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thechemist

Winning At All Costs (Anna Kendrick)
« on: November 27, 2019, 10:39:54 AM »
Title: Winning At All Costs
Author: The Chemist
Celebs: Anna Kendrick
Codes:  MMMF, anal, DP, oral, rim
Summary:  Anna Kendrick has her game rigged so she win. As a reward for the men that helped her, she gives herself to them for the evening.

Disclaimer:  This is an act of fiction. I do not know Anna Kendrick at all and this scenario did not actually occur. I make no money from this story.



“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 a 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 succeed 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.

 
The following users thanked this post: Viri

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Viri

Re: Winning At All Costs (Anna Kendrick)
« Reply #1 on: November 27, 2019, 10:26:56 PM »
Wow, that was awesome. Had never read this story before, loved it!  ^-^
 

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thechemist

Re: Winning At All Costs (Anna Kendrick)
« Reply #2 on: December 10, 2019, 04:11:20 PM »
Title: Winning At All Costs Part 2
Author: The Chemist
Celebrities: Anna Kendrick, John Krasinski
Codes: MF, M+F, Oral, Blackmail, Watersport
Disclaimer: I make no money from this work of fiction. Do not read if under 18. These events did not happen, I do not know Anna Kendrick, John Krasinski, nor am I associated with them in any way

Summary: John finds out that Anna cheated at the lip sync battle. She agrees to three ‘wishes’ for him. The first - being the headline attraction at a gloryhole

***Warning - Some elements of this story are some hardcore themes. Everything is consensual though, even if it originally starts as blackmail. Also, there is some brief piss play/watersport towards the end, as well as some ATM which some don't like. Just wanted to warn everyone. Lastly, there is a rougher face-fuck scene at the very end, but once again it is consensual***

Thanks: This idea was inspired by fellow member fenderdiesel, so wanted to give thanks where thanks is due.



Anna Kendrick always loved movie premieres. They were a fun time for her to get dressed up, which usually meant wearing something which flaunted all of her best assets. In Anna’s case, that was her famous cleavage. Her boobs were probably only a C-cup, but because they were on such a slender, petite woman, they looked huge.

The other nice thing about walking the red carpet was that you typically bumped into Hollywood friends that you haven’t seen in awhile. This premiere was like most of the others she attended - she slid into a dress that hugged her form perfectly, but her wonderful tits on full display in a cleavage-revealing outfit, and met up with lots of fellow celebrities she hadn’t seen in quite some time. However, as she was seconds away from finding out, not all were welcomed.

“You cheated,” a male voice hissed into her ear from behind.

A shiver went up Anna’s spine. It wasn’t the fact that someone was able to get up right behind her, close enough to speak directly into her ear. It was the fact that she knew who that voice belonged to. Even more worrying were the facts that his tone was dripping with venom, white hot anger in fact, and that the petite starlet knew exactly what John Krasinski was talking about.

The event in question was a hotly contest bet between the two actors several years ago. They were performing on a show where two celebrities went head-to-head in a lip syncing competition. However, John and Anna had an additional wager on the contest - if Anna won then John would stop harassing her. Even in the MeToo era of Hollywood, John was too clever by half to be caught up in an scandal, mainly because he prayed on women that had a loose or sex positive reputation and were unlikely to make waves. If he won the bet then she would spend the night with him again. Sounds not so bad, getting to sleep with a tall, gorgeous man but he was an absolute monster who was into the hardest and roughest of sex.

“John, um, hi,” was all Anna could think to say at first.

“Smile for the cameras,” John told the petite actress, pulling her in nice and close and having their pictures taken for the gathered media.

“Everyone, the movie will begin eminently. Please come in and take your seats,” one of the pages of the theatre announced.

“Oh, so sorry John, gotta go grab my seat,” Anna quickly said before practically running off, a feat made all the more impressive given her stiletto heels.

*   *   *

Anna was thanking her lucky stars that she was saved by the proverbial bell moments ago. Though it was only a short-term fix, avoid John until she could think of a plan was the best case situation. The seats were pre-assigned, so Anna gave her invitation to the steward and was brought to her seat. However, her relief of getting away from the red carpet conversation was short-lived as none other than John Krasinski sat down beside her.

“John...the seat is…” Anna stammered.

“Once I realized we were both coming tonight, the manager had no issues accepting my request to be seated next to my former fuck buddy,” John said with a smile full of malice.

“Oh,” Anna said, feeling herself slump in resignation. “About that lip sync battle…”

“Don’t bother denying it, it’s beneath even a piss-drinking slut like yourself,” John spat, his voice projected low enough so no one else in the theatre could hear. “I knew you couldn’t beat me fair but I finally got the proof I need from that sound controller. You faked the crowd noise.”

“Fuck,” Anna swore, knowing he had her dead to rights.

“So here’s the mother fucking deal. You are at my beck and call for 3 favors. No arguing. You drop whatever you are doing when I tell you. Understand?” John stated.

“But…”

“I don’t care if your mom is on her sickbed. You come. It’s 3 favors or your career is ruined. And you damn well know I can follow through on it. Remember Ashley? Most people don’t. Now she can’t even get a job entertaining at Chuck E Cheese,” John added. “So I think I’m being pretty fucking fair by only using you 3 times for the shit you pulled.”

Sadly, Anna knew that was true. On everything he was saying. Even though she had been in a bunch of hit movies, John had gathered a lot of power in Hollywood. If he decided to crush her career, he could. And she was 35 years old, so the fact she was this busy was an anomaly in her line of work unfortunately. Though she was as hot as ever, having the numbers game, as well as a powerful figure against her would cripple her. Therefore, Anna nodded her head in ascent.

“Fine. I’ll do it,” Anna agreed, defeated.

“Good girl, not like you had a choice. But if you act the sad victim during my wishes, then, well, it won’t be pleasant,” John warned before giving her his grin that was capable of dropping panties. “Besides, everyone loves Anna Kendrick for her sass!”

*   *   *

It certainly didn’t take John long to get back to her, but it wasn’t exactly what she was expecting. Their first and only time hooking up was when they were both out drinking all night then returned to his place afterwards. That’s when his inner demon came out as it was some of the hardest and roughest sex of Anna’s life. This was saying a lot since Anna was as horny and kinky of a girl as it came. Though she never stopped him, she also resolved herself to never sleeping with the married man ever again.

The text she had gotten from John listed an address and time. Throwing the address into her maps app, she discovered that the location was a sex shop. Though she had frequented a number of these establishments throughout the town, the petite actress hadn’t been to this particular store because it was located in the middle of downtown, which was notoriously a rougher area of town.

“Hi. 9th and Central,” Anna said after hailing a cab.

The petite star saw the cabbie do a double take on her before speaking. “You sure? That’s not exactly a nice area of the city.”

“Sadly I’m all too aware,” Anna agreed.

The pair chatted pleasantly for the 20 minute drive, which helped take Anna’s mind off what John had in store for her at the sex shop. However, all too soon the cab was slowing down and asking for an exact address, trying to be as nice as possible by getting her closest to her location as he could. He sounded surprised when he was told what building she was going to, but gladly accepted a large tip from the petite actress for the considerate service.

“Here’s my personal number. If you give me a little heads up I’ll make sure I get here ASAP,” the kind older man told the 35-year old.

“Thanks. I’ll probably take you up on that offer,” Anna said with a warm smile.

Anna didn’t watch the cab drive away, instead she hustled her way into the safety of the building. However, when she entered the sex shop, she was surprised by what she found. As previously stated, she was a frequent shopper at these types of places, even though mostly she would use online shopping. What was truly remarkable was that the adult store was packed, when normally 6 people inside was considered a busy night. However, inside this one, there had to be at least 2 dozen patrons.

Looking around at the faces, Anna found that many of the people were likely homeless, at least given the fact that they looked as though they hadn’t showered in a week and there clothes were dirty and ripped. Some in the crowd looked like they were there for shopping, but they were in the minority.

“Anna Kendrick, everybody,” a voice from the overhead speaker announced.

Anna’s face instantly reddened from all the attention being drawn to her while in this seedy adult store, but most of the men looked confused than excited from recognizing her as a popular actress. There were several of the men who pulled out their cell phones and snapped her picture, but even if they posted the pics, which they were likely to do, it wouldn’t hurt her reputation at all. After all, she’d outed herself for being a frequent porn watcher, & masturbating in the back of movie theatres, so being caught in a sex shop would be fairly on brand.

As Anna slowly wondered further into the store, she noted the clean-cut man behind the counter. After snapping a few selfies with 3 or 4 men, she reached the middle-aged man who was her guess as the owner, or at least the manager.

“Your master is in the back,” the manager said as she got close enough. “Center door.”

Anna understood he meant John so she picked her way through the crowd of homeless men easily enough. As she reached the back section, she noted 4 doors. One was clearly marked as theatre, and inside through the small glass window she could see maybe a dozen seats facing a large screen playing some porn. The center door had a lock on it, though she could see the bolt wasn’t latched, meanwhile the doors to its immediate left and right were open but small. Roughly the size of a changing room.

“You made it,” John said, greeting her after Anna entered and closed the door behind her.

“Why are we here,” Anna said before looking around. “Oh...I see.”

Suddenly it clicked into place for the petite actress. The adult store, the 2 dozen men just lingering in the store, and the room she was in. This room was longer than the others but just as narrow. In fact, she could stand sideways and reach wall-to-wall with elbows. John was standing at the back of the thin room, smile on his face while the main tip off to Anna of what was about to happen was the matching set of foot-long holes at roughly waist height from the floor.

Speaking into the microphone so his voice could project to the rest of the store, John announced. “Tonight’s gloryhole performer is Anna Kendrick! Can I get the first two men into the rooms.”

“What the fuck John! Announcing that it’s me…”

“What does it matter. Only a handful of them out there have phones and know who the fuck you are. And so what? No matter who they tell, no one will believe that Anna Kendrick is actually sucking them off.” John replied.

Anna was shocked into silence at the situation dawned on her. While John was right, and that only half-a-dozen men out there could tie it together that the Pitch Perfect star was about to suck them off, it was still an asshole move on his part. Then again, it was totally on brand for the pseudo-nice guy.

“So what’s the deal, John? Suck off whatever dick that pops through the gloryhole?” Anna said with anger, hand on hip.

“Perfect. So happy you get how a gloryhole whore operates.” John retorted. “And no arguing on this point. I’m recording this for personal use. I won’t release it ever since I’m in the fucking taping too, so it would be mutually assured destruction. Not good for either of us. Therefore, I want energetic, happy blowjobs. I want to see the money shot and I want to see you smile as you swallow. Understand?”

After a moment to think, the petite actress asked. “Any way to talk you out of this?”

“Nope.” John said with a victorious grin.

Anna didn’t verbalize her response. Instead, she took off the leather jacket she was wearing and threw it at John to hold. In only a tee shirt and jeans, the Pitch Perfect star went so that she was in front of one of the gloryholes and dropped to her knees. Looking through the porthole, she could see a man with clean jeans undoing them. Knowing she was moments away from showtime, the actress put on her best smile in order to make the man she cheated happy.

