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Anna Kendrick: Winning at all Costs	By : TheChemist Category: Celebrities - Misc > Threesomes/Moresomes Views: 14015 -:- Recommendations : 0 -:- Currently Reading : 1
Disclaimer: This is an act of fiction. I do not know Anna Kendrick, Hailee Steinfeld, Emily Blunt or John Krasinski at all and this scenario did not actually occur. I make no money from this story.

Chapter List
- 1
- 2
“Okay Ms. Kendrick, your rehearsal time is done,” the stage manager called out.
“Really? 3 hours went by really quick,” the upbeat and quirky Anna Kendrick replied. “No problem.”
After thanking all the dancers and her choreographer, Anna grabbed a sweat towel and left the stage. She was just finishing patting down her face when she dumped into her opponent for the lip sync battle, John.
“I’m so sorry,” Anna apologized without knowing who it was yet.
“Watch where you are going, short stuff,” he replied with levity yet a touch of cruelty.
“Didn’t see you John, my mistake,” she replied, all of a sudden withdrawing.
“That’s fine. I’m in too good of a mood. After seeing what ‘challenge’ you’ll provide me with, this will be even easier than I originally thought,” he mocked. “Just don’t forget our arrangement. And trust me, it won’t be as kind and gentle as last time.”
Anna stood in the hallway with her mouth gaping open after that exchange. For one, she thought her dance routine and song choice to be a perfect mix of entertaining and crowd pleasing. And for two, the fact that he thought their last sexual encounter was either kind or gentle.
It had happened only a month ago after the movie that John was directing her in had wrapped. Anna was drunk and horny and John was all too willing. It ended up being the longest and worst sex of her lift, her spending most of the evening bent over in a guillotine as the lanky man fucked her in all her holes, whipped and paddled her ass then had the balls to actually pee on her face.
“Ms. Kendrick, I’m going to need you on the other side of the door. These rehearsal times are suppose to be private,” a member from the show told her.
Snapping out of her thought she retreated to her change room as a cold wave of dread rolled over her. She didn’t technically make any bet with John, however, he simply stated that if he beat her, then she would spend the night with him again. She didn’t have a choice, he was a powerful man in the industry now, and though she was a common name, women tended to have very short shelf-lives in Hollywood and that was if you didn’t piss anyone off.
More resolved then ever, Anna couldn’t lose. She loved her first choice of song, and though it would have been better to actually get John’s wife to appear on-stage, her back-up plan was fairly clever. But John was right, her second song, the one meant to win it for her, wasn’t perfect. She needed help and she had an idea of where to go.
“Sid, can you come here,” Anna said after hunting down the sound controller.
“Oh Phil, there you are. Meet me in my dressing room in 5 please,” she told the choreographer.
“Just the man I was looking for, Carl,” Anna greeted her assistant while appearing on the show. “Follow me.”
With the three people she needed to find accounted for and in her dressing room, she blared some music to drown out their conversation from lurking ears. She laid out her plan and what she needed from each of the men, and also what they stood to gain from helping her win tonight.
“Wait. So if we do this…”
“Then I’m all yours. You have the evening with me. You can play rock-paper-scissors to see who wins me, or all come and take turns, whatever. But giving it up to three nice guys is wayyyyyyy better than one night with John again,” Anna explained, shuttering at that last point.
* * *
“Okay Kendrick. Bring it home now,” Anna said to herself, pumping up her energy.
Her first song had gone amazing, using all her feminine charm and girl-next-door attitude to mesmerize the crowd. However, the big problem was that John busted out some super funky, but hilarious dance moves that surely gave him the first round victory. Then, he upped the ante by doing a little cross-dressing, which once again played very well with the fans.
“Just remember, be bouncy,” Phil the choreographer reminded her, his eyes darting down to her big tits.
“And don’t worry, your surprise is ready to go,” Carl added.
Anna thanked them then heard her name being called. With one last big breath, the adorable, pint-sized actress headed onto the stage as her song choice blurred. As dreamt up by the dance coach, her song had lots of bouncing, which made her large breasts jiggle, especially in her low-cut and under-supported top.
As the song continued, every man in the audience would surely scream at the top of their lungs in her support come vote time. There were a few times Anna didn’t know how her C-cup boobs, made to look even larger on her super-petite frame, didn’t come flying out of her top.
“Holy crap! That’s JLo,” John said from his seat on-stage.
Phil may have selected the song choice, but it was Carl who came through and secured on of the biggest movie stars on the planet to join Anna on stage. Though Jennifer was only there for a few moments, the fact Anna sang her song about big booties, and the women that helped launch the big booty craze for the past decade was there, would surely guarantee her victory.
“Did you like that,” Anna said to John during commercial break.
