Anna Kendrick: Winning at all Costs

BY : TheChemist
Category: Celebrities - Misc > Threesomes/Moresomes
Dragon prints: 2888
Disclaimer: This is an act of fiction. I do not know Anna Kendrick or John Krasinski at all and this scenario did not actually occur. I make no money from this story.

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

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

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

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

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

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

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

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

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

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

*    *    *

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

“John...the seat is…” Anna stammered.

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

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

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

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

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


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

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

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

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

*    *    *

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

“Nope.” John said with a victorious grin.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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

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

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


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

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

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

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

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

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


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

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

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

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


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

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

“Oh fuck yeah,” John groaned.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

You need to be logged in to leave a review for this story.
Report Story