In truth, if it wasn’t for the blackmail, Anna would have been happy to subject herself to a gloryhole fantasy. After all, she had participated in a blowbang several times in her life, the biggest involving ten men, and loved it. While true it was a lot of work and her jaw ached for the rest of the night, getting to please so many men and swallow that many loads of cum was an unforgettable experience. Therefore, as the first of many men waddled up to the gloryhole, Anna channelled her inner sex addict mindset and let the horniness of sucking off so many unknown men wash over her, zenning her out.

“Let’s do this,” she said aloud, almost as a mantra.

The first dick was still soft as the owner stepped to the open panel. Anna thought nothing of it as she wrapped her small fist lightly around the flaccid piece of flesh. Moving her hand up and down in a fluid motion, the actress felt it start to harden under her touch. After 2 dozen mini-strokes, Anna leaned in and took the first of many into her mouth. Only 4 inches long while hard, Anna took the entire dick into her mouth, formed a seal with her lips on the smooth skin and began to bob.

Up and down, Anna’s mouth moved along his small but pleasant dick. With each time she pushed her face forward, her nose poked against his fairly flat but bushy lower abdomen. That didn’t detract the petite actress from going about her work though.

After the first ten bobs of her head, she noted only some little groans from the man in the room. Stepping up her technique, Anna extended her tongue as her nose pressed into their pubes, licking the sensitive part where shaft met the start of his nut sack. As the first man proved resilient to that trick, Anna would leave her lips pressed tight around the base of his cock, nose completely buried in his thick pubic mound, feeling it start to itch, but that didn’t distract her from sucking hard on his fully throated cock.

“Gllkk gllkkk gllkkk,” Anna gargled around his submerged dick in her gullet.

Annadidn’t dissect her thoughts further, but she was impressed that John hadn’t brought a bunch of half-cocked guys ready to pop with the lightest of stimulus. Eager for a challenge, Anna got comfortable on her knees and got to work. Shortening her bob so her mouth only worked the top two inches, her dainty fist gripped the remaining half and stroked her hand and mouth pressed tight together and working as one. 10, 20, 30 strokes and still the first guy held out. Anna broke her lip contact with him, though her mouth and his dick were still touching via a lengthy rope of spit, as Anna took a deep breath of air before going back in.

Anna gave the resistant man her variety pack as she called it. 10 bobs of each technique should do it, she thought. She used her mouth and fist in unison first, then deep throated his small offering for nearly a dozen seconds. Pulling off to capture some air, Anna beat his meat furiously for 10 strokes then went and did 10 bobs with only her mouth. As her hand and mouth went back to suck him off together, Anna heard a 3-rap knock on the wall.

“He’s about to cum,” John said, telling the petite star the arranged signal.

Anna went into her finishing posture, however the first trick of looking up and making eye contact with the guy as he blasted a wad of jizz down her throat didn’t work in a gloryhole situation. Regardless, her hand lengthened it’s stroking distance as her mouth only sucked on the tip of his cock in fast bobs, pleading for his cum. Knowing John wanted the camera to capture the money shot, once Anna felt the first streak of cum on her taste buds, she only used her hand to beat him off so his head could rest on her tongue and allow her to collect.

Proud of herself for getting the first one done with, Anna turned to the camera and showed off the full tongue of cum that she had earned. Her hand had remained lightly fondling the man’s balls as she showed off his cum load to John, noting how his cum had the taste of pennies before she closed her mouth and swallowed his load.

“How was the first?” John asked as his petite guest was already pivoting to the second window.

“Pretty good,” Anna said, reaching out and stroking the dick in the panel.

Right from the off, Anna could tell this dick belonged to one of the homeless population. His cock just felt...sticky. Not delaying to find out since it wouldn’t help anyway, Anna leaned forward and took the whole semi-hard dick into her mouth in one shot before slowly dragging her lips away. Sure enough, his cock tasted as if a shower was a rare commodity, though his flesh was slightly longer than the last.

“Looks gross. Taste it too?” John asked as Anna used only her mouth to suck off the man.

Anna was thankful for the chance to pull her lips after the gross tasting cock and confirm as much to John. As her hand beat the homeless man’s dick, she realized that the aftertaste from the residue on the older man’s member was potentially worse than when she was tasting it fresh. Therefore, Anna went back in and took him inside her mouth, using her hand and lips together.

For two straight minutes Anna didn’t pull her mouth from his cock. It was disgusting, but nothing she couldn’t handle. It also helped that at only 5 inches long and not very thick, the Pitch Perfect star could breath through her nose so she could constantly glide her tongue and lips on the man’s dick. The only time she varied her technique was to take his entire cock into her throat, but after only a few seconds she had to pull him out for fear of gagging. It wasn’t that she couldn’t handle the throat bulging depth, hell, that was something she’d been doing since she was 19. It was the stench coming from his body that was too much to take, therefore she quickly resumed the mouth-fist combo to get the homeless man off.

KNOCK KNOCK KNOCK

“Oh thank God,” Anna thought as she fiercely beat him off as her mouth waited to collect his semen.

Anna realized that this homeless man hadn’t cum in quite some time given the volume of sperm filling her mouth. In fact, the load was so large that a small bead of white goo spilled over her lips and down onto her chin. At this point, Anna decided to swallow the mammoth load of cum, adding this salty batch to the one she ate only minutes ago.

“You got some on your shirt. Toss it here so it stays clean,” John suggested.

Anna gave him a smile for his less-than-smooth way of making her get topless. However, it still was successful as Anna instantly grabbed the hem of her shirt and pulled it up over her head. Her bra quickly followed, which John caught, leaving the petite actress topless. While Anna may have been tiny, her tits were anything but. Large, perfectly round and bouncy, Anna’s boobs were legendary in Hollywood and though John wasn’t the type to hand out compliments, he was more than happy to see those beauties once more.

As Anna turned to the next window, this time an already erect black cock waited for her. Anna eagerly attacked the dick with her mouth, seeming to be happy to have some color variety with her gloryhole blowbang. After a couple dozen strokes with hand and mouth, Anna took him all the way into her throat, holding his there for 6 seconds before pulling off. Her goal was to add some extra saliva to his dick, which worked perfectly, allowing her small fist to glide faster than every on his ebony rod.

“God, you were meant to suck cock,” John commented as Anna sucked him off without hands.

“Awhh! John! You’re gonna make me blush,” the 35-year old actress retorted while stroking him quickly with her hand.

With a thicker 6 inch cock to work with, Anna found that this blowjob was sloppier and louder than the ones previous. She didn’t do anything about the long drool string that was dropping down from her mouth, down her chin and onto the upper part of her right chest. Instead, she focused on the throaty, wet suck job she was giving to the black man. Adding a new twist to the folds, Anna switched tacts to only swirl her mouth and tongue on the head of his cock while her fist pumped along the rest of the shaft. Of course she would thread other techniques into the mix, but she would always return to this shallow suck after a dozen or so bobs of other ways.

“Not as easy as you thought?” John commented as Anna held him down her throat for nearly 10 seconds.

“Ggwwwkkk,” Anna coughed, spitting a mouthful of spit onto his cock but more falling down onto her swaying tits. “Love a challenge.”

Anna now had glistening boobs from her spit, as well as a number of drool strings hanging down over her chin. This didn’t distract her though, as her mouth and thought process were solely on the ebony cock in front of her. Up and down her lips glided along the 6 inch dick, sometimes blindingly fast, sometimes stopped altogether with her only using suction. Other times her depth would be his throat down her throat, moments later she’d only be sucking his tip.

KNOCK KNOCK KNOCK

Rather than shoot out of his slit with force, the black man’s cum dribbled out of him. It surprised Anna at first but she only lost the first big glub to a fall to the floor before she dipped her head lower to catch the rest with her tongue. She quickly showed the camera the half-full mouth of salty jizz before swallowing down, using her tongue to next like the glob that was dangling on her thumb.

“You noticed the big glob that fell, right? And how we agreed you’d drink every drop,” John reminded. “So be a good cum-guzzling jizz demon and eat it off the dirty floor.”

Anna didn’t so much as voice a complaint. Instead, the gorgeous girl tossed her long auburn locks over her shoulder, scooted back on the cement floor and bent all the way forward. It was easy to identify the fallen droplet of white cum on the all black floor. Keeping her piercing blue eyes trained on John, Anna stuck her tongue out and corralled the fallen cum until it stuck onto her taste buds and she was able to drink it down.

“That’s a good little cum slut,” John complimented before letting her get back to work.

The fourth man was waiting with an erect cock was was likely as fat and short as he was. As she got started by sucking him off without hands, Anna was surprised to feel a hand on her tit, groping lightly before playfully teasing the nipple. The boob play made her blow the other man with newed vigor. She had to stifle a laugh at the sight out of the corner of her eye of a naked arm extending out from the hole behind her and fondling her breasts.

Anna had decided that on this short, fat cock she’d only use her mouth, challenge herself a little. With her hands only being used to steady herself on the wall, Anna bobbed her lips along his shaft from tip to root, only stopping and reversing course when her nose and chin poked his large gut and balls, respectively. She could feel the spit building in her mouth and spilling over her lips, but she let it drop onto her sway tits as she focused only on delivering pleasure.

KNOCK KNOCK KNOCK

Even with the eminent ejaculation, Anna didn’t use anything but her mouth to finish the man. Shortening her bobs so her mouth only did his tip, Anna’s head was practically a blur of motion. This time Anna Kendrick didn’t spill a drop of cum, extremely thick and kinda oily cum, as it pooled in her mouth until she gulp it down all at once.

“Look at this,” Anna said, spinning around and finding the next guy waiting. “Already hard and waiting for a good suck.”

As Anna reached out and stroked him lightly in her hand, she noted that this dick was one that would make any size queen happy. He was both thick and long, likely a good 7 inches and she was unable to circle her fingers around his girth. It did have a negative and that was tasting of chlorine, as though the only time he washed was in the community pool. It wasn’t as revolting as the homeless man from several turns ago, but not by much.

And of course he wasn’t a two-pump chump. Nope, this guy was making Anna worked hard, thus taste his gross pool cock for over 5 minutes. At first the Pitch Perfect star was only using her mouth to suck his tip while her fist did the rest of the shaft, but she needed to alter her approach when it was doing little for the big dick man. So she had to use her tongue and mouth and more and more of his chlorine cock, bobbing with her lips only, deep throating and even just licking up and down his shaft for awhile. However, all men had their breaking point, especially when it came to a blowjob from the talented Anna Kendrick.

KNOCK KNOCK KNOCK

Once more Anna waited a few seconds for the entire load to be deposited onto her tongue. Another few seconds to show John and the camera then her lips pressed together, her throat opened and the cum was drank down, all with a smile on her lips.

