Celebrity Story Site

Author Topic: Anna's Anal Adventure (Anna Kendrick)  (Read 5184 times)

DarkSwordsman

Anna's Anal Adventure (Anna Kendrick)
« on: November 12, 2020, 01:18:57 PM »
Written as a commission for fenderdiesel, who came up with the story and title.

Anna's Anal Adventure

Starring: Anna Kendrick



Hysterical.  That’s how he’d have described her.  For what must have been the better part of an hour, Patrick Ward’s A-list celebrity client had been sat across from him at his neatly polished agarwood desk, sobbing, sniffling and weeping incessantly as she gave him the rundown of her financial woes.  He’d spotted the waterworks coming a mile off.  First, her voice started cracking.  Then came the quiver of the lower lip, and before he knew it, tears were streaming down her face like the River Nile, pooling in her eyes and making a mess of her makeup.

As a top Hollywood agent, assisting the careers of Hollywood’s finest for over a decade, talk of money troubles wasn’t something he was used to hearing.  But today he was getting the full run-through.  The bad investments.  The poor stock market tips.  The ever shrinking bank balance.  The desperate selling of valuable belongings.  It was extraordinary.  A real blueprint for how not to manage one’s finances. 

COVID hadn’t helped and Anna Kendrick had been given little choice but to sit at home, watching her nest egg slowly diminish from one ill-advised monetary play to another, without any lucrative acting work to supplement her dwindling finances.  But with shows and movies starting to return to production, Anna set up a meeting with her agent as soon as she was able in effort to soothe her financial woes. 

“So, do you have anything for me, Patrick?” she asked, dabbing at her watery eyes with a Kleenex, a mountain of others balled up on the desk in front of her. 

“Hmm, not really, Anna,” Patrick replied, thumbing through a stack of upcoming projects.  “Mainly bit parts in shows and a few crappy indies.  Nothing that’s gonna fix your money woes overnight, that’s for sure.”

“Oh, God!” Anna squealed, tears flowing anew.  “What am I gonna do, Patrick?!”

“OK, Anna, calm down.  I’ve had something come in today that I think could be the answer to your problems.”

Anna sniffled.  “You have?” she asked, sounding hopeful.

“Yes.  But it’s a little different than anything you’ve done before.”

“Right, well you know me, Patrick.  I’ve always liked a challenge.”

Patrick grinned.  “Indeed.  Well, tell me this, Anna, have you ever had anal sex before?”

Anna was stunned.  She certainly hadn’t been expecting that.  “Have I ever…?  Oh, for fuck’s sake, Patrick.  It’s not a freakin’ porno, is it?  Jesus Christ!  Did you really think I was so desperate that I’d agree to star in a porn movie?  Fuck me!  I’d rather work at McDonalds!”

Patrick laughed.  “You’re not gonna get to keep your house by working at McDonalds, Anna.  Besides, it’s not porn.  It’s a legit sex education video, intended to keep people safe whilst having anal sex.  And you wouldn’t be starring in it.  They’ve already got a woman for that.  You’d be the presenter.”

“The presenter?”

“That’s right.  You’d be in the same room with the two performers, but you’d just be narrating what they’re doing, and relaying helpful tips to the audience.”

“And this would solve my money woes?  A presenters gig on a friggin’ sex video?  Who’s producing it?  Steven Spielberg?”

Patrick laughed.  “There’s that famous sense of humour.  I was wondering where that had got to.  Good to have the old Anna back.  But, seriously, this is an important subject.  Believe it or not, there are people out there who still aren’t taking AIDS seriously.  Jumping into bed with everyone they meet and banging away without a care in the world.  And more and more women are doing it in the butt these days, Anna.  Trust me,” he added, with a mischievous smile, “I know.”

Anna rolled her eyes.  “Of course you do.”

“But it’s not just STD awareness they’re looking to spread.  The producers of the video are very to keen to ensure that people are staying safe in every aspect of anal sex.  I don’t know if you’ve ever done it before, Anna, but there are a lot of things you have to be cautious of when taking it up the ass.  Tearing of the anal tissue.  The passing of bacteria to the mouth or vagina.  This is important stuff that people need to be aware of.  Which is they’re paying top dollar for the onscreen talent, and why they want a celebrity, someone people love and admire, to relay this information to the viewer.  I know I’d rather listen to what Anna Kendrick has to say over some boring ass doctor.”

“Yeah, good point.  I mean, what have doctors ever done?” Anna quipped sarcastically.  “They only save lives every day of friggin’ the week!”

“Oh, boy.  You sure are on fire today, Anna.  Please, save some of that wit for the video!”

Anna grinned.  “So, why does it matter if I’ve had anal sex or not?”

“Well, there’s a script of course, but I think they wanted someone who could offer their own insight to the audience.  After all, the viewers will be more engaged by a famous actress sharing her own experiences with anal sex, rather than just reading some lines she’s been given.”

“Well, in answer to your question, Patrick, no, I haven’t ever taken it up the ass.  So if that’s a deal breaker, then…”

“They said that ideally the host would have a little experience in the matter.  Ideally.  They never said it was a deal breaker.”

“I see…”

“So...shall I tell them you’re interested?”

Anna considered the offer laid out before her.  It was far from ideal, and she wasn’t sure she wanted her name attached to a sex video, even an educational one.  But what other options were there?  Sell her home and live like a schmuck in some two bedroom apartment, slowly reaccumulating her wealth with one shitty independent flick at a time?  No, thanks.  She’d been there and done that already. 

She sighed.  “OK.”

“You’re interested?”

“Interested’s not the word I would use, but yes, tell them I’ll do it.”

Patrick grinned.  “Perfect!  I’ll pass that on.  I’ll give you details once I’ve secured the gig.”

“OK.  Thank you, Patrick,” said Anna, rising from her seat and heading for the door.

“You’re welcome, Anna,” Patrick replied, “and good luck.”  Anna smiled at her agent as she left his office, closing the door behind her.  His lips curled up in a menacing grin.  “You’re gonna need it.”

*

A shiny black Audi A8 pulled into the parking lot of a rather rundown looking movie studio in the San Fernando Valley.  The front door opened and out stepped Anna Kendrick, cute little nose turned up as she eyed her surroundings.  Anna had seen the exteriors of many a studio during her career in the movies, but none that looked quite like this.  For one thing, it looked to be about a tenth of the size of the buildings to which she was accustomed; a single storey establishment that looked no bigger than a clothes store or sports bar.

Many of the windows were boarded up and there was a sign above the door that read AN_L A_DI_TS V_DEO thanks to several missing letters.  Anna was fairly confident what the third word was supposed to be, and could have a pretty good guess at the first (the nature of the project was something of a giveaway).  But what the second word had once been, before years of neglect had robbed it of two of its characters, was anyone’s guess.  Figuring it was probably some kind of medical term, Anna shrugged it off. 

But whatever its full name might have been, it didn’t look to Anna like Anal A_di_ts Video had two dimes to rub together to make a third, much less the seven figure sum that she’d been promised when she signed the contract.  But her agent had never let her down before, and if he negotiated her such a handsome payment from this mysterious company, then she was confident they’d be able to pay it.  She pulled open a door that was one half glass and one half cardboard and gaffer tape, and stepped into the pokey reception.     

“Ah, Miss Kendrick,” said a heavily made up, bleach blonde receptionist, greeting her from behind a gaudy-looking desk.  “You made it.  Mr Bigwun is waiting for you in the studio,” she declared, stepping out from behind her desk.  “Come on, I’ll take you through.”

“Thanks,” said Anna, wondering what in the hell kind of a name ‘Bigwun’ was as she followed the receptionist through a set of twin doors and into a cramped, little studio.

Much like the rest of the building, the studio itself bore little resemblance to the top of the range movie studios that she was used to working in.  In fact, it looked more like a photographic studio for some of the small, now almost certainly defunct, magazines she’d done interviews for early in her career.  A large roll of seamless white paper stretched across the back wall and across the studio floor, with an equally white leather ottoman laid out on top of it.  What Anna deemed to be an unnecessarily large crew for such a tiny studio, were gathered around the edges of the room, puffing away at cigarettes while they held up boom mics, set up light stands and fixed cameras to tall black tripods.

“Miss Kendrick, Mr Bigwun,” said the receptionist, calling over a slicked back, mustachioed man with a giant Cuban cigar perched between his lips.         

“Thank you, Crystal,” he replied as she crossed the studio floor, hand held out in front of him.  “Afternoon, Miss Kendrick.  I’m Ivor Bigwun.”

He wore a white shirt that was buttoned down almost to his navel, revealing an impossibly hairy and slightly greying chest, the hem tucked into a pair of tight navy slacks.

“Err...hi,” said Anna, giving Ivor Bigwun a rather reluctant shake of the hand.

Bigwun laughed.  “Yeah, I know what you’re thinking.  Porn name, right?  Well I can assure you, it’s nothing but the moniker I was born with.  Bigwun was a common surname in the Netherlands, when my great grandfather emigrated to Pennsylvania all those years ago.  And my first name?  Well, let’s just say my parents had a pretty twisted sense of humour.  High school was a treat, I can tell you that.”

