Anna Kendrick: Winning at all Costs

BY : TheChemist
Category: Celebrities - Misc > Threesomes/Moresomes
Dragon prints: 11227
Disclaimer: This is an act of fiction. I do not know Anna Kendrick, Hailee Steinfeld, Emily Blunt or John Krasinski at all and this scenario did not actually occur. I make no money from this story.

Title: Winning at all Costs Part 5
Author: The Chemist
Characters: Anna Kendrick, Hailee Steinfeld
Codes: MF, MFF, FF, Anal, ATM, Finger, Oral, Voyeur, 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, Hailee Steinfeld nor am I associated with them in any way

Summary: Anna Kendrick thought she was done with John once she fulfilled her 3 wishes to him. However, he had recorded everything, which gave him ample blackmail material. Wanting to land a big movie role, John assigns Anna to woo the executive producer, and also to bring a friend.

***At the end of the story is a watersport/golden shower scene. If that type of thing doesn’t float your boat then you can still enjoy the main story as it’s only an addition at the very end***


Anna hadn’t been home for long. Just long enough to grab a long, well deserved shower. As she dried and stepped into some comfy clothes, she looked down and read the caller display on her phone. 

“Can’t even have my first coffee in the morning before this jerk calls,” Anna spoke allowed to her empty apartment.

“There’s my favorite cum rag,” John Krasinki’s voice sounded in her ear.

“Morning to you too,” Anna replied as she poured chocolate milk into her coffee.

“Need a favor. Wait, that didn’t sound right. Doing me a favor means we’re equals or something,” John laughed.

“What do you need, Johno?” the petite actress asked, sipping on the hot beverage.

“I’m shortlisted for a role. Really big one. Multi-pictures, cut of the profits, all that good stuff,” he explained. “Want to make my resume really pop so that’s where you come in. Or rather where the executive produce will cum in...side of you. Or on you. His choice obviously.”

“So a casting couch situation,” Anna rolled her eyes. “How very Hollywood.”

“Don’t act like you haven’t been on a few rumps on the sofa yourself,” John countered. “Or you just land big roles well into your 30s without going nude by sheer dumb luck. So don’t act all high and mighty to me.”

“Fine. Whatever. But it can’t be for another day or two,” Anna gave in without much pushing.

“You’ll do it whenever I can manage a meet,” the actor replied curtly. “Why?”

“Last night was uncle Brian’s weekly poker game. He owed some debts. I worked it off,” the Pitch Perfect star explained.

“Lots of pig roasting and DPs?” John laughed over the phone, imaging the tiny star taking several cocks at a time.

“That and double anal, the sick fucks,” Anna shared before squirming in her seat. “Still can’t sit unless leaning.”

“I’ll give you some time then. Need you in tip top shape. Millions of dollars are on the line. For me, anyway,” John reminded her. “Oh, and Anna. Bring a friend.”


“Big role, important producer, millions of dollars. That equation adds up to a threesome with two Hollywood sex kittens. So, have anyone in mind?” John asked, willing to let Anna have first choice. Of course, if she couldn’t nab anyone that he would call in a favor.

“Actually…” Anna pondered instead of telling him it was impossible. “I’ll start working on her. She was really starting to explore her sexuality last time we worked together 3 years ago.”

“Did you two ever hook up?” John asked.

“No. Our shoot schedules hardly lined up and we’ve both been balls to the wall busy since. I can definitely reach out to Hailee. I’ll get her on board for this.” Anna confirmed.

“Is that excitement I hear in your voice?” John asked smugly.

“Ugh. Of course it is. That’s how fucked up I am about this whole thing. I love being used by you. Talk about Stockholm Syndrome!” Anna cursed.

“At least you’ve accepted your fate, my dear,” John comforted. “Besides, your my top mistress! That’s an honor.”

“I’ve fallen so far,” Anna hung her head.

“And your asshole has been spread so wide. Potato, potato.” John replied. “Anyway, I’ll call back with the details. You do your part. Understood?”

“Yes, master. Talk soon.”

*    *    *

“And...cut!” the director yelled. “Great job.”

“Another cut required, sir?” the assistant asked.

After a minute of watching the playback, the actors waited anxiously, the director smiled. “Perfect. Hailee, Jeremy. You’re done for the night.”

“Awesome. Thank you so much,” Hailee Steinfeld blushed from her director’s nice words. She turned to her older co-star next. “Jeremy, did you want to get a celebratory drink…” 

“Ugh. Plans,” the older man said to the energetic actress and singer.

“Oh. Totally! No problem, of course,” Hailee replied. “I’ll just, um, see you after weekend Jer Bear!”

“Woof, that was hard to watch,” Anna Kendrcik piped up from offstage.

“Anna! Holy crap it is you!” Hailee practically shrieked in an octave that was just short of breaking glass. “I haven’t seen you since PP3 wrapped.”

“I know, right. I’ve been super busy. You’ve been super busy and according to the gossip rags, it sounds like some Brit has been getting all up in your guts for awhile now,” Anna shared as they hugged.

“Uhh...about that. Me and...He Who Shall Not Be Spoken About broke up a week ago.” Hailee shared, instantly deflating somewhat.

“Hey I’m so sorry to hear that,” Anna said, rubbing the younger girl’s shoulder. “I had no idea.”

Of course that was a lie. Anna had read the gossip and done some looking into Hailee through some mutual friends. Anna was well aware that Hailee was feeling broken hearted, and worse, was isolated as she filmed her latest project away from family and friends. Despite Hailee’s pep, she hadn't yet endeared herself to her cast or crew who were mostly a decade or two older than her. 

“So what are you doing here?” Hailee asked after they had caught up a little while longer.

“I have a meeting tonight with an EP,” Anna admitted truthfully. “And I thought…”

“Oh my God! Are you joining the family!” Hailee excitedly shrieked.

“Well...maybe. But I’m in stiff competition,” Anna replied, smiling as her former co-star fell easily into her web. 

“What can I do to help? Give advice on my interview? Put in a good word?” Hailee offered eagerly.

