57 Jennifer Aniston

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The Agent- Jennifer Aniston

Alexandra would be dropping by at some point tonight and you were buried in a work the last few days to keep your mind busy. You weren't good with emotions and handling these things and you knew either Alexandra or yourself were going to be hurt in the end. It bothered you to know this but you knew it was going to have to happen. As you drove to the office to meet with one of your dad's favorite clients, the ageless Jennifer Aniston, you couldn't help but think about the first time you and her had met way back in 2010…

Flashback

Jennifer was getting ready to shoot a film called Horrible Bosses which would be a different type of role for her. Your father's health had been declining by this point and he had asked if you would go to her hotel and talk with her about whatever she was wanting to have a face to face about. You said it course and made your way to the hotel and took the elevator to the hall and room number you had been told to go to. You knocked a few times and she told you to come in, which didn't seem irregular to you before you saw her sitting at the edge of the bed, wrapped in a silk robe as her hair had already been dyed for the film which made her look both incredibly sexy and refined. She smiled as she asked if you were your father's son, and you nodded as she smiled and stood up, walking to you as she shook your hand and introduced herself formally. You asked what was bothering her and she took you to the bed and made you sit down as she smirked and undid the robe, revealing her amazing figure as she wore a lingerie set that was crotchless and had her nipples exposed through the bra. Your initial thought was shock, but it quickly faded to arousal as she looked amazing. She smiled as she saw your face trying to register what was happening and she strutted towards you as her pantyhose was attached to the crotchless bottoms as she cocks her head and asked if you liked what you saw. She wasn't sure if she was pulling off dangerous cougar and you assured her she was. She thanked you and squatted down, getting to her knees as she worked at your belt and then moved your slacks off along with your boxers as your cock sprung up and  stood at attention as she gasped and cooed happily at the sight as she took a hand and ran it smoothly along your length as she lamented that she hadn't seen a dick this big before that wasn't in porn. She said your father really came through for her by sending you here, and you wondered if your dad had just pimped you out. You table the thought and decided to focus on what was happening as she had begun to lick from the balls to the tip, working her tongue along your shaft before she would suck the tip and then go back to licking, your dick reacting by twitch and throbbing in her grasp as she then began to suck down over five inches with a gusto and a need as she moaned as she bobbed her mouth up and along, your hands gripping the edge of the bed as you felt your load building, which upset you as she must've felt the throbbing increase as she began to suck faster and more vigorously. You did your best to hold out and the next two minutes was an agonizing act of contrition to not cum but as she slurped and sucked and moaned happily as she could feel you squirm with anguish, you eventually let it all go and felt the orgasm rip through you as you grabbed the back of her head and held her mouth down over the five inches she was sucking over, Jennifer moaning as she just relaxed her throat and felt the spurts of cum shooting down her mouth and into her throat in globby spurts, her hand stroking your exposed length as she sucked down the load with a bravado that you had never had up to that point. You shuddered and shook as she slowly slurped her way up along your shaft and held her lips over the tip as your dick jerked and pulsated against her lips as she kissed the head and winked at you as she said you lasted longer than she expected. Looking at the hardness of your length she smirked and made you scoot back on the bed as she crawled up beside you and then straddles your lap as she ran her wet milfy cunt against your length before she slowly worked her pussy down, her lips tightly gripping your length as you threw your head back and moaned loudly as she did the same, her knees pushing up against your side tightly as she worked herself to having nearly inches deep within her as she could still feel your dick twitching from the load you shot down her throat. She grabbed your chest and began to grind her hips back and forth, stirring your dick along her inner walls as she only bounced whenever her orgasm drew closer and the added pressure of your dick spearing up deep inside of her caused her to slow as she screamed and then coo for the entirety of the orgasm as she slowly rocked her hips back into a faster pace as your hands reached up and began to massage and play with her tits as she moans and express her like of this as she grinded and bounced over your dick for a solid give minutes, working three long and body shaking orgasm through her before she slowed down to completely as she had to catch her breath but your dick was achingly hard and sensitive and you needed to fuck this starlet more then you had ever wanted to fuck anyone before. You twisted your hips and rolled her onto her back as she giggled and laughed as she locked her legs begins your knees and grabbed at your neck as you planted your palms by her head and began to hip thrust into her using your knees as the stability to pump eight inches in and out of her hard and fast, the "plap" sound of skin crashing into skin and your balls smacking the underside of her ass only increased both of your moans and groans as she arousal began to build as your stiff dick penetrated in and out vigorously as you slammed into Jennifer's cunt with a youthful abandon. She reached down and grabbed at your ass as she began to beg for you to go harder, your hips adjusting from the fast pace to a slow deliberate pace, each thrust a hard buck that sends shivers through her body as she came hard after a few of these hard slow thrusts as she threw her head back and smacked at the headboard of her hotel bed as her pussy locked up tightly across your driving dick which made the thrusts harder but more pleasurable as your balls began to churn again as the added strain of the thrusts and the tightness of her kegel clenching inner walls beginning to draw your second load as you picked up a little speed as you worked into her, throbbing madly as you stretched her inner walls and felt her pussy seize up and as she drenched your dick with juices. She let out an accompanying scream of pleasure as she came and the friction from her wetness coating your dick as she stayed tightly locked around your driving dick became to much and you groaned out her name and kissed her, bellowing against the kiss as you started firing rope after rope of jizz yet again, this time deep within her milfy cunt as she rubbed your neck and face as you shot thick spurts deep against her milking snatch, coating her inside as she broke the kiss and giggled as she smiles and tells you you are a wonderful lover, which made you blush as you cock slowly softened a few minutes after the last drops of cum left your body and poured into her. You pulled out of her and laid on your side beside her as she turned and smirked as she laid her head on her elbow and began to talk with you about how you were liking being involved in the agency. You and her talked for hours and as your memory of that night faded you pulled up to the office and parked as you smirked and shook your head. 

Present. 

Jennifer, even ten years older from that first encounter looked amazing and you smiled as she was talking with Danicka when you got off of the elevator to your floor. She gave you a cheek kiss and a warm smile as the two of you went into the office and began to talk shop and about business, dropping little innuendos and reminiscing about times before. She was running behind for her other things all day and she apologized which you say she didn't need too and that you would get everything written up and sent over to the studio for a final clause approval before she started filming. She says she'll make it up to you and blows a kiss as she hurried out of the office and to the elevator as you did as you told her and got the contracts written up and sent over before the work day was done. You decided to head straight home and cook and clean before Alexandra got there and sitting through traffic you became a frustrated ball of nerves. You cleaned up and decided against cooking as you felt you were just going to throw up once it was all done and when the doorbell rang and the security feed came up you couldn't believe what you saw. You gulped and opened the door as Alexandra stood there, right next to Caity. Your heart kept from your throat as the two women didn't speak and just walked into the house as you shut the door. 

End of chapter

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