Title: Winning At All Costs Part 3
Author: The Chemist
Celebrities: Anna Kendrick, John Krasinski
Codes: MF, M+F, Anal, DP, Oral, Watersport
Disclaimer: I make no money from this work of fiction. Do not read if under 18. These events did not happen, I do not know Anna, William or Michael Kendrick, John Krasinski, nor am I associated with them in any way
Summary - John’s second ‘wish’ for Anna is inviting her to a masked party and instructing her to entertain a group of 8 of her cousins, uncles, brother and father. She’s reluctant at first but ultimately consents.
KNOCK KNOCK KNOCK
When Anna Kendrik heard the rapping of knuckles at her door in the pattern she had grown used to, she shot from the bed and practically ran to answer the door. Standing on the other side of her hotel room door was none other than John Krasinski, a man that she had come to known as her master in all things. However, this time the man that most people assumed was nice and mild mannered but was in fact a sexual maniac who had successfully groomed Anna into his perfect sex slut, was not alone. Following the taller man into the room were two women, carrying a dress bag as well as several other hand bags.
“What’s all this,” Anna asked as 2 others followed John into her hotel room.
John walked over to the much shorter girl, reached down to cup the back of her head and then brought her in for a hard kiss. At one time, the 35 year old actress had a firm policy of never sleeping with a married man. However, John had crushed that rule, as well as another dozen or two things Anna swore she’d never do. Hell, even now while the Kendricks were celebrating a family reunion in her home state of Maine, John was staying in the hotel as well, coming to Anna’s room at any hour of the day or night to fuck her senseless.
Anna was so used to John being around that she never really questioned the fact that he was at the same resort as her and her family. In fact, the Office star had even been chatting with some of Anna’s cousins and uncles, and her brother and father a lot. Truthfully, she chalked it up to the fact that they were all big fans of his and his projects, plus whatever her master chose to disclose to her was his business only.
“Stylists,” John replied after pulling his tongue from her mouth. “Shelia is here to fit your dress and mask while Alisha will be dying your hair.”
“Okay,” Anna said, going with whatever the man who effective owned her free will stated. “But why?”
“The reason is because I want your identity concealed, which is why the mask and the little beauty mark they’ll be putting on your chin, the change from your light brown hair to more of a fiery red, and lastly, need to change those eye colors.” John explained.
Anna went to ask more questions but her personal stylists were too busy whisking her up in their process. She still didn’t know why her identity needed to be covered up, but she hoped it was for a public fuck. The thought of being caught, or better yet, watched and recorded, was a real turn on for the Pitch Perfect star.
“What color of eyes would you like to have?” one of the stylists asked.
“I’ll go with one of my favorite sorceresses and get purple,” Anna said after a minute’s thought.
“Odd but I think you can pull it off.”
“With those tits, Anna can pull off a lot,” the other woman added, getting a laugh from all of them.
For the next hour, Anna was transformed. Her hair was now unmistakably red, a shade that was more bright than she’d ever worn it. Her eyes went from their recognizable blue to a vibrant purple that still somehow looked natural. Her makeup was done in a familiar yet somehow different way, with the addition of a beauty mark on her chin. Her slightly wavy hair was worn loose and down over her shoulder, obstructing her ears, which were another of her more characteristic features. Laslty, a mask was fixed to her face, a type that was worn to an Eyes Wide Shut, sex party type, allowing it to hide her features while still being very sexy.
“You look ready to go,” John said, appearing an hour later. “Come.”
Anna stood and followed the older actor out of her room and down the hall until they reached the elevator. Rather than taking the lift, John strode a few extra yards before popping open the door leading into the stairwell. The resort the family reunion was in only had two floors, so after a dozen steps they arrived at their destination. However, rather than exit the stairwell, John tucked out of view in the back corner and started undoing his pants.
“Suck. And be quick about it,” John ordered.
In the blink of an eye, Anna was on her knees in front of John, reaching into his pants to help free his cock. He was still flaccid but the Pitch Perfect star was determined to fix that rubbing his head along her tongue for a few quick passes before swallowing half his member in one shot. It felt weird having a soft dick in her mouth, but after a handful of bobs with a generous amount of suction, John’s enormous 8 inch cock with thickness nearly the size of her wrist was good and hard.
Anna wasted no time once he was hard and began sucking him good and fast. Though she was truly a blowjob queen, blessed with an array of top techniques, tonight for John wasn’t about using the majority of them. Tonight in the stairwell of the Maine hotel was about getting the handsome to cum in her mouth as quickly as possible. John silently concurred, pleased that his grooming of the 35 year old actress had gone so well that she could read his mind practically.
“Gwwkkk...glllkkk...gawwkk,” Anna constantly spewed.
Anna’s wet sucking noise echoes around the concrete walls of the narrow stairwell as she sucked fast. There was no tenderness or love in the blowjob, only swift efficiency, but that was what was required. She knew John was bringing her somewhere, for some nefarious purpose and the unknown was driving her mad...and more than a little horny. How she went from hating his guts to being completely wrapped around his finger, being both his personal sex slave and pimp, helping him secure other girls was still a mystery. However, as she was on her knees, his massive cock in her mouth and constantly gliding along her lips, she stopped thinking about that and only on the blowjob.
“Holy shit,” John cooed from her intense sucking.
Though it was sounding very sloppy and wet, John was pleased to find that it appeared Anna was keeping herself rather together. Her makeup didn’t appear smeared from his angle and it didn’t look as though any of her spit had dripped down onto her wonderfully large tits. Normally he needed to rest a hand on the back of a woman’s head and dictate to them the tempo he liked being sucked at, however Anna needed no prompting. In fact, as John was pushed closer and closer to a record setting orgasm, it was better to leave his hands at his side and let the petite actress continue to do what she had in mind.