Anna honestly couldn’t tell if he was serious or not, but offered him a good-natured smile all the same.

“No need to worry, Anna.  The content we shoot is strictly educational,” Bigwun continued.  “Ever watch one of those sex ed videos at school?”

“Yeah.”

“Well, that’s us.  Only our work is on a much grander scale.  People from all over the globe buy our videos.  This is important stuff we’re teaching here, and it’s great to know that so many people are so eager to learn.  OK, I think that’s enough of my spiel.  I think it’s about time we get you into hair and makeup.  What do you say?”

“Sure.”

“Great!  Just through there, honey,” said Bigwun, pointing to a door at the far side of the studio.  “We’ll see you in a bit.”

*

Upon entering the small and dimly lit makeup room, Anna was surprised to learn that the studio’s receptionist also doubled up as its resident stylist.  And as she took to a chair in front of a cluttered, old vanity, the shock only grew as the phone answerer-cum-make up artist dabbed, powdered and glossed her pretty face with enough cheap and tasteless cosmetics to put the average street walker to shame. 

“There,” said the stylist, taking a step back and admiring her handiwork.  “All done.  What do you think?”

“Don’t you think you’ve overdone it a bit?” asked Anna, gazing forward in disbelief at the overly made up face reflected in the small, smeared mirror. 

The stylist laughed.  “Trust me, girl, this is how Ivor likes it.  If I came to work with less than half of a department store shelf on my face, he’d fire me on the spot.  OK, dressing room is through there.  Your outfit’s been laid out.”

Anna rose from her seat at the vanity and stepped into the dressing room, her face screwed in an almost comical look of horror as she caught sight of the costume hanging from a hook on the wall.

*

Ivor Bigwun and his crew turned en masse as the door to the makeup room swung open and out stepped Anna Kendrick, her gorgeous, slender form squeezed into a PVC uniform that left precious nothing to the imagination.  The zip on the front of the outfit had jammed halfway up the chest, leaving a generous portion of her perky, B cup cleavage on full display.  A ridiculously short hem hugged the twin spheres of her peachy, little ass, giving way to a pair of frilly white stockings that started at her upper thigh and didn’t stop until they reached her toes.

“Wow!  You look great, doll!” Bigwun exclaimed, staring at her with a sinister leer.  “Doesn’t she look great, fellas?”

The crew gave low murmurs of affirmation, they too ogling her slutty outfit with as little shame as their boss.

“Er...thanks,” said Anna, teetering on an unspeakably spindly set of six inch stripper heels as she crossed the studio floor.  “I must say, Mr Bigwun, this is quite the outfit you’ve picked out for me.”

“Please, honey, call me Ivor.  And, yes, we thought we’d put you in medical attire for this one, since it’s a sexual health video and all.”

“Yes, but why is it so…?” Anna paused.

“Sexy?” said Bigwun.

“Not the word I would use, but, yes…”

Bigwun grinned.  “Well, what can I say, Anna?  You’re an attractive woman.  You’ve heard that old adage, right?  Sex sells.  Like I said, this is a perfectly reputable title we’re working on here, but there’s no denying that putting a beautiful lady up front and centre in a provocative outfit is going to boost our sales.  It’s the way of the world, I’m afraid.”

“Right.  But why…?”

“OK, let’s get this underway, shall we?” said Bigwun, cutting off his onscreen talent before she could protest any further.  “How about we introduce you to your co-star?”

Anna was taken aback by the use of the singular.  “Co-star?  But I thought…”

Any further protestations Anna might have had were promptly quashed when the studio door swung open and a young man in a pair of skin tight briefs came swaggering through. 

“Anna, this is Chase,” said Bigwun.  “Chase, Anna.”

“Charmed,” Chase declared, taking her hand and kissing it.

Anna gawped listlessly at the muscled god of a man stood before her.  Thick blonde hair neatly parted, blue eyes glistening, teeth shining bright- Chase boasted the kind of good looks that would make even the most devout of lesbians go weak at the knees, and a body that women from all walks of life would do anything to get their hands on.  His jawline was so chiseled it looked like it had been carved out of granite.  Veins throbbed in his biceps.  Pecs bulged on his chest.  Countless abs rippled beneath. 

Though as impressive as these features were, for Anna they barely drew the eye.  Indeed, every last fragment of attention was drawn to the giant slab of meat stuffed into his undies.  Stretching the waistband and testing the thin cotton to its limits, was a huge crotchal bulge, the likes of which Anna had never before witnessed in all her years of sexual activity. 

Bigwun chuckled.  “Looks like you’ve found something you like, huh, Anna?”

Anna didn’t reply, but Bigwun wasn’t surprised.  Frankly, he wasn’t sure he’d have gotten a response if he’d told her the studio was on fire, but he carried on addressing her nonetheless.

“It’s a big one, isn’t it, honey?”

Hearing his words, but paying little attention to the content, Anna nodded.  Slowly.  Like she was in a trance.  And who knows, maybe she was.

“What do you think, Anna?  That thing gonna fit in your ass or what?”

Finally, his words hit home, and that final question penetrated her enraptured haze like a bolt from the blue.  Looking across at Bigwun, she did an almost comical double take.       

“Wait.  What?  Aren’t I the host?”

“Yes, that’s right,” Bigwun replied.  “And as the host you’ll be giving the folks at home a hands on demonstration on how to properly engage in anal intercourse.”

Anna’s mouth hung open, sucking up passing flies as she tried to work her brain around this latest revelation.  Those certainly weren’t the terms Patrick had laid out for her when she agreed to the project.

“Hang on, I thought there was another woman doing that.  I thought I was the narrator!”

This drew a chorus of chuckles from the director and the rest of the crew.

“Narrator!?  Pfft!” Bigwun scoffed.  “You didn’t think we’d pay a seven figure sum to a narrator, did you, honey?  Even one as pretty as you.  Jeez, we’d be bankrupt in a week!”

Bigwun and his crew were now cackling raucously, slapping their knees and clinging onto one another for support as they fell about the studio in fits of laughter. 

Lower lip trembling with newfound nerves and having to raise her vocal volume over the room of laughter, Anna voiced her concerns.

“Oh, God!  Well, there’s clearly been a mix up here.  My agent told me I’d just be relaying information to the camera.  He said nothing about…,” she looked at Chase’s crotch again and gulped, “this.  I really don’t think I can do that.  I’ve never even done anal before!”

“OK, Anna, OK,” said Bigwun, wiping tears of laughter from his eyes.  “You’ve already signed a contract so I really don’t have to do this, but since there’s clearly been a little confusion and because I’m such a nice guy, I’m willing to double your pay if you take on the starring role.”

Anna was horrified.  This was a lot more than she’d signed up for.  Part of her couldn’t believe she hadn’t bolted at the first mention of ‘anal sex’.  And she knew full well that that’s what she should have done.  Yet there she was, rooted to the spot; clearly conflicted, the words ‘double your pay’ playing in an endless loop in her brain.  Double your pay.  Eight figures.  Holy cow!  She’d never have to worry about money again, that was for sure.  She’d get to keep her house, her cars, all her worldly possessions.  Heck, she’d never have to work again if she didn’t want to.  No more crappy indies, poky trailers or pervy directors (OK, one more pervy director). 

Plus, that cock was friggin’ huge!  Under normal circumstances, she’d be pushing that guy down and mounting him like a thoroughbred.  She wouldn’t be putting in her ass oridinarily, but, who knows, maybe she’d like it.  Besides, it was her first time.  They were bound to break her in easy.  She hoped so, anyhow. 

“OK,” she said, “for double the pay, I’ll do it.”

“Fantastic!” Bigwun exclaimed, motioning to the crew to ready themselves for shooting.  “OK, let’s get you into position.”

He gestured to a leather ottoman that lay before the snow-white background.  Anna sat down and tugged at the hem of her PVC outfit, wary of its meagre length and the cotton panties she’d been told to leave behind as she left the dressing room.  Bigwun sat before her on his fold out director’s chair, grinning wickedly at the anxious starlet as the bright studio lights shone on her pretty face. 

“We rolling?” he asked, looking up at the cameraman beside him.

The camera guy gave a thumbs up, peering through the viewfinder of his expensive rig.

“OK.  Action!” 

Anna swallowed hard and began reading her lines as they scrolled across the teleprompter. 

“Hi,” she said, smiling timidly at the lens.  “I’m Anna Kendrick and welcome to...ahem...Easing Into Sodomy: A Beginner’s Guide to Butt Stuff, a brand new educational video, designed to give you the definitive lowdown on all things anal.  That’s right, guys.  While anal sex can be very fun and pleasurble to engage in with your loving partner, it is a hotbed for potential health issues.  In this video, I’ll be showing you the methods and practices that you must adopt to ensure that any backdoor intercourse you choose to engage in is entirely safe and pain-free as possible.  Let’s begin. 

