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Stories & Art => Celebrity Stories => Celeb Series Stories => Topic started by: YoungDubz on December 28, 2023, 05:22:50 AM
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===DISCLAIMER===
This is a work of erotic fiction.
The person(s) portrayed in this work are over the age of 18.
This material should not be viewed by any parties under 18 years of age.
Copyright: YoungDubz 2023
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Chapter 1: Emma Watson's Idea
Jake Bryce sat in the bar at the New York Hilton at 20:30 on a Friday evening, thinking how much he loved his job. He knew he probably shouldn’t, and that he should feel some semblance of shame from what he did, but he didn’t.
Jake was a gigolo and proud of it.
He knew he was an attractive man, and his workout regiment had helped him maintain a svelte but muscled body on his 6’3 frame. If women wanted to fork out cash to spend an evening with him, who was he to deny them that?
He was sat, waiting for a client to arrive. He wore his usual attire of a dark blue suit with a black shirt. He’d been given the instructions by his agency to sit in a specific seat at a certain time.
Jake picked up the drink he’d ordered and was about to take a sip when he was approached by what was clearly a bike messenger.
“I believe you’re waiting for someone, sir?” Said the man. “Umm, yes, I am” said Jake, somewhat confused “It’s not you, is it?”
“No, someone asked my company to deliver a message to someone sitting in this seat at this time. Room 576.” Said the messenger.
Jake seemed to understand what this meant. Sometimes, these things involved an element of secrecy or anonymity. “Oh, right, okay. Message received.” He told the messenger, who turned and left, the other patrons eyes watching him as he did.
Jake finished his drink, settled his bill and left the bar. He walked to the elevator and rode it up to the corresponding floor.
He wandered the corridors, looking for Room 576. Once he found it, he knocked.
He looked down at his feet, and saw a keycard he slid under the door with a post-it note on it saying “30 seconds, then come in”.
He picked up the keycard and looked at his watch. Once 30 seconds had passed, he unlocked the door and went inside.
Jake found himself in what appeared to be an empty room.
“Hello?” He asked, walking past the bathroom door further inside, now fully in the room. He looked and moved toward the window, unaware that the bathroom door had opened and someone had stepped out.
“Well, aren’t you a strapping young chap?” Said a female voice with a British accent.
Jake turned around and his eyes widened in surprise.
Before him, in a lacy red two piece lingerie set was Emma Watson. Her long hair was down at her shoulders, slightly covering her breasts in the see through bra she wore.
“Wow” exclaimed Jake, once he’d found his words “I can’t believe this. I’d never have thought someone like you would be doing this kind of thing.”
“What, you don’t think I know how to get dirty sometimes?” Said Emma, putting extra emphasis on the word ‘dirty’ as she moved toward Jake.
“No, it’s not that, I just would’ve expected one of the most beautiful women in the world to not have to resort to hiring a man for the night. You could have any man you wanted.” Explained Jake, the sight of the former Hermione in that lingerie causing his penis to slowly get harder and harder.
“You’re right. I could just go down to that bar, walk up to the first man I see and tell him to fuck me senseless and he’d do it like that” said Emma, snapping her fingers “but that’s not good press if it got out that Hermione Granger was strolling about looking for random cock, is it? No, I need something that would allow this whole evening to remain between ourselves so I can get what I’m so desperately craving. I’ve been at the UN all day and I have to cum soon. I need something that my fingers or a dildo can’t give me. How about you, big boy,” Emma asked, indicating the visible bulge in Jake’s trousers “can you give me what I need?”
With that, Emma got onto her knees, and started to undo Jake’s built, unzipping his fly and pulling his trousers down to his ankles. She felt his hard cock through his boxers, and pulled those down to free his throbbing erection. “Oh fuck, you ARE a big boy, aren’t you?” Gasped Emma, moving her hand up to Jake’s penis. “This has got to be what, 7, 8 inches at least?”
“About that” smirked Jake, who was already restraining his orgasm as Emma Watson slowly jerked him off.
The girthy penis twitched in Emma’s hand as she rubbed up and down the shaft. The beautiful English actress smiled to herself, thinking how good this would feel inside her tight pussy, stretching her and filling her ever so well.
“Before we do this, just to check, you’re clean right?” Asked Emma.
“Tested every month, all clear” responded Jake.
She moved her face closer to the thick cock of the man she just met, looked up at its owner and maintaining eye contact took it in her mouth.
“Oh fuck, that feels incredible!” Groaned Jake, as he watched Emma take more and more of his cock in her mouth, only pulling up to breath, then getting back to it, working the entire length into her mouth until her nose rested against his pelvis.
Emma reached up and grabbed Jake’s hands, guiding them to the back of her head. Jake didn’t need to be told twice.
He grabbed onto Emma’s hair, and started to thrust himself back and forth, his cock pushing into her throat each time he thrust forward.
All Jake could hear were the wild gluck sounds coming from Emma, who had moved her hands down to grab at her breasts and play with her now dripping wet pussy.
Jake knew he’d not last much longer, so he started to ease off. Emma had other ideas, she grabbed Jake’s ass and pulled him into her all the way. Her tongue licked the underside of Jake’s cock as he lost control and emptied his balls deep in her throat. She kept him in her mouth until Jake confirmed he was finished, then she pulled herself off of Jake’s penis, not letting one drop escape her mouth. She made a show of swallowing for Jake then showing her mouth was empty.
Eyes wide with lust, her makeup smudged and spit flowing out of her mouth from the frantic face fucking, Emma looked up at Jake. She went over to her bag on a nearby chair, and took out a pill bottle. She threw it at Jake.
“Take one, then round two. You’re gonna fuck me with that big cock!” She demanded, moving to the bed, Jake watched her tight little ass swaying as she moved, the thong of her underwear nestled enticingly between her cheeks. He took out a pill and popped the it, then followed behind, shedding the rest of his clothes. Emma reached behind her, unclasped her bra and exposed her perfect, perky small breasts to Jake. He held Emma close, kissing her deeply. Their tongues danced, then Jake moved to latch his lips to Emma’s nipple. He sucked and nibbled on one before moving to the other.
Jake’s hands, meanwhile were occupied with Emma’s lower half. One gripped the firm cheeks of her ass, while the other rubbed Emma’s pussy through her panties, causing the English beauty to moan, her own hands running through Jake’s hair, pulling at it as she felt the pleasure course through her.
Jake raised his head, kissed Emma again, then turned her around and pushed her onto all fours on the bed, he got on his knees behind her and pulled her panties aside in order to get at her drenched pussy.
His fingers ran along the length of her slit, collecting the gathering juices. Jake raised his fingers to his mouth, and he got his first taste of the British beauty. The sweet but tangy flavour hit his tastebuds and he immediately had to have more. Lowering to his own knees behind Emma, he started to lick at her pussy, causing the brunette to moan in pleasure.
“Fuuuuck yesssss, eat me, you fucking stud. Get my pussy wetter to take your cock inside.” Emma groaned in pleasure.
Jake licked Emma’s pussy, then moved slightly downward to suck on her swollen clit. He replaced his tongue with his fingers, rubbing her wet pink pussy lips, spreading them open then pushing two fingers inside.
“God, fuck, fucking finger my tight little cunt. Finger my twat till I come over your fingers. Feels so good, make me cum, I fucking need it. Make me cum then fuck me. Do what you want you fucker, making me feel fucking amazing!” Screamed Emma, drunk with ecstasy now.
“Customer’s always right” thought Jake, who quickened the pace of his fingering of Emma’s pussy with one hand while the other groped and grabbed her ass. His fingering pace actually quickening, his digits inside the gorgeous Harry Potter actress’ pussy feeling around until they found her G-Spot. Jake curled his fingers and pressed against the spongy texture, causing Emma to go wild with lust. “Fuuuuck yes, you fucker! Shit, you’re making this feel amazing.” Groaned Emma, her orgasm getting closer.
Jake knew Emma was close, and knew how he wanted to push her over the edge.
“Reach back and spread your ass for me.” Commanded Jake, Emma immediately obliging.
Jake gazed in wonder and awe as Emma Watson’s puckered little asshole was exposed to him. It looked virtually untouched, but Jake figured if Emma Watson was able to take a throatpie without any hesitation, anal play was probably easy street for her. He moved forward, tongue out and took his first lick of Emma’s little starfish.
“Oh God, yes, eat my ass. I love it. Fucking rim me while you finger my cunt. Oh god, I’m so close, shitfuck, yesssss” moaned Emma as she was pushed over the edge,, her orgasm coming thick and fast. She screamed in pleasure as she rode the waves of her ecstasy.
Jake kept up his actions through Emma’s orgasm, tongue pressed into her asshole and fingers rapidly penetrating her pussy, his hand covered in her juices.
Emma’s climax subsided, and she collapsed onto her front on the bed. Jake stood and stared at the beautiful woman trying to catch her breath. The pill Emma gave him was working and his cock was fully erect again. He moved over, and removed Emma’s panties.
With Emma still lying on her front, Jake parted her legs, and positioned himself so his cock was rubbing at her entrance. He felt Emma shift her hips, as if trying to get the cock inside her.
Jake obliged, and pushed his full length slowly but surely into the actress’s vagina.
“Fuuuuck, you’re so tight” moaned Jake, beginning his thrust back and forth.
“Mmm, that’s nothing, wait till you feel my ass!” said Emma, smiling dreamily as Jake started to fuck her harder. “Mmm, fuck, that feels so good, you’re so deep!” Moaned Emma.
Jake moved his arms and wrapped them around Emma. He picked her up, turned around and fell to the bed, his penis remaining inside her.
Emma got the idea, and started to ride him, writhing her hips as she rode Jake in the reverse cowgirl position. Jake’s hands moved up to cup Emma’s modestly perky B cup breasts, pinching the nipples and making her squeal with pleasure.
Emma had one hand running through her own hair, the other behind her, resting on Jake’s chest to stabilise herself.
Jake was enjoying his view, the gorgeous brunette’s perfectly sculpted ass bouncing up and down on his pelvis. He moved his left hand to his mouth, and sucked on his thumb, then reached down between the tight cheeks of the former Hermione.
He ran his thumb down toward her little asshole and spread his saliva around, causing Emma to slightly tense, her pussy contracting wonderfully around Jake’s cock.
Still bouncing on the penis filling her spectacularly, Emma Watson looked back at Jake.
She chuckled. “Already? Is my pussy not enough for you? My little English muffin not making this big cock feel good enough?” She asked, her voice dripping with arousal.
“No, no. it’s perfect” replied Jake “Don’t get me wrong. It’s just, you have the most beautiful little asshole I’ve ever seen. I just have to do this.” As he said this, he pushed his thumb inside.
Shit, that feels good” moaned Emma. She stopped riding and pulled herself off Jake’s cock.
She threw herself back on the bed, and raised her legs in the air, then moved one hand to her pussy, and other to her asshole, and slid a finger inside both.
She motioned to a bedside table. “Top drawer, there’s a bottle of lube, get it!” She instructed Jake.
Jake did as he was told. He got the bottle of lube, opened it and squeezed out a good amount into his hand, which he then rubbed onto his cock.
He moved back over to Emma, and squirted some more out onto her pussy, which she then rubbed into her pussy and down to her asshole, using two fingers to slide inside.
Jake positioned himself, the tip of his cock close to her hole. He watched for a minute as Emma went two then three fingers deep in her most taboo of holes, then she removed her digits nd grasped his cock. She pulled him closer, lining his cock up with her asshole.
“Do it, big boy” said Emma, through gritted teeth. Her hair a mess from sweat and makeup still running from her expert blowjob earlier, she looked unrecognisable from the prim and proper lady you’d have seen on the red carpet or at the UN giving a speech. Now, Emma Watson looked like any random pornstar after a long gonzo shoot.
Jake pushed forward, his hard cock entering Emma’s forbidden hole. He barely got the first half inch in before he felt resistance, and he heard Emma whimper. He looked at her and she was grimacing slightly.
Jake thought about stopping, he remained still inside Emma, contemplating pulling out.
Emma sensed his hesitance. “It’s okay. It’s always like this. First part always hurts but keep going, I’ll be alright” she said softly.
Jake started to thrust forward again slowly. With each thrust, he got a little more in each time, until he soon got his entire 8 inches inside the beautiful actress.
He remained still, allowing her to acclimate to his length inside her. He grabbed the lube bottle and emptied it more onto his cock, using his hand to rub more around her hole gripping his shaft.
Emma gave a slight nod, having adjusted to his cock inside her ass, and Jake started to fuck her tight asshole.
Jake was in heaven. He looked down at his cock entering the asshole of Emma Watson, then his eyes scanned upwards, and he looked at the angelic vision of Emma’s breasts bouncing in time with his thrusts, then to her face, contorted in ecstasy. She had one hand at her mouth sucking on her fingers, the other hand rubbing along her stomach and breasts, which she then moved to start circling her clit with her fingers.
He watched her play with herself and kept up his pace, giving Emma the ass fucking she desperately wanted.
A couple of minutes went by like this, with Emma mostly moaning her enjoyment with no actual words, accompanied by Jake’s groans as he felt himself getting close to his own orgasm which he held off.
“God yes, feels so good in my ass. You’re gonna make me cum from fucking my tight little asshole.” Screamed Emma.
Jake knew he was close to orgasm himself.
“I’m getting close” he warned Emma.
“Don’t stop, just a bit more” moaned Emma, who slid two fingers into her pussy for extra stimulation. “Fuck, yes, please, fuck my ass, make it gape, please. Cum when I do, please. Fill my fucking ass with your load, make it drip out of me while I finger my fucking cunt.” Begged Emma, now pistoning her fingers in and out of her pussy, having added a third.
Jake sped up his thrusts, knowing one last big push would finish both him and Emma.
“FUUUUCK, YOU HANDSOME FUCKER, POUND MY FUCKING ASS LIKE I’M SOME RANDOM SLUT” shouted Emma. Her floodgates broke and she came with a huge scream. “YEEEESSSS, I’M CUMMING!” she shouted as she squirted her orgasm right into Jake, whose own resistance gave way and he started to cum himself, his load shooting directly into Emma’s asshole. “OH FUUUCK”, he groaned as the actress’ tight asshole squeezed every drop out of him.
As their respective orgasms subsided, Jake pulled his cock out of Emma’s asshole. He watched as the stretched hole gaped for a brief moment, then closed up, slightly red from the hard fucking he had given it.
Jake collapsed on the bed next to Emma, who turned to him and rested her head on his chest.
After a couple of minutes in silence, she spoke first.
“You know, I’ve got some friends who’d just love you” she said.
Jake raised an eyebrow. “What?”
“I have friends. Hollywood friends, anyway, who are always on about needing a good shag. Maybe you should go private, exclusive clientele, you know” said Emma.
“Not through the agency?” Asked Jake?
“I mean like, get a dedicated number, a second phone or a burner, is that what they’re called?” Said Emma, “and the number can only be given by someone who has it.”
“And how would I get the number to someone in the first place?” Quizzed Jake.
“Tell it to me” said Emma, who rose and walked to a desk with stationary. She wrote something on a piece of paper and went and put it in Jake’s jacket pocket.
“There, now when you go and get your burner or whatever, text me the number and I’ll pass it on”, explained Emma.
Jake chuckled. “So, are you my pimp now?” He joked.
Emma laughed. “No, I’m more an…intermediary, or a starter point. I’ll give the number to one or two of my friends, and they can pass it on from there.”
Jake thought on this for a minute, but he soon started to feel tired.
“I gotta go” he said, standing up from the bed and moving to his clothes. He gathered them up. “Can I use the bathroom quick?” He asked Emma
She smirked on the bed. “I need to take a shower” she said, as she rose from the bed herself. She walked past Jake, and knocked the clothes out of his hand as she did so. “Care to join me, Stranger?” asked Emma who then opened the bathroom door and leant on the doorframe, seductively.
Jake looked at the vision before him, and followed Emma into the bathroom. “Of course. And it’s Jake, by the way.”
*****
Jake awoke the next morning in the hotel room, alone.
He looked around and besides his own clothes bundled on the floor, there was no evidence of Emma having been here.
He rose and went to the bathroom, actually intending to shower this time without the distraction he had of Emma Watson sinking to her knees in front of him as the water poured down and deepthroating his cock for a second time before demanding he fuck her over the bathroom sink and finishing on her breasts.
He’d gone back to bed and went straight to sleep following that.
Jake showered, then put his clothes from last night on.
He checked his pockets that he had everything, and found the note Emma wrote to him. On it was a phone number and a message:
‘Send me your private number’.
With the note, Jake also found in his pocket a Polaroid photograph he hadn’t taken but Emma clearly had taken in the bathroom mirror, her body fully nude, her beautiful smile radiating and one hand rubbing at her pussy.
On the back was another message:
‘For the memory. X’
Jake smiled and left the room, immediately heading to the nearest electronics shop and purchasing a prepaid cellphone. He text the number Emma had given him.
‘It’s Jake from last night, here’s my new number’.
He went about his day, almost forgetting about his new second phone, until two alerts came through.
One was a reply from Emma, saying ‘Thx for last night. Given number to friends. Until next time ;) x’
The other alert simply read ‘Hotel Edison, Room 750, 19:30.
He text back ‘Confirmed. Pay by cash, £500’.
===To Be Continued===
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Chapter 2: Karen Gillan's List
Jake arrived at the Hotel Edison just after 19:25, again in his dark blue suit with a white shirt, open at the collar with no tie.
As he approached the front desk, his new business phone vibrated in his pocket. He took it out and read the message he had received.
‘Change of plans, go to the bar. Sit by the furthest window, I’ll come to you x”
Jake shrugged. A sudden change of plans was par for the course in his line of work.
He went to the hotel bar, ordered a scotch on the rocks, and took it over to a seat near the furthest window, as instructed.
He sat for a few minutes, sipping his drink and watching the entrance to the bar. He soon spotted the person he assumed was his client for this evening, the beautiful and leggy redhead star of the Guardians Of The Galaxy movies, Karen Gillan.
Wearing a figure hugging black minidress that barely came past her hips, putting almost every inch of her long gorgeous legs on display. On her feet were a pair of 4 inch heels.