“Cheap stunt, Tits Magee,” John replied, teasing her with the nickname he knew she hated. “I hope you don’t mind those puppies getting pinched by my alligator clamps later tonight.”
“Okay everybody, you know how this works. You cheer for the artist who you believe should win,” the host announced. “Okay, let’s give it up for John.”
A roar of applause sounded, making Anna instantly nervous while John’s cocky smile grew ever louder. She had to admit that his performances were amazing, but she was hoping and praying to any god that would listen that she would win. The thought of that sadist ruining her body even worse than last time gave her the cold sweats.
“Alright, alright. And if you want Anna to win then scream,” the host told the crowd.
The cheer was initially less than it had been for John, and Anna felt her stomach drop. She was going to be his sex slave again for the night. However, just as John was turning to accept the wrestling-esque belt the show had created, a wave of cheers erupted. The sound was deafening, clearly louder than what John had received but something sounded weird about it.
“And the late rally of the fans does it. Your winner this week is…Anna Kendrick!”
* * *
“Oh my God! You guys, all of you, really came through,” Anna told her guests.
After the announcement and the belt was cinched around her waist, John called her a cunt under his breath then stormed away. She shook hands and thanked her people before heading back to her assigned dressing room where her three helpers were waiting, just like she instructed them.
“No problem, John seemed like a dick anyway,” the dancer teacher said.
“Thanks for the routine at the last minute and hooking me up with those awesome dancers,” Anna thanked before turning to Carl. “And how did you get J-Lo on such short notice?”
“I knew she was in town and she owed me a favor,” the half-Swedish man replied.
“Well I appreciate you calling it in for me,” she said with heartfelt sincerity. “And you came to my rescue in the 11th hour Sid.”
Sid blushed and waved her thanks, glad to help out the pint-sized beauty. He had almost blown it, after all he had mis-synced the timing of the fake crowd applause. However, he had corrected the issue in time and the artificial cheers counted, letting Anna escape John’s sexual wrath.
“Okay, so like I said, I’ll be at this address tonight. Whoever is there, I’m all yours,” Anna said.
* * *
“Thank you,” Anna Kendrick said to the taxi driver as she paid him. “And like we agreed, be here in 3 hours again.”
Once the driver agreed, Anna stepped out of the car and looked at the rented house. After securing her win, she went online and booked the house for the evening, paying a fairly cheap rate for such a nice home as well. Wanting to look good for whoever was on the other side of the door, Anna wore a low-cut colorful blouse that displayed a good deal of cleavage, as well as a simple black skirt that was short enough to almost expose the bottom of her ass.
Approaching the door, a sign on the front of it said come in. The handle turned and she pushed open the large wooden door, stepping into the foray. As she entered, she turned right and walked into the large living room to find the trio all there, waiting for her. Sid, the most muscular of the three, Phil, the tall dark and handsome one, as well as Carl, who could have been a Swedish model.
“Well now it’s a party,” Anna said, her lip sync champion belt draped over her shoulder and across her body like a beauty pageant sash.
“We talked, and after coming to no conclusion on how to share you, we decided…”
“…to have me all at once,” Anna said, actually finding her twat getting wet.
“You’re okay with that,” Phil asked, almost in disbelief.
“It’s a tall order, but three boys and me at once sounds kinda erotic,” the movie star replied.
What surprised a lot of people once they got to know the innocent looking actress was that Anna Kendrick had a rather large sex drive, and a very open mind. The act of these three men risking their jobs in the industry they clearly wanted to be in all to help her was as big of a turn-on for the pint-sized auburn-haired girl as they came as well.
“Now how about less talk and more sex,” Anna stated.
Like sprinters reacting to the starting shot of their race, the three men descended on the much shorter girl. Sid got to her from behind first while his two fellow friends flanked Anna. The first thing that needed to go was her massive belt from winning the game.
By the time the sound controller put it on the table behind him, Anna’s colorful blouse had been pulled open. The actress knew what would be in store for tonight so didn’t bother with a bra, allowing the two other men to each start sucking on her large tits.
“God, these are massive,” Karl said in between licking her tit from underside to the top.
“So perfect,” Phil agreed before sucking on her adorable little nipple.
Seeing that she was pretty occupied by his friends, Sid went about removing the rest of her clothes. After peeling her shirt off her thin shoulders, the bulky man crouched down and his fingers darted to the zipper on the side of her skirt, undoing it. With no resistance holding it to her narrow waist, the garment descended down to the ground, crumpling around her feet leaving the actress completely nude.
The two men sucking her large tits must have sensed her nudity as they pulled back in order to drink in the sight. They were greeted to a unobstructed view of her nice ass, which may have been slender but had a great deal of thickness. Her pussy was the way that they all liked as well, shaven bare so that her bright pink lips could be seen between her thigh gap.