“Now, a good way to start out, especially if you’re an anal virgin like I am, is with the use a few toys.  They will help loosen you up and prepare you for what’s to come.  There are a lot of different kinds of toys on the market, but buttplugs are the most effective, since they’re made specifically for the ass.  Hence the name.  I think my co-star just so happened to bring along a little toy for us to use, so why don’t we bring him out and meet him?  Ladies and gentlemen, meet Chase.”

As Chase sauntered into frame, the camera zoomed in on a close up of his package then panned across to Anna; the actress looking no less bewildered than the first time she’d seen it.  Chase handed her a small pink buttplug, which she held up to the lens.

“So, this is the kind of toy you want to be using if you’re just starting out.  Nice and small.  You can either pop it in yourself or let your partner do it.  I think Chase here wants to try it himself.  Don’t you, man?”

Chase nodded enthusiastically. 

“OK, so the best position for the insertion of toys, and for anal penetration itself, is doggstyle.  Like this.”

Anna demonstrated, clambering up onto the ottoman and bending over, thrusting out her ass to the camera.  The camera guy zoomed in tight on her butt as Chase sat beside her, aligning the tip of the plug with her taut, little sphincter. 

“Hey, wait,” Anna protested.  “You’re gonna used lube on that, right?”

Chase looked over at Bigwun who gave a grudging nod. 

“Err...yeah,” Chase replied.  “Of course.”

“Yes,” said Anna, “lube is very important when inserting anything into your backside, as the ass doesn’t get wet like the vagina does.  There are lots of different kinds of lube, all sort of different flavours and extra slick ones that are designed specifically for anal.  What kind are we using today, Chase?”

“Spit.”

“Oh…” Anna replied, suddenly looking rather concerned.  “Well, make sure you get a lot of it on there, OK?”

Chase nodded and spat into his hand, smearing the saliva around the head of the toy. 

“It’s also a good idea to apply some to the point of entry too.  Isn’t that right, Chase?”

“Uh huh,” he replied, setting the buttplug down for later use as he knelt on the floor behind her.

He tugged the hem of Anna’s nurse uniform the short distance to her hips, revealing her ass in all its peachy, round glory.  Digging his fingers into the supple cheeks, he carefully prised them apart.  Taking a brief look at her pink puckered asshole, he promptly buried his face inside, plunging his tongue straight up her rectum. 

“OH!” she yelped, eyes widening as that long, slick tongue invaded her rear.  “I meant spitting on it, but that’s one way of doing it I guess.  Phew!  I’ve never had my ass licked before, but I’ve gotta say, this is quite pleasurable.”

Chase bobbed his head in and out of her booty, sinking deeper into her cavity with each motion.  With Anna’s asshole now thoroughly greased, Chase finally emerged from the depths of her crack.   

“Wow!” she cooed, voice light and breathy.  “OK, that oughta do it.  So the key to inserting a toy is to do it nice and slow.  Especially if it’s your first time.  Chase, care to demonstrate?”

Chase pressed the buttplug’s rounded tip against Anna’s rim and give it a nudge.

“Uhh!” Anna groaned as her brown eye was split open for the very first time. 

Chase continued to push, guiding the small pink toy slowly through Anna’s stubborn slot.  Guiding it past the widest point, Anna’s ass sucked up the remaining plastic with consummate ease, the thin pink stem all that remained as she swallowed the buttplug whole.

“Oh, fuck!” Anna exclaimed, the hot pink marital aid lodged in her rectum and packed in tight. 

A cameraman moved in and stuck his lens in her face, capturing the interesting mix of pleasure and discomfort etched across her face as Chase retrieved the toy slowly from inside her chute. 

“The best thing about buttplugs is they feel just as good coming out as they do going in.  They’re designed as they are to maximize the pleasure of…”

Anna’s piece to camera was suddenly interrupted as the shiny tip of the small pink buttplug inched into frame.  The camera pulled back as Chase thrust the used marital aid into Anna’s face, one hand still spreading her buttcheeks and making her sphincter gape. 

“Ohh, err...yes, OK,” Anna stammered, looking down nervously at the sticky pink toy pressing against her lips.  “So, there are a number of health risks associated with ass to mouth.  Always make sure you’re nice and clean down there before engaging in anal sex, and if you paritiuclarly like sucking on things once they’ve been up your butt, you might want to douche as well.  You don’t want that dick tasting of shit now, do y...MMPF!”

Chase, having clearly grown tired of waiting, cut Anna off mid sentence as he steered the buttplug between her lips, plunging it right down to the stem.

“Hmm, well it’s certainly an...acquired taste, let’s put it that way,” Anna declared, face screwing a little as she tasted her ass juice.  Turning back to the teleprompter, she continued reciting her prepared lines as they scrolled across the screen.  “OK, so that toy was very small, but we have some larger ones that I’ll be demonstrating for you now.”

She looked up at the director.  “Wait.  I will?”

Bigwun nodded, leering grin as sinister as ever.

“Erm, right...OK.  I couldn’t hurt to prepare my ass a little more I suppose.

Just then, Crystal’s buxom form stepped into the edge of the frame, a tray of sex toys balanced on her manicured hand.  Chase fetched a set of blue anal beads and doused them in lube. 

“Ah, anal beads,” said Anna.  “Now, these are very good for prepping your asshole.  The great thing about these is that the beads increase gradually in size, so you can insert as many of them as you’re comfortable with.”

Chase pushed the first bead- a tiny one, about the size of a marble- carefully into Anna’s butthole.  Rectal muscles still relaxed from the previous toy, the small plastic orb slipped in with ease and was closely followed by a second.  By now, the beads were starting to get a bit bigger and by the time she’d gotten to the third, it felt like there was a big blue golf ball prodding against her backdoor. 

Pushing hard against that thick, round sphere, Chase fed it slowly into Anna’s rectum.  Asshole stretching lewdly around its girth, she mewled and whimpered as it slid inside.  Three plastic balls wedged in her tailpipe, Anna prepared herself both mentally and physically for the fourth and final.  Sporting a girth that was simply obscene, the last blue orb was nudged up against her sphincter.  Looking like it had plucked from a game of pool, neither the director nor his crew knew quite how the brown-actress was going to fit this thing inside her.  But one thing they were sure of- they’d have a great time watching her try!

Giant orb pushed up against it, Anna’s brown eye was split open once more.  Unfathomable girth sliding arduously inside of her, Anna yelped as its thickest point stretched her ass to its limits.  Gripping onto the ottomon for dear life, the pain and discomfort twisting her gorgeous features was clear for all to see.  Finally, and with no small amount of pain inflicted upon her maiden rear, the orb’s thickest point was fed through her stubborn slot.  Asshole quickly returning to its original aperture, a thin plastic thread with a ring at the end was all that remained, as all four of the large blue orbs were packed inside her colon. 

“Wow!” Anna exclaimed, squirming slightly as the four plastic beads mingled in her back alley.  “I can’t believe they all fit in there!  Now, the great thing about anal beads is that the fun doesn’t stop once they’ve been pushed inside, and pulling them back out again can be just as enjoyable as the insertion.”

Chase slid his finger through the plastic loop and gave it a tug.  In a matter of moments, Anna’s sphincter was stretching around the final bead’s monstrous girth once more.  The return journey had proved to be every bit as gruelling as the initial voyage, and Anna’s normally stunning facial features were contorted with the same palpable look of discomfort as they were upon entry. 

Though this time, once that punishing hump had finally been cleared, Anna’s virgin backside ejected the girthy orb with violent propulsion.  In fact, it practically shot from her ass like a cannonball, and had it not been for the girth of orb number three halting it in its tracks, the big blue bead would have fired across the room with enough velocity to knock someone unconscious. 

After that, the remaining three popped out effortlessly, each of the orbs thoroughly smeared in her sticky assjuice.  They certainly needed a good clean and Chase thought it only right that his co-star do the honours, since she’d gotten them in such a state in the first place.  He held the greasy beads up to her mouth and fed then inside.  Anna gobbled them up as quickly as she could, coughing and gagging as the first orb slid past her tonsils and down into her esophagus.   

By the time the final one was in, her mouth had been filled to capacity.  Orbs one and two were dangling halfway down her gullet, while the other two had been stuffed into her cheeks, her mouth bulging like a squirrel with a nut.   Holding the large blue beads in there a little longer than Anna would have liked, Chase finally retrieved them; the brunette actress expelling the plastic orbs in a spray of spit.     

“Phew!” Anna gushed, coughing and spluttering as her throat was finally cleared.  “Well, those things certainly aren’t for the faint of heart, I can assure you of that.  I would recommend maybe trying some that are a little smaller if it’s your first time.  That last one nearly tore my asshole in two!”

Chase returned to the tray of sex toys and selected another.

“Oh, God!  What’s going to be next?!” Anna wondered, looking nervously into the camera.

Chase picked a toy and held it aloft.  At first sight, it looked to just be a regular buttplug.  A black one, similar in size to the one she’d used at the beginning. 

“Oh,” she said, looking a trifle relieved, “that doesn’t look too bad.”

