Olivia Wilde: Make A Wish Upon A Star
This is a work of complete fiction. It just popped into my brain so I wrote it down and share it for free and make no money off of it. No one under legal age may read this, if you know what’s good for you. No one over legal age should read this for the same reason. All characters used in this story are a parody of any real or fictional person. I don’t know Olivia Wilde or have anything to do with her. Comments are always welcome and appreciated and you should feel free to share. Story Code: M/F, Teen, First Time Olivia Wilde: Make A Wish Upon A Star By Muhabba “Bullshit!” Kevin yelled out in defiance before breaking down into laughter. Doug blushed in embarrassment. “I just want it to be special. It’ll be my only Senior Prom and I want to go with someone meaningful,” he muttered meekly. “Bullshit,” Dennis sobbed through his tears of laughter. “It’s ‘cuz you already asked half the girls in class and got turned down.” Doug looked at his two friends through hazy, tear filled eyes. They’d all been friends since elementary school but, where as his friends had become handsome and cool through the years, he’d become dumpy and introverted. They’d been to two Senior Proms already, and even scored afterwards, while he had barely been able to talk to a girl much less been able to ask anyone on a date. He glared at his computer screen and came to a decision. Even though he knew she’d never reply, at least he could say that he didn’t have a prom date because he had been holding out for the best date possible. “Bullshit!’ he called out and jabbed the Enter key as hard as he could. Kevin and Dennis immediately stopped laughing and stared at Doug in wonder. “Bullshit you didn’t,” Kevin mocked. “Bullshit I did,” Doug replied as he crossed his arms and smiled smugly. “It’s Olivia Wilde or nobody.” Kevin and Dennis went back to laughing. —– “I can’t believe you lied to me, Jason!” Olivia yelled at her husband. Jason Sudeikis sighed in frustration. He had no idea how to handle this. It was true that he was an actor like his wife but where Olivia Wilde was a serious actor that he was sure would win an Oscar one day, he was a comedic actor. When anything happened you could count on him to crack a joke but whenever something happened with Olivia, drama. “It’s not that big a deal,” he said defensively. “Don’t try to play me off like it was no big deal! You lied to me, Jason!” Olivia shot back. Jason rubbed the bridge of his nose. “Everybody told me not to marry an actress,” he told himself, “but no, I didn’t listen. Funny, sweet, intelligent, sexy as hell, I just couldn’t resist despite the drama.” At first he had been too nervous to ask Olivia out but then she had actually tracked him down and asked him out and like any straight guy there was no way he’d say no to a date with Olivia Wilde. Besides being a great actress, she’d appeared in numerous magazine and films wearing little or no clothes and it had been weird not to go out on a date with a girl he had masturbated to furiously for years. “I didn’t lie,” he said in exasperation. “Bullshit!” Olivia shouted. The argument had started when she had woken up this morning, put on her robe and then found out what Jason had done. Now, two hours later she was still in her robe and the argument was still going on. “I’ve always been honest with you and you pay me back with nothing but lies!” she yelled. “Now that’s taking it a bit far,” Jason said, trying to make Olivia see reason. “Everybody’s got something they’ve held back. What about that stupid Tweet you got from the kid last week. You never told me about that.” Olivia threw up her arms as she yelled back, “I didn’t tell you about it because it was no big deal. Hell, it was one of the tamer ones I’ve ever gotten.” “See,” Jason said, “It was no big deal so you didn’t tell me.” “This is different,” Olivia growled. “I didn’t not tell you unlike you told me something and then lied about it instead of not telling me.” “OK, I’m not sure that was even a sentence,” Jason said. “I got to get to work, we’re filming in an hour. We’ll talk later, OK?” He leaned in for a kiss and Olivia huffed and walked past him. “That’s my girl. Love you,” he said as he opened the back door. “Or maybe you’re lying about that too!” Olivia shouted back an instant before Jason closed the door behind him. An hour later Olivia was still fuming at her husband’s lie. She was toying with the belt of her robe when a wicked idea came to her causing her to smirk evilly. Putting the coffee down that she hadn’t been able to enjoy because of Jason, she went to her computer and accessed her Twitter account. “I’ll show him what he gets for lying to me,” she chuckled. —– The next week Doug got out of the limo and tried to smooth out the wrinkles in his tux. He turned around and held his hand out to his prom date and Olivia took it as she got out of the limo she had rented for them and his friends. Olivia appeared to gracefully unfold from the back seat as she got out and posed for all of the students who were staring at her in shock and surprise. “I guess I choose the right dress,” she whispered to Doug as she gave him her arm. He looked so cute and nervous as he tried to adjust his tux and she tried not to laugh at him as his hands fluttered and his eyes looked her over. She had decided to wear a simple, spaghetti strap green silk gown that hugged her like a second skin and clearly showed that she wasn’t wearing a bra. The top of the dress was cut nearly indecently low to show off her chest and cut up her thigh nearly indecently high to show off her leg. And if someone happened to be watching at just the right time the split up her dress made it obvious she wasn’t wearing underwear. Once inside the gymnasium Doug turned nervously to Olivia, his