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Anal Annie
By
Jonathans_Fantasies

Anal Annie

She give him a well deserved break from work!
Annie was not having a good day. It all began when her alarm clock didn't go off when it was supposed to. Luckily she woke up on her own, albeit 30 minutes late. So she had to hit the ground running and scramble to get ready for work. Running behind her already tight schedule, she quickly dressed in the first thing she could grab from her closet and threw it on. Then putting on her nylons, she got a run in one of them! Great! She took them off and put on another pair and then slipped on her heels. She was finally dressed, and she put on her makeup and grabbed her purse and headed for the door.

Opening the door brought another surprise - it was raining! Annie heaved a heavy sigh, and grabbed her umbrella. This was going to be a long day! She made it to the car and started off to work. She made it to work without much more trouble, and rushed into the office, explaining to her boss why she was late. Her boss wasn't any too pleased, but chewing her out wouldn't get her work done any faster, so he just told her to get busy.

Lunchtime brought another setback. She wanted to grab a quick bite to eat so she could work through her lunch and get caught up, but as she stood in line at the cafeteria, she realized that she didn't have her credit card with her! And she only had a couple bucks in cash in her wallet. So she went to the vending machine, and got a candy bar and a bag of chips. That and a cup of coffee, would have to serve as lunch! And without breakfast that morning, the afternoon was going to be a hungry one! She made it through the work day somehow, and then tired from the stressful day, she headed for home.

She was looking forward to this evening, though. She had a date with her new beau, Brad. She had met him through a girlfriend who works in the same office, but a different department. She had introduced Brad to Annie a couple of months after her 23rd birthday, and they had been dating for about three months now. Brad was a five years older than her, and while Annie had led a pretty quiet dating life, Brad was more outgoing and social. He was everything Annie had wanted in a man at the time; successful, handsome, great in bed and open to just about anything when it came to sex.

But fate would throw yet another monkey wrench into her plans. On the way home from work that afternoon, her car died! She had been meaning to take care of that "check engine" light but was going to wait until the first of the month when she got paid. Unfortunately, the car ran out of patience before that! So fishing her cell phone out of her purse, she called the auto club service number and they sent a tow truck to bring her car to the repair shop. From there she got a cab to take her home. Finally! She was home!

Now she had 20 minutes to get ready for her date with Brad and she had no idea what to wear! She wanted this night to be special... they been taking it slow and getting to know each other better, but she was hoping tonight to change that. Annie dug out her favorite black dress - the skin-tight one that looks like it was painted on! It was a plunging halter top that showed off her full, firm 36D tits nicely and made Brad ogle her she the way she liked. She was a flirt and a tease, loving the way she could make a man drool after her. And she planned on making Brad salivate tonight! She wriggled her way into the dress and was just slipping on her killer heels when...

Damn, was that her phone? Annie raced downstairs to the kitchen where the phone was, but the message light was blinking, she had missed the call. She played the answering machine message hoping that whoever it was at least left a message. As the voice on the machine began, she knew instantly who it was. It was Brad, he had to cancel their date, he couldn't get away from the office. "FUCK!" Annie thought as she hung up. So much for her night of fun!

She went back upstairs and got undressed. No need for her hot dress tonight. But as she got undressed and was putting her dress back in the closet, she began feeling guilty. Brad had been working so much lately. He had told her that his boss was putting a lot of pressure on him to get this one big sales program finished. Poor Brad had hardly had time for dinner much less a dinner date! That's when Annie had an inspiration and knew just what she could do to solve both of their problems! She headed for the shower, smiling and humming under her breath as she formulated her big plans in her head.

Annie was excited as she got out of the cab in front of Brad's office. She went over her plan and just what she wanted to say to him as she rode the elevator up to the third floor. The ding as it reached her floor startled her out of her daydream. She was here. As she stepped out of the elevator, she heard the faint sounds of a radio coming from the back. Since the rest of the office seemed empty, she figured that must be him. Nervous now, she hoped he wouldn't be upset with her just showing up like this. She had never visited him at work and didn't know how he would take it, to be truthful. But she was here so she might as well go through with it now.

As she walked down the hallway, she found the office the music was coming from, peering around the corner, she saw him. His feet were up on his desk and he was reading some papers. He didn't see her come in and the carpeted floor didn't give her away either.