“Oh dear, it appears I lost my clothes,” Anna said with mock embarrassment.
Once again there hands were all over her, and Anna didn’t mind at all. One of them brought her in for a sloppy and aggressive kiss, which she was more than happy to match. Sid took his chance to reach from behind her and knead her awesome rack, the soft flesh squishing around his hands. Meanwhile, Karl the Swede used his right hand to grope her tight backside and his left hand to rub her snatch, which was already gushing wet.
“Nice tight ass too,” the Swede commented.
“Have we mentioned the flawless rack as well,” Sid commented, still not comprehending how the actress could have such perfect tits.
“You guys are so sweet,” Anna said, breaking away from the lip lock. “But tonight is for you. So let me show you how thankful I am.”
With all eyes on the naked 28-year old actress, Anna slowly and seductively lowered herself to the ground, coming to rest on her knees. It was a very common position for the auburn-haired girl to find herself in, either it be on carpet, grass or for an audition. By the time she was down, the three men had all kicked away their pants, cocks out and ready.
Anna adored Phil’s dark chocolate skin already and was impressed with his athletic physique but her eyes bulged at the sight of his 8-inch cock. After staring for a few seconds she looked next to her right, seeing the Swede, Karl, who had a taller frame with surprising definition though she wouldn’t call him muscular, however he rocked a longer cock than Phil albeit slightly skinner. Last she looked at Sid who had the smallest but fattest dick of the trio, a healthy 7 inches but with amazing girth.
“See something…or somethings you like,” one of them asked with supreme confidence.
Anna nodded her pretty head while her beautiful eyes remained fixed on their impressive packages. The Pitch Perfect star didn’t want to keep the excited boys waiting any longer. With a final lick of her lips she opened her mouth wide, leaned forward and engulfed the tip of the closest cock in her mouth. She bobbed her head a few times,apparently on Karl’s lengthy dick, working just about half his good-sized tool into her oral cavity then pulled off him altogether.
“Oh man that’s good,” the blonde groaned.
“Just the tip of the iceberg pal,” the auburn-haired beauty told him.
Anna pivoted slightly so that she was now facing the muscular Sid and repeated the same trick on him. After sucking on his lengthy pole for a minute she pulled away from him and turned nearly 180 degrees to face the remaining man, Phil. Again she opened her mouth and pushed her lips around her third cock in as many minutes, getting half his length wet with her spit.
“You’ve certainly got talent,” the choreographer commended.
“Please,” Anna said. “You haven’t seen anything yet boys.”
With the boys paying attention to her every sexy move, the girl with the big tits did a long lick over her thumb and forefinger on each hand. With their cocks now lubricated as well as her hands, Anna gripped the two dicks on the outside and began stroking them at a solid pace. This left her face to focus on the meat right in front of her, belong to the Swede, which she gladly gobbled up with her mouth.
The boys to their credit showed intelligence and the ability to share which wasn’t always easy when the hottest girl that they had ever met was blowing you as well as she was. Every minute or two Anna would pull her plump lips from one dick, only to pivot to her left and swallow the next one. The men were now shifting along with her so that she was continuously stimulating the trio.
“Yes Anna! Suck my dick,” Sid encouraged the Oscar nominee.
Phil had stepped good and close to the naked girl and was prepared to take advantage of her insanely magnificent tits. He had been following the actress’ career for close to a decade and had watched her develop into the smoking hot nerdy girl in front of him, nerdy girl with large boobs. Now, as he placed a hand on the outside of each of them, he pushed them together to form a tight pillowy hold around his cock.
“You smart bastard,” Karl observed, his own shaft being stroked by Anna’s hand. “Nice.”
“I know, right,” Phil practically shouted with excitement.
Sid was jealous of the dark-skinned man for being the first one to take advantage of her pillowy tits and thrusting his pole between them, but he knew it would be his turn sooner rather than later. While Anna was busy bobbing away on the other man’s cock with her tits preoccupied with Phil’s eager cock, the sound controller looked down to survey the action and smile with pure delight.
The muscular man let his friend and co-worker have a little bit more fun titty-fucking the attractive actress, but after another minute he sprang to action. Putting his hands under her arms, Sid lifted the girl who couldn’t have weighed more than 100 lbs and walked further into the living room until settling her down on her back atop the knee-high ottoman.
“Whoa! Thanks for the ride,” Anna giggled, flashing her mesmerizing smile.
Acting quickly before anyone else got any ideas, Sid was between her spread legs and looking down over her slender yet curvy body. Without bothering with a condom, the sound technician grabbed his thick cock, dragged his tip through her pink slit and spread his pre-cum before lining up with her wet hole.
