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A Lesson in Flirtation

Category: Anal Sex
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It was a long week. Work had taken nearly everything out of Nicki. She needed a break and she needed it soon or else she was going to just crumble. It was 5:45pm and her normal day ended at 6. She could damn near feel each minute ticking away like it was an eternity. It was Friday and she intended to do some heavy partying with her friends. She had even brought her evening attire with her to work. So she wouldn’t have to stop home to change.

Nicki, Cara, and Shelly, were all the epitome of beauty. They all had responsible jobs, and were professional during the week, but when the weekend came, all barriers of decorum were thrown to the wolves. These girls were hot for some party time. She closed her eyes a minute, leaning back in her chair behind her desk. Taking a moment to recall how much fun it was to go out with the girls. They all had been friends since their college years, sisters in the same sorority. When they went out for a night on the town it was something to behold. All three of them were flirts. Major flirts. It was the one thing they all had in common, and they all had it in spades.

A small smile reached her face as Nicki recalled their last party weekend together. They had all been out to their favorite nightclub, Visions. It was one of the hottest places for nightlife and it was huge. A large dance floor and bar on each level of the 3 floored establishment. Each floor had a different ‘Theme’ to it, and patrons could choose their pleasure for the evening. Nicki and her friends often opted for flirtier atmosphere of the top floor. It suited their tastes perfectly, with plenty of ‘hidden’ corners, and cubical where customers could go to get to know each other better, not to mention the highlight of that particular level. The clear dance floor. Nicki, Shelly, and Cara absolutely loved to dance, next to flirting it was their favorite pastime. The clear glass dance floor offered the girls a chance to do both at the same time. For you see, it gave the patrons upon the middle floor a perfect view if only they were to look up. The glass floor was provided as sort of a voyeur’s aide to those below.

Nicki recalled with a smirk on her face the last time her and Cara danced upon that floor. It was a few weeks ago and Shelly couldn’t make it that night. They had both observed the ‘crowd’ on the second floor as they headed up, and Nicki had instinctively locked her eyes upon one man in particular. He was nursing a beer and causally glancing up towards the clear dance floor. He wasn’t leering and making outlandish comments like the others around him were, yet it was obvious he was enjoying the view. Dressed in simple faded jeans, and a warm flannel shirt, he looked more like he belonged on some farm somewhere instead of in this rather progressive nightclub. The man was hot. Totally. Nicki set her sites on showing this ‘cowboy’ just what city life could be like. She confessed her interest to Cara and both women chuckled. This was going to be an interesting night.

Nicki didn’t waste much time when they reached the top of the stairs; she didn’t want her target for the night leaving before she had time to gain his attention. She ordered a shot from the bartender to loosen her up a bit, downed it, and headed towards the dance floor. Her black leather mini having been the perfect choice for this evenings entertainment. She began a series of dance moves, that she was quite comfortable with, as was the growing crowed of men about her and Cara. They were both regulars at Visions and the guys knew that they were in for a visual treat when these ladies came to play. The dance, while entertaining to the men on the third floor, was intentionally designed to offer those below, on the second floor, one hell of a view. Nicki giggled softly to herself, as one of the men snatched Cara away for a more ‘private’ dance inside one of the walls of an empty nearby cubicle. She continued her dance, allowing some of the guys to dance with her, yet never committing to any one in particular for very long. She knew that those down stairs were getting view after view of her long muscled legs, that led up to her panties. The thought made her hot. The only thing that would make her hotter was if that ‘cowboy’ was still there. Nicki chanced a glance down, very cautiously. Not wanting any to know that she was really dancing just for one in particular. Damn! He was gone.

