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Jennifer Secures the Deal

Category: Anal Sex
16.02.2019
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Jennifer looked out of the large glass windows at the front of the reception into the bleak January afternoon. She couldn’t remember the last time she’d seen the sun, and with the economic climate so uncertain she’d decided not to visit the travel agents over the Christmas period like she normally did. No, she’d just have to wait a few more months and hope it was a good summer. She accidentally kicked the gym bag she kept under her desk, at least she still kept herself in shape, even if she was a bit paler than she’d ideally like.

Actually she was in very good shape, 26, and with a long shock of dark brown hair that reached past her shoulder blades. She felt good, and though she would have liked a slightly bigger chest, she wasn’t about to go the artificial route. Besides, she didn’t have any trouble attracting men, just not the kind of men she wanted!

An Alpina BMW pulled into the car park outside, it was only a couple of months old and gleamed as if it had just been driven out of the showroom. It was completely black, not a hint of chrome anywhere, even the grill was black, and must have cost at least a hundred grand. Jennifer shifted in her seat, Mr Thomas had told her that he was expecting a couple of very important clients today and had asked her to make sure they were looked after perfectly. Jennifer prided herself on her customer service skills and was confident that she wouldn’t let herself or the company down.

The two men climbed out of the car and reached into the back seat to retrieve their jackets. They locked the car and walked slowly over to the large glass doors opposite Jennifer’s reception desk. The doors slid open as they approached and the two men looked vaguely relieved to be in the warm reception after their brief exposure to the weather. Despite that and even though Jennifer smiled welcomingly as the two men walked up to the desk, they did not smile back.

“We have an appointment with Mr Thomas,” said the older of the two, “for 2PM.”

“Mr Griffiths and Mr Levinson?” asked Jennifer politely.

“Yes, of course,” said the older man, rather curtly.

“Would you like to take a seat please, I will inform Mr Thomas that you are here.”

The two men sat down without another word and Jennifer slipped into Mr Thomas’s office.

“They’re here,” she said, pointing at the door to the reception.

“Bring them in then, don’t keep them waiting!” Mr Thomas looked rather anxious.

Jennifer returned to the reception and the two stony faced businessmen.

“Would you like to follow me please.”

The two men pulled themselves up out of the reception chairs and she led them into the office. Mr Thomas introduced himself as David and the men introduced themselves as John Levinson and Terry Griffiths. They sat down and Mr Thomas asked if they would like a drink.

Jennifer was dispatched from the room with an order for three coffees which she quickly poured and returned with on a tray. She walked across Mr Thomas’s large office, concentrating on not spilling the drinks, but couldn’t help noticing that the younger of the men, Mr Levinson seemed to be more interested in her shapely legs than what Mr Thomas was saying.

Usually, Jennifer might have been flattered, he was after all quite good looking, tall and obviously worked out as he filled his suit very nicely. But there was something a little unnerving about these two men. She just couldn’t quite put her finger on it. If she hadn’t known which company they had come from she might have pegged them as loansharks or some sort of criminals. Still, she knew they had come from Pegasus Machinery, a thoroughly respectable company and from the way Mr Thomas was fretting over them, they were obviously either about to withdraw their business or more hopefully award a whole lot more. God knows the company could do with a whole lot more, then maybe she could book her holiday!

Jennifer walked back to the door, conscious of those eyes on her legs again and returned to her desk. Once there she flicked her computer screen on and accessed Pegasus’s account. They were a good customer, but not one of the companies biggest. Of course Mr Thomas wouldn’t want to lose any customer but he seemed far too on edge for it to be simply about losing a couple of grand a month. Jennifer exited the account and turned off the screen, the more she thought about it the more she thought she could smell new business, and hopefully big business!

Jennifer continued with her other duties and almost forgot about the meeting going on in the office to her left. She looked at the clock, 4:15PM, only another hour and then she was off to the gym. She wondered if the guy with the dark green vest would be there this week, she had watched him press some impressive weights a fortnight ago and had rather fancied the idea of him lifting her up and carrying her off to his bedroom, but last week he had been noticeable only by his complete absence.

By 5:10pm almost everyone else had left the building and she was just about to turn her computer off herself when Mr Thomas appeared to her side. He looked nervous and agitated, Jennifer smiled at him, hoping that she wasn’t about to receive some bad news.

