The Ass Game

She liked what she saw. A lot. There wasn't a man on the planet who wouldn't.

Kathy smiled at her reflection knowing that compliance with his wishes would no doubt have consequences. Consequences that if she were honest with herself, she was eager to explore. Besides, she never could resist that little "naughty girl" voice in her head that, especially since her separation, seemed to say, "go ahead, girl, push your luck." That voice had usually got her into plenty of trouble. Wriggling the skirt down over her hips, she bent forward, exposing her ass to the mirror, checking just how far she'd have to go to "push her luck".

Not very far. Her ass cheeks and labia were only a few inches above the hem.

She dripped on the drive to the restaurant like an overflowing roof drain. "It's a good thing both my skirt and the upholstery are black," she thought pulling into the parking lot of the fancy Italian restaurant while checking her make-up in the rear view mirror for the umpteenth time. "My honey pot feels like a rain forest."

The college-aged boy who was serving as the valet captain was the first to see her glistening pussy tonight as Kathy swung her long legs from the car, smiling coquettishly at the young man who was perhaps thirty years her junior. He wouldn't be the last.

"Mmmm, yummy," she mused to herself, winking at the boy while taking a second lingering glance at the bulge in his black trousers. "Mommy would take YOU for a long drive, baby," she thought. Damn, she was horny. She was literally salivating to suck a cock as soon as possible.

The handsome maitre'd, a slim Mediterranean man in his sixties , similarly hadn't been able to keep his eyes off her and for a moment, she wondered if perhaps she should have worn a coat. It was too hot and too late for that now as Kathy stood waiting in the foyer, taking a deep breath and nervously smoothing her skirt down for the twentieth time.

"Ah, yes, Kathryn, we've been expecting you. You look radiant. Your gentleman friend is waiting at the bar for you." The older man's eyes were knowing, and they bore into her twinkling green eyes, the color of a Caribbean ocean in sunlight.

He was classy enough not to ogle her as he graciously waved his hand in the direction of the plush bar, bowing dramatically as she walked past. Which strategically gave him an eye-level view of her scrumptious backside as she passed just a few feet away. He emitted a low wolf whistle to himself. "Sex on a stick," he mumbled to himself. "What a piece of ass. I love my job."

When she saw John at the almost deserted bar, another trickle of moisture eased down her inner thighs. He looked dashing, though unshaven, a five-o-clock shadow which accentuated his classic jaw line. He wore a blue sports jacket and an open-collared white shirt. Understated, but delicious, like one of those L.L. Bean middle-aged-men catalog models that Kathy regularly masturbated to, one of her dark little secrets. Those catalog models could make her cum more than any hung porn star.

John spent, what felt to Kathy, several long minutes inspecting her. Blatantly and openly looking her up and down. His eyes wandering from her face, pausing for a moment at her full breasts, the tantalizing cleavage, down lower, taking in the trim waist, the short skirt and the long, long legs to where the thin black straps of her high heels wrapped around her slim ankles. She stood a little defiantly, one hand on her hip, almost as if challenging him to find fault with her.

"You look lovely, Kathryn, just lovely," he said smiling, nodding his approval. His eyes traveled lower, to her feet, "Great shoes," he grinned at her, like an upperclassman frat boy with a naive freshman coed.

Lovely and sophisticatedly slutty, or sluttily sophisticated...but, oh, so, completely edible, was what he really wanted to tell her. It would be a pleasure to have her ass for dessert.

And he would go back for seconds. John was ravenous for her ass. Kathy was as of yet unaware that she had finally met a man whose sexual appetite and erotic imagination for all things anal matched her own.

Struggling to not betray his waning composure, he said, "This is my favorite Valpolicella. I've taken the liberty of ordering a bottle for us." He handed her a glass.

Kathy felt torn between being flattered at his compliments and somehow a little disappointed and deflated by his seemingly casual observation of her. He'd made such a grand deal of her attire yesterday and now she felt she was being dismissed like a schoolgirl after completing some kind of uniform check.

She was no naïve schoolgirl though. They both knew and understood that the "uniform check" had been less than thorough for the time being. It was all part of the game. She took a few rapid sips of wine trying to compose herself.