She looked around from the entrance, stopping when seeing Jake sitting in the seat he was instructed to occupy.
She strode confidently over to his table, heels clicking on the floor as she walked toward Jake, pulling something of a handbag she held on to as she did.
When she reached Jake’s table, she bent down to Jake and whispered in his ear “meet me in the men’s toilets, 1 minute”. She took his hand and passed something fabric to Jake.
She straightened up and continued her stride toward the bathroom area of the bar, through a set of doors at the wall near to where Jake was sitting.
As he waited, Jake looked at what Karen had handed him. He unfolded the square of fabric, and saw with wide eyed surprise that it was a pair of black silk panties, the crotch area clearly wet from recent arousal.
Jake rose from his seat, and followed after Karen, stuffing the panties into his pocket as he stood.
He entered the men’s room, and was silently thankful there was no attendant on duty. He whispered “Karen” and saw the door of the end stall move slightly and a hand poke through the gap, one finger beckoning him nearer.
He walked over and inside. As he did, Karen grabbed him and kissed him deeply, their tongues intertwining as she reached over to lock the stall door.
Jake was the first to break the kiss, and whispered to Karen “You wanna fuck right here?”
Karen chuckled, and whispered back softly in her Scottish accent “I’ve got you all evening, laddy, this is just the start”, grinning as she took Jake’s hand and bought it between her legs and letting Jake feel the warm wetness of her pantyless pussy.
Jake started to rub Karen’s wetness along the lips of her pussy with his fingers, while softly pressing her clit with his thumb.
Karen moaned and grabbed Jake’s neck to pull him in for another kiss. As their tongues danced, Jake’s fingers started to rub Karen’s pussy faster, causing the stunning redhead to moan more into his mouth.
Jake again was the one to break the kiss, and pulled the panties out of his pocket, and brought them to Karen’s mouth. She eagerly parted her lips and as Jake was stuffing the ruined silk underwear into her mouth, he slid two fingers inside of her pussy.
“Oh fuck!” groaned Karen, her voice now muffled by the improvised gag Jake has put in her mouth.
He moved his arm to her waist, holding her up while the other hand started to frantically finger the former Doctor Who actress.
Jake kissed Karen’s neck and collarbone, then he rasped into her ear “Is this what you like? Two fingers in your wet little cunt in a public place? You’re just a little slut, aren’t you?”
He quickened the pace of his fingers, the leggy beauty moaning with pleasure as he did, her orgasm getting closer and closer.
Though said quietly and muted further by the fabric in her mouth, Jake could still make out the pleading words coming from the Scottish stunner. “Please, Jake, make me cum, please” begged the Marvel star.
“Cum for me. Cum on my fingers like the slut you are” growled Jake into Karen’s ear, as he pushed his fingers as far inside her pussy as they would go.
Karen’s restraint broke and she came deeply, soaking Jake’s hand as she did.
“Fuck yesss, I’m cumming so good for you, oh gooodd, yes!” moaned Karen, panty gag still in her mouth. Her body shook as she came, but Jake still had a hold on her waist, keeping her upright still.
He took the panties from Karen’s mouth, and the pair kissed deeply again, the last of Karen’s orgasmic cries leaving her mouth and directly entering Jake’s.
He held her in the bathroom stall for a couple of minutes after her orgasm, to allow her to get herself under control. He also stuffed her panties back into his pocket.
Once Karen had recovered herself, she straightened herself up, adjusting her dress to cover her modesty and hide potential evidence of the last few minutes. She took Jake’s hand, covered in her cum and licked every inch clean.
“That was amazing” she said to Jake, as she unlocked the stall door.
She gave Jake a peck on the cheek, and took his hand. They left the men’s room together, neither caring as they walked out of the stall. They’d been lucky, no one had come into the bathroom as they were in progress, but as they left the bathroom, there were two men walking in.
“Hi boys” said Karen, waving and blowing them a kiss as she did so, then continuing to lead Jake away.
She walked them both outside the hotel and to the street.
There waiting was a white stretch limo. Jake opened the door toward the rear end and held it while Karen got inside. He followed after, and as he sat down, he saw Karen down near the partition, telling the driver something in hushed tones he couldn’t quite make out.,
He heard her say "Thank you” to the driver, who raised the partition separating them from the passengers in the back and head back toward the rear seat where Jake was sitting and she cuddled up against Jake’s chest, one arm around his shoulders and the other down on his legs, her hand slowly rubbing his hardening cock.
Karen moved her head to whisper into Jake’s ear. “You think I should suck your cock right here in the back of this limo? Would you like that? Ooh, I think I have an answer already” said Karen, smirking as she felt Jake’s cock twitch inside his pants.
Jake tried to keep his composure. He was about to answer back, when Karen started to undo his belt and pants, pulling them down.
Karen rubbed the growing bulge in Jake’s boxers.
“My, my. Emma wasn't lying about this, was she? You are well equipped, aren’t you?” Purred Karen, moving herself so her face was rubbing on the fabric covered cock.
She sucked on Jake’s penis through his boxers, used her hands to cup and tickle his balls as she did.
“Oh god, that feels good” groaned Jake, losing control. “Fuck. Just do it, suck my hard cock.”
With that, he took over slightly, pushing down his own boxers and freeing the thick 8 inch member between his legs, Karen’s face being hit as it sprung upwards.
Karen gripped the shaft of Jake’s cock and softly kissed the engorged head before licking her way down the shaft and back up, taking the head in her mouth and sucking in it.
Jake’s eyes rolled back as Karen Gillan teased and tongued his cock slowly and with precision, as if she knew exactly the right spots to focus on and when.
Karen halted her worship of Jake’s hard cock to reposition herself, kneeling on the floor of the limo in front of Jake. She pulled her dress down, revealing her small perky breasts to Jake, her pink nipples visibly hard with arousal.
She took Jake’s cock back in her mouth, and continued the blowjob. Karen knew her limits, but she still tried to take as much of him into her mouth as possible, her gag reflex halting any progress at the halfway point.
Instead of trying to deepthroat, Karen resorted to an old standard that had served her well in her early modelling days. She took as much of Jake’s cock in her mouth as she could, and started to hum.
“Oh my god” groaned Jake, the vibrations stimulating his penis in a way he’d never felt before. His head dropped back against the seat as he felt soaring waves of pleasure approaching.
Then Karen stopped suddenly.
Jake looked back toward her, a questioning look on his face. She giggled and smiled at Jake. “Sorry, but there’s something else I want to try. Give me a second” said Karen, who sat back on her ass on the floor of the limo and moved her long smooth legs in front of her and kicked off her shoes.
She moved her now bare feet onto Jake’s cock, and placed one either side of the erect member.
Getting the idea, Jake pushed the feet together around his cock, and started to thrust, the soft soles of the former Amy Pond feeling like silk against his cock.
As Jake used her feet like a sex toy to jerk his cock, Karen leaned back and pinched her own nipples.
Since stumbling upon a foot fetish website one evening, Karen has been very curious about the sexual appeal of feet.
From the noises Jake was making as he jerked his cock between her soles, this was clearly working, and she spoke up to encourage him.
“That's right, baby, use my feet like they’re my tight little Scottish cunt. You’ll have the real thing soon enough, lad but I want you to cum on those pretty feet first, aye? Don’t you want that? Look how pretty they are? I had a pedicure tonight especially for this and I want you to ruin it. Go on, shoot your load all over my wee toes, you know ya want to. Cum for me, lad. Spray my feet with your spunk.” Growled Karen, licking her lips as she looked at Jake, eyes blazing with a lustful fire.
“Fuuuuck, gonna cum. Gonna cum over your feet, shiiit” moaned Jake, as his orgasm took hold. Just before he came, he positioned both of Karen’s feet on the floor of the limo in front of her, and aimed his cock at them.
A number of sprays of cum shot out of his cock, mostly hitting their target of Karen Gillian’s feet, some of the load hitting the floor instead.
Once Jake was finished cumming, he sat back, his softening cock twitching. Karen spun around on her ass, her face now near to his cock while her legs faced away. She took Jake’s semi-hard penis into her mouth to clean it off, licking all the remaining cum off the head and giving it a suck for good measure just to make sure.
Spinning back around so her legs were again nearest Jake, she looked him directly in the eyes as she moved one foot up to her mouth. She licked all of Jake’s cum off one foot, then did the same to the other. Then she swallowed it all, opening her mouth wide to show Jake she hadn’t wasted a drop.
Her feet now clean of cum, she put her heels back on, pulled her dress back up and sat back on the rear seat of the limo next to Jake, who had pulled his boxers and pants back up and squared himself away.
“That was incredible” muttered Jake, slightly breathless from the last few minutes.
“And we’re not done yet, big boy!” said Karen, as the limo came to a stop.
Jake looked out of the window, and looked back puzzled. “We’re back at the hotel? I thought we’d be going for dinner?”
“Why? I just ate, and you’re about to, once we get to the room.Let’s go” said Karen, smiling as she again took Jake’s hand, both got out of the limo, into the hotel, over and into the elevator and up to Karen’s floor.
They entered Karen’s room, and fell into another passionate kiss. They started to undress each other, Karen’s dress being pulled off completely, Jake’s pants and shirt being discarded, all clothing scattered on the hotel room floor as they moved over to a nearby couch.
Karen broke the kiss, and lay back, spreading her legs to show Jake her wet pink pussy, almost completely bare, only a small triangular tuft of red hair visible above the slightly parted pussy lips, tantalisingly close to the swollen clitoris peeking out at the top of Karen’s pussy.
“Eat me, big boy!” said Karen, her fingers rubbing her wetness. Jake knelt down, and started to lick at the stunning redhead’s wet pussy.
“Mmmm, yesss, that’s incredible” purred Karen, and Jake’s tongue pushed into her tight, pink wetness.
Jake licked away at Karen’s pussy, alternating between poking his tongue into her hole and licking up and down the length of wet lips. On occasion, he’d give her little clit a few quick tongue lashes, causing the beautiful redhead to squirm excitedly.
“Feels so good” moaned Karen, her orgasm getting nearer. “Keep going, I’m nearly there!”
Jake did as he was encouraged, increasing the pace of his licking. Karen’s long legs squeezed either side of his head, feet licking together behind his back.
“Gonna fucking cum!” Moaned Karen loudly, as her orgasm overtook her.
With Jake’s head firmly held between her thighs, Karen’s hips bucked wildly. She thrashed about on the sofa, screaming as the pleasure surrounded her.
Jake struggled to free himself as Karen thrashed, managing to pull his head from between her thighs.
He’d stopped the stimulation with his tongue, and as Karen bucked her hips, he grabbed her legs. He parted them, pushing them up toward her head as if folding her in half, then he pushed his erect penis into her still orgasming cunt.
He started to fuck Karen, causing her to have an immediate second orgasm.
“Shiiit, I’m cummiiing again, fuuuuuck! You’re fucking incredible!” She cried at Jake as he thrust into her, almost relentlessly as if wanting to find out how many times Karen could cum.
This was the thought that occurred to Karen, and she still had things she wanted to try
Her body still reeling from her second orgasm and hearing for a third, Karen put her hands on Jake’s chest as if to wordlessly say “stop”, the insanely passionate thrusting into her pussy ceasing at once.
“I don’t want you to come just yet” said Karen, giving Jake a wink. She pushed him to one end of the couch and lay back on her end.
“Wank that cock for me while you watch me” Karen told Jake, who complied immediately, starting to jerk his cock as he looked at Karen.
Karen spread her legs as far as she could, one thrown over the back of the couch, the other stretched out along the floor.
This opened Karen’s pussy, her wet hole exposed like the centre of a flower after blooming.
Karen traced her bare nipples with one hand, and with the other she started to rub her exposed opening.
First one finger, up and down her pussy lips, then two followed by a third.
She curled her fingers toward her entrance and pushed them inside. Even as open as she was, it was still a tight fit but Karen was determined to accomplish what she was setting out to do.
She thrust the three fingers in and out, her pussy getting wetter and self lubricating. After a few pumps of three fingers, with her pussy visibly stretching to take them all in, she removed them and added a fourth and repeated the same cycle.
Jake watched, enraptured as the Marvel star pushed four fingers in and out of herself, stretching her pussy to its limits, the splashing noises from her increasingly wet pussy making him harder than before.
He continued to jerk his cock, managing to edge himself somewhat, as he too didn’t want to come just yet.
His composure nearly gave out, however, as he gazed upon Karen Gillan with legs spread, adding her thumb into the mix. She squeezed all five fingers together as tight as possible, and proved her entrance. Gripping her wrist with her other hand, she pushed her fist forward inside herself, barely getting to the knuckles on the first push.
She pulled her fist out and wiped her pussy juices around her fist and along the back of her hand too.
She went for a second push, and kept going as she reached the knuckles. She took a deep breath, paused briefly to allow herself a little time to relax and adjust, then pushed her fist in, her knuckles pushing into her pussy, so her entire hand was now inside her.
“Ohhhh gooood, so full” she moaned, her eyes rolling back in ecstasy.
Jake watched as Karen started to move her fist in up to the wrist then out to the knuckles.
He rose from his seated position, and moved to Karen’s head, still stroking his cock.
He took his head in her hands, gave her a kiss, then moved his cock to her mouth. She started to suck his cock again, slobbering over his penis with a lusty vigour.
“You look so beautiful. But I want to fill you up more!” Said Jake, who looked down at Karen’s pussy being so exquisitely stretched by her fist pumping in and out.
“Get that cock nice and wet” he said to Karen, who obeyed, letting the cock fall from her mouth and spitting on it, then using her mouth and tongue to wipe the spit over the entire length of Jake’s penis.
Jake then pulled away from Karen, and moved over to the door to the balcony and opened it.
He came back over to Karen and picked her up and took her onto the balcony. Fist still inside her, Jake placed Karen over the back of a chair near the balcony railing. Karen looked out over New York, her moans being drowned by the sounds of the street below.
Jake took a step back and admired the sight in front of him. Not of the city, but the beautiful redhead’s firm ass, her little pink hole winking as she moved her fist in and out of her pussy.
He knelt down behind Karen on the chair, and stuck out his tongue, moving slowly toward her little puckered rosebud.
The first lick Jake gave to Karen’s tight butthole, combined with the sensations she felt in her pussy, caused Karen to moan long and loudly.
“Shiiiiiiit, fuck yes. Tongue my asshole while I fist my cunt.” Moaned Karen. “You gonna bugger my arse while I’ve got my hand in my fucking minge? I’ve not had more than a wee finger up there before but don’t be soft, make me feel it!” she growled, looking back at Jake with a look of highland fire in her eyes.
As commanded, Jake stood and took a firm hold of his hard cock. He used his other hand to spread Karen’s ass cheeks as best he could, then pressed the bulbous head of his thick cock against Karen’s asshole.
Karen gasped and whimpered as her virgin asshole was penetrated by a large cock for the first time.
“Ah god, it hurts, but don’t stop! Please fuck my ass! God, I’ve never felt so full!” Cried Karen, tears forming in her eyes from the initial pain of the anal penetration and the mind numbing pleasure she was feeling as she adjusted to the feeling of both Jake’s cock in her ass and her fist filling her pussy.
She started moving her fist in and out, moaning as she was able to feel Jake’s cock thrusting in and out of her ass hole as she did so.
She knew her orgasm was close, so she started to move her hand in and out of her pussy with increasing speed.
This, in turn, caused Karen’s tight asshole to constrict more and more on Jake’s cock, increasing his own pleasure tenfold. He continued pumping in and out of the Scottish movie star’s ass as best he could, but the pressure got too much and he had to pull out so it was just the first couple inches he had inside of Karen.
Initially lost in the pleasure he was feeling, Jake soon was alerted by Karen that her orgasm had arrived.
“FUUUUUCK YESSSS, I’M CUMMING! HEAR THAT NEW YORK, I’M FUCKING CUMMING ON A BALCONY” screamed Karen, as she pulled her fist from her pussy and a flood of her juices gushed over the balcony floor.
She almost collapsed from the force of her orgasm, but was held up by Jake’s cock still in her ass, but she knew he was about to blow.
She reached back with her hand, and pulled him out of her. She got off the chair and sank to her knees in front of Jake, taking him in her mouth as far as she could. What remained she started to masturbate, stroking up and down the shaft of Jake’s cock while sucking the head of his cock.
“Gonna cum” panted Jake, his breathing ragged as he watched the Jumanji actress go ass to mouth on his cock.
Karen took his penis from her mouth, and aiming at her face, she jerked Jake’s cock.
“Fucking cum, shoot that big fucking load over my pretty face. How about on my tits? Wanna see my cute little titties coated in your spunk?”
Jake gave in to the dirty talk, blowing his load onto Karen. Some she aimed onto her tits, some she aimed onto her face.
As she was blasted with cum, Karen smiled and laughed. She’d set out this evening with a plan to experience some firsts and her expectations had been exceeded.
Jake’s orgasm came to an end, and he helped Karen to her feet.
“Thank you, Jake.” she said, walking inside the hotel room. Jake followed and shut the door, locking it behind him.
“My pleasure.” said Jake, chuckling. He slumped into a nearby chair.
Karen used her fingers to wipe most of the cum off her face and chest and drip it into her mouth.
Once she was finished, she went to her purse and took out a notepad, opened it to a page and started running down a checklist, ticking off the items as she named them.
“Sex in public, check. Sex in a bathroom, sort of check, fingering counts. Sex in a car, check. Foot-jobs, fisting, anal, all check. Good progress on my list tonight I reckon” said Karen, sitting down on the couch, an evident wet patch visible on one of the couch cushions.
“List?” Queried Jake.
“Aye, my list of firsts. Growing up in Scotland, I was kinda sheltered, not much in the way of adventurous sex there. When I got Who, I started to become more open to sexual exploration but I’ve always been too nervous to ask any of my boyfriends to try them. I’m sure they’d love to do any of them with me, but it’s just a mental thing for me, ya know? So when Emma gave me your number, I figured now was my chance.” Karen explained.