“Errr, Jennifer, are you in a hurry?”

“Well, I was just on my way to the gym….”

“Please?” he looked utterly desperate.

Jennifer sighed quietly.

“They want to go for dinner….and they asked if you would come with us.”

“Me?”

“Yes, you.”

“But why?”

“I have no idea…look Jennifer I’m on the verge of a deal in there. They want to put a new contract our way that will be worth hundreds of thousands of pounds, maybe even millions….you know I wouldn’t ask you if it wasn’t important Jennifer, and this is really, really important.”

Mr Thomas emphasised the point by resting his hand on her arm.

“Jennifer if we get this contract there’ll be no more job security issues, I’ll be set until I retire and I’ll make sure you are first in the queue for a pay-rise.”

Jennifer looked at him, her face softening a little.

“Are they any more cheerful than when they came in?” she asked, smiling.

“Oh, they’re not too bad, once you get to know them…..”

“Okay,” she said, “but I want that rise!”

“You have my word!” said her boss, looking visibly relieved.

Jennifer turned her computer off and pushed her gym bag back under the desk, it could wait until tomorrow, she reasoned.

“Thank you Jennifer, you’re a star.”

Jennifer grimaced to herself as Mr Thomas went back into the office to give the guys the good news. Oh well, she thought, at least she might get a nice meal out of it.

Twenty minutes later Jennifer found herself in the enormous back seat of the black BMW. The leather still smelled new and the car just dripped money. Next to her Mr Thomas was fidgeting nervously and Jennifer put her hand on his knee to calm him down, not thinking what she was doing. Mr Thomas nearly jumped out of his skin as he felt her hand on his leg.

“Are you okay?” she said. She’d never seen him so nervous in her life and she’d worked with him for nearly five years.

“Oh, oh…..yes, I’m fine,” he said unconvincingly.

“Well you don’t look it.”

“No really, I’ll be fine.”

The car pulled up outside a local Italian restaurant and the foursome disembarked from the expensive BMW and headed inside.

After the first bottle of wine had been drained, everyone was feeling a little bit more relaxed. Well, everyone except Mr Thomas of course. He was still fidgeting madly and there was obviously something on his mind.

As they ate the meal, Jennifer started to warm to the two men opposite her. The younger man, John was quite attractive, especially now he’d dropped the ‘hard businessman’ act and the older guy was friendly enough once he’d got a drink in him. The meal was delicious and she told herself she’d work it off the next day in the gym, so all in all it wasn’t a bad evening, and if it got her a rise well all the better!

The drinks continued long after the meal, although Jennifer was pleased to see that Terry had switched to water after his second glass of wine, she didn’t want this all to go tits-up because he got stopped for drink driving, or worse!

Finally the restaurant staff started clearing up around them, they were the only customers left in the place, and as the time drew nearer to leave Jennifer noticed that her boss’s nervousness was returning with a vengeance. He went to pay the bill and Jennifer tried to keep her eyes open, she’d had more wine than any of them and she really could do with getting home to bed.

The four of them piled back into the BMW and Jennifer nodded off in the backseat, her head on Mr Thomas’s shoulder. The car pulled to a halt and Jennifer woke up abruptly. She looked around and realised they were back at the office.

“Why have we come back here?” Jennifer asked.

“The contract is on my desk,” said Mr Thomas conspiratorially, “all we have do is keep them sweet until they sign it.”

“What do you mean ‘keep them shweet’?” slurred Jennifer slightly.

“You’ll see, just remember, if we pull this off you can have whatever you want, a company car, a big rise, anything you want!”

Jennifer squinted at him.

“Seriously?”

“Yes,” hissed her boss, “just do whatever they want, okay?”

“Okay!” Jennifer giggled and pushed the car door open. She wobbled slightly as she moved towards the door, the cold air doing little to counteract the alcohol in her system. As she reached the door she miscalculated the step and stumbled, John caught her as she fell and held onto her slightly longer than was strictly necessary. Jennifer liked the feel of his strong hands around her arms and she had a brief image of herself laying on her back as he held her down and fucked her.

The image lasted but a second and was soon forgotten. Mr Thomas led the three of them back into his office and Jennifer saw the contract laying open on his huge desk, a silver pen laying next to it, all ready for signing.

John and Terry sat down in the chairs opposite the desk and Mr Thomas sat in his own chair. Jennifer looked around for another chair but there weren’t any so she leaned against the edge of the desk.