Her lips, tongue and hand stimulated every inch of his fat cock, a true feat given his immense size. However, the tiny star was up to the challenge of sucking him off to completion once more. Of course he was looking down, his green eyes looked with her violet ones as her head was a constant ball of motions, pushing forwards and back, tilting in a side-to-side motion to stimulate the base of his cock as well. Not to mention her hand a tugging blur, pulling along all sides of his dick as she literally pleasured all 8 inches at one time.
“Cum for me,” Anna begged between bobs of his dick into her throat. “Give me your jizz. Want it so badly.”
“Then fucking have it!” John bellowed.
This time John did reach down and grip tightly onto her head, almost crushing her skull as a wave of pleasure shot through him. Once again he swore and grunted into the stairwell as his cum boiled in his balls before it came spewing from his tip directly into his sex slave’s mouth. Between his iron-like grip on her head and her reluctance to spill any drop, Anna’s mouth stayed with only his bulbous head between her lips, using her tongue on the underbelly of his member to coax all the jizz from him. Stream after plentiful stream of salty semen came rushing from him, depositing into her mouth, bathing her taste buds in his flavor. Finally, once his strength on the sides of her head relented and his cock stopped shooting ropes of cum into her mouth, Anna swallowed down his large offering and made her way back to her feet.
“Good girl,” John groaned, doing back up his pants. “Now let’s go.”
Anna wiped the sides of her mouth, making sure she didn’t have cum on the sides of her lips and was rewarded with finding another droplet or two. She once again nearly gagged at the putrid taste of his semen, which was normally pleasant. Based on the fact that he was training for another action movie role, all the extra protein he was consuming was making his jizz taste like utter garbage, but still Anna was left crazing for more on a constant basis.
“This is where the magic is happening,” John stated as he and Anna came to a stop.
Looking up, Anna glanced at the door number before reaching to turn the door handle. Instantly, a connection was made and her hand pulled away from the door and she shot her gaze up to John with some of the old heat she once had for him. Not the defeated glare of a submissive slave, but the spunky, combative Anna that he broke, or mostly broke.
“Why are we at my father’s room,” Anna spat with anger.
“Because you are going to go fuck him,” John said as if it was the most normal thing in the world. “Well not just him. He’s one of them, as well as a couple of your uncles, 3 cousins I believe are in there too. Oh, and your brother.”
“John, are you fucking insane! These are my family members! I’m not just going to go through that door and fuck them,” Anna screamed at him.
“If it wasn’t for the fact that they were your family, a gangbang is run of the mill stuff for you,” John started to explain. “Besides, they don’t know that you’re their little Anna. I made sure of that. You’re not going to get knocked up and give birth to some mutant, which is where this whole taboo of fucking family members comes from. Besides, you are a great fucking lay, don’t you think all those single men in there, some who haven’t had sex in a year or two, deserve to experience such a great fuck?”
“But John...my family,” Anna complained but with a lot less venom than initially.
“Anna,” John said, stroking her vibrant red hair almost tenderly. “You’ve come so far. You resisted the gloryhole at first, then you dove right in and loved it. After all, haven’t you gone and done a few more on your own volition?”
“Well, yeah,” Anna replied, a partial smile appearing on her face.
“And wasn’t it you who gleefully helped me seduce a dozen young starlets in the past couple of months? Bending, or even breaking their will until they did whatever I asked of them?” John continued.
“It was,” Anna answered, her smile growing larger as she thought back to those occasions.
“I know that sleeping with your family seems odd, but it's just another taboo for you to crush in your wake, right?” John proposed. “Plus, I’ll count this as the second of your debts to me for cheating at that competition awhile ago.”
In the past month, John had effectively crushed Anna Kendrick’s willpower. He was actually a little surprised she responded initially with such distaste to his suggestion, although the idea of fucking cousins, a couple uncles, a brother and her own father was quite the stretch. However, it only went to show how much dominion and domination John had over the 35-year old star that it only took a little extra persuasion to have her agree to the pure taboo request.
“Okay,” Anna consented.
“Then here we go,” John said, inserting the keycard into the reader.
As they stepped inside, Anna couldn’t believe the scene in front of her. The hotel room was fairly spacious, albeit all one room. To the far side of the room was the large king-sized bed, which contained her cousins Scott and Mikey, who happened to be brothers. On the bench at the end of her bed was her perverted uncle Brian, which made perfect sense for him being present for a family orgy. Beside the bed was a three-seater sofa containing her other uncle Jerry, as well as his 2 sons Steven and Daniel. Lastly, on a right angle to the sofa, was a love seat containing the last two people she’d have wanted to see; her father William and her older brother Michael.
“Oh my God, John!” her perverted uncle Brian roared. “What a hottie!”
“My brother’s not wrong,” her normally mild-mannered uncle Jerry confirmed.
“No he’s not, dad,” Daniel said, standing.
“Not sure where you found this beauty who was willing to fuck a room full of guys, but great job John!” William, Anna’s dad complimented the movie star.
“How did you get all my male family members to agree to an orgy? Some of them are married for God’s sake,” Anna whispered to her master.
“The dark side has secrets layered upon secrets,” John left it cryptic as the rest of the actress’ family got to their feet and formed a semi-circle in the middle of the room.
Of course it was her perverted uncle Brian and his large beer belly that was the first to reach Anna. Running a hand down from his niece’s neck, his fingertip traced down her throat and between her heavenly tits, large and the perfect combination of heavy yet perky despite her thin frame and 35 years. He continued his descent over her flat stomach then hooked his finger into her panties only so he could pull them away before letting them snapback against her skin.
"Mmhmm...we are going to have fun tonight," Brian told the masked woman.
While her pervy uncle continued to roughly grope her large tits, Anna’s most sinister cousin Mikey rounded behind her. He had always made her skin crawl and stories she heard about him only justified that to Anna, but she tried to block at out as she felt his hands pull her dress up over her head and toss it aside. Now with an unblocked look at her slender yet bubbly junk in her trunk, Mikey was greeted to the sight of the rounded, soft flesh in a tiny black thong. However, it was a large round object poking out from either side of the small strand of fabric that got his attention
"Well I see someone is prepared for tonight," Mikey commented.