Jake nodded. He kind of understood, he had been kind of the same when he moved to New York. He’d fallen into this job accidentally, and slowly his sexual exploration had grown.
“So anything else on that list I could maybe help with?” Asked Jake, slyly. He got up and walked over to Karen, and yanked the notebook from her. “Oh, this one I can do, let me make some calls” he said, chuckling as he pointed to an item on the list.
Karen pulled the notebook back out of Jake’s hands. “I’m sure you could, laddy, but no more tonight, I’m spent.” She walked over to what Jake assumed was the bedroom door. “I’m gonna take a shower, you okay to see yourself out? Money’s in the envelope!” She said, pointing to a table near the hotel room door. She entered the bedroom.
“Uh, yeh, sure. It was a good night, thank you!” He shouted to Karen as he started to dress, hearing the shower start running.
“It was great, thank you so much!” Yelled Karen back. “Oh, wait, hang on!” She shouted.
Jake, having now dressed, heard Karen searching in the other room. She emerged, still naked, holding a Polaroid camera and a developing photograph.
“Emma mentioned she left you one of these, I figured you might want to bring one of these with you for…ya know…other clients. Like a memory that the cloud won’t get and all that” explained Karen, handing both the camera and picture to Jake.
She kissed him on the cheek, then turned and walked back to the bedroom.
Jake looked at the gifts Karen had given him, smiled and left the hotel room.
After an elevator ride down to the lobby, Jake walked out into the cold New York night.
He hailed a cab and went home and went to sleep.
= = =
The next morning, he awoke to a dozen new messages on his phone.
As he read them, he noticed one question kept being asked.
“Will you be in LA?”
Jake smiled and laughed to himself.
“Guess I’m going to California…”
===To Be Continued===
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Thank you for posting your work, cheers! :Y:
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Chapter 3: An Evening with Mary and Anna
Jake Bryce grabbed his bag, a large carry-all, from the carousel and made his way toward the exit of LAX Airport.
The night before, he’d received a number of messages from possible clients, almost all of them asking if he would be in LA. He had decided there and then to make a trip, packed a bag, booked an open flight ticket and headed to the airport.
He’d spent most of his flight using the plane’s wi-fi and replying to the multitude of messages he had received on his work phone, sending a confirmation to each of the many people who had messaged him that he would indeed be in LA for an indefinite amount of time.
As he approached the exit to the airport, he saw a man, standing by a town car, holding a sign that simply said “Jake Bryce from NY”.
He approached the man, and confirmed his name, showing his ID.
“Welcome to LA!” said the taxi driver, as he took Jake’s bag and put it in the trunk. “You must be important, someone called about an hour ago, said you’d be landing soon and arranging a pickup, they said it was urgent.”
Jake got in the car, the driver got back behind the wheel, and the cab moved off, leaving the airport and heading to the freeway.
As the car drove along the freeway, Jake looked out of the window at the iconic skyline of Los Angeles.
“Just like in the movies, eh? Your first time in LA?" said the driver.
“Yeh,” replied Jake, “I always wanted to visit though. Weather is a lot better than New York, that’s for sure.”
“Tell me about it, I moved here from Brooklyn 10 years ago, and I’m still not used to it. So, are you here for business?” Enquired the car driver.
“I guess yeh, I’m here on business” replied Jake, declining to elaborate further “So, do you know who it was that requested my pickup?” He asked, trying to glean some information about his next client.
“No sir, we just got a call, asking for a pickup and were given your name and flight details. Couple of us in the office thought it might be a prank. Like how long can we keep someone waiting in an airport holding a sign, ya know?” Replied the driver “So, this business, is it a secret?”
“Yeh, I can’t say much more, sorry. Less you know the better.” Said Jake, not wanting to come off as cryptic but not wanting to potentially involve an innocent in something not entirely legal.
“Say no more, sir” chuckled the driver. “Name’s Johnny, by the way. Figured we have a bit of a drive left, if we’re gonna talk you should at least know my name since I know yours.”
“Nice to meet you, Johnny. If it’s okay with you though, I’m gonna shut my eyes for a bit, it’s been a long day.” said Jake.
“Go right ahead, sir. I’ll wake you when we arrive, if you’re still out.” Said Johnny.
“Good man.” Said Jake, as he shut his eyes and drifted off.
Some time later, Jake was awoken by being tapped on his shoulder.
“We’ve arrived, sir.” Said Johnny.
Jake stretched and got out of the car. Johnny had already taken his bag out of the trunk and put it on the sidewalk nearby. He looked around. Every house was walled and gated. He checked his phone, to get the address details.
“Johnny, you know where I’m meant to be going?” He asked. “This has kinda been sprung on me.”
Johnny replied as he was getting back in the car. He pointed to the nearest gate. “That’s the one. 1097.”
Johnny got in the driver’s seat, shut the door, then turned to talk to Jake through the window.
“Good luck with your business, Sir,” he said. “It was nice to meet you.”
“Likewise, Johnny.” Said Jake. “What’s the cost?”
“Already taken care of sir, paid in advance” replied Johnny.
Jake extended his hand. Johnny took it and the pair shook hands, Jake slipping Johnny a decent tip as they did so.
“Thank you very much sir. Goodbye and good luck with your business. If you need another ride, call the company and ask for me” said Johnny, handing Jake a card.
“Shall do, and thanks. Goodbye Johnny.” said Jake.
The town car started and drove off. Jake lifted his bag and slung it over his shoulder.
He approached the gate, and saw there was an intercom. He pressed the button and waited.
He heard a female voice. “Yes?” It asked.
Jake vaguely recognised the voice. “Um, it’s Jake, I’m here for an appointment?”
“Come in” the voice said through the intercom, there was a buzz and the gate opened. Jake walked through, and up the driveway.
He reached the front door of the house, approached the front door and knocked.
He was waiting about thirty seconds when the door started to open, and Jake was greeted by what he first thought was the maid of the house from the outfit, but on second glance he recognised this person to be Anna Kendrick. She was dressed in a maid outfit that even the most ardent slutty Halloweener would describe as “too revealing”. The beautiful brunette’s larger than expected breasts were barely covered by the top, her lack of bra very evident and the skirt just barely came a quarter of the way down her thighs. Her brown hair was done up in high pigtails.
“Welcome sir, I’m Anna. My lady will be with us shortly. Can I get you anything? Would you like a drink? Something to eat? Maybe a blowjob?” Anna asked, cheerfully.
Jake was taken aback by how forward Anna was. “I’m sorry?” He asked her.
“My lady asked that I make sure you are taken care of until she arrives. You are here to fuck her, of course, I can get you ready for that if you would like?” Replied Anna.
The brazen attitude of the pretty young actress shouldn’t have fazed him. He’d heard worse in his line of work, but there was still something shocking about it.
“Uh, I’ll have a drink, if that’s okay? Scotch on the rocks?” said Jake.
“Okay” responded Anna.
She took his hand, dragged him inside the house and led him to a nearby seating area. His bag was left on the porch as he slammed the door shut behind him. She sat him down on a couch, from which he could see across the house to the kitchen, which Anna then started to walk to.
As she walked away, Jake could see that she wasn’t wearing any underwear, and he could just about see something shiny nestled between Anna’s firm little ass cheeks. His suspicions were confirmed when she had to stand on tiptoes to reach some drinking glasses and her cheeks parted slightly, revealing the jewelled buttplug she had inserted.
Anna poured Jake’s drink and walked back over to him, handing him the glass. She knelt down in front of Jake, her hand moving to his crotch
“My lady will be with us soon, are you sure I can’t do anything else for you? I’m yours to do as you desire, Sir.” said Anna, her hand moving up to the evident bulge in Jake’s pants, rubbing his slowly hardening penis.
Without waiting for Jake’s response, she unzips his pants and pulls them down to Jake’s ankles along with his boxers. She takes a firm grip on his semi-hard cock and licks the underside of his shaft, then takes the head in her mouth.
The stunning brunette starts to suck hard on Jake’s now fully erect member, taking more and more into her mouth with each downward movement of her head, maintaining eye contact with Jake the entire time.
Once she reaches the bottom, her nose pressing on Jake’s pelvis, she takes his hands and moves them to her hair. Jake grips one of Anna’s pigtails in each hand, and pulls her head up and down on his cock.
With each downward pull of Anna’s head, Jake felt the warm, wet constriction of his cock in the gorgeous actress’s throat.
Jake kept up this action at a slow steady pace for a few minutes, until Anna pulled herself off his cock. She looked up at Jake with what looked to him like concern.
“Is Sir okay? Am I not doing a good job?” Asked Anna, rising and moving onto the couch.
“What? No, that…that was incredible, you’re an expert.” Replied Jake.
“Then why are you being so gentle? My lady wants me to prepare you, Sir. She says I’m to allow you to use my throat, Sir. Would it be better if I did this?” Asked Anna, lying back on the couch with her head over the side. “Now use my mouth as a fuckhole for your cock, sir.” She opened her mouth wide and waited.
Jake figured to himself that if she was okay with it and he had free reign, may as well go with it. He moved to where Anna’s head was, and pushed his entire length into her mouth, watching in awe as she took the entire thing in one. Her throat bulged as his member pushed its way in, and Jake’s scrotum rested on the face of the Pitch Perfect actress.
He started to thrust faster and faster, each time bottoming out in Anna’s throat. He could feel her gag reflex adjusting with each thrust, but kept picking up his pace. His hands moved to grip the firm breasts of the Oscar nominee, squeezing them and roughly pinching the nipples, Anna audibly squealing on his cock as he did so.
The groans of pleasure coming from Jake, the sound of his balls slapping against Anna’s face and the guttural sounds coming from Anna as her throat was penetrated again and again drowned out the noise of the front door opening. Jake and Anna had an audience now.
Unknowingly being watched, Jake continued to fuck the pretty face and throat of Anna Kendrick, her face now coated in saliva and tears. “Fuck, feels so good in that fucking throat. Gonna fucking cum right down that slut throat, is that what you want?”
Anna couldn’t get the words out, but what he heard sounded like no. She opened her eyes, and became aware that they were being watched. She widened her eyes as if to ask for permission, and their audience simply nodded in affirmation to Anna.
Anna did what she could to move her tongue about in her mouth, trying to coax Jake’s orgasm from him.
“God fucking damnit, you’re unbelievable. Gonna cum, keep doing that. Fuuuck” groaned Jake, who soon lost his restraint. He started to cum, his load firing out right into Anna’s throat.
Anna tried to swallow what she could, but found herself overwhelmed. Once Jake had finished, he pulled his cock from her mouth, and what she hadn’t swallowed came out of her mouth and down her face, some getting on the floor beside the couch.
Jake, currently spent, moved and sat in a nearby chair. He took a minute to collect himself, and then became aware of the spectator standing by the front door, who started to walk over to Anna, still lying on the couch with her head over the side.
“Look at you, you little cumslut.” Said Mary Elizabeth Winstead, in a commanding tone of voice. She approached Anna, and slapped her in the face. “Clean up the mess you’ve made” she ordered Anna, pointing to a small puddle of Jake’s cum on the floor.
Anna quickly got off the couch and on all fours crawled to the cum, licking it directly off the floor.
“Now clean yourself, whore” demanded Mary.
Anna used her fingers to move the mixture of spit and tears and cum off her face and into her mouth, swallowing it all.
“All clean!” Said Anna, cheerfully with a smile on her face. “My lady, did I do good?”
“No,” said Mary, sternly. The taller woman approached Anna. Mary knelt down so she was face to face with her Scott Pilgrim co-star. Her demeanour softened and she smiled “You did great.”
Mary gave Anna a deep French kiss, tasting Jake's cum on Anna's tongue.
The pair broke off their kiss, and Mary turned to Jake.
“Are you gonna be good to go again soon, dude?” Mary asked.
“5 minutes” said Jake, catching his breath. He’d been practising techniques to last longer and recover quicker, figuring his new career path may require him to perform multiple times an evening.
“Good,” said Mary, unbuckling her belt and undoing the tight jeans that clung to her delicious round ass. “Gives me enough time to enjoy this little whore’s tongue”. She grabbed hold of one of Anna’s pigtails, dragged her over to the couch and sat down, pulling Anna’s head toward her crotch.
Anna didn’t need any instruction and she moved to take Mary’s panties off, grabbing them in her teeth and pulling them down the Die Hard actress’s long legs.
Jake looked on in surprise, as it was revealed to him that Mary was unshaven, a wild bush completely covering her pussy.
Mary saw Jake’s look of surprise. “Like what you see, dude? Probably been a while since you saw someone au natural like me, eh? She likes it” said Mary, pointing a finger at Anna. “Isn’t that right, slut?”
Anna replied. “Yes, my lady, I love how your bush tickles my face while I lick at your delicious pussy.” Anna punctuated her words by moving in to start licking away at Mary’s hairy mound.
As Anna licked, Mary removed her leather jacket and pulled the tank top she was wearing over her head.
Her round breasts bounced free, as Mary hadn’t been wearing a bra. Mary pawed at her breasts, squeezing and pinching them as Anna ate her pussy with passion.
“That’s right, bitch, eat that hairy cunt. You lick me so good, just how a dirty skank should. Show this fucker how a real slut acts!!” Moaned Mary, who looked over at Jake. She saw he was starting to get hard again. “Yeh, he fucking likes seeing you eat my fucking cunt. Show him how you make me cum!” She commanded Anna.
“Of course, my lady” said Anna, her voice muffled as she dared not lift her head up from Mary’s pussy, her addiction to Mary’s juices leading her to push her tongue as far into the hairy wet hole as she could manage. She’d been addicted to this since they first fooled around on the set of Scott Pilgrim, which is where this side of Anna first emerged. Mary made her realise her real self, and while she loved being an actress, she hated that when she was on a movie set or at a premiere she had to act in a way against her true nature.
She’d never be able to fully repay Mary for awakening her, but she did her best by becoming a highly adept pussy licker. She pulled her tongue out of Mary, and set about flicking it at great speed against Mary’s swollen clit, poking out from the hair covering Mary’s pussy.
“Gooood, fucking dammit, how do you get better every time we do this?” Moaned Mary, as Anna’s tongue pushed her to the very brink of an orgasm. “You’re gonna make me fucking cum over that pretty face. Do you want that, bitch? My cum soaking your pretty little face?”
Without stopping her licking, Anna nodded, and clamped her lips around Mary’s clit and started to suck on the little nub, causing Mary to buck her hips wildly, her orgasm taking over her.
“FUUUUCK, YESSSS, FUCKING TAKE MY CUM, YOU FUCKING WHOOOOORE. DRINK MY FUCKING CUM, YOU BITCH!” screamed Mary as she came, squirting her cum onto Anna’s face. She grabbed the smaller girl's pigtails, and pulled her face further into her pussy.
Anna’s mouth missed the first blast of Mary’s orgasm, but she moved so she was able to drink the following squirts. Her mouth filled with Mary’s cum, the flavour intoxicating to Anna as it coated her taste buds.
Seeing the beautiful Death Proof actress writhe as she came was giving Jake a second wind, his penis now at full attention again.
Mary, her orgasm now having subsided, looked at Jake and saw his hard cock pointing upwards. She rose from the couch, and over to where he was sitting in the chair.
“You look about ready again.” Said Mary to Jake, as she straddled his lap. She turned her head to look at Anna, who was still kneeling in front of the couch. “Sit and watch, you bitch, maybe you’ll learn something. But don’t you dare fucking touch yourself, got it?”
“Yes, my lady.” Said Anna, who sat on the couch, her own pussy visibly dripping with the evidence of her arousal.
“That’s a good slut you are, Annie” chuckled Mary as she took Jake’s cock in her hand and lined it up with her waiting pussy.
She placed the tip of the penis at her wet opening, still slick with a mix of her own cum and Anna’s saliva, and then slowly eased herself down inch by inch.
“Oohhh, gooood, yesss. It’s been forever since I’ve had a cock inside me. With that one” she said to Jake nodded to indicate Anna “I’m the one doing the fucking, but when Emma told me about you, I had a sudden urge to try you out. Just some random fucking guy who I know won’t go blabbing to the fucking Enquirer about me and Anna and our little arrangement.”
“Discretion is indeed part of the job.” Replied Jake, who was eagerly watching Mary’s firm breasts bounce up and down as she rode his cock, the brunette’s beautiful face contorting in pleasure as her hairy pussy was penetrated.
Jake glanced over at Anna, who was obeying Mary’s instructions and not touching herself, but was clearly very turned out, the petite actress squirming on the couch as she watched, her thighs rubbing together
“I think she should have a closer look at this, don’t you?” said Jake to Mary, who looked over her shoulder at Anna.
“I think she does indeed, good idea.” Replied Mary.
Jake moved one arm around Mary’s round but toned ass, and the other to support himself as he rose from the chair. His cock still inside the brunette, he carried her over to the couch, and sat himself down.
Mary rocked her hips back and forth as she rode Jake’s cock, his lengthy penis hitting all the right spots inside her.
She looked at Anna, who was watching intently, and used one hand to lift the smaller actress skirt, exposing her smooth, bare pussy to Jake.
“Look at that tight pink cunt. Isn’t it beautiful?” Mary asked Jake. “Do you wanna know a secret? I’m the only one who’s been inside it. Isn’t that right, Annie?”
“That’s right, my lady. Only you have been inside my little honeypot.” Replied Anna, smiling. “From that first time when you took my cherry, I haven’t wanted anyone else to be inside it. It’s only for you, my lady.”
“Good girl!” Said Mary, reaching down to give Anna some much needed stimulation, rubbing her fingers along the damp slit of the Oscar nominee, up to her clit and pressing on the sensitive nub.
“Mmmmm, yes, please touch me, my lady. You know just how to make me feel good!” Moaned Anna, thrusting her hips up to stimulate herself on Mary’s fingers.
“Uh-uh, Annie, none of that!” Mary scolded Anna, pulling her fingers away.
“Nooo, my lady, I’m sorry. Please, touch me. Haven’t I been good today? And you always say that when I’m good, I get to cum! Pleeease! I need it, my lady.” Anna paused, flashing Mary a mischievous grin. “Touch me, mom-“
Mary attempted to cut off Anna as she spoke. “Don’t say it!”, she said, but it was too late.