Though her relief was short lived.  Grinning maliciously, Chase revealed his chosen item in its entirety.  Attached to the stem of the buttplug was a thin plastic tube, and on the end of that a large black pump.  Squeezing the pump in his hand, Anna watched in horror as the seemingly innocuous toy expanded to an intolerable size before her very eyes.  She wasn’t sure if it had been blown up to twice the size, three times, or four, but whatever it was, the marital aid’s dimensions were simply staggering. 

“Ah…” she said, an almost comical look of concern etched across her face.

Releasing the pump, Chase deflated it to its original size; the black toy now a mere fraction of the bloated monstrosity that it had grown into.   

“OK, this could be a challenge,” said Anna, staring anxiously into the camera lens as Chase pointed the blow-up butplug against her asshole and pushed it inside. 

Slipping in with ease, the toy’s black stem poked out from between cheeks as its inflatable shaft was lodged up her backside.  Squeezing the pump, Chase’s wicked grin was wider than ever as the blow up toy widened in her backdoor.  Soon, it had ballooned up to twice the size, it’s adjustable girth stretching her rectum as it continued to grow. 

“Oh my God!” Anna whimpered, lower lip trembling as that inflatable toy was puffed up to near bursting point inside her rear end.

Asshole spreading obscenely around its expanding girth, the blow up toy finally reached its maximum size.  Keeping it at peak mass for several gruelling minutes, Chase pushed on the pump once more, deflating it to its original size.  Exhaling heavily, Anna breathed a sigh of relief as the toy shrunk down, sphincter closing up as it was tugged free.

“Phew!  That was quite something!  I honestly never knew they made toys the size of that.  My asshole may never be the same again!  OK, I don’t know about you guys, but all this assplay is making me a little hungry.  Anything to eat around here?”

Suddenly, a hand was thrust into frame, brandishing a pack of Cadbury’s Mini Eggs. 

“Hmm, not exactly a three course meal but it’ll do.”

Anna grabbed the pack of candy and was about to tear it open when Chase reached out and plucked it from her grasp.

“Hey!” she barked, looking back at him irately, as he fished out a piece of candy and stuck it in his mouth.

“Chase,” Bigwun sighed from offscreen, “stop eating the candy.  Those are supposed to be going up Anna’s ass, remember?”

“They’re what?!” Anna asked, looking across at the director in disbelief.

“Oh, yeah,” said Chase, pressing a second chocolate egg against Anna’s sphincter and popping it inside. 

Little exertion was required.  In fact, Anna’s rear gobbled up the piece of candy like a greedy child.  Looking into the camera lens, Anna recited the words scrolling across the teleprompter as the sweet little treat was sucked up into her backside.

“Food and the anus might not seem like the most classic of duos, but trust me, they really do go hand in hand.  Food has made for a fine accompaniment to sexual endeavours ever since the Roman age, and while it probably wasn’t Mini Eggs those guys were playing with, these little things really do fit up your tuchus very nicely.  Just be careful that they don’t get lost up there.  And don’t leave them in too long.  You don’t want them melting in there, believe me.”

Relaxing her glutes and giving a slight push, the small chocolate popped back out just as easy as it had gone in.  Hard shell shining with the juices of her rear, Chase fed the piece of candy that had been up her butt straight into Anna’s mouth, promptly replacing it with another.  But it didn’t stop there.  As the second chocolate egg was popped out of her backside, Crystal returned with a platter of sugary sweets so large and extensive it would have fat kids across the land licking their lips with desire.       

And before long, half the confectionery aisle at Walmart had been stuffed up her butt, the actress gobbling up each sweet treat without a second thought as it came back out.  Finally, and with a litany of candy wrappers and spilled confectionery strewn across the studio floor, Chase prepared the main course.  The entree.  The piece de resistance.  Peeling back the wrapping on a Rainbow Twisty Pop, Chase held the phallic candy to Anna’s lips, watching intently with everyone else as she sucked slowly, sensually along the sugary shaft, working her plump pink pillows from top to bottom.

“Lollipops are fun ‘cause they’re shaped like a dick.  They taste a lot better though,” she grinned, smacking her lips together as she released it from her mouth.  “And they’re on a stick so you don’t have to worry about them getting stuck.”

Chase pressed the tip of the lolly against Anna’s sphincter and guided it in.  Thoroughly slicked with the starlet’s saliva, the slippery sucker slid into her backside with the slightest of pushes, leaving a viscid, multi-colored mess smeared across her ring.  Guiding it back and forth in her now very sticky rectum, Chase didn’t stop until every inch of the phallic-shaped treat had been consumed, leaving Anna with little more than the spindly wooden stick poking out of her butt.  Retrieving it from the depths of her rear, the dick-shaped candy was possibly even stickier than when it went in, and as Chase held it up to Anna’s lips, she got yet another taste of her luscious behind as she took it in her mouth and started to slurp.             

“Mmm!  Yummy!” she exclaimed, licking her messy lips.  “So, as you can see, sticking edibles up your butt can be very enjoyable.  Obviously, the items we’ve used today are just examples and there are lots of different types of food you can use during a spot of assplay.  Just make sure whatever goes up there comes back out again and you’ll have a lot of fun.  OK, moving on.  Douches are primarily used for cleaning the rectum prior to intercourse, but there are a lot of fun things you can do with them during foreplay as well.”

A saucer of milk was placed down on the floor beside Chase’s feet.  He dipped the stem of his large black douche into the dairy lake and squeezed the bulb, filling the device to the brim.  Drops of milk dripped the nozzle as he pointed it at Anna’s rim and slid it inside.  Squeezing the bulb once more, the cool milk drained from the nozzle and out into Anna’s rectum.

“Ooh!  That’s cold!” she declared, shuddering violently as she chilled liquid sloshed about in her bottom.  “OK, so just like with the food, once it goes in, it’s gotta come back out again.  The key to expelling liquid from the anus is to give it a good push.  That way it’ll spray out of your ass like a friggin’ fireman’s hose!  I mean, sure, you can let it trickle out if that’s what you want to do.  But where’s the fun in that?!  Right, let’s do this, shall we?”

Anna laid her chest flat on the ottoman.  Sticking her ass out as high as it would go, she relaxed her rectal muscles and gave an almighty push.  Just as predicted, every ounce of milk jetted from her sphincter like a water gun, spraying across Chase’s face and turning the screen white as it splashed across the camera lens. 

“See?” she laughed.  “Told you.  Right, I think that’s enough foreplay, don’t you?  The sheer volume of items you can stick up your butt really is endless and, in truth, we’ve barely scratched the surface.  But I think it’s about time we moved onto the real thing, wouldn’t you agree?” said Anna, masking her nerves as best she could. 

“OK, so the trick to taking a dick up your ass is to go nice and slow.  It will take a bit of trial and error, but before long you and your partner will find a speed and tempo that you’re both comfortable with.  Then, once you’ve mastered that, you can try kicking it up a notch.  But when you’re just starting out, slow and steady most certainly wins the race.  And of course, make sure you lube up.  Greasing up your sphincter and your partner’s dick are imperative to any anal intrusion.  Especially your first.  Isn’t that right, Chase?”

“Oh, yeah.”

Grinning maliciously as ever, Chase spat a second glob of saliva onto Anna’s asshole.  Rising to his feet, he aimed the tip of his dong at her winking pink ring.

“Hmm, spit again,” Anna noted.  “Well, it worked OK the first time, I gue...OH!” she shrieked suddenly, eyes nearly popping out of her skull as Chase’s swollen crown invaded her back door.  “HOLY FUCK!”

Fun though it had been for spectators and participants alike, the lengthy prep session of Anna’s virgin asshole had all been for naught.  Indeed, there wasn’t a tongue, toy or food item on God’s green earth that could have readied her the forceful intrusion of such a fat, girthy dong.  Anna’s sphincter was beyond tight, and it took a good deal of exertion on Chase’s part to fit even the head of his monstrous prick up her fledgling behind. 

“Oh, sweet Jesus!” she mewled, eyes glossed over as that girthy bellend fought its way into her rump.

After what felt like an eternity had passed, it finally slipped inside, her ultra-tuat rim clinging to the ridge of his crown.  Staring at the wall ahead with bulging eyes and a swinging jaw, Anna dug her nails into the ottoman, clasping onto the cheap leather as Chase’s fleshy python slithered into her backside. 

“Anna,” came a voice to her right, the words barely registered as that giant fuckstick continued its arduous ascent up her tight, gripping rectum.         

“Anna!” the voice repeated, finally getting her attention.

Anna turned to the impatient face of Ivor Bigwun, nodding expectantly at the fresh lines of dialogue queued up on the teleprompter. 

“Oh, yes, sorry,” said Anna, putting a brave face on things as Chase’s girthy pipe stretched her snug pink asshole like an elastic band.  “So this is doggystyle.  Probably the most common position for anal and one of the best, ‘cuase it gives your guy a great view of your ass as he buries his dick in it.”

