Summer job leads to an encounter with Olivia Wilde

Summer job leads to an encounter with Olivia WildeMy name is Troy Burns and I'm the guy who flies under the radar, all through school I had only a few friends, but I mostly chose to be a loner on my own. Most of the troublesome things that some of my peers were getting into never interested me. I recently graduated three months ago and decided to get a summer job to help out my mom who's a single parent. I knew she needed the extra help and now that I was finished with school I had the extra time to do just that.Of course, I didn't tell my mom that it was the reason why, because I knew she would try to stop me. After a month of searching, I finally found a summer job where they were willing to hire me. It was a popular summer vacation spot in a suburban area, where a lot of tourists would come and stay for the summer. The resort is called "Stay Away", which basically means you get a vacation from the stresses in your life. Well that's what the website said anyway.Most of the tourists would stay at the resort during the summer for one reason or another, and during this time the resort always had a celebrity or celebrities come and stay for a few weeks or sometimes the entire summer. I would be lying if I said this wasn't a big reason why I kept applying for this job more so than others. In my favor, they were short on staff for this part of the year so I was able to just about wiggle my way in.I started my training a few weeks ago and today was my first day on the job. The work required was to basically attend to the guests needs and wants. The list of celebrities booking in at our hotel are always growing as the manager informed us, but so far the only celebrity that was current checked into the resort was Olivia Wilde. Having Miss Wilde as one of the guests that I had to attend too didn't hurt, especially since I've fantasized and jerked off to her many times before.My mom gave me a ride to the resort and gave me her best regards for my first day. Both staff groups had a staff meeting with the manager of the resort, so he laid out for us what each job we would be doing, and what the optional activities for the guest would be done today. After what felt like hours, the meeting was finally over and the two groups went their separate ways.The day was going by pretty slow for me, and while my my co-workers were busy with various guests, I had little to do since me being the new guy in the job. The other staff members most often would take over without giving me a chance. I didn't even get a chance to meet Olivia Wilde yet as she mostly kept to herself today, much to my dismay. As time passed by it was almost time for the day staff to go and the night staff to takeover. I decided that before I left for the day that I should at least go to the Olivia's vacation house on the resort and introduce myself. This was because she was the only guest I hadn't seen, whilst watching another staff member help out a guest or passing by in the lobby. After all, that would be the proper thing to do and would most likely give a good first impression.The resort had a design for the guest where they each had their own house on the property broke off into sections. The houses were spaced out to a point where each guest had their privacy, that's how big the resort was! As I made my rounds I stopped by Olivia Wilde's vacation house. On my way in, her fiancée was just leaving with their c***d and I had a little chat with him as I introduced myself. He let me in as they left so I could check if Olivia needed anything. Apparently, he was taking their baby son out to one of the events happening for c***dren on the resort, but Olivia was staying behind to read a script for a role she was interested in."Ms. Wilde?" I call out, walking around the home. Olivia was nowhere to be seen and the house was that quiet, you could hear a pin drop. This was strange because I knew she was home. As I walked past a stairway leading to the downstairs area, I heard a door close. I did a double take, the house was once again filled with silence. I went down the stairs which lead to a sauna room."Ms. Wilde, are you down here?" I called out once again. I looked at the sauna room and the windows were foggy from the heat. I walked over to the right side of the sauna room where one of the windows was only half fogged. I wanted to check to see if Olivia was in their or not. As I peeked in through the half fogged window, my eyes widened when I saw Olivia Wilde sitting down on the bench laying back, fully naked with her eyes closed.My eyes were glued to the hot brunette, unable to look away. I felt my uniform pants suddenly get uncomfortable as before I could realize, my cock was getting hard from seeing