“Actually...I need something else from you,” Anna replied, doing a not-so-subtle job of looking the younger girl’s body up and down.

“Whoa! Are we talking, like, old-school Hollywood casting?” Hailee said with a combination of disgust and excitement. 

“I am. If, you know, you’d be interested. If not, no biggie. But doing a threesome with two prominent actresses would be a huge point in my favor,” Anna confided. “Shooting would start, like, immediately. We could even rent an apartment together.”

Another lie but Hailee didn’t have to know that.

“Oh my God! Yes! I’ll totally help,” the singer/actress replied. 

“Are you sure? This guy...he might be into some intense stuff.” Anna checked before mentally bitchslapping herself for potentially scaring the actress away.

“Trust me, I’m ready,” Hailee said with a bit of a haunted look behind her eyes. “Brits are into some kinky stuff. Where and when?”

“9pm at the Regis. Penthouse. Figured we could change, grab a bite together then head over?” Anna offered.

“Yes please!”

*    *    * 

Ryan Lambert loved his job. It was less a job and more being the money man for big film projects. However, it came with a perk. An awfully big perk. Well, and making shit tons of money from the profits. But as an executive producer for one of, if not the biggest film studio in the game for the last decade, Ryan had sway with casting. And the benefits of such were due at his door any minute now. 

He didn’t mean to become a sleazy Hollywood producer but the role was essentially thrust onto him. And by that he meant that once agents knew he had control over hirings, at least partially, they were throwing their clients at him. Some wanted no part of it, which was fine with Ryan. However, once some started hearing that it was almost exclusively the actresses who were willing to earn the roles on their backs, a lot started changing their minds. This rule only applied to actresses, but then Johnny K came to him with a proposition. A night with Anna Kendrick for the rule. When Ryan balked, only as a bluff as he was more than happy to fuck the starlet, John countered with Anna and a friend. The rest was history.

Ryan finished his drink down in the hotel bar, his third of the evening. Not enough to be drunk but his senses were definitely dulled. He found three was the perfect number of whiskeys before a good roll in the hay. Enough to numb himself downstairs without losing much pleasure. He could last longer, fuck harder hen cum like a hurricane.

Leaving the bar and approaching the front desk, he was greeted by the familiar concierge.

"Hello sir. Here's your key for room 1712. Your, um, guests have already arrived," the front desk man greeted him.

"Thank you, my good man," the 55 year old producer said, quickly snatching the card and rushing in the direction of his room.

The producer had never worked with John before so he had no idea if his promise was just bluster. However, given the front doorman’s words, Ryan grew excited. Sure, in his younger days he had participated in a handful of threesomes, but it had been too long. Even as his cock started to harden in his pants at the prospect of a threesome with Anna Kendrick, his feet kept moving in the direction of the hotel room. Before he knew it he was sliding his keycard into the lock, watching as the light turned green. Stepping inside, he was greeted to an image he wasn't expecting, not in the least.

On the bed was the woman he expected, that being Anna. She was in her glorious naked form, kneeling on the bed with her underrated long legs (given her short stature), tiny waist and extremely large tits (once again, given her petite frame) all in view. True to John’s words, the actress had brought a friend, and not just any girl. It was hard to see who it was due to the two gorgeous women kissing each other deeply, which obscured her face. It didn’t stop the producer from examining the new girl, noting an equally tapered waist, mile long legs that made Anna’s seem short in turn, and a pair of tits that were considerably smaller than Anna’s but no less enticing given how perfectly round and perky they were.

"Don't be shy, Mr Lambert," Anna said, looking back over her shoulder at her mark. 

"We don't bite," the dark-haired girl added, giving the older man her best come hither look. 

Though he didn’t have a say in her hiring 6 months ago, Ryan easily recognized the leggy dark=haired girl as Hailee Steinfeld. "Hailee! Oh my...I had no idea.”

"Ryan," Hailee said, raising from the bed and approaching the stunned producer completely in the nude. "I hope it's okay that I call you Ryan. I hope it’s okay that I tagged along with my bosom buddy."

"Given the way his eyes haven’t left your legs or tight ass, I doubt Ryan minds. Right?," Anna added.

"" Ryan stuttered, once more his eyes looking onto Hailee's pink nipples. "I suppose..."

"Great! Then let's get you out of these cumbersome clothes and show you a good time," Hailee stated.

The next 10 seconds was a maelstrom of movement. Hailee helped the producer out of his pants by tackling the belt and clasp while the man more than twice her age removed his jacket and shirt. Ryan was being towed towards the bed now, kicking off his pants as he went before being guided onto his back with an actress over a decade apart in ages on either side of his surprisingly strong body. 

"Wow Ryan, good for you," Hailee commented, her hand gliding slowly up and down his 7 inch cock.

"I can definitely work with that,” Anna agreed with her younger friend.

"Why don't you show Hailee how well you can share," Ryan spoke, having regained his composure after the surprise of seeing both Pitch Perfect stars in his hotel room.

The two girls knew exactly what he meant and had dropped down deep onto their knees so each of their gorgeous faces were hovering overtop his cock. Hailee allowed the older actress to have the first turn since it was her job on the line after all and Anna didn't hesitate to seize the chance. Opening her mouth wide, Anna easily inhaled the first half of Ryan' length before pulling her back up to the tip. 

"A real go-getter," Hailee mused as she watched the auburn-haired woman energetically bob along his length.

Hailee waited a short time until Anna slowed then she took her chance. Lowering her pretty head down lower, Hailee licked the portion of Ryan's cock not currently filling Anna's mouth. Hailee kept moving up, catching Anna's lip from time to time until she'd forced Anna off his cock so that Hailee could get her mouth on his dick.

Ryan would have been lying if he said he hadn't always dreamt what it would be like to have Hailee Steinfeld in his bed. He sadly didn’t have any casting pull when it came to the television portion of the productions, or else he may have gotten to know her already. However, fate, or John, had intervened and things worked out. But now he was enjoying himself, the feel of her pillowy lips felt great around his cock as she looked up and stared into his eyes while she slowly declined her lips until his tip poked the back of her mouth then reversed course.

