The Agent- Sarah Silverman
Sarah was hosting the Golden Globes this year, which was a big thing for her career and she was eternally grateful for the strings you pulled to get her the hosting duties. Though to be honest, you were sure it had more to do with Ricky Gervais putting in the good words and her friendship with Dave Chappelle whom they really wanted to host the event. But nonetheless Sarah was grateful, and her gratitude was on great display. She has you seated in her makeup chair, as she was in between practice runs at the venue. She had stripped her dress off and locked the door and was kneeled before you, rubbing her beautiful full and real breasts along your throbbing member as your cock had been sucked thoroughly before she began to fuck you with her tits, the sight of Silverman's amazing breasts moving up and down along your girthy length making the impending orgasm draw closer and closer and you say as much as Sarah cracks a joke which makes your chortle, as you then began to moan as she worked her chest up and down, pressing her hands tightly together as she added more friction to the movement and could feel your orgasm drawing, she flicks her tongue out and catches it against your tip as she began to wrap her lips over the tip and suck and draw as she kept tit fucking you and you grabbed the arm rests and cried out her name with a grunt and a groan, shuddering as you saw stars, firing off strands of cum into Sarah's mouth as she giggles and moans, licking her tongue in circles as she worked her throat to suck down the globs of hot seed that were coating her throat and steaming down into her stomach.
You felt the last few spurts leave your body and you shudder as she kept sucking over your sensitive head, your voice breaking as she just giggled and then let your dick out of her mouth with a "plop" as she showed her mouth and you could see a little strand of cum coating her cheeks as she licks her fingers and ran her hand over your still hard cock. She asked if you wanted to fuck her, and the mischievous grin made you think there was a catch, but you said yes because you did want to fuck her. She was a beautiful middle aged woman, her Jewish features only highlighting the things you liked about her. She stepped out of her dress completely and leaned back against the makeup desk as she hiked a leg up and placed it on the desk, rubbing her pussy lips as she had a decent amount of pubic hair which didn't bother you at all. You stood off of the chair and leaned down, stroking yourself as you were still hard as your tongue found her clit, rubbing it along in circles as she moans and began to rub her breasts as she felt you licking and sucking and slurping at her juicy cunt, an orgasm ripping through her quickly as she moans your name and shudders as you focused on her clit with quick tongue licks that causes her to curse before orgasming again. You knew it was time and you licked on her pussy for another minute before you stood and leaned yourself forward, wrapping her legs around your waist as you slowly pushed seven and a half hard inches deep into her cunt.
Sarah rakes her nails across your covered chest as she then took a handful and pulled you down into a long kiss as you both moaned as you started slamming your hips into her, Sarah wanting it nice and hard as she always did and get quick orgasm confirmed your knowledge about her body as she broke the kiss to curse and cry out happily as you began to fuck her hard and fast, Sarah's breasts swaying and bouncing as you drove into her over and over over, each hard inch crashing deep and firm as her cunt was making "squishing" sounds as the "fap" sound of waist to waist action filled the small room.
Sarah leaned up and grabbed behind your neck as you hooked your arms under her legs and picked her up, Sarah by no means being a light woman, so her surprise at you keeping her in the air, and still slamming into her in the standing missionary caught her by surprise as she came hard and threw her head back to bellow, your mind racing with whether anyone had heard it and you quickly took her to the floor and but her legs over your shoulders and folded her up as she just giggled and slapped at the floor as you pounded her cunt fast and relentlessly, Sarah grabbing and smacking and reaching for anything as her mouth was constantly cursing and moaning from the assault, but also from the neverending waves of orgasms that were besieging her body, and as your hips kept their fast pace, and your sweat dripped from your brow and onto her naked body, you could feel the churning finally begin again within your loins, and the end being near gave you the motivation to keep the pace up, your muscles ache and your body was going to feel it, you had never gone this long and hard and steady but Sarah's breasts heaving against your chest, the sounds of her orgasm voice and the dirty talk she would try and slip out before she broke into a long cry, cultivated what was another massive load, which you alerted her to by saying her name and that you were cumming a few moments before you slammed in and held your hips against her mound, leaving nearly eight throbbing hard inches inside of her cunt as her pussy locked up and orgasmed just as you started pumping spurt after hot creamy spurt of seed deep into womb. Sarah ran her hands against your neck as you pumped wildly and forced every ounce of cum into her womanhood as her trembling and pulsing inner walls were being coated down by a thick layer of your warm seed, and the two of you kissed for a long moment before you leaned up and pulled out of her once the room stopped spinning and your cock had begun to soften as it still jerked and pulsed.
The two of you laid on the floor and she broke the panting and heavy breathing with a well timed joke that made you both laugh and giggle as she turns and gave you a kiss before she bounced up and got herself back into her dress as you put your boxers and slacks back on before your grabbing your shoes as she slipped her heels on and checked herself out in the mirror. She knew she needed her makeup run done and gave you a look as if you started the sexual encounter which you certainly did not. You made sure you both weren't a complete mess before unlocking the door and calling for her makeup team and you spent the next few hours watching her rehearsals feeling really good about how well she was going to do. She had jokes that were going to make headlines but any publicity was good publicity and you checked your phone and made some calls before texting your mom that you were on the way as you had promised to come visit her.