One of the cameramen stood beside Chase and pointed his camera down at Anna’s behind, capturing her supple rear in a perfectly framed POV shot as that mighty wang burrowed up inside.  By now, Chase was working his hips in smooth, fluid motions, girthy shaft sawing back and forth between her cheeks as he pounded her rear.  Clawing at her backside like a ferocious lion, he spread those cheeks apart, giving the folks at home a fantastic view as his veiny, fat prick tunneled its way inside. 

“This position is also great for spanking,” Anna declared, doing her best to disguise her pained expression as Chase’s meat packed her virgin rear.   

A loud thwack could be heard from just out of frame; a hard smack that caused Anna to wince.  Cutting back to the POV shot, this time Bigwun didn’t miss a thing as Chase brought his hand forward at lightning speed, fingers cutting through the air as he delivered a second hit upon Anna’s supple behind.

“Ahh!” Anna hissed into the camera lens as his hand made contact, landing a forceful spank that made her buttocks sting.

Leaving a red hand print across her cheek, Chase’s muscled arm was little more than a blur as he swung it back and forth, laying blow after blow upon her shapely caboose.   Switching regularly from one orb to the other, the impact of each strike synched perfectly with the ever quickening thrusts of his strong, sturdy hips.  By this point, he was going at her balls deep, his pelvis clattering repeatedly against her asscheeks; buns that were now burning red from his seemingly endless string of merciless spanks.   

“OK, let’s...uhh...talk about...oh, fuck...ejaculation,” said Anna, reading from the teleprompter as coherently as the giant cock wrecking her asshole would allow.  “There are...uhhh...a number of ways that the guy...oh, Jesus...can cum when he’s fucking your...ahhh...butt.  There’s all the usual...uhh...places.  In your mouth, on your face, over your...ahhh...tits.  Of course, he can do it in your ass too, and we’ll be looking at that a little...uhhh...later.  Wait.  We will?” she asked, looking over at Bigwun.

He nodded.

“Err...OK,” she continued.  “But a fun one for this position is pulling out and shooting his...uhhhh...load all over your buttocks.  Ready, Chase?”

“Uh huh,” he replied, voice strained as he wrenched his cock from her anus, stroking it furiously. 

“This is where those tramp stamp tattoos can come in handy, girls, ‘cause they give him somewhere to aim.  Otherwise…”

Then, as if on cue, a deep, rumbling below roared from Chase’s throat as he blew his beans, a thunderous gout of jism blasting from the tip and splattering across Anna’s skin.  As she had just alluded to, the muscled young stud really could have done with a target to fire at, as his aim left a lot to be desired.  His mighty blast did indeed strike her ass.  The problem was it splattered across every other stretch of creamy white skin along with it.  Gooey ropes of semen streaked Anna’s back from her tail bone to her shoulders, thick strands of the stuff making a mess of her nut brown hair.

“Yeah, that can happen,” she said, staring into the camera lens as the fiery goo nearly burned the skin on her back.  “You’re really gonna have to work on that aim, bud,’” she added, looking back at Chase.

“Yeah, sorry about that,” he replied, stifling a grin that suggested his apology may not have been entirely sincere and that his ‘poor aim’ was anything but an accident.

“OK, ass to mouth.  We’ve already dabbled in this with those toys earlier, but it’s a lot more fun with a real cock.”

Chase strolled around to the side of the ottoman and clutched his still hard rod, a string of spunk dripping from the tip.

“Especially one that’s just gone off, ‘cause you get to taste his cum too.”

Anna reached up and grabbed his pole, lips agape as she steered it between them.  Grimacing slightly as she sucked at the head, wet slurping noises escaped her pillows as she coaxed out the last few drops of seed.  Releasing the cock with a loud *POP*, she opened her lips, showing off the shallow pool of spunk churning in her mouth, before closing her lips and gulping it down. 

“Still not used to that taste,” she declared.  Her usually gorgeous face was screwed in all kinds of unsightly ways, the flavour of her asshole lingering on her tongue.  “This guy’s got some strong tasting spunk too.  Jesus, man, when did you last cum?!”

“‘Bout a week ago,” he declared, cock still thoroughly rigid as it flopped up and down beneath him.  “Ivor told me to save it up.  Didn’t you, boss?”

Bigwun grinned.  “That’s right, Anna.  All of your castmates today have undergone a lengthy period of abstinence to ensure that their spunk is as gooey and potent as possible.  The thicker the load, the better it looks on camera.”

All my castmates?!” Anna asked.  “Hang on, I thought…”

“Speaking of which,” Bigwun added, swiftly cutting her off, “I think it’s about time we brought out another.  Tyrone!”

The studio door opened and in stepped Tyrone; a slightly overweight, middle-aged black man who boasted neither the panty-moistening good looks or toned musculature of his light-skinned predecessor, but did have a mightily large penis.  At eight inches, his cock was a little shorter than Chase’s, but what it lacked in length (relatively speaking, of course), it more than made up for in girth and as she stared in bewilderment at the jet black monster protruding from his groin, Anna put his thickness somewhere in the realm of a can of soda.  Tyrone stopped directly in front of her, the open tip of his giant brown bellend mere inches from her face.

“Jesus,” she said, her mouth hanging open.  Utterly dumbfounded.  “OK,” she continued, reading her prepared lines with as much eloquence as she could muster, “so that was doggystyle, now we’re going to try something a little different.”

Anna laid back across the ottoman and pulled her legs back as far as they’d go, her peachy, round butt sticking out invitingly over the edge.  The cameraman moved in for a close up, the brunette’s tiny pink rim winking into his lens as she spoke.

“Now, missionary may not be the first position that people think of when having anal sex, but it really is one of the best.”

Just then, Tryone’s swollen black crown squeezed into frame and as he aimed his girty tip at Anna’s teeny, round butthole, a greater disparity in sizes could not possibly have been imagined.  Pushing forward, Anna’s sphincter spread lewdly around his head as he guided it in. 

“Oh my God!” she gasped, lips rounded in a perfect O.  “Holy fuck, that’s a big cock!”

Thrusting slowly, Tyrone worked his dick steadily back and forth in her gaping rectum, feeding it to her inch by inch.

“Now, as I’m sure you’re aware, ladies, clitoral stimulation is a surefire way to enhance any sexual accouner, and let me tell you, anal is no different.”

Anna reached down and started rubbing her bud, slowly at first; synching her motions perfectly with the thrusts of her co-star. 

“And your guy will like it too.  Since strumming your clit will make your ass grip even tighter around his cock.”

Tyrone wasn’t quite sure how Anna’s ring could possibly have clenched his pole any tighter than it already was, and he grew concerned that any further tensing of the snug pink orifice might have snapped his joint in two!  He pushed down on her thighs as he reamed her mercilessly, Anna’s feet now pushed back so far that the spikes of her heels kept knocking together above her head.     

“Jesus!” she remarked, tit’s jiggling as her dark-skinned co-star impaled her on his spear, boring to the hilt with each unwavering plunge.  “I had no idea I was this flexible!  And my asshole is really squeezing that fat black cock!  Isn’t it, Tyrone?”

“Uh...huh,” he growled through clenched teeth, marking each syllable with a particularly punishing thrust into Anna’s backdoor. 

“And if you keep strumming your clit, soon enough you’ll probably...AAAHHH!!!” she screamed suddenly, fingers ablur as she kneaded herself to climax.

A jet of sticky, clear fluids blasted from her cunt, drenching Tryone’s chunky black frame from his neck to his groin.  But his thrusts didn’t slow and further spurts of sizzling cooch juice sprayed from her urethra as he continued to plow.

“Yeah, squirting,” Anna explained.  “If you rub your clit while getting fucked in the ass it’s kind of an inevitability.  This is also a great position for gaping, and if you hold your cheeks apart as the guy pulls his dick out, your asshole will stretch open like it’s made of elastic!”

Eager to demonstrate, Tyrone pried his cock from Anna’s gripping rectum.  And, sure enough, as the head popped out, that stretchy ring that had once been so small, was gaping like a black hole- a portal so large it could have sucked up the entire solar system.  A camera guy moved in for a close up, the actress’ rear spread so far apart he could practically see into her soul. 

But the fun didn’t end there, and while Anna’s asshole was getting a thorough inspection from the inquisitive cameraman, Tyrone wandered around to the side of the ottoman and stuffed his cock straight into her mouth.  Lips stretching around his girth, Anna once again tasted the juices of her rectum as that fat slab of beef was packed into her oral cavity.  Shaft freshly lubed with a fresh coat of spit, Tyrone returned to his previous position, slotting his dick neatly into her still gaping backside. 

“OK, since we teased you guys with it earlier, let's get onto that internal cumshot,” said Anna, addressing the nearest camera as the powerful thrusting continued in earnest.  “So, the internal cumshot or creampie- anal creampie, in this case- is when the guy shoots his load right up your butt.  Now, anal creampies make both you and your partner particularly susceptible to STDs, so make sure you only engage in this practice with someone that you know and trust.  All the performers in this video were tested rigorously beforehand to ensure the safety of everyone involved.” 