Without further delay Sid had placed his tip against her wet hole and pushed his hips forward. He was the thickest of men, and though she was tight his meat still slid into her, though not as easy as most would have. It helped with her being as wet as she was, but he could only get halfway inside her the first time. Stopping and pulling out most of the way, he pushed in this time with more success. After a few pumps, his entire 7-inches of cock was gliding in and out of her slick folds.
“Oh yes,” Anna squealed in pleasure as he eased his whole length into her.
“Holy fuck! You’re so tight,” Sid groaned.
With his hands clutching tightly onto her slender hips while the other two men got onto either side of her, the bulky man continuously reared his hips back before shoving them forward. The result forced Anna to be rocked about on the large ottoman, her heavy tits heaving forward and back to everyone’s delight.
“Feel like multi-tasking,” Karl the Swede said from beside the gorgeous girl.
Anna laughed and nodded her head before instantly opened her mouth wide to allow him back into her experienced mouth. The adorable yet sexy actress gave him a few strokes of lengthy tool and noted how smooth he was. She took a moment to time the rhythm of Sid fucking her with her own hand massaging his cock before starting to blow him. She parted her plush red lips and brushed her long hair behind her ears then took him into her mouth and started sucking him off while her slender body was heaved back and forth.
Despite the rough ride that Sid was inflicting on her, Anna began building momentum as she bobbed her sideway head on the man’s thick pole, taking more of him inside her each time. With every one of Sid’s thrusts inside her rubbing her sensitive G-spot, the Pitch Perfect star would moan around the Swede’s cock to add extra pleasure to the horny man.
“Remember to share,” Anna said to the blonde man as she rotated her head to the other side where the third man was waiting for her.
“Move your hands out of the way,” Phil told the younger beauty.
Anna did as the black man asked, using her hands instead to stroke the blonde man’s cock, still wet in her spit, as well as rub her own clit. Without her hands obstructing his way now, Phil was able to really saw into her mouth with the speed and depth that he dictated, not the pretty girl anymore.
This time she was forced to take him inside her oral cavity once again and had him butt up against the back of her mouth, not that she minded at all. With the cock still plowing into her dripping wet pussy, not to mention her mindset in allowing them to make her their perfect slut, Anna was literally down for anything.
“I hear talented singers like her have complete control over their vocal cords…and throat,” Sid commented, his body already sweaty from the frantic fucking.
With that idea in mind, this time when Phil pushed back into her mouth with her face having over the edge of the couch. Anna knew what he intended so relaxed her throat in an action that was second nature to her. It took an extra moment but her muscles relented and she pushed forward so that now her chin was buried in his thick bush of pubic hair and her nose pressed against his full ball sack.
“Oh shit Anna…you have skills,” he proclaimed complimented, his cock still completely contained within her mouth and throat.
The girl with big tits had no room to move her head back and was utterly at this stranger’s mercy. He held his cock in her mouth for a few seconds, at which point he could see her face flush red. At that point he withdrew all the way and watched as the talented singer/actress coughed and spat large amounts of spit onto his cock, her own gorgeous face and onto the floor of the rented house.
However, rather than being upset at him for choking her with his mighty cock, she opened her mouth to take him once more into her mouth as opposed to curse at the asshole. Of course Phil didn’t delay for a millisecond as he pushed his hips forward until his cock slammed back down her throat. He watched as her eyes nearly bulged out of her face as her gag reflex was narrowly avoided being tripped, small tears forming and rolling over her model-esque cheekbones out of reflex.
“Gllugghh…uugghhh…awwkkk,” Anna muttered and gagged as the older man repeated pushed in and out of her throat.
With three guys in the room and only one girl, Sid understood that his time between Anna Kendrick’s slender thighs would be limited. It may have been his first mini-gangbang but he knew they needed to share. Knowing he had to get the most bang for his buck then he’d have a period of rest, Sid held nothing back. Over and over he pumped the willing girl with his tool, looking down and watching as her large boobs continued quaking under the contact with his pelvis.
Of course, a few minutes after the bulky man came to the realization that it was better to go all out when his co-workers asked to switch with him. Even though they were taking turns getting sucked off by a talented girl, they had been waiting patiently and wanted their turn now too. He gave a few last deep thrusts into Anna’s pinkness then pulled his juice-covered cock from her.
“Here, wanna see how you taste,” Sid asked the girl.
As she stretched her arms out to him, Sid clutched her skinny forearms and hauled her towards him. Anna stayed slumped down, wrapping her arms around his legs to hold herself in position and get her lips around his dick. She wasn’t able to deepthroat him in this limited position, but she was able to suck her juices off the first half of his cock and conform that she was as sweet-flavored as ever.