Erin greeted you first with a warm smile and a hug and you gave her a cheek kiss and asked how she was before you headed into the living room. Mom gave you a warm and long hug and dove quickly into the love life as Erin was listening with a fascination at the prospect of a harem and who were involved. You and your mom talked about dad and how his was handled and Erin made a nice chicken dish that you wanted the recipe for but she wouldn't give much to your chagrin. But you took it in stride and with a good hearted nature as Erin was doing more than enough being here to watch and take care of your mother.
You, mom and Erin talked for the next several hours and as midnight drew closer, your mom was tired and needed to sleep to be able to get up in time for her doctors appointments and physical therapy in the morning. You and Erin helped her get upstairs and put to bed and she told you to stay over tonight as she didn't want you driving so late all the way back into the city. You took her up on it and gave her a goodnight kiss and a I love you before letting Erin help her disrobe and get ready. You went into your room and thought about the things your mom had gone through and where she was in life when Erin caught you by surprise as she was standing by your door and asking how badly you really wanted her recipe. You shrugged and smirked and said it wasn't a big zealt, but Erin stepped into the room and closed the door which threw you off a bit but not as much as when she began to strip her clothes off. For an older woman she had a really nice body, one she kept in well enough shape, that even the adage of time couldn't take away. Still the stunned look on your face didn't seem to deter here and she asked again how badly you wanted her recipe.
You asked why she was doing this and as she came and pulled at your slacks, working your belt off with a cool and collected confidence that made your dick immediately harden and stiffen up, she said that all of the talk of your and your parents exploits made her realize she was missing out on good fucking, and that if a perk of working for your mother included getting fucked by you, she wanted to exercise that perk. You watched as she got to her knees and began to stroke your cock comfortable with both hands, your dick beginning to throb already as you couldn't believe this was happening, but you weren't going to complain even as she began to suck along your tip and down a few inches before she traced her nails across your balls, massaging and tickling them which made you squirm a bit, Erin smirking as she gagged down six inches before she settled in a steady bob along five and half inches, stroking what she couldn't fit as you admired her face as she sucked you off before admiring the rest of her body, her beautiful perky breasts that you didn't think had had work done but they're almost ageless looks compared to the rest of her indicated she indeed have games, but well done fakes.
She sucked you down before she gagged herself again and pulled herself off gasping and coughing before she moaned and leaned back and got into her elbows, hiking her legs up your own before she wrapped her toes around your shaft and began to work her legs back and forth, rubbing and stroking her feet against your shaft. She wasn't an expert by any means but for someone who probably didn't do this much, it was a valiant attempt, and her manicured toes told you she did take pride and care in herself and her appearance. You grabbed her feet and held then tightly to the side of your achingly hard manhood and began to pump your hips back and forth, fucking her soles as she just moaned and rubbed her clit and breasts as she had gone flat on her back and watched as you enjoyed yourself on her soles, before the temptation became to much to ignore. You grabbed her by her hair and pulled her up and tossed her onto your bed, which made her help in surprise and then giggles in anticipation as you got her into all fours and smacked at her nicely shaoed ass before pushing your head into her pussy from behind, a nice warm and tight welcome that made you suck your teeth as you groaned and worked six inches in somehow as she yelped and gasped and gritted her teeth as well, as she probably hadn't had a real dick in quite some time, much to your surprise.
You grabbed her hips once you felt she was a bit more relaxed and adjusted and began to rock back and forth, gathering speed but slowing down when her gasps went to yelps, and you had to remember to adjust to their needs and not your own. Erin moans and reached down between her legs and felt your driving cock plunging in and out of her before she rubbed her clit fast and bit her lip to stifle a scream but you told her as you've told many before that your mom couldn't hear anything from this side of the house with the door closed and soon she was letting her voice be heard and known as you drove into her more frequently, Erin crying out as she threw her head back and let out a shriek as her cunt locked up around your dick and she came, her entire body trembling as she bucked back wildly and began to lose her balance as her hands gave and she hiked her ass up even more as her lower half was pushed into the bed as she panted and groaned as you continued to fuck her until the build of your own orgasm came bubbling up and you gripped her ass cheeks and rocked her back into you for a few more moments until you couldn't hold it back and you began to cum, your eyes crossing and your body feeling heavy from the intensity as you pumped spurt after spurt of your warm seed deep into her mature chasm, her pussy clenching and spasming wildly as her entire body felt hot, as if the heat of her orgasms had raised her entire body temperature by many degrees.
You pulled out once the last few drops left your dick and coated her inner walls, and you collapsed beside her, as she had curled up already with a content and satisfied grin. You laid beside her and ran a hand along her flesh, getting a better feel of her and you chuckled to yourself as Erin was already halfway asleep, draped in a sheet which was coated with your sweat. You finished stripping your clothes off and thought about how your mother was gonna take the news. You hoped it wouldn't mean having to get rid of Erin, but you knew your mom well enough to know she'd find it funny.
If anything Erin may quit cuz your mom was a ruthless joker who would probably tease her endlessly from now on. Your mind thought of other things until you couldn't keep your eyelids open and soon you were fast asleep yourself in your old bed with the craziest week of your life coming up.
End of chapter.