Pulling her thong to the side so everyone could have a good look at the three inch long black base of a toy resting over her asshole. Following his father’s example, Mikey snapped the thong back into place, this time the panties smacking the butt plug rather than skin. For added measure he cocked his hand back and gave each of her adorable ass cheeks a hearty slap. What Anna lacked in bulk she more than made up for in cuteness, and surprising roundness.
To show that she was a good sport and up to the challenge from the sadistic cousin, not only did Anna not whimper from the heavy blows but she actually wiggled her ass. Mikey indulged her what she wanted to proceeded to give her 2 more spankings, much to her delight.
"I think we can remove this from the proceedings," her kinder uncle Jerry spoke, taking Brian’s spot directly in front of Anna.
Anna felt the clasp of her bra become undone before her muscular uncle slid the garment up her arms. She noted the slackening of the jaw, a common reaction when men or women saw her tits for the first time. She immediately felt her large C cup tits squeezed in his calloused hands, gently at first before his grip tightened, before giving way as he clutched both her nipples in between his thumb and finger. He increased his pressure until the pink nipples become erect but backed off before it was painful, a grin plastered on his face.
“You have some fantastic tits,” Michael told his sister, appearing right behind her uncle.
“What every sister wants to hear from her brother,” Anna thought to herself, apparently her disguise working as her brother would never say that to her.
“Holy guacamole,” her father exclaimed as she took her top off. “Clearly natural as well.”
“Come, feel,” John told the men, a sinister grin on his face as he encouraged Anna’s own dad and brother to feel her up.
Anna stared with her disguised purple eyes into her father and brother’s face as they practically drooled while reaching out for her. Though she wanted to flinch away, rip her mask off to reveal it was her and stop all this, Anna instead calmed herself and let herself be the perfect little sex slave she was groomed to be. In fact, as her brother and father’s hands cupped and groped her perfect tits, the Pitch Perfect star got a perverse thrill, her thong dampening with each squeeze from her kin.
“I don’t mean to insult your mother William, but these are the nicest pair of tits I’ve ever felt,” William commented.
“Wait until you get your dick in her mouth,” John commented, bring a rapturous cheer from the men.
“I think the Hollywood guy has a great idea,” her massive cousin Scott suggested.
“Couldn’t agree more with the giant,” Danny, another cousin, echoed.
Anna took the hint and stepped forward into the semi-circle of men. However, before she could descend to her knees, her father caught her by the arm and stopped her. She felt her dad’s fingers hook in the waistband of her thong and pulled it down, exposing her completely bare sex and the massive plug of the dildo hanging in her ass. With one hand resting on her hips, the nearly 60 year old man closed his free hand around the monstrous butt plug currently filling his daughter's colon. He looked up and saw her mouth open wide but silently as he began pulling, but the toy was large and not coming out without a fight. Finally his strength conquered the tightness of her backdoor and the toy that was over 2 inches wide at the base popped free.
"Oh we are going to have so much fun," Anna’s brother smiled while seeing her asshole stay gaping open for several seconds.
Rather than put the toy aside or place it back in his sister, Michael stood up and spun the girl to face him. Her lips were still parted and when she felt the rubber butt plug touch them she got the hint and opened wider. The tip was only an inch thick but as her brother continued to push more of the toy inside, Anna had to open to the point of unhinging her jaw.
"How does that dirty plug taste," her pervert uncle asked, a bulge already formed in his pants. "You like the taste of your asshole?"
"Trust me, she doesn,” John commented, earning another loud round of cheers.
“My ass is yum and just a bit dirty, which is hot, but I’d rather get some flesh in me,” Anna cooed seductively, albeit in a southern drawl to disguise her voice from her family members.
Anna was on her knees as soon as her male family members allowed her to be. Wasting no time, Anna grabbed the dick closest to her and took him in her mouth. It was only after she flashed her eyes upwards with half his medium-length cock in between her lips that she realized it was the nicest of her cousins, Scott. After an energetic 30 seconds, Anna turned her head 90 degrees to stare right in front of her, swallowing down her second cock which belonged to her disgusting uncle. Despite the fact that she was always grossed out by him and his long lingering hugs and inappropriate touches over the years, Anna sucked on his cock with extra vigor, giving him a full minute before another quarter turn and taking the next cock in her throat.
It was only 5 minutes in and Anna seemed on the verge of being overrun with cock. However, as John watched his promising pupil gulping down dick after dick, she was able to keep up. It took a lot of effort but the busty girl was accomplishing the task. No one had cum yet, not by a long shot as it was much too soon for that after all, but she wasn’t overwhelmed yet, something that was truly remarkable.
“So much cock,” Anna huffed before swallowing down the next one presented to her. “I love it.”
“That’s because you’re a giant slut,” one of the men said.
“You’re damn right about that,” Anna smiled at her cousin before moving onto the next cock she could find.
There were 7 cocks to go around and, amazingly, Anna was able to give each one attention. While her mouth was always bobbing on a penis, each of her hands were also on cocks, pumping their length. After a good amount of time sucking one dick she would quickly move on so that everyone had a turn.
“Ugh!” Anna groaned as her red hair was tugged back on sharply, angling her face upward.
“Your mouth must be getting dry,” her troublesome cousin Mikey stated. “This should help.”
With that said, Mikey horked up some saliva from deep in his throat and took aim, litting the long stream of spit shoot from his mouth. With perfect aim, Anna felt a massive glob of spit landed on her tongue, practically shooting to the back of her mouth, forcing her to swallow down a partial amount of his saliva. It was a gross move, but at the same time he was right in the fact that Anna’s mouth was going slightly dry.
