Anna Kendrick: Anal Before Weights

BY : TheChemist
Category: Celebrities - Misc > General
Dragon prints: 3657
Disclaimer: This is a work of fiction and didn’t actually occur. I do not know Anna Kendrick. Mature themes so must be older than 18. I make no money from this fictional story.

“Why the fuck did I agree to this,” Anna Kendrick cursed at herself.

“My guess, money and fandom,” Anna’s personal trainer retorted. “You're a comic book nerd and when the studio offered to back the money truck up to your house, it was pretty damn hard to pass on.”

“Fuck. You’re right,” the actress agreed.

“Now come on, 3 this set,” the trainer informed.

Anna hated working out. In fact, that’s how she got into this personal trainer mess in the first place. Because she wasn’t hitting the milestones set out by the studio, they hired her a personal trainer to oversee her workouts. In effect, they had no faith in the slender woman to actually do home exercises, thus she needed a babysitter. They weren’t wrong, and even now Anna schemed for ways to get out of doing her strength training, but you can only claim headaches, flu, and diarrhea so many times before they don’t believe you.

When she agreed to the studio's demand of working out, she thought of all the times she did cardio or dancing. When it came to those aerobic styles of exercise, the Pitch Perfect star didn’t mind working up a sweat. It was strength training in particular that she despised, and of course, adding muscle was the stipulation the studio insisted on. In fact, the only thing she liked was the gym clothes, which pushed her impressive bust even higher, and all the fit guys in the gym. But even now she had to go to a private room where it was only her and her trainer in a sequestered space with mats and weights.  

“That’s it! Only 2 left,” he encouraged.

“Oh God! But I’m only only a little girl…” Anna started to protest. “Dude, I can’t.”

“Little for now. But look what happened with ScarJo and Brie and…”

“Not Little Big Olsen,” Anna argued.


“Elizabeth Olsen. Little because she’s the youngest. And big because she’s practically a giant in that family.” Anna explained.

“That’s funny,” the trainer said, passing the actress a water bottle.

“See. I’m funny, therefore I don’t need to be strong.” Anna reasoned. “Quips will get me everywhere!”

“Not into that superhero suit if you don’t bulk up a little,” the trainer replied.

“Ugh. Fine. What’s next?” Anna asked stubbornly.

“Using this resistance band for some squats. So stand with feet shoulder width apart, place the center of the band under your feet then hold the ends in your fists in front of your chest,” he explained before extending his arm down to the petite actress. “Come on. Only 8 reps...but 5 sets.”

“What?! No way…” Anna protested as she was dragged to her feet. 

As Anna was pulled to her feet by the trainer, the actress glanced up at his face and caught where his eyes were everted. Namely straight down at the generous amount of cleavage afforded to her by both the low cut and tight nature of her sports bra, as well as her own naturally gifted set of tits. The trainer tried to catch himself and only glanced down at her boobs for a moment, but by the time he looked into Anna’s face, she had caught him red handed. To go along with his red hands, the trainer now sported a red face from embarrassment.

“Like what you saw?” Anna asked with a toothy grin.

“I...ugh...shit. I’m sorry,” the handsome man apologized in a hurry. “I, well…”

“No, no. It’s fine,” the Pitch Perfect star retorted, the wheels in her head spinning as she formulated a new plan to get out of working out. “What’s your name again?”

“Gabe,” the trainer answered as he handed her the resistance band.

“Well Gabe, I guess having my trainer sneak a look at my boobs when I’m in only a sports bra to work out in is normal,” Anna stated as she stepped on the band and did the exercise.
“It was an accident,” Gabe replied, feeling how weak of an excuse it was. 

In truth, Anna had great tits, especially for her tiny frame and he checked them out because he thought he could get away with it. Just like he had been doing for the past week that they’d been working together. Probably close to a hundred times he’d gazed down at her pressed-together tits as she squatted, lunged, lifted and thrusted during their gym sessions. Same thing with her ass. Though small due to her narrow hips, the amount of work she’d put into working out had mostly translated to keeping her stomach flat and giving a lot more roundness and firmness to her ass. While still petite, her booty was progressing nicely as he visually confirmed as she performed another squat.

