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Anna Kendrick: Winning at all Costs	By : TheChemist Category: Celebrities - Misc > Threesomes/Moresomes Views: 14387 -:- Recommendations : 0 -:- Currently Reading : 1
Disclaimer: This is an act of fiction. I do not know Anna Kendrick, Hailee Steinfeld, Emily Blunt or John Krasinski at all and this scenario did not actually occur. I make no money from this story.

Chapter List
- 7
- 8
- 9
Title: Winning at all Costs Part 8
Author: fenderdiesel
Celebrity (Sex): Anna Kendrick
Celebrity (Non-sex): John Krasinski
Codes: MF, Anal, ATM (Dirty), Oral
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, or John Krasinski nor am I associated with them in any way. Must be 18 years of age of older to view
***This chapter was written by fenderdiesel to continue on this story. I'm not sure if he'll add more chapters in the future though I hope he does!
It had been a few weeks since Anna's last tryst with her uncle and John had been thankfully distant as well. Part of the deal she had struck with John and now her uncle, was that work came first and the last three weeks had seen Anna very busy shooting various things. With the end of her spike in work however, she lamented the undoubtedly rough fucking she would receive soon thereafter. Not that Anna disliked sex, on the contrary, Anna loved sex and had actually become quite horny over the past few weeks as it was now one of the longest dry spells of her adult life. She even truly enjoyed sex with her disgusting uncle as much as she hated to admit it. The problem was that her uncle enjoyed her ass too much. Sure, Anna loved to take a good cock up the dumper every once and awhile but her uncle seemed to be focused solely on it. Given her current dry spell and her uncles increasing affinity for minimal lube use when going in through the back door, Anna was sure the first bout of Anal was going to be a doozy.
"Oh my little Anna, how I have missed you and your sweet tits and ass." Came the creepy voice of Anna's uncle.
"Hey, Uncle Brian. Thank you, they are quite something aren't they?" Anna answered with a sweetness in her voice that betrayed her bereavement.
This was the phone call Anna had been both dreading and lusting after the past few days. Her brief reprieve was over and it was time to get back to business. Shifting her weight, Anna felt the dampness between her legs grow. Despite her best efforts, Anna knew she trully enjoyed being John's and now her dirty uncle Brian's plaything. She could have been preparing herself for the sexual proclivities her uncle would desire in an attempt to stop the discomfort and pain that would surely come during their impending tryst but, deep down, Anna craved for that pain. She had always been a fan of anal, enjoying the sting as a fleshy rod forced her rectal muscles to their breaking point. It was a matter of loss of control, she relinquished her body to her sexual partner and they could do with it as they pleased, even at the risk of hurting her in the process. Up until recently, Anna had been with men who liked to test her but would always hang back and let her maintain control of the Anal pounding, not John though, and surely not her uncle.
Both men took control and held her body hostage from her, turning a bout of rough sex into an out of body experience where Anna could let go and ride the wave of pleasure after the building pain. Where John enjoyed Anna's mental destruction just as much as her physical one, Brian focused mostly on the physical. His actions alone had a definite mental interaction with Anna, being her uncle and having his way with her was slowly scrambling a part of her brain that controlled what was right and wrong. Anna was swimming in a middle place where she knew that sex with a family member was dirty and wrong but, somehow that dirty and wrong was right for her.
"Prepare yourself for a photoshoot, you know they way I like it. Dont prep for anything else though, I hate over production...it needs to be real." Anna's uncle barked at her through the phone.
"Yes sir, what do I need for the photoshoot outfit wise?" Anna asked in a subservient tone that pushed into her throat whenever her uncle took control.
"Something....something innocent but naughty. Like what you would have worn at 16." Anna heard her uncles voice change and drip with lust as he told her what to wear, undoubtedly having a particular outfit she had worn in her teens in mind. " One word...nubile. Got it?"
Anna's chest heaved and she felt a dampness overwhelm her loins as she imagined herself in pigtails and a schoolgirls outfit...or maybe more of a Sunday dress that was conservative but she could leave it unbuttoned slightly. She began to think of a pair of shoes to wear when a bark from her uncle brought her back to reality.
"Sorry sir...yes, I will make that happen. When is this photoshoot going to take place and where?" Anna scolded herself.
"Your place, tomorrow afternoon. I will text you when I am on my way, I want you in character when I arrive." Uncle Brian spoke sternly.
"Character?" Anna asked slightly confused yet wholly aroused.
"I'll let you know in the text. See you tomorrow, my little whore" Uncle Brian nearly sang as he hung up without waiting for a response.
As Anna sat listening to the dial tone ring in her ear she couldn't help but lose herself in thought over what her uncle had in store for her tomorrow. A dainty hand slipped into her panties as she began to slowly rub her clit and imagine all the nasty possibilities.
*
A fitful night of erotic dreams and some serious horniness left Anna with a groggy disposition on her first actual day off in weeks. But under her beleaguered morning self lay a lioness ready and willing. It only took a few cups of coffee to get her engine running and for her brain to shift from being upset she was awake to replaying sexual activities she assumed she would be partaking in today with her disgusting uncle. A dampness bled into her pyjama bottoms and her nipples stood firm as stone while she sipped her warm coffee and sank into erotic daydream land.
Bree Bree Bree Bree
Anna jumped with a start as she was brought back to reality and realized the alarm she set for herself to get fully ready for her uncles arrival was bellowing in her ear. She hurriedly tossed the remainder of her drink in the sink and rushed upstairs to her bathroom to get ready.
Anna spoke quietly to herself as she lightly dabbed on her cosmetics, "nubile...light and innocent." Anna smacked her lips with her reserved lip gloss and gave a smile to the mirror as she looked at a completely G rated version of herself.
Her makeup was simple and sweet and her outfit was one that she had worn once to a family reunion when she was 17. It was a light blue sundress that had dark blue shoulder straps and a dainty little bow right at the top of her cleavage. It was tight enough to show off her bust but sat higher than the crease of her breasts and screamed innocent. The Hem of the dress came exactly three inches above her knees which was low enough for church but high enough to get boy's attention.