the sexy Olivia Wilde naked. My mind was racing with the sight of a nude Olivia Wilde before me. Olivia opened her eyes and looked right in my direction. But I was too caught up in the moment to try and hide. Olivia eyes were affixed on mine as she saw me through the window of the door. With that, I figured I was busted and will most likely be in big trouble. I panicked, not knowing what to do when the shock factor leaves Olivia's face and she motions for me to come in.I stare at her dumbfounded, did she really just invite me to come in? I thought she would storm out of the sauna and tell me off and then report me. Olivia once again motions for me to come into the sauna and I slowly, but surely open the door. Some of the steam escapes the sauna as I opened the door and take a few steps in."I'm...I'm so sorry. I wasn't peeking on you or nothing like that. I was just...", I stammered, my words all over the place."Relax," Olivia says with ease.Olivia sat there on the bench naked, not even trying to cover herself up with a towel, and I'm trying my best to look her in the eyes and not let my eyes wander over her sexy naked body."You work here right?" she asks.I nod."Yes, Ms. Wilde. I'm Troy Burns and you are one of the celebrities that I was assigned too. Once again I'm so sorry for what just happened. I wanted to introduce myself and just stumbled upon you down here..." I said nervously.I was telling the truth, but it was also a half lie because once I found her in the sauna naked, I didn't exactly look away. By the look on Olivia's face I got the feeling that she knew that I wasn't telling the whole truth."You're nervous, it's cute," she says with a slight smirk.I gulp nervously. I was at a loss of words."I honestly had no idea you were in here...naked. I was told you were reading a script.""Oh I was, but I needed to take a little break to relax," she said, as she crossed her legs, hiding her pussy.My erection was not going anywhere anytime soon, especially when I got the feeling Olivia took a quick glance at my crotch."Anyway I should go. Sorry to disturb you," I said nervously.I turn around to leave, "Wait a minute," she said, stopping me.I slowly turn around, raising an eyebrow."Close the door. You're letting the heat escape," she said.I hesitate, surprised by this. I closed the door to the sauna and the heat starts building up more."Tell me something Troy...what do you think about me?" she asked."I um...well I think you're a very talented actress Ms. Wilde," I say, giving a standard reply which I thought would fit, hoping that she wouldn't notice my erection."Cut all that crap," she said, catching me off guard."Excuse me?" I said, trying to play dumb."I mean what do you think about me? Right now naked in front of you," she said, tilting her head to the side.My eyes widen in shock."Ms. Wilde...""Don't be shy. You weren't shy when you were peeking in on me."I was speechless, I had no comeback or an excuse. I was too shocked to do anything, but stand here and stare at Olivia."Do you want to fuck me Troy?" She said with a growing smirk."I think it's time that I leave you be..." I said before getting cut off."Answer me. Do you want to fuck me?" she continued to press me.I was getting pushed into a corner and didn't really know what to do from here. Do I answer her question or just leave? And what if I did just leave and she then reported me?"No," I lie, with not much conviction."Really? You say one thing, but that bulge in your pants is saying another," she said, giving me a full on smirk now.I was busted. She saw my erection and no longer able to hide it. Seeing the sexy MILF Olivia Wilde naked and referring to my stuff cock had gotten me the hardest I've ever been."I'm so sorry Ms. Wilde, I..." I stumble over my words."Don't apologize...I consider myself a good and caring person Troy and it would be cruel of me to leave you like that now wouldn't it?" she continued.I nod. I instantly regret it, with Olivia being naked and the way she was talking, I had gotten caught up in the heat of the moment. Olivia seemed to be pleased with me agreeing with her.Olivia grabbed a small bottle of lotion and stood up. She walked up to me and pressed herself against my body. I stood there as felt her small soft breasts and hard nipples pressed against my chest."What about your fiancée?" I asked."What about him?" Olivia replied, giving a nonchalant shrug.She reached down and started rubbing my hard cock through my uniform pants."Ahhh..." I moaned."You like it when I rub your hard cock?" she cooed."Oh yeah Olivia, that feels so good," I respond. As much of a fight that I was putting up before was now lost as I finally gave in. Olivia slowly unzipped my pants, teasing me some more. She pulled down my uniform pants and then