“Oh wow. My ass is really sticking out,” Anna commented as she looked over her shoulder during her exercise. “By the way, how’s it coming along? I feel like it's getting stronger and maybe a little bigger, but I’d love your expert opinion.”

“Your buttocks?” Gabe choked out, surprised by the question.

“My ass. It’s not ScarJo booty but...well just feel it and let me know what you think,” Anna clarified. Noting his apprehension, the actress rolled her eyes before reaching out to grab his wrist so she could place his hand on her ass. “Feel. Squeeze. Assess.”

“Definitely gotten firmer,” Gabe told her after having the pleasure of kneading the round flesh for several seconds. “It’s really nice.”

“So do you think it’ll be even easier for me to have anal sex after this training?” Anna said, right at the moment Gabe was taking a sip of water.

Anna was worried for a heartbeat that she had timed the question wrong and that she was about to cause poor Gabe to choke. However, she got her desired reaction as a cloud of mist erupted from his mouth. If Anna thought she had made his face red before by calling him out on scoping out her cleavage, she was wrong. By confirming to this man she’d known for only a week that she performed anal, Gabe’s face turned a shade of red she didn’t think possible.

“Don’t get me wrong. I like anal. But as it stands, I only cum roughly half the time from taking a stiff one up my dumper,” Anna clarified. “Didn’t want you thinking I was some basic bitch who was opposed to butt sex, you know?”

“Definitely don’t think you're basic,” Gabe eventually choked out. “And as for, um, easier anal...I could see that blasting the glutes could help with that, yes.”

“By blast you mean strength training...or actually hammering my tight butthole?”

“Oh shit. Sorry. I meant training. Training with you and me,” Gabe stammered.

“Still not clarifying because you and I can train my ass in either way,” Anna said, staring him in the eye as she insinuated that he’d have a chance to sodomize her petite ass.

“I, um, think the strength training will potentially help with better anal sex,” Gabe chose his words carefully this time with a minimum of stuttering. 

“What exercise now?”

“Oh, right, um, some Bird Dogs. So go down on your hands and knees,” the trainer explained.

“Perv,” Anna said, descending to the position atop her mat.

“Okay so the right arm and left leg extend outwards. And lets alternate each rep,” Gabe said, hoping she wouldn’t notice his growing erection.

“Wouldn’t it be amazing if I only wanted anal from now on? Like, no more birth control, guys could cream inside me all the time. God, that’d be nice, right?” Anna chatted away, continuing to lay her web.

“That would, umm, be quite something. Yes. Definitely,” the trainer replied, his erection at full mast just from Anna Kendrick talking about taking a dick in the ass.

“Care to be the one who confirms the theory?” Anna said with nonchantlancy after completing her last rep.


“My theory that anal will be easier with training my glutes,” Anna explained with an innocent look over her shoulder, finding his eyes alternating between gazing at her adorable face and round ass.

“I can’t tell if you’re serious,” Gabe said after a moment.

“Dead serious. And all it’ll take on your part is to pardon me from training,” the actress stated, her plan coming together.

“Anna...I can’t,” the trainer said, pulling back.

“Your telling me you’d rather make me lift weights than fuck my ass?” Anna said, shocked. “I mean, I get I’m no Scarlett Johansson but I still think I’m hot. Like the hottest girl in your improv class kind of hot, but hot all the same.”

“I’ll be fired by the studio,” he resisted again. “And they’ll just hire you a new trainer when they realize you’ve stopped showing up for your training.”

Anna had thought of this already so played her last card. “That’s the beauty of this. Instead of getting together to ‘pump me up’, we still get together but you get to pump me full of cum.”

“You’re serious, aren’t you?” Gabe commented, mouth agape.

“Here, help me take off my leggings,” Anna said, wiggling her ass enticingly.

“Anna…” he started to protest.

“I just want to do this next set without them on. They are rubbing me in weird places is all,” Anna lied. “This way you get a closer look of what you’d be getting...or passing up.”