Her mind raced. "What did you expect, he'd check under your skirt from minute one?" Inexplicably, she found herself answering yes. Somehow, some part of her conceded that it was exactly what she'd been hoping for. His cool reaction was not what she'd been expecting at all.

John was unpredictable and it made her more than a little nervous. Which excited her exponentially. She liked being mind-fucked. No other man had pulled this off since she was a naive coed. And she was most assuredly a coed no longer.

If she were honest with herself, she didn't want him to resist her. Did you think he'd catch one sight of you in this get up, lift you up on the bar and fuck you senseless? Yes, yes, yes, a little voice in her head whispered. Hot flashes of embarrassment shone in her eyes, and she turned away from him quickly lest she reveal her insecurity.

The maitre'd returned and addressed the couple as they sat together silently, the sexual tension speaking more than any words could express. "Madame, sir, your table in the private room is ready. I will assure your wine is brought to your table. Please, if you will, follow me."

Kathy could feel John's eyes on her backside as she slowly sauntered away, giving him for the first time a view of her outfit from behind. She held her breath, wondering perhaps if her buttocks were indeed showing.

She knew that the skirt hid very little and her high heels made her ass move provocatively when she walked. That's why we wear them, she thought, and headed towards the door to the private room.

John said nothing, merely admiring the beautiful view of her swaying behind that had his cock hardening in an instant. Fuck, he thought, the woman wiggles like a glow worm when she walks, to quote from the great Chuck Berry. Long as she got that ass, the music will never stop, he paraphrased to himself. Roll Over Beethoven, indeed. My temperature's risin', and my heart's beatin' rhythm.

As the slight distance from him helped her regain her own bearings, Kathy glanced around the attractive room. It was clean, tidy and quaint. She noted that all the romantic details were in place. Soft lamps, candles and background music all combined to give the room an easy comfortable style. Enticing food aromas wafting from the kitchen reminded her that she'd been too nervous to eat much during the day. Even though she had butterflies in her belly, she was looking forward to dinner.

Kathy had to admire John's charm as a date. He was one of those people who could order the meal in fluent Italian, make sure her wine goblet was always full and carry on a conversation without missing a beat. The dinner was light, well prepared and delicious. He managed to engage her in conversation about herself, her family, where she was from originally, her tastes on music and the arts and her views on life in general, flirting with her just a little all the while.

As pleasant as it was and as much as she was enjoying herself, Kathy felt distracted and a little unsure of herself. In some ways when she agreed to come, she'd expected a straight-out seduction scenario. The man had said he wanted to see her ass, it seemed his intention couldn't have been plainer. Now she wasn't so sure. Did he really want to talk about her? And if that was the case, why all the obsession about dressing up in this manner?

Kathy wasn't really complaining, though. It certainly was nice to be wined and dined in a civilized way. Most of the men she'd been with recently took one look at her, and somehow thought that sex was the only thing she was interested in. Which was pretty much accurate.

Now that Kathy had cause to be introspective, she realized that absolutely sex WAS the only thing that she was interested in with her recent suitors, and oh, there had been many in the last year. Fuck buddies, wham, bam, thank you ma'am frenzy. Usually one and done. Inevitably they quickly bored her by not having any willpower when she fucked with their heads. Or, even worse, they had failed to titillate her most important and fertile sex organ. Her mind. "Was it possible to have orgasms of the brain?" she wondered, as she fidgeted over her plate.

John was turning out to be a very different kind of date. Sophisticated, attentive and very unpredictable and that made him all the more fascinating. And patently irresistible.

John noticed that she twirled and fiddled with her glass, folded and refolded her napkin a dozen times, actually eating very little. "What's the matter Kathryn, don't you like the food?" He inquired, concern showing on his face.

"No, no it's great. Excellent, really, John. It's perfect." She guiltily made an effort to consume a little more of the tender steak. Swallowing was the issue, getting past the lump embedded in her throat to be exact. And she planned on doing a fair amount of swallowing soon. it was all she could do to do not crawl on her knees under the table and suck his cock.

Sitting, Kathy's skirt had ridden up high, almost disappearing into her lap, making her very conscious of her nearly bare ass virtually sticking on the surface of the seat. She knew with some certainty that at some time during the course of the evening he was going to find out just how saturated she was. Kathy found herself wondering how and when he was ultimately going to take her. She wanted to be taken. She needed it. She had never wanted a man more.