The next 2 cocks passed by fairly quickly. Both were on the thinner and shorter side with the longest one maybe 5 inches. They both belonged to homeless men, with neither having showered or washed this century in Anna’s estimation. However, neither had overly offensive cum, maybe more salty than she was accustomed to but not terribly so.

“Why not take the pants off too?” John asked.

Anna knew the pseudo-nice guy for long enough so understood this wasn’t a suggestion. Taking it as the request it was, the petite actress undid her jeans and wiggled her slender legs out of the tight-fitting pants while on the ground. Her thong threatened to come down with them and look in John’s eye let her know it was a good idea so Anna pulled her thong off as well, rendering herself naked in the small room.

Anna went at the next cock, a soft dick but she knew he’d be long but thin. A good dick for anal she thought. With the thought of anal, one of her favorite sex acts, Anna felt more playful so as her hand took over stroking his dick, she angled him upwards so she could lean forward and take the first nut into her mouth. Both man and Anna moaned as she sucked hard on his right ball before switching over and doing the same to the left one.

“Do you like having your balls sucked or only licked?” the cock-hungry actress asked the mystery man.

John couldn’t hear the man’s answer but when Anna dipped low and once more sucked on his nuts, he had the answer. The half a minute of ball sucking had the man hard as a rock, allowing Anna to take the man fully into her mouth and bulge her throat. With ample amount of spit now decorating his thin cock and even more falling on her perfect tits. Going back into deep throating his long cock, Anna’s nose pressed firmly against the wall but that didn’t stop the petite actress from pleasure the hell out of the lucky man.

Anna was treating this man to lightning mode. She alternated with speed between three techniques in order to get him off in record time. The first was the deep throat, at which point she would stick her tongue out and simultaneously lick his balls. Next she would pull her mouth from him altogether so she could use two hands this time to stroke him off. Next was mouth and hand in unison. After only 3 minutes of this attack, the noise she was looking forward to was sounded.

KNOCK KNOCK KNOCK

Once more it was during her swift mouth-hand combo that earned her the rap on the wall, having brought her 8th man to climax. The energetic sucker gave the homeless man another 3 rapid bobs of her head then pulled back so she only beat his load right into her wide open mouth, pooling the cum there before ultimately swallowing the prize.

As Anna moved onto the next dick, she realized that she wasn’t even picturing who the dick belonged to. When she had done a blowbang at her friend’s 30th birthday party a few years back, Anna knew the guys and knew what they looked like. However, she was finding it so extremely hot to just use these faceless, mystery men for their cocks and that’s it. They weren’t people, only dicks. And she was just a mouth for them to deposit their jizz into.

Anna was in a flow now. With the eighth man done and dusted, Anna pivoted to the next dick on her chopping block. As she started in one a dick she would describe as average in every way, Anna ignored the slight ache that was developing in her jaw from the nearly 45 minutes of blowjobs, as well as the slight stomach ache she was growing from swallowing down 8 loads of not the best tasting semen. Instead, she kept her lips moist, head bobbing and hand jerking until another goo reward popped onto her tongue before it too joined the 9 other loads in her stomach. However, her greatest challenge was heading towards her face currently, and the moment it breached her mouth with her lips wrapping around the homeless man’s cock and the taste buds of her tongue contacting the underbelly of his manhood.

“Gaawwwkkk!” Anna nearly reteched, pulling her face away from the man, trying not to throw up. “Oh God!”

“What’s wrong, AK?” John inquired, wide smile on his face at the slender woman’s sudden discomfort.

Anna, being the sex fiend that she was, went back in for another suck and much like the first time nearly gagged. “EEECCCHHH! Shit! It tastes like pure shit.”

“That is probably cuz I banging my girlie friend in her shitter, like, 30 minutes ago,” the hobo explained from the other side of the wall.

The 35-year old actress took a look at the gross man’s manhood and noted several things, particularly a few different colors. For one, his dick was reddened, likely from having just fucked some woman in her vice-like grip of her asshole. And then even after Anna had done two short sucks on his dick, there was also some other discoloration, likely the homeless man’s girlfriend’s ass juices, which was more likely than not causing Anna to gag.

“Show must go on,” Anna verbalized to herself.

With her resolve and courage rallied, the petite star went about her task, which was sucking on this truly putrid cock until he sponged in her mouth for the 10th time in under an hour. Screwing her eyes closed, Anna pushed her face towards the hole in the wall and took the unhygienic man back into her mouth. Figuring speed was the best choice since he’d only just just in some woman’s asshole before wandering in to her gloryhole, the Pitch Perfect actress latched her lips around his dick and got to work sucking him off.

Initially Anna opted for the swiftest blowjob pace she could manage, which was saying something considering she’d been on her knees with 9 other cocks in her mouth for the past hour. Yet the 35 year old actress showed no lack of stamina by rocketing her lips along the first 3 inches of his horrible cock. She was able to maintain a near neck-breaking pace for a good minute before she needed to surface from his manhood and gulp down some fresh air and starve off a wave of nausea.

“Dear Lord, sir,” Anna criticized before spitting onto his midshaft so her hand had lubrication as she stroked him off.

After her complaint, Anna went right back to work though. This time her mouth and hand worked in unison and she was able to stay with her lips around his meat pole for a good two minute of her most intense sucking before she had to pull off for a quick break. After 10 seconds of beating him off, Anna went back in, tasting what could only be described as the fresh flavor of ass from the dirty man.

Watching such a beautiful girl with a face of an angel do something so nasty sent a surge through John as he watched on, his own cock an iron bar in his pants. He could only stare in amazement of how Anna Kendrick could continue going down on this filthy man for what was now 10 minutes and counting. She needed to surface for air constantly, and her face was perpetually grimacing, but she dutifully stuck to her task despite the odoress cock, which John could smell the stink a good 8 feet away. Yet over and over again Anna’s auburn haired head bobbed forward and back along his length, tongue gliding along his underbelly, her lips pinched tight long the circumference of his manhood, her right hand pumping and her left fondling his nuts.

KNOCK KNOCK KNOCK

“Thank Jesus,” Anna praised without being religious in the slightest.

The man exploded right away, barely giving the Oscar nominee enough time to catch the first squirt of cum. Given the fact the gross hobo had fucked to completion not long ago, Anna was still impressed that the man could garner as much semen to nearly fill her mouth less than an hour later. With a quick look at the camera and showing of a mostly full mouthful of jizz before a quick swallow and the load joined the 9 others in her stomach.

Anna didn’t know what compelled her to do it, but using one hand to hold the gross man’s dick steady, the tiny actress began using her tongue to lick all the bits of his pole that she hadn’t sucked on initially. Once more the strong, intense ass flavor filled her taste buds and threatened to make her retch, but Anna continued on. Licking down both sides to the base in multiple passes, Anna took a moment to make sure she wouldn’t throw up from the flavor before doing likewise with her tongue to the top and bottom of the homeless man’s disgusting junk.

“God, I’m such a slut,” Anna said, mostly as a compliment to herself than as self-shame.

By the time Anna was down licking down his gross cock after sucking him off to completion, a small bead of cum had appeared in his pee slit. Since there was no cum-dodging tonight, Anna extended a tongue and slurped up the last of his load. Completely done with the filthy homeless man, Anna pivoted back to the other window where there was a semi-flaccid dick already waiting. Not wanting to disappoint, the Pitch Perfect star opened her mouth and dove right in.

Within a minute of getting the 11th man hard and sucking him off expertly, Anna felt a splash of fluid on her back. Instantly she thought that a guy must have popped his load just listening to her sucking another guy off and decided to pop on her back. She had heard of two-pump chumps, but this was a whole different beast. Regardless, Anna wanted to collect the rest of the load so she showed off the flexibility she earned from countless hours in dance training by leaning all the way back so her face was under the spewing cock. However, as a thick flow of warm golden urine splashed on her silky auburn hair, all over her face and even into her mouth before she had the presence of mind to clamp her lips closed and straighten back up.

“Dude! What the fuck,” Anna swore as more of the man’s piss splashed onto her back and down onto her bubbly tush.

“Don’t you dare move,” John instructed. “Keep sucking that dick in front of you.”

“But John, a fucking hobo is pissing on me!” Anna fumed, coming out of her self-described ‘slut mode’ for the first time since starting this gloryhole challenge.

“Oh, so that was the first time you let a random guy give you a golden shower? Or piss right in your mouth and gleefully swallow it?” John asked sarcastically, all while Anna stayed in position. “In fact, I seemed to remember you kneeling in the shower with me, taking mouthful after mouthful of my warm piss down your gullet not too long ago.”

With the fight already out of her, Anna once more accepted her fate and found her calm mindset. After all, she had chosen this and not even the feel of urine being streamed on her hair, down her back and into her ass crack would ruin it. A gloryhole was one of the few remaining sexual acts that were still on her preverted bucket list, so why should she let some gross homeless man’s piss getting blasted onto her face and even down her throat rob her of so much joy.

“Yes, you fucking pervert. Piss on me,” Anna said, snapping fully back into the moment.

In truth, Anna had lost some steam since the man who tasted of actually asshole. However, apparently being degraded so utterly like being used as a urinal like she currently was, made her come back alive. Bobbing on the man’s dick with renewed vigor, Anna was a blur as her mouth worked up and down his short but fat pole.

Lucky number 11 nearly blew his load right away when Anna Kendrick of all women started playing with his balls with her tongue as she continued to stroke his cock, but he was determined to prolong the act as long as humanly possible. Her talented tongue felt great as she took turns taking one of his large testicles in her mouth at a time.

"Holy fuck," the man behind the wall exclaimed once she moved up and took the tip in her mouth again, gladly slurping up the clear pre-cum that she milked from him.

"Trust me dude, you haven't felt anything yet," a wet-haired Anna proclaimed with a smile as she immediately shoved half his length into her mouth.

Using her mouth and hand in unison, Anna started giving the lucky man a sloppy blowjob, making sure she kept eye contact with John to her right and made loud sucking noises. Anna would routinely take the chubby dick down her gullet, bobbing him in and out of her throat. The deep throat technique caused spit to coat his cock, all while the actress kept slurping up some for later use or letting the other half fall to her pillowy large tits. The man on the other side of the wall couldn't help but tilt his head back every now and then and moan a swear word.

"Fuck, this is a good cock," Anna said as she hooked her fingers onto the bottom of the gloryhole and used her strength and pull herself forward so that she could slam his whole length into her experienced mouth and down her throat.

"Old nuns, dead kittens, serial killers," the man repeated as he tried to think of unsexy things so he could hold out as long as possible under the talented actress’ deep-throating assault.

"Your pubes tickle my nose," Anna jiggled before pulling herself forward and taking him down her throat again.

KNOCK KNOCK KNOCK

"Cum in my mouth, big fella," Anna said before just taking the tip back in her mouth and milking the shaft with her hand.