Opening her eyes from her memory she glanced at the clock again. It was 6pm and time for her to get out of here. She quickly signed off her computer, cleared off her desk and rang her answering service. She headed out of her office, her large plastic shopping bag in hand, and after saying goodnight to her secretary she quickly darted into the ladies room across the hall, locking the door. In a matter of moments, she stepped in front of the full length mirror the normally straight laced, tailored suit wearing, highly respected executive Nicole Jameson, had been replaced by this tall, slim, exotic looking party girl wearing a low cut red shimmering spaghetti strap tank top, and short thigh length flowing black skirt. Set off with just the right jewelry and high heeled black leather boots. She looked as though she was 20, in college, and ready for a night of heavy partying. “Hello Nicky!” she mused to herself as she added the final touch of a deep soft lipstick. She may like to flirt, but she was defiantly no slut. The gauche red lipsticks women wore now a days just screamed “take me”. Nicki was defiantly more subtle.

Tossing her long tailored business coat over her, she unlocks the door to the ladies room. She shouldn’t encounter anyone at this hour but one never knows. Her coat hid her new attire nicely. Walking quickly down the deserted hall of executive offices she quickly passed that of her boss without glancing up. Mr. Preston had been pushing her hard this past week, piling up work on her like it was a punishment, and she had no interest in letting him know she was leaving. He was a taskmaster and likely would wonder why she wasn’t putting in a full shifts overtime if he caught her. Quickly pushing the button to the elevator, Nicki glanced nervously around as she waited. She was almost there, just as soon as she stepped into the elevator and those doors closed. Forty-five minutes later, a very excitable Nicki reached for the door of Visions. She was here finally, she made it. The girls had to work late and had agreed to meet her here as soon as they could. Stopping in the ladies room again, Nicki quickly shed the remains of her business life in one quick flourish. Off came the floor length coat, and out came the pins that held her long brown hair securely in what was a most proper business style on top of her head. Quickly scrunching up a bit of her shiny waist length hair to give it that ‘wild’ look she steps back and nods to herself in approval. The tank top set off her ample chest nicely, and the short black ‘skating’ type skirt would provide just the right amount of teasing, should any gentleman catch her eye. Oh, this was going to be a night to remember.

Turning she stepped out on to the first floor of Visions. She headed straight for the stairs and paused midstride as she acesended to the second floor, her brown eyes instinctively glancing over towards the men at the bar, checking to see by some miracle if her ‘cowboy’ was there again. Of course he was not. A bit disappointed, she continued up to the third floor, and her normal table.

(Part 2) Nicki went straight to the bar and ordered a shot, then returned to her table. She sipped the first one, glancing about the smoke filled, dark atmosphere, and awaited the arrival of her friends. Half an hour and 3 more shots later, Nicki decided to get up and dance a bit. To help pass the time. The music was beginning to call to her, and the drinks had only intensified that effect. She headed out to the dance floor, and began to dance. Her body moving to the fast paced beat of the song like it was effortless. Once again, quite a crowd of men had gathered to partake in the ‘eye candy’ and Nicki was loving every minute of it. Teasing each one in turn with a twirl of her neck, or a spin of her hips. After the song ended, she turned to head back to her table when the slow, seductive, heavy beat of a song began to thrust from the speakers. The base hit its mark, matching the beat in her rapidly increasing pulse rate. The eerie, mysterious rhythm making her long to do more then just dance..

The grip about her waist broached no room for argument. Fingers tightening about her and pulling her quickly backwards against a strong chest. Those very same fingers holding her there in a firm, no nonsense manor. Nicki gasped a bit as her body melted into that of this mystery man. She couldn’t turn about, yet she could tell it was a man from his purely male scent, and the way he held her. He kept up the seductive dance in time with the music, and even pulled Nicki harder against himself as he whispered in her ear: “Lets dance shall we precious” Her body began to move in conjunction with his, fluid and smooth to the lustful beat of the music. He obviously knew the art of seduction in dance, and he was making sure she felt it. Oh, how she felt it. Her back pressed against his rock hard chest, his hands splayed across her hips, he guided her to mirror his bodies’ movements to perfection. Not an inch was in between them, and Nicki felt every contour, every muscle, every movement like it was her own. This man knew her to well. The dance spoke volumes, and the fact that he was a perfect stranger excited her even more.