Backdoor reamed more vigorously than ever, Anna felt Tyrone’s turgid length swell even further in the anal corridor.

“I think he’s ready,” she said with a grin.  “OK, buddy, fire away.”

Tyrone didn’t need a second invitation.  Burying himself to the hilt, the pudgy black man roared at the top of his lungs as he erupted, leaving a thick, creamy deposit deep in her aching bowels.  Strumming her clit as he emptied his balls, the waves of spunk splashing against the walls of her colon ignited another orgasm from within her slender frame and she promptly returned fire, giving Tyrone’s chubby dark body a further dousing of her sizzling hot fluids. 

“Holy shit!” Anna cussed, once her co-star had finally stopped spewing.  “That was a lot!  Now, as we learned earlier, anything that goes up your butt must come out again.  Especially spunk.  Of course, you can just let it slop out onto the floor if you want to, but it’s a lot more fun if you squeeze out into a glass and…” she gulped, clearly unnerved by what was to come, “swallow it.  Now obviously for this you’re going to need some kind of vessel.  Judging by how much cum is swimming about in my ass right now, we’re gonna need something big.” 

A champagne glass was thrust into her face by someone off camera and Anna took it from them, clasping the stem in her hand. 

“Yeah, that should do it,” she said, inspecting the vessel.  “I think…”

Legs still spread, she held the glass between her ass cheeks, rim pressed tightly to her flesh.

“So, just as I did with the milk earlier, I’m going to relax my glutes, give it a little push and out it comes,” Anna declared as the seed was expelled from her rectum, coming out first in a slow trickle, then in great, thick slops.

Pooling at the bottom of the glass, the fluid level rose dramatically as ounce after ounce of gooey, hot splooge sloshed out of her backside, the vessel filled nearly to the brim by the time she was done. 

“Geez!” she exclaimed, gazing in wonderment at the shandy of spunk churning away in the glass.  “How did all that cum fit in my ass?!  Right, now down the hatch,” she said, less in instruction and more in attempt to psych herself up for the ceaseless chugging such a monstrous load would require. 

Putting the glass to her lips, the Maine-born actress closed her eyes and thought of New England as she tipped it back, the warm, murky fluid spilling out over the rim and into her waiting mouth.  Wincing as the first few drops hit her tongue, Anna felt the heat of the burning splooge slip down her throat and gather in the pit of her belly.  Chugging it down as she continued to pour, Anna fought the urge to gag as the strong-tasting spunk splashed across her tongue, setting her tastebuds ablaze.  Once the gooey mess had finally drained, Anna rose the glass triumphantly, screwing her face up something rotten as the last few ounces slinked down her esophagus.

“There,” she exclaimed, licking her cum-soaked lips.  “I did it!”

“Not quite, Anna,” Bigwun cut in from just out of shot.  He pointed to the slimy mess of spunk smeared against the edge of the vessel.  “Looks like you missed a bit.”

Rolling her pretty blue eyes, Anna stuck out her tongue and licked around the bowl of the glass, not stopping until every inch had been licked clean.

“OK, so that was missionary.  I hope you guys learned a lot.  So now we’re gonna bring out my next co-star who is going to help me demonstrate some of the other positions that we are yet to explore.”

Tyrone joined Chase at the edge of the studio and watched on with the rest of the crew as the door opened once more and a half-naked Latino strolled on through.  Quietly threatening and fiercely intimidating, he had the look of a Cuban gangster.  Carefully slicked back, oily dark hair gave way to an olive-toned face that was covered with tattoos; stylized inked that continued down his neck, marking most of his wiry torso and beyond. 

“This is Hector,” Anna declared.  “Ola, Hector.”

He said nothing, his beedy brown eyes staring at her menacingly from atop his teardrop tattoos.   

“Erm...OK,” said Anna, looking a little fearful.  “So, as I said, Hector here is going to show me a few of his favourite sexual positions.  Isn’t that right, Hector?”

“Si,” he replied in a thick Latin accent.

“Have you fucked a lot of girls in the ass in your time, Hector?”

“Si.”

“And what’s your favourite position for anal sex?”

“Si.”

Anna looked at the camera and gave a nervous chuckle.  “OK, I don’t think he speaks much English.”

“Si.”

“Right, how about we start with a little spoons, Hector?”

“Spoons?” he asked, a blank look of incomprehension stretched of his inked up face.

“Cuchara,” said a member of the crew.

“Ay, cuchara.  Si, si.  Ciertamente.”

He gripped Anna by the wrist and hauled her across to the ottoman, the actress’ stumbling along in her stilettos as she went.  Hector laid her down on her side across the white leather surface, pulling down his y-fronts as he took up position behind her.  Spitting into his palm, he slicked his light brown cock as he pointed it at her asshole, steering it in with a snap of his hips.

“AHHH!!!” Anna shrieked, eyes bulging as that long Latin rod was buried in her rear.

Hector wasn’t as girthy as Tyrone, but with a foot and change of veiny brown meat jutting from his groin, the Cuban stud had a good three inches on the two that had come before him.  And as he thrust inside, his spicy Spanish sausage pierced the actress deeper than ever before, sinking to the base on the very first pass.  Lifting one of Anna’s thighs and gripping it with his tatted knuckles, her legs formed a perfect right angle, the spike of her slutty stilettos pointing up at the ceiling as he started to thrust. 

Bucking his hips at a furious pace, Hector held her still as he pounded her backdoor, each pass sending his massive Latin member boring right down to the hilt.  Legs shaking and titties jiggling, Anna cried out in a cacophony of emotions- one part agony and two parts ecstasy- as that huge olive wang mined into her deepest parts. 

“The best thing about this position is that’s very easy to switch to another,” Anna explained, speaking into the camera lens that was thrust into her face. 

By now, her asshole was burning raw, but ever the model professional, Anna delivered her lines in a clear and cogent manner, taking her dicking like a champ.

“All you gotta do is turn over onto your knees and, hey presto, you’re in doggystyle.  His dick never even has to leave your ass.  Or, alternatively, your guy can roll over onto his back and take you with him.”

Hector gripped Anna’s waist and turned over onto his backside.  Cradling Anna’s lithe body in his arms, she reached back and gripped his wiry torso for support as he held her in place above him.  Whether he’d understood her directive or just fancied a change of stance, Hector switched seamlessly from one position to the other all the same, keeping his light brown dong deeply embedded in her colon all the while. 

“This is reverse cowgirl; a great position for anal as it gives you the option of letting the guy take control or taking the reins yourself.  Hector here seems like he likes to be in charge, so I think I’ll let him do the...UHH, JESUS!!!” she yelped suddenly as her co-star bucked his bony hips, throwing his Latin trunk up into her rectum like a man possessed.

Inked up knuckles clasped around her tiny waist, Hector kept Anna suspended above his skinny frame as he pummeled her rear end.  Wobbling precariously on her six inch heels, Anna kicked them off and planted her bare feet firmly on the leather ottoman.  Long nails digging into her co-star’s pecs, her body trembled from head to foot as he railed furiously, banging her into next week. 

“Oh, fuck!” Anna squealed.  “I’m gonna cum again!”

Gripping her thighs and spreading them apart, Anna’s pedicured toes now pointed at each opposing wall as Hector pounded her ever harder.  Bucking ruthlessly from beneath her splayed out frame, Hector drove inch after inch of his veiny brown behemoth deep into her bottom, not stopping until another sluice of squirt fluid gushed from her burning cooze.  Spraying forth like the Steamboat Geyser, the jet of lady liquids drenched the filmer in front of her and his expensive camera so thoroughly that her scolding juices nearly fried the motherboard. 
« Last Edit: November 12, 2020, 02:18:52 PM by DarkSwordsman »
Check out my Patreon if you like my work: https://patreon.com/DarkSwordsman
 
The following users thanked this post: Slyguy, fenderdiesel, pixidragon, Calibur009, Dexter07

DarkSwordsman

Re: Anna's Anal Adventure (Anna Kendrick)
« Reply #1 on: November 12, 2020, 02:18:15 PM »
Wiping the fluid from his lens, the cameraman quickly trained back on Anna’s quivering frame as Hector rose to his feet and hoisted her aloft.  Dick still entombed in her clenching rear, Anna threw her arms around his heavily tatted neck as he held her up by the thighs.  Suspended helplessly in mid air, Anna could do little more than pray for a safe landing as Hector lifted her up to the head of his prick and held her there while she spoke to the camera.  

“OK, this is the reverse cradled position.  This position is great because you’re entirely at the guy’s mercy.  I like being in control as much as the next girl, but sometimes it feels great to just give into your man and let him plow you into a coma.  And this position is perfect for that.”

Arms trembling as he held her aloft, Hector kept Anna poised at the tip of his junk just long enough to complete her piece to camera, and no sooner had the final word passed through her glossy pink lips, had the Hispanic stud dropped her back down to the hilt, piercing her on his monstrous wang. 

“AHHHH! FUUUCCCKKK!!!”