"Awhhh...I've died and gone to heaven," Ryan groaned as Hailee continued.

Out of her periphery vision, Hailee saw Anna leaning back towards her. However, rather than take the cock back for herself, Anna lowered her mouth even more so her lips could capture one of the producer's nuts. It meant that Hailee had to shorten her bobs and only suck on roughly the tip and the following inch of Ryan's dick, but it allowed for Ryan to have first his right nut, then his left nut sucked on at the same time.

"Oh my God. Every man in the world would wish to be me tonight," the producer claimed, running a hand through his hair in ecstasy while Anna reclaimed his cock. 

The differences in their technique were obvious even for the most inexperienced of observers. Anna had refined her oral technique over years of trial and error until she was an efficient machine. She took her time, not going too slow or too fast, but instead that perfect speed where she used her lips and mouth to caress the lucky bastard, always being sure to use a lot of eye contact as well. Of course, the ace up her sleeve was the rare ability to deep throat, though tonight she only used that sparingly given how fucked raw her throat was from the poker game two nights back.

Conversely, Hailee was all carnal passion and youthful energy. She had learnt as a teenager that men loved blowjobs and even with much experience initially, her trick was putting as much in her mouth as possible. She had no strategy or higher thinking other than to wrap her lips around Ryan' manhood and bob her head all the way down past her gullet and into her throat, only stopping when her nose was pressed firmly against his pubic region. Her face reddened with the exertion but her eyes were screaming that she couldn't be happier pleasing her man.

"Mhmm...the way you choke down that big cock is totally impressive," Hailee complimented as Anna took all 7 inches into her mouth.

“Right back at you,” Anna replied, turning the saliva-riddled cock over to Hailee for the younger girl to swallow it fully. “God, we really should have done this earlier.” 

This time as Hailee bent down and used her tongue on the lower portion of Ryan, Anna joined her. Together they each licked one side of his penis, mirroring one another until they arrived at his purple-colored head. Anna used her tongue to glide all the way to the pee slit before allowing Hailee the same chance. However, their timing was off and they got there at the same time and immediately began another passionate makeout session while their sloppy tongues occasionally spilled from their lips and slobbered on Ryan' waiting cock. Anna was quicker to break the kiss after another handful of seconds and soon had Ryan back around her lips and completely down her throat. Ryan found it a blessing when any woman could deep throat, let alone both women in the threesome. 

"God! Can’t tell which of you is better at that," Ryan observed as Anna yet again successfully choked down his entire cock into her throat.

As Anna pulled back from his cock, she left a copious amount of her spit behind on his rod and offered it back to her Pitch Perfect co-star. Hailee took the prize without waiting, wrapping her lips back around Ryan and bobbing down half his length. However as she tried to pull back she found her way blocked by Anna's hand on the back of her head, encouraging her to take more manhood inside her mouth.

Hailee had always been proud of her ability to deep-throat, but she was suddenly hesitant to do so. With the skill being so rare, all men found it amazing when Hailee busted out her party trick of hugging their dicks with her tight throat. However, she was suddenly apprehensive now having seen Anna, a true master of deep throating, at work. Apparently Anna had seen her reserved attitude and sought to fix that. Hailee still doubted she would do it nearly as well as Anna, but the younger actress was always game for a challenge. Wiggling her head side-to-side, Hailee accomplished in fitting a little more of his dick inside her, holding him in her mouth until she needed air. This time Anna let her up but now Hailee had her own saliva dripping down onto her chin and perky tits.

"That's it, slobber all over the sexy man’s dick," Anna encouraged.

Hailee was doing exactly that. Pushing her head further down on his cock, she felt her gag reflex kick in, causing her core to flex out of habit. She pulled back but left another few thick strands of her spit behind, connecting his pole and her lips. Anna still had a hand on the back of her head so Hailee went back down, coughed up more spit as he hit the back of her throat then did it all over again.

"Oh my God," Hailee breathed in. "That is so much cock."

"It's really sexy watching you drool all over a big, thick cock," Anna agreed, kissing the other girl once more.

Of course, even as the two actresses locked lips once more and their tongues spilled into each other's mouths, they didn't forget about their guest. Hailee's hand reached down and already found her friend stroking his manhood, which was slick in their combined saliva. Therefore the leggy singer drifted lower and began gently rubbing Ryan's sensitive balls, rolling them in her fingers all while her make out session with Anna intensified. 

"Well imagine how sexy it'll be watching me fuck her," the man twice their age spoke.

With that Hailee took the cue and straightened up so she could reach the condom on the nightstand. As Anna seized the chance for some one-on-one time with her mouth and Ryan's cock, Hailee used her teeth to rip open the condom package. She could have used her fingers to do it but in her experience men got an extra thrill out of that simple move. 

"Mmm. Someone's in a hurry to get fucked," Ryan commented, drawing a giggle from the younger singer. 

Anna was in no hurry to give up the cock however. Instead, the actress with big tits continued to bob up and down on his length before sinking completely down and leaving his manhood in her throat. After a handful of seconds Anna pulled back, coating his dick in further strands of spit before she rolled the condom down his impressive shaft.

"Mind if I take the honors?" Hailee asked as Anna spat a glob of extra spit onto the sheathed cock.

"Not as long as you fuck him good," Anna replied before leaning in and giving her friend another lengthy kiss.

“I know what’s on the line, sexy,” Hailee winked.

After breaking the kiss Hailee straightened up and began the short crawl up the bed until she was over the producer's lap. Of course, the action was hastened with Ryan reaching down and grabbing her petite waist and pulling her up towards his chest, stopping when she was poised over his manhood. Hailee reached under her to clutch the condom-wrapped cock and drag it through her wet folds a few times before settling it against her twat and sitting down, allowing her body weight and gravity to do the rest.

"Awwhh! Ohh!" Hailee cooed as the first few inches disappeared into her pussy.

Hailee's hand reached down to help spread her pussy apart and help ease more of his thick cock into her, but her hand was swatted away by the more sexually active Anna. "I want to see it going inside you."