eyes once again crawling over her barely concealed body. Her hair flowed down around her beautiful face and he once again found his voice catching in his throat whenever he looked at her. It was so odd to meet somebody that you had masturbates to enough to leave cramps in your hand. “Do ya… you, do you what… Do you want something to, ah… to drink?” he stammered. Olivia pulled the teenage, nervous, fidgety, and awkward boy towards her, pressing her slender body against his. “I’d rather dance,” she said with a wicked smirk as she pressed her small chest against him making sure he could feel her hard nipples. Olivia nearly yanked him off his feet as she pulled Doug onto the dance floor, everybody in his class watching them. He had no idea how to dance and just barely swayed on his feet as his stunning date rocked against him. Her hands seemed to travel everywhere at once, sliding over his awkward body while she moved like poetry. Her hips and chest occasionally touched him with an electric jolt as he watched her move, her face serious as she danced against and around him but mostly against him, never missing a chance rub against him. Song after song played and Olivia made sure she and her date, whose name escaped her at the moment, danced for all of them. Her flawless skin glowed in the lights as she put more of a sway into her hips to show off her ass and a shake in her chest to show off her bra-less breasts, her dress always seeming on the verge of showing more than it did. The dumpy high school student had sweat dripping off of his forehead but he didn’t once ask to sit down, all the decisions on what they would do would be her’s and that was all she wanted for the night. She looked around and just as she thought, all eyes were on her and her date, jealous, envious eyes, eyes wishing they were with her instead of with their own dates, A slow song started and Olivia wrapped her arms around her date’s neck and held herself close to him, their bodies pressed tightly together. “Are you having fun?” she whispered into his ear. “Uh huh,” was all Doug could say without risk of a heart attack. Olivia licked the boy’s earlobe before whispering into his ear again as she rubbed against him like a cat. The lights were low and intimate and she took advantage of it. “Then why don’t you wrap your arms around me and hold me closer, this is supposed to be a romantic song.” Doug wrapped his arms around Olivia’s back and she put her head down on his shoulder. “Lower,” Olivia whispered in a low, husky voice as she nuzzled against his neck. Even though the fast song was over, Doug’s heart was pounding in his chest as he lowered his arms a couple of inches. “Lower,” Olivia moaned as she began nibbling the boy’s neck. “What is going on?” Doug wondered as he lowered his arms another couple of inches. “Lower,” Olivia cooed as she forced the boy’s hands down until his hands we’re resting just above the swell of her tight ass. She pressed herself more tightly against him in the middle of the dark gym, surrounded by students and his classmates, her small chest pressed against his so he could feel her hard nipples beneath her flimsy dress and her groin pressed to his so that she could feel the erection in his pants. “That’s all mine,” she thought devilishly as she began rubbing up against the horny high school senior. It wasn’t that he was hung like a porn star or anything, by the size of the lump he would probably be about average, but his erection and the rest of him totally belonged to her. “What Is going on?” Doug thought, on the verge of laughter or tears, he couldn’t decide. Olivia was rubbing her hot, slender body against his and he could feel every inch of her. Her small tits were rubbing up and down his chest, her hard nipples scrapping across his shirt as she kissed, chewed and nibbled his neck. “Seriously, what is going on?” he wondered in a panic as the sexy star practically humped him in the middle of his school. He wasn’t sure but he pretty much was positive that she wasn’t wearing any underwear so that meant his cock was pressed up against her… “Gah…” Doug grunted as he filled his underwear with cum. Olivia giggled as she felt the front of him become wet. “Gotta remember to ask him his name later,” she thought as she looked between their meshed bodies. “Was that for me?” she asked as innocently as possible. “Um… ah… um… sorry…” Doug mumbled unsure if he should step away or not, afraid of showing everybody the wet spot on the front of his pants. Olivia chewed her bottom lip before pressing her willowy body tighter to the boy’s. “I’m flattered,” she whispered breathlessly as she began grinding and rubbing her barely concealed body against the high school student again. “I… I… I don’t… What’s going on?” Doug pleaded, unsure if he was about to cry in confusion or not. All he could do was stand there with his arms at his side as Olivia rubbed against him, his brain feeling as if it was on the verge of simply shutting off. “You just came in your pants over me,” Olivia giggled as she playfully chewed her date’s ear. “This isn’t the first time I’ve made you cum, is it?” “I… I… I… No,” Doug admitted with a sigh if defeat as Olivia continued rubbing up against him. “Do you jack-off to me a lot?” Olivia asked, enjoying teasing the boy. “Yes,” Doug muttered. Olivia pulled herself away from the high schooler and grabbed his hand. “Good. You should. Lets get you cleaned up,” she said brightly as she dragged him off the dance floor. She made sure to pull him past his friends who just stared at them in open mouth shock. If they had seen this happening with anyone other than her they would have thought that their friend was about to get laid but she was Olivia Wilde, famous actress, there was no way their friend was going to score. She smirked