Cumming on the spot, her deafening voice nearly cracked camera lenses and smashed light bulbs as that massive stock was stuffed up her backdoor, filling her to the gills.  But that was just the beginning, and Anna was barely given time to recover from the first precipitous plunge before she was hoisted back up to the peak of his joint and dropped back down once more.  And so the cycle continued.  Time and again, he guided the brown-haired actress up and down his light brown rod, spearing her on his impressive length.      

Sinking her to the hilt one final time, Anna felt the increasingly familiar sensation of a girthy wang throbbing in the depths of her rectum.  Gripping her tight, Hector pinned her small body to his, holding her in place as he let loose, firing an ungodly volume of gooey, hot splooge straight up her backdoor.

“AYYY!!!  DIOS MIO!!!” he screamed as his sac was drained, those heavy brown balls deflating like a pair of balloons as he voided himself inside her.

Depositing her on the ottoman, Hector’s sweaty form vanished into the crowd of mostly watching crew members, still panting and muttering to himself in Spanish as he recovered from what had been the ejaculation of a lifetime.  

“Oookay,” said Anna, staring blankly at the Hispanic stud as he disappeared into the mass of bodies.  “And adios to you too,” she quipped, grinning impishly as a flash flood of searing nut butter leaked from her gaping hole.  “Right, well I hope you’ve learned a lot from this video.  We’re almost done but I think there’s time to bring out my final co-star and show you guys a couple more things before those credits roll.  OK, man, we’re ready for you.”

The door opened once more and out stepped not one, but two naked men; one white, the other black.  

“OK, make that men,” said Anna, looking anxious as her two remaining colleagues approached her on the ottoman. 

At first glance, both were distinctly unremarkable.  Average build, average looks.  But the slabs of meat swinging between their thighs were anything but.  In fact, the two men were quite possibly the most endowed of the bunch, and between them they must have had nearly two feet of pipe ready to be laid.  

Anna looked across at the teleprompter, which for the first time since the crack of the clapperboard was entirely devoid of material.    

“Right, well I haven’t been given any direction for this part,” she declared nervously, “so honestly, I don’t know what’s about to happen.”

Jeremy, the light-skinned one of the pair, sat beside Anna on the ottoman.  Aggressively manhandling her slender, little frame, he pulled her up onto his lap, the last of Hector’s jism dripping from her tuchus as she straddled his thighs.  Gripping his pole at the base, he pointed his tip at her winking anus and pushed it up inside.  Sinking to the hilt on the very first pass, his bulbous head lodged deep into her rectum.  

“OK, he’s in my ass, so I guess his friend’s gonna take my mouth.  I believe this is called spitroasting, and I guess it’s called that because...OHHH!!!”

Anna, it turns out, could not have been more wrong in her forecast of proceedings.  Wesley, he of the darker complexion, wasn’t, in fact, interested in her mouth at all.  He had designs on one hole and one hole only, and the fact that said orifice was currently occupied by his fair-skinned counterpart was wholly immaterial.  That’s right.  As if one huge prong stuffed up her rear wasn’t enough, Anna soon felt the head of a second pressing against her already stretched out sphincter. 

“OH, FUUUCCCKKK!!!” Anna shrieked, face skewed with equal measures of pain and bewilderment as Wesley started to push, her asshole spreading slowly, (literally) agonisingly so, around the head of his cock.

Anna was stunned. Completely and utterly dumbfounded.  To her, double anal was nought by a mythical concept, an absurd notion that was every bit as far-fetched as werewolves and flying saucers.  The thought that anyone could fit two dicks up their backside was surely the stuff of fantasy.  And yet here she was, single handedly dispelling that notion as Wesley’s big black cock inched its way up her colon, her elastic anus stretched to near rupturing point as his fat slab slid in alongside his friend’s.  

“Uhh!  Sweet Jesus!” she hissed, clinging onto the ottoman like her life depended on it as that second grithy schlong wormed its way on in.  

Relaxing every muscle in her taut, toned core until her body nearly turned to jello, Anna thought she might pass out from the pain.  But as excruciating as it was, she couldn’t deny that the discomfort didn’t come without its fair share of pleasure tacked along with it.  It was an endeavour of Herculean proportions, a feat of endurance that some of the world's most experienced pornstars didn’t dare subject themselves to.  And she was handling it like a champ, accepting every stretch of meat with faultless grace in spite of the searing pain in her backside.  

Gritting his teeth, Wesley pushed with all his might, determined to fit his cock up her bottom even if it broke off in the process.  He’d pounded a lot of backdoors in his time but Anna’s was quite possibly the best of the lot.  He didn’t even mind that his dick was rubbing up against Jeremy’s, and though he’d never admit such a thing out loud, he actually relished the enhanced snugness that an extra penis provided.  One final push, and that last stubborn inch forced its way inside.    

“Oh my God!  Holy fucking shit!” Anna gasped, cumming instantly as a second bony groin sat flush against her cheeks.  

She still couldn’t quite believe it.  There was two- count them...two- massive, fat cocks balls deep in her behind.  Nearly two whole feet of thick, veiny man beef embedded in her colon.  Then, the thrusting started.  Despite her status as a backdoor virgin, her castmates had done anything but take it easy on her, and Wesley and Jeremy were no exception.  In fact, the light and dark studs were quite possibly the rowdiest of all, and every joint buck of their skinny hips came in perfect unison, sending no fewer than 20 inches of veiny, thick pipe straight up her fledgling rectum.

Sandwiched between their lean torsos, Anna remained perfectly still, doing her best to brace herself for each hard double dick impaling and unleashing a slew of cusses as both of the large, twitching heads tunnelled up her bottom.  One set of hands prying her ass cheeks apart, the other laying firm, hard smacks upon each supple orb, the two men handled her viciously, cocks throbbing away as they pierced her behind.      

With half the crew far too engrossed on the two-pronged action to concentrate on their jobs, the screen on the teleprompter remained utterly blank throughout the whole ordeal, and it was just as well.  After all, Anna was in no state to recite her own name, much less give her undoubtedly spellbound audience an insight into the ins and out (so to speak) of a twin anal dicking.  Indeed, every hard, unforgiving plunge of their double barreled dongs elicited a throaty string of swears from the brown-haired starlet, each louder and more incomprehensible than the once that preceded it. 

Though while Anna was still gripped in the throes of excruciating pain, her body was achieving more thunderous, mind blowing climaxes than she thought possible, and before long, nearly every two-headed pump was sparking a fresh orgasm to life from deep in her slender frame.  And feeling their cocks swell even larger in the depths of her rectum, Anna knew that her two co-stars’ own volcanic eruptions wouldn’t be far behind.  

While the two men had no qualms about sharing Anna’s most forbidden of holes, firing two loads up it at the exact same time was evidently a step too far.  As such, Wesley pried his rod from Anna’s overly stuffed asshole and wandered around to the end of the ottoman, gripping his dong at the base as he presented it for sucking.  Anna’s mouth opened and that coal-dark beast was steered inside, sinking to the hilt and giving the actress a taste of her deepest innards.

Gripping her hair with two clenched fists, he bucked and thrusted into her gorgeous face, sending his big, twitching black helmet soaring deep down into her gullet, making her gag as it tickled her tonsils.  At the other end, Jeremy's arms were wrapped around the small of her back, pinning her to his torso as he threw his cock up into her, drilling her booty in a blur.

Holding her place with locks of her nut brown hair, Wesley was first to go off.  Cockhead throbbing between her puckered lips, he released a deep, husky grunt as he started to fire, voiding his balls of every single drop.  The cum pooled in her mouth; thick sloshes of the stuff nearly spilling out from between her lips as he retracted.  Closing her lips, Anna felt that fiery splooge swirl and churn against her tongue, its powerful flavour sending her taste buds into overdrive.  Closing her eyes, her bulging cheeks contracted as she gulped it down, her features twisting violently as the bitter-tasting goo slid down her throat, joining the leagues of splooge swimming about in her belly. 

“Jesus, dude!” Anna exclaimed, as that rich, gloopy nut warmed her insides.  “That’s some strong-tasting spunk you’ve got there.  I think you could do with a little pineapple once in a while.”

Wesley grinned; a sly, sardonic gesture that suggested that he liked his overpowering seed just the way it was.  

Cum still simmering in the pit of her belly, Jeremy gripped her ass cheeks hard with his trembling fingers as he started to spurt.  Cock throbbing as he voided his balls, there seemed no end to the volume of splooge that he pumped out into her colon, painting her insides white with his slimy, thick issue. 

“Wow!” said Anna, Jeremy hoisting her from atop from his frame and depositing her on the ottoman.  “Feels like he just fired a week’s worth of spunk up my ass!”  

Regaining her composure, she looked across at the teleprompter, which, at long last, had freshly typed text scrolling across its screen.  

“Right, well I hope this video was very informative and hopefully it’s taught you guys that, while something of a taboo, anal sex is a perfectly natural sexual activity, that when engaged in in the correct manner, can be a very pleasurable experience for both you and your part...HMPFFF!”    

