The Agent- Shailene Woodley
There was nothing about seeing Shailene that was professional. Much like Emma, she had left the agency and went to CAA following some unfortunate fuck ups with the state of the Divergent series after the third film failed miserably and you weren't able to negotiate anything better to salvage the situation. Still, when the two of you met up, it was always a nice and pleasant evening followed by intense knock down drag out sex, much in the same way that you and Charlize Theron interacted. Shailene would come into town once a year and stay at the same hotel in the same room that you two had first hooked up back in 2014. You would meet up and go for a walk and then would have lunch, catching up and making the necessary chit chat. She had found some success with her new career at CAA working for HBO and you were happy for her.
She seemed to know about your harem but wouldn't really press and the two of you enjoyed the meal and wine before you went back to the nice hotel suite which overlooked the bustling LA scene, where the two of you would engage in sexual fury for the rest of the night.
A load was already down her throat by the time you had pinned against the glass window pane, her beautiful natural breasts pressed against the glass as you held her hips arms and had them pinned to the glass as well as your hips were driving into her cunt from behind with a wild fury. She had her head turned to the left and she was moaning and groaning in a disjointed voice as her cheek was being squished against her window as you fucked her cunt mercilessly, feeling her inner walls trembling as the constricted for the eighth or ninth time, your teeth clenching as you felt her gripping your invading shaft with a tightness that hadn't eased up and you decided to pull her arms back and get her body off of the glass, taking her to the floor while still be inside of her as she got into the prone bone position and felt you getting your hands and feet in place as you started pounding her into the floor.
Shailene crying out as "plap plap plap" sounds filled the large suite as her ass cheeks jiggled and smacked against your downward thrusting waist, your toes locking into the floor as your pumped your hips up and along, driving eight inches deep into her cunt with a ramming speed that causes her pussy to spasm and drench your dick with excessive juices as Shailene was gritting and groaning and begging for you to go harder and you felt your muscles straining as you humped away, feeling the fatigue setting in but decided to keep the level of aggression as it was as she was moaning and yelping in ecstacy and as she clenched up and locked her cunt up again you decided you were ready to cum again and pulled out of her, Shailene moaning out in frustration before you flipped her over and hooked both legs onto your shoulders, entering her deeply again which makes her moan.
You leaned your body down and began to suck and lick at her breasts as you pumped your hips forward, crashing into her cunt with animalistic fury as she grabbed at your neck and held on for dear life as you humped away for minutes with a hard and reckless abandon that brought your orgasm on quickly, your throbbing manhood penetrating into her roughly for thirty or so seconds before your cried out and began grunting and then slamming slowly and deeply as you pumped your load deep into her womb, Shailene digging her nails into her your flesh as you felt it strip and redden but your bucking hips kept up the pace and she gasped at each violent thrust as your cock fired strands of hot seed, her inner walls clenching up and covering themselves in your jizz as you buried your head against her chest and closed your eyes as you slowed yourself down to a stop and panted as she moaned and ran her hands along your back as you could feel your massive load already spilling between your crotches.
You and her entwined and got off of the floor, drinking water and talking about how the evening was going so far and you were on the bed, watching as Shailene worked her beautiful feet along your shaft, rubbing and stroking and getting your cock nice and hard again as she then moved and laid on her stomach, stroking her hand along your length before she began to bob her mouth up and along your length before she got it as slick as she wanted it, Shailene getting up and turned herself around before she lowered her asshole over your sensitive and achingly hard manhood, your hands grabbing at her hips as she moves herself up and along and sinks nearly six inches into her colon as you groaned as her balloon knot was stretching yo accommodate but was still extremely tight and even as she began to rock herself back and forth, stirring your dick along her inner anal walls as she began to move herself up and along as her feet where planted against the mattress and was helping her keep her balance as you moved your hands towards the small of her back to help keep her upright as she crashed down in the reverse cowgirl, fucking herself in the ass with fast and hard thrusts down, her voice creaking and cracking with every gasp and yelp as you just moaned and let her keep up the wild pace until she rubbed her clit with a free hand and screamed out loudly as she came against her hand and slowed down as her sweaty body was racked with pleasure and you felt body seizing up as you ran your hands along her thighs and hips before she settled a bit and found a nice groove to settle into, using her leverage to rock herself against your cock for the next several minutes. After a while she couldn't keep get balance up and you moved her off from the position and held her against you as you both were on your sides, Shailene rubbing her arm back against your neck and pulls you into a kiss as you moved against her, crashing into her ass in the sideways doggystyle.
You and Shailene's lips were locked together as you ran a hand along her breasts and massaged it as you kept thrusting into her ass from this sideways position and she bucked her hips against you to add more force to your hips crashing against her and she began to moan and dirty talk you as she could feel your next orgasm beginning to build as you began bucking wilder and faster and more aggressively and she cooed for you, her voice becoming more assertive and demanding and you groaned and grunted as you felt her rubbing herself as she came multiple times before you closed your eyes and groaned as you pressed in and started cumming deep into her rectum.
Shailene giggling as she cooed happily, commenting about how she can feel your member expanding her asshole as your cock jerked and pulsed as you fired spurt after spurt into her colon, dousing her insides with your hot jizz as you held her for a few minutes before your cock softened up and you pulled out of her anus as a trail of your jizz leaked out and drizzled down her cheek and onto the bed.
The two of you robed up and went onto the balcony, drinking and hydrating back up as she asked how the business was going. She congratulated you on the Oscars and you congratulated her for her continued success and she wonders aloud if she had made the wrong decision in leaving. You told her she did what was best probably and she shrugs and asked when you left for China. You had a week long stay in Beijing planned to cover for Alex who had called and asked for you to represent the agency in some bidding wars for Chinese backed funding for some upcoming projects that were in jeopardy due to the coronaviruses impact on the film industry and the Chinese market slowly pulling out of big money deals.
She chuckled and says she knows Damien has been having issues and would find it funny if you made more headway and you took the little jab and locked it away as you talked about the trip and the state of the industry before deciding the break was over, Shailene taking her robe her as she struts inside and tells you to hurry up and join her in the shower, which makes you smirk as you stripped yours off and followed her eagerly.
End of chapter.