"AHEM," he looked up and seemed startled to see her standing there.

"Annie, didn't you get my message? I really need to stay here and get some work done," he said, as he got up and came towards her.

She smiled, "I know, but you sounded kind of stressed out and I figured you wouldn't even stop for dinner, so I thought I would stop by and see if you had five minutes for a break. Aren't you happy to see me?"

"Of course I am, honey. I'm always happy to see you. Do you want to go sit outside?"

"No, I don't think so Brad," she said, as she opened her raincoat and let it slip down her arms. She couldn't help but smile at the look on his face as she stood there in her heels, stockings, and her sexy new (and very tiny) thong panty.

"HOLY SHIT!" he exclaimed.

Annie walked over and kissed him and he hesitated a moment before kissing her back, still trying to wrap his mind around what was happening. He wrapped his hands slowly around her waist and pulled her in closer. Annie deepened her kiss as she felt his hands on her bare skin, opening her soft lips and inviting his tongue to come play with hers. Annie reached up and ran her fingers through his hair grabbing hold of his collar-length black locks, pulling him closer as she rubbed her naked tits against his silk shirt. The sensations sent little electric sparks through her stiff nipples and she mewed softly. Brad leaned down and put his hot mouth on her neck and shoulders, biting her softly, and her head fell back to give him more access to her soft throat.

Annie began pulling his hair as her passion fires were ignited and her pussy, already moist from the anticipation of this encounter, became soaked. Her hands trembling, she fumbled with the buttons on his shirt, wanting so much to just rip it open and devour him. But she knew that his shirt was expensive and took care not to damage it. He stopped kissing her and unbuttoned the shirt himself, as Annie reached inside and ran her hands across his chest and down his belly. Brad groaned, and quickly unbuckled his pants and dropped them to the floor around his ankles. Annie lowered herself down his body, kissing him softly as she did. Upon reaching his boxers, she pulled them down slowly, teasingly, and Brad groaned again.

Released now from its cotton prison, his hard cock sprang up, rigid and pulsing before her waiting mouth and she smiled as she kissed the tip. Brad gasped as Annie took his hardness into her mouth, sheathing her teeth behind her lips and sliding halfway down his length. She twirled her tongue around the cock and soaked him in her spit. Annie pulled back to his tip and slid down again trying to go a little farther this time. But between his length and girth, she couldn't get far. Annie pulled back again, this time completely out of her mouth, and looked in awe at his amazing package and then looked up at him. He looked down and smiled at her and she leaned forward to resume her task. She ran her soft tongue down the length of him, tasting his muskiness and sweat. Shivers ran down her spine.

She looked back up as she was sucking on him and he watched her with a half-smile. He pulled out of her mouth and lifted her back to her feet. He kissed her deeply, his tongue engaging hers in battle like two snakes wrestling. Suddenly she broke the kiss and with a seductive little smile she took him by the necktie and turning with the tie over her shoulder, she led Brad across the room to the desk. She turned to face him again and backed up to the desk, hopping up on it, and sitting there with her legs spread wide. Annie felt the cool hardness of the desktop against her ass and she sat back, inviting him closer. She looked at him longingly, and he leaned in and kissed her again, grinding his hardness into her panties. His hands reached up and cupped her large tits and he fingered her stiff aching nipples, causing her to moan softly.

He ran his thumbs over and around her nipples which instantly hardened and poked out needing more. He leaned in and took one then the other into his mouth and gently bit them. Annie heard herself groan as he sucked on her nipples harder, her panties now completely soaked.

"Shit, Sweetheart!" he said as he picked her up and carried her across the hall to the break room and over to an old couch in the corner. He laid her down and again kissed her deeply and passionately. His head moved down her body, his hot breath making her nipples ache, his kisses leaving a trail of fire across her body.

"Please Brad," Annie whined softly. He released her nipple and looked up at her. Annie squirmed, trying to get him closer, wanting to feel him inside her. But instead, he stood up and reached for her legs and ran his hands up her legs to the tops of her stockings. Annie groaned as he stopped there, just a few tantalizing inches away from her steaming pussy. Brad smiled and reached up, grabbing her panties and pulled them slowly down her legs and off of her, repaying her for the teasing she gave him a few minutes earlier. Brad spread her legs and knelt between them, dipping his head down to her hot mound and inhales.