Although completely covered by her dress, Anna wore one of her favorite pairs of underwear, hot pink boy shorts with a little red bow at the waist and matching lacy bra. The fabric was soft and comfortable and they held the faintest scent of cut strawberries.
Looking at herself in the mirror, Anna swished her dress back and forth and giggled at the naughtiness that sat just underneath what it meant to dress up like this for her uncle. She knew today was going to be dirty and nasty and painful but she couldn't help her loins erupting with heat and anticipation. Anna had shaved her legs and armpits the night before and made sure to get each and every hair from her pussy and ass. Her uncle wanted her as smooth as possible and honestly, although she had normally opted for a small landing strip of hair in the past, she had grown to really like how she looked shaved clean.
Anna had dabbled with getting laser hair removal done so she didn't have to worry about it but would have to ask permission from John and Brian. Anna stopped and scolded herself for thinking that she needed permission but was reminded of how deep in her subservience she was when her phone dinged and she nearly ran to see if it was from Uncle Brian.
Anna opened the message quickly and read it while nibbling on the tip of a her finger anxiously. Uncle Brian was on his way and had left a bulleted list of requirements for their get together: she was 18 and a virgin(Anna snorted at that and tried to mentally prepare herself to struggle at sex, something she most certainly did not), she "needed" new headshots for her budding career and her uncle had lovingly offered to take them (Anna distinctly remembered this event happening when she was 18 or 19 and trying to get a role in hollywood but although he had offered, her mother had flat out refused him), she will address him as uncle or uncle Brian, she will wear her hair braided loosely to one side, she will be in character the whole time as her younger self and she is disgusted by him. Anna laughed out loud at the last one. That didn't require any acting at all...he was disgusting and she honestly hated him. And yet, her pussy felt like a damn quagmire as she rolled the requirements in her head and began to prepare.
It took only a few minutes and Anna was a spitting image of her younger self, the braid really sent it home and although she had a much more toned physique than she had at her younger age she still maintained a fair amount of her adolescent perkiness. Her height didn't hurt either and Anna was quite convinced that of she walked into a movie theater she would be ID'd for a rated R movie. She giggled to herself and faintly rubbed her thighs together, burning with anticipatory lust for the days events.
The buzzer to her place sounded and she knew it was her uncle. Donning her best innocent voice she spoke meekly through the intercom, "Kendrick residence, who is there?" Anna couldn't see him but she knew her uncle stopped and touched himself after her voice as he took a few seconds to press the buzzer again to speak.
"Oh, sweet little Anna, it's uncle Brian. I'm here to take your headshots." He said sing songy through the intercom. Anna shuddered at the abosilute creepiness of everything that was happening. "Your mom said you needed some and I generously offered to take them for you."
"Well, mom's not here and she didn't say anything about it to me...uncle Brian" Anna spoke innocent but deviously through the intercom, laughing a little at the frustration she knew her Uncle would be having with her.
"Well...she told me to come over and how happy you would be to have them done by your trusted uncle rather than some creepy photographer" he spat into the intercom with a heated tone that Anna knew she would pay for later.
"Hmm I don't know...do you even know how to take headshots...these are really important." Anna asked with her best teenager condescension.
"Anna of course I do, now why don't you let your loving uncle in so he isn't standing her holding all his gear on the sidewalk."
Anna could hear the anger bubbling up in his voice and felt that her playtime was over lest she suffer greatly later if she continued further, but it did feel good to have busted his balls a little. She was just acting the part he gave her.
She huffed a fine though the microphone and buzzed him in before strolling over to her front door and unlocking the dead bolt and propping it open slightly. She could hear his grunts and quiet curses as he navigated the 5 stories if stairs to her place, had she forgotten to tell him the elevator was broken? Oh well. By the time he arrived at her stoop he was drenched in sweat and pissed off, knocking the door open with a hip bump and stumbling in he dropped the boxes he had all his photography equipment in and stared furiously at his sexy niece.
"The...hupf...lift...huhhh...is broken..." He gasped at her with venom.
"Ohh yeah, the landlord told mom about that...totally forgot...my bad!" Anna cooed as she swished her dress back and forth and tossed her braid of hair from her left shoulder to her back.
"Totally forgot...okay...okay..fine." Anna saw her uncle's fury and decided it was probably best for her body that she pull it back a little.
"I'll text mom and see when she will be back, she always likes to have a say in this stuff." Anna mused as she dug her phone out of a pocket in her dress.
"No...no Anna she um...told me that she would be awhile and that we should just..uhh...get started without her. Why don't we get set up in the bedroom." Her uncle sprayed as he attempted to catch his breath and think at the same time. Anna made a face, partially in character and partially out of sadness that his acting skills were so terrible.
"The bedroom? Why there? That seems kinda...weird." Anna told him with a look of doubt that she could see gave her angry uncle a very sudden erection. Apparently she was on the right track.
"Lighting...it's all about the lighting Anna. Now grab one of these cases and help me" Brian huffed and watched as Anna rolled her deep blue eyes before grabbing a case of equipment and lugging it to her bedroom. Anna had thought about decorating or setting up her room for this and kicked herself at the missed opportunity. She had some throw pillows and some fun photos in a collage on the wall from pitch perfect but it for sure didn't resemble a young girls room.
Setting the case down with a exasperated sigh Anna hurried into her closet and rummaged for a few of her boxed stuff her mom had given her. A few teddy bears and various more adolescent items were quickly strewn about the room as her uncle huffed and lugged his fat body down the hall to her bedroom. With a grunt and a wheeze he pushed the last case into the room and gave Anna a devious grin. As he set up the equipment Anna pretended to be annoyed and impatient all the while trying to rub her thighs together and stimulate her aching sex.
