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Rookie Lawyer (Anna Kendrick, Alison Brie, etc)	By : TheChemist Category: Celebrities - Misc > General Views: 2508 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: This is a work of fiction. The events of this story didn’t actually occur. I do know Anna Kendrick, Alison Brie, Alexandra Daddario or AnnaSophia Robb personally or otherwise. I make no money from this story.

Chapter List
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Another day passed and Alison made sure any progress she made on the case was careful, however that meant slow. She was becoming obsessed with the damn litigation, which meant that she sacrificed time at home with Steve. Hell, even when she was there her thoughts strayed to the case, including when she returned drunk to their house after the party and he fucked her silly.
With more progress made, Alison needed to double check some dates and figures with Nicky so she booked an appointment at the jail for the first thing the next day. It felt like a long wait but it would draw more suspicion if she just showed up out of the blue at the jail.
18 hours later, Alison was saying hello to familiar jailors and walking past usual checkpoints. As was the custom, Nicky was already waiting for her in a smaller but still empty room, populated with only 4 tables and a guard posted at the far end to supervise.
“So how have you been” Nicky asked nicely, though she could tell he was frustrated. “Attend Emery’s big party?”
“How’d you know about that?”
“I’m in jail, not under a rock,” the prisoner replied.
“He’s worried about you,” Alison told him after a few moments silence.
“He’s my best friend but he’s currently running my…our…business. I’ve heard he even shook up some of the Board without my consult,” Nicky commented, fist clenching and unclenching.
“It’s in the terms of your contract that he has the authority to do so…though I agree it lacked etiquette.
“He thinks he’s the only fucking boss…”
“Listen Nicky, stay positive. I’ve made progress,” Alison told him.
For the next ten minutes, Alison went through all the specific dates and confirmed details with Nicky, including double checking alibis. It was all there and it was clear to the sexy lawyer that there was something foul going on and she didn’t like it one bit.
“Listen Ali…the last few night…I was thinking about you,” Nicky said when the legal conversation ended.
“Oh? What about,” Alison played along.
“Your beautiful pussy,” he replied honestly, his eyes continuously flicking down to her twat beneath the table. “While I jerked off.”
With this, Alison’s former stoich neutral face had the corners of her mouth curl up into a smile. It was a spur of the moment idea that struck her that day, and she was very pleased that it was able to give him some comfort in horrible circumstances. She told the jailed man as much, which made him nod his head.
“By the way…I have no panties on today,” she added.
Alison had come prepared today, not only forgoing the panties in order to flash him her pussy with far more ease, but she also wore a shorter skirt. Slumping down in his seat, Alison retreated the skirt further up her thighs and spread her legs wide. It was just a small thing, by no means cheating in her mind, but it made her feel sexy and desired.
“Beautiful,” he commented, erection at full mast.
He wasn’t lying either. She normally kept very up-to-date with her personal care and that was the same with her twat. Fresh from a waxing appointment where she had all but a thin strip of brown hair removed, Alison’s pink lips stood out prominently from her creamy thighs surrounding her mound.
Nicky wanted desperately to whip out his hardened member and beat it until it spewed cum all over the plastic table in front of him. However, he knew that the guards would beat him with their clubs then throw him in solitary for that transgression he he subtly studied every detail. He would have to masterbate later in the shower or after dark in his cell, likely both though.
* * *
“Ali, is there anything else you need tonight,” her assistant asked, poking her head into her office.
“No Ashley, that’s everything,” she answered. “Why don’t you take off now.”
“Another late night for you?”
“I’m finally making headway on this latest case and my brain can’t let it go until I reach a point I’m happy with,” the brunette described.
“A simple yes would have sufficed,” the blonde assistant laughed. “Just remember, all fun and no play…”
“Good night Ashley,” Alison cut her off.
The brunette lawyer watched as the curvy blonde assistant she hired months ago gathered her purse and phone. After shutting down her station she left for the only door in the front atrium and nearly walked straight into a well dressed man that was quite familiar to her.
“She’s inside Mr. Barnes,” Ashley greeted.
“Thanks Ashley. And please, it’s just Steve,” the older man retorted.
“Yes sir…Steve,” the blonde replied before they parted.
Steve Barnes walked into the main lobby of the law firm, which consisted of a front desk that Alison’s assistant/receptionist occupied and a few sorted chairs which acted as a waiting room. Her office was just left of center and she was so focused on the papers in front of her that she didn’t see him approach or even hear his dress shoes clapping the floor.
