn hair.

“Damn you’re good,” Sam grunted as the smoking hot lawyer now licked all along his fleshy pole.

“You haven’t felt anything yet,” Anna remarked.

“Oh I remember,” he replied. “Which is why I’m going to fuck your beautiful face in front of our guests.”

Very few woman Sam had hooked up with in the past had been able to take him all the way down her throat, let alone be so forceful with them. Anna was special so he wasn’t going to pass up this opportunity. Grabbing her by the side of the head, Sam thrust his hips forwards so that half of his cock was in Anna’s skilled mouth.

Anna easily handled that warm-up thrust so now Sam started pulling her face in towards him at the same time. The first time her nose smacked his pubes and his balls whacked into her chin she coughed up extra spit but suppressed her gag reflex.

Sam savored the feeling of her lips wrapping around the very base of his cock while she showed off more talent by extending her tongue and licking his balls simultaneously. After a few more seconds he pulled her away and noted the vast amount of spit strings connecting her lips to his fleshy pole. With her throat now open to his cock and the extra lubrication, Sam was smoothly gliding along her lips as her nose constantly smacked lightly into the patch of thick pubic hair.

“Oh…hello,” Anna exclaimed.

The auburn haired girl had been keeping an eye on the three flashlight-wielding men opposite her, but during the blowjob her attention was broken. In that time, one of the men had approached her, squeezing her tits and tweaking her nipples. But what got the lawyer’s attention was when he took her wrist and made her form a fist around his erect cock.

“Do him now,” Sam told her, looking down into her eyes.

The topless woman didn’t argue, after all she knew what she was signing on her to a degree anyway. Swivelling around to face the mystery man, Anna opened her mouth and felt Sam’s hand on the back of her head pushing her forward. The pressure didn’t stop until the lawyer had the other man’s cock completely buried down her throat.

When Sam dropped his hand from her head, the other man did not take up the slack. Anna was fine with that as she was more than able to bob on his entire length, which she did time after time. Roughly a minute went by before she turned back around to her date for the evening and gave him a bit more oral pleasure, much to his happiness.

“Come to me…woman,” a deep voice beaconed.

Anna finished her long bob down Sam’s cock then turned over her shoulder to lick the tip of the second guy as well. Embracing her inner whore that she promised herself she’d become for the evening, the lawyer got down onto all fours and crawled like a dog over to the other men. Her pants around her knees prevented her from going fast, but they were only 10 feet away so it didn’t take long.

Who she assumed the more forceful of the men to be was the one who took possession of her head, more specifically her mouth. Anna took in a big gulp of air then opened wide as his dick slid along her tongue until it entered her throat. The mystery man bent over at the waist in order to help drive her face even tighter against his stomach, forcible making Anna almost cough from the depth that he poked down inside her.

“Gllkkk,” she lightly gagged, though there was no risk of coughing up.

This more aggressive blowjob continued and Anna felt tears in her eyes start to well up. A few times when the man held her down on his cock for more then ten seconds in a row she contemplated smacking him on the legs to allow her breath, but he seemed to sense this and let her off.

She was pleased when the fourth man wrapped his arms around her body and squeezed her tits for the umpteenth time that night. Remembering he was there, Anna swung around but only so that she was at a right angle to both men. With a hand around each cock, the lawyer stroked them at the same time while her mouth pinballed between them both, taking some time before shifting to the next.

“Oh she is good,” one of the men said to Sam.

“Shit…” Anna swore.

Her curse was in direct response to one of the free men behind her coming closer until his hands could yank down her panties to the level of her pants. With those out of the way, the man took two fingers and inserted them straight away into Anna’s pussy which had no trouble taking them given how wet she was.

“Tight too,” the third man said as he fingered her.

Anna continued to take turns bobbing on two cocks as another man fucked her wet pussy with two fingers, though he was working in a third. She adapted and took it inside her without issue while she placed the two cocks within an inch of each other’s tip so that she could lash at their pee slits with her tongue at the exact same time.

“I think it’s time for me to lose the rest of my clothes,” Anna said.

The men listened to her hastily. To remove her panties and thong, which is all that remained on her body, the two men who were getting sucked off hooked a hand into her armpits and lifted her up. Anna got her feet under her and immediately felt hands wanking down her clothes, presumably the man who was fingering her since her pussy was no longer getting stretched.

“Come sit friends,” Sam’s voice echoed in the large room.

Though they were happy enough with the current arrangement, her date clearly was thinking ahead. To Anna’s left was a row of four chairs set up with Sam already seated on the closest one. Each of the cushioned chairs next to him were soon occupied with the three men who she was now able to get a look at now that the moon was shining in through the large windows.