“Yum,” Anna said, smiling up at him. “I have tasted a lot of twat in my life and mine still ranks as one of my favorites.”
Karl had been extremely patient, but between watching as one co-worker shagged Anna senseless while the other face-fucked her, it was ebbing away. Seeing as Sid had just finished between her legs, the handsome Swede reacted quickly. Taking up the vacant position in the instant became available, the blonde wasted no time in slamming his lengthy tool into her inviting twat.
“You weren’t kidding about how tight she was,” he groaned, giving the busty girl a few hard thrusts.
Not overly comfortable in the position on the ottoman, Karl waited for Anna to be switching between dicks in her mouth to act. Wrapping his arms around her back, the blonde man hoisted the Pitch Perfect star easily off the furniture and turned towards the stairs. His initial idea was to walk her all the way upstairs, but he didn’t get that far before the urge to fuck her took over. Instead, he stopped at the first flat piece of wall, planted her back against it then repeatedly jackhammered into her wet cunt.
“Oh yes…hitting…all the right…spots,” Anna panted.
The talented actress had no problem being used essentially as a fuck doll for the three men, in fact she appeared to be getting off on the degradation. Karl didn’t care about what issues she must have had for that to be arousing for her, instead he thanked his lucky stars for the opportunity, even if he had to share her.
It helped that she weighed barely anything and that the wall was supporting some weight as well, but the constant squatting so that his cock was as low as he could get it before plunging upwards was tiring. She held tightly onto the back of his neck with her perfect tits bouncing against his chest as Karl clutched her tiny ass, which he found so unbelievably sexy.
“Come on, let’s take her upstairs,” one of his co-workers suggested.
“Oh…right,” the good looking man replied.
Karl had gotten lost in his own pleasure that he forgot that the other two men were essentially just standing around, stroking themselves as he fucked Anna Kendrick solo. With sweat covering his face, the Swede got a better hold of her and started up the stairs, now feeling the tiredness in them. It didn’t help that there was 12 steps, so he decided on a new plan.
As he neared the landing, the blonde man turned back around then sat down on the top step, his cock still buried in her cunt. It didn’t last long as Phil, the only guy yet to fuck the actress, acted swiftly. Pulling back on her narrow hips, Karl’s cock spilled out from her cunt as he gently settled her two steps down from the sitting Swede.
“Couldn’t wait, on the stairs will be good,” the black man commented.
Anna somehow was unfazed by the positional changes, as she was already cramming Karl’s cock back into her mouth. She had bibbed several times on his length, getting to taste her preferred pussy juices on his rod before the third man was ready for her.
Crotching behind her, Phil grabbed his 8-inch member and thick as a wrist to stroke it a few times, still slick in Anna’s spit. He didn’t bother with a condom like the other two men hadn’t, he placed his bulbous tip against the opening to her snatch and pushed forward. Given how wet she was, his dick slid into her until half his shaft was drenched in her juices, a smile spreading over his face despite the dick halfway down her throat.
“Mhmm…feels so good,” Anna cooed as she was fucked by a third man in 15 minutes.
Luckily for Sid, the staircase was a lot wider than most homes had. Sidestepping the trio as they spit-roasted the attractive movie star, he walked right beside the action, waiting his turn on the step between where his co-workers occupied. Anna had enough wits about her still to notice him there, so after pulling back so her nose and chin were no longer buried in Karl’s lap, she twisted towards him.
“Was hoping you didn’t forget about me,” the muscular man commented.
To show that she didn’t, Anna gripped him around the base then quickly twisted her head back and forth as her mouth closed around the side of his cock. Having Anna Kendrick rub her lips all over his shaft made him shudder in pleasure, but she had more in store for him.
All while taking a thick cock repeatedly into her cunt from behind, she tilted Sid’s cock higher up so that his balls actually rested in the middle of her face on top of her nose, which made the younger girl giggle. In a second she had her mouth open, head repositioned and was sucking with delight on the slightly sweaty sack.
“Mmmmm…awwhhhhh…mmhhmmmm,” Anna moaned around his balls as the man behind her thumped into her with renewed vigor.
Being able to fuck her doggystyle allowed the black man to go both fast and deep, something he took full advantage of. Even as she teabagged his friend, Phil routinely bottoming his thick cock all the way into her pink hole. Wrapped up in the occasion, the horny dance instructor brought his hand to about shoulder height then let it come whipping down, smacking her bare milk-colored cheek. The slap resonated loudly around the enclosed staircase, even drawing a murmur of surprise from the unexpected girl.
For the sake of evenness, Phil did the same thing with his left hand to her other cheek, giving her a match set of red handprints on her small yet plump ass. Satisfied with his handiwork, no pun intended, the dark-skinned man slapped both cheeks at the same time and held them there, squeezing her tight backside while he fucked her pussy raw.