“You forgot we were going out tonight, didn’t you,” Steve Barnes asked.
Alison was a little startled to hear the pleasant voice of her boyfriend who had taken up a leaning position against the open door frame. The older man was about a decade older than her but the 40 year old kept himself in great shape as illustrated by the way his tailored suit fit him like a glove.
“Oh shit…the concert,” Ali swore.
“Well yeah babe,” Steve added.
Alison swung her chair and got to her feet. She apologized to her man as she walked towards him, her commute shortened with him stepping further into the room. She felt the clean shaven skin of his face as her hands closed around his cheeks as she propped herself up on her tip toes and kissed him on the lips, both one portraying her regret and love for him.
“I’m sorry, this case just has me going mental. Actually I could use your advice,” Alison asked, which was greeted with a nod. “I can get the case dismissed like that, but there are a lot of people who don’t want that. And truthfully, I’m afraid about irking these individuals.”
“Ali, you were the one who wanted to move on from family to criminal law, I thought you could handle it without being reduced to a sobbing little girl,” Steve replied.
For most people, that stinging comment would have been a harsh blow. However, Steve knew his devoted girlfriend and it was just the thing she needed to hear. The light-hearted brunette actually laughed at his insult and hung her head low before whipping it up and facing him again.
“Listen babe, you’ve never been intimidated and you’ve faced worse. Go with your gut, your instincts and you’ll be fine,” he added.
“You’re right…again,” Alison grinned. “Now Mr. Powerful Attorney, what do I owe you for the critical advice?”
“Let’s start with you getting down…putting your hands behind your back,” Steve ordered then waited for her to do so. “Good…open your mouth and don’t move.”
The brunette lawyer was allowing Steve to have complete control over her as punishment for forgetting about their date so she followed his instructions to the letter. Since she had come straight from her appointment at the jail to the office, her bare knees rested on the ceramic tiles of her office as she perched on her knees, hands behind her and mouth open.
Steve smiled down at her, knowing that he had dominance over her. He reached down and undid his pants enough to pull free his partially erect cock. He looked down at Alison the whole time, whose eyes kept shifting between making eye contact with him and waiting patiently for his dick to emerge.
As soon as the semi-rigid tool popped free of his pants he placed it right on Alison’s stuck out tongue. All while she maintained eye contact the brunette maneuvered his dick into her mouth and closed around his tip. Before bobbing him, which would come shortly, she started sucking and using her skilled tongue to dart at his piss slit.
“That’s it,” Steve groaned, his cock fully hard now.
Steve grunted loudly into the empty office as her moist mouth began to work. Knowing that she barely had any leverage, the former convicted murderer had to do all the work to get full pleasure from the blowjob. However, Alison wasn’t going to simply sit there, as she started to bob her head over the first few inches of his lengthy 9-inch cock.
He pushed his hips forward while holding Annie’s head in place with a solitary hand at the back of her brunette hair. Steve watched as the first several inches of his cock disappeared inside her mouth. He held himself inside her, soaking in her saliva before withdrawing, feeling the underside of his dick gliding along her wet tongue and finally felt his tool sandwiched between her plump lips.
“Fuck that’s good,” he exclaimed.
Slowly she took over more of the work, using her slender neck to work forward and backwards while his hand changed to more guiding then powering. However he started losing inhibition, thrusting his hips forward when Ali would push her head forward. The result was the tip of his cock poking the back of her mouth, naturally stimulating her gag reflex. Alison took the surprising move all in good order, rolling with the punches as Steve repeatedly drilled the back of her throat causing her to cough more spit on his cock and give him a progressively wetter blowjob.
“Glllcckk…gllllgghh,” Alison gurgled with spit.
Steve wanted to see the result of his face fucking the pretty girl so he pulled his cock and her head away. Like he expected to see, the vision was that of sluttiness with thick strands of saliva connected his pole to Alison’s practiced lips.
“Oh is this hot,” she asked, pretending like she didn’t know that he loved the perversion.
He continuing glaring down down at this, seeing spit covering his member. It seemed to make his dick grow even harder somehow, a feat he didn’t think possible since it was already raging at full mast. Steve re-doubled his clutch on the sides of her head and slammed her face and his dick into each other. This time she audibly gagged, turning the older man on even more.