knowingly at them before the doors closed behind her, her date’s friends gasped in shock. With one look she had made them unsure what was going to happen between her and their friend and she enjoyed teasing them almost as much as she enjoyed teasing her date. “Where… where are we going,” Doug asked like a confused puppy. “I told you,” Olivia said as they reached the limo and she began nearly forcing her date to get in, “…to get cleaned up.” She closed the door behind them and the driver immediately took off. She snuggled up tightly against the high school student and he just stared back at her blankly. “I know I’m your date and I just made you cum and everything so I’m kinda embarrassed but, I kinda forgot your name,” she giggled. “Well that just tops the night off,” Doug sighed as he rolled his eyes in defeat. He knew there must have been an angle some where in all this surrealism. “It’s Doug.” Olivia cupped Doug’s cheek and used it to draw his face over where she could look into his eyes. “Doug, you need to stop looking so dejected. Yes, I forgot your name. Yes, as you probably guessed I have a ulterior motive to being your date tonight. And yes, I made a mess in your pants but look at it this way, you had the hottest date at your prom even though we were only there for about fifteen minutes. Also, your gonna score tonight.” Doug suddenly choked on his own spit. “Wha…” Olivia pulled away from Doug and pulled out her small purse and began checking her make-up. “You’re about to get laid, Doug. I don’t do anything half-assed. I signed on for the full prom experience and you’re gonna get the full prom experience so stop looking so crestfallen. Oh, I think we’re here,” Olivia said nonchalantly as she clicked her compact shut and the limo pulled to a stop. “I have no idea what’s going on,” Doug mumbled. “Prom,” Olivia said simply before once again cupping Doug’s face and then kissing him deeply. She slid her tongue past his lips and caressed his tongue, thoroughly exploring the insides of his mouth before breaking away and smirking at him. “Next time a girl kisses you, you might wanna kiss her back,” she said with a giggle. Doug didn’t answer, Doug didn’t breath. Doug didn’t move. Doug didn’t blink. Doug just sat like a wide-eyed statue, completely shocked to have just been tongue kissed by Olivia Wilde. Olivia laughed at the look on the kid’s face, “Ha! You should see yourself,” she said as the driver opened the door and she grabbed Doug by his hand. “Let’s go fuck,” she said matter of factly as she struggled to pull her stunned date out of the limo. The world was a blur as Doug was led by Olivia through the hotel, all that he could see clearly was her dragging him by the wrist to the elevator. She wrapped his arm around her slender waist and began nuzzling his neck again until the elevator chimed to a stop and she led him out. When they reached the room she slid her card through the reader and the door opened, snapping him out of his daze. Slightly. “Aren’t I supposed to carry you over the threshold?” Olivia looked up at Doug with confusion on her face before smiling. “That’s what you do on a honeymoon, sweetie,” she giggled as she swung the door open and stepped through. She looked back over her shoulder at him from over her shoulder and saw him staring up and down at the door frame. “It’s not booby-trapped, I promise,” she said as she turned around and winked at him. “And speaking of boobies,” she giggled as she reached up and slowly pulled the straps of her gown down off of her shoulders. Doug could feel his erection roar to life. Olivia was framed perfectly in the doorway, her shoulders bare so that it appeared that her small, firm breasts and hard nipples were the only things keeping her gown up. He couldn’t move. Olivia looked at Doug in complete disbelief. “Doug, I’ve never had to work this hard to get laid since elementary school,” she said with a note of frustration, “So what’s up?” Doug couldn’t speak. Olivia stared up and down at her reluctant date slowly before her eyes opened wide. “Doug, are you a virgin?” Doug couldn’t look at Olivia. Olivia walked slowly over to Doug, swinging her hips enticingly before standing regally in front of him. She raised his chin up with a finger and looked deep into his eyes as she smiled warmly. “Doug, honey, are you a virgin?” After a moment Doug nodded his head curtly. Olivia’s eyes opened wider and her pussy gushed in excitement. “Then this is a first for both of us, Doug. I’ve never had a virgin before,” she said breathlessly before grabbing him by his tie and eagerly yanking him into the dark room. Flicking the lights on she shoved him towards the bed and licked her lips hungrily. He stumbled, almost falling in the bed before regaining his feet and looking back at her. He had a slight look of fear in his eyes at her forceful behavior and that just turned her on more. “Are… Are you… you o.k., ma’am?” he shuddered, his fear doing nothing to diminish his throbbing erection. Olivia’s laughed with delight as she posed herself for her virgin. “I am going to have such fun with you,” she said in a hungry growl as she stalked towards him, barely an arms reach from his trembling body. “I want you to take my gown off, Doug,” she ordered. “I, ah… I, ah… I, ah…” Doug mumbled, his eyes locked onto Olivia’s heaving chest. Reaching out Olivia grabbed Doug’s wrists and yanked his hands up to her small breasts. She released his wrists and his hands just stayed on her chest, trembling and she was pretty sure she could feel his palms sweating through the thin material of her gown. She rolled her eyes and put her fists on her hips and stared at him in frustration. “Doug, this is starting to feel like a rape. Do you wanna fuck me?” she asked flatly. Doug nodded his head dumbly. “I’m