"Fuck. Me too," Ryan agreed, reaching out and pulling Anna into a kiss.

Hailee was going slow, using her weight to force herself down lower before pushing up and restarting. However, it appeared that both Anna and Ryan wanted her to ride faster as soon 4 hands were clutching her hips. Using that as instructions, Hailee began to raise up and fall down on her knees with faster repetition, which caused the remaining 2 inches to be enveloped by her cunt, taking his full length.

As the leggy girl rode the older man's dick, sounds began filling the room. At first there were Hailee's groans of 'oh yeah', ah fuck’, and the like, but soon Ryan's deeper voice was adding his grunts into the chorus as well. There was also the sound of Hailee's firm, bubbly ass smacking the producer's leg, the slapping noise echoing around the small bed chamber. 

"That's such a good girl," Anna encouraged, now on all fours with her face practically buried in Hailee's small but perky tits and her ass right next to Ryan's head. "It's so hot watching his big dick fuck your bald, pink pussy."

"Oh God," Hailee cooed as Anna began rubbing her clit all while she continued riding the entirety of the producer's shaft.

"Oh how I love this ass," the big-time producer commented, giving Anna a matching pair of spanks to her tiny ass. Settling his hand in the middle of her ass, Ryan did to Anna just as she was doing to her adorable younger friend as he began rubbing her clit. "And such a pretty pussy."

Hailee was feeling an orgasm building up already. This surprised her. Not because she didn’t like getting off, nor had trouble doing so on a regular basis. But she was being used as little other than a whore tonight, so she didn’t think cumming would be on the docket. But apparently a big dick, and her sexy friend Anna Kendrick helping her out with a clit rub, not to mention the visual of her big tits swaying about, was doing the trick for the younger woman.

“Mmm! Oh Yeah! Just like that,” Hailee howled.

Knowing she was close but needing a little more, Hailee shifted positions slightly by leaning further backwards. It took the leggy girl from kneeling into a more reclined seated position with her feet now against the mattress to help propel her not only up and down but with a swiveling motion as well. Of course, despite the commotion, Anna's magic fingers never left Hailee’s clit, continuing to flick her bean expertly.

Anna had grown distracted as the man John had set her up with began to finger her snatch, so she didn't notice right away how close her friend was to cumming. However, when Anna heard Hailee's normally musical voice go into a high-octave squealing sound, it made her look over at the dark-haired beauty. The True Grit star’s eyes were screwed shut, she was flush, and she was bouncing and gyrating with a new, almost frantic energy.

"You gonna cream all over his dick, Hailee?" Anna asked, already aware of the answer even before Hailee agreed. "Yeah? Do it!"

Presumably knowing the exact kick she needed, Anna allowed Hailee to shoo her hand away from her clit for her own, immediately going to town on herself. Anna consented and used her hand to rub Hailee's inner thigh before realizing a better use of her fingers was to latch on and give her leggy co-star’s nipples a hearty squeeze. The second Anna started to stimulate Hailee's underrated tits, the leggy girl began behaving differently. Hailee no longer screamed, instead she went almost deathly quiet. Not only that but she slowed her pace to a crawl after burying all 7 inches of the producer's dick into her wet pussy.

"Cum baby! I wanna fucking hear you scream!" Anna further encouraged.

"Yes...yesss...YESSSSS. I'm cumming!" Hailee shrieked, the volume of her voice at a shout.

Though nearly every muscle in Hailee's body was limp after her massive orgasm, she had just enough strength to hook her arms around Anna's neck, holding herself up so she could kiss her new sexual partner. Anna returned the kiss with vigor, easily overpowering the exhausted girl and cramming her tongue into Hailee's mouth. And it was at this point that the older, large-chested actress realized that Ryan was using his thumb on her asshole, and had been finger-fucking her backdoor for the last several minutes. Apparently the beating her anal ring took at her uncle’s poker night was still manifesting with a loosened and less sensitive asshole.

"I think someone wants to fuck my ass," Anna commented after breaking the kiss with Hailee. “And I definitely want my friend to watch me get fucked in the ass.”

"You got that right," the horny man said with an ear-to-ear grin.

As the producer attempted to set up and get to his knees, a hand on his chest stopped his progress. "Let the younger, eager actress desperate for the role take care of her man." Anna suggested.

"Those are fair terms," Ryan replied after thinking about it for half a second.

Anna had never slept with this man before, but she knew his type. He was probably some ex-frat guy who either liked going all-out with a doggy-style fuck, lasting a grand total of 3 minutes at best before spewing his load in or on his date. That, or he preferred doing less of the physical work, being able to last much longer. Thus, Anna was already in motion, turning her back to him as Ryan’s lap was straddled once again, this time the busty Anna in place of the leggy Hailee. She didn't want to call herself a pro when it came to sex since that made her sound like a prostitute, but at this point, if the shoe fits... 

Ryan's cock was drenched from Hailee's cumming on him but for good measure Anna added a glob of spit to make up for the lack of traditional lube available. Satisfied, Anna got quickly into position by swinging one of her impossibly long dancer legs over his waist with her bubbly tush facing him. Raising up high onto her knees, she corralled the slippery dick in her hand as she sank her body weight onto his member she felt her sphincter give way. Inch by inch she used her modest body weight to push into her bowels, the producer was smart and experienced enough to know that Anna was in complete control in this initial phase. Which was wise, because in her first descent she took him all the way into her anal opening as if it was the most natural thing in the world.

"Awh...yeah," Anna moaned.

"God! Fits like a fucking glove," Ryan grunted as she was already slowly riding back up his pole.

"Make it great," a resurrected Hailee demanded, appearing in front of Anna and giving the auburn-haired actress a kiss for motivation.

"Always," Anna confirmed with a wink, as only his tip rested in her poop chute now.

For Ryan, the whole act of sodomy was at the height of his erotic levels. The way her slender ass slowly engulfed his cock, the feel of her muscular thick ring gripping his dick in a tight but not choking manner, and even just the carnal knowledge that it was still a taboo act with a lot of girls. He also couldn't deny that the fact it was slightly degrading for the woman was a turn-on. And seeing that it was not only an A-list celebrity, but one as cute and sexy and tiny as Anna Kendrick made it all the better.

