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Thread: The Adventures of a Pool Boy with Olivia Wilde

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    fanfiction The Adventures of a Pool Boy with Olivia Wilde

    The Adventures of a Pool Boy
    With Olivia Wilde
    Written by aries1000
    Codes: M/F, oral
    Disclaimer: This FICTIONAL story contains graphic sexual situations, if you are under age or easily offended STOP READING!



    It was another perfectly sunny day in Venice, California as he loaded up his car. Having lived here for a month, the only job he managed to find was working for a popular pool service company where he fixed filters, tested chlorine levels, and cleaned absurdly rich people's pools. A far cry from what the main goal was, one that was shared by most of the population that moved to California from out of state. To be an actor, that was the end game.

    The perks of the job were nice. He was always outside, managed to keep a nice tan, and most of the clients offered him food and tipped generously. There was a good deal of travel involved, and his PT Cruiser, although gas friendly, wasn't going to impress anyone on the boardwalk.

    After grabbing his itinerary for the day and lunch, he put the keys in the ignition and eyed the first stop. An issue with a waterfall that was supposed to cascade into a newly built in-ground pool, located somewhere on Venice boulevard. The address was surprisingly familiar because he had seen it a handful of times when picking his jobs, and avoided doing so since it was a bit farther away from his usual appointments. Rich people and their toys, he thought to himself.

    Even though traffic was pretty heavy, driving in weather like this always made him smile. 85 degrees and sunny with no humidity, which when compared to his hometown in Chicago, made him laugh. The drive across country was worth it for the weather alone.

    He pulled up to his destination to find a gate was blocking the entrance to a driveway, and was monitored by two guards, one who approached his car.

    "Can I help you?" asked the guard?

    "Yes, uh, I am here to fix the pump for the waterfall above the pool. I'm from Sardelli Pools, and I was told to stop by at 11 am" he said.

    The guard walked back to his station and made a phone call. After a minute he waved and the gate opened. The driveway was incredibly long, it took about 20 seconds to approach what looked like the biggest house he'd ever seen.

    "Holy shit", he whispered.

    It was like looking at the Bellagio in Las Vegas, a mega mansion on steroids. There were a few people tending to the lawn, which was as big as a football field. He parked his car near a garage that had 8 doors, one of which was open and sported two exotic sports cars he didn't recognize. He was in a bit of shock and awe upon exiting his car, taking in the scope of just how large this house was. One thing that caught his eye though was there seemed to be a handful of security guards roaming the grounds. They wore the same uniform the guards had on near the gate entrance.

    He grabbed a box of tools, some supplies and started walking towards the front of the mansion. A guard quickly noticed him and walked alongside him, guiding them both up to a large red door, which opened upon arrival. He was taken aback by the size of the man waiting in the doorway, a monstrosity who looked like he hate barbells and probably hadn't laughed in his entire life based off how serious he looked.

    "Follow me, and I'll show you where the pool is" growled the scary guard.

    Walking quickly through another set of doors, a thought left his lips before he could stop himself.

    "Who lives here, a prince?" he said.

    The scary guard growled, "This is the Ruspoli residence, and yes that is of prince descent. But that's none of your fucking business".

    The walking halted and the guard pointed at the pool which was now in view from where they were standing. He quickly made his way out onto the patio, hands trembling a bit at the exchange with the frightening guard. But that immediately left his mind as he gazed at this pool, which was a poor word for what he saw.

    It was like looking at an L shaped wave pool, the kind he used to go to as a kid at the water park. Only this pool was decorated with palm trees, two bars located at the corner of the L, one of which was a swim up bar. A 10 foot sputtering waterfall ran along one side, next to an assortment of patio tables and chairs. He went to investigate the waterfall and noticed a switch panel right underneath about a foot beneath the pool's surface.

    He took his shirt off and sandals and jumped in. The water was refreshing and he went under and flipped the switch and of course, the waterfall came to life, crashing down into the water with a thunderous sound. He shook his head and smiled as he exited the pool.

    "What are you smiling about?" asked a sexy voice behind him.

    Startled, he turned around and his jaw dropped. Her cat-like eyes, her perfect cheekbones and soft lips; his brain seemed to freeze as he stood there transfixed at this Helen of Troy. Meeting Olivia Wilde was something he had fantasized about for years and here she stood only a few feet away, wearing a pink silk robe and sandals, with her long hair cascading around her shoulders.