Her two cousins that were brothers decided to team up for their benefit next. Anna was already sucking off Mikey, who had recently spat down her throat. As Anna bobbed her way down the majority of his shaft, Mikey decided that wasn’t good enough. His brother was bending down and began to rub Anna’s bald cunt, which was dripping wet at this point. As the gorgeous actress moaned in pleasure, Mikey took advantage by grabbing the back of her head and spiking his hips forward, easily getting all 6 inches of dick into her mouth and down his masked cousin’s throat.
“Gllwwkkk...glllkkk...kkllkk,” Anna coughed and gagged as she was face fucked by the short man.
After a good 15 seconds, her face now flush and her nose reddened from the constant bouncing against his firm stomach, Mikey let Anna go. The actress immediately choked down a lungful of air but that was all she had time to do before the next family member was up, dick in hand and leading it towards her mouth, which Anna gladly accepted.
Steven, the youngest and weirdest of the cousins, was up next and decided to copy his older males. A little over-eager, the red-haired boy pulled Anna’s face into his groin, making her swallow all 7 inches of slender cock, but made her go onto hands and knees. The change in position brought several men to their knees behind Anna, one of them inserting two fingers into the depths of her wet cunt while another’s finger plunged knuckle-deep into her still gaping asshole.
“Oh my God,” Anna screamed at having all of her holes filled.
Other than the initial screech of pleasure, Anna didn’t miss a beat in continuing to please the men circled around her. While her mouth and left hand worked in tandem to give sloppy blowjobs, sometimes deep throating but usually bobbing with a generous amount of speed, her more coordinated right hand would stroke on the next closest cock. It was a true testament to her skill, that even while being finger-blasted with multiple digits in both pussy and ass, Anna was able to not only handle but thrive in sucking and jerking off her other family members.
Apparently Anna’s favorite cousin Scott was feeling like Anna’s multitasking sexual exploits earned her a reward. While his uncle was still stretching out the petite masked woman’s asshole, which was already fairly loose from the huge butt plug, the massive younger man slowed his hand thrusting. Rotating his wrist and keeping the muscles in his forearm tensed, the man filling Anna’s pussy repetitive tapped his fingers against his undercover cousin’s G-spot. Going faster and faster, this technique was only needed for less than a minute before Anna had to pull her mouth from the cock she was currently sucking, which happened to be her brother Michael, so that she could let out an ear-piercing bellow.
“Jesus Christ! Fuckkkkk!” Anna swore as she came hard.
Job done, which had brought a smile not only to Scott’s face but all the other males present, the cousin removed his fingers from Anna’s cunt. At this point the digits were not just coated in Anna’s juices, but positively dripping in them. Inspiration striking, Scott waited from Anna to finish servicing her brother then timed it right so that before Anna could get her lips around the next dick in line, Scott thrust his slathered fingers into her mouth.
“Mhmmm,” Anna moaned in delight as she sucked hard on his fat digits, drinking down all of her orgasmic juices.
“That sould have loosened her up for some actual fucking,” Anna heard her perverted uncle Brian call out from behind her.
The next moment, Anna felt a tugging on her head followed by a brief flash of pain as a powerful hand from behind her, likely her uncle, pulled her upwards. The dick in her mouth fell away as Anna got up from her knees to her feet for the first time in longer than she could recall. Of course, Brian didn’t keep her fully erect for long, a hand pushing between her shoulder blades had her bending at the hips so that she could rest her hands on the arm of the sofa and her small but bubbly ass pointed back at her uncle.
“Hope no one minds if I have the first go around,” the eldest of the men spoke.
His words were met with a series of nods or shrugs, the rest of the family giving the bulbous and rather perverted man permission to go ahead and fuck his undercover niece. Already in position behind her and his dick wet from her spit from having several go-arounds getting blown, Brian and with his erect cock in hand didn't hesitate in stuffing half his length into her snatch.
"Fuck...that’s good,” Anna moaned after finally being penetrated.
After withdrawing once, Brian slammed back in but this time with his full length. As his hips slammed against her ass, her toned cheeks rippled from the blow. Loving the view of it, Brian did so repeatedly with both hands on her tapered waist so he could pull his movie-star niece back as he speared forward.
"God, man. You’re relentless," John watched in admiration.
Anna most definitely agreed with the sadistic movie star’s assessment of her least favorite uncle’s fucking style. Brian had the size and strength of a linebacker, albeit a retired overweight one, and he wasn't shy about using it to dominate his tiny disguised niece. Over and over his thick cock, which she guessed was about the size of her wrist, slammed into her at a speed that a normal man would have cum within minutes, yet he seemed undisturbed.
Brian didn't know it but his fierce fucking was pushing the horny girl to an orgasm that he didn't think was possible. Of course, Anna was no ordinary girl and she had certainly trained her body over the last 20 years to handle all types of fucking styles, including balls-out aggression. Therefore, it wasn’t too much of a surprise to the petite actress that she felt a familiar electric sensation welling up in her suddenly, pleased that the huge man could bring her to climax so fast.
"SSHHHHHIITTTT! I'm cumming," Anna screamed, her second orgasm of the evening.
The seven other members of the Kendrick family watched on as their masked female squeezed her thighs tightly around the cock in her pussy right as Brian pulled out of her. He sensed she was a squirter only a second before and the drive to see her gush fluid was too strong. The second he pulled out of her snatch it erupted as a large stream of clear fluid jetted out and splashed on the carpet beneath.
The men practically gasped in amazement and stroked themselves, getting harder watching the innocent looking girl drench the floor from squirting. Brian slapped her on the ass for her good work before letting his fingers soak in the fluid beneath. As she stood bent over at the waist, resting against on the sofa’s arm, he flicked the fluid at her, her juices landing on her masked pretty face.
"So slutty," she heard her father’s voice sneer though very aroused.