"Come in Uncle Brian...this is taking FOR...EVER." Anna said disgruntled and with a touch of sass she could see made her uncles cock twitch. She had him hard and she wanted to keep pushing and prosing to see what he would do. She knew it would come back to bite her in the ass later( literally) but she kinda liked getting used and abused and a chance to fuck with her disgusting uncle was too good to pass up...even if she was about to fuck him.
"Oh don't worry..the wait will be all worth it. Now help me set up these lights." Anna giggled quietly at the seemingly self assuring statement her uncle made and huffed loudly before pretending to help set up the lights aggravating him more by messing about and acting like she couldn't do the simple task.

Anna grinned as he grumbled and sweat, fixing the many, “mistakes” she made while helping him set up the camera gear. Uncle Brian's nostrils flared and as he huffed a deep sigh Anna knew instantly that he was fed up with her little game. Her sphincter involuntarily puckered and a shiver of lust rolled from her pussy up her spine and pricked the hair up on the back of her dainty neck. Anna bit her lip and cocked a hip while she looked at her pissed uncle and as he rose from setting the final light he caught a glimpse of her and was struck motionless. His erection lifted in his already tight pants and he audibly groaned.

“Are you done yet?” Anna spoke to him as she stretched her arms out in an exaggerated sigh. The motion was more to lift her skirt hem up and pull the dress taught against her breasts than it was to cure some level of perceived boredom and by the twitch in her uncle's pants Anna was sure it had the desired effect.

“Just about..why don't you get over here and start striking poses for me.” Anna's Uncle told her while gesturing in the general vicinity of the center of the room.

Anna huffed and strolled to her designated spot with the lethargic energy of any teenager. She very lazily began to strike simple poses with no enthusiasm at all and watched as the frown on her uncles face grew more pronounced with each small movement by her. She was teasing him again and they both knew it, he had a specific scenario in mind and Anna was acting out her own little version of it that busted his balls as much as she could.

“...Anna...”

“...What?...”

“Take this seriously, this is your career..it all starts here..you want to take good photos don't you? Get a good acting job? I know these things and I know the right people. Give me a little energy and lets take some great photos.” Uncle Brian spouted off with a smug tone that made Anna want to snort in laughter. She didn't. She had a part to play and as much as she would love to ruin her uncle's gross fantasy she also really wanted to get fucked pronto and the best way to get his dick in her was to play along a little.

“You...you know the right people?” Anna asked with a tone of skepticism that made her uncle smile.

“Yup...and if you keep being a little brat..well..I don't know...maybe I'll put in a bad word and you'll be stuck doing shitty indie flicks that no one watches.” Uncle Brian mused as Anna mock gasped in outrage.

“You wouldn't!”

“I would...Just like I would tell my sister about how her daughter has been smoking marijuana." Uncle Brian smiled evilly as he held aloft a rolled up ziploc with some of the jankiest looking weed Anna had ever seen. Anna gasped in horror again, this time more realistically as she was trully offended anyone would believe she would smoke such cheap shit.
Anna moaned and stomped her tiny foot before she whispered, "...please don't, I'll be good." Giving a trully award winning smile and a sultry yet sweet pose, Anna let her uncle snap photos of her.
She swished her dress and giggled playfully as she posed playfully and seriously, running the gambit of a highschool yearbook type photoshoot. Anna could see her uncles erection tenting his pants and he quite often had to readjust himself in discomfort. Anna pretended not to see it and after nearly 10 minutes of fake photos she was ready for the next phase.
"Wow! Thanks uncle Brian..I think those will be great. While you take all this down I'm going to grab a bottle of water." Anna said with an innocence that made Brian grasp his aching crotch.
"Hold up sweetie...not quite done." Brian spoke with a sinister tone. "Those were the basic photos, now we need some...more advanced photos..to show your range." Brian mused as he gestured for Anna to get back in front of the lights.
Anna inwardly sighed, this was taking forever.
"What sort of...gulp*... Advanced photos?" Anna whispered while looking nervous.
"Well my cute niece, the kind that will get a producers attention. These are fine if you want to be in local theatre but...if you want to be a star we have to show them you want it. You do want it don't you Anna?" Brian stopped talking and raised his eyebrows at Anna while pretending to fiddle with a nearby light.
"I do...I really do..what...um...what do I have to do?" Anna laid the innocence on thick and saw her uncle give her a deeply disturbing smile. She was playing her part just the way he wanted.
"Well...that dress is a little too Sunday school for most big hollywood types. You need to seem like you know what you are doing. Why don't you unbutton it a little and show off a little of yourself. They want confidence."
Anna gulped theatrically, "it...it doesn't have buttons."
"Hmm...well maybe pull a strap down?" Brian questioned, as he strolled around the room and looked at Anna from various angles.
Anna moved one of her straps down but the bodice of the dress held it up above her breasts and rendered the act pointless.
"No..no that doesn't really do it, try the other too."
Anna pulled the other strap down nervously and held her arms in a shy posture as no real change in the dresses elevation was evident over her perky bust.
"Hmm...maybe the whole dress is the issue. I just don't think it screams, "I want to be a movie star!" do you?" Brian asked.
Anna looked down at her simple dress and shook her head no, playing along with the twisted scene.
"Have you ever watched Baywatch Anna? "
Anna was honestly taken aback by the question and broke character for a second as she screwed her face up in confusion, "uh...yeah"
Brian sneered at her, "they seem confident don't they?"
"I guess..." Anna reasoned while slowly understanding where this was going.
"I think...you need to show them that kind of confidence." Brian said with an evil look at Anna who tried her best to play innocent and naive.
"How do I do that?" Anna asked exasperated tossing her hands up and sending the straps of her dress cascading about.
"Well, do you have one of those red swimsuits?"
Anna screwed up her face into sour expression, "no...i live in Maine. I have coats."
Brian gave a wry chuckle as he rubbed his chin, "I mean...what even is a swimsuit?...if not just underwear."
Anna inwardly groaned at the low hanging fruit of her uncle's fantasy, this was like every shitty porno she had ever watched (and she had seen a lot). She rolled her eyes and got back into character, "underwear? You want me to take pictures in my underwear?"