The one beside Sam was named Leo and was the smallest in height of the group but stocky with a cock that reflected his body shape identically. Third in line was Ron, who happened to be the sole minority represented, his flawless ebony skin shining bright in the moonlight with his massive cock standing proudly in front of him. Lastly was Henry, probably the most handsome of the men complete with olive skin, dark beard and tall but thin dick.

“So much cock,” Anna said, practically drooling.

It was tough for Anna to explain why she wanted to be used in group sex ever since her last encounter, and that was only two men at the same time. There was just something so dirty and sexy about it, it felt so hot to be fucked by multiple men at the same time and she was desperate for it. It would be overwhelming with so many hands and dicks around, but there wouldn’t be time to think, only do.

Though it was dark Anna was able to see Sam stand up from his seat and walk over to her. The pair kissed with his hands snaking around to fondle her small yet plump ass with strong hands. While they made out he walked backwards until he was reclining back in his seat, manipulating Anna so that she ended up on his lap straddling him.

“Now you ride,” he ordered.

Anna had no problem following that demand as she placed his head in her folds and sank all the way onto his lap. She moaned loudly as her twat was stuffed with his manhood, all 8 inches of hard cock. She grinded her hips with him held deep in her before rising up on her knees so only the tip remained. She repeated this treatment several times, rising his entire length for over a minute before he pushed her backwards slowly and back to her feet.

“I guess you’re next,” Anna said to no one in particular.

Stepping a foot to her left and spread her legs to walk between Leo’s legs until she could sit on his cock. As he slid in, she was stretched out further and moaned in response to this. He may have only been less than average length but he more than made up for it with a cock so wide it bordered on unrealistic. The lawyer wasn’t a size queen anyway so she could have cared less that he wasn’t wielding a long cock so long as he knew how to use what he had…and Leo could definitely do that.

Anna came for the first time while riding his cock as a matter of fact, using her impressive octave range to ring out her screams throughout the clubhouse. Leo didn’t get off, though he use her for his allotted time just like Sam had done previous, making her bounce on his manhood even while she came.

“Pass her here,” the next man up said.

Anna gave the men credit for not fighting over her, which would have been so easy. As Leo helped her get to her feet only for Ron to take her around the hips, lift her up and place her right back down on her third cock in 10 minutes. She thought about the trust and friendship that would have gone into having a gangbang with each other, knowing that there was only one girl and that they would have to wait patiently 75% of the time.

The sexy lawyer banished those thoughts from her mind as she began bouncing up and down Ronald’s impossibly long tool. He was her first black man to have sex with and her only regret was not having a camcorder so she could watch back the action. The whole time she rode him, his long ebony cock filling her pink pussy, she wondered how amazing it would look to be able to witness the act though she was happy with her current role.

“Henry’s turn,” Sam ordered.

Anna felt the tight grip around her slender hips drop in intensity so she used that chance to get her feet under her and push up until his cock left her hole and thudded against his 6-pack stomach with a wet slap. Her cum from earlier made his cock shine in the bright moonlight and she was overcome to bend down and lick up and down all four sides. Licking her lips after, she was happy with the choice she made given how tasty she found her own juices.

“Last but not least I imagine,” Anna commented to the remaining man.

Henry was tall and lanky and his cock was again a perfect reflection of his body size. As she took him into her, he gripped her neck and brought her down for a kiss. His thick beard tickled her beautiful face but she liked his forcefulness which was still tender enough to not be painful.

However, Anna felt like the man with olive skin was being cheated. Only a few minutes went by until she heard a man get to his feet and a quick look over her shoulder informed her it was the ringleader Sam. As if on cue, Henry pushed her gently backwards from her hips until she was no longer riding his cock, instead she was standing.

“Come,” Sam said.

Anna didn’t have to move towards him as he only had to spin her around so that he could kiss her deeply. She returned the kiss in kind, loads of tongue mingling like was becoming their trademark but then she became surprised when he started moving her backwards. There wasn’t much room behind her so within another step she was falling controllably back onto Henry’s lap this time facing away from the handsome man.

“Last with your pussy…first with your ass,” he said into her ear.

In the time she was standing and kissing the other man, Henry had reclined more in his seat which allowed Anna to have her back pressed against his chest in a more supine position. Unlike when riding them earlier, this time her legs dangled uselessly off his thighs which would make it hard for her to generate much power to ride up his shaft.

“He’ll be gentle,” Sam told her.