“Fuck me, fuck me, fuck me,” Anna squealed with encouraged, her mouth free for the first time in a number of minutes.
“You heard her boss, give her what she wants,” Karl encouraged as Anna’s lips closed back around his hard cock.
Phil continued giving the horny girl what she wanted and really started to stroke into her tight twat. Even with how thick he was and the tightness of her pussy, she was loosened up by three rounds of different sized cocks and still so very wet that he could hold nothing back as he plowed into her. Anna’s velvety walls hugged him so constricting that he needed a break immediately from pounding her into oblivion or else his night was going to come to a sudden end.
“Need a break,” he said while pulling out. “She’s so fit.”
“Help me get her to the bedroom,” Sid asked of his friend.
With each of her arms looping around their necks, Sid and Phil had no trouble hoisting the tiny actress from her knees and cradling her. Another 10 steps got them to the upper floor and a lucky guess had them carrying her through the threshold of the master bedroom before settling her down on the plush mattress.
However, it was Karl who positioned himself between Anna’s legs. On his way there though, the blonde stumbled but he played if off by casually dropping down to his knees, right in front of the girl’s sex. Realizing that her cunt had been filled by two other guys, he lifted her ass off the bed and used his tongue to lick her asshole instead.
“I guess that’s what they do in Sweden,” Phil said, sharing a laugh with his buddy.
Ignoring his coworkers jeers, Karl redoubled his efforts while they flanked Anna on either side of her head. While the gifted actress took turns sucking on their lengths, the Swede used his long fingers to pull apart her cheeks while using his tongue to spear against her spread sphincter. Anna moaned around the cock currently in her mouth as Karl licked as deep as his tongue could possibly reach inside her ass.
“It’s okay, you can do it,” she told the man as he stood after licking deep in her booty. “I’m not a prude, you can make me your anal princess.”
Karl had to stop his jaw from hitting the floor as he listened to the well-known celebrity’s request. Of course he was going to do it as long as he didn’t have a heart attack from pure excitement first.
“Give her what she wants bud,” the bulky man added as he clapped Karl on the shoulder.
With that said, nothing else had to be, so the Swede watched as Anna flashed him one more of her seductive smiles before turning around to show off her wonderfully petite ass. She gave him a little show by wiggling her bubble butt as she held her legs up by her chest invitingly.
As Anna felt his bulbous tip touch her asshole and maintain contact, she did her best to relax her orifice. She momentarily stopped sucking the two cocks by her face and hoped that the ample amount of spit and her pussy juices she coated his tool with would be enough lubrication for her.
She had a moment of panic by thinking why she would beg to take such a well hung cock in her tight rectum for her first time in months, but that was quickly forgotten. That was because his tip against her backdoor, Karl sustain the pressure gently yet firmly until just the head popped into the gorgeous actress.
“Ugh,” Anna groaned, the feeling similar to a bee sting. “Give me a minute.”
“Holy crap! Can’t believe this tiny chick is being sodomized,” Phil summarized.
“I know. Seeing a cock, even only the first inch, in Anna Kendrick’s asshole is the hottest thing I’ve ever seen,” Sid agreed.
Anna succeeded in relaxing herself then stayed like that as Karl, who clearly had fucked some asses in his past, made slow but smooth strokes into her bowels. Slowly she enveloped another few inches of his manhood as he repeated this course of action. He fucked her with his tool in her ass a few more times, now with over half his length before looking down her fit body at him and gave him a curt nod. The horny man took the hint that it was fine for him to start really fucking her.
Realizing that Anna was allowing him to take the training wheels off, Karl really started to stroke into the actress. Gripping tightly onto her hips, the Swede slowly moved the length of dick in and out of her asshole, being certain to not be too jerky or stab too wildly. Meanwhile, the two up by her head were happy once as Anna was now able to start stroking and bobbing on their cocks again.
“Oh…yes…mmm…awwwhhh,” Anna moaned in a tone that wasn’t tainted in pain.
“You like that? My cock in your ass,” Karl asked, picking up the pace slightly.
“Yeah…ahhhh…feeling good,” Anna told him, stroking the two cocks in her face.
The man fucking her ass was making a mistake though. Karl was getting faster and faster as he worked his whole cock in and out of her vice-like ass. It hugged him from all angles and seemed to be getting tighter around him then the opposite. However, his error was looking down and watching as he speared inside her bowels, seeing her pillowy tits bounce with each thud, listening as his balls tapped the underside of her cheeks.