"I want you to show your confidence Anna. Plus, most movies have skimpy costumes, don't you want the directors to know you can pull them off?"
Anna sighed and nodded, "I mean...yeah but...this feels weird. I don't do this kinda stuff usually, I go into a stall at the gym to change."
"Well Anna... you're safe with you uncle...unless you want me to tell my hollywood buddies you aren't confident enough to even have a photo taken..." Brian spoke with venom.
Trying to keep herself from sighing outwardly at how stupid this whole thing was, Anna threw a look of terror on her face and pleaded, "no no no..I'll do it I just....I'm nervous. And you are my uncle, so...it's...awkward."
"Come on Anna...I'm a professional. Now why don't you shimmy out of that cute little dress nice and slow so I can get some good action shots." Brian licked his lips and readied his camera.
Anna nodded nervously and began to unzip the back of her dress, letting the material drift down to her waist and expose her reserved but sexy bra. She heard the groan of excitement from her uncle and Anna shook her head slightly at the creepy man. She hated that he was making her do this, they both knew how this night was going to end and Anna's crotch was ablaze with anticipation. This extra song and dance did nothing for her, and as she pulled the dress slowly past her petite hips she wondered if her uncle thought she was enjoying their scene. "He probably does," Anna thought to herself, "he probably thinks his whole scene idea is getting me soaking wet and of course....my pussy is wet but because I can't stop thinking about him stretching me out not this stupid fantasy."
As Anna acted demure and self conscious as she stepped out of her dress her uncle was slowly groping himself through his pants. Barely pretending to take photos anymore he grunted for Anna to strike some poses for him.
Anna began to make small sexy movements and slowly became more erotic, exposing her cute underwear at every angle.
Anna was growing impatient and she could see that her uncle was as well, "do you think they will like this or do I need to show more confidence?"
Uncle Brian shuddered at the implication of where his fantasy was headed. "Hmm..." He pretended to ponder, "I think it is a must Anna...unless you want to end up doing indie movies that no one cares about." With a large grin, Anna's uncle simultaneously made fun of her career and set up the foundation for her to finally get her clothes off and get down to the business.
The three weeks of no sex for Anna was taking its toll, as a surge of sexual desire washed over her, she thought about her disgusting uncle forcing himself into her colon. She hated herself but her pussy ached for attention and the stupid scene was starting to make her lips moisten.
"The real show of confidence is being comfortable bearing everything, why don't you slip out of your panties and bra and let us see that beautiful body?" Uncle Brian nearly whispered as his hand massaged his length from outside his pants. Anna knew he probably fantasised about this for years and even though he has seen her naked countless times now, he is acting like it is the first.
Anna covered herself and bit her lip, "but...it's weird...I mean...I want to be in movies but...you're my...and...it's weird, only like three people have seen me naked and two of them are mom and dad."
"Exactly, I'm family. It's perfectly fine. Make sure to take them off slowly so I can get some action shots." Brian spoke with a creepiness that made Anna's stomach lurch but also ignited the hot ball of lust that sat just inside her abdomen.
With shaky hands that Anna herself couldn't tell if they were acting or real, she pulled first one strap then two down from her shoulders. Turning slightly to Brian, Anna reached behind and grasped the clasp of her dainty bra and unhooked it. With a deep breath, Anna rotated and held the cups of her bra against her chest before slowly letting it tumble down of her frame and to the floor. Her arms fell to her sides as Anna's chest heaved with a steady intake and release of a nervous woman.
Brian's lips parted and his tongue darted out to wet flesh that had suddenly gone dry at the sight of his niece's bare breasts. He had seem them so often lately but something about this time had him ready to burst. He didn't even have film in the camera he was holding but he did have a go pro set up nearby that recorded the incredible scene he had crafted.
With a nod to Anna, Brian signaled for her to keep going. Anna nodded back and reached her tiny fingers into the waistband of her panties and shimmied her hips back and forth slowly as her nubile snatch was uncovered achingly inch by inch.
Brian watched on in amazement at the tight lips if his niece and the completely shaved bare, pale skin that surrounded it. She was like a perfect little doll just for him and as the cloth of her last remaining garment passed her knees Anna slowly rose and stepped free from her underwear.
"Beautiful..." Brian whispered as Anna let the wetness of her sex glisten in the camera lights and slowly rocked her hips in a small circle, transferring her weight from foot to foot.
"Do you think they will like it, Uncle Brian?" Anna asked in the most innocent girl voice she could, seeing her uncle's cock twitch in the process. "How about this? I know I'm small but I think it looks cute." Anna turned her ass toward her uncle and bent forward, one hand reaching back and pulling a cheek away to expose her incredibly tight rosebud.
Uncle Brian just groaned as he stroked himself. As he stared into the perfect knot of Anna's rectal muscles that winked ever so slightly as they were exposed to his sight, he couldn't help but imagine that Anna's asshole was carved by God himself. It was too perfect not to be somehow divine. He wondered if Sodom was destroyed because God knew he would create such a perfect ass that alone, deserved the right to be spread open and fucked ruthlessly.
Anna held her position for a few moments, winking her rectal muscles at her uncle in beat with her racing heart. She looked back to see him in a state of catatonic shock, stroking himself and staring slackjawed at her back door. With a slow arch of her back, Anna rose from her bent position and let her hand slide back from her butt cheek, a crimson shadow of her finger tips left across her pale skin. Turning back towards her uncle, Anna brought her hands to her breasts and tugged lightly on her erect nipples.
"Now what?" Anna asked, dripping with innocent lust.
Brian had all but dropped his camera, the strap around his neck saving it from crashing to the floor. He watched as Anna's soft pink nail polishes fingers twirled and tweaked her matching color nipples as she waited for him to speak, rocking her hips back and forth seductively.
"You should come over here and suck my dick..." Brian groaned as he squeezed tightly around his erect member.