my underwear, my hard cock popping free like a sword. Olivia squeezed out a glop of lotion into her palm and started stroking my hard cock again, letting the bottle of lotion drop to the floor. The way she touched me was a whole new sensation as she was actually fondling my cock this time without the restraints."Now we don't have a lot of time. So let's get this going," she said as she started stroking increasing faster.It felt so good. The way she jerked my cock, trying to get me off. Whilst she stroked my throbbing dick in her soft warm hand, the luscious MILF leaned in close, whispering in my ear, "You wanna cum for me?" "Ahhh yeah...in a little bit."Olivia began jerking off my cock quicker, trying to get me to cum. It started to feel like a competition of how long I could last against her attempts to make me spurt. Her hand felt like butter as she was gave me an incredible handjob. She reached down with her other hand and started playing my sensitive balls. At that point I thought that right then and there I would explode in her soft hand. But then she stopped all of a sudden, much to my dismay."What's wrong?""I think we should have a little more fun," Olivia said in a sultry voice.Olivia leaned in and kissed me deeply, pushing her tongue into my mouth as the sauna got hotter, her sexy tight body glistening. I broke the kiss reluctantly and looked her up and down, checking out her incredible body up close. I couldn't believe this was actually happening, Olivia Wilde a women I jerked off too time and time again was naked in front of me."Tick tock. You ready for some more fun?" she sarcastically asked, kneeling down in front of me and taking my cock again back in her hand. She cradled my balls in her other hand, soon stroking my cock back to maximum hardness."It turned me on so much to know that you were watching me, getting horny. I bet you just can't wait for me to suck your hard cock? You want your cock in my hot, wet mouth?""Ahhhh, of fuck yes!" I groan loudly.Olivia was right and she knew it. This had only been a fantasy of mine while I was jerking of too her, but now it was really happening. The hot MILF opened her mouth wide as I stuffed my hard cock deep inside her warm wet mouth, her soft red lipstick coated lips sliding back and forth on my throbbing cock. The sight was unbelievable as the sexy actress looked up at me with her sexy eyes whilst taking my cock repeatedly into her hot mouth.Olivia stroked my throbbing hard shaft as she continued to suck on the spongy head, teasing me with her exquisite tongue. She began working my penis harder now, trying to bring me to the edge like she wanted to win this competition, one I was definitely losing. I grabbed two handfuls of her hair in both my hands and started fucking her warm wet mouth.I felt like I was about to explode when all of a sudden she took me out of her mouth, and started to jerk me off again."Cum in my hot mouth. I want you to blow your load down my slutty throat!" Olivia moaned, as she was egging me on to cum."Ugh, oh fuck," I grunted, my warm semen shooting out and splattering down into her throat, filling Olivia Wilde's warm satisfied mouth.A pool of my cum settled upon her tongue with some flowing back, sliding down her throat. I continued to cum hard and panting as the sauna got hotter. I was cumming like I had never done before, and my eyes clenched shut as the sensation took over me.As I finished cumming in Olivia's mouth, she swallowed it all, doing it like she was a pro."I win," she said, with a sexy smirk."That was so good..." I managed to say, overcome by such a huge orgasm.Olivia looked up at me with her sexy smile. I still couldn't believe that this just happened and it was amazing. Who would've thought an 18 year old loner would get a handjob and blowjob from Olivia Wilde? One thing was for certain...this was going to be a summer like no other.It's been a week since my unbelievable encounter with Olivia Wilde, and I'd be lying if I said I hadn't been thinking about it everyday since. As much as I was hoping for a chance to actually fuck her, Olivia had already left the resort with her family a few days after. I didn't get the chance to see her after that evening either. However, to my surprise, she left a good appraisal for me to my manager which didn't hurt. In fact, it helped me be able to attend to other guests besides just watching others do so.Since Olivia, there had been no celebrities staying at the resort in the past week or so, but that was all about to change as me and the other staff were informed that another celebrity had just made a reservation. And that celebrity happened to be Kaley Cuoco. We were informed about this a few days ago today was the day that Kaley had arrived at the resort with her