John excused himself for a moment, leaving Kathy alone with her thoughts and her gushing cunt. When he returned, he gently clicked the lock on the doorknob, a lock that Kathy hadn't noticed until just now. He further dimmed the lights, leaving only candlelight to illuminate the couple. He walked leisurely to the curtains and pulled then tightly shut.

Kathy gulped. She was aware that her slit was literally pumping sex fluids out of her, streaming down inner thighs like a bubbling brook in Springtime.

Returning to the table, he searched her face almost bemusedly as he asked, "I know Kathryn, I've got an idea, now that we've had dinner, why don't we play that game?"

"What...k-kind of game do you want to play?" she asked tentatively, momentarily forgetting what he had called it. The Ass Game. The sexual dessert and the main course, all in one. The reason she was here, dressed like this. To play the game.

He smiled at her and clucked his tongue in mock disappointment. "Come, come, Kathryn. There is only one playing field tonight. Your ass."

Kathy's heart raced, her legs trembled as she pressed her thighs together in an unsuccessful attempt to stop the vaginal floodgates from seeping.

He laughed quietly. "If your smell of sex was any more pronounced, I'm afraid you would set off the smoke detectors, Kathryn. And you're so on fire, that then the sprinkler heads may activate. And that would make us both soaked." He paused. "And we both know that only one of us needs to be sopping wet, isn't that, right, Kathryn?"

She stood up. She didn't know why, except that she only knew she couldn't sit any more.

John stood as well. Moving closer, he gently pulled her to him, his hands at the small of her back. She was having trouble breathing.

He whispered into her ear. "You're blushing, Kathryn. It's been a long time since I've seen a grown woman blush. Hmm, I wonder why? Could it be that Kathryn is more than ready to play the game? Let's see now, am I right?"

Kathy was acutely aware of his warm hands moving lower, very gently caressing her behind. She let out a little moan, the tension escaping through her sounds. His hands felt good. Very, very, good. She closed her eyes for a moment.

As his hands gently squeezed her buttocks, John could plainly feel her wetness that had eased down into the crack of her ass hole. His fingers rubbed at the crack between her ass cheeks while he spoke." Well, what have we under here? Is this the little secret that's made you skittish all night, Kathryn? A soaked cunt?"

She said nothing, biting her bottom lip, her eyes avoiding his.

"Tell me, Kathryn. Or better still why don't you show me? Show me your ass. Because it's not that needy pussy I'm interested in. Apparently it's off limits, based on the photos you sent me." He spoke in that quiet, controlled voice.

Kathy felt a little foolish, not quite knowing what he meant. Did he want her to lift her skirt or take her skirt off? What exactly did he want her to show him?

Seeing confusion on her face, he directed her, speaking slowly as though she were child. "Turn around, Kathryn, that's right." With his hand on her shoulders, he turned her away from him. John stood very close behind her now, speaking almost directly into her ear, running his hand over her thigh.

"You see, Kathryn....." his voice was eerily calm now, almost icy. Perhaps that was why Kathy now had goose bumps and her nipples were taut and hard. "......If you would have sent me pictures of your cunt exposed, we'd be playing the Pussy Game tonight." He paused to let that sink in to her.

"But you didn't. You sent me pictures of your ass, which I could only assume meant that you were willing to give it to me as a gift."

"So we'll play the Ass Game together. We'll tease and please your lovely ass. Pleasing your pussy is entirely up to you. "

He guided her firmly, his hand on her arm to the couch. "Bend over here," he said speaking quietly, his face close to hers, patting the dark leather of the chair he had been sitting in.

"What?" She turned her head to look at him, her eyes wide open in surprise. She wanted to check that she'd heard correctly.

She almost thought he joking but the look on his face and his tone told her that he was serious. He seemed to be challenging her, testing her to see how far she'd go. She stood motionless, standing her ground for a moment. She felt strangely immobilized as though he was speaking to some other person. Part of her wanted to please him. Part of her hated him for making her feel like a silly child.

"I said bend over, Kathryn," his voice now registering some disdain. "Did I fucking stutter?"

Absurdly, her brain registered not the strangeness of his request but his lack of manners, and somewhere in the deep recesses of her mind she wanted him to say please. She thought, "Ask me proper and I'll do it," but then she calculated that she was about to be ass-fucked, so Miss Manners' etiquette probably wasn't applicable in this particular situation.