Anna smirked inwardly and then screwed up her face in disgust. "What! Eww gross... you're my uncle and I would never do that! Get out!" She spat with venom as she dropped to a crouch and picked up her spread clothing.
Brian was snapped from his dream and felt the heat rise into his face and ears. For a moment he forgot what was happening and staggered at the reaction of his little sex puppet.
Anna saw his face go from surprise to confusion and then settle into anger as he set the camera down and moved closer to her.
Brian had forgotten what he had written to Anna before he came over, he had told her that this character didn't like him and thought him creepy. His anger subsided as he realized what his sexual slave was doing and it was soon replaced with faux rage as he pushed the scene to what he really wanted.
" Listen you little bitch! I came over here to help you out and all I have gotten is attitude and ungratefulness. I can make or break your little dream and you are going to treat me like this?!" Brian bellowed as Anna cowered slightly covering her exposed body.
"You better get a whole lot better in the attitude department or I'm leaving and your little dream can go fuck itself!"
"..no...please uncle Brian... I just...I haven't ever...you know...done that." Anna squeaked out as she tried to cover her nude form with her hands and balled up dress.
"Well what a beautiful way to learn, don't you think Anna?" Brian retorted.
Anna stood silent, she opened her mouth to speak but slowly closed her mouth again.
"Anna, why don't you drop your clothes and come over here so your loving uncle can give you some teaching." He said as more of a statement than a question. "Or don't and I leave, taking all your dreams with me."
Anna could see in her uncle's eyes that he had played this scenario out many times in his head over the years. With a soft whimper Anna let the clothes fall from her hands, exposing her supple frame once more, a clear amount of lady juices glistening on her exposed sex. Anna was so much aroused by her uncle as she was the fact that she was about to fucked every which way but loose and all the while, pretending that she had no idea what she was doing. She even inwardly giggled as she knew she was going to play dumb with her uncle enough that he was going to get frustrated with her and really pound her aching and desperate body.
With her head down and in the most nervous way she could, Anna slowly walked towards her uncle. Once in arms reach sh let out a small gasp as her uncles clammy hands latched onto her perky breasts and started kneading them. It wasn't rough but it definitely wasn't nice and Anna knew her uncle was doing it for himself only. Punching her nipples between thumb and forefinger, Brian pulled Anna closer to him with a small shriek and then guided to her knees with a tug downward.
" On those knees babygirl."
Anna winced as she descended and her sensitive aroused nipples were tugged upward, making her breasts elongate slightly before her uncle released his pinching grip and her breasts snapped back to their perfect form.
"First thing a good whore does is get the cock out for her man, unbutton my trousers and let those dainty fingers coax my snake out."
Anna kept her look of fear and doubt plastered across her face as she whined under breath and brought her hands up to her uncles waistline. Unbuckling the belt and popping each button while attempting to not be an expert was hard, Anna's hands moved with deft swiftness from over a decade of training and she had to focus herself to move with adolescent sheepishness. Once fully opened up Anna reached her fingers back up to his waist and fishes then into the band of her uncle's pants and boxers before slowly pulling them down.
Anna tried to put on a face of a girl who hadn't seen countless cocks in her life and who assuredly hadn't sucked off more than she had probably kissed. The look must have been sufficient as when she exposed the shaft of Brian's cock, she saw it flex in its trapped state under the elastic of the descending garments. Her uncles crotch was hairy and greasy and as more of his thick cock was exposed Anna was treated to the sour stank of his unwashed privates.
This wasn't the first time she had smelled them and the look of disgust that cascaded across her features was genuine, however she knew no matter her protest, she was going to be sucking on the lot of it, sooner rather than later. Her uncle liked to go a few days without showering or even washing to, as he once stated to a kneeling Anna, "Seal in the flavor for you." Her freakish lack of a gag reflex was thoroughly tested that day and Anna even now knew, she was in for a rough time. But, unlike times before, Anna could play a virgin and a younger woman without her sexual acumen to betray her.
"It...it smells...sour." Anna spoke as she shriveled up her nose, pulling the remaining few inches of her uncle's clothes off his feet and looking up at him.
With a smile, Brian ran his fingers into Anna's hair and pulled her snug in his grasp, "That is the smell of a real man."
It took all of Anna's willpower not to laugh hysterically, biting her tongue both figuratively and literally as she maintained her disgusted facial expressions. "I...I've never done this before...will it hurt?"
Brian looked down into Anna's innocent face and shuddered, his dick twitching and leg muscles flexing as he reacted to the quiet words of his favorite fuck toy. She had been the object of his desires for decades and now his sick fantasies were finally coming to fruition. It took a lot of force to keep from spewing a hot load all over his niece's face.
He had been saving this load for a few weeks now, letting it ferment in his balls as he turned his already terrible diet up to 11 to ensure his load's rancid flavor. It would be an absolute terrible waste to let it spill out onto her features so early and have Anna miss an opportunity to swallow every last disgusting drop. He had to pull his mind from the thought of his thick cream filling her whimpering mouth as he coated her taste buds with thick man milk. He was desperately on the cusp of premature ejaculation. With a heavy dollop of precum dangling from his bellend, Brian took a deep breath and squeezed his aching cock, choking any flow that wished to escape.
"Only...fuck...only if you're a bad girl Anna." Brian grunted out as he squeezed the base of his member like a vice. With a growl he pulled Anna's hair and brought her face closer to the twitching head of her uncle's leaking cock. "Now be a good girl and lick the head like a lollipop."
Anna winced a little as her hair was pulled taught but had been at the mercy of many a rough fuck over the years and quickly let her head go with it rather than fight against it. Mere inches away from the pulsing rod, Anna could feel the hot sweaty musk billowing from her uncles crotch. Maybe making him do all that work with the luggage was a bad idea she mused as the smell sent her stomach tumbling. His body odor mixed with what could only be described as rotten cheese and as the thick goop of precum slowly trickled from his tip, Anna extended her tongue between her soft lips and closed her eyes.
"Ooooohhhh...fuuuu...good girl Anna..."