Anna stayed down on her knees and since her hands were supporting her weight from falling forward, it rested on Gabe to do the undressing. Reaching up towards her slender waist, the trainer hooked his fingers into the waistline of the super tight but flexible pants. Watching her face to make sure she wasn’t tricking him, he pulled the black leggings down until they were bunched around her knees. Gabe was greeted with the sight of the pale flesh of Anna’s small but curvy booty. Not only that, but in clear view was not just Anna’s bald pussy with its bright pink lips, but also her much discussed crinkled starfish of an asshole.

“Wow,” Gabe uttered. “I think the exercise will be much better this way.”

“You can touch me.” Anna said. “You know, for official training purposes. Make sure the ass feels up to your lofty standards.”

Gabe was so wrapped up in events he couldn’t stop himself from seeing the logic in Anna’s suggestion. With his eyes firmly planted on the Pitch Perfect’s star’s ass, the trainer extended his arms in that line until his fingertips then the entire hand contacted her flesh. Where it was once cute but a little flat, Anna Kendrick now had a firm and round tush that he was confirming with his own touch. 

“You like it,” Anna asked looking back over her shoulders.

“Yes,” Gabe replied, massaging the flesh with both hands now. “It’s so perky. And your pussy is so pretty. Fuck. Shouldn’t have said that.”

“No, it's fine. It’s the problem with having such a pretty pussy. I get complimented on it all the time,” the actress laughed.

“Do you, um, like getting spanked?” Gabe asked.

“You’ve been known to take a few rougher tumbles in the sack,” Anna answered.


“Mmmm...burns so good,” Anna cooed.

She turned her head to look back but Gabe didn’t spare her a glance as his eyes were fixed only on her booty. Facing forward again and waiting for the next blow, she didn’t have to wait long as this time the trainer's calluses hand paddle came slapping down onto her right ass cheek, causing Anna to groan. Once again, it didn’t hurt per se, in fact the sexually adventurous girl actually found the dominant display of spanking was pleasurable somehow. Not enough for an orgasm or anything close to that, but enough that she found her pussy had dampened her panties right through.

“Mmmhhmm yeah,” Anna cooed, unable to hide her moan of delight.

Anna lost track of the amount of whacks she had received but she guessed it was maybe 3 per reddened cheek. She moaned a little louder on his final slap on her sore butt, her pussy a facet at this point. Rather than rear his arm back and prepare to send it crashing back down, this time Gabe let his massive mitt linger on her petite booty. Rubbing the reddened flesh before giving it another knead, the trainer must have reached an answer as he eventually pulled his hands off her. He reached it around to the front and undid her button before pulling the tight fitting shorts down her short, slender legs.

“So you’d want me to fuck you instead of training you?” Gabe eventually spoke.

“That’s right.” Anna agreed.

“But we get together daily. Well, 6 days a week. Always need a rest day,” the trainer corrected himself. Anna nodded. “And the ass?”

“Well, yes. That’s the deal,” the actress answered. “And/or pussy. And/or mouth. Essentially I’d be your sex doll.”

Anna decided more leverage was needed. Swinging her hips to the side until she was seated on her ass, the actress spread her bent legs as much as the leggings around her mid thighs allowed. Reaching a hand down, Anna began to slide her fingers through her wet mound, eliciting moans from herself. After a few circles, the actress dipped one then a second finger into her cunt which only served to make herself scream a little louder.

“Should probably due similar to my ass. You know, just in case you wanna stop playing with all your heavy weights and tight bands,” Anna stated.

Twirling her fingers inside her pussy so that they were drenched in as much of her juices as possible, Anna removed them from her mound and aimed lower. The Pitch Perfect star rimmed her asshole with her lubricated fingertips first before isolating her middle digit and applying pressure against her crinckled starfish. With little effort, Anna felt her anal ring relax and permit her finger to penetrate her rectum completely.

“Ahhh...ohhh! Now should I stop preparing?” Anna asked, moving her finger in and out of her asshole smoothly. “God! Feels so warm inside.”

“Maybe add a second finger,” Gabe finally spoke.