gonna have to hear a ‘yes’ or a ‘no’ at this point, Doug,” Olivia said sternly. “Now, do you Doug… um, Doug whose-last-name-I-don’t-remember, want to fuck me?” “Yea… Yes. Yes, ma’am,” Doug mumbled. Olivia smiled sweetly at the young man. “Good. You, Doug whose-last-name-I-can’t-remember, want to fuck me, Olivia Wilde. Verbal contract now entered into the record so get my gown off.” “Dennis,” Doug said as he lightly squeezed Olivia’s small, firm breasts. “What?” Olivia asked, staring at him like he had just drooled. “My… My last name. It’s Dennis,” Doug said as he squeezed and moved Olivia’s tits around in circles. Olivia smiled at Doug’s behavior as he became bolder handling her breasts. He wasn’t handling them in any sort of useful way but at least he was trying now and she didn’t want to break his slowly growing confidence. “It doesn’t really matter at this point,” she said warmly as she gave him a peck on his forehead, “Now get this God damn gown off me so I can fuck you.” Doug smiled in dumb embarrassment as a blush crept across his cheeks as he realized how stupid he was being. One of the hottest women on the planet was practically begging him to get her naked and he was just numbly rolling her tits around on her chest. He slid his still trembling hands up to her shoulders and hooked his thumbs through the flimsy green straps. He slowly pulled the flimsy material off her shoulders and down her arms until gravity took over and her gown fluttered to the floor. Olivia couldn’t help but laugh at the dumbstruck look on Doug’s face as he finally got to see her naked body in the flesh. His eyes darted like they were watching a tennis match between her small, firm tits and her bald glistening pussy. The tent in his pants looked hard enough to be painful but he didn’t move to touch her. He didn’t move at all period. She wasn’t even sure he was breathing. She giggled girlishly before grabbing his wrists again and bringing his hands up to her naked chest. “Touch them. They won’t break,” she whispered. Doug’s hands moved on their own, softly squeezing and caressing Olivia Wilde’s exposed breasts. No, they weren’t just exposed, they were meant to be out in the open for everybody to appreciate. Her nipples were hard and he gently rolled his thumbs across them causing her to gasp slightly which caused a shiver to run through his body. He licked his dry lips and looked expectantly up at her beautify face as she smiled warmly at him. “See, no breakage,” Olivia said and Doug just nodded dumbly at her. “Now what say we start on you,” she said and, without waiting for an answer, began unbuttoning his shirt. He didn’t have what one would call a Hollywood physic, just kinda dumpy and soft but she didn’t pay any mind as she pulled his shirt off his shoulders. His shirt hung on his arms since he apparently was going to refuse to release her breasts which caused her to hide a snort of laughter. Not pressing the issue she began unbuckling his pants and squeaked in surprise as his erection nearly exploded out of the front of his slacks. Olivia appraised the tent poking through Doug’s tighty-whities: not huge by any means but not all that small either. “Like Goldilocks said, just right,” she whispered before kissing him on the forehead which was kind of awkward when he didn’t bend his arms. Being completely naked with the boys hands on her tits, a thought suddenly occurred to her. “You’re eighteen, right?” “Ye… yes, ma… yes, ma’am,” Doug stuttered. “Whew, that’s good. Thought I was committing a felony their for a second,” Olivia said with relief. She grabbed his wrists and began pushing him backwards towards the bed and then down until he was sitting on the edge, his hands still on her tits. She had to use some strength to pull his hands away and stood there looking down at his bulge as she held his arms out. “That looks painful. We should do something about it.” Doug’s eyes fluttered and his vision dimmed as naked Olivia Wilde dropped to her knees between his legs. Before he could stop her, and why did he think he would need to stop her?, she yanked down his underwear and exposed his hard, sticky cock. He chocked on his tongue as she grabbed the base of his prick and flexed her fist as she wiggled her fingers around him his girth. “Trust me, you’re going to enjoy this,” Olivia said with a wink before opening her mouth and sucking in the first few inches of Doug’s prick. She could taste his spilled cum on him and could tell by the way he was throbbing in her mouth that he wouldn’t last long. She braced herself with her hands on his hips as she sucked him completely into her warm, wet mouth, massaging him with her tongue as he groaned above her. She pulled her head back, leaving just the tip of his cock in her mouth, circling his tip with her pink tongue before sucking him back in completely. Repeating herself twice more, Doug exploded in Olivia’s mouth and she expertly swallowed every thick drop. She sucked hard on his shaft as she pulled her head back until he popped out of her mouth. Smiling wickedly up at him she opened her mouth to show him the last of his creamy load before making an exaggerated swallowing motion and then showing him her empty mouth. “How was that?” she asked with a knowing smirk as he stared down at her with reverence. Doug’s cock softened slightly so Olivia wrapped her talented fingers around it and began tugging on it softly. “Lay down,” she said and waited for him to lean down on the bed but, of course, he just sat there like a deer staring into headlights, Once again she thought about how difficult the high school student was making it to get laid so she just shrugged her shoulders and roughly pushed him back onto the bed. Olivia stood up and stared down at Doug staring up at her. “Have you had an aneurysm, Doug?” she