Seeing that he had gone hard with his thrusting and that he wasn’t in the best shape in the first place, Brian backed away from the lovely masked squirter. Needing his sexual reserves to become restored before taking another turn with the large breasted woman, Brian was more than happy to have a breather as his fellow horny family members had their turn.
Luckily for Anna, there were lots more men around willing and able to take up the charge. She wasn’t aware of who it was that stepped up behind her and effortlessly slide their dick into her wet snatch, but given the slender feel of his member and the way it poked deep into her womb with each thrust, she suspected it was her creepy cousin Mikey. At her other end, she knew for sure it was her brother Michael that had appeared kneeling on the couch in front of her face.
“God, you look so familiar,” Michael commented.
Anna didn’t reply, not knowing what to tell her brother. So instead, as his hand closed around her hair to help hold her steady due to the thumping her backside was receiving from her cousin, Anna answered by cramming Michael’s dick in her mouth. Instantly her brother moaned and thrust his hips forward slightly, not that Anna needed any help in getting a cock down her throat. All while maintaining eye contact with the man who was not only her kin but her best friend, Anna set out to give him the best blowjob she could, despite the fact that her pussy was being pounded at a rapid level and that her right hand was being used to stroke another cock mere inches from the side of her face.
The Kendrick men were showing that their horniess was matched only by their ability to share. A routine was settling in nicely as it seemed that each man got 2 minutes at which ever end they chose, fucking her pussy or being sucked off, before they pulled back and another took their place. Not only was it allowing each of them to receive a high amount of pleasure, it then gave them 5 minutes to cool back down from their pending climax, meaning they were fresh when it was their turn again.
“Come on down here,” offered Daniel, the only member of the family to do jail time.
Once her uncle pulled out of her sntach after another dozen thrusts, Anna took the dick out of her mouth and looked at where the talking had come from. Sure enough, her cousin was laying on his back on the floor, his healthy sized dick standing straight up and waiting for her. His hand grabbed hers as she got to her feet, walking around his muscular body until she was at his groin. Swinging a leg over his waist, Anna squatted down until she felt his bulbous head slice through her folds and took him deep in her pussy.
“Fuck, feels so good,” Anna cooed.
Anna was allowed to build up some rhythm atop her cousin’s cock, bouncing up and down before two lines started on either side. Anna knew the routine as her hands went to the nearest cocks, stroking them off and taking 30-second turns bobbing her red-haired head along their shafts before turning to suck off the other. After their turn in her mouth, the men would walk to the back of the line so that the next family member could have their turn.
“Next up,” Daniel grunted after a few minutes of being ridden, getting a little too close to popping.
Anna finished orally servicing the dick in her face before allowing the criminal’s strong hands to push her hips up, pushing her off her cousin’s dick. She didn’t have long to go because after one side-step to her right, Anna was back straddling another man, this time her favorite uncle Jerry. She didn’t realize but just like when she blew her brother on the sofa, Anna became aware that she put more effort into pleasing the family members that she liked a whole lot more than the ones she despised. She truly was fucked up, especially since she loved when the perverted uncle and asshole cousin would fuck her hard and rithlessly, treating her like a sex puppet.
Anna wasn’t able to ride him to her full ability because both her arms were in use, hands closed around multiple dicks in order to jerk them off. However, she was able to prop herself up high on her knees so that her favorite uncle could thrust up into her pussy with reckless abandon. He wasn’t the longest or thickest she’d ever taken but his dick felt great as it routinely pistoned up into her snatch, giving her hole a nice stretch while reaching into the best areas to help her moan around the cocks in her mouth.
“Don’t be greedy, dad,” Jerry’s son said.
Anna, whose mouth was full of another family member’s cock, could only divert her purple-colored eyes in the direction of the speaker. Sure enough, the youngest of her cousins was already next in line, laying down on his back only a feet and a half away. Once more, Anna finished sucking and being fucked before she got her feet back underneath her and strode the short distance to the younger man, stepped over his waist with one leg and made her descent.
“Anyone gonna put a dick in that gaping cave she calls an asshole?” John asked the room, several men hooting that they gladly would.
“Great idea, Hollywood,” Daniel said.
Though the masked woman had already descended on his cock in her pussy, Daniel went to swiftly change that. Reaching down to fist his cock in one hand, the criminal used the other hand to scoop under her small but curvy bottom with the other. The next time Anna rode to the top of his dick, Daniel helped her up even higher so that he was free of her velvety folds. With his cock held firm, Daniel angled the slender masked woman’s hips down lower before a combination of pushing her down and lifting his hips implanted his member halfway into her colon.
“Oh Jesus,” Anna cursed as her sphincter was spread wide.
Despite the fact it was the first dick in her ass this evening, the massive butt plug that John had gotten her to shove up her bowels had done wonders. While it was going to cause her asshole to be gaped for the rest of the evening, it also ensured that her backdoor would have no problem taking a stiff cock up the dirt road.
The men in the crowd were amazed by how unfazed the big breasted masked woman was. Despite the fact that Daniel was unlubricated other than her natural pussy juices, Anna was riding the dick now in her ass with the same speed and force that she had when in her pink slit. In fact, the anal penetration seemed to make her ride harder, which not only made them all the more excited when it was their turn, but it caused her large, pillowy tits to jiggle even more with each bounce along his length.
“It’s a dirty job but someone has to do it, eh Danny?” roared Michael, Anna’s own brother.
“Hopefully not too dirty,” Daniel replied with a laugh.
All while her criminal cousin sodomized her, and her own brother teased her, Anna didn’t forget that there was a crowd of people around. Thus, as her ass constantly rode the lying man, Anna was jerking 2 cocks and even given a sloppy blowjob to one of them as well. However, the Kendrick family was a clever bunch, and another of her cousins discovered that the shift to her riding the dick in her ass opened up another on of her holes.
“Think you can handle it, babe?” Scott asked, kneeling between her outstretched legs.