"OH GOD BABY," he moaned as he placed his hot mouth over her dewy lips, his tongue parting them before slipping deep inside her honey hole. Annie gasped and arched her back as he began tonguing her, running his tongue up and down her wet slit. He flicked the tip of his tongue over her engorged and aching clit, sending a jolt of electricity up her spine to mix with the other sensations crowding and fighting for supremacy in her tortured mind.

"OHHHHHH," Annie said as her orgasm began to build deep in her belly. Brad's tongue continued to tease her and she added to his ministrations by reaching up and grabbing her bounteous tits, pinching and pulling and tugging at her nipples, and digging her fingers deep into the soft fleshy globes.

Having had his fill of her sweet nectar for now, Brad's cock demanded similar satisfaction. So raising up, he grabed both of Annie's widespread ankles and brought them high in the air, holding them there as his cock closed the distance to her sopping slit. He moved closer until the tip of his cock was about an inch away from her hungry pussy and stopped. He ran the tip of his cock up and down her slit, parting her lips slightly and teasing her all the more. He teased her with his cock, rubbing it over her clit and then pushing forward until she could feel it at the very entrance of her pussy.

"OHHH BRAD, PLEEASE!" Annie whimpered, "Please fuck me! Fuck me now!"

Brad gathered himself and drove his steel-hard cock deep into her in one thrust. Annie gasped as his rod filled her to capacity and quickly felt herself matching his hard pace. He drove into her like a raging bull, but it still wasn't enough for her. Annie wanted more, she wanted all of him. She clawed at his hips, trying to pull him in deeper, faster, harder. He rolled over while still inside her until he was sitting on the couch with her astride him in the "cowboy position".

Annie sat on Brad's lap rocking her hips forward in a slow rhythmic grind, pulling his cock out until just the head remained inside her opening and then rocking forward, sliding back down his pole till he bottomed out inside her. She rocked back and forth, sawing on his cock as her orgasm climbed to the crest. As Annie rocked her way to ecstasy, Brad busied himself with Annie's bouncing 36D's, grabbing handfuls of the soft flesh, tugging and pinching her nipples and slapping her tits as Annie neared her crest.

"OOOHGODDD, I'M CUUMMINNNGG!!" Annie wailed as she plunged over the precipice. As she began cumming, Brad added to her experience by pinching and pulling her thick nipples hard, the mixture of pain and pleasure driving her even deeper into her abyss.

Annie grabbed his wrists and hung on tightly as she tossed her head back in bliss as the waves of her orgasm washed her away. Annie's legs trembled and quaked as she sat astride Brad, mewling and whimpering as she came hard and felt her juices escape past his punishing tool and soak them both. He pulled her down to him and kissed her but continued pounding her pussy even as she came on his cock. Annie wrapped her arms around him and clung tightly to her man, riding him for all she was worth. He took her punished nipple into his mouth and bit down as he groaned loudly. With a final thrust he impaled her, holding himself deep inside her as he added his own white hot cum to hers, mixing the two in her pussy before it leaked out around his rigid, pulsing member.

Annie collapsed on his chest but realized he hadn't softened and was just as hard as ever. She climbed off and he helped her to stand on very wobbly legs. Walking her across the break room to the dining table there, he bent her over the edge and placed her elbows on the table as he lifted her ass and slid into her dripping pussy. His pace was slower now, and Annie felt his mouth kissing her neck and shoulders as his hands came around her body. He reached one hand up to maul a tit, his other hand snaked its way down and had clamped onto her drenched mound, pushing on her clit as he began thrusting harder. His fingers ran across her smooth pussy and probed into her lips, teasing her clit and building another orgasm higher and higher until she exploded on his hand. He spread her ass cheeks and teased her tight hole as he continued stroking deep while her orgasm rocked her whole body.

"I'm sorry baby, I'll make love to you later. Right now, I need this," he said as he pulled out of Annie's pussy and spread her ass cheeks. She felt him spit on her asshole and finger it some before pushing in. Anal sex was something Annie never thought she would ever do, but she always secretly wondered what it would be like though. Now here she was bent over a table in an office building break room, with her naked ass spread and a man about to enter her asshole for the first time.