With the initial sting long gone, Anna took a moment to reorganize herself by sitting straight up with all 7 inches buried in her colon before using the springs in the bed to build momentum. It was only causing the Broadway-trained dancer to ride a few inches off his pole, but the gyration from the bouncing was what she was going for, and obviously Ryan enjoyed the effect. His amusement doubled when she reached back with both hands to spread her cheeks apart, giving the film producer a greater view of his decent-sized manhood spearing into her particularly tiny booty.

"Yes! Let me watch as you fuck her tight little ass," Hailee encouraged, surprising both of them with her crude language.

Hailee wasn't simply sitting back on her heels and viewing her former co-star getting sodomized. She understood that anal could be a painful proposition, even though Anna was showing no ill effects, not with the way she was moaning and screaming. However, Hailee sought to help her regardless. Given that Anna was riding his dick in almost perfect erect posture with her great tits bouncing proudly out in front of her, Hailee knew just what to do. Licking her lips, Hailee bent down and sucked one of the older woman’s nipples into her mouth. A guttural moan escaped from Anna's throat and one of her hands grabbed the back of Hailee's head to keep her from pulling away. It was a needless gesture as Hailee wanted to be nowhere other than buried in the deep valley created by Anna Kendrick’s pillowy tits. Flicking the nipple with her tongue, Hailee felt it start to stiffen in her mouth. Going on instincts since she lacked a lot of experience with women, Hailee covered her teeth with her lips and used them to softly massage the skin around the nipple while sucking on it, drawing another low primal moan.

"Oh Hailee, that feels so good," Anna moaned, arching her back to press her chest against Hailee's face.

When the first nipple was thoroughly wet and stiff, Hailee switched over to the other one. Not wanting to let the original nipple feel left out, the leggy singer let her fingers tweak it while her mouth worked on getting its twin ready as well. And being the dual threat that she was, Hailee used her free right hand to reach behind Anna and rub her ass, allowing her fingers to touch the throbbing cock as it pistoned in and out of Anna’s dirt road.

"God! That feels so sexy," Hailee cooed, loving how it felt when her friend was ass-fucked.

"Is it getting a little dry back there baby?" Anna asked, looking back over her shoulder at the red-faced man. "Do we need some fresh lube?"

Ryan believed he understood the bouncing girl well enough a wolfish grin appeared on his face before he had to concentrate on not blowing his load then and there from the imagery. "Yes. Always."

"Pull out," Anna ordered. "I want Hailee to taste me on your fat cock."

"Anna! I had no idea you were this naughty," Hailee cooed, releasing her lip-lock on the girl's tit.

With Hailee having moved from being right in front of her, Anna rocked forward before pitching herself completely off Ryan's cock. His manhood rocketed from the busty actress’ asshole, making Anna instantly feel empty as the producer's cock popped free and thudded onto his lower abdomen while Anna was left with an asshole hanging wide open. It would have been an odd sensation but given all the sodomy she’d been on the end of the last few months, this was essentially becoming the default state of her tushy.

"Yes! Suck! Taste!" Ryan grunted in carnal excitement.

Surprising both of her guests with her willingness for such a degrading and dirty act, Hailee sprang to motion. The singer showed no hesitation at all in picking up the throbbing member and holding it straight up as she lowered her head. Hailee had closed her eyes, not wanting to see if anything was coloring his cock considering where it had just come from, and gave both the movie producer and her former castmate what they wanted. Hailee’s fingers formed a light fist around his base, holding him up so she could extend her tongue and lick the underbelly of his cock until reaching his tip. Despite looking and behaving as innocent as an angel, this wasn't Hailee's first time taking a cock straight from ass to her mouth. Knowing what to expect, she was prepared for the slimy texture, strong taste and dirty pleasure she got from it. Hailee opened her eyes and locked gazes with the producer as she opened wide and engulfed the first several inches in her mouth in a repeated bobbing motion.

"Fuck! Suck it! Yes!" Ryan and Anna both cheered, the older man placing a hand on the back of Hailee’s head for further encouragement. 

"Slow it down. Go nice and deep," Anna added, looking over her shoulder to see the erotic and filthy scene.

Hailee hated that most of the guys she dated or hooked up with only saw her as some paradigm of virtue. They never asked her to do dirty things, expecting she wouldn’t be into it. There loss, in her opinion because Hailee was always game when it came to gaining more sexual experience. This was yet another reason she agreed so readily to Anna’s suggestion, as who better a teacher than an actress with Anna Kendrick’s lengthy reputation. Taking the advice without hesitation, Hailee continued cleaning up Ryan's truly dirty manhood with her mouth, clearly getting off with the disgraceful act. It was so nasty and naughty but that was why she was enjoying it so much, contrary to the taste in her mouth and what others would think. Remembering her other objective, Hailee began applying less suction and instead started adding more spit to his pecker, getting it ready for Anna to continue fucking him. 

"Anna! Why didn’t you ever tell me that your ass tastes so yummy," Hailee moaned being sure she transferred a lot of extra spit for Anna's benefit. 

"Now put it back in." Ryan stated.

Hailee and Anna worked as a team with the much taller Hailee getting the cock in position before Anna swiveled the hips and sat back, easily engulfing half his length in one shot into her booty. Once accustomed to the degrading and slightly off putting act of tasting her friend's asshole straight off the man's cock, it was becoming a commonplace event. Every dozen or so thrusts upwards into Anna, Ryan would have the petite woman prop herself higher so the dick fell from her well-used rectum with a wet plopping noise. Hailee would be on hand, ready and waiting, clutching the hard pole in her hand and devouring as much as she could fit in her mouth. For the portion that couldn't get between her plump lips, Hailee would extend her tongue and run it along the length of his cock, tasting Anna's filth all the while.

"Like tasting my ass on that big cock?" Anna asked with a smile as she threw herself downward, her cheeks rippling with the contact.