family early this morning.To my surprise, she requested that I was I should be her resort guide during her stay. I didn't know why, but I sure was not going to reject the request. I spent most of the morning with Kaley to help her get settled and give her family a tour around the resort. Whilst on my lunch break, I naturally couldn't seem to get my mind off of Kaley, which was the first time that my mind hadn't had any thoughts about my time with Olivia Wilde.As sexy as Kaley Cuoco was, she looked way hotter in person. Everything seemed to be amplified about her, even her big tits. Kaley was giving more than enough of a good view of her cleavage, and she kept bending down in front of me so that she could give me an even better view as they tantalizingly hung down. I was eager to savor her ample breasts at that very moment, but forced myself not to make my intentions so obvious. In fact, it was just as well that I took my lunch break when I did, because I didn't know how much longer I could be around her sporting my huge boner.What was shocking was that it seemed like Kaley was bending down on purpose, and was finding the most random excuses to do so. It even looked like she was trying to hide a little smirk on her face. I figured it was just all in my head, so I soon dismissed any such thoughts. I mean, there was no way such a celebrity would have been coming onto me right? Olivia Wilde was an isolated encounter, surely it couldn't happen with Kaley Cuoco also, could she?She was having a similar effect on me like when I walked in on Olivia naked in the sauna. After I left, I was still rock hard thinking about Kaley, and knew it would be tough to hold off from jerking off until I get home. Luckily I only had a few hours left on the job anyway. Right now I was on my staff break room for lunch, sitting with other staff members who were chatting away about there respective days.As I finished my lunch, my strict "no nonsense" manager Brian Wells, entered the break room. The other staff members quickly stopped eating or there chit chatting as soon as they noticed him walk in."Troy, Miss Cuoco is once again requesting your services. She's back at her vacation house," he said, in a very authoritative tone.I nodded and made my way out the break room. I could feel nearly everyone's eyes on me as I walked by and toward the exit. It was clear that some of the other staff were jealous that Kaley had been requesting me, due to the fact that I was still new and some of them had been here for several years. They no doubt felt that they are more qualified to take care of the MILF celebrity than I was. Since my sexual encounter with Olivia Wilde, I'd gone through a huge confidence boost and in turn, I didn't really care what the other staff thought at this point.I drove up to Kaley's vacation house in one of the resort carts for the staff members, which would allow an easy and fast access around the resort. Her vacation house is one of the more secluded properties in the resort. I was told that most of the celebrities that stayed at "Stay Away", reserved the more secluded vacation houses.I rang the doorbell a few times and there was still no answer. Just then, I remembered that Kaley had mostly been in the backyard since this morning and so I figured she still might be back there. The backyard had a pool and hot tub so usually most guests were enjoying taking advantage of the pool area, whenever they weren't out and about in the resort. I made my away to backyard, stopping dead in my tracks as I saw Kaley wearing a sexy two piece, red bikini, making her way out into the hot tub.Kaley sat down on the opposite side of the hot tub, facing me as I made my way toward her."You're finally here. I've been waiting on you for a while now," Kaley said to me, standing up, her smoking hot body completely soaked. I couldn't help but eye her up and down. She got out the hot tub and walked up to me, swaying her hourglass hips so seductively. "The Big Bang Theory" actress was like a walking wet dream as she soon stood before me. My eyes drifted down to her large ample breasts. Kaley seemed to notice that I was checking her out, and seemed to encourage it with her smile. Kaley posed for me, placing a hand on her hip"Take a picture, it'll last longer," she said sarcastically. She laughed as she flipped her wet ponytail over one shoulder."I'm sorry Mrs. Cuoco-Sweeting. I wasn't trying to offend you," I said, hoping that I haven't landed myself in some trouble."I didn't say that I didn't like it," Kaley said, leaving me somewhat surprised, "And Mrs.? You don't have to be so formal. Just call me Kaley, first name base between the two of us," she insisted.I nodded."Did you need anything Mrs...Kaley? You requested me".."Well I'm the only one