"Please be gentle Brad... I... I'm a virgin there," she said, looking back at him.

"It's ok, sweetheart, I will be easy," he said, kissing her on the back. Then he knelt down behind her, locked his arms around her thighs and looked up at her. He leaned in and began lapping away at her ass hole. Annie tried to wiggle from him but it was useless. Between the torturous lashes of his tongue, he breathed "pull your ass cheeks apart," and she did just that. Feeling him circle his tongue over her puckered ass hole, and him sticking his tongue in and out of her ass. Annie couldn't believe how much she was enjoying this taboo torture.

He then gently slid his little finger in her ass and fucked it, slowly at first, then a little harder. Then he used his middle finger and did the same, soon he had 2 fingers in her ass and she was enjoying every bit of it. Though she hadn't come yet, Annie was having the time of her life. He used his fingers to get her opened up and ready for him. Annie felt his fingers probing her anus and she marveled at the feeling coming from her backside.

"Ohhhh Braaad," she cooed. She lifted herself up on her toes and pushed back against his finger, wanting more. Brad began twisting his hand to the right and to the left, getting her asshole used to the size. He spit into her ass again to lubricate her as he worked to open her more.

Once he felt she was ready, he pulled his fingers out and rubbed the head of his cock along her pussy slit lubing his cock with her own juices. Putting the tip against her asshole he got ready to enter her ass for the first time.

"Oh, baby, here we go. I will take it slow so just relax that beautiful ass," he said reassuring her.

Brad began gently pushing into her. Annie felt him poking his cock at her ass and then she felt her asshole begin to open for him.

"Ohhhh, ooooh," Annie whimpered as she felt her asshole opening to accept him. Brad pushed into her slowly, letting her ass open and he pushed until his cock head popped past her sphincter. He stopped at that point to let her get used to his size. Brad wasn't huge, but his cock was bigger than average and he didn't want to hurt her. When he was satisfied she was ready to continue, he again eased further into her. Annie laid her head down on the table and moaned as he pressed into her.

"Ohhh God! Brad It's too big!" she cried as she felt her ass being split open.

"It's ok, Annie you are doing fine," he reassured her.

"How much more? I don't think I can take it!" she said.

"We're almost there, just another couple of inches," he told her.

"No! oh please! I can't!" she complained.

"There! I'm completely in," Brad said finally.

"You're completely in?" Annie asked.

"Yep, that's all of me," he confirmed. He stayed still for a few moments to let Annie's ass get used to the invader.

"Ohhhh Brad! I feel soo full!" she said, liking the sensation of his cock in her ass. He steadied himself before grabbing her hips and pulling back out his entire length and plunging in again. Annie panted on the table as he sped up, taking pleasure from her tight ass as her mound rubbed against the edge of the table, bringing her closer to another wave of pleasure. Her hips were being beaten into the desk but she hardly noticed as she felt him piston in and out, her own orgasm exploding across her body as he let out a yell and pulled out cumming across her ass and back and droplets hitting the office chair.

"Ohhh baby, I'm sorry!"

"God no, that was amazing. Hope you didn't mind the break," Annie giggled.

"Sweetheart you can give me this kind of break anytime!" he said with a smile.

She allowed Brad to have her ass anytime he wanted it after that. He had given her a wonderful experience and she had become a fan of anal sex. Brad enjoyed taking Annie from behind just as much and would call her his "Anal Annie", a nickname that always made her smile!

The above story is a work of fiction. The names, characters, places and events in it are products of the author’s imagination and are used as fantasy. Any resemblance to actual events or persons, living or dead, is entirely coincidental.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com with this note attached, it has been posted without my permission.

Copyright © © Copyright 2013-2015 by Jonathans_Fantasies
All rights reserved, including all copyrights and all other intellectual property rights in the contents hereof.

The compositions and contents herein are not to be copied, reproduced, printed, published, posted, displayed, incorporated, stored in or scanned into a retrieval system or database, transmitted, broadcast, bartered or sold, in whole or in part without the prior express written permission of the sole author. Unauthorized duplication is strictly prohibited and is an infringement of National and International Copyright laws.

All names, characters, businesses, places, events and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters portrayed in this story are over sixteen (16) years of age.

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