Anna didn’t press for him to confirm that this was the go-ahead to her getting to skip all future workouts. Instead, the actress took the suggestion for what it was but first she decided to add a little extra ass-related kink into the works. Without any actual lube available, Anna decided that spit would work as a fine replacement so she pulled her middle finger from her asshole and brought it to her face. Gabe watched in wide-eyed wonder as Anna stuck out her tongue and performed a long slow lick of the entire digit that was freshly removed from her asshole. As her tongue reached the tip, the Pitch Perfect singer opened her mouth wide and sucked on the middle and index fingers, transferring a lot of saliva to them before reaching back down and inserting both into her loosened bowels.

“Ah...just need some...mmhmm...more lube,” Anna explained as now two digits plundered her booty. “Still a little too tight. Can you play with my pussy at the same time?”

“Like this,” Gabe asked, his fingerpads rubbing through Anna fucking Kendrick’s pink lips.

“Mmmm...much better,” the actress cooed as her fingers fucked her asshole much faster now. “Do you like how it looks?”

“Very much,” Gabe nodded, his shorts tented in front of him for even more confirmation. “Has your ass, um, eased up? You know, enough for sex?”

“You want to?” Anna looked up at him with her big blue eyes, excitement behind them.

“Yes. I very much would love to fuck you,” the trainer agreed.

With the prospect of missing the next 4 weeks of intense physical strengthening, Anna sprang into motion. Flipping back over from sitting on her ass to back on her hands and knees, Anna was ready to receive the trainer’s dick. Gabe was doing his part by pulling down his gym shorts and gripping his erect cock in his hand.

“I have a condom in my locker,” Gabe suggested.

“Don’t bother. But before you sodomize me, get wet in my pussy,” Anna ordered.

Excited that he got to forgo a condom despite it being their first time fucking, the muscular man stepped on his knees within striking distance of the kneeling actress. Though she wasn’t tall at all, Gabe was thankful that Anna had fairly long legs which made their hips level despite their gulf in standing height. Though his cock was dry and she was undoubtedly tight given her slender physique, her pussy was more than wet enough allowing the burly man to have no trouble sliding the first half of his monster cock into her tight pussy in the first push before backing out and sheathing the whole shaft with his next thrust.

“Awwh yes! Oh fuck,” Anna cooed as she felt his dick stretch her out fully.

Gabe felt the exact same way. As the pair both bit down on their bottom lip, the personal trainer reached down and held tightly onto Anna’s slender hips. With his grip secure, Gabe used the slim girl to pull back as he thrust forward, being sure to fuck Anna with every one of his 7 inches but not going to swiftly. After all, he wanted to make sure it felt good for both of them as he fucked her, but not so good that it ate away at his stamina. After all, Anna fucking Kendrick promised him her ass and Gabe was sure as hell gonna collect. 

“God! You feel perfect. So tight, so wet,” Gabe grunted.

Though he was thoroughly enjoying fucking the Pitch Perfect star, Gabe made sure to stay in control and stick with the medium speed. However, even though he hadn’t opened the throttle, with each push into her, Anna’s ass would ripple from the contact while her heavy tits swayed back and forth under her. Unfortunately he couldn’t see her notorious tits given their positioning and her sports bra still on, but Gabe would fix that soon enough. 

“Yes! Fuck me,” Anna moaned, using her arms to rock herself backwards in time with his thrusts. 

Slowing his thrusts but going much harder, the personal trainer reared back and slammed his hips forward with everything he had. Anna whelped in surprise as she was fucked deep and hard, but ultimately it felt good even if she would have been bucked into the wall if it wasn’t for Gabe’s strong hands holding her hips. The petite actress braced for the next blow by spreading her arms and angling them a little higher, but even being more prepared she still required Gabe’s grip from throwing her forward. She was prepared for it the next time he skewered her tiny body with his cock but it didn’t stop her from moaning loudly as a result. 

“Fuck! Feel so good and tight and wet,” Gabe hissed. 

“Easy up, lover boy,” Anna ordered, not for herself but to help the trainer’s stamina. “Don’t want you wasting all your good fucks in my boring ol’ snatch.”