He read her hesitation and reluctance to move as defiance. Placing his hand in the small of her back, he bent her firmly forward, pressing her down until her belly rested on the soft brown leather and her skirt stretched tightly over her round ass.

"Like this, Kathryn."

Hot tears that had been held in check by her confusion and disbelief pricked in her eyes now as her embarrassment grew.

He directed her precisely. "Bend over more, keep your legs straight and dip your back, that's right." As she bent further, her breasts pushed into the upholstery sending a tiny wave of electric pleasure to her pussy.

"Spread your legs." When she didn't respond, he pressed his knee between hers roughly nudging her legs apart. "Spread your legs now, Kathryn. Push your ass up. Come on, Kathryn, show me what you did in your photos. Are you interested in presenting your ass to me, or aren't you? Are you a teaser or a pleaser?"

Rational thought seemed beyond her at this point and Kathy let herself be directed, pushed and prodded into position. Her face burned with shame. Her thighs were already beginning to feel the uncomfortable stretch in her muscles.

"Let's try it with your head down a little lower. Ah, yes, that's right, Kathryn, just gorgeous. Such a sweet, tight, round ass, push it up just a little more, nice and high." His tone softened a little as he used his hands to guide her head down, until he was happy with the lewdness of her position. John stood back for moment and enjoying the sight of her gaping pink ass hole as her skirt rode up rudely exposing her thighs, the skin of her buttocks and the pink puffy edges of her labia.

John ran his index finger along the line where her long legs met the bare flesh of the lower half of her buttocks. He felt her tremble, goose bumps rising more prominently across her smooth skin. His finger slowly traveled across one sweet cheek into the dividing valley and slowly over the other buttock.

Without a word, he did it again. Next his finger traced the rim of her anus where her bottom was revealed. He appeared to be emphatically underlining his discovery. Kathy held her breath, every muscle in her body tense, waiting for his next move. She was captive, and never had she been more willing to be assaulted anally.

In her mind, which was now sympathetic with her captor, she deserved it.

His hands cupped the soft warm flesh of her buttock, briefly, first one side, then the other. Ever so slowly, taking the hem in his hands, he peeled her skirt up. Inch by inch, up it went over her upturned bottom until it gathered around her waist. She moaned out loud as he pulled her cheeks apart lewdly, so much so that her ass hole literally winking at him, her sphincter pulsing, anticipating the inevitable intrusion. She had most definitely been exposed.

"I'm sorry," she finally whimpered. Her voice was barely audible. Her breath coming in little gasps, making speech difficult. Was she sorry? Kathy didn't know what she felt, or really why she was sorry. Was it for teasing him? The only thing she knew for certain was that she had wanted him and that the thought made her pussy wet and her ass ache. She also knew that she had deliberately provoked him and now he seemed intent on teaching her some kind of lesson, a hard lesson.

His hand roamed over her backside, squeezing and rubbing her soft flesh, pushing at the crease between her cheeks, making her pussy quake furiously. John loved the way her firm cheeks filled his hands. He couldn't resist pinching her gently as if testing her ripeness. She squealed a girlish sound that made him smile.

"What do you think should happen to a cock tease like you, Kathryn? After all, you're old enough to know better. Or do you send photos like that to all men online so that you can have them fuck your pussy and mouth? Well, I'm going to ignore your cunt, Kathryn, but feel free to fend for yourself. While you think about all that, I'll take my cock out, shall I?"

Was he really going to fuck her like this? Right here? Kathy cringed, scrunching up her eyes, closing them tightly to close out the vision in the mirror on the wall of herself, bent, bare assed like a naughty child awaiting punishment for her misdemeanors.

He stroked his hard, thick cock and calmly stepped out of his pants. Lifting the hem of her skirt until just about the place he estimated she had done in her photo, he grabbed her hips and fully exposed her beautiful, pale, round ass, framing her nakedness. John swallowed hard at the sight, his cock twitching wildly on her ass crack, like a bucking bronco ready to break through the rodeo gate. A small moan escaped from Kathy's lips as the engorged mushroom tip of his cock made contact with the naked flesh of her most intimate hole.