home and needed some company. Can you do that for me Troy?" Kaley asked, in a noticeable, sultry voice.All I can do was nod once again."Good. Now come join me in the hot tub."As much as I wanted to join her, I knew how bad it would have looked if someone were to walk in on us. My job could have been at risk for that."Oh I can't Kaley. That wouldn't be professional of me,""Well, isn't it your job to attend to my wants and needs?" she said quite sternly."Yes, but...", before I could finish, Kaley cut me off."I WANT YOU to join me in the hot tub. So you have to do it," she said seductively, running her pointer finger down across my chest, as she looked up at me with her sexy green eyes.Kaley grabbed my hand and led me back to the hot tub. My eyes wondered down to her sexy backside, taking in her juicy round ass cheeks as her hips as they swayed from side to side in her red bikini bottoms. Her glorious globes of flesh looked even more inviting as her bikini bottoms had ridden a little in between her succulent ass crack.The desirable blonde hopped back into the hot tub sitting down as I began taking off my clothes. I stripped down to my green singlet and underwear, soon joining her in the hot tub.Just as I sat down, on the opposite side of the hot tub to where she was, Kaley soon began rubbing her right foot up and down the inside of my leg, staring at each other without saying a word. It was blatantly obvious that she was intentionally teasing me."Do you know why I've been requesting you all day?" she asked."Um, no Kaley. I...I don't," I said nervously, feeling her foot slide higher up my leg."A friend of mine knew I was coming here for a few days and recommended you for my stay," she said, raising an eyebrow.I was surprised by this, a friend recommended me. What friend?"Um...what...what friend?" I asked, getting even more nervous."I think you know...Olivia Wilde. I hear she showed you her oral talents..."I was speechless. Her friend is Olivia Wilde? She wasted very little time in telling her friends about what happened? There was no getting out of this because Kaley already knew everything. A horny look formed on her face as her foot started to twirl and rub in between my legs, fondling my throbbing cock."Hmmm and by the looks of it, Olivia was right. You definitely enjoy working here huh?" Kaley said, moving closer to me and sitting down beside me.Things were quickly building up, the tempting celebrity MILF trying to seduce me and showing the power she had over me."Olivia insisted that I check you out. And now here we are, and you have me all to yourself...what do you want me to do?" she asked.I was still in shock that Olivia practically set this up for me. There were a lot of things that I wanted Kaley to do, but before I could pick one or say anything, her hand was sliding up my right thigh and soon was placed upon my bulge. She began to slowly rub it, squeezing it softly which made me groan inwardly."Did I make you this hard Troy?" she whispered in my ear, stroking my cock through my underwear."Yes," I grunted, trying not to lose all self control."And do you ever jerk off thinking about me?""Yeah," I grunted again, her throaty voice almost making me blow my load."Would you like it if I put my hand in your underwear, and fondle your big, hard, cock?" she purred. Before I could even answer, she did the action that she had just suggested to me. She slipped her hand inside my underwear, wrapping her soft wet hand around the head of my cock, stroking it all the way down my entire length."Damn that feels so good Kaley," I moaned, whilst looking down at her very impressive cleavage.I pulled down my underwear and soon they were floating around in the hot tub. At this point, I didn't care if someone walked in on us. The MILF actress continued to fondle my cock, and before I knew it we were already lustful making out. I managed to put a hand on her succulent right breast, Kaley moaning into my mouth when I squeezed her firm breast."Do you ever think about fucking me Troy? Or jerk off thinking about putting your cock inside my tight little pussy?""Oh fuck yes!" I exclaimed. She had control of me entirely and she knew it."Well you're going to get the chance to do what you didn't with Olivia...Fuck me Troy..."Kaley untied her bikini top and lets it drop into the water, quickly discarding her bikini bottom as well. Even though I wanted her badly, she was clearly the main aggressor. She moved her incredible nude body up to sit in my lap, feeling her velvety pussy lips grinding against my cock.The blonde stunner raised up slightly so that her big naked tits were in front of my face, as she puts both her hands on my shoulders. Once in position, she reached down to grab my stiff rod, placing the spongy tip of my cock