“No risk of that,” Gabe smiled down at the sexy auburn-haired woman. “Are you ready to switch?”

“Yes. I want you in my ass,” Anna all but begged. 

Gabe couldn’t believe the moment had arrived. Though Anna was extremely confident this whole time about taking his cock in her ass, Gabe was still worried he wasn’t going to fit. After all, his cock felt like it was stretching her pussy to the max, and yet Anna’s reputation for being very sex positive around Hollywood was well known. So if her pussy was that tight, Gabe was concerned that her asshole would be all but impossible to penetrate.

“Here,” Gabe said, sliding a yoga mat under her head after he rolled her over onto her back. 

“You’re so sweet. Nothing wrong with a little comfort as I take a cock in the dumper.” Anna replied.

Anna was in for a little surprise when the trainer reached down and seized both her arms below the elbow. The actress didn’t think much of it, even when she noted Gabe holding the purple resistance band in his other hand, the same flexible yet strong band that he’d been using to add resistance during her strength training. With deft handling, Gabe was able to undo the knot in the band, wrap Anna’s wrists in the wide elastic band and form a new knot, having successfully tied Anna’s arms in front of her.

“Gabe! Kink boy,” Anna gawked. “Didn’t know you had some edge to you.”

Usually a woman liked to reach down and spread their cheeks as a dick tried to be forced into their anus, but Gabe had eliminated that as an option by binding her wrists. Regardless, Gabe had a feeling that despite her miniature size, Anna Kendrick would be able to take his cock in her backdoor. After sliding in one finger then a second, the trainer pulled out and noted her asshole gaped open a little. Gabe seized that opening and placed his pee slit right against the dark center and pushed forward. It was more a lean, forceful but slow and even. Given the less than ideal positioning, Gabe didn’t think his dick would enter her ass so easily, but within a moment his tip had forced open her sphincter and was 3 inches deep in her rectum before he stopped.

“There. It’s in,” Gabe comforted.

“Thanks for the confirmation but since I’m the one with their anal ring spread to the limit, pretty sure I knew when you entered my asshole,” Anna retorted.

Despite Anna’s bravado, the trainer decided to take things at an easy pace. As Anna showed no outward signs of pain or even discomfort, Gabe made a few small thrusts into her colon only using the 3 inches already in her. The trainer’s eyes went from watching his thick tool taking baby strokes in the slender actress and looked up at her face, and found Anna wearing almost an annoyed look. Changing tactics, on his next thrust into the actress Gabe went slow but pushed hard, making over two-thirds of his shaft enter her rectum.

“Mhmmm...much better,” Anna cooed from the sudden plunge of her backdoor.

How such a slender creature like Anna Kendrick could take 5 inches of thick cock into her asshole was still a mystery to her trainer, but he wasn’t about to overthink it. Instead, Gabe started to thrust into her with smooth strokes but going much faster than before. As if her asshole was magical, it seemed to stretch perfectly around his dick, making him feel like he could fuck her as hard as he wanted yet it would remain tightly around him as he did so.

“Do you like how it feels?” Anna asked as he fucked her with just over half his length.

Though at the beginning he was taking an agonizingly slow pace, Gabe realized the petite star could handle an actual anal fucking. Thus, the horny trainer was able to pick up the pace. Knowing that Anna was seemingly able to handle anything at this point, Gabe began going faster and faster as he slid almost all of his shaft in and out of her tight asshole. Experimenting slightly, every couple thrusts the trainer added a little extra power to his spears into the Pitch Perfect star’s rectum, causing her tits to bounce within their confines.

“May I?” Gabe asked, his finger curling under her sports bra.

“Fucking my ass isn’t enough? You need to see my amazing tits bouncing as you do so?” Anna scolded before a smile cracked on her face. “Just joking. Yes, of course.”

Gabe didn’t hesitate to lift the elastic bottom of the sports bra up and over her bouncing tits. As her boobs came into view for the first time, Gabe stopped his thrusting due to being mesmerized by the sight of them. Though not the largest he’d ever seen, on Anna’s tiny frame they were made to look huge. Perfectly shaped, firm and yet soft at the same time, her nipples were erect from the ass fucking he had been doling out up to this point.