“-my” Anna finished her final word and smiled.
Mary growled in frustration. She stopped riding Jake’s cock, to his confusion and grabbed Anna by the throat.
“You’ve fucking done it now, you little bitch. Do you really want it? Then go fucking get it, you fucking whore. I’ll fucking teach you to do as you’re fucking told. You get what you fucking want, you fuckhole cunt” Mary screamed at Anna, then slapped her in the face and pushed her off towards the stairs.
Jake watched as Anna skipped off, up the stairs. He looked at Mary. “Uhh, what’s going on?”
Mary sighed and explained, somewhat calmly. “I’m sorry, it’s just…that word does something to me, especially from her. No matter what, without fail, if we’re fooling around and she says that, I have to fuck her. And I don’t mean fooling around, fingers and tongues fuck her, I mean actually properly fuck her. I just have to wreck that tight little cunt before I can do anything else. It’s like a compulsion.” Mary thought for a moment. “Actually, you may be able to help me out here. I see you’re still hard, makes sense, we got stopped mid-round by that slut upstairs. How about you help me teach her a lesson together?” She asked Jake.
Jake figured he knew what Mary was getting at and nodded in agreement. “Alright, deal.”
“Good, just follow my lead, okay?” Mary told Jake, as Anna came down the stairs and skipped back toward them.
Jake watched as Anna handed Mary a strap-on dildo, one with a smaller section Jake assumed went inside Mary to stimulate her while using it.
His assumption was confirmed as he watched Mary slide the harness up her legs, inserted the fairly sizable mini-dildo into herself and finished putting the harness on.
The main dildo part was bigger than Jake’s own penis. Maybe 12-13 inches and it was much thicker too. Like a flesh coloured Pringles can.
Jake spoke up, amazed at what Mary now had between her legs. “Christ, she can take that whole thing in her pussy?”
“Yep. She loves to feel this thing rearrange her fucking insides, isn’t that right, slut? Don’t you love this cock in your slutty little hole?” Replied Mary, a tone of aggression in her voice.
“Yes, my lady, I love feeling you stretch my little pussy open with your wonderful cock.” Replied Anna, who had gotten on her knees to start sucking on Mary’s dildo.
Mary put her hand to Anna’s head to stop her. “What the fuck do you think you’re doing? You’re going to be taught a fucking lesson.”
Mary walked over to the couch and sat down, the huge fake phallus pointing to the ceiling. “Get up here, facing me.”
Anna followed, climbing atop Mary and straddling her lap. She reached and lined the dildo up with her pussy, but Mary grabbed her hand.
“Oh, no no no, Annie. You disobeyed me. I told you not to say that word and you did anyway. I was entertaining our guest, and you had to be selfish and put your own fun above theirs. Some maid you are! No no, I want you to take that plug out of your loose fucking asshole right now.” Anna hesitated for a microsecond “Come on, chop chop.” She looked at Jake briefly. “Mind sitting out for a little bit?”
Jake shook his head. He figured he was gonna enjoy this show.
He looked on as Anna pulled the plug out, then showed it to Mary as if seeking approval.
“Good slut. Now, line that little skank butthole up with my cock, there’s a good bitch. Put that plug in your mouth too, I don’t want to hear a peep out of you until I say so, got it? You don’t cum until I tell you to, okay!” Ordered Mary.
Anna only nodded, put the plug in her mouth and positioned the head of the dildo at the entrance to her tight little ass.
Mary thrust her hips upwards, and the dildo began to penetrate Anna’s puckered rosebud.
Anna’s eyes widened as her asshole started to stretch around the girthy fake cock attached to Mary’s waist, but as instructed, not a sound escaped her mouth.
Mary grabbed Anna’s hips and pushed her down as Mary thrust up, more of the dildo entering Anna as she did.
“Yesss, you feel that big fucking cock stretching that little shit-pipe? That’s what little disobedient sluts get, they get their assholes stretched by a huge fucking cock! Oh god, look at you, taking this huge fucking cock up your tight little ass like a fucking pro. I’ve ruined that pretty butthole so much but this is gonna be my fucking masterpiece, you little cunt!” Growled Mary.
Jake, sitting back in the chair, watched as the Pitch Perfect actress’s back door was stretched obscenely by Mary’s toy. He looked on as more and more of the toy was inserted into Anna until, to his amazement, Anna’s ass cheeks rested on Mary’s thighs.
Mary slammed both her hands against Anna’s ass cheeks, causing them to immediately turn a deep pink colour, pulled Anna’s face to hers and kissed her. She looked at Anna and saw her eyes glistening with tears. Not tears of pain however, but pleasure.
Choosing to break character for a minute, she whispered to Anna “Baby, you’re doing so amazing. Happy Anniversary! Are you ready for the rest of your present?”
Anna nodded to Mary.
Mary started to increase how much of the huge dildo she was thrusting in and out of Anna, until she was eventually pulling it all the way out except for the head and pushing it all the way back in.
She then increased the pace of her thrusts in Anna’s ass, fully removing then quickly reinserting all 13 inches repeatedly.
Mary continued at this for minutes, then she called over to Jake. “Dude, are you good to go?”
“Sure.” Said Jake as he rose and walked over to the pair.
“Good, then slide that cock of yours in beside mine in this slut’s shit pipe. This little whore should learn her lesson about obeying me after a good double anal pounding, right?” Mary asked.
“Uhh, yeh, I guess.” Replied Jake.
“Good, now buttfuck this little trashbag with me!” Mary ordered Jake, who felt obliged to comply.
Mary pulled the dildo approximately halfway out of Anna, then said to Anna “Be a good slut and spread those pretty little asscheeks for us, Annie. Open that hole so we can get both these hard cocks inside that ass.”
Anna did as instructed, pulling her buttcheeks apart and creating enough of a space in her asshole for Jake to put his cock in. He was still somewhat slick with Mary’s juices, so he was able to slide in somewhat easily.
“Push forward on 3, okay?” Mary said to Jake.
Jake nodded in agreement.
“1,2,3” counted Mary.
Her and Jake both thrust forward as much as possible, Jake very nearly getting all 8 inches into Anna, but stopped by Mary’s dildo from completely entering Anna’s asshole.
Mary and Jake worked together, silently communicating through looks alone over Anna’s shoulder to settle into a rhythm with each other, one thrusting into Anna while the other pulled out.
The two alternated their thrusting into Anna for some time, until Anna couldn’t take it any longer, her own pleasure having been brought to the brink time and time again, she felt like she had five or six orgasms built on top of one another ready to blow.
She looked down at Mary, eyes pleading for permission to cum.
Mary looked up at Anna, sweat on her brow, make-up smudged and streaking down her face. She reached up and took the butt plug from Anna’s mouth.
“Do you wanna cum, Annie? You want to cum from having your little shit hole stretched by two big cocks? Like a little fucking anal whore, you fucking love having your ass gaped like this, don’t you? Go on, beg me to let you cum while we pound that tight little ass of yours. You have permission to speak, but you have to convince me to let you cum.” said Mary, sternly.
“Pleeeeease, my lady, please let me cum. I need it, I need to cum so badly from these cocks up my ass. It feels so gooood, my lady. Hurts. So. Fucking. Good! Pound my hole, wreck that slut ass, you fucking own it, it’s yours to ruin. Pleeeeeease, let me fucking cum, you goddess. Please my beautiful lady, can I cum?” Begged Anna, her voice breaking as she spoke.
Mary looked at Anna. She looked at her beautiful face, clearly craving a release. She thought about denying her pretty lover, but decided against it. She pulled Anna close and in her ear said one word. “Cum.”
Permission given, Anna stopped holding back her orgasm.
“FUUUUUUCK YESSSS. I’M FUCKING CUMMING. CUMMING FROM TWO COCKS IN MY ASS. FEELS SOOO GOOOOD! FUCKING POUND THAT LITTLE ASS WHILE I CUM! BREAK MY FUCKING HOLE!”
Her orgasm squirted out onto Mary, her stomach and breasts being blasted by Anna’s cum. The petite actress thrashed wildly as she came, Mary and Jake both trying to keep their respective cocks inside Anna, but her wild body movements removed both from her and she collapsed on her side onto the couch.
Mary and Jake watched as Anna shook on the couch, her orgasm still running through her as she moved onto her back.
Mary reached over to Jake and took his cock in her hand.
“Are you about to blow?” She asked him.
“Very close” Jake responded.
Mary started to move her hand up and down Jake’s cock, masturbating him.
“Then cum on this little slut. See those tits, won’t they look even more perfect covered in your spunk? How about that beautiful face? You blew your load inside her mouth earlier, wanna do it again? I’ll hold the little bitch’s mouth open while she’s out so you can do it, would you like that?” Mary asked Jake as she rubbed his cock.
“Up to you, just aim where you want.” Said Jake, very close to cumming.
“Why thank you. I think it has to be that impressive rack of hers. They’re bigger than you’d expect, right?” Said Mary, as she pointed Jake’s cock as the space between Anna’s breasts.
She jerked Jake’s cock faster and faster until he came, jets of white fluid shooting from the head of his cock and landing on Anna’s chest. Mary then aimed his cock at Anna’s face, and a few more shots hit her in the forehead and dripped down her face.
Jake’s orgasm soon finished, he stumbled back into the chair again, catching his breath.
He watched as Mary stood and removed the strap on from her waist, removing the end of the dildo from inside her, her own juices dripping out of her pussy as she did so.
He saw Mary lie down, next to Anna on the couch, and put her arm around Anna’s waist.
“Is she okay?” Jake asked, as he stood and started to gather his clothes.
“Yeh, she’s fine. It just usually takes it out of her, doing that. Give her 5 minutes and she’ll come around.” Mary said to Jake, as she looked at Anna.
“Thank you for tonight,” she said to Jake. “I know she loved it.”
“You’re welcome. I hope she’s okay.” Said Jake.
“She will be, she can take a pounding and bounce back, that’s why I love her.” Said Mary, stroking Anna’s head hair tenderly.
A small, tired voice piped up. “I love you too, Mary.”
Jake watched as Mary cradled Anna in her arms. He finished getting redressed, and as he was about to leave, he heard Mary tell Anna “Rest here for a little bit, my darling, I’ll draw you a bath. You did so well, my love.” Mary kissed Anna on the head and rose from the couch. She picked up her jeans from the floor and took an envelope from her pocket, handing it to Jake. “Five hundred, right? To see how happy it made her, worth every penny.”
Jake smiled at Mary, opened the front door and walked out into the cool night.
Picking up his bag from the porch where he’d left it, he called the cab company and walked to the street and waited.
When the cab arrived, Jake threw his bag in the back seat and sat down beside it.
“Johnny, can you just take me to the nearest hotel? I’m exhausted.” said Jake.
“No problem!” said the driver.
The cab drove off.
Soon after, the car pulled up outside at a hotel. Jake grabbed his bag, exited the vehicle and went inside.
He approached the front desk. “Hey there,” he said to the woman manning the desk “do you have a room available?”
The receptionist checked her computer. “Yes, we have a double room available, Room 302. How long will you be staying with us, Sir?”
“Right now, I’m not sure. Maybe two weeks? Might be longer, I’m here on business.” replied Jake.
“I see, Sir. We can bill you when you check out.” The receptionist handed Jake a keycard. “Elevator’s down the hall and to the left.”
“Thank you.” said Jake, taking the keycard and walking to the lift.
When he got to his room, he threw his bag down, took out his phone chargers, plugged them into a wall socket, put his phones to charge then went to the bathroom to shower.
Once finished, he threw on some shorts and checked both phones. More messages had come through on his business phone, letting him know that Emma and Karen had definitely been spreading the word.
He couldn’t answer them all right now but one grabbed his attention. It was in all caps, and simply said “HOTEL AND ROOM NUMBER?”
Figuring it was too late for anything to happen now, he typed in the details, put his phone down and went to sleep.
*****
Jake woke the next morning to a frantic knocking on his door. He looked at the time on his private phone. 6:00AM.
He got out of bed, groggy from being woken up, and opened the door.
A woman barged her way into Jake’s hotel room and sat down on the bed.
“It’s Jake, right? I have a proposal for you!” Said Aubrey Plaza.
===To Be Continued===
-
Chapter 4: Aubrey Plaza’s Proposal
A woman barged her way into Jake’s hotel room and sat down on the bed.
“It’s Jake, right? I have a proposal for you!” Said Aubrey Plaza,
Jake, still half asleep but intrigued, looked at the stunning woman on his bed at such an early hour. She was dressed as if attending a business meeting. She wore a black pencil skirt which came down to mid thigh on her long legs, the top of her black stockings visible as she crossed her legs on the bed. On her upper body, she wore a white shirt under a black blazer, the top 3 buttons undone to slightly show her cleavage. Her long dark hair was done up in a professional looking bun and her captivating eyes were framed by a pair of glasses. She’d done her makeup also, subtle dark eyeliner and her lips a shade of bright red. She carried a laptop bag over her shoulder, which she put down on the bed next to her.
“What kind of proposal?” Jake asked the sultry brunette, sitting in his bed leaning back on her arms.
“Let me help you with your whole bimbo fucking business!” replied Aubrey.
“Help how?” Asked Jake, curiously.
“I heard about you from Mary, she messaged me after you left. Evidently, you made quite the good impression with her and her little plaything last night. She told me what you’ve been doing and I instantly knew what you needed. You need efficiency, you need management. Essentially, your dick needs an agent and I’m here to put myself forward for the role.” Said the raven haired beauty.
“An agent? And what would that entail, exactly?” Asked Jake.
“Give me your phone, the one all these tramps have been messaging and I’ll show you.” Said Aubrey.
Jake went over to the bedside table, and picked up his work phone.
Jake unlocked and handed the phone over to Aubrey.
She took the phone, and took a MacBook from her shoulder bag. She scrolled through the phone, typing information into the laptop as she did so and replying to messages.
Jake watched Aubrey in action, the concentration on her face making her somehow look more beautiful.
Aubrey soon locked the phone again, and looked to Jake.
“And voila!” She said, spinning the laptop toward Jake.
He stepped closer and studied the day calendar Aubrey had set up. She has split his day up into 5 or 6 blocks of about three hours each, the last ending at 11pm that evening.
“Follow this, that should be two and a half, three thousand you’ll have made today.” Said Aubrey.
Jake studied the schedule Aubrey had created.
He looked at the brunette. “So, if I go along with this, what exactly is in it for you? I’m assuming you’re after a cut?”
“Every good agent has their rate, honey. Ten percent for the day is mine.” Replied Aubrey. “I know for privacy's sake, you’re paid in cash, I’m happy to take the same.”
“I’m not agreeing, but I’m willing to call today a trial run and we’ll see how it goes.” Said Jake.
“If that’s what it takes.” Said Aubrey.
Jake looked again at the schedule. In his not fully awakened state, he hadn’t looked at the blocked out sections fully. When he did, he turned to Aubrey with a question
“So, I can’t help noticing there’s a session here that looks to already be in progress.” Jake said, studying the laptop. “Is that for you, I take it?”
Aubrey rose from the bed and started to undo her blazer. “Well, I’ve not come all this way just to offer to be a glorified secretary. I figured I would at least sample what you got to offer. The way Mary described how that cock felt, I have to try you out for myself!” she said, as she continued removing her clothes. Her shirt and skirt had both been discarded, leaving the dark haired Parks and Recreation star in a black lace two piece lingerie set and black stockings. She undid her hair and let the dark tresses fall to her shoulders.
Jake stood up and Aubrey kissed him on the mouth, her tongue probing between his lips until they parted. The two French kissed in the middle of the room, until Jake moved and pushed Aubrey against the nearby wall. His hands on her hips, he held her there as the kiss was broken. Aubrey raised a hand to remove her glasses, but Jake stopped her.
“Leave them on!” He growled at her.
Aubrey complied, leaving the glasses on her face. She moaned as Jake started to kiss her neck and collarbone, long time erogenous zones for her. The way Jake nibbled, kissed and sucked on her skin driving Aubrey crazy.
“Mmmm, bite me! Leave a fucking mark on me, you know you want to!” Groaned Aubrey, followed by a deep moan as Jake did as requested. He bit down on her shoulder, hard enough to leave a mark but not break the skin. Aubrey shuddered with desire, her hand reaching down to rub Jake’s hardening penis through his shorts.
Jake followed this up by kissing down to her petite breasts. He kissed Aubrey’s chest between the two mounds of flesh, and reached behind her to undo her bra.
He unhooked the item and pulled it away from Aubrey’s body with his teeth and dropped it to the floor, then latched himself onto one breast while his hand played with the other. He sucked on Aubrey’s nipple, feeling it get harder in his mouth while his hand kneaded the soft flesh of her other breasts, pinching that nipple between his fingers.
Knowing how she liked being bitten on her shoulder, Jake did the same to each nipple, causing the dark haired beauty to squeal and moan.
“Oooh, fuck yes. That’s what I like! Keep biting me, bite me while I stroke this hard fucking cock!” purred Aubrey, as she reached her hand into Jake’s shorts and gripped his fully hard penis. She started to rub her hand up and down his shaft, quickening her pace as Jake gave her nipples another bite each.
The pair kept this up for a few minutes, before Jake started kissing a path down from Aubrey’s breasts, down her toned stomach. This caused Aubrey to stop jerking his cock, as it moved out of her reach. Jake swirled his tongue in Aubrey’s belly button, causing the Legion star to giggle, before he continued and reached the top of her panties.
He used both his hands to take hold of and pull Aubrey’s panties down her long, smooth stockinged legs, rubbing a leg with one hand each as he moved them both back up to Aubrey’s hips.
Her pussy now exposed, Jake studied it briefly, the hairless mound glistening with the evidence of her arousal. He blew onto Aubrey’s pussy, causing the actress to moan loudly, before he dove in and started to fuck her tight hole with his tongue.
“Fuuuuuck. Fuuck, you’re good at that!” moaned Aubrey. “Lick my cunt, man whore! Tongue my fucking pussy, make me cum on that tongue!”