Over and over Steve plunged his erect cock into her mouth to the beginning of her throat. Each time she sputtered and coughed, spewing more and more spit onto his rod while giving him the wettest and loudest blowjob of either of their lives. Steve continued to dole out the rough blowjob simply because he knew she could take it as they often would experiment sexually.
However, as very much wrapped up in the moment that he was, every now and then when he thought the treatment was getting too rough, Steve would glance down at the beautiful girl. Sure enough, Alison was already looking back up at him with her eyes encouraging him to keep going.
“Get up here,” he ordered.
Alison found herself aided getting to her feet by the dictating male. Her heels clicked on the tiles as she stood up before tilting her head upwards in time for his lips to crash against hers. Unlike their first earlier kiss, this one was more than a greeting as it portrayed all the the lust they both contained in their bodies.
Steve couldn’t take it any longer, he needed to be inside the gorgeous girl. However he still took the extra seconds to unzip her skirt and watch it fall harmlessly down her toned legs to pool at her feet. That also showed off that she wasn’t wearing panties, he assuming that due to thinking about the end of their date when in reality it was for another man.
“Guess I forgot panties today…oops,” she jest with fake innocence.
He leaned in and kissed the playacting girl, making sure that his tongue dominated hers just like he was doing with her physically. His hands were left free to push her business suit jacket off her shoulders, just like she had done to his without waiting for permission. Rather than pull her white shirt off next, he used his hands to reach down and grope her meaty ass.
Alison had a great ass, sculpted through a workout regime of squats and lunges to transform what could have been a flat behind to that of one with nice curvy. It wasn’t overly large like the phat asses all the rage, but for a white girl it had a significant roundness and curve to it. It wasn’t her best feature by any stretch, that feat went to her perfect bouncy tits, but it was a good looking rump all the same.
Speaking of her breasts, they were about to make their appearance. Steve helped lift the much smaller lawyer up onto her desk and then used his hands to grip the hem of her white v-neck shirt. They broke their kiss long enough for him to pull it over her head then tossed it to the floor beneath.
“Fuck…such amazing tits,” Steve commented.
Finally Alison’s most impressive sexual asset came into view…her amazing tits. The globes were rather large, more than a handful for even Steve’s long hands, which was saying something. Located in the perfect center of the breasts were small pink nipples, currently poking out due to the excitement the short girl was feeling.
Though they’d been fucking for over three years, the 40 year old was always amazed by her boobs. Steve still had a tough time believing that these huge magnificent tits belong to a girl that was so petite and that he had access to them at his leisure. Equally impressive was the fact that the heavy boobs hung flawlessly directly in front of her chest without even the hint of sag. They were soft and bounced wildly when she ran…or walked fast because they were all natural, yet somehow were still perky.
“Satisfied,” she said after giving him some time to scope her out.
“Partially,” he replied.
After another kiss, Steve’s hands went straight to her tits. He groped and kneaded the fleshy sacks, occasionally clutching her erect nipples and twisting them between his thumb and forefinger, rolling them around. Alison moaned into his mouth but those didn’t compare to when he slid a hand down and used his talented fingers to rub her pussy.
The woman was absolutely dripping with desire, and Steve was soon to take full advantage. First though, he extended his middle and ring finger, sandwiched them together and hovered over her hole. She was still somehow tight despite daily fucking, but his fingers slid inside her twat without issue given how wet she was.
“Oh God…so good,” Alison moaned.
Even though he had only been fingering his girlfriend for less than a minute, Steve couldn’t take it anymore. Placing one hand on the small of her back to hold her steady, he guided his erect tool into her pussy, entering it with ease until he was completely buried with her. This caused the brunette lawyer to scream even louder but this was far from his end game. He soaked himself within her flowing juices for a long few seconds then pumped once in and out of her twat before withdrawing altogether.
“Tell me what you want and it’s yours,” Alison reminded, sensing she knew what he was angling towards.
“You know what I want baby,” Steve replied.
“Oh yeah?”
“I want to fuck your asshole,” he replied in no uncertain terms.
“Yes sir,” she smiled.
The lawyer with the type A personality realized her boyfriend only took a dip in her pussy to coat himself in her juices for an aide as what laid ahead. Alison felt his tip contact the sphincter that kept things out of her most taboo of holes, simply waiting there for her to relax. The second Steve felt the younger woman’s tone ease up, he made his move by pushing his hips further forward until he felt her anal ring squeeze the crown of his cock, the penetration confirmed by a wet slurping pop.
Then Ali did something she had only done once before…she came immediately after insertion.