Anna was able to keep sucking on his dick for an extra 10 seconds before she felt the tell-tale quiver of his pecker. With a moan and extra thud on the wall as his head pressed against it, the 11th man blew his load into Anna’s eager mouth, completely filling her oral orifice. Once he was done, she moved his dick from her and showed John and the camera his cum before swallowing it down, smiling afterwards.

Still grinning, the 35 year old actress spun on her knees, preparing for another cock to greet her in the gloryhole but no one was there. Thinking about it, the man who had showered her hair, face and mouth must have been the homeless man with the gross cock she sucked off earlier. With a shrug of her shoulders, Anna turned back to the hole she just finished sucking lucky number 11 off but found the room was empty as she looked through.

“Let’s make it an even dozen for you,” John said.

When Anna turned to look at her former co-star, the man already had his pants down. More importantly, his cock, a veiny 8 inches of girthy flesh, was already hard and being stroked. Though she had been coerced into the gloryhole situation initially, Anna would have been damned if she didn’t thoroughly enjoy herself. And now seeing John’s massive dick again made her panties dampen even more, despite the fact she was a complete asshole to her. She just couldn’t help herself.

“Is that gorgeous piece of meat for me,” Anna asked, eyes transfixed on his pecker as she seductive crawled her naked body towards him.

“Mmhm…you must really want it bad,” John commented, bundling up her long auburn hair in his hand as she got to her knees before him. “I remember that glint in your eye the first time we hooked up. I knew then and there I needed to make you mine.”

“I’m all yours,” Anna cooed, licking her lips in anticipation.

She opened her mouth wide and took the first several inches of his penis into her moist warmth. She closed her lips and slowly dragged his cock between them, spreading her saliva all of his shaft. When she got to the tip, Anna jetted her tongue out to swipe at John’s pee slit, drawing a grown from the dominating man.

“You like that, big boy,” the kneel actress with a belly full of cum asked with a cheeky grin.

Not bothering to hear his response to her rhetorical question, Anna descended her mouth back on his dick. This time she swallowed most of his cock until it tapped the back of her throat, a skill she had developed over the years and years of practice. The Pitch Perfect star dragged him through her lips once again, repeating her tongue trick once again at the end.

Anna’s lips were rubbed raw at this point and her stomach was starting to turn sour from the dozen homeless men using her as a cum rag. This, paired with John having a look on his face that he wanted to cum ASAP meant that sucking him off was going to be on the quicker side. Not wasting time to give him her top notch blowjob with all the bells and whistles, Anna was only interested in using her mouth to get him off in as the quickest and most effective way possible.

Anna took him inside her oral cavity once again and had him butt up against the back of her mouth. This time, rather than withdraw, she relaxed her throat just like she had done earlier with some of the lucky men in the gloryhole blowbang. However, none of them had a cock so big so Anna had to really focus, therefore it took an extra moment but her muscles relented and she pushed forward so that now her chin was pressed against his full ball sac, her nose was buried in his thick bush of pubic hair and his cock was completely contained within her mouth and bulging down her throat.

“Oh shit! Forgot how fucking talented you are with that mouth of yours,” John complimented.

The rude man stood mouth a gap as this petite star, who couldn’t weigh more than 100 pounds soaking wet deepthroat his monster cock. She had done this in their first and only other hook-up, but she didn’t seem to be into then as much as this time. Currently, he held tightly onto the handful of hair in his fist and used it to make short jerking motions, making her lips glide over the last inch of his cock while the rest of his pole stayed soaking in her throat.

Anna was able to let him soak within her mouth and gullet for a few long moments before she started to run low on air. John looked down and watched as first her eyes started going glossy before she started to panic since his vice-like grip on her head didn’t relent. Finally after another heartbeat of savoring the feeling of his entire cock inside of her throat and the helplessness of the tiny hottie, John relaxed and Anna pulled off his dick altogether.

“Huuhhhhh….Puuuffff,” Anna chocked in fresh air, large ropey strings of drool still connecting her mouth to John’s thick cock.

Rather than be made at the man for practically choking her and making her nearly black out with his dick, Anna looked up at him with her piercing blue eyes and smiled! Anna steadied herself up on her knees once more, got another long pull of air back into her lungs and then when she had recovered from the oxygen debt she took him back down her throat all the way but this time bobbed her head on her own accord.

“Oh fuck yeah,” John groaned.

Anna felt that John was shifting to his right so she went with him and shift the 90 degrees with him, realizing now that the wall was directly at her back. John took a step forward and Anna pushed back until she felt a thud as her back pressed firmly against the wall. With his cock currently gliding fully in and out of her mouth, John continued to press forward with every bob until finally he had pushed the talented cocksucker all the way so the back of her auburn head was against the wall as well.

The actress with big swaying tits had no room left to move her head and was utterly at John’s mercy. He held his cock in her mouth until he could see her face flush red then begin to turn a bluish color. At that point he withdrew all the way and watched as the Anna coughed and spat large amounts of spit onto both his cock and onto the ground. Done with only using his cock to choke the gorgeous actress, John began to use her deep throating ability to plunge the depths of Anna’s mouth then pull out as soon as his pelvis thumped the 35 year old’s nose.

“Gllugghh…uugghhh…awwkkk,” Anna muttered and gagged as John repeated pushed in and out of her throat.

“Just like that,” John grunted, tightening his grip on the petite starlet hair.

John alternated between his original tactic of stroking the majority of his pole between Anna’s lips, which felt great. However, when he discovered how much better it felt to fuck her mouth with only short thrusts he kept with that technique. It felt roughly the same but it was the extra gurgling and gagging noises come from the tiny but talented Anna Kendrick that made it so much better.

“Choke on that dick,” John hissed, grinding his hips in short thrusts in Anna’s throat.

“Gaawwkkk,” was Anna’s only reply from being face fucked.

John let Anna surface for air after another dozen seconds of the dick sucking, but Anna only used the momentary freedom to spit the build-up of her spit back onto her dick and take in another gulp of air. Anna went to steer the sloppy dick back in her mouth, which John allowed but only after the towering man bat his heavy pole against her gorgeous face.

Though she was kneeling, her head and back pressed firmly against the wall behind her and her eyes tearing up, Anna couldn’t have felt more comfortable. Opening her mouth wide and relaxing her throat, taking John fully into her oral cavity was only getting easier, despite the fact it was an 8 inch long, 2 inch thick monster of a dick. However, Anna simply stuck her tongue as far out as it could go to even lick some of his sac while John completely fucked her gorgeous face.

“Fuck, fuck, fuck,” John swore, the need to cum grown too large.

“Cum for me,” Anna begged, going to her classic combination of mouth sucking his tip while her hand milked the rest of his large shaft.

“Let go and look up,” her former co-star demanded, taking his dick from her hand.

Anna did as the much larger man asked by sinking down further on her knees and angling her face upwards to look at him, making her face an even more inviting target. John beat his cock with a fevered rush, Anna’s copious amounts of saliva acting as a perfect lubricant. Within another handful of tugs, Anna watched as his pee slit gaped slightly before thick strands of cum came shooting out. With measured aim, John onload on the beautiful actress’ face, strands running from forehead up onto the top of her hair, several striking her nose and either running up over her eyes or down onto her cheeks. One or two stray strands went off to the sides, streaking over her ear and landing in her hair again while a final smaller few drops populated her chin and neck.

“Wow! That’s a lot on my face. Any tissues around,” Anna asked after she recovered her breath. “Or should I just scoop into my mouth?”

“Neither,” John said, pulling up his pants. “Your leaving this store and getting into the taxi with cum still all over your face and in your hair.”

“But...they have cameras. And I’ll be out in public...cum all over my very recognizable face,” Anna tried to reason as she began getting dressed.

“Sweet Anna. Have you ever known me to change my mind?” John asked, giving her tits a last squeeze before her bra and button-up shirt were slid on.

Anna once more accepted her fate, albeit with John being courteous enough to usher the men out onto the street so her pictures weren’t snapped in the sex shop. They still captured semen drenching her face and streaking her hair, but it had dried enough that it could have been confused for a lot of other things, luckily for the actress. By the time she climbed into the cab and started driving home, she wasn’t disgusted or ashamed about anything she’d done, in fact she was just plain horny and curious what the next challenge John would throw at her would be.
 
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fenderdiesel

Re: Winning At All Costs (Anna Kendrick)
« Reply #3 on: December 11, 2019, 10:13:00 AM »
A fucking legend mate!
 

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thechemist

Re: Winning At All Costs (Anna Kendrick)
« Reply #4 on: January 15, 2020, 05:20:57 PM »
Title: Winning At All Costs Part 3
Author: The Chemist
Celebrities: Anna Kendrick, John Krasinski
Codes: MF, M+F, Anal, DP, Oral, Watersport
Disclaimer: I make no money from this work of fiction. Do not read if under 18. These events did not happen, I do not know Anna, William or Michael Kendrick, John Krasinski, nor am I associated with them in any way

Summary - John’s second ‘wish’ for Anna is inviting her to a masked party and instructing her to entertain a group of 8 of her cousins, uncles, brother and father. She’s reluctant at first but ultimately consents.



KNOCK KNOCK KNOCK

When Anna Kendrik heard the rapping of knuckles at her door in the pattern she had grown used to, she shot from the bed and practically ran to answer the door. Standing on the other side of her hotel room door was none other than John Krasinski, a man that she had come to known as her master in all things. However, this time the man that most people assumed was nice and mild mannered but was in fact a sexual maniac who had successfully groomed Anna into his perfect sex slut, was not alone. Following the taller man into the room were two women, carrying a dress bag as well as several other hand bags.

“What’s all this,” Anna asked as 2 others followed John into her hotel room.

John walked over to the much shorter girl, reached down to cup the back of her head and then brought her in for a hard kiss. At one time, the 35 year old actress had a firm policy of never sleeping with a married man. However, John had crushed that rule, as well as another dozen or two things Anna swore she’d never do. Hell, even now while the Kendricks were celebrating a family reunion in her home state of Maine, John was staying in the hotel as well, coming to Anna’s room at any hour of the day or night to fuck her senseless.

Anna was so used to John being around that she never really questioned the fact that he was at the same resort as her and her family. In fact, the Office star had even been chatting with some of Anna’s cousins and uncles, and her brother and father a lot. Truthfully, she chalked it up to the fact that they were all big fans of his and his projects, plus whatever her master chose to disclose to her was his business only.

“Stylists,” John replied after pulling his tongue from her mouth. “Shelia is here to fit your dress and mask while Alisha will be dying your hair.”

“Okay,” Anna said, going with whatever the man who effective owned her free will stated. “But why?”

“The reason is because I want your identity concealed, which is why the mask and the little beauty mark they’ll be putting on your chin, the change from your light brown hair to more of a fiery red, and lastly, need to change those eye colors.” John explained.

Anna went to ask more questions but her personal stylists were too busy whisking her up in their process. She still didn’t know why her identity needed to be covered up, but she hoped it was for a public fuck. The thought of being caught, or better yet, watched and recorded, was a real turn on for the Pitch Perfect star.