“You like this don’t you” Damn he read her thoughts, and spoke them in a husky tone right next to her ear again. This was proving to be too much. Nicki began to throw a few moves of her own. While his hands held her fast to him, she still had ample room to rotate her hips in an unmistakable fashion. The fact that it caused her ass to rub seductively against his manhood wasn’t her fault. After all he was the one holding her to him wasn’t he? The reaction she received wasn’t exactly what she had expected. Oh yes, she heard the quick intake of breath, felt him grip her hips a bit harder, even dare say that she heard a low soft groan escape him, but what really got to her was the quickness of his movement, when his hand left her side and replaced itself once with a sharp stinging slap to her ass, and then returned to its former position.

“Ouch” she hissed low, her body still being held against his tight. The dance continuing, and no one about them any wiser for his actions. “Nice try precious” he hissed in her ear. The dance continued and Nicki felt herself getting more and more aroused by the moment. This mystery man had a way about him that drove her absolutely crazy. He wouldn’t let her turn about and see his face, yet his hands wandered over her body as though familiar, and very, very possessive. The sensual dance beat slowly died off, and Nicki thought she would make a quick break for it and tried to turn about quickly to see whom her mystery captor was. She was jerked quickly back with those firm hands once again, pressed up against his body. She was quite helpless at this point, but if she thought this was bad, it was nothing to the feelings being stirred in her as his one hand went from her waist, to her hem line, and slowly caressed their way up her bare thigh, touching the most intimate parts of her with but his fingertips.

Her gasp was audible, and her body felt chills running in a million directions. Anyone looking up from below would obviously have a perfect view of his fingers on her. That thought alone was quite erotic to her. He led her slowly off the dance floor, still semi keeping within the beat of the music. Before she could protest he had her ‘danced’ into one of the corner cubicles, and had locked the door behind him. In a matter of a moment Nicki felt herself sandwiched between the soft padded wall, and the hard muscled one that was his chest. “Such a flirt precious” the words hot against her ear again. “Time to teach you what happens when I get aroused” Inside the small cubical, the lights out, and pressed against the wall like this; Nicki had little alternative other then to submit to this mans whims. At least for the moment. His one hand held both of hers pinned behind her back, and once again his right hand reached down and lifted the hemline of her skirt away from her ass. He tucked the hemline in her waistband, leaving her exposed ass out for his perusal. He didn’t release the pressure he was exerting against her body and the wall either. His fingers moved slowly, exquisitely slow as they trailed up her bare thigh again, this time instead of caressing her now swollen lips, he moved them to her ass.

Up and down he stroked her there. Slowly. In the next moment Nicki felt a flourish of movement, which ended up with her over his knee, her bare ass up in the air, and at his whim. “Beautiful” he muttered as he caressed her two perfectly shaped cheeks. It must have been a slip up on his part, because in the next moment there was no tenderness in his words. “Its time to learn what happens to little flirts Nicki” the voice still low and husky. “You now must face what happens when I get aroused due to your little game of flirtation. I intend to make sure you realize just how painful it can be for me to watch you dance about and tease all those men. Your going to learn the hard way, and its going to start now” without a moment’s notice his hand began descending across her snow white ass in heavy SMACKS that left an echo in the room. 5 on one cheek, then another 5 on the other. Pausing after the first 10 to rub the now pink cheeks. “Ouch, shit, that fucking hurts damnit” Nicki all but screamed as they descended upon her bare ass. She tried in vain to wiggle out of his grasp, but only found herself held tighter.

“They are supposed to hurt Nicki, I’m giving you the same pain I get when I see you flirt with other men. When I get aroused and have no where to vent my problem, all because you wish to be a little hussy that evening. Prepare yourself precious for they’ve only just begun” At those words another 10 swats were delivered all over her bare ass. From top to bottom, side to side. The redness now was beginning to form an even color over her ass. Nicki continued to squirm and cry, though she couldn’t move at all. He was in full control, and he was going to give her what he felt was equal punishment for what he had to endure watching her. The spanking really hurt like hell, but Nicki was also beginning to feel something else. A moment later she realized what it was. The spanking she was receiving was making her wet. It was turning her on. She shook her head in pain and disbelief as her mystery man continued with his lecture and her punishment.