Jake listened to Aubrey’s aroused demands, and considered keeping her waiting as revenge for waking him up, but as he thrust his tongue in and out of her tight hole, he found her flavour too good to pass up.
Jake kept licking Aubrey’s pussy, before getting a wicked idea. He pulled away from her pussy and with both hands on her hips, he turned Aubrey around against the wall, and pulled her ass cheeks apart, exposing her little ass hole.
He resumed licking at the wet pink hole, and when he thought the time was right, he licked from Aubrey’s clit, and up to her little anal ring.
“Mmm, god yes, rim my fucking asshole. Stick your tongue in my little asshole. Fucking spank my ass while you do it, make my fucking asscheeks pink!” Ordered Aubrey.
Not one to resist an order, Jake withdrew both hands from Aubrey’s cheeks, pulled back with both of them and as hard as he could he struck both cheeks, a red hand mark remaining as he pulled his hands away again and repeated the move.
Jake did this a third time, then ran his hands around Aubrey’s waist and onto her pussy. His fingers ran along the slick wetness of her pussy, then Jake curled two of them inside.
“Mmm, fuck yes, finger my tight, wet cunt while you tongue fuck my ass. Oh god, make me fucking cum on those fingers!” Moaned Aubrey, moving her hips in an attempt to get more of Jake’s tongue and fingers inside her holes.
Jake obliged, and quickened the speed of his fingers pumping in and out of Aubrey Plaza’s wet pussy, and rapidly flicking his tongue against her tight, puckered asshole.
This had the desired effect, and Aubrey’s orgasm soon came. Her upper body still pressed against the wall, Aubrey shook and screamed as she came.
“FUUUUUCK YEESS! FUCKING CUMMING FOR YOU, ALL OVER THOSE FUCKING MAGIC FINGERS! GODDDDDD DAMMIT, YES!” Screamed Aubrey, almost collapsing as the pleasure ran through her entire body, only remaining upright as Jake held her in position.
Jake rose from his position on the floor, pushing his shorts down to expose his cock whilst holding on to Aubrey’s waist. He took hold of his cock and rubbed it against her wet entrance.
“Wait,” Mumbled Aubrey, who turned around, put her arms around Jake’s neck, and used what energy she currently had to jump up, wrapping her smooth stocking clad legs around his waist. “Fuck me against the wall like this!”
Jake put one arm under Aubrey’s ass to support her, while he used his other hand to position his cock at her wet hole. He pushed forward, his cock entering Aubrey Plaza’s pussy for the first time. Aubrey’s pussy was wet enough that Jake was able to push his entire length into her on the first stroke, the feeling causing Aubrey to cum again immediately.
“OHHH GOOOD! YOUR COCK IS SO FUCKING DEEP! POUND THAT PUSSY WITH YOUR HARD FUCKING COCK!” Shouted Aubrey, before silencing herself by biting Jake on his shoulder.
Jake pumped himself in and out of Aubrey against the wall as she came again, the way her wet pussy hugged his cock tightly causing him to feel ecstasy of his own.
“You’re so fucking tight!” Groaned Jake, which roused Aubrey from her post-orgasm stupor. She lifted her head and looked at Jake, eyes filled with desire behind the glasses on her face. Studying his face, she could see he was straining to keep them both upright.
“Take us to the bed.” Said Aubrey.
Jake did as he was told, carrying Aubrey over to the bed, his cock still within her wet pussy.
“Lie down, let me ride this beautiful cock!” Barked Aubrey.
Jake again followed Aubrey’s command, first sitting in the bed then moving them both over so he was lying down.
Aubrey pulled herself off Jake’s cock, and sat down between his feet. She moved her stocking covered feet up to Jake’s cock, and placed one either side of his shaft. She put her feet together around the hard cock, and started to give Jake a footjob, her feet moving up and down his shaft.
Jake moaned as the soft fabric of the stockings touched his sensitive member. He remembered how good the footjob Karen had given him felt, and this was infinitely better.
“Yes, jerk my fucking cock with those pretty feet. This feels amazing, you sexy fucking bitch.”
Aubrey started to pump her feet up and down on Jake’s cock faster and faster, her toes rubbing the bulbous head as they passed it.
The faster Aubrey went, the closer Jake felt his orgasm getting.
“Mmm, keep doing that, I’m gonna ruin those fucking stockings!” Jake groaned, causing Aubrey to pause.
“Nuh uh, Jakey, you’re not gonna cum just yet! There’s more I wanna do with this cock first!” said Aubrey, shifting herself and crawling up Jake’s body, until the swollen tip of his cock was rubbing at her wet pink hole. Aubrey reached down, held Jake’s cock steady at the entrance to her pussy, and dropped herself down onto it.
In this new position, Aubrey started grinding her hips back and forth on Jake’s cock.
“God, that feels amazing. Ride my cock, Aubrey. You’re fucking gorgeous!” Moaned Jake.
Aubrey smirked at Jake, and started grinding faster and faster.
She took his hands that he had placed on her hips, and bought them up to her neck.
“Choke me! I don’t want any of that “You’re gorgeous” bullshit, fucking do it!” Said Aubrey, her voice dripping with passion.
Jake hesitated briefly, but then put his hands around Aubrey’s throat and started to squeeze.
This action caused Aubrey to go even faster riding Jake’s cock. Instead of grinding back and forth, she was squatting over him and bouncing herself up and down Jake’s shaft. Her hands were running over Jake’s chest, her fingernails clawing at his skin as she did so.
The feeling of Jake’s cock going deep into her pussy, coupled with the euphoric feeling she felt from her breathing being restricted was bringing a third orgasm closer for Aubrey.
“MMM, YES! GONNA CUM AGAIN!” Rasped Aubrey, her throat still being squeezed by Jake.
Aubrey bounced up and down, faster and faster. In her frantic movements, Jake’s cock was fully removed from her pussy.
Taking one hand off Aubrey’s throat, Jake went to position his cock back at the entrance to the former April Ludgate’s pussy.
“Noo, stick it in my ass!” Growled Aubrey, who rubbed her fingers against her wet pussy then moved them behind herself and rubbed her juices against her asshole.
Aubrey still on top of him, Jake positioned the head of his cock, shining with Aubrey’s juices, at her tight sphincter and pushed his cock forward, opening her little asshole for him.
As his cock pushed into Aubrey’s asshole, inch by inch being swallowed by the tight hole, Aubrey rubbed her pussy, her swollen clit protruding from its hood at the top of her wet lips.
She pushed down on the little pink nub as her asshole was stretched by Jake’s long cock, giving herself a third orgasm, her cum shooting out over Jake’s chest.
Though Aubrey’s asshole got tighter as she came, Jake persevered with inserting his cock into it, the restrictions feeling wonderful for him.
Jake soon bottomed out, Aubrey’s firm asscheeks resting against his thighs, the entire length of his cock deep within the beautiful actress’s ass.
Her orgasm subsiding, Aubrey started to lift herself up and down on Jake’s cock.
“Oh god, yes, I love that big cock in my tight little ass. Fucking fill my ass with that big dick!” Groaned Aubrey, who was slapping her own breasts as she rode Jake’s cock.
“Feel so good in that ass!” Moaned Jake. He’d removed his hands from Aubrey’s neck and was running them along the slim stocking clad legs of the dark haired beauty.
The two settled into a steady rhythm, the only sounds in the room being their moans of passion and the sound of Aubrey’s asscheeks slapping on Jake’s thighs.
Aubrey soon spoke up. She leant down, her face close to Jake’s ear. She whispered to him as she bounced on his cock.
“How do you like that ass? Nice and fucking tight for you? Much better to fuck than that loose fucking hole of that Kendrick slut, isn’t it? What about Hermione’s little fucking shitter, is mine better than hers? Or that Scottish bitch, her butt isn’t as good as mine, is it? That's right, I’ve done my research on you, Jake, good and proper! Mary told me about you and I rang around. I’ve heard all about what you’ve been doing. What did it feel like to have your cock deep in Emma’s throat? When you finger fucked Karen in that bathroom, did you wish it was your cock? I bet you did, this big fucking dick just needs to be in any famous sluts holes, doesn’t it? That’s where it belongs! That’s what I can help you with! I know a hell of a lot more desperate Hollywood skanks who’d pay for a couple hours with this cock, pounding their tight fucking holes. I even know some who’ve never had a proper cock inside them, would you like that? Being the first to stick their dick in some cherry cunt? Stretching those fresh pussies out, giving those tight cunts their first proper fucking!” Purred Aubrey.
“God, yes, that sounds incredible!” Moaned Jake, feeling own orgasm approaching as Aubrey spoke. His thrusting in Aubrey’s ass increased in pace, driving the beauty on top of him crazy. Thinking of what Aubrey requested from him earlier, he put his mouth to her neck,and bit down.
“Gooodd, yes. Bite me, fucking mark me! Mmm, bite my neck while you pound my ass. Ruin my asshole! Make me feel it! Punish me for bursting into your room at the crack of dawn! Slap me, I know you want to! Slap my face, or my tits, even my cunt! Yes, slap my cunt! It’s so fucking sensitive!” Screamed Aubrey.
Jake, lost in his own ecstasy, did as requested. He slapped Aubrey across the face with as much strength as he could spare, then each of his breasts before slapping downwards on Aubrey’s pussy, the main point of impact being her throbbing clitoris.
This sparked another orgasm in Aubrey, her most intense yet.
“GOD FUCKING YES DAMMIT! GOOOOD, FUCKING CUMMING! YESSSS, AAAARGH!” She screamed, her moans quickly devolving into guttural noises. The intensity of her orgasm caused her whole body to shake and gyrate wildly. She jumped off Jake’s cock, his whole length withdrawing for her in one go.
Though her body was pulsing with the aftershocks of her orgasm, Aubrey maintained some sense of urgency with herself, and moved so she could take Jake’s cock in her mouth.
Jake watched as Aubrey opened her mouth wide, and in one movement took his cock all the way.
Learning from earlier what Aubrey liked, Jake used one hand to keep Aubrey’s head down on his cock, and his other hand pinched her nose, closing her nostrils.
Jake grabbed a handful of Aubrey’s hair, and holding her on his cock, he moved them both so he was now standing and Aubrey was on her knees.
Jake kept his cock in Aubrey’s throat whilst pinching her nose shut until she tapped on his thighs, then he pulled his cock from her mouth.
Aubrey deeply gasped for air, a mouthful of saliva running from her mouth and onto her breasts. She looked up at Jake with lust.
“Again. Stick this big cock down my throat again!” Demanded Aubrey, grabbing hold of Jake’s cock and rubbing her hand up and down the shaft.
Aubrey opened her mouth again, and Jake pushed his cock inside, hearing Aubrey gag as he hit the back of her throat. Jake again shut Aubrey’s only airway, pinching her nostrils closed.
Jake looked down as the stunning dark haired actress, locking eyes with her as he began to thrust his cock in and out of her throat, Aubrey not allowing her lips to leave his cock even for a second so no air could get in.
As Jake started to fuck the face of the Parks and Rec actress, Aubrey moved one hand down to her pussy. She rubbed herself as she choked on cock, one of her favourite things to do with a partner
As her throat was penetrated over and over by the thick cock, Aubrey started to finger her pussy.
She inserted two fingers between her wet lips and curled them upwards, rubbing her G-Spot while Jake’s cock went back and forth in her mouth.
Tears filled her eyes as her throat was fucked.
Jake withdrew from her mouth again.
Another mouthful of saliva dripped onto Aubrey’s modestly sized chest as she swallowed oxygen to get her breath back.
She took Jake’s cock in her hand and started to jerk him off.
“You gonna cum, Jake? You wanna cum on this pretty face, huh? What about my tits? Look at them, all shiny with my spit. How about you shoot your load on these perfect little tits and I leave it to dry and go about my day, my chest caked in your dry cum? I have some meetings to go to, it would be so hot to sit with all these executives, my tits covered in hot semen and they wouldn’t know it.” Said Aubrey, looking up at Jake.
“Mmm, fuck, yeh. Gonna cum, all over that beautiful fucking face!” Jake grunted.
Jake fought to hold his orgasm back, but his floodgates soon opened. He took his cock from Aubrey, jerking it as he held her in place by the hair and quite quickly, streams of his cum shot out and landed on Aubrey’s face, covering the glasses on her face. Some hit her on the nose, and the remainder he shot onto her forehead. Jake shot more than he expected, and once he finished, Aubrey’s face was covered. Aubrey continued fingering her pussy as Jake cum, her own orgasm coming as the last few shots of his load hit her face.
“I’M. CUMMING. AGAIN. GOD FUCKING YES, YES, YES!” Panted Aubrey.
Jake pulled back, and watched the brunette beauty cum while on her knees. She fell forward, catching herself with one arm. Some of Jake’s cum dripped from Aubrey’s face onto the floor.
“Fuck, what a load! Jesus Christ!” Chuckled Aubrey, rising to a more upright position and sitting on her knees. Her face covered in a glaze of white, she started scraping the cum from her face off with her fingers and sucking them clean.
“Sorry.” Said Jake, whilst watching Aubrey eat his cum.
“Don’t apologise. I fucking love cum, and yours, may I say, is delicious!” Replied Aubrey, who finished cleaning off her face, removing her glasses to lick the cum off the lenses.
She looked over at the clock beside the bed. It read 7:15.
“You better go shower,” said Aubrey to Jake, “you’ve got a booking at 8! I'll call you a cab, go get ready!”
She rose and pushed Jake to the bathroom.
Jake showered, thoroughly cleaning himself of the evidence of his and Aubrey’s morning fun.
He finished and came out of the bathroom, finding Aubrey sitting up in bed in her shirt and stockings, laptop on her lap.
Jake started to dress. Aubrey occasionally glanced over in his direction, admiring his toned physique.
Jake debated whether to put his suit from the night before back on or wear something more casual, pulling a pair of slacks and a shirt from his bag.
He looked over to Aubrey for her opinion.
“Slacks and shirt. They do dry cleaning here, I’ll take your suit down when I leave.” Said Aubrey, barely looking up from her laptop.
Jake finished getting dressed.
“Very nice” said Aubrey, giving Jake a once over with her eyes.
She swung her legs off the bed, picked up Jake’s phones and handed them to him.
“I’ve messaged you a link to your calendar for today. Just open it and the phone will do the rest. Now get going, your cab will meet you downstairs.” Said Aubrey, as she moved to the hotel room door and basically pushed Jake out of the room.
As he made his way downstairs, Jake opened the message from Aubrey on his phone and clicked the link she had sent. His phone stalled for a few seconds, then he got a number of calendar alerts. He opened the first one, and looked at the address.
As he reached the lobby and walked out the front entrance, he caught sight of his cab in the parking lot. He approached and signalled the driver.
The car drove to him, and Jake got in the backseat. The car drove off from the hotel. Jake sat back and felt his phone vibrate in his pocket. He took it out and answered it.
“Hello?” asked Jake.
“It’s me,” said Aubrey, on the other end of the call. “Just to confirm your schedule, I’ve blocked out three hours total per client today. Not that you’ll need the whole three hours, you could be done in one but I figured allow you some time in between to shower, eat, work out, whatever you wanna do. Got it?”
“Got it!” replied Jake. “So, do you know who my first appointment is with?”
“No, I don’t,” said Aubrey. “All their message said was “husbands away, meet me at yada yada in the backyard”. I thought I might recognise the address, but doesn’t ring a bell. But then again, even if I did know who it was, I’d still not tell ya. Where’s the fun in that for you, knowing what or who you’ll be getting.” said Aubrey, an evident teasing tone audible in her voice.
“Fair enough. Will I see you later?” asked Jake.
“I’ll come back, yeh. I’m confident you’ll take up my offer, we’ll have more to discuss after your trial day. Just let me know when it’s over and you’re back at the hotel and I’ll come by. Maybe we’ll even have a repeat of this morning, would you like that? Would you like another go at fucking my tight little ass? It still feels kind of open right now, but maybe by tonight, it will have closed up, ready to be opened by you again. Do you want that? Wanna feel my tight ass around that cock? Mmm, I do, I wanna feel you stretch me out. I might imagine that and play with myself in this hotel room, thinking about you fucking me in my ass over and over. You thinking of that, Jake? Me, in nothing by my stockings, playing with my tight little cunt, moaning over the thought of your hard cock filling my ass with hot cum?” said Aubrey, her tone on the line now extremely sultry in nature.
Jake gulped. “Yes!” he said, trying not to give away to the driver that he was now almost completely erect.
Aubrey’s voice changed to a more business suited tone.. “Good, now keep that thought in your mind, so you’re ready to go for your first appointment. See ya later, Jake, kisses” and she hung up suddenly.
Luckily, a couple of minutes after she did, the car stopped at its destination.
“That’ll be twenty five dollars, sir.” said the Driver.
Jake took out his wallet, handed the driver a twenty and a ten. “Keep the change!” he said as he turned toward the house his appointment was in.
He pressed the buzzer on the wall by the gate, and was buzzed right in.
Jake walked up to the house, and as he approached the front door, he saw a yellow post-it note stuck to it, with a message saying ‘In the pool, come around through the side gate’ and an arrow pointing to Jake’s right.
Jake followed a path around the house, going through the side gate and into the pool area.
There, he saw two chairs, facing the pool away from the gate. He could see a pair of smooth legs on one sun chair, he walked toward the pool, and coughed to make his presence known.
“Come around, let me look at you!” said an accented voice.
Jake walked around in front of the sun-lounger, and gazed in awe, taken aback by the sight that greeted him.
“Well, you are a handsome chap, aren’t you?” said Emily Blunt, lying naked except for a pair of sunglasses. She sat up and turned toward the house. “Annie, the man has arrived! Get your cute butt out here now!” she shouted.
“I’m coming!” A voice shouted back, and Jake was further taken aback by Anne Hathaway strolling toward him from inside, equally as naked as Emily. When Anne got to the chair that Emily was lying in, she leant down and gave her a big kiss on the lips. When the kiss broke apart, the two women looked at Jake.
“Good! Now that you’re here, we wonder if you can help us settle a bet…” said Anne.