“What color of eyes would you like to have?” one of the stylists asked.

“I’ll go with one of my favorite sorceresses and get purple,” Anna said after a minute’s thought.

“Odd but I think you can pull it off.”

“With those tits, Anna can pull off a lot,” the other woman added, getting a laugh from all of them.

For the next hour, Anna was transformed. Her hair was now unmistakably red, a shade that was more bright than she’d ever worn it. Her eyes went from their recognizable blue to a vibrant purple that still somehow looked natural. Her makeup was done in a familiar yet somehow different way, with the addition of a beauty mark on her chin. Her slightly wavy hair was worn loose and down over her shoulder, obstructing her ears, which were another of her more characteristic features. Laslty, a mask was fixed to her face, a type that was worn to an Eyes Wide Shut, sex party type, allowing it to hide her features while still being very sexy.

“You look ready to go,” John said, appearing an hour later. “Come.”

Anna stood and followed the older actor out of her room and down the hall until they reached the elevator. Rather than taking the lift, John strode a few extra yards before popping open the door leading into the stairwell. The resort the family reunion was in only had two floors, so after a dozen steps they arrived at their destination. However, rather than exit the stairwell, John tucked out of view in the back corner and started undoing his pants.

“Suck. And be quick about it,” John ordered.

In the blink of an eye, Anna was on her knees in front of John, reaching into his pants to help free his cock. He was still flaccid but the Pitch Perfect star was determined to fix that rubbing his head along her tongue for a few quick passes before swallowing half his member in one shot. It felt weird having a soft dick in her mouth, but after a handful of bobs with a generous amount of suction, John’s enormous 8 inch cock with thickness nearly the size of her wrist was good and hard.

Anna wasted no time once he was hard and began sucking him good and fast. Though she was truly a blowjob queen, blessed with an array of top techniques, tonight for John wasn’t about using the majority of them. Tonight in the stairwell of the Maine hotel was about getting the handsome to cum in her mouth as quickly as possible. John silently concurred, pleased that his grooming of the 35 year old actress had gone so well that she could read his mind practically.

“Gwwkkk...glllkkk...gawwkk,” Anna constantly spewed.

Anna’s wet sucking noise echoes around the concrete walls of the narrow stairwell as she sucked fast. There was no tenderness or love in the blowjob, only swift efficiency, but that was what was required. She knew John was bringing her somewhere, for some nefarious purpose and the unknown was driving her mad...and more than a little horny. How she went from hating his guts to being completely wrapped around his finger, being both his personal sex slave and pimp, helping him secure other girls was still a mystery. However, as she was on her knees, his massive cock in her mouth and constantly gliding along her lips, she stopped thinking about that and only on the blowjob.

“Holy shit,” John cooed from her intense sucking.

Though it was sounding very sloppy and wet, John was pleased to find that it appeared Anna was keeping herself rather together. Her makeup didn’t appear smeared from his angle and it didn’t look as though any of her spit had dripped down onto her wonderfully large tits. Normally he needed to rest a hand on the back of a woman’s head and dictate to them the tempo he liked being sucked at, however Anna needed no prompting. In fact, as John was pushed closer and closer to a record setting orgasm, it was better to leave his hands at his side and let the petite actress continue to do what she had in mind.

Her lips, tongue and hand stimulated every inch of his fat cock, a true feat given his immense size. However, the tiny star was up to the challenge of sucking him off to completion once more. Of course he was looking down, his green eyes looked with her violet ones as her head was a constant ball of motions, pushing forwards and back, tilting in a side-to-side motion to stimulate the base of his cock as well. Not to mention her hand a tugging blur, pulling along all sides of his dick as she literally pleasured all 8 inches at one time.

“Cum for me,” Anna begged between bobs of his dick into her throat. “Give me your jizz. Want it so badly.”

“Then fucking have it!” John bellowed.

This time John did reach down and grip tightly onto her head, almost crushing her skull as a wave of pleasure shot through him. Once again he swore and grunted into the stairwell as his cum boiled in his balls before it came spewing from his tip directly into his sex slave’s mouth. Between his iron-like grip on her head and her reluctance to spill any drop, Anna’s mouth stayed with only his bulbous head between her lips, using her tongue on the underbelly of his member to coax all the jizz from him. Stream after plentiful stream of salty semen came rushing from him, depositing into her mouth, bathing her taste buds in his flavor. Finally, once his strength on the sides of her head relented and his cock stopped shooting ropes of cum into her mouth, Anna swallowed down his large offering and made her way back to her feet.

“Good girl,” John groaned, doing back up his pants. “Now let’s go.”

Anna wiped the sides of her mouth, making sure she didn’t have cum on the sides of her lips and was rewarded with finding another droplet or two. She once again nearly gagged at the putrid taste of his semen, which was normally pleasant. Based on the fact that he was training for another action movie role, all the extra protein he was consuming was making his jizz taste like utter garbage, but still Anna was left crazing for more on a constant basis.

“This is where the magic is happening,” John stated as he and Anna came to a stop.

Looking up, Anna glanced at the door number before reaching to turn the door handle. Instantly, a connection was made and her hand pulled away from the door and she shot her gaze up to John with some of the old heat she once had for him. Not the defeated glare of a submissive slave, but the spunky, combative Anna that he broke, or mostly broke.

“Why are we at my father’s room,” Anna spat with anger.

“Because you are going to go fuck him,” John said as if it was the most normal thing in the world. “Well not just him. He’s one of them, as well as a couple of your uncles, 3 cousins I believe are in there too. Oh, and your brother.”

“John, are you fucking insane! These are my family members! I’m not just going to go through that door and fuck them,” Anna screamed at him.

“If it wasn’t for the fact that they were your family, a gangbang is run of the mill stuff for you,” John started to explain. “Besides, they don’t know that you’re their little Anna. I made sure of that. You’re not going to get knocked up and give birth to some mutant, which is where this whole taboo of fucking family members comes from. Besides, you are a great fucking lay, don’t you think all those single men in there, some who haven’t had sex in a year or two, deserve to experience such a great fuck?”

“But John...my family,” Anna complained but with a lot less venom than initially.

“Anna,” John said, stroking her vibrant red hair almost tenderly. “You’ve come so far. You resisted the gloryhole at first, then you dove right in and loved it. After all, haven’t you gone and done a few more on your own volition?”

“Well, yeah,” Anna replied, a partial smile appearing on her face.

“And wasn’t it you who gleefully helped me seduce a dozen young starlets in the past couple of months? Bending, or even breaking their will until they did whatever I asked of them?” John continued.

“It was,” Anna answered, her smile growing larger as she thought back to those occasions.

“I know that sleeping with your family seems odd, but it's just another taboo for you to crush in your wake, right?” John proposed. “Plus, I’ll count this as the second of your debts to me for cheating at that competition awhile ago.”

In the past month, John had effectively crushed Anna Kendrick’s willpower. He was actually a little surprised she responded initially with such distaste to his suggestion, although the idea of fucking cousins, a couple uncles, a brother and her own father was quite the stretch. However, it only went to show how much dominion and domination John had over the 35-year old star that it only took a little extra persuasion to have her agree to the pure taboo request.

“Okay,” Anna consented.

“Then here we go,” John said, inserting the keycard into the reader.

As they stepped inside, Anna couldn’t believe the scene in front of her. The hotel room was fairly spacious, albeit all one room. To the far side of the room was the large king-sized bed, which contained her cousins Scott and Mikey, who happened to be brothers. On the bench at the end of her bed was her perverted uncle Brian, which made perfect sense for him being present for a family orgy. Beside the bed was a three-seater sofa containing her other uncle Jerry, as well as his 2 sons Steven and Daniel. Lastly, on a right angle to the sofa, was a love seat containing the last two people she’d have wanted to see; her father William and her older brother Michael.

“Oh my God, John!” her perverted uncle Brian roared. “What a hottie!”

“My brother’s not wrong,” her normally mild-mannered uncle Jerry confirmed.

“No he’s not, dad,” Daniel said, standing.

“Not sure where you found this beauty who was willing to fuck a room full of guys, but great job John!” William, Anna’s dad complimented the movie star.

“How did you get all my male family members to agree to an orgy? Some of them are married for God’s sake,” Anna whispered to her master.

“The dark side has secrets layered upon secrets,” John left it cryptic as the rest of the actress’ family got to their feet and formed a semi-circle in the middle of the room.

Of course it was her perverted uncle Brian and his large beer belly that was the first to reach Anna. Running a hand down from his niece’s neck, his fingertip traced down her throat and between her heavenly tits, large and the perfect combination of heavy yet perky despite her thin frame and 35 years. He continued his descent over her flat stomach then hooked his finger into her panties only so he could pull them away before letting them snapback against her skin.

"Mmhmm...we are going to have fun tonight," Brian told the masked woman.

While her pervy uncle continued to roughly grope her large tits, Anna’s most sinister cousin Mikey rounded behind her. He had always made her skin crawl and stories she heard about him only justified that to Anna, but she tried to block at out as she felt his hands pull her dress up over her head and toss it aside. Now with an unblocked look at her slender yet bubbly junk in her trunk, Mikey was greeted to the sight of the rounded, soft flesh in a tiny black thong. However, it was a large round object poking out from either side of the small strand of fabric that got his attention

"Well I see someone is prepared for tonight," Mikey commented.

Pulling her thong to the side so everyone could have a good look at the three inch long black base of a toy resting over her asshole. Following his father’s example, Mikey snapped the thong back into place, this time the panties smacking the butt plug rather than skin. For added measure he cocked his hand back and gave each of her adorable ass cheeks a hearty slap. What Anna lacked in bulk she more than made up for in cuteness, and surprising roundness.

To show that she was a good sport and up to the challenge from the sadistic cousin, not only did Anna not whimper from the heavy blows but she actually wiggled her ass. Mikey indulged her what she wanted to proceeded to give her 2 more spankings, much to her delight.

"I think we can remove this from the proceedings," her kinder uncle Jerry spoke, taking Brian’s spot directly in front of Anna.

Anna felt the clasp of her bra become undone before her muscular uncle slid the garment up her arms. She noted the slackening of the jaw, a common reaction when men or women saw her tits for the first time. She immediately felt her large C cup tits squeezed in his calloused hands, gently at first before his grip tightened, before giving way as he clutched both her nipples in between his thumb and finger. He increased his pressure until the pink nipples become erect but backed off before it was painful, a grin plastered on his face.

“You have some fantastic tits,” Michael told his sister, appearing right behind her uncle.

“What every sister wants to hear from her brother,” Anna thought to herself, apparently her disguise working as her brother would never say that to her.

“Holy guacamole,” her father exclaimed as she took her top off. “Clearly natural as well.”

“Come, feel,” John told the men, a sinister grin on his face as he encouraged Anna’s own dad and brother to feel her up.