"So much," Hailee replied, having been struck by an idea and reaching towards Anna's hips. With a solid grip, Hailee used the strength she’d gained from working out for her new role and pushed downwards on Anna’s petite body.

“Has seeing and helping your friend get fucked up the ass stimulated any ideas of your own?” Ryan asked, reaching out to grab a handful of Hailee’s youthful ass.

“He’s doing just fine getting to fuck mine,” Anna said just loud enough so only her former castmate heard.

Hailee stopped heaving on Anna’s hips and instead used them to rock herself up high onto her knees. Giving the petite actress a kiss, Hailee eventually pulled her tongue from Anna’s mouth so she could look over the auburn-haired woman’s shoulder as she replied to Ryan.

“I think it’s time for Anna to stop hogging all the good sodomy and to share with me.”

“Making demands just because you have mile-long legs, a phenomenal body and that whole cute-sexy thing going on,” Anna joked as she lifted herself off the producer for a final time. 

The trio moved around the bed, narrowly missing becoming a tangle of limbs and falling over one another. With disaster averted, Hailee found herself kneeling in the centre of the large bed. Anna knelt beside her, certainly making out with the younger actress as the producer saddled up behind Hailee. His dick was already rock hard, so with a hand gripping himself around the base he took aim at the brunette’s crinkled starfish.

“Let me help with unlocking this door,” Anna commented.

Stepping to Hailee’s side, Anna leaned down and reached her hands out until they were on each of the leggy girl’s ass cheeks. Larger and firmer than she initially suspected, Anna got a little wetter just feeling the muscular, underrated booty in her clutches. Pulling them apart, Hailee’s anal ring not only came into better view for the man of honor, but also gave a slight gape in the tight hole.

“Just relax into it,” Anna said as Ryan’s cock made contact with her friend’s anus.

“It’s okay Anna. May look innocent but not my first anal rodeo,” Hailee replied with a wink.

While not a lie, Hailee had far less experience than Anna. That wasn’t exactly saying much since apart from some hookers and pornstars, few could match the notches on Anna Kendrick’s belt. Hailee had exactly a dozen anal experiences, all but one coming from her last boyfriend. However, the brown-haired girl wasn’t laying when she told Anna earlier that he had some weird sex kinks, including having filmed Hailee on countless times masturbating with all sorts of toys in her ass, not limited to butt plugs, dildos and anal beads.

“Oh my God! Uhhh! He’s in my ass,” Hailee groaned.

While getting a dick or any thicker toy in the caboose always stung, it was much less so when distracted apparently. Knowing tricks to help, since Anna was pulling her ass apart and making his passage through her bowels easier, Hailee reached under herself to strum on her clit. Instantly her brain became confused and then bursts of pleasure erupted in her brain. Without realizing it, not only was anal starting to feel good but her ass was swallowing more and more cock. At the point where Hailee felt her ass couldn’t possible take any more, she felt Anna’s tongue dragging across her skin from her hip and up her ribs.

“Jesus! How’s it feel taking all my dick in your plump ass?” Ryan asked as he spiked forward.

“Holy crap, Hai! You are,” Anna gawked. “Slutting it up! Makes me proud.”

“Uhhh! Ohhh! Ahhh!” was Hailee’s only reply.

Ryan’s hands replaced Anna’s in pulling apart Hailee’s ass cheeks, which made the journey of his dick balls deep in the brunette’s colon all the easier. She was already extremely tight so the thought of the full force of Hailee’s anal sphincter clamping down on his cock sounded a little painful. With her hands free, Anna took over finger duty on the younger girl’s clut while resting her beautiful face down on Hailee’s rippling booty.

“That’s it. Fuck her good.” Anna encouraged. “Your dick feel good in her 20 year old ass?”

“So fucking good,” Ryan grunted, thrustng harder but just as deep.

“And you, baby! Taking his prick so well,” Anna addressed Hailee while slipping two slender fingers into the brunette’s pussy. “All your holes filled. Bet it feels so hot and good.”

“ good,” Hailee moaned, all the nerves in her body alight.

“Look how good she is. Taking all my dick,” Ryan added, continuing to drive balls deep into Hailee.

“Flick your bean while me and the silver fox fill your holes,” Anna hissed into the brunette’s ear before giving her earlobe a lengthy suckle.

Hailee didn't have to be told twice as her hand roamed back underneath her body. Her aim was a little off on account of a fairly thick and lengthy cock plunging the depths of her rectum, but her fingertips were soon sliding overtop the bare patch of skin most girls had pubic hair. With her middle finger Hailee began swirling the digit back and forth over the exposed nubbin, which combined with her holes being double penetrated, produced a sudden uptick in the volume of her moans. 

“Oh God, oh God, oh God,” Hailee found that the screaming voice was coming from her mouth.

“Hailee, you naughty minx! Are you gonna cum?” Anna gasped in shock and admiration. 

“Just like that,” Hailee half moaned, half begged. “Mmm yes! Right there!”

Neither Anna nor Ryan knew which of them Hailee was talking to so they both continued their assault on the hole they were fucking. Anna, having been well acquainted with her own cunt, not to mention the countless women she’d fucked senseless, kept pushing in and out of Hailee’s pussy while curling her fingers on the way out so she dragged over the sensitive G-spot. For his part, Ryan continued fully sheathing his manhood in Hailee Steinfeld’s tightest of assholes, being sure to keep his strokes smooth and even. 

"Getting close?" Ryan asked, feeling his own orgasm growing more imminent.

"Almost," Hailee cooed, her own fingers a blur rubbing through her slit in order to get herself over the finish line.

For both Hailee and Ryan, the pleasure was reaching a crescendo. His hands pulling apart Hailee’s ass was helping only so much, especially now that the anal ring was quivering, giving spasms that would grip his cock like a vice. As if that wasn’t enough, the feel of Anna’s fingers rubbing the underbelly of his dick through the thin membrane that separated Hailee’s pussy and asshole was adding to his pleasure, drawing his climax nearer by each thrust.

