Anal Annie
by Master Jonathan
Copyright© 2021 by Master Jonathan
Erotica Sex Story: Annie was all set for her date with her beau until he called saying he had to work late. Disappointed but not deterred, she decides that if he can't come to see her, she'd bring the party to him!
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual Fiction Workplace Anal Sex Analingus Masturbation .
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!
She looked in her purse to find 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 looked 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 the way she liked.
She was a hopeless 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 and 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 and her panties were now completely soaked.
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