Slamming his length back into her one final time, the Swede pulled himself out of her tight hole, paused slightly to watch as her gaping hole slowly sealed back tight and made her get on her knees in front of him. Anna knew exactly what he wanted so she opened her mouth in preparation with any hesitation. Sure enough, she felt his cock, which was pasted in her own juices, slap onto her tongue.
“Wow! She put it in her mouth,” Phil said in astonishment, watching the Pitch Perfect star blow the dick that was fresh from her own asshole.
“I don’t know why that is so hot…but it is,” Sid added.
Karl as well couldn’t believe that she was sucking the taste of her own asshole from his pole, but the act of degradation was really getting him off. The men would have been even more surprised to find that Anna was finding that she was actually missing the feeling of his dick filling up her rectum.
“That’s right, suck your own ass Anna,” the Swede cheered. “You’re such a good ass slut.”
At that moment Karl stopped caring about anything else happening as cum started to fill up Anna Kendrick’s mouth. She also stopped thinking about how tasty her own ass was, instead she did her best to collect all his seed without spilling any, which ended up being a tall task.
As soon as the actress felt the first stream of warm cum land on her tongue she formed a tight seal with her lips around his cock and proceeded to milk all of his warm seed. When she was sure he was done squirting his hot load into her mouth, Anna swallowing it down with another sexy smile plastered across her face.
“Oh my God,” the man cursed, slumping back into a conveniently placed reading chair.
“Glad you enjoyed yourself,” she told him, getting back to her feet.
“Oh God,” he shuddered again.
She wasn’t to be resting on her feet for very long though. Feeling hands on her lithe body again, Anna was lifted up once more that evening, this time by the strong arms of Sid. The man with the big cock didn’t have long to travel before he was laying both the talented actress and himself done on the comfortable bed.
“My turn,” Sid blurted out.
“Haha, totally right,” Anna said, swinging her face and tits back in their direction.
With the bulky man laying flat on his back, Anna climbed onto his lap. With slender legs on either side of his powerful waist, Anna reached between her thighs to grip his cock. Holding it straight, she pushed herself backwards until feeling his extremely thick manhood slice through her folds.
“Holy hell those are some fine tits,” Sid commented, as he reached out and squeezed one.
Anna smiled at the man she barely remembered the name of then got back to the task at hand, namely bouncing her petite body on his dick. Phil seized the chance to climb onto the bed with his cock right in front of the riding girl, and to her credit, the girl could multi-task as she took the black manhood into her mouth. As if she did it all the time, Anna sucked his tool at the sacrifice of her intense riding slowing down. She was still working his entire member into her velvety folds, but at a reduced pace, not that Sid had any reason to complain.
The slowing of her bouncing was actually a blessing for the muscular man. As Phil was currently experiencing, Anna was skilled with her mouth and her pussy was tight so it ebbed solidly at his restraint. As the auburn-haired beauty continued to systematically raise and fall on his tool, he noted that this own resistance was waning.
“So good,” he grunted as Anna sank onto his manhood.
“Great…mmmm…on my end too,” the actress agreed.
“That’s right…you’re gonna wanna get that dick nice and wet,” Phil told the bouncing girl.
“Why do I have a sinking suspicion that I know what you’re thinking of,” Anna commented, sitting deep on Sid’s hog and grinding back and forth.
“You really think she can handle both of us…together,” Sid asked, continuing to grope her great tits from underneath.
“Only one way to find out,” Anna replied, equally nervous and excited for the new experience.
In a last attempt to get him prepared, Anna forgot about riding the man beneath her and focused on Phil. Opening her mouth as wide as possible, the actress took his ebony cock into her mouth and didn’t stop until her adorable nose was being tickled by his pubes. Waiting until enough spit had built up, she pulled her head away and left so much thick strands of spit on his pecker that some was dripping off.
Once Phil pulled away from her and stepped to the edge of the bed, Anna knew what was to come instantly. Resting all her weight down onto the muscular man, who was still finding a way to ram her with his thick cock, the movie star focused on her breathing and relaxed. Sure enough, she felt his lubricated tip rub along her already-fucked asshole before it came to rest in the center.
“Ready for the two-for-one best friend special,” the black man asked, primed and ready, only waiting for Anna’s go-ahead.
Anna Kendrick had a plethora of emotion strike her all at once. She was reminded of Sid at that time, still sitting on his lap with all 8 inches of thick manhood inside her as her tits pressed against his chest. Her cute little ass was presently perfectly back towards the crouching man behind her with her tight asshole now an easy target to penetrate, once she gave the all-clear. She felt nervous since taking two cocks in her holes at once, not having done it for years, however she was desperate to show her appreciation to these men.
“Give me both those cocks,” Anna said with confidence.
The thought of this petite, normally seeming actress being willing and able for this extreme challenge was almost unbelievable. However, Phil wasn’t about to wait for Anna to wise up and come to her senses.