Anna’s eyes bulged as Jeremy gripped the back of her head, putting an abrupt halt to her piece to camera as he stuffed his cock back between her lips.  Holding her hair like a set of reigns, he threw his torso into Anna’s face, his slimy rod surging ruthlessly through her oral canal.  

Wesley and Hector quickly appeared on either side, gripping her splindly wrists and filling her palms with meat.  Chase and Tyrone knelt behind her on the ottoman and slapped their dicks against the back of her head, and while Anna was occupied by the five huge cocks ringing her seated forn, more were springing out every which way across the crowded studio.  Cameras, light stands, clapperboards and Lord only knows what else were promptly abandoned as damn near the entire crew dropped trou en masse, unveiling a legion of cocks of every shape, size and colour.   

Anna was guided down onto her back, ass thrust out, legs pinned back as far as they’d go, as a particularly enthusiastic young PA positioned himself at her groin, pushing his cock up against her still spunk-filled rear and steering it in.  A band of randy men jostling for position around her, Anna’s head was pulled one way then the other as dick after dick was buried between her lips.  Some still tasted of her ass from the pounding they’d given her earlier in the recording, while others were getting lubed up by her slick, drooling mouth with that very thing in mind.

Before long, a line was forming at Anna’s business end that stretched across the studio floor and halfway down the hall.  There were PAs, cameramen, producers, executives, janitors; a tally of men numbering way into the 20’s- each and every one of them itching to blow a wad of spunk straight up the starlet’s booty.  

And on and on it went.  Minutes turned to hours.  Day turned to night.  As the line of men continued to grow, Anna’s backside was passed from one desperately horny gent after another, the production soon clocking up a runtime that could give James Cameron’s Titanic a run for its money.  With every boom mic in the vicinity long since deserted, the audio quality left something to be desired, and with all but one of the crew’s expensive rigs left marooned at the tops of tripods, the lion’s share of the video was consigned to a single camera angle.  But unsurprisingly Ivor Bigwun was far from concerned, safe in the knowledge that the actress’ loyal fan base would have put up with all manner of technical deficiencies for the chance to see their favourite star get plowed in the ass.  

And for the past few hours, that’s exactly what had been happening.  In fact, the anal train had been chugging along on an endless loop, each compartment juiced up with enough off-white fuel to transport her halfway around the country and back.  From here on out the loads came thick and fast, and as dick after dick came and went, Anna had been pumped full with so much spunk that she scarcely had room for more.  Some were squeezed out into a glass for her to chug down voraciously, while others were simply left in there to stew; an ocean of the stuff simmering in her guts and growing vaster with each passing second.    

Eventually, the line started to thin, Anna’s supine form ringed by a mass of bodies some three studs deep, every one of them desperate to get their knobs polished by the actress one final time before the roll of the credits.  Humping wildly, the last man in the queue bottomed out in her sumptuous booty, looking to the heavens and bellowing at the top of his voice as he left one final gloopy spunkwad deep in her burning innards.  Spreading her asscheeks apart, he stretched her sphincter as wide as it would go, opening the floodgates and releasing a deluge of soupy jism to rain down onto the studio floor.  

Fighting through the crowd of bodies, the last remaining active cameraman pointed his lens at Anna’s face, her gorgeous features still under siege by an army of rock-hard schlongs.  And as thick, round helmets were slapped against her face, leaving spatterings of precum across her smooth white skin, a familiar voice emanated from the crowd of bodies tussling and jockeying above her head.

“So, Anna,” said Ivor Bigwun, his grinning, mustachioed face looming high above her, “what did you make of your first anal experience?”

Anna opened her mouth to respond, but before a single syllable had even passed from her lips, a huge cock had been stuffed between them.  The bulbous head prodded at her cheek, making it bulge as the dick went off, firing ropes of searing hot cum deep into her oral cavity and filling it almost to the top.  Closing her lips, those cute little features of hers screwed up once more as the exceptionally gooey and impossibly rich-tasting splooge slid down her throat and down into her tummy with the others.

“God!  These guys really do have some powerful seed, don’t they?!” Anna exclaimed, still tasting the remnants of that last thick load long after it had left her trap.  “Erm...yeah,” she went on, finally getting around to answering the director’s question, “well it was certainly an experience, no doubt about that.  A real whirlwind of senses and...MMPF!”

Before she could continue, another cock was steered between her lips, the tip still tasting strongly of her anal pocket as it erupted vigorously, filling her mouth with yet another pool of hot, churning spunk.  Swallowing it down, she stuck out her tongue, wincing at the overwhelming flavour.

“Ugh!  Damn, Ivor, is there a pineapple shortage in this part of LA or something?!  God, these guys need to sweeten their seed!  Anyway, like I was saying, it was a real whirlwind of senses and feelings.  Pain.  Pleasure.  Jubilance.  Humiliation.  I feel like I experienced every emotion going in the space of a few hours.”

“Right, well it sounds like we did our job, doesn’t it, boys?” said Bigwun, generating a triumphant roar from the throng of naked men gathered closely around him.  “So, what would you say to other women who are thinking of making their backdoor debuts?”

Two more loads were fired into Anna’s mouth and she gulped them down before responding.

“Go for it!  Maybe don’t fuck about fifty men for your first time like I did with mine.  That was a little overwhelming at times, to say the least,” she said, reaching down and nursing her still very sore posterior.  “But, by all means, give it a go.  Make sure to use lots of lube.  Spit doesn’t really cut it.  I’m not sure my asshole will ever be the same after these guys went in raw.  But, yeah, enjoy it.  It will probably hurt a little at first, but that will pass and believe me, girls, taking a big, fat cock up my ass...wow!  I’ve never felt anything like it!”

Another cock was pointed at her lips, spasming violently as it shot yet another juicy load into her wide, gaping maw.  Anna closed her lips and was about to swallow it down when Bigwun stopped her with a ring-clad finger wagging to and fro above her head.

“Uh uh.  Don’t swallow yet,” he said.  “I think a few more of my guys are ready to blow too.  Ain’t that right, fellas?”

There were grunts of affirmation from all sides as a number of men moved in close; crowns of all sizes and shades aimed at her lips from every conceivable angle.  Anna’s mouth was already near full and she wasn’t quite sure how she could accommodate the semen of one more man, let alone that of the half dozen or so that surrounded her.  

A black guy to her left was first to go off; the fluid level in her maw rising dramatically as he fired a fiery gout between her parted lips.  Two more quickly followed; adding their special ingredients to the rich spunky cocktail stirring in her open mouth.  By now, the brown-haired actress was practically drowning in semen; her mouth filled with so much splooge that ounces of the stuff were spilling out from between her lips and trickling down her cheeks.     

“OK, now you can swallow,” said Bigwun, grinning down at her in his typically smarmy manner.

Permission finally granted, Anna closed her lips and swallowed; gagging and heaving as what must have been close to a pint of jism gushed down her throat, belly bulging as it merged with the lake of nut butter already sloshing about inside.  

“There, how was that, Anna?” asked the director.  “Did you have fun with us today?”

“Erm...yeah,” she replied.  “You guys sure have a...unique way of doing things here.”

“Thank you!” said Bigwun, smiling proudly.  He wasn’t entirely sure if her comment was meant as a compliment but he took it as such nonetheless.  “And, of course, an actress of your stature is welcome back anytime she likes.  In fact, we’re shooting another video soon that I think you’d be perfect for.”

“You are?” Anna asked, a degree of apprehension evident in her voice.   

“Mmhmm,” Bigwun smirked.  “Bondage.  Safety is a real big factor in that, right?  One false move and you’ve got yourself a body that needs disposing of.”

Anna laughed awkwardly.  “Yeah, I guess you’re right.”

“Great!  We’ll contact your agent.  We go into production in a couple of weeks.  Looking forward to it.”  Bigwun looked into the camera lens.  “So all that’s left is to thank you guys for watching.  We hope you enjoyed this video and we look forward to seeing you again soon.  Bigwun out.”  He looked down at his A-list talent, stil sprawled out beneath him on the plush leather ottoman, his throng of studs still ringing her naked frame.  “Alright, fellas.  Who’s still hard?”

END
Check out my Patreon if you like my work: https://patreon.com/DarkSwordsman
 
The following users thanked this post: Calibur009, Dexter07

Calibur009

Re: Anna's Anal Adventure (Anna Kendrick)
« Reply #2 on: September 17, 2023, 08:07:37 PM »
I know I'm late, but this was a very funny and hot story, Dark.
 
The following users thanked this post: Dexter07

Sign54

Re: Anna's Anal Adventure (Anna Kendrick)
« Reply #3 on: September 17, 2023, 10:21:40 PM »
I know I'm late, but this was a very funny and hot story, Dark.
I have been reading a lot of dirty Pitch Perfect fanfic lately.
 

Tags:
     

    Social Media Links

    Reddit Tumblr NewTumblr bdsmlr Twitter ImageFap

    Partner Sites

    Planet Suzy HotCelebForum Pride Girlz Hyper Dreams Interactive Sex Stories TG-Party BIG BOOBED MODELS CHYOA - Interactive Sex Stories

    DMCA

    DMCA