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The Ass Game

Category: Anal Sex
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Twenty minutes into her first date with the man she contacted on the electronic dating site that she used to get laid when the spirit moved her, Kathryn Udall was afraid she was losing her keen sense of intuition.

Kathy was unlike many women in the electronic forum in that she made no bones about her ultimate intentions. She wasn’t looking for a “soulmate” or someone to hold hands with on the beach at sunset.

Nope, she was looking for cock.

It was refreshing, really, and not surprisingly, most men that she contacted via the Net shared her enthusiasm for a “friends with benefits” situation until each one got tired of the other, or as Kathryn phrased it, “simultaneous buh-byes.” Some of her relationships lasted last than a hour, some several weeks at best, but Kathy didn’t need the emotional burden of a traditional “boyfriend” at the age of fifty-one.

Nope, she needed dick. And it was usually available at the click of a mouse. Because Kathy Udall was about as smokin’ as a woman over fifty could get. Five-feet-four, 118 pounds soaking wet (which she usually was), short blond hair, light green cat-like eyes, and a ‘come-fuck-me ‘smile that would have made Mae West look prudish by comparison.

She’d been “separated” from her husband of over two decades for almost a year now, and as Kathy would chuckle to herself, if a woman’s profile listed “recently separated” as their status, well, that was a synonym for “needs to get fucked, now”. There might as well have been a symbol on such profiles of a yawning, sopping pussy to further emphasize what the “recently separated” were seeking.

In her year of playing on what she affectionately called ‘match dot cum’, Kathy could pretty much flush out those men who were ready, willing and able (which wasn’t difficult). But more so, Kathy was also discerning enough to hook up with quality men only, at least from her perspective. And that meant well-to-do and discrete. Kathy Udall didn’t need the world to know her dalliances, Besides, it was daring enough that she had recently contacted a photographer who had posted a portfolio of Kathy’s pictures on a modeling web page, and some were rather risque for a fifty-one-year-old perceived pillar of Lehigh Valley society.

The photos were what Kathy had used as bait in recent months to seal the deal. She had a particular set of photos that she would e-mail to men after some initial chatting and flirting, and by then, the men were inevitably putty in her hands. Most suggested a first date at a hotel, and there were a few offers that Kathy had accepted and they thoroughly enjoyed the eight-hour shift work of sex.

But this man, well, either Kathryn had badly misjudged this man or she was losing her touch,and she failed to believe the latter could be true. He had insisted on meeting for coffee on a weekday afternoon for a first meeting, and hadn’t yet mentioned nor acknowledged the e-mail attachment she had sent to him that showed various photos of what Kathy knew was her best feature.

Her tight fifty-one year-old butt. Bare as a baby’s behind, out there in all of its photogenic glory.

Kathy was about to terminate this meeting prematurely as she sipped on her grande mocha-something-decaf. He was nice enough, true, and more than easy on the eyes, but his complete lack of provocative conversation told Kathy that maybe this man was one of those who wasn’t interested in just a quick roll in the hay as an ice-breaker.

“You know,” she said, glancing at her Movado wristwatch and starting to rise from her chair, “I should probably be going soon, John. I hate to be so blunt, but, well, I kind of know in a hurry if there’s any chemistry, and I just don’t think we’re a match. It’s been nice meeting you, though,and good luck in your……..”

“Why did you show me your ass, Kathryn?” he asked quietly in the same monotone voice he had used all afternoon. No excitement, no betrayal of emotion.

Kathy sat back down in her chair, placing her perfectly manicured hands on the thighs of her designer jeans. This had captured her attention. Had she heard him correctly. “Excuse me?”, she asked, unaware that her face had flushed perceptibly.

The man that she had met less than a half hour sipped on his green tea. “Your ass. Why did you send me pictures of your naked ass, Kathryn? You hadn’t even met me. Do you do that to all of the men you meet on-line?”

No man had ever asked that question before, that was for sure. Hell, Kathy thought, no man gave a shit what I sent to other men, did they?

Kathy fidgeted, not knowing exactly how to answer that question now that it was posed pointedly. it was a good question. What WAS she hoping to achieve, really? “Well, I, um, I wanted to..I guess, …….hmmm, I don’t know.” She was blushing now, despite herself. She felt a bit like a chastised schoolgirl and didn’t know quite why.