    "Nothing" he stammered.

    Taking a breath and finally looking away, "Well, I just thought it was sort of funny that not all of the switches had been flipped."

    He quickly added, "It happens all the time" knowing that last part was a lie.

    Wearing only a bathing suit, he became a bit self conscious as he stood there dripping, even though he worked out daily which made friends jealous of his wonderful definition, especially his abs. Still, standing next to Olivia Wilde, made his temperature rise and made him feel rather nervous.

    Olivia stared him down, and he noticed her eyes travel up and down his body.

    "Yeah, well we had this party... and... maybe someone bumped up against the switch. It's a pretty poor spot for something like that " she replied.

    "The guard said something about this being the estate of a prince. Is that true? Why are there so many guards, they are everywhere? " he asked.

    She smiled and walked a bit closer to him.

    "Yes, I am married to the son of a prince, and he is extremely protective of this house as well as me. He does overdo it with all these guards, it is such a waste of money." Olivia responded while playing with the tie to her robe.

    He felt a lump appear in his throat.

    "You mean, they spy on you?" he asked as he took a few steps towards the pool, mainly to create some distance between where they stood.

    "Well, not really. Birk does from time to time, but the rest leave me alone " she answered.

    "I take it that Birk is the frightening Buzz Lightyear looking fellow, except he's on steroids and has a voice deeper than Barry White " he said.

    Olivia laughed, "Yeah, that's him. And if you are wondering, he really doesn't smile."

    He laughed and turned around to grab his clothes, and after a few double takes...

    "Uh, your shirt and shoes are in the water " Olivia said as she pointed to the middle of the pool where the shirt was floating on top of the surface.

    "What the hell" he blurted out and jumped in to grab his belongings.

    As he exited, again, Olivia suggested "I can throw those in the dryer if you want, so you aren't all…wet. The guest house is right over here."

    She stared at him smiling.

    "Umm… sure, I guess?" as he scratched his head, and he started to follow behind her as she walked to the guest house.

    It was hard not to stare at her, as her bathrobe came down to only her upper thigh, he felt his penis stiffen a little. He nervously looked around for a guard as they approached the guest house. His friends wouldn't believe this, and even though he truly felt scared when thinking about Birk, at this point he just wanted to get out of here. But the presence of Olivia Wilde was intoxicating and was clouding his judgment. He wished he was in his car.

    Upon entering the guest house, it was much cooler, and he followed her into the laundry room where she handed him a bath towel off a shelf.

    "Here, give me your shorts and I can throw them in the dryer with your shoes and shirt and it should be dry in a bit" Being taken aback by this suggestion, he carefully tied the towel around his waist and pulled off his shorts.

    She stood there, watching with her sexy smile, and tossed his clothes into the dryer.

    "Would you like something to drink while we wait?" she asked.

    "Sure" he replied, and he followed her to a large living room, lavishly decorated with black leather couches and a beautiful large window with stained glass.

    He peered out at the yard, and could make out a few guards still at their patrol, this window did very little to obscure the view. His hand gripped his towel tightly, in effort to prevent it from slipping off. As she made him a martini, she noticed him peering out the window a few times.

    "Aren't you wound up tight? " she said coyly. "Here, this should help you relax a bit. It's a specialty of mine, tastes like a Long Island, but with a bigger kick".

    Taking the drink, they both sat down on the couch, and he took a long sip and closed his eyes and smiled.

    "Wow, this is actually really good" he said.

    They made small talk for about 10 minutes about their favorite drinks and he explained how he had recently moved here.

    Finishing the drinks and feeling much more relaxed, he looked at the clock and said, "I think my clothes will be fine by now."

    Coming back from the kitchen with another round she replied, "Probably in another 15 or so. It will take a bit longer because of your shoes."

    He seemed to accept this and sat back on the couch with his drink in hand. Olivia sat down next him, with her legs up on the couch, making her robe rise slightly higher, which in turn caused him to stare at her incredibly sexy legs.

    Catching her glance, he felt a bit embarrassed and his cheeks grew red. "Sorry, I didn't mean to stare"

    "You have nothing to be sorry about" as Olivia laughed, and lightly dragged a fingernail over his defined shoulders and buff chest.

    "It's not like I haven't been admiring you this entire time."