“You have been a very naughty young woman Nicki” -Smack, Smack, Smack, Smack- “I’m going to have to teach you what it feels like to be properly punished. I don’t like to be aroused and then not be able to screw you properly. You deserve every swat your getting, and I suggest you just take it like a woman” -Smack, Smack, Smack- was this man really talking to her like this? Did he know how long she wanted to be treated like this, talked to like this, be given what she rightfully deserved like this? “Ouch, Please stop, please” she pleaded, but something in her voice must have given her away, for he stopped immediately, and while he again rubbed with one hand, his other hand went down and stroked her pussy. “Ah, I see you are enjoying this precious, your getting all wet” came the silky smooth voice. SMACK, SMACK, SMACK,SMACK,SMACK- Came 5 more in rapid succession. “This is NOT to be a pleasurable experience for you” with those words Nicki felt him bend down and reach for something on the floor. His next words were punctuated with something that she will never forget.

“Your going to have to learn the hard way I see precious” He spoke matter-of-fact as he inserted the full length of the 7-inch toy inside her dripping pussy. Nicki almost had an orgasm right there. “Ohhhhh shit” came her low moan He began to slowly thrust it in and out a few times, getting her quite excited, she was actually bucking back against him when he suddenly stuffed the full length back inside her, all the way up to the base, and quickly resumed spanking her ass again. “Its not red enough precious, I don’t think you’ve learned your lesson yet” He altered his spanks so she wouldn’t have any permanent damage, yet made sure they were hard enough to cause her to damn near jump off his lap. He wanted her repentant for the discomfort she caused him this evening. He was going to make sure she knew how it felt. After somewhere around 20 swats on her bottom, he paused and rubbed again. Nicki was beyond herself with the pleasure and pain. The toy shoved into her pussy was vibrating so quickie that she thought she was going to orgasm right there, yet the pain of his spanking was keeping her from going over that edge. She was so close. So close, and he knew it. A low chuckle echo’s off the walls softly. “Yes precious, you are so close aren’t you, you want that blessed relief. But you also know that this is what I experience when you arouse me, and I have no outlet for it, why should you hmmm?” Nicki only moaned, she knew he was torturing her. However his next move was executed so quickly she thought she was going to fall. Before she could utter a word, she found herself on her hands and knees upon the floor. He forced her legs to spread wide, and he was shoving the toy in out of her, alternating between fast and painfully slow.

Once again a few smacks landed their way on her ass, and then the toy was once again shoved in deep and left there. Suddenly she felt the cheeks of her ass being pulled apart:: His tongue ran from the tip of her ass down to her pussy and back up. Slowly tormenting the girl. He held her wide open with one strong hand, and with the other unzipped his pants. Nicki heard that and her blood went cold. He was planning to:: “Oh dear god no” came her almost desperate response. Not there please. “Its time I finally satisfied myself precious, and to push all 8 inches of my cock into that hot, tight, little rosebud of an ass of yours, is going to give me great pleasure” Nicki shuddered. “Oh I expect its going to hurt” he continued, obviously unaffected by her reaction. “I expect your going to feel each and every inch as it slowly penetrates your ass and opens you up. It will probably burn like fire at first, but then again, I want you to remember what it feels like so you will learn your lesson”

Nicki braced herself the best she could against the wall. She knew this was going to be rough, and truth be told, she was desperately anticipating it. She wanted this man to take her ever since they began that dance over an hour ago, and it was finally going to happen. She was going to be taught the lesson she so richly deserved. Her mystery man continued to stroke her ass. Telling her in no uncertain terms just what he intended to do and why. “I’ve wanted you in this position for some time now precious” his husky voice continued. “Bent over on all fours in front of me, your pussy spread open by a 7 inch plastic cock, and your ass laying exposed in front me, just begging for me to tend to it properly. Oh, I am so going to enjoy this.” “You know I have to teach you precious, you know I have to show you the error of your ways don’t you?”