Brian's head tilted back as Anna's wet and warm tongue gave a long dragging lick from his upper shaft to the tip of his cock, gathering a series of cascading flavors across her taste buds. As Brian looked back down into the scrunched face of his beautiful niece he watched as her eyes opened to meet his and leaned her face away from his prick. Nestled on the pink muscle in Anna's dainty mouth was a slurry of mixed goo. The off-white and nearly clear of his precum and the tinged yellow globules of smegma, he had let grow along the ring of his cock, danced across the receptors of Anna's now overwhelmed sense of taste. Brian watched as she retched slightly but kept her mouth open so he could see her tongue before she furrowed her brow and closed her lips followed by an exaggerated swallow.
Anna used every ounce of her bodily control to maintain her composure while swallowing the thick nastiness from her uncle's cock. It was rancid and made her gag as it went down, the taste seeming to permeate into other senses like a virus. She couldn't help but shiver in disgust. But Anna had a character to play, so she looked her uncle in the eyes and leaned back forward, taking the head of his cock in her mouth and sucking deeply while swirling her tongue around his head. The smegma came off in globs and nestled across her taste buds, Anna swallowed hard and fast in an attempt to remove the terrible taste. With a loud pop she pulled her uncles twitching head free from her mouth, "like that Uncle Brian? Or do I need to suck harder?"
A shiver ran through Brian's whole body and a gush of precum dribbled out of his cock head. Anna didn't miss a beat, leaning forward and ducking her head lower so she could look her uncle in the eyes as the globule of salty prejizz dropped onto her tongue. The repugnant brine made Anna sick to her stomach but she kept her cute little face poised in place and dutifully swallowed.
Anna decided that her innocent act would have to take a back seat as she got down to business, the sooner she got her uncle off the sooner he would get to fucking her. Not ever her first choice and honestly if she thought about it, she would take any other guy in the world right now but her clit ached for attention and as she nestled her lips around his sour meat again she felt the familiar palpitations of her anal ring as it anticipated its eventual spearing. Pulling from her lofty bag of oral tricks Anna pressed herself forward until Brian's head hit the back of her mouth and then gagged slightly before pushing him into her gripping throat. With a soft hum and swallowing esophagus she began to bob slowly on her uncle's cock while maintaining a truly knee buckling level of suction. The taste was still incredibly off putting but Anna put that into the back of her mind and drifted a deft hand to her throbbing slit, erupting in a wave of heated pleasure as she stroked into her folds.
Brian's noises were undefinable as he was overtaken by pleasure, not just the physical act of receiving a world class blowjob from his adorable niece but the added bonus of having her play a character that stroked at the inner demons he had been suppressing for so long. He didn't care that Anna had abandoned the little innocent girl act for the real whore that she was, he just reveled in the lighting like surges of pure bliss that shot up his spine and clouded his senses. The suction alone was pulling him dangerously close to an unwanted premature release but the little humming and eye contact sent him careening toward his climax like a runaway train. He knew it was a matter of time before he erupted two weeks of pent up cum into his little niece's throat and he needed to think quickly. He was too far gone to pull himself back form the brink but he could still have his end goals for the day come to reality if he calmed down and took back control. Letting Anna bob and suckle on him fiercely, Brian timed her movements and pulled his hips back before slamming them back forward when Anna wasn't expecting it, lodging his cock deep into her throat and making her nose slap his pelvic bone. Anna retched and coughed as the thick phallus collided with her tonsils before falling back with watering eyes onto her haunches, gasping for air and blinking away her tears.
“What the fu...” Anna whimpered as she saw her uncle stroking himself furiously and stepping past her shocked body. With a deep growl Brian bounded towards the desk on the far end of Anna's bedroom, looking for something as he beat his cock with wild abandon. The surges of a near painful climax clouded his vision as Brian searched high and low for a receptacle that would fit his needs. Finally his eyes fell upon a colorful object and a wicked smile shown across the sweaty maw of Anna's ferocious uncle. Grasping the handle of the small Troll's sippy cup, a wrap gift that Anna had received as a joke after her most recent venture into the animated role of Poppy. The cup was hot pink and had the image of the character voiced by Anna rubbing her jeweled belly with a voice bubble saying a very satisfied, “Yummy.” Tearing the cap off and throwing it with a grunt, Anna watched as her uncle lowered the mouth of the cup to his cock, a blur of his hand beating the cum from it. With a wild roar she watched as Brian erupted a torrent of thick jism that splashed and began to fill the children's cup. Anna absentmindedly stroked her clit as she lay on her ass, watching the spectacle with unsure eyes.
With a few final full body spasms the eruption was over and the animal was sated, Brian chuckled as he scraped his still erect cock against the rim of the Poppy cup. “For Later,” he gasped as he set the cup down on the desk and resumed a light stroking of his now sensitive penis. Looking down at his naked niece, teary eyed and with droplets of her own spit painting her perky breasts he couldn't help but moan. He watched her for a few moments as she ran her tiny fingers with their pink nail polish through her engorged folds.
“Up.” It was a simple command said forcefully and before Anna could untangle her legs and get herself into a standing position Brian had crossed the short distance to her and snatched her painfully by her hair, tugging her up with a pained yelp.
“Fuck..OW!” Anna spat as she shook from her uncles grasp, breasts jiggling magnificently in the process.
“When I tell you something you do it...now,” Brian grabbed a rough handful of Anna's breast with his free hand, kneading harshly the soft flesh and feeling the hardness of her erect nipple. “That was a good start but...those Hollywood types want something real special from their little actresses. A show of how...willing..they are going to be to get the job done.” As Brian spoke he brought Anna's left nipple in between his thumb and forefinger and began to rotate and twist it, eliciting a mewling from his small niece.
“Ow...grrr...What?...What else do I have to do..ooohh ow ow ow...that hurts uncle Brian.” Anna whimpered as her nipple was pulled and twisted with a sharp ferocity. Brian then shoved her backwards onto the bed with chuckle.