“Only one way to find out, sailor,” Anna retorted with a wink.
The mammoth man smiled as he inched closer until his equally large cock was within reach of the large-breasted woman’s sex. Without another moment's delay, Scott pushed his hips forward and speared Anna with a second cock. Instantly the petite starlet cried out in utter pleasure of being filled with over 18 inches of cock simultaneously. God, she loved gangbangs, especially when it led directly to being double penetrated.
Anna’s two cousins took a minute or to to iron out the kinks but they eventually found a smoothness to their fucking. As one pushed into her, Anna felt the other backing out. Not only did it allow the men to plow into their respective hole faster, deeper and just overall better, but the grinding of their cocks against the thin membrane that separated her asshole and pussy added an extra layer of pleasure to the whole double fucking.
“Think an old man can have another go, big fella,” Anna’s father asked his nephew after another minute.
“For my favorite uncle, I think I can share,” the jovial man laughed.
Before Scott got off his knees and allowed someone else a turn with the masked lady’s sweet pussy, the large man took her hips in his huge hands. The sight was almost comical but Scott had them there for a purpose, not just for the visual. Deciding that he could open the throttle since he was set for another spell on the sidelines watching, Soctt began fucking her snatch...hard. Anna, who was not only being pressed against Daniel’s chest as he thrust up into her asshole, was now on the receiving end of the giant’s ruthless fucking deep and hard into her pussy.
“HOOOLLLLYY FUCCKKKK! AHHHHHH!” Anna screamed.
Scott couldn’t keep this sprint up for long so he gave it all he had for as long as he could then pulled out. The men gathered cheered, not sure if it was for Scott’s relentless pace or the fact that Anna had actually cum while being double stuffed. Due to her third climax of the night, Anna only became aware that her father was fucking her pussy after a length of time that she was uncertain about.
“Yes, daddy,” Anna cooed, loving how absolutely filthy it was to be enjoying this.
“Daddy, huh?” William said, a smile spreading across his face, making him pick up his ginger pace.
“I think this slut has daddy issues,” Daniel hissed from beneath her, another thrust going deep into her ass.
“After tonight I will,” Anna said with a laugh.
“Sorry uncle, but I need a break,” Daniel eventually said. “Her asshole may look loose as all hell but she’s hugging my dick tight.”
Her father had heeded his giant nephew’s actions from early and continued to fuck her pussy with a faster pace, though not nearly as ferious given the arthritis in the hips. Regardless, it was made easier since Daniel had stopped humping up into her rectum from beneath his masked daughter. After another 2 dozen thrusts, William pulled out of the redhead’s snatch before Daniel had to beg him a second time, at which time Anna was flung from the felon’s lap and onto the hotel room floor.
“Up onto the bed,” cousin Steven said to her.
Anna was helped to her feet by her hair, making her cry out and this time not in delight. Luckily the grip on her hair relaxed as her wiry cousin dragged her to the bed. Steven was first to the mattress, landing on his back with Anna coming down right on top of him. Looping an arm around her petite body, Anna and her wonderfully large tits were dragged back onto the middle of the bed before Steven stopped moving and slipped his cock into her slick cunt.
“Fuck. So good,” the wiry man exclaimed.
Anna let her younger cousin took the lead initially but his technique was hopeless. Given the fact that he was always a selfish and weird person, it came as no surprise that the lanky man would be useless with a woman. Despite the fact that she came three times already and had been getting fucked and blowing men non-stop for the past hour, Anna planted her arms on his chest and pressed herself up. She only made it halfway up before a strong hand on her back caused her arms to buckle and send her crashing back down on her cousin, tits pressed firmly against his bony chest.
“Don’t mind sharing with your dear old dad, do you son?” Brian spoke from above his masked niece.
“Would be a pleasure,” Steven replied to his father.
Anna felt her uncle’s hand still on his back as he shifted behind her until he was positioned kneeling behind her. She had the warning of his cock head rubbing along her ass crack until he zeroed in on his target and pushed forward. Not blessed with length, her horrible uncle Brian was still thick, making her asshole up for a challenge. Of course she was up for it, but Anna couldn’t help but grunt as her back door was thrust open in one swift thrust as she was once more double penetrated.
Her uncle was fat, unmarried and very much out of practice when it came to sex. However, he knew his limitations. Therefore, he started at a leisurely pace, not giving a shit if he hogged the gorgeous girl’s asshole. Slow and steady, Brian pushed his massive girth forward, spearing Anna on his short veiny cock deeply. She felt every inch slide in and out of her well used asshole, and hated herself all the more for the fact such a monster was allowed to have sex with her. However, she was too far deep down the well, so thoroughly under John’s spell that letting gross creatures like her uncle and cousin fuck her was worth it provided it appeased her master.
“Come on brother,” Jerry pipped up. “You are leaving the rest of us here with our dicks in our hands watching as you crush this poor woman.
“Fine, fine,” Brian said after leaving his cock to soak deep in her anal cavity for a few seconds before pulling out. “Loosened her butthole up for your twig dicks anyway.”
It was disturbing that Anna felt sad to have an unfilled opening in her holes, however it didn’t stay that way for long. Another of her uncles stepped up onto the bed and took the position, and within a few moments was sliding deep into her ass. Her uncle Jerry was a more balanced dick, not as wide as his older brother but a little longer, able to pierce deeper into her colon. As her cousin and favorite uncle found their stride working together to fuck her holes, the mattress rocked in front of her, letting her know that another of her family members was seeking pleasure from her mouth.
“Open up, big juggs,” her horrible uncle Brian ordered.