“That doesn’t look very comfortable,” said Terry, patting his knee.

Jennifer looked at Terry, then at her boss, who nodded as he bit his lip. Jennifer slowly moved towards the older man, she guessed he must have been in his late fifties, definitely twice her own age, and slid herself onto his knee, her thin, charcoal coloured skirt riding up slightly as she did so.

“That’s better,” said Terry as he wrapped his arm around her waist.

Jennifer wiggled as she felt his hand pressed against her stomach, she suddenly felt rather warm and reached up to undo a button on her white blouse. As she did so she glanced at Mr Thomas who licked his lips unconsciously.

The three men continued talking business, almost ignoring Jennifer. But as Jennifer sat there she felt Terry’s other hand move onto her leg and slide ever so slowly across the top of her thigh. Jennifer froze, and suddenly the penny dropped, no wonder her boss was offering her everything under the sun. She looked down at the hand that was moving down inbetween her thighs and pushed her legs together, halting it’s progress.

Terry didn’t move his hand, he just left it there and continued the conversation and eventually Jennifer relaxed her thigh muscles and his hand edged lower. The office was warm and the wine in her system was still making her a little woozy, so she kept drifting in and out of fully realising what was going on. As she started to relax a little she felt Terry’s other hand move upwards and cup her left breast and she tried to stand up. Terry held her tight and as she turned to look at John for assistance she realised he was already next to her, smiling as his cock tented his trousers. He stepped closer and placed his hand on her right thigh, pulling it towards him to give his friend access to her pussy, as her skirt rode up even more.

The simple act of pulling her legs apart switched something in Jennifer’s brain and she suddenly felt very submissive. She looked up at John as he unbuttoned his shirt, revealing his toned upper body and sighed as she felt Terry’s fingers gently stroking her rapidly moistening pussy through her black lace underwear.

John leaned forward and kissed her on the mouth. “Don’t be scared, no one wants to hurt you,” he said quietly.

Jennifer felt herself opening her legs wider and she reached out to rub John’s cock through his trousers. It felt thick and hard and she wanted to see it. Then, once again Jennifer was suddenly aware that she was about to fuck someone she’d only met a few hours before and possibly his colleague as well. What the hell was she doing. She panicked and pulled her hand away, but John grabbed it and placed it gently back on his twitching cock.

“Relax,” he said.

Jennifer felt Terry’s fingers pressing harder against her knickers and parting her pussy lips slightly, she sighed loudly, her physical needs starting to outweigh her reservations about the situation she now found herself in.

“You’re wet,” whispered Terry, as if she wasn’t aware of the ache between her legs.

Jennifer just groaned as she felt his fingers slide underneath her knickers and he began to softly rub her pussy lips. She closed her eyes as she enjoyed the sensation and when she opened them again she saw John standing right in front of her, his rock hard cock pointing straight at her face.

“Suck it,” he said.

Jennifer pulled him closer and John fed the head of his cock between her open lips. He watched intently as her lipstick smeared up it’s length as he fed it into her waiting mouth, then pulled it out and wiped it on her cheek. Something about this simple act made Jennifer hornier than ever, it was as if he was demonstrating his dominance over her, letting her know that he knew where the balance of power lay and that he was more then ready to exploit it.

She moved to suck his cock back into her mouth, feeling that she could reassert herself a little by dictating the course of events, but John was too fast for her and used his fingers to pull his cock up against his stomach.

“No! Lick my balls,” he ordered.

Jennifer submissively bent her head lower and her tongue snaked out, thoroughly coating his neatly trimmed balls with a thin sheen of saliva. John wanked his shaft as she licked him and then dropped his cock and pushed it back into her mouth. Jennifer started to bob her head up and down on his shaft, but John grabbed it and held it still and started fucking her mouth. Making it clear once more that he was taking what he wanted, that her only purpose here tonight was to serve him and Terry’s needs.

John pulled his cock out of the woman’s mouth and tilted her head up, he leaned down and kissed her deeply, his tongue snaking into her mouth and tasting his own cock on her tongue. He’d always loved that and he smiled at Jennifer as she felt his hands move to her midriff and then felt her blouse being roughly ripped open, exposing her black lace bra. Jennifer gasped loudly as the material tore, several of the buttons falling to the floor.