Anna stared with her disguised purple eyes into her father and brother’s face as they practically drooled while reaching out for her. Though she wanted to flinch away, rip her mask off to reveal it was her and stop all this, Anna instead calmed herself and let herself be the perfect little sex slave she was groomed to be. In fact, as her brother and father’s hands cupped and groped her perfect tits, the Pitch Perfect star got a perverse thrill, her thong dampening with each squeeze from her kin.

“I don’t mean to insult your mother William, but these are the nicest pair of tits I’ve ever felt,” William commented.

“Wait until you get your dick in her mouth,” John commented, bring a rapturous cheer from the men.

“I think the Hollywood guy has a great idea,” her massive cousin Scott suggested.

“Couldn’t agree more with the giant,” Danny, another cousin, echoed.

Anna took the hint and stepped forward into the semi-circle of men. However, before she could descend to her knees, her father caught her by the arm and stopped her. She felt her dad’s fingers hook in the waistband of her thong and pulled it down, exposing her completely bare sex and the massive plug of the dildo hanging in her ass. With one hand resting on her hips, the nearly 60 year old man closed his free hand around the monstrous butt plug currently filling his daughter's colon. He looked up and saw her mouth open wide but silently as he began pulling, but the toy was large and not coming out without a fight. Finally his strength conquered the tightness of her backdoor and the toy that was over 2 inches wide at the base popped free.

"Oh we are going to have so much fun," Anna’s brother smiled while seeing her asshole stay gaping open for several seconds.

Rather than put the toy aside or place it back in his sister, Michael stood up and spun the girl to face him. Her lips were still parted and when she felt the rubber butt plug touch them she got the hint and opened wider. The tip was only an inch thick but as her brother continued to push more of the toy inside, Anna had to open to the point of unhinging her jaw.

"How does that dirty plug taste," her pervert uncle asked, a bulge already formed in his pants. "You like the taste of your asshole?"

"Trust me, she doesn,” John commented, earning another loud round of cheers.

“My ass is yum and just a bit dirty, which is hot, but I’d rather get some flesh in me,” Anna cooed seductively, albeit in a southern drawl to disguise her voice from her family members.

Anna was on her knees as soon as her male family members allowed her to be. Wasting no time, Anna grabbed the dick closest to her and took him in her mouth. It was only after she flashed her eyes upwards with half his medium-length cock in between her lips that she realized it was the nicest of her cousins, Scott. After an energetic 30 seconds, Anna turned her head 90 degrees to stare right in front of her, swallowing down her second cock which belonged to her disgusting uncle. Despite the fact that she was always grossed out by him and his long lingering hugs and inappropriate touches over the years, Anna sucked on his cock with extra vigor, giving him a full minute before another quarter turn and taking the next cock in her throat.

It was only 5 minutes in and Anna seemed on the verge of being overrun with cock. However, as John watched his promising pupil gulping down dick after dick, she was able to keep up. It took a lot of effort but the busty girl was accomplishing the task. No one had cum yet, not by a long shot as it was much too soon for that after all, but she wasn’t overwhelmed yet, something that was truly remarkable.

“So much cock,” Anna huffed before swallowing down the next one presented to her. “I love it.”

“That’s because you’re a giant slut,” one of the men said.

“You’re damn right about that,” Anna smiled at her cousin before moving onto the next cock she could find.

There were 7 cocks to go around and, amazingly, Anna was able to give each one attention. While her mouth was always bobbing on a penis, each of her hands were also on cocks, pumping their length. After a good amount of time sucking one dick she would quickly move on so that everyone had a turn.

“Ugh!” Anna groaned as her red hair was tugged back on sharply, angling her face upward.

“Your mouth must be getting dry,” her troublesome cousin Mikey stated. “This should help.”

With that said, Mikey horked up some saliva from deep in his throat and took aim, litting the long stream of spit shoot from his mouth. With perfect aim, Anna felt a massive glob of spit landed on her tongue, practically shooting to the back of her mouth, forcing her to swallow down a partial amount of his saliva. It was a gross move, but at the same time he was right in the fact that Anna’s mouth was going slightly dry.

Her two cousins that were brothers decided to team up for their benefit next. Anna was already sucking off Mikey, who had recently spat down her throat. As Anna bobbed her way down the majority of his shaft, Mikey decided that wasn’t good enough. His brother was bending down and began to rub Anna’s bald cunt, which was dripping wet at this point. As the gorgeous actress moaned in pleasure, Mikey took advantage by grabbing the back of her head and spiking his hips forward, easily getting all 6 inches of dick into her mouth and down his masked cousin’s throat.

“Gllwwkkk...glllkkk...kkllkk,” Anna coughed and gagged as she was face fucked by the short man.

After a good 15 seconds, her face now flush and her nose reddened from the constant bouncing against his firm stomach, Mikey let Anna go. The actress immediately choked down a lungful of air but that was all she had time to do before the next family member was up, dick in hand and leading it towards her mouth, which Anna gladly accepted.

Steven, the youngest and weirdest of the cousins, was up next and decided to copy his older males. A little over-eager, the red-haired boy pulled Anna’s face into his groin, making her swallow all 7 inches of slender cock, but made her go onto hands and knees. The change in position brought several men to their knees behind Anna, one of them inserting two fingers into the depths of her wet cunt while another’s finger plunged knuckle-deep into her still gaping asshole.

“Oh my God,” Anna screamed at having all of her holes filled.

Other than the initial screech of pleasure, Anna didn’t miss a beat in continuing to please the men circled around her. While her mouth and left hand worked in tandem to give sloppy blowjobs, sometimes deep throating but usually bobbing with a generous amount of speed, her more coordinated right hand would stroke on the next closest cock. It was a true testament to her skill, that even while being finger-blasted with multiple digits in both pussy and ass, Anna was able to not only handle but thrive in sucking and jerking off her other family members.

Apparently Anna’s favorite cousin Scott was feeling like Anna’s multitasking sexual exploits earned her a reward. While his uncle was still stretching out the petite masked woman’s asshole, which was already fairly loose from the huge butt plug, the massive younger man slowed his hand thrusting. Rotating his wrist and keeping the muscles in his forearm tensed, the man filling Anna’s pussy repetitive tapped his fingers against his undercover cousin’s G-spot. Going faster and faster, this technique was only needed for less than a minute before Anna had to pull her mouth from the cock she was currently sucking, which happened to be her brother Michael, so that she could let out an ear-piercing bellow.

“Jesus Christ! Fuckkkkk!” Anna swore as she came hard.

Job done, which had brought a smile not only to Scott’s face but all the other males present, the cousin removed his fingers from Anna’s cunt. At this point the digits were not just coated in Anna’s juices, but positively dripping in them. Inspiration striking, Scott waited from Anna to finish servicing her brother then timed it right so that before Anna could get her lips around the next dick in line, Scott thrust his slathered fingers into her mouth.

“Mhmmm,” Anna moaned in delight as she sucked hard on his fat digits, drinking down all of her orgasmic juices.

“That sould have loosened her up for some actual fucking,” Anna heard her perverted uncle Brian call out from behind her.

The next moment, Anna felt a tugging on her head followed by a brief flash of pain as a powerful hand from behind her, likely her uncle, pulled her upwards. The dick in her mouth fell away as Anna got up from her knees to her feet for the first time in longer than she could recall. Of course, Brian didn’t keep her fully erect for long, a hand pushing between her shoulder blades had her bending at the hips so that she could rest her hands on the arm of the sofa and her small but bubbly ass pointed back at her uncle.

“Hope no one minds if I have the first go around,” the eldest of the men spoke.

His words were met with a series of nods or shrugs, the rest of the family giving the bulbous and rather perverted man permission to go ahead and fuck his undercover niece. Already in position behind her and his dick wet from her spit from having several go-arounds getting blown, Brian and with his erect cock in hand didn't hesitate in stuffing half his length into her snatch.

"Fuck...that’s good,” Anna moaned after finally being penetrated.

After withdrawing once, Brian slammed back in but this time with his full length. As his hips slammed against her ass, her toned cheeks rippled from the blow. Loving the view of it, Brian did so repeatedly with both hands on her tapered waist so he could pull his movie-star niece back as he speared forward.

"God, man. You’re relentless," John watched in admiration.

Anna most definitely agreed with the sadistic movie star’s assessment of her least favorite uncle’s fucking style. Brian had the size and strength of a linebacker, albeit a retired overweight one, and he wasn't shy about using it to dominate his tiny disguised niece. Over and over his thick cock, which she guessed was about the size of her wrist, slammed into her at a speed that a normal man would have cum within minutes, yet he seemed undisturbed.

Brian didn't know it but his fierce fucking was pushing the horny girl to an orgasm that he didn't think was possible. Of course, Anna was no ordinary girl and she had certainly trained her body over the last 20 years to handle all types of fucking styles, including balls-out aggression. Therefore, it wasn’t too much of a surprise to the petite actress that she felt a familiar electric sensation welling up in her suddenly, pleased that the huge man could bring her to climax so fast.

"SSHHHHHIITTTT! I'm cumming," Anna screamed, her second orgasm of the evening.

The seven other members of the Kendrick family watched on as their masked female squeezed her thighs tightly around the cock in her pussy right as Brian pulled out of her. He sensed she was a squirter only a second before and the drive to see her gush fluid was too strong. The second he pulled out of her snatch it erupted as a large stream of clear fluid jetted out and splashed on the carpet beneath.

The men practically gasped in amazement and stroked themselves, getting harder watching the innocent looking girl drench the floor from squirting. Brian slapped her on the ass for her good work before letting his fingers soak in the fluid beneath. As she stood bent over at the waist, resting against on the sofa’s arm, he flicked the fluid at her, her juices landing on her masked pretty face.

"So slutty," she heard her father’s voice sneer though very aroused.

Seeing that he had gone hard with his thrusting and that he wasn’t in the best shape in the first place, Brian backed away from the lovely masked squirter. Needing his sexual reserves to become restored before taking another turn with the large breasted woman, Brian was more than happy to have a breather as his fellow horny family members had their turn.

Luckily for Anna, there were lots more men around willing and able to take up the charge. She wasn’t aware of who it was that stepped up behind her and effortlessly slide their dick into her wet snatch, but given the slender feel of his member and the way it poked deep into her womb with each thrust, she suspected it was her creepy cousin Mikey. At her other end, she knew for sure it was her brother Michael that had appeared kneeling on the couch in front of her face.

“God, you look so familiar,” Michael commented.

Anna didn’t reply, not knowing what to tell her brother. So instead, as his hand closed around her hair to help hold her steady due to the thumping her backside was receiving from her cousin, Anna answered by cramming Michael’s dick in her mouth. Instantly her brother moaned and thrust his hips forward slightly, not that Anna needed any help in getting a cock down her throat. All while maintaining eye contact with the man who was not only her kin but her best friend, Anna set out to give him the best blowjob she could, despite the fact that her pussy was being pounded at a rapid level and that her right hand was being used to stroke another cock mere inches from the side of her face.