“You don’t know?” John chuckled into his cup and shook his head as if he wasn’t going to buy that answer. For the first time, his voice became slightly animated, showing a faint indication of interest. “Not that I minded. How did you know I was an ass man, Kathryn?”

Kathy regrouped quickly, glad that their conversation was going in a direction that she had originally anticipated. Better late than never, she surmised.

“I suppose I wanted to tease you a bit,” she admitted demurely. “I liked you, is that so bad?”

John let the smallest of grins escape. His nose wrinkled a bit as he contemplated the compliment. “No, no, that’s not bad at all, Kathryn. It shows you have good taste in men, though your tactics are a bit…….odd, I dare say.”

Kathy again felt admonished, and she didn’t like it. Although she wondered why she had a warm feeling beginning to bubble in her loins.

“Odd?” Kathy pondered this. “What’s so odd about wanting to please a man that I found very attractive?”

“Oh, it was to please me now, was it? A second ago it was to tease me. So, which is it, really? To please…or to tease?” He nibbled on his cup with his full lower lip, which Kathy found interminably sexy. “There’s a big difference, you know. Between teasing and pleasing, that is. So, which is it? Are you a pleaser, or a teaser?”

He stood up from his chair and reached for his sports jacket, which had been hanging casually from the back of his chair. “Inquiring minds want to know, Kathryn. C’mon, we can discuss it on our way out. Ya know, since there’s no chemistry and everything……” He let the words dangle in the acoustics of the cozy cafe.

He gestured for her to get up, and she did, silently, her head spinning a bit. Were they breaking up, she mused in her head? This was a record. Not even break-up sex…….?

He followed her through the coffee shop, navigating their collective way through the tables. His eyes were riveted onto her denim-clad rear end. It was a truly incredible ass for a woman of any age, never mind one in her fifties.

He had seen that ass naked, at least in a photo, where she was lying face down on a rug with a blouse sweater that was pulled up to reveal her entire hind quarters. Her legs were spread ever so slightly as he remember it, showing just a hint of her pussy and the puckered rung of a pretty pink anus.

And he knew he would have it. In due time. When he was good and ready.

Because, he knew intuitively that Kathryn wanted him to take it. And he was a teaser and a pleaser, also. Two could play at the ass game.

They walked to Kathy’s car in silence and stopped when they reached the driver door. She fumbled for her keys, and began an attempt to make amends. “Look, John, I’m sorry, I really am. Can we start over? I’d like to see you agai………”

“Kiss me,” he said softly, pressing into her pelvis with his own, right in the broad daylight of the strip mall parking lot, placing one hand ever so gently on her buttock.

She felt his bulge, and it was not insubstantial. Kathy was no stranger to cock, and a bit of a size queen. She was a lot better in mentally sizing up a man’s girth than she was his character. Maybe because she didn’t hang around men long enough to truly care about the size of their character.

“What?” she asked, sincerely surprised, glancing around the lot to see if they were being watched. But he noticed that not only had she not backed away, but she actually leaned her crotch into his ever so slightly.

His lips mover closer to hers. She could feel his breath on her cheek and his hand easing between the crack of her ass, pulling her closer. “Kiss me. let’s find out if you’re a pleaser or a teaser, Kathryn.”

They kissed softly, their lips exploring each other’s tentatively. It was nice, Kathy thought, the humidity rising in her nether region on this otherwise chilly day, and just as she was about to ease her tongue into his warm mouth, he withdrew.

He placed his hand snugly on each hip and twirled her around so that her back was to him now, and he brushed her blonde locks from her face, pressing his trouser-covered cock into her ass. Kathy knew immediately that she was in the grasp of a well-endowed man, and she moaned into his shoulder.

He lifted her face off of his shirt and put his hand oh, so delicately on her throat. “Now, this time, Kathryn, kiss me like you want to fuck me. Because you do, don’t you?”

Kathy groaned, suddenly completely impervious to the surroundings, his words opening up the flood gates to her pussy. She hung her head back and their tongues first danced and fought a sweet skirmish for supremacy for what seemed like minutes, his cock rising by the second as Kathy pushed back with impassioned arousal.