at the entrance of her soft, hairless pussy. Without any warning, Kaley forcefully dropped down, moaning out loud as she was impaled upon every inch of my meaty cock, sliding all the way inside her tight wet cunt. Kaley started grinding her hips and bouncing up and down on my bare naked member.I held a tight grip on her hips as I thrust up into her, her very tight pussy starting to slowly loosen, but still gripping me like a vice. I rested my head down on her big jugs as if they are pillows, kissing and sucking her taut nipples in the midst of our lustful fucking. Kaley began doing a slow grinding as she ran a hand through my hair. I took her right tit in my mouth, biting down on the nipple and sucking like an thirsty infant. She started to ride my cock with even more eagerness, trying desperately to get herself off."Oh fuck!! Your cock feels so good inside me! Fuck me, like I'm your slut Troy," She rode me harder and harder with each passing second, water splashing everywhere. Kaley soon turned around, facing away from me, her bubble butt now sitting in my lap as my hard cock speared into her luscious pussy from behind. Kaley erotically gyrated her hips as moans came out of her mouth, every time my hard cock plowed deep inside of her. I kept my firm grip on her hips as she leaned forward, my cock delving inside of her from a different angle.I reached around with both hands to squeeze and grope her large tits, which only intensified her ass wriggling upon my lap. The water in the hot tub moved in mini waves around us as I continued to fuck the hot MILF. I could feel her tight pussy seem to only get tighter as I felt it began to milk my cock. My body lifted up, forcing her forward so her face was against the wall. I was now in control, taking her doggystyle so I could hammer into her backside like a man on a mission.Kaley let out a moan as she put both her hands on the edge of the hot tub, my cock driving balls deep inside her insatiable pussy. The sight of her tender round ass pressing against my thighs every time my cock went inside her, was sending me over the edge."Ugh, oh yes! Oh yes! Oh yes! Fuck me harder! Cum inside me!" The MILF actress pleaded.The way her voice sounded when she moaned was enough to make me pound her cunt into oblivion."Oh fuck...I'm going to cum!" I groaned.I leaned forward, panting and clutching her huge jiggling breasts, squeezing them tightly as my the tension in my nuts released and I exploded deep inside the breathless MILF."Oh yes! I'm going to...ahhhh!" her mouth opening wide in a cry of ecstasy, as we both came at the same time. Kaley was having rapid contractions as she reached her climax. I pulled back her ponytail and weakly slapped her full round ass, her hot little pussy taking every last drop of my young warm seed."Oh fuck!" Kaley cried, milking my cock with her tight pussy. "Oh fuck, it's so hot."I groaned as I shot the last of my man juice up her slot, slowing down my thrusts. Finally with a grunt, I pulled out my cock, letting go of her ponytail as a mixture of my cum and her pussy juices dripped out of battered entrance."Oh my..." she managed to say, her voice hoarse with pleasure, "It's been a long time since I was fucked like that.""That was amazing Kaley...thank you," I replied, almost out of breath."Thank me? I should be thanking you," she said, as we shared a little laugh."My husband will be back with our daughter any minute now. So before anyone catches us, you should go."Kaley was right and I knew it. Fucking in the hot tub was already risky enough, so I knew I'd have to disperse quickly before we pushed the limit even further.After I quickly dried off with a towel and got dressed back into my work uniform, I started driving back towards the main building. I was definitely in saying that this was going to be the summer like no other. First Olivia Wilde, and now Kaley Cuoco, I actually fucked Kaley Cuoco! With Olivia Wilde and I assume Kaley now doing the word of the mouth, there was no telling what other celebrity would come to the resort taking up their recommendation.I parked alongside the other "staff only"carts in the parking area, and went to the lobby of the main building. Lucy, the cute girl next door receptionist, greeting me."Oh, Brian wants you to report to his office asap. Not really sure what it's about, but it seems good," she said, leaving me to return to my last hour of work, a few minutes left for the day.I heard that most meetings with Brian weren't good, but I wasn't worried or stressed because of how satisfying I felt after fucking Kaley. I went with Lucy's vibe, since she had worked here longer than I, so she would know if I was in any trouble or not. All I know is, nothing or no one could ruin my mood right now, not even Brian.