If her mind was able to think, which it wasn’t do to the intense pleasure, she’d have known why it happened so fast. Steve was spontaneous, never doing the same performance twice so it kept her on her toes. That, coupled with him making her wait for sex all day made her ride a wave of horniness and longing for hours. Then he teased her with light rubbing, even fucking her pussy for the briefest of moments before giving her an actual penetration.
Steve noticed that her ass seemed to loosen up extremely quickly, especially compared to the semi-frequent other times he’d had the pleasure of getting Alison to agree to anal sex. He thrust into her asshole with slow short strokes to get her warmed up, but it seemed that with each passing moment she was able to take more. Judging that as a good sign, he continued to thrust deeper, slowly increasing the speed until his entire dick was passing in and out of the brunette’s asshole.
“Oh yeah! That’s what I wanted,” Steve grunted as Alison made small, subconscious moans.
Steve had been getting faster and faster at slamming his dick into her asshole so that it looked like a flesh-colored blur that repeated kept disappearing inside her. However, he’d been at it for the better part of 10 minutes and it was beginning to wear on his stamina. He needed a break so he pulled out of her rump, watching with a perverted smile as her once tight asshole stayed gaping open for a few seconds then it constricted back like nothing had ever been inside her bowels.
“Why’d you stop,” she asked with a whine.
“Get on your knees…”
Just like before when he made his demands, Alison listened to him to the letter. Once Steve backed away from her far enough for her to move, the brunette sank to the ground and rested propped up on her knees. She didn’t have to wait long for him to give the follow-up instructions, though she knew what they would be.
“…and suck me,” he hissed.
“You want me to suck your cock after you fucked my ass so good,” Alison asked with a smile.
“Is there a problem with that,” he asked.
“Absolutely not,” she replied.
Years ago, Alison would never have thought that she’d degrade herself so much as to suck on someone’s cock that had come straight out of her asshole. Yet now it had become commonplace in their relationship, just like public sex, spanking and restraints.
Kneeling, she reached out her arm and clutched the base of his member with her dainty hand and moved it up and down, loving how hard and smooth he was. At one time she would have been concerned at how horrendously gross it would be to wrap her lips around something that had come straight out of her ass. Now she knew what it taste like to devour her ass, and she liked it so she opened her mouth and lowered her head so she could take the tip into her mouth.
“Mmmm…yeah,” Steve grunted as he got an extra perverse thrill seeing a woman suck her ass off his member.
As Steve’s cock was engulfed in his girlfriend’s warm, moist mouth, he couldn’t help but continue to groan loudly. Alison was easily talented enough with her mouth that she would have been able to elicit grunts from him on a normal day, but the fact his tool was fresh from her bowels made it even sexier. Looking down at the top of her brunette head starting to bob up and down into his groin, the older man couldn’t help himself by resting one hand on the top of her head, helping her get just a bit more of his flesh into her mouth.
“Mmmm,” Alison moaned while blowing him
“Oh yeah, such a dirty little slut,” Steve insulted while the bookworm tasted her own asshole. “Clean that dick.”
Steve kept peering down his long torso to watch the brunette pleasure his cock with her mouth. Just visible beyond her head, the older man could see Alison’s large tits jiggling in front of her each time she energetically bobbed up and down his shaft. This combined with her natural blowing skills to push him closer to cumming, which was something he didn’t want to do yet.
“How’d your ass taste,” Steve asked, pulling his dick from her talented mouth.
“Really good,” she replied with a smile as she got to her feet. “Loved it like always.”
Steve clutched the back of her head and brought her in for a kiss. His passion was seemingly burning hot in him and he needed to kiss her or else his chest would burst. He held her tightly for a few seconds before letting his hands roam her body once again. One palm found itself at one of Alison’s extremely large tits, squeezing the globe for good measure while his other went down between her legs to rub her still-wet snatch.
“I got an idea,” he said with a wide smile.
“Oh? What’s that,” Alison replied with a questioning look.
Ali wasn’t a big fan of him breaking their naked make-out session due to an unknown eureka moment but she saw him out. But instead of telling her, Steve showed her. Using one of his long arms, he placed it on the desk before swiping across it. Instantly books and papers went clattering to the tiled floor below, making an absolute mess.
“I always wanted to do that,” he said with a gleeful smile.
“You know I’m going to have to clean that up after, right,” she told him.