Anna trusted them for some reason and kept eye contact with her date while Henry from beneath her lined his cock up with her ass. They kept gazing at each other with pure lust as the olive-skinned man pulled her skinny frame down towards him and impaled Anna’s asshole on his cock.

“Shit,” she swore once and once only.

With each time she had anal sex, the initial penetration became easier and less painful. It was really the only point during the encounter that still stung provided the guy wasn’t a complete idiot and went too hard too fast. This time the sting went away within a moment, likely aided by how wet her cunt was and that Henry wasn’t the thickest cock in the world.

Still, it had been nearly half a year since her last in her dirt road so she was extremely tight which made Henry take his time. They did have all night but before long Anna found herself amazed to feel her small but plump ass resting on his lap having took all 10 inches inside her asshole.

“You’re something special,” Henry cooed in her ear while thrusting up into her bowels.

The surprises kept coming for the horny lawyer. With anal sex becoming comfortable, Anna expected to be lifted off his lap and passed along to the next guy in line, but Sam had something else planned. She expected for her to lift her up when he bent down towards her, but his hand went to his cock to steady his aim as he kept moving closer until his tip was rummaging through her lips until pushing into her hole.

“Mhmm…yess,” Anna practically screamed.

Anna began to really moan in ecstasy now as Sam started to fuck her hard after an initial period of letting the auburn-haired girl get use to the sensation of being fucked in both holes at once. It would have surprised them but this was not Anna’s maiden voyage with double penetration and given how good it was feeling it would not be her last either.

Anna wasn’t the only member of the threesome enjoying themselves as both males were issuing primal grunts as well. Henry wasn’t able to generate as much power as the other man but he still jabbed his cock upwards into the lawyer’s ass, making her large tits jiggle each time. Sam had wrapped a hand in her shiny hair and pulled her head towards him as he continued his non-stop assault in and out of her pussy.

“Damn…asshole is amazing,” Henry grunted from below.

Anna felt sad when Sam pulled out of her wet snatch, albeit after a few last hard thrusts. The friction between their two cocks on the thin membrane separating them was sending her through the roof with pleasure and she was disappointed to have the feeling go away.

After Sam was done pumping into her, he pulled out and stepped back, not without giving her bouncing tits a hearty squeeze. With his body no longer there, Henry sighed and lifted her off him as well, upset to have the tight confines of her sphincter no longer milking his dick.

Anna use to be worried after having anal sex that their dicks would look dirty since they had been in her poop chute but not anymore. Before leaving work she had used the shower, lathering up her entire body including a finger which she had stuck straight up her bum. It was the first time in her life that she fingered her own ass and it gave her a perverse thrill, which was why she left it in there for minutes until finally leaving the jetting water.

“Over here baby,” the black man beside her beaconed.

Both her holes were already free of cock so Anna was able to walk the short distance to Ron, who took control from there. When she was within arm’s reach the black man spun her around so she faced him then had her climb aboard. His long dark cock easily fit back into her wet twat without problem and her instincts took over as she bounced on his length.

Less than a minute passed before she felt a hand on her back between her shoulders blades pushing her gently down. She gave in without trouble and soon found her large swaying tits pressed against the flawless dark skin of Ron, who now had to push his hips upwards to compensate for her lack of riding in her new position.

This time Anna knew what was coming it would only be a surprise of which man it is who would take up the free position of her ass. She didn’t even need to turn her head backwards to look once she felt the sheer width of the cock placed at her anal entrance. She knew it would likely come to pass that the thickest of them, Leo, would have a chance in her ass and it was now.

“Oh my God that’s a huge fucking cock,” Anna swore.

Leo knew enough to start slow despite the fact her sphincter had been fucked and loosened by his friend already. However he did short slow thrusts to get the skinny used to not only being fucked by two guys at once, but by the massive girth of his dick. As he slowly fucked her and waited for her to relax more, he spanked her small but curvy ass, making her cheeks red.

“Such a small little asshole,” Leo commented.

“Well it used to be until you got in there,” another added.

With her asshole now loosened up, Leo started to fuck the much smaller woman with more urgency. She moaned more, at times not always out of pleasure but there was no sharp cries of pain from her, something that Leo was more used to hearing. Continuing to test her limits he stroked in with greater depth and more speed but Anna seemed up to the task each time.

Anna knew that these men had no feelings for her so far as that she was a hot chick that they could fuck. Use her, abuse her as much as she could take and treat her just as a series of holes for them to slot into and get off. But she was okay with that right now. In fact she was getting off on that knowledge too. That she was just some filthy whore who was getting exactly what she wanted, what she was craving.