    The sensation caused his cock to stiffen.

    "Actually, I have a confession to make. I sort of have a crush on you.

    Confused he replied, "What are you talking about? I think I would have remembered if we met before. And I don't really count watching episodes of House or The O.C as meeting."

    "Oh, so you know who I am," smiling and showing off her perfect teeth.

    "Well, actually, a few weeks ago I was over a friend's for lunch, and you happened to show up. She was going on and on about this gorgeous pool boy, and so I took a peek out the window and saw you installing a diving board. I asked her what company you worked for, and have been trying to get you to come here for over two weeks, but they kept sending other people."

    Laughing, "They probably thing I'm an idiot since I've been just turning the switch off every time."

    Olivia took a sip from her drink, and stared hungrily at him.

    "So yeah, I couldn't get you out of my head."

    Her fingers started feel his bicep, "I mean, just look at you".

    He tried to cover his growing hard on with his hand.

    Stunned, but smiling, he turned towards her on the couch so they were a bit closer.

    He stammered, "Wha-, uh, I really don't know what to say."

    He laughed nervously.

    He could feel his cheeks warm up a bit from her presence and a mix of the alcohol. Looking directly into her eyes, "Man, I've fantasized about you since the first time I saw you".

    Hearing his own words, he quickly added, "I don't mean that, I mean. Shoot. I can't believe I told you that".

    Olivia moved a bit closer to him, he could feel her breath on his face.

    "Well then, that makes two of us."

    Her eyes traveling down to the tented towel, and back up to his face, Olivia sexily whispered into his ear "I actually masturbated thinking about you the other day."

    She ran her soft and luscious bottom lip over the top of his ear.

    He gasped, and before he could respond, she whispered, "Have you ever jerked off thinking about me?" and she began to slowly jerk his cock over the towel, which led to his involuntary moan.

    His heart was now racing, as Olivia was now inches from his face. He was intoxicated by her beauty.

    Struggling to get out the words, he asked, "What.. about.. your husba-, but was stopped short as Olivia quickly darted in and gave him a long passionate kiss, their tongues dancing.

    Her tongue felt wonderful in his mouth, and she swung her leg over him so she was now straddling him on the couch. She began to grind on his cock, as his hands started to work up her legs, using his thumbs to rub inside her creamy taut thighs. This caused her to gasp as she broke up their kiss by gently biting his lips. He moved to her neck, dragging his teeth and gently sucking.

    She leaned back on her knees to quickly untie her robe, aided by his willing hands. Removing the robe, Olivia was naked underneath, her perfectly perky breasts sticking out at him. He eyed her tone and petite waist and beautifully manicured bald pussy, before she straddled him again. As they shared another passionate kiss, his hands began to work her breasts, gently pulling at her rock hard nipples, and she grabbed his curly hair to guide his mouth over her tits, which were aching for some more attention.

    He worked the underside of her breasts with his tongue, gently pulling at her nipple with his fingers, working his tongue in circles until gently using his teeth on her nipple, which made Olivia give an orgasmic moan. He repeated this on the other side, but this time sucked violently directly on her tit, which caused her nails to dig in a little on his back.

    "Fuck, that feels good" she said huskily.

    He grabbed both of her legs and turned which made Olivia lie directly on her back on the couch. As he leaned over her gently biting her top lip, his knees prevented him from lying directly on top. Olivia used this moment to remove his towel, which caused his massive cock to stick straight up, grazing her stomach. She grabbed it with both hands and using the palm of one hand worked the tip of his penis. She squeezed the base of his shaft super tight while she continually rubbed her palm on his bulging head.

    "Oh my god" he panted, as he kissed her.

    She continued to work his penis, tugging at his balls with one hand and his stroking his shaft with the other. The pleasure was overwhelming and caused his knees to buckle, so he was lying directly on top of her, which put her in the perfect missionary position.

    She still had a hand on his massive cock and begged, "Please, fuck me," sucking his earlobe.

    Loving the power he now had, he grabbed both of her hands and firmly pressed them against the couch above her head.

    "Not yet", as he kissed he neck working down to her perky breasts, biting and pinching them which caused her thighs to tighten around him.