The Kendrick men were showing that their horniess was matched only by their ability to share. A routine was settling in nicely as it seemed that each man got 2 minutes at which ever end they chose, fucking her pussy or being sucked off, before they pulled back and another took their place. Not only was it allowing each of them to receive a high amount of pleasure, it then gave them 5 minutes to cool back down from their pending climax, meaning they were fresh when it was their turn again.

“Come on down here,” offered Daniel, the only member of the family to do jail time.

Once her uncle pulled out of her sntach after another dozen thrusts, Anna took the dick out of her mouth and looked at where the talking had come from. Sure enough, her cousin was laying on his back on the floor, his healthy sized dick standing straight up and waiting for her. His hand grabbed hers as she got to her feet, walking around his muscular body until she was at his groin. Swinging a leg over his waist, Anna squatted down until she felt his bulbous head slice through her folds and took him deep in her pussy.

“Fuck, feels so good,” Anna cooed.

Anna was allowed to build up some rhythm atop her cousin’s cock, bouncing up and down before two lines started on either side. Anna knew the routine as her hands went to the nearest cocks, stroking them off and taking 30-second turns bobbing her red-haired head along their shafts before turning to suck off the other. After their turn in her mouth, the men would walk to the back of the line so that the next family member could have their turn.

“Next up,” Daniel grunted after a few minutes of being ridden, getting a little too close to popping.

Anna finished orally servicing the dick in her face before allowing the criminal’s strong hands to push her hips up, pushing her off her cousin’s dick. She didn’t have long to go because after one side-step to her right, Anna was back straddling another man, this time her favorite uncle Jerry. She didn’t realize but just like when she blew her brother on the sofa, Anna became aware that she put more effort into pleasing the family members that she liked a whole lot more than the ones she despised. She truly was fucked up, especially since she loved when the perverted uncle and asshole cousin would fuck her hard and rithlessly, treating her like a sex puppet.

Anna wasn’t able to ride him to her full ability because both her arms were in use, hands closed around multiple dicks in order to jerk them off. However, she was able to prop herself up high on her knees so that her favorite uncle could thrust up into her pussy with reckless abandon. He wasn’t the longest or thickest she’d ever taken but his dick felt great as it routinely pistoned up into her snatch, giving her hole a nice stretch while reaching into the best areas to help her moan around the cocks in her mouth.

“Don’t be greedy, dad,” Jerry’s son said.

Anna, whose mouth was full of another family member’s cock, could only divert her purple-colored eyes in the direction of the speaker. Sure enough, the youngest of her cousins was already next in line, laying down on his back only a feet and a half away. Once more, Anna finished sucking and being fucked before she got her feet back underneath her and strode the short distance to the younger man, stepped over his waist with one leg and made her descent.

“Anyone gonna put a dick in that gaping cave she calls an asshole?” John asked the room, several men hooting that they gladly would.

“Great idea, Hollywood,” Daniel said.

Though the masked woman had already descended on his cock in her pussy, Daniel went to swiftly change that. Reaching down to fist his cock in one hand, the criminal used the other hand to scoop under her small but curvy bottom with the other. The next time Anna rode to the top of his dick, Daniel helped her up even higher so that he was free of her velvety folds. With his cock held firm, Daniel angled the slender masked woman’s hips down lower before a combination of pushing her down and lifting his hips implanted his member halfway into her colon.

“Oh Jesus,” Anna cursed as her sphincter was spread wide.

Despite the fact it was the first dick in her ass this evening, the massive butt plug that John had gotten her to shove up her bowels had done wonders. While it was going to cause her asshole to be gaped for the rest of the evening, it also ensured that her backdoor would have no problem taking a stiff cock up the dirt road.

The men in the crowd were amazed by how unfazed the big breasted masked woman was. Despite the fact that Daniel was unlubricated other than her natural pussy juices, Anna was riding the dick now in her ass with the same speed and force that she had when in her pink slit. In fact, the anal penetration seemed to make her ride harder, which not only made them all the more excited when it was their turn, but it caused her large, pillowy tits to jiggle even more with each bounce along his length.

“It’s a dirty job but someone has to do it, eh Danny?” roared Michael, Anna’s own brother.

“Hopefully not too dirty,” Daniel replied with a laugh.

All while her criminal cousin sodomized her, and her own brother teased her, Anna didn’t forget that there was a crowd of people around. Thus, as her ass constantly rode the lying man, Anna was jerking 2 cocks and even given a sloppy blowjob to one of them as well. However, the Kendrick family was a clever bunch, and another of her cousins discovered that the shift to her riding the dick in her ass opened up another on of her holes.

“Think you can handle it, babe?” Scott asked, kneeling between her outstretched legs.

“Only one way to find out, sailor,” Anna retorted with a wink.

The mammoth man smiled as he inched closer until his equally large cock was within reach of the large-breasted woman’s sex. Without another moment's delay, Scott pushed his hips forward and speared Anna with a second cock. Instantly the petite starlet cried out in utter pleasure of being filled with over 18 inches of cock simultaneously. God, she loved gangbangs, especially when it led directly to being double penetrated.

Anna’s two cousins took a minute or to to iron out the kinks but they eventually found a smoothness to their fucking. As one pushed into her, Anna felt the other backing out. Not only did it allow the men to plow into their respective hole faster, deeper and just overall better, but the grinding of their cocks against the thin membrane that separated her asshole and pussy added an extra layer of pleasure to the whole double fucking.

“Think an old man can have another go, big fella,” Anna’s father asked his nephew after another minute.

“For my favorite uncle, I think I can share,” the jovial man laughed.

Before Scott got off his knees and allowed someone else a turn with the masked lady’s sweet pussy, the large man took her hips in his huge hands. The sight was almost comical but Scott had them there for a purpose, not just for the visual. Deciding that he could open the throttle since he was set for another spell on the sidelines watching, Soctt began fucking her snatch...hard. Anna, who was not only being pressed against Daniel’s chest as he thrust up into her asshole, was now on the receiving end of the giant’s ruthless fucking deep and hard into her pussy.

“HOOOLLLLYY FUCCKKKK! AHHHHHH!” Anna screamed.

Scott couldn’t keep this sprint up for long so he gave it all he had for as long as he could then pulled out. The men gathered cheered, not sure if it was for Scott’s relentless pace or the fact that Anna had actually cum while being double stuffed. Due to her third climax of the night, Anna only became aware that her father was fucking her pussy after a length of time that she was uncertain about.

“Yes, daddy,” Anna cooed, loving how absolutely filthy it was to be enjoying this.

“Daddy, huh?” William said, a smile spreading across his face, making him pick up his ginger pace.

“I think this slut has daddy issues,” Daniel hissed from beneath her, another thrust going deep into her ass.

“After tonight I will,” Anna said with a laugh.

“Sorry uncle, but I need a break,” Daniel eventually said. “Her asshole may look loose as all hell but she’s hugging my dick tight.”

Her father had heeded his giant nephew’s actions from early and continued to fuck her pussy with a faster pace, though not nearly as ferious given the arthritis in the hips. Regardless, it was made easier since Daniel had stopped humping up into her rectum from beneath his masked daughter. After another 2 dozen thrusts, William pulled out of the redhead’s snatch before Daniel had to beg him a second time, at which time Anna was flung from the felon’s lap and onto the hotel room floor.

“Up onto the bed,” cousin Steven said to her.

Anna was helped to her feet by her hair, making her cry out and this time not in delight. Luckily the grip on her hair relaxed as her wiry cousin dragged her to the bed. Steven was first to the mattress, landing on his back with Anna coming down right on top of him. Looping an arm around her petite body, Anna and her wonderfully large tits were dragged back onto the middle of the bed before Steven stopped moving and slipped his cock into her slick cunt.

“Fuck. So good,” the wiry man exclaimed.

Anna let her younger cousin took the lead initially but his technique was hopeless. Given the fact that he was always a selfish and weird person, it came as no surprise that the lanky man would be useless with a woman. Despite the fact that she came three times already and had been getting fucked and blowing men non-stop for the past hour, Anna planted her arms on his chest and pressed herself up. She only made it halfway up before a strong hand on her back caused her arms to buckle and send her crashing back down on her cousin, tits pressed firmly against his bony chest.

“Don’t mind sharing with your dear old dad, do you son?” Brian spoke from above his masked niece.

“Would be a pleasure,” Steven replied to his father.

Anna felt her uncle’s hand still on his back as he shifted behind her until he was positioned kneeling behind her. She had the warning of his cock head rubbing along her ass crack until he zeroed in on his target and pushed forward. Not blessed with length, her horrible uncle Brian was still thick, making her asshole up for a challenge. Of course she was up for it, but Anna couldn’t help but grunt as her back door was thrust open in one swift thrust as she was once more double penetrated.

Her uncle was fat, unmarried and very much out of practice when it came to sex. However, he knew his limitations. Therefore, he started at a leisurely pace, not giving a shit if he hogged the gorgeous girl’s asshole. Slow and steady, Brian pushed his massive girth forward, spearing Anna on his short veiny cock deeply. She felt every inch slide in and out of her well used asshole, and hated herself all the more for the fact such a monster was allowed to have sex with her. However, she was too far deep down the well, so thoroughly under John’s spell that letting gross creatures like her uncle and cousin fuck her was worth it provided it appeased her master.

“Come on brother,” Jerry pipped up. “You are leaving the rest of us here with our dicks in our hands watching as you crush this poor woman.

“Fine, fine,” Brian said after leaving his cock to soak deep in her anal cavity for a few seconds before pulling out. “Loosened her butthole up for your twig dicks anyway.”

It was disturbing that Anna felt sad to have an unfilled opening in her holes, however it didn’t stay that way for long. Another of her uncles stepped up onto the bed and took the position, and within a few moments was sliding deep into her ass. Her uncle Jerry was a more balanced dick, not as wide as his older brother but a little longer, able to pierce deeper into her colon. As her cousin and favorite uncle found their stride working together to fuck her holes, the mattress rocked in front of her, letting her know that another of her family members was seeking pleasure from her mouth.

“Open up, big juggs,” her horrible uncle Brian ordered.

The two men she was fucking were holding Anna’s fit body tightly, enabling her head to be perfectly in line with her uncle’s crouch. From only a foot away, the gorgeous actress could smell the filth coming from her heinous uncle’s dick and as his hand reached around her head and began pulling her closer, the feeling she needed to retch only got worse. She doubted it was due to the fact he was just fresh from fucking her asshole. Sure, tasting a cock after it was right from your ass was never the most clean thing, but in her vast amount of experience with ass-to-mouth activity, it never was so bad. No, this was likely due to her uncle being a gross slob who likely had gone days or weeks without bathing. Hardening her resolve, Anna parted her lips and took his cock into her mouth, tasting the fresh flavor of her ass on him.

Watching such a beautiful girl with a face of an angel do something so nasty sent a surge through not only Brian, but all of the men watching except for the two men currently double fucking her. They watched her fiery red-haired head bob up and down in his lap, her tongue slathering his cock with saliva and cleaning him up. All while a shift change was happening behind her, her favorite uncle leaving her slender caboose and her brother taking up the large opening.