Nicki was jolted out of her thoughts by several hard smacks to the lower part of her ass. Obviously he didn’t take well to being ignored. “Y-yes, I know” came the shaky reply. Apparently that was all he needed to hear because a moment later the only sound that filled the room was that of Nicki’s emphatic groan. “Ohhhhh yessssss” His cock pressed into her ass in a steady motion. It stretched wide to accommodate him and Nicki felt every inch of it. “Ahhhh god, oh yesss, it hurts” the words poured in a low rasp from her lips. His hand reached around and rubbed her pussy gently as he continued to hammer into her ass. He couldn’t believe the sensations his body was receiving. This beauty in front of him with a dildo stuck in her pussy and his cock in her ass drilling away, she looked so obscene and was begging him in her own way to continue. Well, he had no intentions of stopping that was for damn sure.

Nicki held her eyes closed tight as her ass was assaulted. The pain was intense at times, especially considering her well spanked ass was being thrust into over and over, but the sensations of pleasure were overwhelming. Between the hard toy in her pussy vibrating at an all time speed, and his hand rubbing her clit, not to mention his cock hammering into her ass, and his hot talk, she was feeling so full, she was damn near an earth shattering orgasm herself. “Tell me why precious” his voice punctuated by each hard thrust into her ass. “Tell me why your on all fours with a well spanked bottom and a toy in your pussy.” “Ohhhhh, because I’m such a bad girl, I’m such a flirt” Nicki ground out the words in between moans of pleasure, he was pounding her harder now, and it was getting harder to think straight. “Yes precious, your such a flirt, and what else, why are you getting your tight little ass fucked with my hard cock?” his voice becoming a bit faster now.

“Because,:: “AHHH YES”:: because, I made your cock hard with my teasing and, ::OHHH SHIT YESSS”:: you now have to teach me a lesson with it” Nicki began to thrust herself back on him, now beyond caring what his reasoning’s were, the only goal in her mind was to reach orgasm. She was so close. He continued his assault on her ass, now both hands replaced on her hips and he pushed and pulled her to his pleasure. Watching his hard cock slip in and out of her tight ass was almost as much pleasure as feeling it. She was moaning loudly beneath him now, and he knew he wouldn’t be able to hold back much longer. He drew back and landed a few more slaps to her ass, only these were a bit more playful then pain. He had no doubt they still stung though, as her ass was still a delicious shade of red. Nicki dug her fingers into the carpet as she felt her orgasm begin to take over after those last swats. The combination of the vibrating cock in her pussy and his real cock in her ass had finally sent her over the edge. “Ohh-my-goddddd” came her low guttural groan as her whole body convulsed and every muscle in her body tightened up. “Fuck-my-ass-NOW” as a scream of release passed thru her lips.”

His cock seemed to go even deeper as he heard her. Those filthy words coming from her mouth effectively pushing him over his brink as well. He buried himself deep in her ass and filled her to the brim with what seemed like gallons of cum.

Monday morning Nicki walked the long hallway down to her office. She passed her boss’s office quickly and reached a hand out to her secretary as the woman handed Nicki her mail in one hand and a cup of coffee in the other. “Thanks Sherry” replied Nicki, and headed into her office. Setting down the coffee and purse on the desk, Nicki rifled thru the content of her mail. She remained standing for the moment, as sitting would still be a bit on the “sore” side. One particular envelope caught her eye as it was simply addressed to Miss Jameson. No return address, and it looked interoffice instead of regular post. Turning it over in her hand and still seeing no tell tale signs of whom it was from, Nicki reached for her letter opener and carefully ripped it open. Inside was only a simple piece of paper, typed from some kind of expensive printer. Nicki opened it and despite her sore bottom, fell down into her desk chair with a smirk upon her face as she read::

Precious, Next time maybe you wont sneak past my office without saying goodnight. Same time and place next week? Wear something decent, you know what happens when you tease. -Your Cowboy-

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