===To Be Continued===
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Just an update regarding this series, I am working on Chapter 5 currently but I’ve started from scratch as I wasn’t happy with how it was going.
I’ve started with a new approach to what Anne and Emily want from Jake which I hope turns out well.
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Not a problem if you need celeb specific intel I've amassed a pretty big bundle in 17 years of writing I'd be happy to share
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What kind of intel have you got?
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I've got all kinds of stuff pulled from searches, interviews, articles, on air bloopers, open mics, red carpet stuff just a question of what you need for a story as to what I have got a stack of index cards nearly 6 feet tall with bits and pieces written on them
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I've got all kinds of stuff pulled from searches, interviews, articles, on air bloopers, open mics, red carpet stuff just a question of what you need for a story as to what I have got a stack of index cards nearly 6 feet tall with bits and pieces written on them
That's not "intel". That's public information that anyone who wants it, can search for online.
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In a few cases yes however I'm working on some Emma Watson intel I know for a fact nobody has access to that I will be throwing in an upcoming project
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In a few cases yes however I'm working on some Emma Watson intel I know for a fact nobody has access to that I will be throwing in an upcoming project
Right. I'm sure you also have this week's Powerball numbers too.
This discussion ends here with a warning. Do not come on here and try to mislead authors with BS like this. If you want to write stories based on fantasies, that's fine. There is a boundary you cross when claiming you have restricted info that no one else has.
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I’m back in a rhythm with Chapter 5, so I hopefully should have it up by this weekend. Who would people like to see in future chapters?
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If I had any request, it would be Katy Perry, Britney Spears, Kate Upton, and maybe Scarlett Johansson.
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If I had any request, it would be Katy Perry, Britney Spears, Kate Upton, and maybe Scarlett Johansson.
Beside Scarlett, those are names I hadn’t considered but I will now!
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If I had a request, it'd be Emily Ratajkowski. I could probably think of more too, but I wouldn't want to overwelm you, I know you're probably really busy.
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I’m back in a rhythm with Chapter 5, so I hopefully should have it up by this weekend. Who would people like to see in future chapters?
Hi. Great stories. If you're taking requests could you do Ariana Richards, Eliza Dushku or Felicia Day?
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I’m back in a rhythm with Chapter 5, so I hopefully should have it up by this weekend. Who would people like to see in future chapters?
Hi. Great stories. If you're taking requests could you do Ariana Richards, Eliza Dushku or Felicia Day?
I don’t know who the first person is, but those other two are solid options.
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If I had a request, it'd be Emily Ratajkowski. I could probably think of more too, but I wouldn't want to overwelm you, I know you're probably really busy.
Yeh, I still work a 9-5 so I’m writing when I can after work each day and on weekends. If you have other suggestions, I’m happy to take them. They might make future chapters of GTTS or I might work on something else.
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I’m back in a rhythm with Chapter 5, so I hopefully should have it up by this weekend. Who would people like to see in future chapters?
Hi. Great stories. If you're taking requests could you do Ariana Richards, Eliza Dushku or Felicia Day?
I don’t know who the first person is, but those other two are solid options.
Ariana Richards was in the first Jurassic Park movie
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A few suggestions. Liz Gillies, Madonna, Sigourney Weaver and Helen Mirren. Helen Mirren really is just so prolific, heard she's been still hot for a woman as old as she is too
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Sorry everyone. I meant to have Chapter 5 done and posted by now, but there’s been some personal stuff come up recently that stopped be from being able to write.
I’m back at it now, and progressing Chapter 5 and have a start for Chapter 6 down on my paper.
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UPDATE
Chapter 5 has been written.
Just need to finish the proofreading and it should be posted this weekend.
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Chapter 5: Anne & Emily Make A Video
“Well, you are a handsome chap, aren’t you?” said Emily Blunt, lying naked except for a pair of sunglasses. She sat up and turned toward the house. “Annie, the man has arrived! Get your cute butt out here now!” she shouted.
“I’m coming!” A voice shouted back, and Jake was further taken aback by Anne Hathaway strolling toward him from inside, equally as naked as Emily. When Anne got to the chair that Emily was lying in, she leant down and gave her a big kiss on the lips. When the kiss broke apart, the two women looked at Jake.
“Good! Now that you’re here, we wonder if you can help us settle a bet…” said Anne.
“A bet?” Asked Jake, as he ogled the two nude beauties in front of him.
“Oh, we’ll get to that, don’t worry! We've got other business to deal with first!” Said Emily, as she reached down to her purse underneath her chair, rummaged inside and pulled out a video camera.
Emily turned on the camera and pointed the lens at herself and Anne, who knelt down beside Emily and put her arm around her as the Brit addressed the camera directly.
“Hey hubbies, we miss you! We’re just enjoying the morning sun by the pool and we’ve got a surprise for you both! Anne, care to do the honours?” Said Emily.
“Absolutely!” Said Anne, who got to her knees on the hard ground and crawled toward Jake with Emily filming her as she did, stopping in front of Jake as Emily narrated.
“Now, Little Miss Oscar Winner here wasn’t completely satisfied with just me keeping her company, she was pouting about not having a flesh and blood cock to suck on so when I got a little tip from a friend of mine, I made some arrangements! Anne, show our husbands our special guest for today?”
“With pleasure, Emily.” Said Anne, as she moved closer to Jake.
The pale beauty looked up at Jake, her big round eyes meeting his own as she took hold of his pants at the waist and pulled them down, taking his boxers with them.
Jake’s semi-erect cock sprung up into Anne’s face, and the one time Catwoman gripped it, moving her hand up and down the shaft.
“Look at the size of that thing, guys. It’s bigger than either of you and he’s not even fully hard yet. Oh Adam, I’m going to enjoy watching your beautiful wife suck on that hard fucking cock. Do you want that Anne? You want to feel that throbbing huge dick deep in your throat? Don’t tease our friend here, Anne, open those sexy dick sucking lips of yours and take that cock in your mouth!” Said Emily as she filmed, gripping Anne’s hair and pushing her toward Jake’s cock.
The Princess Diaries actress parted her lips as she got closer to Jake’s cock and took the head into her mouth.
“Oh fuck!” Jake groaned in pleasure as Anne’s tongue ran along the sensitive area where the head meets the shaft on his cock.
Anne focused solely on the head at first, using a combination of kissing, licking and sucking to bring Jake’s cock to fully erect before she started to move herself down. She went slowly, going inch by inch, pausing as necessary to allow herself to adjust to the thick cock pushing deep into her mouth.
“Bloody hell, Anne, I know you can do better than that! I’ve seen you take bigger dicks all the way down in half the time! We’re gonna find out which of us gives better head and you’re not much competition at the moment!” Said Emily as she continued filming. One hand held the camera on the action and Jake could see her other hand playing with her hardening nipples.
Emily continued to encourage Anne. “Pretend he’s that lighting guy from Prada, the one with that beautiful huge cock. Remember when we took him into Meryl’s office set after wrapping one evening and you got him from six to midnight in no time, taking the entire thing down your throat in one go? Want to prove you’re better than me, sweetie, you gotta do more than this!”
Taking Emily’s words to heart, Anne removed Jake’s cock from her mouth and paused for a moment to collect herself. She took a few deep breaths as she focused herself, then opened her mouth wide and in one movement took the length of his cock inside, suppressing her gag reflex as the swollen member pushed into her throat.
“Attagirl, Anne! Show the camera how much you love a big cock in your throat! How’s it feeling, Jake? Is the slutty Oscar winner doing a good job sucking your fat dick?” Asked Emily with a smile, as she zoomed the camera in on Anne’s face, her eyes watering as she frantically moved her mouth up and down Jake’s cock. “Help her out, Jake. Yeh, that’s it, grab her hair and fuck that beautiful face. Oh god, I’ve lost count of the number of times I’ve held her hair as I’ve rubbed my pussy against that gorgeous face. Mmm, the things she can do with her tongue! Though I probably don’t have to tell you, she’s probably doing some right now, isn’t she? I bet she is. You’re a filthy little slut for cock and pussy, aren’t you, Anne? You’re gonna make Jakey boy here cum in that pretty mouth, aren’t you? Fuck, it’s turning me on so much to see those perfect plump lips wrapped around that thick cock. Doesn’t she look beautiful like this, Jake? That gorgeous fucking face filled with cock, her perfect MILF body exposed for your admiration. Doesn’t her body look absolutely incredible, Jake? I bet you’d like to feel those marvellous tits or even that glorious wet cunt around that cock of yours, huh? But not today. No, today’s just about settling our little contest. Maybe we’ll bring you back another time to fuck us, maybe with our husbands. The three of you and one of us with a strapon absolutely railing every hole of the other.
The combination of Anne’s amazing blowjob skill and Emily’s dirty talk were bringing Jake close to the edge. He knew he was close, the warm, wet tightness of Anne’s mouth feeling heavenly on his cock. He had heard what Emily had said about the two of them wanting to find out who was better at sucking cock, and as he thought about how Emily could possibly match or exceed Anne, whose tongue was running back and forth across the shaft of his cock as he pumped in and out of her mouth.
Jake looked down at Anne and as he gazed into those beautiful big eyes which almost looked to be pleading for him to cum, he felt his restraint crumble. “I’m gonna cum!” panted Jake, as his orgasm neared.
“Do it on her face! Paint that gorgeous face with your cum!” Said Emily, pointing the camera at Anne’s face as Jake withdrew his cock from Anne’s mouth and started to jerk it in front of the brunette.
The one time Catwoman, now free to speak, looked up lustfully at Jake. “Do it! Cum on me! Blast that big, hot load over me! I want it everywhere, my face, my mouth, my tits. Wouldn’t they look so good covered in your cum?” She said huskily as she took a breast in each hand and pushed them up toward Jake’s twitching cock. “Cum on me, Jake. Coat me with your cum. Please, I want it so bad, it’s been ages since I’ve had a hot load dripping down my face, please give it to me!”
As he looked at Anne, Jake was sure he was looking at one of the sexiest sights he’d ever seen. Her long brown hair messy from him grabbing two handfuls, her face shining with sweat, saliva running from her mouth and down her chin, dripping onto her large breasts. As she finished her plea to Jake for his cum, she pouted and the way her bottom lip plumped up finished Jake.
His orgasm came and came strong. Long streams shot from his cock and onto Anne’s beautiful face, landing on her cheeks, nose, forehead and mouth.
“Christ, Anne, he’s fucking glazing you!” Said Emily, who was filming in such a way to catch both Jake’s ejaculation and the loads landing on her friend’s face. “How does it feel?” Emily asked.
“God, it’s so hot. Such a warm load! And tasty too, you got to try it, Em! Share his cum with me!” Said Anne, giggling lightly to herself as her tongue pushed out to try and lick up any cum near to her mouth, then Anne moved to lick the last drops of Jake’s cum from his cock as his orgasm was finishing.
“There’s an offer I’d never say no to!” Said Emily. She looked at Jake. “Hun, would you mind filming until you’re ready to go again for my turn with you?” She asked him. Jake shook his head, and took the camera from Emily, keeping the shot as she had it, Anne’s cum covered face close up and centre. Emily’s side profile entered the frame and the British beauty ran her tongue along Anne’s striking jawline to her forehead, licking up Jake’s cum as she did so. What Emily wasn’t collecting with her tongue, Anne was gathering with her fingers and sucking them clean.
When Anne’s face was clear of cum, the two women kissed each other deeply, the English woman pushing Jake’s load from her mouth into the American’s.
The pair made out for a few minutes, their hands running through each other's hair and over their bodies as Jake filmed. Emily soon stood and then helped Anne to her feet. Holding hands, the two walked into the house, Emily beckoning Jake to follow, which he did, focussing the camera on the swaying asses of the two women as they walked ahead of him.
Once inside the house, Emily and Anne sat down next to each other on a cream sofa in a nicely decorated living room. The pair continued their make out session, Emily’s hands rubbing Anne’s chest while Anne ran her fingers along Emily’s thighs as they kissed.
Emily was first to break the kiss as she moved her mouth to Anne’s ear, nibbling the American’s earlobe lightly causing Anne to shudder and gasp.
“Fuck, Emily, please don’t tease me! Mmm, I got so wet sucking that big cock, I need to cum!” Groaned Anne, rubbing her body against Emily.
“Mmm, as wet as I got watching those perfect fucking lips wrapped around that thick dick? You looked so fucking sexy taking all of that big cock down your throat! Fuck, baby, feel me! Feel how wet my little cunt is for you!” Purred Emily as she took one of Anne’s hands and placed it between her legs while her own hand snaked down to Anne’s wetness.
Jake moved to the pair and angled the camera to catch the action as the fingers of each actress rubbed along the wet pussy lips of the other as they resumed their deep, passionate kissing.
The pair moaned into each other, the sound muffled as held in by their mouths being locked together.
Anne’s fingers ran up and down Emily’s wet lips, getting them covered in her British friend’s juices before they moved to Emily’s swelling clit. She circled the sensitive nub with her fingers before pressing down on the little pleasure button, causing Emily to withdraw from the kiss to moan loudly as she fell backwards onto the couch, causing her fingers to part from Anne’s pussy.
“Oh fuck! God, Anne, touch me! Rub that little clit! Fuck, your fingers feel so good!” Groaned Emily, as Anne rubbed her clit back and forth roughly with two fingers. “God, please, go lower! Put those fucking fingers inside me!”
Anne looked at Emily, her eyes closed and mouth open in the throes of pleasure as Anne stimulated her swollen clit. Anne smiled, a huge devilish grin appearing across her gorgeous face. She slowed her stimulation of her friend’s clit, and crawled up Emily’s body until they were face to face.
Without words, the two women simultaneously brought their fingers to the other's mouth. Both women licked and sucked on the fingers presented, each cleaning their own juices from the other’s digits.
Once the fingers had been sucked clean of the girl cream that coated them, Emily and Anne kissed once more, their juices combining in their mouths. Anne’s sweet cream blended with Emily’s tangier flavour to create a delicious combination.
As they shared their blended juices in a passionate kiss, Anne pulled Emily back to a seated position. Still kissing, Anne adjusted both their bodies so one of her legs was over Emily’s and one of Emily’s legs was over hers. Getting the idea, Emily’s hands ran down Anne’s smooth back and grasped the round cheeks of her friend’s delightful rear. She pulled Anne toward her and the two women groaned into each other's mouths as their wet pussies slapped together.
Jake filmed in close up as best he could as Anne started to grind her pussy against Emily’s. Anne’s clit rubbed against Emily’s, sending shivers across both of their bodies.
The two women’s mouths separated and both vocalised the pleasure they were feeling.
“Christ, I love feeling your wet cunt against mine, Em! Fuck, feeling your wet little clitty rubbing against me is incredible.” Groaned Anne as jolts of ecstasy ran through her.
“God, you sexy fucking bitch! Grind your tight twat into mine! Fuuuck me, fucking scissor me Anne!” Growled Emily, as she pushed Anne backward on the couch and fell backward herself.
Both women, now lying slightly on their sides, rocked their hips back and forth in rhythm, the only sounds in the room being the moans of each woman and the sounds of two wet pussies rubbing against each other.
Emily looked down the couch at Anne, watching as her American friend’s face contorted in ecstasy as their pussies rubbed together. The frantic pace at which Anne moved her hips was causing her round breasts to bounce freely and Emily watched, almost hypnotised, as those twin mounds jumped about on her friend’s chest.
Emily looked at and addressed the camera Jake was pointing at her. “Don’t film me, you fucker, film Anne! Fucking hell, look how good she fucking looks? Have you ever seen anything as beautiful as her? Fuck, I love how she fucks. Men and women, I’ve seen that little slut go fucking mental to get off! Fuuuck, just watching her is enough to make me fucking cream my knickers, let alone what she’s doing right now. Christ, I’m getting close! Keep going Anne, please, let’s cum together!” Purred the Brit, whose own hips sped up their movement back and forth in sync with Anne’s.
Though she sensed her own orgasm to be near and was mostly focused on bringing her and Emily that simultaneous release, she heard Emily’s words and felt she had to respond.
“Hey Mr Cameraman, come over here!” She groaned, beckoning Jake over with one finger. Though the camera was shooting her face, Anne addressed Jake behind it. “If I’m a slut, it’s only because she made me one. God, let me tell you, she released something in me that first night together. She showed me how good a woman can fuck another woman then together we ran through that crew, men and women. Fuck, Em, remember that cute little runner? Must’ve barely been out of college and we made her our little toy. If one of us wasn’t available, we sent this petite little thing to satisfy the other. Mmm, and how about when me and you stayed behind after wrap one night and stumbled on the sound guys poker game? God, even now, I think how good it felt to be next to you as those 7 guys ran a train on both of us. I couldn’t sit right for a week after that, after you convinced me to give up my ass to them. From anal virgin to loving my ass being pounded in 2 hours. God, I’m gonna cum Em! Fuck, grind that pussy against mine! Faster!” Anne panted, as she bucked her hips quickly, speeding up the closer she got to orgasm.
“Yes Anne! Scissor my fucking cunt, you bitch. Oh, you sexy fucking bitch. Fuck, look at me! Let me see that beautiful face as we cum together!” Moaned Emily loudly, her naked body shiny with sweat as she rocked her hips back and forth, trying to match Anne’s speed.
The two co-stars scissored their wet pussies together, their screams of orgasmic ecstasy filling the room mixed with shouted exclamations of curse words and compliments as they both reached orgasm within seconds of one another. They continued grinding on each other through their orgasms, and once both had finished cumming, the two sat up and rubbed their hands over the other’s hot wet sex and licking their combined cum off their fingers.
“God, you’re amazing! I love how good you make me cum!” Said Emily, kissing Anne on the nose before turning to Jake and taking his solid erection in her hand. “Speaking of making someone cum, I see our little show got you nice and ready for me! Give Anne the camera, there’s a good boy” she said, as she sank off the couch onto her knees in front of Jake.
He handed the camera to Anne, who filmed as Emily jerked Jake’s cock in her hand and moved her mouth to his scrotum. The British beauty sucked hard on one of Jake’s balls, before moving up, kissing up the length of his erect shaft to the engorged pink head. She licked the spot where the shaft and head met, causing Jake to groan deeply.