The two men she was fucking were holding Anna’s fit body tightly, enabling her head to be perfectly in line with her uncle’s crouch. From only a foot away, the gorgeous actress could smell the filth coming from her heinous uncle’s dick and as his hand reached around her head and began pulling her closer, the feeling she needed to retch only got worse. She doubted it was due to the fact he was just fresh from fucking her asshole. Sure, tasting a cock after it was right from your ass was never the most clean thing, but in her vast amount of experience with ass-to-mouth activity, it never was so bad. No, this was likely due to her uncle being a gross slob who likely had gone days or weeks without bathing. Hardening her resolve, Anna parted her lips and took his cock into her mouth, tasting the fresh flavor of her ass on him.
Watching such a beautiful girl with a face of an angel do something so nasty sent a surge through not only Brian, but all of the men watching except for the two men currently double fucking her. They watched her fiery red-haired head bob up and down in his lap, her tongue slathering his cock with saliva and cleaning him up. All while a shift change was happening behind her, her favorite uncle leaving her slender caboose and her brother taking up the large opening.
"Mmm," Anna moaned from around his dick, getting a strong taste her own ass.
“How’s that dick coming from your asshole taste?”
“Not quite foie gras but I’ve definitely tasted nastier asses,” Anna replied, marking her sluttiness by extending her tongue and running it along the side of the dick from root to tip.
It was every bit as nasty and naughty that she was hoping it would be. And it only added to her humiliation seeing the look of shock and amazement in the eyes of all her male family members in the room with her as continued blowing his dirty cock. She really getting off on being such a depraved little slut, letting her gross uncle fuck her in the ass and then sucking his cock clean.
Seeing the lust and hunger in the masked woman’s purple eyes, Brian ignored his own internal warning alarms as he held firmly onto the back of Anna’s head. Thrusting his hips he started fucking her mouth, pushing in until he felt his dirty cock brush against the back of her mouth before pulling back. When just the head of his cock was still in her mouth, the overweight man paused and let Anna suck on the head and swirl her tongue around the crown before pushing back in.
"Awhh...keep going," Brian demanded after another long minute of silence, apart from constantly groaning.
The gorgeous 35-year old actress didn't need the advice when it came to blowjobs so she merely smirked at her horny uncle. Anna pulled her mouth from his dick, now slick with her saliva with no more traces of her ass on it and used her hand to feverishly beat his meat. She did this so that she could use her tongue to help corral his heavy sack to bring it into her mouth all while her body was pitched back and forth from the relentless fucking befind her.
Anna took turns taking each nut into her mouth and giving it proper attention before she turned her oral affection back to something more solid. After all,she recognized the noises and lack of coordination in the large man’s movements, meaning that continuing with this quick and dirty blowjob would soon finish him. She moved half of his pole between her lips while stroking the other half. Using her free hand to massage his sack again, she could hear how much he appreciated what she was doing.
“Fuck, fuck, fuck, fuck. Here it comes,” Brian groaned, his hand tightening on her head.
Anna was thankful for the warning or else his first blast of super salty, repulsive cum could have made her gag. However, when the first spurt splashed against the roof of her mouth and dripped onto her tongue she was able to compose herself and not throw up from the horrible taste, instead swallowing it down. She did likewise with the following 4 squirts, each one less than the preceding one until her grotesque uncle was fully exhausted and moved off the bed to collapse in an armchair in the corner.
“1 down, 7 to go,” John offered his commentary.
With her uncle out of the way, the men took the chance to resume normal behavior. Luckily for Anna, both her years of copious amounts of sex and her training before coming here tonight with the massive butt plug had prepared her well. Which was good because these Kendrick men were determined to tear her anal ring apart if they had their way. Because the 7 men could take turns on her, it meant that they could go all out then take a break and back down from their pending climax, making them always be fresh.
With the constant cycling of men moving in and out of her pussy, asshole and mouth, Anna lost track of time. She lost track of a lot of things actually. For instance, she knew that she came at least once more, but it could have been 2 or 3 times. However, there was nothing quite like an urgent man’s tone and being tossed to the end of a bed to snap Anna back into reality.
“Open up,” a man urgently demanded.
Flat on her back, Anna did as she was told and parted her lips in a wide O. A dick was instantly placed on her tongue, a hand still rapidly beating the bottom several inches. Anna didn’t know what it said about her but she knew that the size, thickness and amount of small veins meant that the dick belonged to her criminal cousin Daniel. Sure enough, a quick peek up and her eyes confirmed that indeed, it was the man she presumed.
Her thoughts about her cousin’s dick in her mouth ended there as his tip started to spew the custard she had earned via her tight holes and being able to take a hard pounding despite her lithe build. His cum was saltier than her gross uncle’s, yet it lacked the slimy disgusting taste that the 60 year old man’s jizz tasted of. Therefore Anna was happy to collect his spunk in her mouth, bathing her taste buds in his thick seed before swallowing down every last drop.
“Turn,” a familiar voice instructed the large-breasted woman.
Anna didn’t question, she only acted by turning her head in the direction of the order. The masked woman’s eyes were still closed, not wanting to take a stray rope of jizz to the eye and have it burn. However, John, who was the man who had spoken, had other plans in mind. With top accuracy given the fact Anna’s open mouth was a moving target due to her own father hammering down into her pussy, John took aim and fired.
Anna was unfazed initially as a splash of warm fluid squirted into her mouth. It took her brain a second to realize that the salty, thick goo she expected was instead very watery and acidic. Opening her eyes, she was right in time to view as John’s slit on the head of his flaccid cock opened and a thin stream of pale amber fluid came flowing out in an arch, headed to her outstretched tongue and open mouth. Despite the surprise watersport, Anna was composed enough to let the tall man completely fill her mouth with his urine before she had to close her lips, taking the end of the stream onto her mouth and cheek before he stopped peeing on her.
“Swallow that down you piss guzzling whore,” John spat.
Once more, the men watched in astonishment as Anna opened her throat and swallowed the mouthful of piss without complaint. It took her 2 attempts to get it all down, but she accomplished the task the Hollywood actor gave her, even smiling in satisfaction afterwards.