asked with her hands on her hips. When he shook his head dumbly she just shrugged her shoulders and said, “Good enough,” as she began climbing up on the bed. “Since you seem a bit overcome I’m gonna make this even easier on you,” she said as she stood up on her knees beside him, “Tongue.” The befuddled teenager slowly stuck his tongue out and Olivia straddled his face. “Lick,” she ordered simply as she lowered her pussy down on his face. Olivia braced her hands against the wall as she rolled her hips against Doug’s face and tongue. She didn’t expect much from the young man and wasn’t disappointed but she was going to get off at least once tonight and she was going to use the high school student to do it. Her clit rubbed against his lips, tongue, and nose as she rode his face, his tongue splitting her pussy-lips and sliding against her wet hole. Even doing most of the work she was feeling her orgasm starting to rise up, nor from any real sexual friction, that was nearly nonexistent, it was the power she held over the schoolboy. As far as he was concerned she was the end-all and be-all of sex, his wildest sexual fantasy come true and it did things to her that no other aphrodisiac could ever do. As Olivia’s warm juices began to slide down his throat Doug realized what was happening. “I’m tongueing Olivia Wilde!” he screamed with joy inside his mind before his mind replied, “You’re not doing anything. You’re just laying there like some kind of asshole while she masturbates with your tongue, diskless.” It was true, he was being a dickless asshole. She had done far more than just throw herself at him and he had acted like a complete pussy. If he was being any more of a pussy he’d a chick and if he was a chick then Olivia was the butch wearing a strap-on. Realizing he was living a dream that he would never ever, ever get a chance to repeat, Doug raised his hands from his side and placed them on Olivia’s wondrous ass, squeezing her soft flesh and holding her down on his face. As she rolled her hips he slid his tongue into her wet, gooey hole, licking her as deeply as he could while her hips continued moving and his tongue slid out of her pussy. He licked her sensitive taint between her pussy and asshole causing her to squeal out as she reversed her roll. His tongue darted back into her pussy as she rolled back until his tongue slid out again and he used it to circle her hard clit. “Oh fuck, Doug, yessss,” Olivia cooed as Doug finally started participating and their encounter and it started to feel less like a passive rape. She slid her hands down and wound her fingers through his hair, holding herself to him as she rode his face and stared down into his eyes. “Yes, Doug, yes. So good, Doug, so good,” she moaned as his tongue slid around her pussy and into her hot hole. His fingers were pressed into her ass flesh, almost kneading her muscles like dough and she was concerned he was going to leave bruises. She was about to say something to the boy but decided that some kind of marker left on her body would just piss her husband off more. “Feels so good, Doug. Your hands feel so good. Squeeze my ass, Doug, squeeze it hard,” she said breathlessly. Doug did as the celebrity instructed, squeezing Olivia’s ass as hard as he could. She cooed and moaned above him as her hips moved faster, grinding down on him and some instinct he had never felt before told him that she was about to cum. With a shuddering lurch she ground her cunt down against him and he opened his mouth and stuck his tongue as far as he could into her pussy. Her juices gushed out into his mouth and he lapped at her pussy as fast as he could, not wanting to miss a single drop. As Olivia came down from her orgasm she collapsed bonelessly on the bed and snuggled up against Doug’s broad chest. She smiled as she looked up at him and he stared back at her like she was some kind of work of art, always to be seen but never to be touched and he had actually been able to touch her. “You sure you’ve never done that before?” she asked and he nodded his head. “Coulda fooled me,” she said as she cuddled against him. It was a complete lie, he was mediocre at best but she imagined most boys were before they got some practice in. Toying with Doug’s still hard cock. “Got to love a teenage boy,” she giggled before looking him deep in his eyes. Cocking an eyebrow she smiled wickedly. “Ready to fuck me?” She laughed out as the schoolboy chocked on his tongue again and began coughing and sputtering. “Don’t worry, it wasn’t really a question.” Moving Doug around like a doll, Olivia got them both ready. She laid down on her back, her slender legs spread wide as he made himself comfortable between her thighs. She reached between their bodies and gingerly gripped his ready cock and positioned it at the entrance to her warm, wet cunt. She pulled him down by his prick until his soft cock-head slid into her slick hole and they both groaned out in pleasure. She rolled her hips up as he slid into her, his hard prick stretching and filling her tight pussy. “Take your time,” Olivia said as she wrapped her arms around Doug’s neck while wrapping her legs around his calves, “Take your time to just enjoy me, Doug.” “Oh geez,” Doug grunted, “Don’t say things like that.” Steadying himself and concentrating on not cumming he thought of whatever he could to not think about sex while he slowly let himself slide into Olivia Wilde’s hot, juicy pussy. He was nearly schizophrenic between not thinking about the feel of Olivia’s pussy, trying to find something else to think about, and not completely believing that he was, in fact, fucking Olivia Wilde. Surreal was not enough of a word. Olivia knew that with Doug being a virgin and with her being, well, her, that he wouldn’t last long and with just a couple