"Oh yes! Oh God," Hailee gasped as her two lovers filled both holes simultaneously. "I'm so, so close."

While Ryan stuck to the status quo, not wanting to do anything to disrupt the one-way train Hailee was on to her orgasm, Anna was struck by inspiration. While continuing to finger-bang her cunt, the slender redhead leaned her head forward. Knowing how sensitive her own nipples were, Anna clasped her lips around one of the jiggling tits and began sucking as her tongue made lazy circles around the hardened center.

"I'm, ohhhh, I'm cumming," Hailee gasped, Anna’s fingers and mouth still working on her pussy and tits right up until she let out a strangled cry of ecstasy.

The leggy singer’s hands clutched the bed sheets until her knuckles went white as she reached her climax. That wasn’t the only bodily response Hailee had as her anus clamped down on the producer's cock like a boa constrictor trying to squeeze the life out of its prey. The added pressure was too much for the exhausted older man who let out a final grunt of pleasure as he exploded into the depths of her bowels.

"Ohhh," Hailee moaned, feeling his twitching cock spurt inside her, a sensation she loved.

Anna was suddenly struck with a truly inspirational idea. She hated the source of it, having been done to her by her uncle, but it was still sexy and nasty all at the same time and already her pussy was tingling with the thought of doing it with Miss Purity, Hailee Steinfeld. With both the leggy singer and Ryan completely spent from their simultaneous orgasms, Anna took control. Ryan's cock was already wilting, which made it even easier for it to slide right out of Hailee’s booty as Anna pushed on the leggy girl to roll her onto her back. 

"I'm going to eat the cum right from your asshole, okay sweetie?" Anna asked as she lowered herself to the bed. 

Since Ryan had only just left her asshole, Hailee’s normally tight sphincter was still gaping open. Anna smiled at the good fortune of seeing Hailee with her unnaturally long and thick legs were spread wide already, as if inviting the older actress to fulfill her dream. Using her hands to pull apart Hailee’s cheeks as much as possible, Anna dove forward with tongue out, burying the wet muscle a good inch inside her friend's ass. 

As Anna’s tongue squirmed within Hailee’s bowels, the dirtiness of the backdoor and liquefying cum that painted her bowels made a wonderful mix as it coated her taste buds while simultaneously causing the younger actress to scream in pleasure. In his younger days Ryan would have taken advantage of Anna Kendrick’s ass hanging up in the air to fuck it again, but he was completely spent so had to settle for the consolation prize of watching as the skinny woman with big tits ate his semen from the raising starlet’s he deposited it into. 

"Oh my God Anna! Your tongue feels so good inside my ass," Hailee moaned, using a hand on the back of her friend's head to help drive her deeper.

Anna didn't need the encouragement as she was very much enjoying herself. Her tongue dug deep before wagging back and forth, collecting every last drop of cum that had shot all the way up in Hailee’s bowels. The leggy girl was helping by literally pushing the thick load out of her rectum and into Anna’s waiting mouth. And even once Anna was certain she had recovered every last drop of salty baby batter, she continued wiggling her tongue back and forth over Hailee’s closing hole, much to the leggy girl's pleasure.

"Amazing. Truly, wonderfully amazing," Ryan grinned.

“Not done yet,” Anna gargled.

It was hard to perfectly understand what the large breasted woman said, but her guests understood it well enough. Crawling out from between Hailee’s phenomenal legs, Anna moved up her long body until her mouth was hovering right overtop of the brunette’s. Anna bundled her hair and held it over her shoulder as she opened her mouth and did something she rarely ever did with cum...spit. It was more like a drop as the collected sperm from deep in Hailee’s colon fell from Anna’s mouth and right into the True Grit star’s mouth, who had gleamed Anna’s intentions and parted her lips. Hailee Steinfeld caught the semen, noting what could only be described as the taste of ass with the unmistakable flavor of jizz. With a shrug, as somehow her ass made the cum taste better, Hailee gulped down the mouthful before extending her tongue for proof.

“That should help land you the role,” Hailee said with a wink up at Anna.

"I could use a shower now," Anna said after a moment of being stunned by the surprisingly dirty girl.  "Care to join Hailee?"

*    *    *

"Oh there's a party happening in here," Ryan commented, entering the bathroom 10 minutes after the girls had gone in.

Just as the hotel was fancy, so too was the bathroom. The lovely actresses were taking advantage of the luxury, utilizing both the shower and the jacuzzi tub. Having been the first to shower, Hailee was in the mostly filled bath while Anna was rinsing off in the shower. He took note of both girls before heading further into the room towards Anna.

"Naughty boy," Anna replied, finishing rinsing the suds from her curvy body. "What if we were peeing?"

"Well that's what I came in here to do," he stated, his hand wrapping onto the back of the auburn-haired girl's neck. "Kneel down."

Hailee watched from the tub the scene that was playing out in shock, but not horror. She thought Anna might protest or show some hesitancy but instead her busty castmate descended to the ground and came to rest on her knees in front of the producer's flaccid cock. Hailee continued watching as Anna's eyes never left his gaze before she leaned in so she was less than an inch from his tip and opened her mouth wide.

“Are you gonna cum again,” Hailee asked with wide-eyed wonder.

“No sweetie,” Anna said, her eyes never leaving the man’s. “He’s gonna, um, pee in my mouth.”

“Oh my God!” Hailee gawked before adding. “Do you like it? Does it taste good? Bad? Gross?”

"John asked me for a little favor. Said you really like it. You understand, Anna," the producer stated in his most serious, authoritative tone. He wasn't done there, as he turned around to face the still stunned actress in the tub. "And you, Miss Steinfeld, will watch every second because later you will be in her place. Understood?"

Hailee hoped the role was really worth it to Anna before answering. "Yes producer Lambert," the two girls both agreed at the same time.

Even if the much older man didn't tell her to observe the scene, Hailee doubted she could convince herself to look away. From the front row seat in the jacuzzi, Hailee watched as his flaccid penis came to rest on her friend's tongue while Anna looked up at him with large, expecting eyes. There were a few moments of quiet and nothing happening before suddenly Ryan's face went from strained to relaxed.