    He place his hands on her hips, feeling her smooth skin, kissing her belly button and dragging his teeth up and down her incredibly toned stomach. Olivia moaned loudly, as he worked his tongue right above her pussy, dancing on her clit with his tongue, and around her lips, biting at her inner thigh. He could see she was extremely wet, and drawing this out was making her go crazy. As he entered her with his tongue, her thighs gripped his head tight, and he balanced this out by rubbing her inner thighs with his finger and thumb as he drew patterns on her throbbing clit, his tongue darting in and out.

    "Fuck, right there, oh my-" Olivia said as he built up a rhythm.

    He was enjoying every second of this, and her continual euphoric whimpers meant she felt the same way. Using two and then three fingers, he entered her wet pussy, her lips gripping his fingers rather tightly, as he sucked on her clit. She dug her hands right on top of his head, pushing him in even further to her needy pussy, arching her back and biting a nearby pillow to keep from screaming. His hands quickly moved up to her perfect breasts, rubbing and grabbing her hard nipples as he worked her aching clit with his tongue.

    She was close to climaxing, as he heard her quick pants of breath. Olivia arched her back and violently squeezed his head with her thighs as the orgasmic waves permeated through her body, leaving her momentarily silent as her juices flowed directly onto his face. Her stomach and thighs quivered as he enthusiastically lapped every drop up, kissing her thighs, and dragging his tongue over her now sensitive lips and clit. Lifting his head up, he leaned up and gave her a deep and long kiss.

    "You taste like peaches," Olivia blushed at this, and was still out of breath from her epic orgasm.

    She grabbed his pectorals with both of her hands and pushed him on his side so she could get on top. With his back to the couch, and her pussy resting on his shaft, she arched her eyebrows and said "My turn".

    She slowly worked her large tongue down his chest, kissing and biting him, and working her hands over his defined abs and chest. He could feel her nipples were still hard and the sensation he got from her rubbing them on his stomach make his cock ache even more. She kissed him slowly, biting his hips and licking both of his inner thighs, his cock was rock hard and felt it graze against her cheek. Olivia was eager to return the favor.

    She squeezed the base of his cock, and gently worked the tip with her tongue, staring up at him and loving how she could make him moan, in total control with his manhood in her hands. Slowly sucking just on the tip, she worked her hand up and down his shaft, pumping him into her mouth, working his cock deeper and deeper with her mouth. When his cock was halfway down her throat, he could hear the throating sound, as he lifted his butt of the coach to eagerly aid this process.

    Olivia went down as far as she could, gagging on of his rock hard member, before quickly taking it out, and continually jerking his now slick cock. Jerking it quickly and staring right at him with her beautiful eyes, he moaned with pleasure, as she let her saliva drip out of her mouth on the tip of his penis. She deep throated him again and again, with him pumping into her willing mouth. She finally was able to swallow his entire gorged penis, making her eyes water a bit.

    This really turned Olivia on, as she began to finger herself from behind. Once he saw this he pulled her up, and as they kissed, she took control. Sitting back up she took his hard dick and began riding it, causing both of them to moan with pleasure. It felt so incredibly tight he had to concentrate so he wouldn't blow his load early, even grimacing with pleasure as she bounced up and down on his cock.

    His hands worked her perky tits again, working her breasts and violently pulling her nipples, which she loved. She took two of his fingers in her mouth, biting and sucking them and she continued to ride his cock, which repeatedly went balls deep into her super tight pussy. She took both of her hands and placed them behind her, directly on his legs to give her more support to grind hard and fast on his cock. He grabbed thighs and was working up a sweat as he furiously aided in pounding her pussy.

    "Oh... god... Rub my clit." Olivia begged, gasping for breaths.

    He smacked her clit, rubbing it, knowing she was near another orgasm. This time however, he pulled out, and as she leaned forward in protest, taking her hands off his legs, he twisted around so she was face down on the couch, getting behind her on his knees. She knew exactly what he wanted, and she wanted to get off badly. On all fours, she raised her absolutely perfect ass, so her lips were on full display. Spreading her legs a bit, he grabbed her slender waist, and entered her from behind, her tight pussy incredibly wet as she clamped down on his cock as he pumped into her.

    Squeezing her ass with his hands, Olivia loved every second, grunting as she worked hard to grind strong and fast. The only sound audible in the guest house was orgasmic moans and the force of him slapping against her. Reaching for her hair, he pulled her back, and Olivia bit her lip, loving a little bit of pain and pleasure as he ravaged her again and again.