of pumps he proved her right. She could feeling him cumming inside of her, and it was a nice feeling. She wasn’t expecting much, a look of perfect contentment sliding across his face before a look of disappointment replaced it. Holding him by his shoulders she smiled warmly up at him. “It’s okay, this was your first time so of course you weren’t going to last long,” she whispered before giving him a quick peck on his lips. Doug stared down into Olivia’s understanding eyes and started to tear up, “But… But I wanted… Y’know, you…” Olivia slid her legs up around the school’s waist and locked her ankles. She could feel him softening inside of her but hadn’t been to worried about that either. “You are such a sweetie,” she grinned before flexing her lower muscles and pulling a groan from Doug’s lips. She used her muscles as she rolled and flexed her hips until he was back to full hardness again before looking back up into his surprised eyes. “But I’m a grown woman and I know how to get mine. Now roll over, it’s my turn to get off.” They re-positioned themselves until Doug was on his back looking up at the naked Olivia. “A girl could get used to you looking at her like this,” she said with a chuckle. “Now you lay right there and let mamma do all the work.” “You… You mean there’s… there’s more?” Doug stammered as Olivia straddled his hips. Olivia smirked down at her boy-toy for the night. “Oh sweetie, you have no idea,” she chuckled as she lightly gripped the base of his hard cock and aimed it up at her wet, dripping pussy. She lowered herself down until his soft tip slipped into her hot cunt before releasing him and bracing herself against the head board with her hands. She lowered her tight cunt down, slowly enveloping the sweet boy’s dick and causing him to moan underneath her, turning her own even more. Slowly her gleaming body swallowed Doug’s prick until he was buried balls deep inside of her and she threw her head back in pleasure at the feel of his stiff cock piercing her as he writhed around in pleasure below her. Releasing the headboard, Olivia grabbed Doug’s wrists and placed his hands on her small tits before grabbing the head of the bed again. His hands automatically latched on to her breasts and she began rolling her hips, grinding her clit against his groin. She giggled and gasped in pleasure as the schoolboy lurched below her and she continued rolling her hips, squeezing his shaft with her lower muscles. She began raising her slender hips up and down, riding him slowly before starting to pick up the pace and all the while Doug stayed still beneath her, letting her use his dick to get herself off. Riding Doug harder and faster, Olivia’s long hair whipped back and forth, sweat flying from her body, her hands holding her up as the headboard banged against the wall, the box springs squealing loudly and the mattress sliding back and forth. Doug grunted with every one of her downward thrusts, their bodies slapping wetly together as Olivia squealed with delight, a maniacal smile on her lips as Doug held onto her wildly wobbling tits for dear life. They grunted in unison as she thrust herself back and forth even faster and harder, her fingernails digging into the soft drywall. “Oh God,” Doug choked as he lurched and came suddenly, erupting inside of Olivia’s wonderful pussy. “Oh God, fuck yea!” Olivia yelled out in joy as she felt her fuck-toy cum inside her. The feel of him spurting inside of her triggered her own orgasm and she fell forward, her slim chest smothering his face. Her body twitched and shook as her orgasm rolled through her, her warm, slick juices gushing around his softening cock. She lay on top of him completely still except for the occasional twitching of her muscles until she rolled over off of him onto the ruined bed. They lay panting together, the covers of the bed completely thrown off, Doug with a completely disbelieving look and Olivia with a completely satisfied smirk, their fingers lightly intertwined. “Good boy, Doug. Good boy,” Olivia giggled. “Thank you, ma’am,” Doug said breathlessly. Olivia looked down at Doug’s soft, completely spent cock. “Looks like the beast has been sated,” she said in a fake, deep tone with an affectionate squeeze of his hand. Doug looked down at himself and then let his head collapse against the bed again, smiling in satisfaction to himself. “I think you may have killed it,” he said with a chuckle. Olivia looked thoughtfully down at Doug’s soft prick. “I hope it’s not completely dead otherwise how are you going to be able to fuck my ass?” she said in a matter of fact tone. Doug choked on his tongue again as his eyes shot open and his soft dick lurched sluggishly. “Wha…” Olivia’s eyes lit up at the look of shock on Doug’s face. She threw what little covers remained up into the air and quickly scurried down the teenager’s body until she was between his legs. She looked up the length of his body and grinned wolfishly up at him before taking his soft cock into her hand and working him slowly. She licked around the tip of his prick before sucking him into her mouth, the taste of his and her own juices making her mouth water as she swallowed him whole. She circled the base of his cock with her pointer finger and thumb and tugged on him as she sucked his soft shaft and massaged it with her tongue. Never losing eye contact with her prom date, Olivia ran her tongue across every bit of his still prick, enjoying the fact that she could easily suck him completely into her mouth. She took a deep breath before drawing him all the way down her throat, swallowing around his tip as she massaged his length with her tongue and tugged on the base of him with her two fingers. All she could hear from him was a soft keening sound like a wounded animal as she continued sucking on