"Ahhh," Mr. Lambert sighed in relief as his bladder began to empty.

And with that mighty sigh, a thin stream of light yellow liquid shot from his purple tip. It wasn't a powerful stream, probably because Ryan still had the remains of a partial erection which obstructed a man's flow, but it was still flowing gently into Anna's mouth. After a handful of seconds the stream was cut off, allowing Anna to close her mouth, spilling some of the liquid down over her immense breasts before she actually swallowed the mouthful of piss into her belly. With a lick of her lips she parted her lips once more to receive another mouthful of urine, this time a little less as the producer decided to douse her tits in his pee while Anna once more drank the warm yellow fluid.

"Holy crap," Hailee said, mouth agape. 

"It was weird at first, almost gross, but you totally get over it," Anna confessed, standing up so she could walk to the tub and climb inside with Hailee. "Now, I kinda look forward to it at the end of my evening with un...Brian."

“Wow. Brian sounds super kinky.” Hailee stated, scooting over to make room for her friend. “Maybe I should come with you next time you see this Brian fella.”

"Did you watch and make copious notes," the producer asked, slowly circling towards the tub in Anna's wake.

Hailee blushed, thinking she knew what was coming. "I hope so."

"Have something in mind for our young, gorgeous friend?" Anna asked as she rubbed Hailee's back.

"This pretty lady," Ryan said, reaching down to gently pat Hailee on her adorable nose. "Has one more lesson to learn. Okay?"

"Mmhmm," Anna nodded her head excitedly while Hailee subverted her gaze and looked conflicted. 

"I want you to be like Anna here, sticking out your tongue but it is up to you if you swallow," the producer instructed, giving Hailee some wiggle room since it was her first time.

Under normal circumstances, Hailee Steinfeld never would have subjected herself to this degrading of a fate. However, her boyfriend, well ex-boyfriend, broke up with her largely because she wasn’t as adventurous sexually that he wanted. Therefore, the only logically thing to do, other than sleep with his best friends, was to become more slutty out of spite to that asshole. She trusted Anna already tonight and was rewarded with a great anal-induced orgasm, so why not take another leap of faith with the Pitch Pitch star? And after having seen Anna get peed on, it aroused her so she was extremely curious to see what it felt like. So as Ryan stood at the edge of the tub, Hailee knelt low before his flaccid cock which was already in his hand and pointed at her face. 

"Come show her again how to do it," Ryan said to Anna who moved to kneel beside Hailee. 

Once again Hailee watched on as her friend opened her mouth wide, extended her tongue and waited for the older man to take a piss into her mouth, only this time it was from much closer range. Hailee watched with astonishment the lack of fear or apprehension from Anna as a man literally prepared to piss inside her. 

"Get together. Press your cheeks together," Ryan instructed.

Hailee sank down lower on her knees to come to the same height as the much smaller girl beside her. Anna reached an arm out to cup Hailee's adorable face by the chin and hold her in position as specified. With only one last thing to do, Hailee closed her eyes tightly, opened her mouth and extended her tongue in a pose that mirrored Anna, although the older girl seemed much more calm and confident.

"Ready. Open your eyes, both of you, and look at me," the producer demanded, at which point a pair of blue and hazel eyes stared up at him. "Fuck. Here it comes." 

Hailee had her eyes open until she saw the first small squirt of golden fluid leave his tip, squirting a small stream into Anna's mouth for her to easily swallow it all down. However, when she saw him twist towards, Hailee instinctively closed her eyes tightly. It didn't stop her from feeling the warm splash on her flat stomach but that was just the start. The producer was building a stronger flow by the second and soon was able to produce a steady stream of thin urine that splashed onto the singer's chest, getting both her perky tits wet.

"Now open your mouth wide," Anna instructed, going from participant in the golden shower to a coach.

Hailee found that she snapped to his order and parted her lips. She reminded herself she wanted this, that this was payback. Plus, her first showering of his warm piss had gone well. Better than expected in any event. She found that the golden fluid was actually a little sensual as it bathed her skin and the smell wafting up from it wasn't revolting or even that odorous.

Now it was Anna's turn to be the voyeur and watch on as the older producer aimed his arching stream higher at her fellow Pitch Perfect star. Soon the steady current stopped pouring onto Hailee's breasts, continued up her neck before he unloaded onto her face. Most of the flow was restricted to her mouth but after a few seconds he shot a little higher and wet the rest of her face and some of her brown hair with his piss, which allowed Hailee a moment to breathe.

Though she ended up allowing most of the pee to dribble out from her downturned mouth, Hailee's curiosity got the better of her. With only a small amount welled in her mouth, Hailee shut her lips, steeled her nerve and actually gulped down roughly half a mouthful. To her shock, it turned out Anna was right when she said it wasn't that gross. Sure, it was a little foul but no worse than half the cumshots she drank down from college boys or even a bad smoothie with too much kale.

"Oh yes. Good girl." Anna said after seeing her swallow down a small mouthful.

Ryan had the common sense to spray his golden shower back towards Anna and cover her larger tits and face again to allow Hailee a few moments to get her composure after swallowing her first bit of piss ever. However, once she parted her lips Ryan was aiming back at his new muse, pissing onto her head and hair. Once her mouth was clear she obediently opened her jaw once more and the producer obliged her by filling it back up with more pee. They did this routine one more time until he was completely empty. At which point Hailee's mouth was filled by something else, this time it being Anna's tongue. Hailee recovered quickly and returned the deep kiss with her fellow Pitch Perfect actress, tasting the piss that was still residing on Anna's lips and mouth, just like Anna was probably tasting on the younger girl as well. 

"How did you like it," the piss-soaked Anna asked the kneeling girl.

"Honestly...wasn't bad," Hailee commented as she subconsciously rubbed the yellow fluid into her skin. "Girl could get used to it I think."

"That can definitely be arranged." Ryan said with a grin. "Now I'll go get dressed and allow you lovely ladies to finish cleaning...again."

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