“Oh, he liked that Em. Show him how well you work that mouth of yours!” Said Anne, as the camera captured Emily kissing the large head of Jake’s thick cock, her tongue gliding along the thin opening before opening her mouth and taking the head inside.
The gorgeous English woman sucked deeply on the head of Jake’s cock as her hand moved up and down the shaft.
Taking the cock from her mouth, Emily spat on the erect member, rubbing her wet saliva up and down the shaft with her hand. From her position on her knees, she looked up at Jake, their eyes meeting as she opened her mouth wide and slowly started to take his hard penis deep into her throat.
The gagging sounds the Brit made as Jake’s cock pushed at the back of her throat only spurred her on along with the words of encouragement she was getting from Anne behind the camera.
“Fuck Em, you look so fucking sexy with a cock down your throat. Such a pretty English rose being a depraved slut for dick. Mmm, he’s big, isn’t he? Biggest you’ve had in a while. I know you can do it though. Take him all, hun. Take that thick cock deep, baby. Make him cum, sweetie. Make him shoot his sweet load into your mouth and then share it with me.” Said Anne, pointing the camera at Emily as she quickened her head movements up and down Jake’s cock.
With tears in her eyes, Emily’s hands moved to Jake’s ass. She held his cheeks and pushed him forward, driving all of his cock into her mouth, her nose pressing into his pelvis.
Jake groaned as his cock was enveloped by the soft, warm wetness of Emily’s throat. He knew he was getting close so he put a hand on the back of Emily’s head and started to thrust his hips back, his cock withdrawing inch by inch from his mouth before being thrust forward and once again entering the British woman’s lucious throat.
“Yes, Jake, fuck that pretty face! Use her mouth like it’s her tight British cunt. You’d love to feel that warm, wet pussy loosening around that big, thick cock, wouldn’t you? Maybe next time because we’ll definitely have you around again, big boy! You going to cum, young man? Going to cum over my beautiful friend from her sucking that hard dick?” Said Anne to Jake, her voice exuding a smoky huskiness that, in combination with her words and the feeling of Emily’s oral actions to his cock, put Jake over the edge.
“Oh fuck, here it comes!” He groaned.
As Jake’s orgasm hit, Emily pulled back, removing all but the head of Jake’s cock from her mouth. She sucked hard on the head, her hand frantically rubbing Jake’s shaft, milking his load into her mouth.
Once his orgasm has finished, Jake removed his cock from between Emily’s lips and while still on her knees the English woman looked up at the camera Anne pointed in her face, opening her mouth to show she hadn’t swallowed a drop of Jake’s load.
Anne sank to her knees and kissed Emily, trying to film their faces as they shared Jake’s cum between themselves again.
The kiss ended, and each woman swallowed the cum in their mouth, looking at the lens of the camera as they did and opening their mouths again to show that not a drop remained. The pair kissed each other softly on the lips and Anne turned off the camera.
“Mmm, he’s so yummy” said Anne, standing and assisting Emily back to her feet as she nodded in agreement. They looked toward Jake, who had gone back outside to retrieve his discarded clothing. He picked up his pants and boxers and took his phone from his pocket.
Seeing he had some time until his next scheduled appointment at 11, he dressed and walked back inside, where Anne and Emily were sitting together on the couch, Anne’s long slender legs across Emily’s lap, Emily’s finger running up and down Anne’s shin.
“Are you going?” Asked Emily as she saw Jake enter now fully dressed.
“Yep, just booked an Uber, it’ll be a few minutes.” Replied Jake.
“Great. Your payment is on the table by the door, grab it on your way out. It was five hundred, right?” Said Anne, indicating with her hand.
Jake nodded.
“But, before you go,” said Emily, “You have to settle our little bet!”
“Right, yeah. Tell us Jake, which of these pretty little mouths did the better job in that lucious dick of yours?” Asked Anne.
“That’s not fair, you were both incredible.” Said Jake.
Anne shook her head. “No, none of that silliness. We’re both big girls, we can both handle it if you say it was the other. Right, Em?
Emily nodded in agreement. “Absolutely, Anne. It’s a friendly contest, we’re not going to be mad about it.”
“Well, then, if it’s not a big deal, Anne is better.” Said Jake.
“YES! I told you, Em! I’M THE CHAMPION!” Said Anne in celebration as Emily frowned.
Anne jumped up off the couch and started to dance, swaying her hips as she turned herself around while taunting Emily.
“Na na na naa naa, I give better head than you!” Sung Anne.
Emily looked up at her friend from the couch and her frown disappeared. A huge beaming smile crossed her face as she looked at her dorky friend. She grabbed Anne by the arm and pulled her back down, kissing her friend as she fell into her arms.
The two former co-stars renewed their make out session, their hands roaming and rubbing over each other's bodies.
Tearing his eyes away from the stunning sight unfolding again in front of him, Jake turned to leave. He made his way out of the house, grabbing the envelope from a side table as he exited.
He walked to the road and waited. As he did, his phone started to ring. He looked at who was calling. Aubrey. He answered.
“Good timing, Ms Plaza, I’ve just finished my first appointment.” He said.
“Are you on the way back to the hotel?” Asked Aubrey.
“I’m waiting for my car to arrive, then I will be, why?” Jake enquired.
“Don’t, I’m gonna send you an address, go there instead. It’s kinda a surprise, I’ll fill you in when you get here. See you soon.” Aubrey told him before abruptly hanging up.
Now filled with curiosity, Jake saw the message Aubrey sent him pop up on the screen of his phone as his Uber arrived.
He got in and gave the driver the new address and the car set off.
A short time later, the car arrived outside a fairly large house in the Hollywood Hills.
Jake exited the car, and walked to the front door. As he was about to knock, the door opened and there stood Aubrey.
“Welcome to your humble new abode while you’re here in LA!” She exclaimed.
“Umm, I’m sorry?” Said Jake, confusion evident in his voice.
“I was sitting in that hotel room after you left and felt bad about you having to keep travelling back and forth all of the time, so I took the initiative to rent this place through AirBNB for the next few weeks. It’s relatively close to the city for you to get to your appointments there and can even have appointments come here and you can clean yourself up after without all that boring car travel. I think it’s perfect. And don’t worry about cost, I’ll take care of that. Think of it as an incentive for retaining my services. Just one of many, may I add.” Explained Aubrey, emphasising her last words by rubbing her hand over the crotch of Jake’s pants and licking her lips seductively. “Now, I’ve got to go, but I’ll be back later and can give you the full tour. Your bags are in the bedroom, I bought them with me. Bathroom is down the hall there and to the left, you’ll find it. Hurry, because your next little slut is coming here in about half an hour. Toodles!” Said Aubrey, as she walked to the door and exited.
Slightly taken aback, Jake walked to where Aubrey said the bathroom was. He removed his clothes and took a shower. Once complete. He wrapped a towel around his waist and walked around the house, checking out the rooms and finding the kitchen.
Checking and seeing that the fridge was well stocked, he took out a carton of orange juice and poured himself a glass. He walked to the entrance area and toward the large open living room, looking out of the large glass windows at a swimming pool and beyond that the view of the city as he finished his drink.
Jake went to the bedroom and from his bags took out a pair of shorts, putting them on commando as he figured they’d be off again soon.
He continued investigating the house and was soon alerted by a doorbell ringing.
He went to the front door and opened it, the person outside pushing past him and into the living room, wearing a long raincoat, large hat and sunglasses.
Jake closed the door and was about to turn around to speak to his guest when they spoke up first.
“Eyes closed, just give me a second.” Said the mystery woman. Jake didn’t recognise the voice, but they sounded young.
Jake did as he was told and waited for the mystery woman to be ready.
About 30 seconds later, the woman spoke again.
“Okay, I’m ready!” said the woman.
Jake opened his eyes and turned around but looked at the floor as he moved toward his client.
Jake wanted to take in every inch of his client before seeing who it was, so starting at her small feet clothed in a pair of long white socks, his eyes moved upwards, studying the long slender legs, socks going all the way up past her knees to her smooth thighs, the visible bare skin looking so soft. Continuing upwards, Jake saw a very short tartan skirt he estimated to be maybe 4-5 inches from waist to hem. Above that, his guest’s slender tummy and abs exposed as a white shirt was tied just below the woman’s small breasts and the buttons visible were undone, showing the white bra she was wearing.
Jake’s gaze continued upwards, along the smooth skin of his client’s neck to her face. He didn’t recognise who he was looking at but she was definitely attractive. Finally, Jake looked and saw this woman’s blonde hair was done up into two pigtails, one either side of her head.
“Hi, it’s Jake, right? I’m Kiernan, nice to meet you!” said Kiernan Shipka, a big smile on her face to match her bubbly demeanour.
“Hi, Kiernan, what would you like today?” Asked Jake.
Kiernan paused for a second, lowering her head and breathing deeply. When she looked up, her face had changed. Now sporting a look of innocence, she moved toward Jake and put a hand on his chest.
Kiernan looked at Jake in his eyes and said “I want you to teach me how to fuck, Daddy!”
===To Be Continued===
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Nice job! This was just really well written. And hell, at one point, the women offered the husbands to join in if they ever did it again, so there's no hard feelings lol.
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Thanks. Established relationships are tricky to work around. It’s either indicate it’s an open thing like with Anne and Emily’s husbands, or ignore it like I did with Mary in Chapter 3
Nice job! This was just really well written. And hell, at one point, the women offered the husbands to join in if they ever did it again, so there's no hard feelings lol.
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Chapter 6: Teaching Kiernan
Jake opened his eyes and turned around but looked at the floor as he moved toward his client.
Jake wanted to take in every inch of his client before seeing who it was, so starting at her small feet clothed in a pair of long white socks, his eyes moved upwards, studying the long slender legs, socks going all the way up past her knees to her smooth thighs, the visible bare skin looking so soft. Continuing upwards, Jake saw a very short tartan skirt he estimated to be maybe 4-5 inches from waist to hem. Above that, his guest’s slender tummy and abs exposed as a white shirt was tied just below the woman’s small breasts and the buttons visible were undone, showing the white bra she was wearing.
Jake’s gaze continued upwards, along the smooth skin of his client’s neck to her face. He didn’t recognise who he was looking at but she was definitely attractive. Finally, Jake looked and saw this woman’s blonde hair was done up into two pigtails, one on either side of her head.
“Hi, it’s Jake, right? I’m Kiernan, nice to meet you!” said Kiernan Shipka, a big smile on her face to match her bubbly demeanour.
“Hi, Kiernan, what would you like today?” Asked Jake.
Kiernan paused for a second, lowering her head and breathing deeply. When she looked up, her face had changed. Now sporting a look of innocence, she moved toward Jake and put a hand on his chest.
Kiernan looked at Jake in his eyes and said “I want you to teach me how to fuck, Daddy!”
Jake’s eyes grew wide in surprise at the boldness of the young beautiful blonde. He hadn’t expected any role play would be involved.
Kiernan pressed on.
“All the other girls at school are always talking about how they’ve all had sex with their boyfriends and I just want to fit in so I thought if I told them I’d had sex with someone older, then they’d be my friends. You want me to have friends at school, don’t you daddy?” She asked in a childlike voice.
Jake paused for a moment, thinking of his character in this scenario, before looking directly into Kiernan’s beautiful eyes.
“Of course I do, sweetheart, but it would be wrong.” Said Jake, not wanting to directly bring up the topic of incest, but Kiernan’s next sentence clarified the situation.
“Why would it be wrong? You’re only my step-dad, and mommy doesn’t have to know! She’s away with work, it’s just us two here!” Kiernan said with a wink and a giggle.
In character, Jake hesitated and thought it over before deciding to go with it.
“Sit with me on the couch, honey!” Said Jake, as he moved to the plush couch in the living room and sat down.
Kiernan followed and sat on the other end of the couch cross legged. Jake looked over and could see that she wasn’t wearing any underwear and her bald pussy was on full display.
“So, sweetie, how much do you know about sex?” Jake asked.
“I know that when a boy really likes a girl, his penis gets really hard and he can put it inside the girl until he has an, um, ejaculation?” Said Kiernan, as if reciting a memorised section of a textbook.
“Do you have any experience with sex at all? I would hope not but have you seen a real live penis before?” Asked Jake.
“Never in person but one time at a sleepover, this girl brought over this magazine which had a lot of pictures of naked men and I looked through it and I felt myself get wet in my panties a little bit!” Said Kiernan, bashfully.
“That’s good, that’s normal. Would you like to see a real life penis?” Jake asked the petite blonde.
“Ooh, yes please, daddy!” Kiernan replied, smiling.
Jake stood up and moved to stand in front of Kiernan.
“Unzip my pants, sweetie and pull them down.” Said Jake.
Kiernan followed Jake’s request while Jake removed his shirt. His semi erect cock gave his boxers a very evident bulge that Kiernan looked at intently. She looked up at Jake.
“Can I take your boxers off too, daddy?” She asked.
“Sure thing, sweetheart,” said Jake.
Kiernan pulled Jake’s boxer shorts down by the waistband and his semi erect penis sprung up, nearly hitting Kiernan in the face. She looked at Jake’s cock and moved her head around to study it from other angles.
“Wow, daddy. Your penis is so big!” She said in amazement.
“You can call it other things too, honey, like cock or dick.” Said Jake.
Kiernan giggled. “I like cock.” Said the blonde, the devilish look she gave Jake betraying her character.
“So what do these other girls in school talk about what they’ve done with their boyfriends!” Asked Jake.
“Well, they talk about having sex or fucking and some of them talk about giving handjobs and blowjobs, I think?” Said Kiernan.
“What do you think either of those involve?” Asked Jake.
“I guess a handjob is just rubbing it with my hand, like this?” Replied Kiernan, as she placed her palm against the top of Jake’s penis and rubbed her hand up and down the length of it.
Kiernan’s hand felt so soft against his cock and Jake closed his eyes as a rush of pleasure surged through him.
“Mmm, that’s pretty close sweetie, but what the girl actually does is put their hand around the cock, like a water bottle and then move their hand up and down.” Said Jake.
“Like this, daddy?” Kiernan asked, as she wrapped her small hand around Jake’s cock and started to jerk him off as her pretty face looked up at him.
“Oh god, yes, just like that baby!” Groaned Jake, feeling his cock get harder in Kiernan’s hand.
“What if I use both hands, daddy?” Said Kiernan, her other hand also wrapping around Jake’s cock, both hands moving slowly up and down the shaft.
“Fuck, that’s even better!” Moaned Jake. “So this is a handjob, you seem to have this down. Do you know what a blowjob is?”
“Is that just blowing on it, like this?” Said Kiernan as she pursed her lips and blew cool air onto Jake’s cock.
“Oh god, that feels incredible but no. No, a blowjob is when a girl puts a boy’s cock into her mouth. Why don’t you give it a try?” Said Jake, his hand running across Kiernan’s hair.
“Okay daddy, whatever you say!” Said Kiernan with a smile.
Kiernan opened her mouth and took the swollen head of Jake’s member inside, closing her lips around it.
“Oh fuck!” Moaned Jake, as Kiernan’s warm mouth engulfed the head of his cock. “Keep using your hands too, baby!”
Kiernan followed the instructions to the letter, moving both hands up and down Jake’s cock as she sucked on the engorged head.
Jake’s hands moved to the back of Kiernan’s head and he started to slowly thrust his hips to push his cock further into the petite blonde’s mouth.
Kiernan’s lips were soon halfway along Jake’s shaft and the gorgeous young actress began to gag as the hard member started to rhythmically move in and out of her throat.
Jake removed his cock from Kiernan’s mouth as she started gagging. Kiernan gasped for breath and let a large amount of saliva drip from her mouth.
“Sorry baby, daddy got a little carried away, maybe a bit too much for your first time!” Said Jake, staying in character while his real life intuition said the pretty young blonde kneeling before him was no stranger to throating a large cock.
“Nooo, I liked it, daddy! Mmm, I felt my little pussy getting wetter and wetter as you pushed more and more of your hard cock into my mouth. Do you want to see?” Kiernan asked.
“Of course, baby!” Replied Jake.
Kiernan turned and lay back on the couch. Taking hold of the hem of her extremely short skirt, Kiernan pulled the clothing up and revealed her pussy to Jake.
Jake’s eyes were drawn immediately to the bald mound between the young blonde’s smooth, slender legs. Kiernan’s pussy was plumper than Jake expected and it glistened with the blonde’s juices.
“God, such a perfect little pussy.” Said Jake, placing his hand on Kiernan’s firm abs and moving it down to her pussy. “Would you like me to touch your pussy, baby?”
“Mmm, yes please, daddy!” Whimpered Kiernan before moaning as Jake’s fingers ran over her clit and along her juicy pussy lips.
Pleasure coursed through Kiernan as Jake’s fingers softly rubbed her pussy.
Kiernan closed her eyes and a series of slow moans escaped her slightly agape mouth.
“Yesss, daddy. Touch your step-daughter’s pretty little pussy! God, let me suck your hard cock again while you rub my pussy, please!” Moaned Kiernan, her hand moving up to rub against Jake’s cock.
Jake paused, then lifted Kiernan up from the couch. He turned around and sat down, then lay back on the couch. He manipulated Kiernan’s body until her face was aligned with his cock while the blonde’s toned little ass and dripping plump pussy were in front of Jake.
“Now, honey, this is called a sixty-nine. Remember, it’s not just the man who needs to be warmed up before sex, the woman needs to be ready too.” Said Jake, as he gazed in wonder at Kiernan’s pink pussy and firm ass inches from his face.
Jake extended his tongue and leaned in to get his first taste of Kiernan, the blonde’s sweet nectar immediately intoxicating him.
“Oooh, daddy! Is that your tongue? Mmm, it feels so good how you’re licking me! I want to make you feel good too!” Moaned Kiernan, lowering her head and taking Jake’s cock back into her mouth.
Wanting to reward Jake for playing his role so well and in response to how good he was making her pussy feel with his tongue, Kiernan dropped character and after timidly sucking on the head of Jake’s cock, she took a deep breath in through her nose and lowered her mouth all the way down Jake’s shaft.