him. He slowly started hardening inside her mouth and throat, filling her completely until she was red in the face from lack of oxygen. Just as Doug’s eyes started to cross from the indescribable pleasure Olivia was giving him, she suddenly released him from her mouth with a obscene slurping sound. She never stopped jerking his cock as she sat up on her knees and grinned up at him with a knowing smile. “I… I didn’t think I could, y’know… get hard again,” Doug gasped in amazement. “Sorry, buddy. Your cock belongs to me for the night and it’s not allowed to quit until I’m done with it,” Olivia said matter of factly before releasing Doug’s dick and patting him affectionately on his soft stomach. She excitedly crawled up the bed beside him and then wiggled her tight ass in the air. “Up and attem, Doug. My ass ain’t gonna fuck itself,” she giggled. She couldn’t help but laugh as the schoolboy took one look at her up-thrust rear-end and then quickly clambered to his knees behind her. “Jason is going to be soooo pissed when I tell him,” she thought to herself with another giggle. Olivia turned her head and looked back at Doug from over her shoulder. “Don’t forget to get me wet, sweetie,” she cooed with a wink. Doug held his hands out like a pudgy, horny Jesus, worshiping Olivia’s swaying ass but mostly he didn’t have any idea what to do. He looked up, expecting to see heaven but the only thing above him was the ceiling of the hotel room. He looked down and Olivia’s ass was still there. “It’s a dream,” he thought as he lowered his hands to just a hair’s breath away from the celebrity’s swaying ass, “There’s nothing to be afraid of because none of this is really happening.” Smearing his cock-head with Olivia’s slick juices, Doug began getting himself ready. The physical sensation from rubbing his prick across Olivia Wilde’s pussy and ass felt real but he was oddly detached from what was happening. It, of course, could possibly be real but it felt like it was just another dream and left him feeling confused rather than the extreme nervousness he had been feeling at the start of the evening. He had convinced himself that there was absolutely no way he could be about to fuck Olivia Wilde’s wiggling ass no matter what his body was telling him. It was absurd really, if you though about it. Olivia looked back at Doug from over her shoulder and saw him with his tongue sticking out of his mouth like a child concentrating on a difficult math problem. “You are so fucking adorable, Doug, but I’m ready. How ’bout it?” Doug shrugged his shoulders in a noncommittal way and blandly said, “Sure. Why not?” “Ha! That’s the spirit,” Olivia laughed with another excited wiggle of her ass like a happy puppy about to get a bone. Doug looked absolutely traumatized by the prospect of fucking her ass and for some odd reason it turned her on all the more. She moaned deep and rolled her hips back, sliding the crack of her ass along the length of the shell-shocked teenaged boy’s shaft. “Do it, Doug. Fuck my ass,” she groaned in lust. With his tongue still sticking out of the counter of his mouth, Doug nodded his head quickly and pushed himself forward. The tight ring of muscle resisted him for a moment but then the tip of his prick popped into Olivia’s ass causing her to groan out. In his strangely detached way he saw her grip what was left of the sheets tighter as she began pushing herself back against him. He held onto her hips and the heat coming off of her silky smooth skin made his palms feel like they were touching a hot stove as her ass to slowly swallow his cock. “God yes. God yes, Doug,” Olivia groaned as she continued to push herself back against the high school student’s hard cock. Sweat rolled and dripped down her naked body as she concentrated on the feel of the young prick parting her tightly clutching walls as it slowly filled her. “God yes, God yes, God yes…” she panted like a personal mantra as she continued to slowly spear herself on Doug’s throbbing cock. “It’s not real, it’s not real, it’s not real…” Doug panted like it was his own personal mantra as he continued pushing into Olivia’s hot, tightly clutching hole. Her ass was squeezing him nearly to the point of pain and he knew if he were to admit that this was really happening to him he’d die right then and there. Things like this did not happen to normal people like him, to chubby high school students who were too nervous to even ask a girl to prom. Stuff like this did not happen period. After what felt like hours Olivia’s ass swallowed the last inch of his shaft and she held herself against his hips as she practically growled in pleasure. He had to find out if this was real. “Ma… ma’am, I ho… hope you don’t… don’t get mad at me a… again buy I have to find out,” Doug stammered, “Is this real and if it is why is it happening?” “Ha!” Olivia snorted, Doug’s timing was nothing short of perfect. “Sure, wait until you’re balls deep in a celebrity’s ass before asking what’s going on,” she thought as she looked over her shoulder at Doug. “Yes it’s real, Doug, and I’m doing it to piss off my husband. I just happened to pick you at random. That’s not going to be a problem, is it?” she asked with a goofy grin. In all seriousness, Doug thought over Olivia’s question a moment before shrugging his shoulders. “No?” “Good. Now fuck my ass!” Olivia said through a fit of laughter. A new confidence filled Doug as he held Olivia’s slim hips. He pulled back slowly for an inch before pushing back in just as slowly. He heard her growl as he slid in and out of her tightly clenching ass and felt a strange sense of pride at being the one to have caused her to make that noise, to have been the one to make her feel that good. He pulled himself out a bit farther before pushing back in and a strange smile