“Hey dude! I know my boobs are great and all, but I still want to get properly fucked in the ass,” Anna chided him.

“Shit. My bad,” Gabe apologized before getting back to brass taxes.

Though the position with him on his knees with Anna’s heels against his chest and the star flat on her back had several advantages, it also had some negatives. Being able to see Anna’s famous tits bouncing up and down with every thrust into her was a massive plus, as was only being able to use just over half his dick to thrust into her booty. That and the fact he could only go at about a medium pace instead of all out fucking, but this was serving to pace himself so he didn’t blast off in Anna’s rectum too soon. Therefore, the goods were outweighing the bad.

Gabe could have unlaced her shoes and yanked them off all so he could take Anna’s leggings off her legs, which were keeping her thighs pressed together. However, all that would slow him down or make him exit the Pitch Perfect star’s puckered hole, something the trainer had no interest then. Anna wasn’t able to hook her legs around his waist to encourage him further so begging him to do so would have to do. Giving her what she wanted, Gabe grabbed her hips and added a little more power to the thrusting. He still wasn’t moving particularly fast inside her ass but it seemed to do the trick, satisfying her for at least the moment as she closed her eyes and moaned. The trainer was multitasking as he had also drastically picked up the pace of the rubbing on her clit, making Anna moan even more.

“You really do like having your ass fucked, don’t you?” Gabe asked through gritted teeth, shortening his strokes to only half his length but picking up speed. 

“Uhh, yeah,” the adorable actress responded, as her latest boy toy moved his finger from clit to dip into her pussy.

“Ohhh, so tight,” Gabe hissed. 

His teeth were clenched tightly as he drove his cock repetitively in Anna Kendrick’s asshole, but he helped distract himself from the intense pleasure he was receiving by massaging the actress’ tits with one hand while the other was pussy at her snatch. Gabe couldn’t stop a smile from spreading on his face as Anna’s eyes went wide as she added a second finger to the one already making squishy sounds in her dripping snatch.

If the trainer thought Anna felt tight around his cock before, then the statement was only more true now. Her ass had already been squeezing him delightfully but when he added the second finger it got even tighter. It was so tight as a matter of fact, that Gabe was all too aware that he couldn’t withstand for very long. Of course, the fact he was watching the normally adorable face belonging to Anna Kendrick contort in pleasure from having his cock shoved up her ass didn’t help his staying power either.

“Oh god,” Anna moaned as the trainer’s cock slammed into her backdoor over and over.

“Holy crap! You’re gonna cum! From…”

“Sodomy, yeah,” Anna finished for him. “And yes, yes I am. As long as you keep fucking my ass so good.”

Gabe decided to take a chance and slowed his thrusting down, but the trade off allowed the trainer to push all the way into her ass with all 7 inches of thick cock. Gabe felt justified in his choice as Anna let loose her biggest scream of pleasure yet, in fact gabe was a little worried it would bring people running to their location. He went back to shorter strokes but when no knocks arrived at their door, Gabe went balls deep back into Anna, all while his fingers on one hand plunged into her pussy while the other hand kneaded her tits.

“Almost there,” Anna shared, recognizing the familiar feel of her climax building.

Wanting to push her over the edge, Gabe pulled out his little ace in the hole, or at least what he hoped was. Moving his hand reluctantly from feeling up her great tits, the trainer swapped hands, before moving the hand that had been finger blasting her cunt forward until he could reach her mouth. When Anna’s mouth opened for her next moan he pushed two fingers between her lips, making her scream when she tasted the combination of fresh pussy juice and the subtle hint of her ass from when he fingered that hole awhile ago yet still clung to his digits.

“Ahhhhh,” Anna suddenly squealed around the fingers in her mouth as the combination of cock fucking her ass, fingers in her pussy, and his filthy fingers in her mouth pushed her over the edge.