Almost instantly she felt Terry’s free hand move up and push underneath the cup of her bra, his rough fingers rolling her hard nipple and then squeezing it a little harder than she really liked. Jennifer groaned loudly as Terry’s other hand began burrowing deeper into her now dripping cunt and she opened her legs even wider to give him greater access.

Then John fell to his knees, eager to taste her cunt. He pushed Terry’s hand out of the way and roughly pulled her knickers down her legs and off, then he thrust forwards, his tongue stiff and pointed. Jennifer gasped as she felt his muscle first penetrate her and then slide up between her lips to her aching clit. He licked her for a couple of minutes, getting her hole nice and wet and then lifted her off Terry’s lap and onto the desk. Once there he yanked her skirt down and threw it across the room. Jennifer moaned loudly as she lay back on the desk and watched Terry pulling his hard cock out of his trousers. She almost did a double take when she saw the huge cock he held in his hands, she had thought John quite well endowed when she had sucked him earlier, but Terry easily eclipsed his younger colleague.

John moved between the girl’s legs and she wrapped her ankles behind his back pulling him towards her. Once again John wouldn’t be controlled, he teased Jennifer’s cunt with the tip of his cock, up and down, up and down. Jennifer mouthed the word ‘please’ and John smiled. He lunged forward and his cock penetrated her deeply. Jennifer let out another loud moan and as she turned her head she saw, almost forgotten, Mr Thomas standing on the other side of the desk, his cock hanging from his trousers, his hand beating it frantically.

Jennifer turned away quickly, suddenly conscious of where she was and what she was doing once more. She made to sit up but Terry was at the side of the desk now and his nine inch cock was hanging next to her face. Now she could see it close-up she was even more impressed by it’s girth than it’s length, it was a monster. Terry pushed it towards her mouth and she found herself struggling to take it between her lips. After a few moments Jennifer’s jaw started to ache slightly, but this just emphasised to her how thick it was and how good it would feel inside her.

John had seen Terry’s cock before, but it still amazed him. He watched enviously as the older man’s huge cock forced it’s way into Jennifer’s mouth, and he was grateful that whenever these situations cropped up, he always got to go first. He slammed his cock harder into the moaning girl, his palm pressed down just above her pussy, his thumb idly rubbing her clit as he fucked her.

As Jennifer continued to struggle to suck on the older man’s cock, she started to long to feel it stretching her tight pussy. John was filling her cunt quite nicely but Terry was going to be a whole different experience. She was amazed how hard he was for an old boy and wondered if he might have popped a Viagra or something similar. She’d never seen a cock so hard and she used her hand to stroke it as she licked at the bulbous tip.

Without warning John pulled his cock out of her and the two men manoeuvred Jennifer so that she was kneeling on the carpet. Terry pulled the ripped blouse off her shoulders and expertly removed her bra to leave her naked save for her stockings and the shoe that hadn’t already fallen off. John lay down in front of her and pulled her down so that she could suck his cock again, his legs spread either side of her hands and knees. Behind her Terry knelt down and pumped his cock in his fist. He edged forward and Jennifer felt the tip of his huge cock pressing at her pussy lips. She pushed backwards, eager to feel his massive cock stretching her cunt walls, but Terry pulled back and gave her arse a slap.

“Stay still,” he barked, “you’ll get it when I’m ready to give it to you!”

Jennifer moaned again and sucked harder on John’s cock, tasting her juices on his lovely, hard shaft.

“Fuck me,” she begged, “please….I want it!”

“I know you do,” said Terry, half laughing. He steadied himself against her rear and then rammed the first three or four inches inside her. Jennifer groaned into John’s groin as she felt her cunt stretch to accommodate the older man’s meat. She pushed her head down further onto John’s cock and bounced back, trying to force Terry’s meat further inside her. Terry slapped her arse again and then spread her cheeks, admiring the tight puckered hole between them. Realising what he was doing, the thought of Terry’s huge cock in her ass scared the shit out of Jennifer and she pushed back harder, desperate to bury his stalk safely inside her hot, wet cunt.

He slapped her ass again, and then again, and once again. Each time harder than the last. Jennifer screwed her face up as she pulled her mouth away from John’s cock and pounded backwards against Terry’s thick column of flesh. She had never felt anything like it in her life and she couldn’t get enough of it, her only complaint was that she rather wished that that magnificent cock was attached to the younger and more attractive man.