began to spread across his face as the horny celebrity moaned loudly in pleasure at what he was doing to her. “Do it, Doug, fuck my ass,” Olivia groaned as she held herself still, letting Doug do all the work now. Her hair hung around her face, blocking her view from everything, letting her concentrate on the feel of Doug softly fucking her ass. Slowly Doug began going faster in and out of Olivia’s ass, holding firmly onto her hips. Sweat ran down his body, dripping onto the horny celebrity’s tight ass-cheeks as he fucked into her. She was now moaning constantly, her breath coming in ragged gasps as he went faster and harder into her, her tan ass jiggling slightly with each wet slap of his hips against her flushed skin. He was grunting with each thrust, his balls slapping wetly against her dripping pussy as he barreled into her and she began rocking back against him. “Fuck yeah, Doug, fuck my ass!” Olivia grunted. Her long hair whipped around her head with every one of the schoolboy’s thrusts and her grunts came in unison with his. “Fuck my ass and make me cum! Fuck my slutty little ass!” she gasped out in pleasure. “God I love a cock in my ass, Doug. It feels so fuckin’ good!” Doug’s tongue was lolling out of his mouth as he concentrated on fucking Olivia’s ass and making her cum. Hopefully before he did. He owed it to her for everything she had done for him tonight. He had started out as just a boy but now, thanks to Olivia, he was a man and men took care of their women. He slid one hand under her slender chest to squeeze one of her small breasts while his other hand slid down around her to the wet, sticky juncture between her slender thighs. Her pants and moans had turned to screams and demanding yells, demanding that he make her cum with his cock in her ass. And like a true gentleman he did what he needed to do. Olivia’s senses shattering orgasm overtook her the instant Doug stroked her inflamed clit. “I’m cumming you beautiful, fucking bastard! You’re making me fucking cuuuum!” she shrieked in lust as her entire body shook and thrashed in pure bliss. “Fuck yessss…” Doug grunted as he held Olivia’s sexy, thrashing body to him as he came, filling her tight, clutching ass with his thick, hot cum. He slid his hands underneath her chest and squeezed her small breasts affectionately before sliding them back to her slender hips. As both their bodies began to relax he gave her tight ass a manly slap which made her squeak out in surprise. He chuckled and smoothed her ass before his soft cock popped out of her and a trail of his white load began leaking down over her wet pussy and down her still twitching thighs. Olivia let out a girlish giggle before relaxing onto the bed and rolling over onto her back. Her small breasts gleaned with sweat as she looked up at Doug and smirked up at him. “Wow, Doug, I didn’t know you had it in you,” she chuckled as she held her arms up to him. “It’s my duty to please that booty,” Doug said in a slightly deeper voice before laying down in Olivia’s arms. She snuggled up to his chest and wrapped one of his arms around her, his hand covering one of her small tits. He toyed with her hard nipple as they rested and got there breath back. “Careful there, tough-guy,” Olivia laughed, “It’s starting to sound like you watch too much porn or something,” “I never know the cool thing to say,” Doug admitted, “Mostly I just stutter and blush in embarrassment.” Olivia looked over her shoulder up at Doug and used her hand to pull his face towards her. “Don’t worry about it to much, tough-guy. Once women find out the kind of things you just did to me, they won’t be too interested in conversation,” she said before kissing him deeply. As they broke the kiss, Doug looked deep into Olivia’s eyes. “We’ll just add that to my Tinder profile then,” he said with a chuckle. “You really seemed to enjoy yourself there,” he added with a cute blush. “Oh yeah. Anal’s my favorite,” she admitted unabashedly, “Especially since I usually only let Jason do it on special occasions. I wanna keep it special.” “What’d your husband do that made you pissed off enough to accept my invitation, anyway? Also, do other things,” Doug asked. “He’s a no good lying betrayer is what!” Olivia snapped before calming herself. “Anyways, I’m too tired to bitch about Jason. Let’s get some sleep before I have to leave,” she said before snuggling her naked body fully against Doug’s, wiggling her sticky ass affectionately against his soft cock. —– Olivia strolled into her house at close to noon the next day and let herself in through the back door. “Jason, I’m home,” she called out. Jason poked his head in from around the corner to the living and started, “It’s about time! What prom lasts….” before stopping and noticing his wife. Her dress was wrinkled and stained in a few places, her make-up was smeared, and her hair disheveled. “Did you get mugged?” Olivia smirked wickedly at her husband and then strolled past him to their bedroom. “Nope. Just had a really good, fulfilling time at prom.” “Why are you so late?” Jason asked as Olivia slipped into their bedroom and he began to follow. “You know teenaged boys. Such stamina,” Olivia chuckled as Jason stepped into the bedroom. Jason stared in disbelief at his wife as she slipped out if her dress. “Wait, are you saying you fucked him? Why… why… What would make you do that?” he stammered. Completely naked, her hair wildly messy, her make-up smeared, and her hands on her slender hips, Olivia glared at her husband. “Because you lied to me, Jason! You practically betrayed our marriage vows! So that’s what you get for lying to me about taking the garbage out! Jason stared dumbfounded at his naked wife. “Fuckin’ actresses,” he muttered in disbelief. The End.
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