Knowing he would be with Anna Kendrick in tight clothing, earlier today Gabe masturbated so he wouldn’t have any trouble from an unwanted boner during their session. He couldn’t have been luckier to have done so now that he wound up fucking her, therefore making him in no danger of cumming again, even from Anna’s super tight ass threatening to rip his dick off. So he kept right on drilling the star’s ass, albeit at a slower pace to keep from letting Anna’s super tight ass actually rip his dick off.

“Dammit Gabe. High five,” Anna cooed, lifting both arms as a result of the band holding her wrists together. “Hell of an ass fucking you gave me.”

“And it’s not over yet,” the trainer grinned down at her.

“Well flip me over so you can actually go hog wild in my booty,” the actress said with a smile.

Initially it was laziness that stopped Gabe from either untying her hands or pulling off her pants completely, but now we got an extra thrill out of seeing the petite star so...helpless. Quickly weighing his options, the trainer found that simply tipping her onto her side allowed for a lot of benefits with almost no downsides. Though he had to stay on his knees to sodomize Anna, the yoga mat he knelt on was comfortable. Meanwhile, Anna on her side meant her ass looked more appetizing and he still got to watch her fantastic tits bounce about as he plunged the depths of her bowels.

He did have to pull out of her for an easier transition, but as he saddled up behind Anna he found his cock slid back into her magical asshole with barely any fight. His first handful of thrusts were with only half his length, but from there he started going a little deeper and then a little faster. Never going more than an extra half-inch at any given time, it still took only a few minutes until Gabe was fucking Anna Kendrick in the ass faster than any time previous and with all 7 inches.

“That’s it, big boy,” Anna cooed from the ground. “Give my ass that pounding it deserves!”

Never doing the same stroking technique for too long, gabe kept things changing for both their sakes. For Anna, it seemed the cock-hungry girl loved variety while for him, it stopped him from nearing his own climax. Going from a fast, balls deep pace, Gabe both slowed it down and reverted to only using his tip plus an inch or two to fuck Anna’s ass. After another minute he delivered one sharp thrust deep, forcing the Pitch Perfect star to take all 7 inches again at one time, before backing out and resuming a medium pace with only half his shaft.

“Do you like how my ass feels around your big dick?” Anna spoke the dirty words with an innocent expression on her adorable face.

Gabe responded by producing half a dozen thrusts into her tight ass in barely the blink of an eye. Only the final thrust, Gabe pushed and pushed until fully sheathed in the tiny actress. Letting his dick soak in her ass, the trainer reared his hand back then delivered another spank to her booty, making the white skin go red once more. Expecting him to change his thrusting pattern, Anna was surprised when he pulled out so only his tip held her sphincter from closing before slamming balls deep into her backdoor again. And again. And again.

“Can’t believe how good it feels going this deep in your ass,” Gabe grunted as he pummeled Anna Kendrick’s ass once more.

“Really know make a girl...ahhh...blush,” the actress retorted, biting her bottom lip.

Anna was clearly enjoying being actually fucked deep and hard as she liked because the pint-sized actress was rocking her body back to meet his thrusts. She wasn’t able to push back with any great force given how her legs and wrists were bound, not to mention being on her side like that, but her rocking on the floor acted to grind his cock in new ways, greatly amplifying his pleasure, and by the sounds of her moaning, Anna’s as well. Feeling his orgasm getting closer by the second, Gabe needed to release some pressure so he pulled out of the tight confines of her booty.

“I want to see what your ass looks like,” the trainer said as cover for stopping.

“Gabe! Who knew you were so naughty,” Anna said with a wide grin.

Anna had so many partners in the past that having a guy, or girl for that matter, look at their handiwork after destroying her ass was no longer a new thing. Feeling his cock leave her pooper, the petite actress did her best to relax her anus and leave it open for him to look down into the abyss of her brown eye. Surprising her a little, after complimenting her, Gabe actually lent down further so he could spit a wad of saliva into her asshole for more lubricant.

“Is it big?” Anna asked, once more making it wink so it opened a little wider. 

“We can make it bigger,” Gabe commented.