“Holy fuck! He just pissed in her mouth,” Mikey commented, simply astonished.
“And she liked it,” Anna’s brother added in amazement.
“So hot. Needa cum,” Steven, the youngest of the group announced.
Having cleared a path for the slender man to get to Anna’s face, Steven stood right overtop of her as her head rested on the end of the bed. Anna only had to open her mouth and the man almost 15 years her junior did the rest. Steven was her least favorite cousin, but as his cum shot into her mouth and she eat it down just as fast as he produced it, she had to admit his cum tasted the best so far. She wasn’t sure if the fact that warm piss had been the last thing in her mouth had made the jizz taste better or not though.
If Anna thought things were going to slow down now that the cum train was in motion than she was a little premature. Instead, she was ripped up from the comfort of the mattress by her favorite cousin, Scott. Rather than being pushed back down, Anna was surprised when she was hoisted up into the air as Scott and his brother Mikey worked in tandem to lift Anna off her feet with her meat of their brother sandwich. It took her a moment to get her bearings but now she realized that her slender legs were wrapped around Scott’s muscular waist with his arms wrapped under her thighs and hands gripping her firm cheeks. Mikey was still behind her thrusting into her ass but now his hands were gripped tightly onto her womanly hips using them to both hold her suspended in the air and aid to drive inside her.
“Oh shit oh shit oh shit! I’m gonna cum,” Anna screamed as she gushed all over Scott’s dick despite cumming less than 10 minutes ago.
It was her most powerful orgasm of the night for the redhead and after she screamed loud enough to puncture both men’s eardrums her lithe body went limp. The result was that both her pussy and backdoor loosened significantly, allowing the horny men to pound into her even harder. The change in position also allowed both men to thrust inside her at the same time as they merely drop her down a foot so she took both cocks balls-deep at the same moment.
Of course, Anna wasn’t the only one deriving great pleasure from the double fucking. Having their cocks separated by only a thin barrier between the redhead’s pussy and rectum meant both men’s tools were grinding against one another. This just added to the amazing sensation of the busty girl’s holes squeezing them tightly for the past while as they fucked her at the same time. In fact both men hadn’t come since they started their tryst an hour ago and they were both well due.
“Need to fucking cum,” Mikey panted from behind the sexy woman.
“You and me both, bro,” Scott added.
They each did a few last thrusts into the skinny girl’s body before they pulled out, rolling Anna to the mattress as both their cocks flopped free of her holes. As soon as she was free of their nearly 2 feet combined of flesh, Anna promptly got off the bed, at which point she lowered herself to kneeling on the ground.
Hearing one of her cousins moaning louder than the other, Anna faced the smaller of the two brothers, Mikey. It was the right call as the large-breasted woman was just in time to see the mild-mannered Scott stroking himself. After one or two pumps with his fist, Scott took aim and shot his load towards her waiting mouth. With lips already parted and ready for his gooey reward, Anna caught every last drop of his salt load and swallowed it down gleefully. For what seemed like the umpteenth time that night, the masked actress took a cock coated thick in her ass juice back into her mouth and proceeded to enjoy the mixture of his cum and her ass on her taste buds.
“Yum,” the tiring sex pot cooed.
Unbeknown to her, the little bastard Mikey was also ready to bust a nut so he moved around to her side quickly, just in time to erupt a typhoon of cum right onto her supermodel-like face. He watched as Anna swallowed down his brother’s spunk then went to give him some post-sex head, even though his cock was straight out of her own asshole. Ready to explode, Mikey couldn’t hold out any longer and released his thick strands of cum onto her unsuspecting face. She was caught off guard as the first salty streak of semen pasted her cheek and nose before she turned to face him. Unable to direct it into her mouth, the second and third strands landed on her forehead and began running down her face with the rest of his load draining into her mouth and small dribbles onto her chin.
“I’m close too,” her brother Michael commented.
“Me as well, son,” their father William added.
“Not yet,” Anna demanded, only remembering at the last moment to disguise her voice in an accent. “I have a special place for you two.”
The two men warned the sexy masked woman to be quick about it so Anna organized them fast, getting her brother flat on his back before joining him. She turned around and sat down on his dick, yet another cock piercing her backdoor that night. Anna no longer winced as her asshole was forced open, instead launched into a dozen bounces along his shaft before settling backwards and beaconing her father forward.
“Come on boys, give it to me,” Anna purred.
“Let’s give her hell, son,” William smiled down at his son as he entered the woman’s cunt.
“Yes sir,” Michael agreed with his own grin.
Anna knew that her beloved father and brother didn’t have long to go before they came, which was why she wanted them inside her. She loved the two men and since she had already broken the taboo about fucking her family members, she figured she’d go all in and let her father fill her womb while her brother got the honors of delivering her an anl creampie.
“Harder,” Anna urged, her large tits swaying faster and faster from her father’s thrusting.
“Gonna pop if I keep going like this,” William warned his masked daughter.
“Then fill my pussy up,” Anna cooed. “You close too, aren’t you, big guy?”
“Ugh! Any second,” Michael grunted without missing a beat as his hips raised off the mattress to spear his dick up into his sister’s asshole.
“Cum for me! Give my ass and snatch your seed. Do it! Cum for me!” Anna begged, rocking her lithe body as much as her pinned position allowed.
“Awh fuck!” William howled from above the disguised actress.
“God damn! Ugh!” Michael grunted, thrusting upwards one last time.
Anna felt her families strokes grow more and more erratic until finally they pushed deep into her pussy and ass, respectively. Moments later, the talented actress felt twin streaks of cum plastering her from all angles. She didn’t know if your brother’s youthful streams fo cum painting her rectum’s walls or her father’s copious jizz strings pasting her womb felt better, so she was happy she had both simultaneously.
“Wow! Very good,” John told the disguised girl. “Ain’t that right men?”
“My thoughts exactly.”