At this point Anna lost track of time and even how many times she had cum. She knew she had at least one more orgasm and that was while she was double penetrated, but it could have been more. She vaguely remembered being passed around from man to man until each and every one of them got to sample both her holes. But now she was snapped out of her fog as the men neared their end. And their finales were all started with another of Anna’s orgasms.

“OH GOD…YEESSS,” Anna screamed loudly as her lithe body was rocked with another climax.

Anna cumming started a chain reaction for the two men who had their cocks pumping in rhythm as they both pummeled into each of her once-tight holes. Henry and Ron had been fucking the tired girl for the past quarter-hour, and it was finally catching up with them. As she came, her asshole and pussy reflexively clamped down even harder around their dicks, trying desperately to milk them of their jizz. Both men gave in and groaned in delight as two loads of hot jizz rocketed from the tips of their penis deep into her bowels and womb.

The two men slumped their heads in pure exhaustion as their nearly two-hour long fuck session was finally over. Ron was the first to pull out of the equally tired woman, removing his cock from her asshole which gaped open the entire time he walked over to his chair and slumped into it. This left Henry to lift up the thin girl from his tool, using the last of his energy reserves and spilling the cum-filled girl onto her side into the wooden chairs beside him.

“Shotgun,” Leo called out, instantly appearing in front of her. “Though I won’t be using either of those holes.”

The athletic male didn’t hesitate at all and slammed his entire short but thick cock into Anna’s mouth in one shot. Her throat was already loose and he knew she could handle it, which she did despite her exhaustion. She steadied her head and allowed the wide-set man to pump her face with his cock. All while thrusting into her mouth, Leo couldn’t help but look down on the side lying redhead, her nakedness allowing him to watch her pillowy tits jiggle while further down cum leaked out of both her pussy and massively gaped asshole.

The man, as physically fit and sexually experienced as he was, still needed to cum urgently after pumping her for only a few more minutes. Before he started to cum he stopped pumping into her throat, instead placing the head of his spit-covered cock between the ginger woman’s plump lips. Torrents of cum erupted from his, plastering the back of her throat and surface of her tongue. Even in her tired state, the red-haired beauty swallowed down his offering of salty seed, even giving him some post-coital head on top of it.

“Fuck that was amazing,” the stocky man huffed.

“And then there was one,” Sam said, cock still erect as he looked at her near naked form.

The one she was referring to was currently the only man still left standing upright; the burly Sam, her original date for the evening. However, much like his friends, the thuggish man wouldn’t last much longer. The night long fuck session of pounding each and every one of Anna Kendrick’s tight holes had ebbed too greatly at his endurance.

Looking down at the ginger beauty, cum leaking out of her well-used asshole and pussy while another load of jizz glossing her lips, Sam decided on his plan of action. She seemed to be on the same train of thought as she swung off the chairs and landed softly on her knees beneath him.

“Gonna fuck your big tits,” he hissed.

Anna was already grabbing the outsides of her large globes which were a natural wonder especially given her slender build. Sam placed his slick rod on her breastbone right before Anna pushed her boobs together and engulfed his member. The pair worked as a team with Sam thrusting into her body while Anna maintain pressure and rocked up and down as well.

“Fuck me big boy,” the lawyer murmured though clearly exhausted.

“I’m gonna cum soon,” Sam warned through gritted teeth after only a few minutes.

“Cum for me baby,” Anna told him, her fingers reaching down to caress his full balls. “Paint my tits.”

Her slut words combned with her hand playing with his nuts and the tight seal of her tits around his cock finally added up. With one last good thrust deep inside Anna’s cleavage, Sam finally let go and allowed himself to finally cum.

Anna watched as he pulled away from her great set of breasts and stroked his cock all while pointing at her chest. It took no more than 5 seconds before the beat his load onto her tits with the first stream of white goo landing on her left breast. The remainder of his jizz splattered mostly in her cleavage or on the inner curve of either boob, a healthy amount of cum now decorating the majority of her boobs.

“Ugghhhhhhh,” Roy grunted as he emptied his load onto her flesh.

“Holy shit,” was all the exhausted girl could muster.

The rest of the evening was a blur, though this time from exhaustion. She remembered as they all gathered their clothes and showed Anna to the washroom to freshen up. Returning fully clothed, she found the men had done the same before Sam led her out of the clubhouse where the same limo waited for her. This time she gave the driver her home address rather than her work one and was sleeping soundly in her own bed in less than half an hour.

*           *           *

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