What Terry had in size, he perhaps lacked in stamina, he was after all pushing sixty and after a couple minutes he sped up, his fingers digging into to Jennifer’s waist as he pounded his rock hard cock into her over and over again. Jennifer’s moans became indistinct from each other and she gradually let out one continuous groan as Terry fucked her hard and fast. Then he tensed and pulled her even tighter to him, bucking wildly as he pumped his load deep into her ruined cunt.

Jennifer collapsed onto John’s chest as she felt the older man easing his cock back out of her sticky hole, and then she felt John moving beneath her, sliding his cock easily into her used, hot cunt. He felt smaller after Terry, but the angle was better and the top of his shaft stimulated her clit as she rode him.

Abruptly John pushed her backwards and caught her legs over his shoulders, he leaned through and held her arms flat to the carpet as he pummelled his cock deep into her sloppy hole. Jennifer grunted loudly each time he hammered his cock into her and then he felt her release her arms and turn her over.

John grabbed her around the waist and pulled her to him. He told her to put her head down and stick her ass in the air and Jennifer eagerly complied. She felt his tongue moving between her as cheeks, penetrating and lubricating her tight asshole as his fingers slipped into her cunt. She started to protest but John ignored her and once he had them lubricated nicely he inserted first one, then two into her tight hole. Jennifer closed her eyes and tried to relax as he invaded her asshole, his fingers wiggling wildly, stretching her ready for his thick cock.

Eventually Jennifer relaxed sufficiently and John positioned himself behind her and pressed the tip of his cock against her puckered hole.

“Push back against me,” he said as he slid his cock between her cheeks.

Jennifer did as instructed and felt the head of his cock slowly ease it’s way inside. She held her breath as the head worked it’s way in and once inside, John rested for a moment to let the girl get used to the sensation. Jennifer had almost forgotten about the other two men, who looked down on her, watching as John started to fuck her in the ass.

Jennifer reached back between her legs and fingered her cunt as John’s cock speared into her ass. She moved her fingers lower and rubbed her aching clit as she tried to get used to the sensation of John’s thick meat pounding into her tight hole. John started to move faster, the tight ring of Jennifer’s ass pushing him inexorably towards his own climax, while Mr Thomas watched on, his hand a total blur on his cock.

Mr Thomas was shaking with lust, he’d wanted to fuck Jennifer for five long years and he never thought he would get near her perfect body, never mind watch her being serviced in his office by two well hung men. Terry pushed him forward and encouraged him onto his knees in front of the girl. Seeing a knee appear beside her head Jennifer looked up expecting to see Terry’s massive cock again, instead she saw Mr Thomas’s more conventionally sized cock, but wasted no time in taking it into her mouth.

Five years of waiting was rewarded in a few short seconds as Mr Thomas erupted almost immediately, spewing ropes of cum into her mouth and throat. Jennifer swallowed every drop and licked his cock clean, she was too far gone to worry about appearances now, all she could think about was the cock pounding her ass, her aching clit and her approaching orgasm.

“Please,” begged Jennifer, “please cum, I can’t take much more.”

After a few more thrusts she felt John pull his cock out, leaving her ass feeling suddenly empty as it closed up, before she heard him groan loudly and felt several warm splashes of cum land on her back and drip off her sides onto the carpet.

John flipped the girl over onto her back and the three men looked down at her.

“Make yourself cum,” ordered John, “and then we’ll sign the fucking contract.”

Jennifer was already half way there and as she looked up at them standing over her, their cocks already beginning to stiffen again, the taste of Mr Thomas’s cum still in her mouth, John’s cum sticky on her back and Terry’s cum dripping from her well used cunt, she rubbed her clit with smooth, fast strokes until she arched her back and bucked on the floor, her orgasm massively intense and leaving her completely out of breath.

She lay still on the floor for several moments, aware of movement above her. She opened on eye and saw John leaning over the desk, his half hard cock sticking out from between his legs, the pen in his hand ready to sign the contract. She closed her eyes again and rolled onto her side. She reeked of sex, her blouse was ruined, she was exhausted and she wanted to be at home in bed, but she didn’t regret it for a moment. One thing she knew though, Mr Thomas owed her big time, and if he didn’t deliver on his promises she would make his life an absolute living hell!

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