Steve simply shrugged his shoulders before climbing onto the suddenly clear desk. Despite the wooden table being rather tall, the short Alison was hot on his heels and joined him up on the top. The taller man had gone supine, laying his muscular back on the table in a position that would make the studious lawyer do all the work. Alison didn’t mind though, her earlier orgasm fueling her sex drive even more than ever.
Ali had no trouble swinging her short leg over his torso so that her pelvis hung suspended over the older man’s lap. She had no hesitation steering it back towards her asshole once again, only stopping to rub his slick head around the crinkled orifice.
“Mhmmm,” they moaned in unison as he entered her rump once again.
Alison didn’t cum right away like she did last time, but it still felt amazing to have her boyfriend back inside her. She slide further down on his lap, impaling herself more and more with each stroke she did on him until she was finally gliding down all the way that the back of her thighs would touch the hair-covered skin of Steve’s quads.
“Fuck Ali you feel good,” the lawyer grunted, reaching up to squeeze her impressively sized tits.
Alison Brie moaned even louder as she rocked her ass on his lap with his shaft completely buried in her bowels while Steve played with her breasts. The dual stimulation was driving the young criminal lawyer crazy, but she wasn’t the only one who was enjoying the sex.
From beneath the energetic girl, who had resumed bouncing up and down on his cock, Steve was in a world where only pleasure was able to be experienced. Her asshole was tight, but not too tight to the point where it squeezed his dick painfully like a hungry boa constrictor. Plus from his angle he had a perfect view of her bouncing large tits, her shaven bright pink pussy plus could watch his fleshy pole disappear every other second into Alison’s rump.
Unfortunately the half hour of anal fucking his long-term girlfriend was really starting to wear on his resistance. Steve knew that at this point there was little good in changing position or slowing things down as he knew an orgasm was only a matter of time.
Alison had spent enough time between the sheets (or on a desk) with Steve to know when her man was getting close, what with all the face grimacing and extra firmness in his groping. It also confirmed her suspicions when Steve dropped a hand down from kneading her bouncing tits and moved it so that his index and middle fingers were rubbing her clit. The male lawyer was on the verge of cumming himself but he wanted to make sure that his brunette nymph came with him.
“Almost there,” he warned. “Cum with me.”
Alison grunted her approval but was receiving too much pleasure to reply with words. She simply began to ride his dick harder in her asshole, springing to the top with all the power her toned legs could muster than allowed them to go limp so she could slam down his shaft with reckless abandon.
This was more than enough to get Steve off, pushing him past the point of no return. It also proved too much for Alison as well, especially in combination with his frantic clitoris rubbing.
The brunette was quicker off the draw and beat Steve to the climax. Her second orgasm of the night lost no intensity that the first one had, in fact may have been even stronger. The real kicker for the studious woman was the stimulation from so many different areas. The cock impaling itself in her ass, the fingers to the clit, the hand squeezing her tit and the mouth enclosed on her sensitive nipple made for one power-packed, scream provoking orgasm.
“AWWHHH MMHMMM UUGGHHHH,” Alison screamed incoherently.
“Gonna…ugghh…cum,” Steve warned, face severely twisted.
No sooner had Alison cum had her asshole clamped down like a vice around his already cocked and loaded shaft. As the last word escaped his lips he felt the last wall of resistance break down and the warm liquid began bubbling up from his sack. Steve had thought of really milking the master and slave game and cum on her face, but the thought of not having her snug pressure around his cock just felt so wrong.
Alison barely registered his last words due to her own orgasm, but she certainly felt the first squirt of hot jizz shoot deep into her bowels, coating them. The tall man continued to erratically thrust his hip upwards into her now still body as stream after stream of his thick fluid came flowing out, pouring into her anal canal.
Eventually the gorgeous girl knew Steve was completely spent. His facial expression relaxed into one of serenity, his iron-like grip on her various curvy body parts relented and his hip thrusting stopped altogether, replaced with the mere slight twitching of his sensitive dick still invested in the comfortable clamp she called a rectum.
Having some energy return to her after her climax, she summoned the remains of strength in her tired legs one last time. The innocent-faced brunette lifted herself slowly and carefully off the cleared desk, squatting down to rest her ass on the table then ultimately got her feet back on the floor.
“Well if that isn’t a head clearer then I don’t know what is,” the naked woman commented.
“Did you find some clarity,” Steve asked with a kiss placed on her shoulder.
“I did. I know what I have to do.”
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Rookie Lawyer (Anna Kendrick, Alison Brie, etc)