“You have to give up that tight little butthole to your loving uncle Anna...thats what you have to do and you are going to be a very good girl and do it nice and rough so I know you can take it.”
Anna, despite her years of anal experience felt a fear she hadn't since the first time she ever took it up the pooper, her body clamping down like a vice and her stomach turning in knots. Betraying her swirling brain as it fell deeply into the sick world her uncle had created for her, Anna's cunt gushed like a river as her body knew what was coming and desperately craved the painful treatment of her tender holes.
“I..I haven't ever done that Uncle Brian...” Anna lied with a quiver in her voice that was as close to real as it could get.
“I know baby girl..thats why I want to teach you, so you are ready for Hollywood.” Brian said through clenched teeth as he squeezed his throbbing organ, dripping lewdly with a thick glob of cum. “On your belly, like the little whore you are...”
Anna moved with fearful speed and soon was laying with her feet on the ground and her belly and breasts pressed into her soft comforter. Feeling the warming presence of a sweaty body behind her Anna felt the calloused hands of her uncle spread her tiny cheeks before a hard slap sent a jolt of pain up her spine. Anna shrieked, caught off guard by the hard slap and moaned as a large thumb probed at her taught rectal opening.
“So tight, good girl.” Brian whisper moaned as he ran his non occupied hand over her sensitive starfish, “Might need to shut you up so I can properly break this in...” Brian mused to himself as he looked around him, smiling as he leaned down and picked up Anna's soiled panties. Not before he took a large sniff of her lady juice stained undergarments, Brian pressed the wadded up material in front of Anna's mouth and with a small amount of pressure forced them between her teeth. Anna gave a noise of surprise and looked over her shoulder so her uncle could see the image of her stuffed mouth with bits of lace and fabric poking from between her lips, giving Brian a look of fear she knew would set him into a fury.
“Wouldn't want those talented vocal chords waking up the neighbors would we?” Brian groaned as he let loose another harsh slap that served to make Anna shriek into her gag. Satisfied with the muffling of the underwear, Brian gave Anna four more quick smacks to the ass, leaving large red hand prints across her pale cheeks and making her weep and moan as she kicked her legs.
“shh..Baby girl...your gonna want to save the kicking and screaming for when I spread that tight little ass open and fuck it like it deserves.”
Anna took a deep breath and tried to steady her heightened nerves, calming her muscles and attempting to relax her anal muscles for the assuredly painful intrusion she was about to endure. A wave of anticipatory lady juices seeped form her already soaking slit and began to drip down her trembling legs. She struggled to focus as the heat and sweat from her uncle's core pressed against her lower back and the slick head of his thick dick rummaged down her back entrance. Smearing the sticky jizz across the crinkled starfish of his niece, Brian moaned one last time as he pressed his body weight forward using his girth to help drive his member into the vice like jaws of Anna's ass.
The pressure built and quickly went from uncomfortable to downright painful and then soon, unbearable. Anna screamed into her gag and wiggled her legs in a useless attempt at dislodging the hot burning intrusion from her spreading anal passage. As Brian let his full weight drape across Anna's rump he felt the muscles of her ring spasm and like a balancing slack liner he remained up above his niece's bubbly booty only for a moment before the muscles finally gave way. Sinking nearly two inches downward, Brian felt Anna's butt muscles clench and release and then spasm horrifically as they lost their fight against the foreign intruder. There was a beat of silence before the banshee's wail of Anna cut through the room and Brian was nearly bucked off his bootylicous perch.
Anna wailed with all of the air in her lungs as it felt as if her uncle's thick cock had forced it all out of her, the searing pain of having her ass forced open with near zero lubrication made her see stars and it felt as if her ears had been stuffed with cotton. The jolt of muscles giving way had made it so the thick intruder had nestled a good two inches into her back door and her entire body was clenching to force it back out, however the sheer weight of her uncle was too much for Anna to even budge with her flaring and rippling muscles. Brian gave Anna no quarter as he began to buck his waist and roll his hips, driving himself deeper into the forbidden passage of Anna's dirty bowels.
Bile rose in Anna's mouth, eyes rolling backwards in their socket as the intrusion blotted out her existence in reality. The white hot pain of her ass being stretched to the breaking point remained for what seemed like an eternity before a tinge of pleasure faded in from the background. Anna saw it on the corner of her glared vision, a faint figure dancing on the periphery of her mind, coming slowly closer and making her screams become more erotic than hoarse as her uncle picked up his spearing pace.
Brian had managed to get about 3/4's of his cock up Anna's bowels before he really started thrusting and driving the piston in and out of her gripping chasm. He reveled in the tightness and couldn't' take his eyes off the rippling back muscles of his dominated niece, her knuckles white as she held a deathgrip of comforter in each hand. At first it was just sharp jabs with his cock and muffled shrieks over and over but as time faded into sexual oblivion the thrusts became more deep and powerful and the shrieks turned to low guttural moans. Before Brian knew it, Anna was bucking her hips backwards to meet the powerful thrusts of his breakneck ass fucking pace.
Anna was running on autopilot, years of anal experience taking the reigns as her mind checked out. She was swimming in a pool of confused ecstasy. The pain was unbearable and yet it unlocked a section of her brain that she had always danced around the edge of. The feeling of helplessness and pain shattering the crafted confidence she had in her sexual goddess status. The powerful voice in her head that she had cultivated over the years was reduced from untouchable sexual prowess to a soft chanting of, “This is what you deserve you dirty slut.” The phrase seemed to be punctuated with a surge of pain as the flaming poker of a cock in her ass dug deeper into her colon before flowering in a cascade of deeply disturbing pleasure. The pain unlocking an untapped source of orgasmic pleasure, a avast ocean of unused potential for her body to draw from.
She didn't realize that her head had been pulled backward by her hair until a splat of foul taste slapped across her dry tongue. Flashes of her uncle spitting wads of snot into her mouth skipped across her mind, he said something to her about her mouth being dry and needing his help. She closed her lips and found she was in fact possessing a very dry mouth, happily swallowing the offered spit as unconsciousness tickled her senses.