"Mmm," Anna moaned from around his dick, getting a strong taste her own ass.

“How’s that dick coming from your asshole taste?”

“Not quite foie gras but I’ve definitely tasted nastier asses,” Anna replied, marking her sluttiness by extending her tongue and running it along the side of the dick from root to tip.

It was every bit as nasty and naughty that she was hoping it would be. And it only added to her humiliation seeing the look of shock and amazement in the eyes of all her male family members in the room with her as continued blowing his dirty cock. She really getting off on being such a depraved little slut, letting her gross uncle fuck her in the ass and then sucking his cock clean.

Seeing the lust and hunger in the masked woman’s purple eyes, Brian ignored his own internal warning alarms as he held firmly onto the back of Anna’s head. Thrusting his hips he started fucking her mouth, pushing in until he felt his dirty cock brush against the back of her mouth before pulling back. When just the head of his cock was still in her mouth, the overweight man paused and let Anna suck on the head and swirl her tongue around the crown before pushing back in.

"Awhh...keep going," Brian demanded after another long minute of silence, apart from constantly groaning.

The gorgeous 35-year old actress didn't need the advice when it came to blowjobs so she merely smirked at her horny uncle. Anna pulled her mouth from his dick, now slick with her saliva with no more traces of her ass on it and used her hand to feverishly beat his meat. She did this so that she could use her tongue to help corral his heavy sack to bring it into her mouth all while her body was pitched back and forth from the relentless fucking befind her.

Anna took turns taking each nut into her mouth and giving it proper attention before she turned her oral affection back to something more solid. After all,she recognized the noises and lack of coordination in the large man’s movements, meaning that continuing with this quick and dirty blowjob would soon finish him. She moved half of his pole between her lips while stroking the other half. Using her free hand to massage his sack again, she could hear how much he appreciated what she was doing.

“Fuck, fuck, fuck, fuck. Here it comes,” Brian groaned, his hand tightening on her head.

Anna was thankful for the warning or else his first blast of super salty, repulsive cum could have made her gag. However, when the first spurt splashed against the roof of her mouth and dripped onto her tongue she was able to compose herself and not throw up from the horrible taste, instead swallowing it down. She did likewise with the following 4 squirts, each one less than the preceding one until her grotesque uncle was fully exhausted and moved off the bed to collapse in an armchair in the corner.

“1 down, 7 to go,” John offered his commentary.

With her uncle out of the way, the men took the chance to resume normal behavior. Luckily for Anna, both her years of copious amounts of sex and her training before coming here tonight with the massive butt plug had prepared her well. Which was good because these Kendrick men were determined to tear her anal ring apart if they had their way. Because the 7 men could take turns on her, it meant that they could go all out then take a break and back down from their pending climax, making them always be fresh.

With the constant cycling of men moving in and out of her pussy, asshole and mouth, Anna lost track of time. She lost track of a lot of things actually. For instance, she knew that she came at least once more, but it could have been 2 or 3 times. However, there was nothing quite like an urgent man’s tone and being tossed to the end of a bed to snap Anna back into reality.

“Open up,” a man urgently demanded.

Flat on her back, Anna did as she was told and parted her lips in a wide O. A dick was instantly placed on her tongue, a hand still rapidly beating the bottom several inches. Anna didn’t know what it said about her but she knew that the size, thickness and amount of small veins meant that the dick belonged to her criminal cousin Daniel. Sure enough, a quick peek up and her eyes confirmed that indeed, it was the man she presumed.

Her thoughts about her cousin’s dick in her mouth ended there as his tip started to spew the custard she had earned via her tight holes and being able to take a hard pounding despite her lithe build. His cum was saltier than her gross uncle’s, yet it lacked the slimy disgusting taste that the 60 year old man’s jizz tasted of. Therefore Anna was happy to collect his spunk in her mouth, bathing her taste buds in his thick seed before swallowing down every last drop.

“Turn,” a familiar voice instructed the large-breasted woman.

Anna didn’t question, she only acted by turning her head in the direction of the order. The masked woman’s eyes were still closed, not wanting to take a stray rope of jizz to the eye and have it burn. However, John, who was the man who had spoken, had other plans in mind. With top accuracy given the fact Anna’s open mouth was a moving target due to her own father hammering down into her pussy, John took aim and fired.

Anna was unfazed initially as a splash of warm fluid squirted into her mouth. It took her brain a second to realize that the salty, thick goo she expected was instead very watery and acidic. Opening her eyes, she was right in time to view as John’s slit on the head of his flaccid cock opened and a thin stream of pale amber fluid came flowing out in an arch, headed to her outstretched tongue and open mouth. Despite the surprise watersport, Anna was composed enough to let the tall man completely fill her mouth with his urine before she had to close her lips, taking the end of the stream onto her mouth and cheek before he stopped peeing on her.

“Swallow that down you piss guzzling whore,” John spat.

Once more, the men watched in astonishment as Anna opened her throat and swallowed the mouthful of piss without complaint. It took her 2 attempts to get it all down, but she accomplished the task the Hollywood actor gave her, even smiling in satisfaction afterwards.

“Holy fuck! He just pissed in her mouth,” Mikey commented, simply astonished.

“And she liked it,” Anna’s brother added in amazement.

“So hot. Needa cum,” Steven, the youngest of the group announced.

Having cleared a path for the slender man to get to Anna’s face, Steven stood right overtop of her as her head rested on the end of the bed. Anna only had to open her mouth and the man almost 15 years her junior did the rest. Steven was her least favorite cousin, but as his cum shot into her mouth and she eat it down just as fast as he produced it, she had to admit his cum tasted the best so far. She wasn’t sure if the fact that warm piss had been the last thing in her mouth had made the jizz taste better or not though.

If Anna thought things were going to slow down now that the cum train was in motion than she was a little premature. Instead, she was ripped up from the comfort of the mattress by her favorite cousin, Scott. Rather than being pushed back down, Anna was surprised when she was hoisted up into the air as Scott and his brother Mikey worked in tandem to lift Anna off her feet with her meat of their brother sandwich. It took her a moment to get her bearings but now she realized that her slender legs were wrapped around Scott’s muscular waist with his arms wrapped under her thighs and hands gripping her firm cheeks. Mikey was still behind her thrusting into her ass but now his hands were gripped tightly onto her womanly hips using them to both hold her suspended in the air and aid to drive inside her.

“Oh shit oh shit oh shit! I’m gonna cum,” Anna screamed as she gushed all over Scott’s dick despite cumming less than 10 minutes ago.

It was her most powerful orgasm of the night for the redhead and after she screamed loud enough to puncture both men’s eardrums her lithe body went limp. The result was that both her pussy and backdoor loosened significantly, allowing the horny men to pound into her even harder. The change in position also allowed both men to thrust inside her at the same time as they merely drop her down a foot so she took both cocks balls-deep at the same moment.

Of course, Anna wasn’t the only one deriving great pleasure from the double fucking. Having their cocks separated by only a thin barrier between the redhead’s pussy and rectum meant both men’s tools were grinding against one another. This just added to the amazing sensation of the busty girl’s holes squeezing them tightly for the past while as they fucked her at the same time. In fact both men hadn’t come since they started their tryst an hour ago and they were both well due.

“Need to fucking cum,” Mikey panted from behind the sexy woman.

“You and me both, bro,” Scott added.

They each did a few last thrusts into the skinny girl’s body before they pulled out, rolling Anna to the mattress as both their cocks flopped free of her holes. As soon as she was free of their nearly 2 feet combined of flesh, Anna promptly got off the bed, at which point she lowered herself to kneeling on the ground.

Hearing one of her cousins moaning louder than the other, Anna faced the smaller of the two brothers, Mikey. It was the right call as the large-breasted woman was just in time to see the mild-mannered Scott stroking himself. After one or two pumps with his fist, Scott took aim and shot his load towards her waiting mouth. With lips already parted and ready for his gooey reward, Anna caught every last drop of his salt load and swallowed it down gleefully. For what seemed like the umpteenth time that night, the masked actress took a cock coated thick in her ass juice back into her mouth and proceeded to enjoy the mixture of his cum and her ass on her taste buds.

“Yum,” the tiring sex pot cooed.

Unbeknown to her, the little bastard Mikey was also ready to bust a nut so he moved around to her side quickly, just in time to erupt a typhoon of cum right onto her supermodel-like face. He watched as Anna swallowed down his brother’s spunk then went to give him some post-sex head, even though his cock was straight out of her own asshole. Ready to explode, Mikey couldn’t hold out any longer and released his thick strands of cum onto her unsuspecting face. She was caught off guard as the first salty streak of semen pasted her cheek and nose before she turned to face him. Unable to direct it into her mouth, the second and third strands landed on her forehead and began running down her face with the rest of his load draining into her mouth and small dribbles onto her chin.

“I’m close too,” her brother Michael commented.

“Me as well, son,” their father William added.

“Not yet,” Anna demanded, only remembering at the last moment to disguise her voice in an accent. “I have a special place for you two.”

The two men warned the sexy masked woman to be quick about it so Anna organized them fast, getting her brother flat on his back before joining him. She turned around and sat down on his dick, yet another cock piercing her backdoor that night. Anna no longer winced as her asshole was forced open, instead launched into a dozen bounces along his shaft before settling backwards and beaconing her father forward.

“Come on boys, give it to me,” Anna purred.

“Let’s give her hell, son,” William smiled down at his son as he entered the woman’s cunt.

“Yes sir,” Michael agreed with his own grin.

Anna knew that her beloved father and brother didn’t have long to go before they came, which was why she wanted them inside her. She loved the two men and since she had already broken the taboo about fucking her family members, she figured she’d go all in and let her father fill her womb while her brother got the honors of delivering her an anl creampie.

“Harder,” Anna urged, her large tits swaying faster and faster from her father’s thrusting.

“Gonna pop if I keep going like this,” William warned his masked daughter.

“Then fill my pussy up,” Anna cooed. “You close too, aren’t you, big guy?”

“Ugh! Any second,” Michael grunted without missing a beat as his hips raised off the mattress to spear his dick up into his sister’s asshole.

“Cum for me! Give my ass and snatch your seed. Do it! Cum for me!” Anna begged, rocking her lithe body as much as her pinned position allowed.

“Awh fuck!” William howled from above the disguised actress.

“God damn! Ugh!” Michael grunted, thrusting upwards one last time.

Anna felt her families strokes grow more and more erratic until finally they pushed deep into her pussy and ass, respectively. Moments later, the talented actress felt twin streaks of cum plastering her from all angles. She didn’t know if your brother’s youthful streams fo cum painting her rectum’s walls or her father’s copious jizz strings pasting her womb felt better, so she was happy she had both simultaneously.

“Wow! Very good,” John told the disguised girl. “Ain’t that right men?”

“Yeah!”

“My thoughts exactly.”

 
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