    "Slap my ass" she demanded, in her sexy husky voice.

    His hands left her hair and he gave her a hard slap on the right cheek, as she let you a loud yelp. As a natural reaction to this, he pushed her head down into the pillow, and violently continued to slam her, as Olivia's knees began to weaken because of the impending climax. She bit the pillow again to keep from screaming. Turning her head round to look at him pumping at her, she took one of her hands to touch his rippling abs and he quickly grabbed it, and Olivia offered her other arm as well.

    Picking up speed, as his massive cock slammed into her ultra tight pussy, her legs spread as he grabbed both of her hands so they were behind her back, she burst out "Oh god, I'm gonna cum!" and let go of his hands, crashing into the pillows with her ass still raised.

    He continued to pump into her as her knees buckled, whimpering in euphoric pleasure, toes curled, he could feel her juices flow down his shaft and onto his balls. Olivia was gasping, feeling his rippled sweaty body on top of her, quickly breathing, overwhelmed by another powerful orgasm, as he pulled out still rock hard, her juices dripping from his perfect cock onto her ass. She turned over, as beads of sweat dressed both of their wonderful bodies. Turning over and looking up at him.

    "My god that was fucking incredible." Her toned stomach quivered a bit as she closed her eyes for a second.

    Looking up at him again and eying his still rock hard cock, she lept up from the couch pushing him back against the wall so they both were standing near the couch. Immediately getting on both knees, she looked up at him with her sexy cat-like eyes and huskily said "I am going to swallow every drop."

    She took her dainty hands and began pulling on his balls pressing his shaft against his stomach and using her mouth she engulfed his balls, pressing her tongue against them. Licking his balls she playfully used her teeth to pull at them, the sensation causing him to gasp and moan. Woring her tongue up to the shaft, she again being working on the tip of his penis with her mouth sucking fiercely and hollowing her cheeks in doing so.

    Olivia could feel his cock tightening up and knew he was close. She violently began to jerk him off, using her other hand to smack his cock. She looked up at him with her sexy smile as she smacked his cock and his stomach tightened from each hit, knowing they both loved this.

    He loved the sensation, looking down at this gorgeous woman, who expertly worked his cock with her hands and tongue. He could feel he was extremely close, the orgasm began building. Olivia sensed this and with one hand tugged his balls and the other worked his slick rock hard member. She stuck her tongue out so was working his balls, shaft, and the tip of his penis all simultaneously, the sensation of her tongue on the tip of his cock was going to push him over the edge. Looking directly into her mesmerizing eyes, as she stared intently back up at him, working his cock and loving every second moaning with pleasure, he could no longer hold back.

    A volcanic eruption of semen shot out at hit her upper lip. He tried to continue staring into her eyes, as this enhanced the orgasm, but the waves of pleasure were so strong, it forced his eyes to scrunch up as she continued to pump out semen from his aching cock. Another stream of cum hit her right cheek, and she moved in on his cock, pumping vigorously with both of her hands.

    Worried he might collapse if his knees buckled, he grabbed the nearby door for support, as he let out some loud grunts and groans, overwhelmed by this heavenly feeling. Olivia continued to work every last drop of his cum into her mouth and before she let go she used her teeth to gently graze his penis, causing him to shudder and quiver.

    She stood up, and wiped the cum from her face with her hand and slowly sucked it off her fingers. He sat there in awe at this gorgeous vixen. They looked at each other, both sweaty and flushed from great sex.

    She smiled at him and said, "I have a feeling my pool might need some repair next weekend."

    He smiled, but before he could answer, a knock was heard at the door.

    "Mrs. Wilde, have you seen that pool kid. The waterfall is on, but his car is still here?" asked a deep and unpleasant voice.

    Panic stricken, he grabbed his clothes, threw them on as Olivia told him to go out the back. Before sneaking out, Olivia grabbed him and told him to walk around the fence, where the showers were by the pool. Looking at her perfect naked body one last time, he exited the window and headed around the fence.

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    TPG's Avatar
    TPG is offline Fate whispers to the warrior,
    "You can not withstand the storm."
    The warrior whispers back,
    "I am the storm."
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    very nice Olivia Wilde story. thanks aries1000 :gold:

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    Thanks!

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    Very well done. Great read. Definitely look forward to anything else you may write.

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