With his cock already slick from both the star’s pussy juices and mouth, he still bent down and spat a wad of saliva in his hand and massaged it into the smooth skin of his penis. The slickness of his dick combined with the fact his co-worker sodomized Anna not long ago meant that when he pushed his tool harder forward, he found his good-sized cock slid in without too much difficulty.
“Mmm…ughh…eewww,” Anna grunted, more from discomfort then actual pain.
For Anna it felt fuller since there was another cock in her with only a thin barrier separating the co-workers, but it was manageable. The two men were considerate as they thought she might need a minute to adapt so Phil only resorted to fucking her slowly with the first 2 inches of his impressive cock while Sid laid still beneath her.
The black man was having to fight his animalistic instincts by not just plowing full powered ahead into her tight ass and impale Anna on his cock in one quick motion. It was a challenge but he held that side of him at bay as he careful only worked a small amount of himself into her booty, but even that felt amazing. Her asshole was snug, but not painful as it clamped around the neck of his cock.
“Can’t believe you two are double stuffing that tiny girl,” Karl said from his chair
It took less than a minute for Anna to have grown accustom to having a cock in both her ass and pussy at the same time. It was no longer causing pain, in fact she was actually growing to like the feeling of being full of dicks. Using her hands on Sid’s strong chest, she began to push back into both their meat poles and started fucking them.
“Ohhh….me….aahhhhh…neither,” she moaned loudly.
With Sid sitting on the couch fucking up into her twat and Phil standing behind her with his strokes lengthening into her asshole, Anna was somehow blissful. She felt so unbelievably tight that words couldn’t express it. The whole encounter of being wanted so badly by two men really turned her on, and the friction their two cocks were causing on the thin membrane between her pussy and anal walls was almost driving her mad with pleasure.
“Oh God it’s so good,” she screamed again. “Just like that!”
“I really found a sex freak this time,” Karl continued his commentary as Phil and Sid wildly thrusted into their respective holes.
It had took a few minutes but eventually both men got to the point where they were impaling the girl with large tits with their entire pole. It was jerky and not the smoothest fucking as neither of the trio had any experience with this, but judging by the looks and noises being emitted by them, they were all happy to figure it out.
“Of God! Yes…shit,” Anna exclaimed at the top of her lungs when her clit grinded against Sid’s hard abs.
Anna relaxed down onto the bulky sound guy completely and let them pummel her body with their hard tools. She figured she may as well since they were doing great, only managing to squirm into a position that gave them better access to what they were doing. She lost track of time as she basked in the glory of two men taking turns going balls deep in her anus and twat, bringing her rapidly towards a strong orgasm.
“OH YYEESSS,” she swore as an orgasm ripped through her curvy body.
Anna cumming started a chain reaction for the two other men. Phil and Sid’s fucking was finally catching up with them. As the Pitch Perfect star came, her pussy reflexively clamped down even harder around Sid’s throbbing cock, trying desperately to milk him of his jizz. He gave in and groaned in delight as his jizz rocketed from the tip of his penis deep into her twat in the biggest orgasm of his life as well.
While his muscular co-worker was painting Anna Kendrick’s pussy in his spunk, Phil found himself as the last man standing. However, he knew that wasn’t going to last much longer, as he was at the point now that he needed to cum urgently. He only had seconds to weigh up his various options on where to blow his load, but one place stood out more than the others.
“Shit…need to cum.”
“You want…my tits…don’t you,” the panting girl asked, looking back over her shoulder.
Seeing the recognition in his eyes, Anna smiled at her good guess. Most men that she graced with joining her in bed always like popping on her chest and based on the way Phil fondled her tits more than the others, it was a safe hypothesis.
Now that he had the go-ahead to cream on her, his preferred destination at that, he pushed his hips harder up into her as one last time before rolling her over onto her back. He knew he wouldn’t last any longer than a few more second, especially with the knowledge that his spunk would soon be sprayed on her amazing asset.
“Gonna cum,” he warned as he crawled up her body, straddling her stomach.
Aiming his tip at his target, Phil let fly several long strands of cum that splashed with force against her glistening skin. Anna loved the feeling of the warm cum coating her sweat-covered body and the dark-skinned man was definitely providing her with plenty of liquid. With all his energy leaving his body at the same time, before rolling off the star he looked down at his handiwork. His hot, thick, sloppy load spilling over her big jugs, making them glisten in the light.
“Holy hell that was good,” Phil grunted, laying beside the lithe actress after emptying his entire load onto her large tits.
“I will never forget tonight as long as I live,” one of the men groaned.
“A…fucking…men,” Anna agreed.
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Anna Kendrick: Winning at all Costs