Brian grunted as his whore of a niece mewled like a farm animal, low groans and panting backing the sharp slaps of skin on skin as he jack-hammered his dick in and out of her destroyed shit chute. Using her hair like the reigns of a horse, Brian reared her head back and lifted her wobbling perky tits up from the sweaty comforter. Slapping and pinching the now exposed breasts, Brian roared with pleasure as he neared his second orgasm of the evening. Gripping Anna's waist and hoisted up further onto the bed, Brian was able to get her knees partially under her, jutting her ass backwards and pressing her stomach and chest across her now pinned thighs beneath her. The grunts being fucked out of Anna's throat were now much more hoarse as the air was forced out of her lungs with every crashing pelvic drop of her uncle as he tried to put his cock into her stomach through her colon.
With a breathless whimper, Anna spoke for the first time in the past 20 minutes of fucking, “Ch..ch..ch..choke...mmmme....choke me.” It was more of desperate plea than anything else and Brian did not hesitate for a second as he wrapped his meaty paw around her thin neck and squeezed. Anna in her brain dead stupor got a limp hand between her sopping wet thighs and began to pinch and flick her needy clit. Spirals of pleasure sent Anna into convulsions as her body simultaneously orgasmed and had a critical melt down.
If her airway hadn't been shut off by a fat and sweaty palm around her neck the wail of pure eternal bliss would have cracked the windows, it came out as silent scream instead. Anna arched her back as her hand slapped and thrashed her clit like a madwomen, lady cum spraying all over her bed and brian's ass and legs.
“Oh JESUS FUCK!” Brian bellowed as Anna's ass muscles sucked him in and squeezed him for all their worth. If he didn't know better, Brian would have thought Anna had a body builder in her ass that was holding his cock in a choke hold. Letting go of his nieces neck and hearing her gasp and moan passionately he tried to pull himself back before bucking forward again, the pain and pleasure of the vice he was stuck in sent him over the edge and as he collapsed onto Anna's back he let out a whimpering scream. Anna felt the blanket of hairy flesh press over her frame as the deep pressure of thick cum filled her bowels and made her stomach cramp terribly. The pair lay there for a few moments, both in various stages of bliss and pain as Anna fought the lack of breath and the cramps, her ass sore and inflamed. Brian moaned low as his extremely sensitive cock was still held firmly in Anna's vice like ass, her throbbing heartbeat making him wince as it beat like wardrums around his member.
Slowly Brian fell back off his niece and panted for breath, staring at the gaped hole that not long ago had been no more open then the tip of a needle, he was sure he could fit his fist in her if he wasn't so exhausted. He watched as her ring puckered and released, fighting over and over the need to grip something, fighting to regain their former shape. As the gape began to shrink and Anna lay motionless save for deep heavy breaths, Brian saw the off white sludge of his seed peaking from the depths of Anna's rectum and working back out. With a heavy sigh he lifted himself from his ass and walked to her desk across the room. Anna had her head tilted to one side and her glazed over eyes caught the movement across the room, she barely moved to look at him but his smile told her what was happening next. She didn't care, as long as she didn't move, he could do whatever he wanted to her now.
Anna felt the rim of the cup press against the bottom end of her swollen cunt lips and shuddered at the foreign feel of the cold plastic. Without having to think, Anna instinctually pushed the jism that had been marinating in the depths of her digestive system out with a low grunt and moan.
“Oh..good girl..good fucking girl..god that is hot.” Brian spoke from behind her as the liquid sloshed out and she heard thick splats. The liquid burned her ring as it left her and she gave a few whimpers as he forced her to push hard to ensure she had removed all of it. Feeling her ass wink and pucker with nothing else coming out she began to relax her entire body.
“come on Anna, down here.”she heard at the edge of her consciousness and like a teenager who didn't want to wake up for school she groaned and gave little kicks with her legs in protest. But, a hand was soon pulling her weak body off the side of the bed and with a painful thump Anna fell on her haunches to the carpeted ground. With droopy eyes she looked up at her fat uncle and gave him the middle finger.
“Oh Anna we are almost done and then you and I can rest till our next scene.” Brian laughed.
As Anna stared into the judging eyes of poppy she didn't want to think of what would be next outside of sleep but first she had to do what her uncle wanted. Taking the sippy cup into her hands Anna sighed and looked down at its contents. Gulping and being pulled rather rudely from her near catatonic state, Anna saw the tell tale signs of her unclean ass and what the deluge of cum had worked free. Floating in the thick sea of yellow cum were clumps of her own shit, islands of disgusting flavor that she would surely have to eat before she was allowed any rest. Anna looked pleadingly up at her abusive uncle but was met with a lecherous grin that told her the answer to the question she had yet to even ask.
“Do you want to see me chew?” Anna asked, resigned to her fate. Brian simply nodded.
With a shrug and an inward, “fuck it,” Anna tipped the cup to her lips and took the first of many swigs. As she gulped the first foul mouthful she felt a clump bump against her lips and she gagged, coughing cum up through her nose and back into the cup. Brian laughed. Looking up at him with a sigh Anna opened her mouth further and let the first clump slide in. The taste was horrific and she gagged terribly, sure she would puke at any moment. But she didn't, even as the taste filled her mouth and the morsel of refuse dissolved on her tongue she simply just couldn't throw up. Anna closed her eyes and opened her mouth before she began to chew, mushing the flavorful clump between her teeth and swallowing. Coughing and sputtering, Anna threw a mini tantrum. But when she looked up at her uncle again he simply nodded towards the rest of the cup in her hands and Anna gave an exasperated sigh.
Keeping eye contact with Brian she tipped the cup back up and felt the chunks slide into her mouth. Brian Smiled and stroked his hardening cock, Anna began to play with her leaking pussy.
“This is what you deserve you dirty slut.”
- 7
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Anna Kendrick: Winning at all Costs