“Shit!” Groaned Jake, tearing himself away from Kiernan’s dripping pussy as he felt his cock enveloped in the young blonde’s snug mouth and throat. He brought his fingers to Kiernan’s pussy to replace his tongue.
Kiernan made herself weep, her eyes filling with tears as she let her mouth fill with saliva. She wanted to replicate for Jake how she looked the first time she’d deep throated a cock. To add to the pretence, Kiernan made exaggerated gagging sounds despite Jake’s cock resting comfortably in her throat.
Stepping back into character, she quickly moved her head back up off Jake’s cock. Strands of saliva hung from her mouth and clung to the erect shaft and Kiernan looked back at Jake while her hand fondled her scrotum.
“I’m sorry, daddy. Your cock just looked so yummy and with how good it felt earlier I just had to try and take it all. Did it feel good, daddy?” Asked Kiernan with a giggle and groan of pleasure as Jake’s fingers tickled her tender clit.
“It felt incredible, baby!” Moaned Jake.
“Yay, I’m so glad you liked it, daddy!” Squealed Kiernan before she lowered her head back down onto Jake’s cock.
The blonde bounced her head on Jake’s shaft, sloppily coating his hard cock with her saliva. In return, Jake returned his mouth to Kiernan’s pussy, lashing his tongue against the petite actress’s clit.
The pair stayed in this position for a few minutes, orally pleasuring one another until Kiernan felt the initial surges of her orgasm start to build.
“Fuck daddy, feels so good! God, keeping licking me, daddy! Keep licking your little girl’s plump little pussy!” Moaned Kiernan, lifting her head from Jake’s cock and substituting her hand for her mouth, stroking the slick shaft up and down slowly.
Wanting to push Kiernan over the edge into her orgasm, Jake brought two fingers to her pussy and pushed them inside her pink hole, curling them downwards as they entered to rub her g-spot.
“Fuuuck, yes Daddy! Finger my little pussy! Make me cum, Daddy! Make your little girl cum all over your fucking fingers! Ohhh shit, I’m cumming!” Moaned Kiernan, as her orgasm hit.
The blonde’s petite body shook as waves of ecstasy ran through her. She had been holding herself up with one arm and as she came, she moved her arm to her ass.
Kiernan’s front half collapsed onto Jake, her covered breasts pressing into his stomach as her pretty young face came to rest on Jake’s thigh besides his stiff cock. In between moans, Kiernan softly kissed the swollen member while at the other end of her body, she spread her ass cheeks to allow Jake to see her little pink asshole pulsating as she came.
Kiernan’s orgasm soon passed, and the lithe blonde stood up off the couch and stood before Jake, who sat up on the couch.
“Daddy, that was amazing, but I need more!” Purred Kiernan.
With Jake now in a seated position, Kiernan straddled him, putting one smooth leg on either side of Jake’s hips.
She positioned herself above Jake so her dripping pussy was mere centimetres above Jake’s hard cock, close enough that he could feel the heat emanating from the blonde’s pussy.
Jake placed his hands on Kiernan’s hips and ran them up her firm young body.
Upon reaching the blonde’s white shirt, Jake untied the knot situated just below Kiernan’s perky breasts and undid the one button remaining.
Kiernan removed her shirt, letting it fall to the ground behind her and then she moved her hands to the front clasp of her bra.
The blonde unclasped her one item of underwear and shifted her arms to let it also fall from her body to the ground.
Jake stared at the blonde’s perky little breasts with a fever of lust before bringing his mouth to one of Kiernan’s hard pink nipples and sucked on it, his hand moving up to pinch the blonde’s other nipple.
As Jake paid expert attention to her breasts, Kiernan’s hand reached down and held Jake’s cock and lowered herself down, her pussy lips parting to allow entry to the hard shaft.
Kiernan and Jake moaned in unison at this initial penetration and their eyes met. As the pair gazed deep into each other’s eyes, Kiernan began to slowly lower herself down onto Jake’s cock. The blonde’s eyes widened and her mouth gaped open as her pussy was filled by Jake’s long, hard cock.
“Ohhh fuuuck! Fuck, you’re so big, Daddy! God, your huge cock is filling my little pussy so fucking good!” Whimpered Kiernan as her pussy reached the bottom of Jake’s shaft.
“Mmm, you’re so tight, baby!” Groaned Jake, as Kiernan slowly started to bounce her slim body up and down on his cock.
Jake’s hands moved down to Kiernan’s hips and around to her ass beneath her skirt, one firm cheek in each hand.
As his fingers firmly kneaded the soft flesh of the young blonde’s impeccable butt, Jake started thrusting his hips upwards in time with Kiernan’s movements.
“Yes! Fuck me, Daddy! Fuck my sweet little pussy with your big cock! Mmm, I’ve seen you looking at me when I’m by the pool, sunbathing in a bikini. Trying to hide how hard my tight little body makes your cock! You’ve wanted me, haven’t you Daddy because I’ve wanted you. Why do you think I’m always walking around in booty shorts and crop tops? I’ve wanted you to fuck me for so long! Fuck me! Fuck me so hard no other man will compare! Make me a slut for my stepdaddy’s dick! Fuck, you’re so deep in my tight little cunt and it feels so fucking good!” Moaned Kiernan, throwing her head back and letting out a guttural moan as Jake’s cock pushed deeper inside her than almost any man had before.
“Language, young lady!” Groaned Jake, through gritted teeth. Kiernan’s words in combination with how incredibly her pussy was squeezing his cock were bringing Jake to the edge.
“You gonna punish me for saying such dirty things, Daddy?” Said Kiernan, her hands caressing Jake’s chest as she looked down at him.
In one movement, Jake put his arm across Kiernan’s back and whilst remaining inside the blonde, Jake pulled Kiernan down so she was lying on the couch.
Jake put one of Kiernan’s legs on each shoulder and lowered himself so the blonde’s knees were at her chest and the pair were face to face.
In this new position, Jake started to rapidly thrust himself in and out of Kiernan, his thighs slapping rhythmically against the blonde’s ass.
Jake looked down at Kiernan, the blonde’s pretty face a mask of pleasure with her eyes closed and mouth wide open as she gasped with each inward thrust he made,
Kiernan’s gasps and moans got closer and louder as her second orgasm approached.
“Yesss Daddy, keep fucking me! Mmm, you’re gonna make me cum again, all over that beautiful big daddy dick! Will you cum with me, Daddy?” Kiernan groaned as she ran a hand down her rock hard stomach and brushed her fingers against her swollen clit.
“I’m close too, tell me where you want it sweetie!” Moaned Jake, quickening the pace of his thrusts even more.
“Mmm, I want it inside me. I know it’s wrong, but I want to feel Daddy’s hot load dripping out of me as I walk back to school. Will you do it, Daddy? Will you please cum inside me? I want it so bad! I want to be claimed by your hot cum, Daddy!” Squealed Kiernan, her orgasm closing in.
The way Kiernan’s pussy squeezed his cock in combination with the dirty talk erupting from the blonde’s mouth brought Jake to his brink.
“Fuuuck, I’m gonna cum, baby!” Jake grunted.
Jake thrust in and out of Kiernan a few more times before plunging himself deep into the young actress and letting his cum shoot inside her.
“Ohhh, I feel it, Daddy! I can feel your hot cum inside meee!” Screamed Kiernan as she frantically rubbed her clit and her orgasm hit.
Kiernan’s pussy got tighter as she came, her sex practically squeezing every last drop of cum from Jake.
Once he was spent, Jake kept his quickly softening cock inside Kiernan as her own orgasm shortly subsided, then pulled out.
On his knees on the couch, Jake looked down at Kiernan. The gorgeous blonde looked absolutely ravishing. Her pigtails were messy and her face and those small but perfectly formed breasts were glistening with a thin sheen of sweat.
His eyes roaming further downward to Kiernan’s pussy, the plump lips were slightly open and Jake could see his cum slowly seeping out.
“Admiring your handiwork?” Asked Kiernan, sleepily.
“Just a little. How are you doing, baby girl?” Jake asked.
“Please, call me Kiki.” Said Kiernan, lifting herself to a seated position before standing and moving to a rucksack nearby Jake hadn’t previously noticed.
Jake watched as Kiernan opened the bag and took out some alternative clothes.
He watched Kiernan remove her skirt and put on a pair of pink panties before his attention was diverted by the ringing of his phone.
Jake rummaged in his own discarded clothes and found his phone, alerting him to an incoming FaceTime call from Aubrey. He walked into another room and answered.
“Hey!” Said Jake, immediately noticing that Aubrey’s face was flushed.
“Just to, oh, let you know that, mmm, there’s a bit of a delay with your next client, there’s uh traffic or, or something.” Said Aubrey, evidently unfocused.
“No worries, just finishing up here and I’ll wait for them. Are you okay? You seem a little not with it right now?” Said Jake, having an inkling what Aubrey was doing.
He was soon proven wrong as Aubrey turned her camera around. Jake had assumed that Aubrey was masturbating but he soon saw much more interesting.
Between Aubrey’s legs, Jake could see the red hair and striking eyes he recognised from somewhere.
“Good girl, Sadie, such a good girl eating Mommy’s pussy so well! Say hi to Jake, Sadie!” Said Aubrey.
The full face of the redhead on the phone came into view and Jake recognised the gorgeous actress from Stranger Things.
“Hi Jake!” Said Sadie Sink before returning to her task of licking Aubrey.
“Mmm, make me cum, Sadie! Make me cum and maybe I’ll give you a discount for a couple of hours with Jake and that wonderfully large cock of his.” Moaned Aubrey.
“You’re having fun, I see!” Chuckled Jake.
“Someone has to keep these youngsters in line! Anyway, I’ll check in later, see ya!” said Aubrey, hanging up the phone.
Jake walked naked back to the living room and saw Kiernan was standing near the front door.
“Thought it’d be rude to just leave.” She said, opening the door.
“Then thank you for the courtesy!” Said Jake, smiling.
“You were incredible. You should do improv, you’re really good at it!” Said Kiernan.
“Not so bad yourself!” Laughed Jake.
“Maybe next time, it won’t just be a two person scene. Bye!” Said Kiernan as she exited with a wave.
Jake closed the door and laughed more to himself.
He made his way to the bathroom and turned on the shower, stepping into the hot spraying water.
Jake stood for a short time with his eyes closed, just letting the water flow over him as he thought how much his life had changed in such a short time. Barely a week ago, he’d taken a job in New York that had led him to LA. He’d had sex with women he’d never in a million years had thought he would be with and possibly would make more money in the next few days than he ever had before.
Jake got so wrapped up in thinking about how he’d got here, he didn’t hear the bathroom door open and didn’t hear someone enter the shower behind him.
His first awareness of someone else with him was a hand reaching around his body to grip his cock and start jerking him.
His eyes shot open and he turned around to see Kiernan before him, also naked.
“I thought you left?” He asked, before Kiernan put a finger on his lips.
“Don’t talk!” She said, quietly.
She rubbed Jake’s cock until it was hard then turned around. Holding onto a nearby shower rail with her free hand, she guided Jake’s erect cock between her slim ass cheeks and positioned his head at her asshole.
“I got down to my car on the street and realised I needed more.” Said Kiernan, pushing back and letting Jake’s cock push into her ass.
“Oh fuck, that hurts! Fuck my little virgin ass, Jake. Yes, take my anal cherry! I love a big cock in my mouth or my juicy little cunt, but never had a cock in my ass before! All those guys with their big cocks wanted it but I always told them maybe next time and then ghosted them! They had the equipment but didn’t know how to use it! Not like you, you’re a master with that cock, no-one has made me feel like you did! I knew there had to be a next time and as I walked down the driveway feeling your hot cum dribbling out of my pussy, I started thinking how hot it would be to feel my little asshole stretched so wide around a big dick and I knew next time had to be right now! Ohh, I was so right. It hurts but it feels so good! Fuck me, Jake, fuck my tiny little ass!” Moaned Kiernan, grimacing as Jake’s cock slid slowly into her previously unviolated hole.
As the hot water of the shower poured down onto their naked bodies, Jake had both hands on Kiernan’s slender hips and was slowly thrusting into her ass.
Jake knew from experience that water itself wasn’t an ideal lubricant and while she said she liked the pain, Jake didn’t want to hurt Kiernan. Looking around, Jake spied a bottle of lotion on a nearby shower shelf.
He reached up and took the bottle, opened it and squirted a large amount onto his cock, then dropped the bottle and rubbed the lotion onto his cock and around Kiernan’s asshole.
Even with the added lubrication, Kiernan’s asshole was still giving resistance to Jake’s cock.
Holding Kiernan’s hip with one hand, Jake slid his other hand around to the front of the blonde and let his fingers slide over her clit.
“Just breathe and try to relax.” He said to Kiernan, who looked back at him with tears in her eyes. The stunning young blonde nodded her head and did as Jake instructed.
Kiernan breathed deeply as Jake continued pushing forward, still going slowly. Soon, his thighs were pressed against the back of Kiernan’s legs.
“Oh, fuck! Fuck, you’re all the way in my ass!” Moaned Kiernan.
Jake looked down and gazed at the young woman’s ass cheeks pressing against his pelvis.
“I’m just gonna stay like this for a minute, let you get used to it, okay?” He asked Kiernan.
“Mmhmm!” Replied Kiernan.
The pair stayed still for a minute or so, before Kiernan again looked back at Jake and nodded.
“I’m ready.” She said, quietly.
Jake started to pull his cock from Kiernan’s ass slowly, stopping when just the thick head of his cock remained inside.
He thrust forward at a quicker pace, burying his length in the blonde’s tight rear.
Kiernan whimpered softly in both pain and pleasure as Jake thrust in and out of her ass.
His pace quickened with each thrust and with both his hands on her hips for balance, Kiernan took over the stimulation of her pussy.
Her fingers caressed the increasingly wet lips of her plump pussy before two slid inside.
Kiernan curled her two fingers upwards inside her pussy and pressed them against the spongy textured flesh of her G-spot while rubbing her thumb against her clit on the outside.
The wave of ecstasy that crashed over Kiernan eliminated any pain and discomfort she felt having her asshole penetrated, leaving only a pleasurable feeling.
“Yesss! Fuck, that feels so good! Feels so good to have such a big cock in my tight little butt! God, if I knew it could feel this good, I would’ve given up my ass ages ago! You like it, Jake? You like fucking my little asshole?” Moaned Kiernan.
“Fuck, it’s incredible. Such a perfect little ass, squeezing my cock so good!” Jake groaned.
Putting one hand on each of Kiernan’s toned ass cheeks, Jake spread the young woman’s ass and removed his cock completely.
Jake gazed in wonder for a few seconds as Kiernan’s asshole gaped open before him, before pushing his cock back inside the stunning blonde, grunting as her tight anal walls clenched around his hard shaft.
“Mmm, yes, make me gape, Jake! Make my pretty little asshole open like I’m some little porno slut. Ohh god, keep fucking me, Jake! Fuck me hard! Fuck my ass whilst I finger my little cunt! Fuuuck, I’m gonna cum so fucking good!” Kiernan moaned.
“You want to be a slut, Kiernan? More of a slut than letting a stranger cum inside you then letting him fuck your ass? Cum for me then show me how slutty you can be!” Jake growled, his thighs slapping against Kiernan’s butt as her fucked her.
The thought of what Jake meant by that and the combined sensations of her frantic fingering and the intense pounding of her formerly virgin ass caused Kiernan’s orgasm to surge through her.
“Oh, fuck! Yes! Yes, I’m cumming!” She screamed.
Jake continued thrusting into Kiernan as she came, her asshole gripping his cock tightly as it contracted around him.
He held Kiernan up as she came and once her orgasm subsided, he removed his cock and spun the blonde around in the shower.
“On your knees!” Said Jake, pushing down on Kiernan’s shoulders.
Kiernan did as he asked, her knees pressing into the hard tile as she knelt before Jake.
Gripping her blonde hair, Jake guided his cock to Kiernan’s lips and pushed into her mouth.
Kiernan took Jake’s whole length into her mouth and throat, tasting her ass for the first time and finding herself liking the flavour.
Holding Kiernan’s head in place by her hair, Jake started to thrust himself in and out of Kiernan’s mouth, facefucking the pretty young blonde.
Jake didn’t last much longer, the need to release rising inside him.
He thrust his cock into Kiernan’s mouth a few more times and just before he came, he pulled his cock from her mouth and pointed it at the blonde’s beautiful face.
Jake’s cum sprayed forth and painted Kiernan’s face and chest. Once it seemed his orgasm had finished, Kiernan took the head of Jake’s cock into her mouth and sucked deeply, getting the last remnants of Jake’s cum into her mouth.
Kiernan stood and scraped Jake’s cum into her mouth with her fingers, licking her digits clean as she did so. Her and Jake cleaned themselves up in the shower and dried themselves off.
Leaving the bathroom, the pair walked naked to the living room. Kiernan gathered her previously discarded clothes and redressed while Jake put on the clothes he was wearing when Kiernan first arrived.
“That was amazing!” Said Kiernan, smiling brightly. “I’m gonna tell all my friends about you!”
“Well, word of mouth is key!” Chuckled Jake.
“I’m serious, I’ve got a whole bunch of friends in this industry I know would love to be fucked like you fucked me today! Hell, I might even join them if they come to see you.” Said Kiernan with a devilish grin.
“I look forward to it!” Jake said with a smile.
“Shit, I gotta go, I’m late enough as it is” said Kiernan as she looked at her phone.
She quickly walked over to Jake and pulled him in for a deep kiss, their tongues briefly twisting around each other before Kiernan pulled away.
“Bye Jake!” She said as she hurriedly walked to the door and exited.
Jake went out to the pool and removed his shirt.
He dived into the pool and started to swim lengths back and forth.
He did this for around ten minutes before he heard the doorbell chime.
He lifted himself out of the water and walked into the house and across to the door.
He opened the door and his eyes widened.
The brunette woman who rang the doorbell extended her hand. “Hi, Jake? I’m…” was all she could say before she was interrupted.
“Winona Ryder…” said Jake.
===To Be Continued===