Anna scrunched her face confused by his comment but before she could ask for clarification, Gabe was ramming his dick all the way then backing it out. Anna yelped in surprise as her bowels were poked then emptied of dick, and sure enough she could feel an even bigger breeze blowing against the inside of her gaping asshole. Gabe felt it was bigger as well, especially after he performed this neat little trick 3 more times until Anna felt like she was spread wide open.

“You like how the inside of my bum looks, you little perv?” Anna asked her latest boy toy.

“So much,” Gabe said.

Anna let him do so another few times before having to put her foot down. “Enough fooling around and fuck me already. I wanna drink some cum ASAP!”

With those rather slutty words out of her mouth, Gabe lost the ability to regulate himself. All that mattered to him now was giving Anna Kendrcik exactly what she wanted. Luckily, what she wanted and what he wanted aligned perfectly. Reaching down with his strong hand to clutch onto her topside hip, Gabe used his strength to pull her slender booty back to meet his thrusts. With every thrust into her ass, Gabe sheathed fully in her rectum, causing her booty to ripple and tits to jiggle with each blow. 

“Gonna cum for me big guy?” Anna all but begged.

“Close,” Gabe replied, working up a sweat as he fucked her ass harder.

“I want it. I want all that cum in my mouth,” Anna urged, her asshole being absolutely destroyed at this point.

“Gonna drink it all down?” Gabe hissed, his thrusting becoming more erratic.

“I’m so thirsty Gabe. Give me something in my mouth,” Anna played along.

“Yeah? Want my cum. Fuck! Then take it!” 

Anna timed his thrusting just right so that as Gabe was rearing his hips backwards she scooted as far forward as she could. The result was as she planned with his dick popping free of her poop chute. Like a well-oiled machine despite this being their first time fucking, just as Gabe crawled towards Anna’s face, the petite actress was already under him and his dangling cock. Being the little butt slut she was, Anna didn’t even hesitate to open her mouth and wrap her lips around the head of his cock.

“Mmm,” Anna moaned, tasting her own ass on his cock.

It was so nasty and naughty but that was why she always did it, or did it for most of the good ones. Anna really got off on being such a depraved little slut, letting any guy she felt like fuck her in the ass and then sucking his cock clean whenever they wanted. Seeing the lust and hunger in Anna’s eyes, Gabe put a hand on the back of her head. Though Anna needed no encouragement with blowjobs, the trainer was too wrapped up in the moment and began thrusting his hips, fucking her mouth, pushing in until he felt his cock brush against the back of her mouth before she pulled back. When just the head of his cock was still in her mouth, Gabe looked down and saw the big gorgeous eyes of Anna begging him to give her the just rewards she wanted.

“Fuck,” Gabe grunted as he emptied his balls.

The first jet squirted out and hit her along the entirety of the length of her tongue. The second blast followed right on its heels and hit her on the roof of the mouth. As his orgasm wound down and his cum was becoming less in terms of volume and the force it was propelled out, Anna took over and sucked the rest out of Gabe all without ever breaking eye contact with him. Even after the last drop of cum had left his balls, Anna continued sucking more of his cock, albeit at a slower less aggressive pace. When just the head of his cock was still in her mouth Anna sucked on the head and swirled her tongue around the crown before pushing back in as she went back to cleaning his cock of all remaining ass juices and jizz.

“Mmm hmm,” she moaned, finally letting his spent cock slip from her mouth when she was sure she’d gotten all of it.

“Jesus,” Gabe finally groaned after a few silent seconds. “That was…you were amazing.”

“Me?” Anna questioned, reaching her arms forward for the trainer to undo the knot. “You made me cum while sodomizing me! Not an easy endeavor. Thanks dude!”

“Oh well you’re welcome,” Gabe smiled.

“So we have another 3 or 4 weeks, right?” Anna asked, straightening up.

“Yeah. 4 weeks, 6 days per week,” Gabe answered, unable to keep the smile from his face.

“Cool. I’m gonna go shower. Just let me know if you wanna bring a friend to our session. I’m totally cool with that. Guy or girl.” Anna added. “Later Gabe.”

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