She reached down behind her to try to palm the large growth that was leaving an indentation in her denim, but he brushed her hand away firmly.

He released his mouth from hers and left her gasping and flushed. And wet. God, Kathy thought, I’m so fucking wet…………..

“Maybe you’re a bit of both, Kathryn. A tease who aims to please. And perhaps I am as well. Kindred souls, perhaps.” Kathy leaned back again and raised her head to his, hungry for another hot kiss, oblivious to the public display of affection that was gathering quite an audience within the confines of the nearby coffee shop.

He let go of her hips and smoothed her hair back off of her glazed eyes. He stepped back, and it felt for a second that they might need a device of some kind to extract his cock from the crease in her jeans’ hind quarters.

“You’ll meet me for dinner tomorrow night at Marcello’s at eight,” John remarked casually, matter-of-factly. It was not an invitation, Kathy quickly realized.

It was a command.

He continued, though she was duly distracted now, fighting an overwhelming instinct to push him into the back seat of her late-model BMW and suck that glorious cock, right here and now. And she could have cared less who would watch. Bring ’em on, she thought, sell tickets if need be, give ’em a show.

“Very shortly, I’ll text you instructions with what to wear. And you will follow my instructions to the letter, won’t you, Kathryn?” He kissed her on the forehead tenderly and began to walk to his own car, a sporty black Lexus.

“Because you’re a teaser. And a pleaser. Until tomorrow, then.” He blew her a kiss.

She staggered into the car seat and slumped down, glancing in the rear view mirror at her tousled blond mane. She was literally gasping for breath. it felt as if a small wading pool had formed between her legs, wet, warm, and oh, so wonderful.

At each traffic light and stop sign, Kathy had to resist the urge to pull her jeans to her ankles and to frig herself to orgasm. She craved release. THIS is what she wanted, she realized. A man to control HER, a man to both fuck her AND to mind-fuck her. She was a very naughty girl already, but she needed a man to take the lead. This would capture her interest beyond just a hot fuck or three.

She had barely pulled into her driveway ten minutes later when her cell phone vibrated to signal an incoming text.

“Important details, Kathryn. For our dinner tomorrow, I want you to wear something special, something very particular, do you think you could do that for me? We can make it our first deal if you like.”

Kathryn shut off the ignition to her car and hurried into her house through the garage door. She didn’t hesitate.

“Yes,” she tapped simply in reply. That said it all. She had set the tone that she would be compliant, cooperative…..yes, submissive.

This guy could be a handful was Kathy’s first thought. Nevertheless, she was intrigued to hear his request. Only when his next text came, it didn’t exactly come out sounding like a request. It sounded quite clearly like the directive that it was.

“Wear a little black skirt for me, no stockings, bare legs, high heels, no panties, I’ll leave the top to you. The skirt has to be tight, very tight and short, way above your knees short. I want to see your ass.”

Kathy’s eyebrows by this time were just about embedded in her hairline. “You want what?” she wrote back, somewhat taken back, but mostly seeking further assurance to overcome her anxiety. And just why was she still so fucking wet?

His reply took longer than Kathy was comfortable with. She squirmed as she walked to her bedroom, shedding clothes as she ascended the stairs. Finally, the vibration, which coincidentally, came as she extracted her rabbit vibrator from her night stand drawer. Imagine the irony, she smiled to her self, aware that she was shaking slightly as she climbed onto her mattress wearing only her bra and barely-there thong now.

She had prepared her accessory items today just in case she ended up having a quickie with her coffee shop date. A girl can’t be too prepared, you know, she thought to herself, idly rubbing her nipples through the sheer material of her lacy bra.

“Just as I wrote. I want to see your lovely ass, Kathryn. After all, you like showing it to me, don’t you? I want to see the skirt, stretched tight over your very beautiful backside when you walk into the restaurant to meet me. I’d like that very much. It’ll be a game, like playing dress up… It’s quite simple really. We’ll call it The Ass Game. Do it for me.”

Kathy could almost hear his calm, authoritative voice in the text. The last statement was thrown down as a challenge. What’s not to understand? She had a clear mental image of his instruction. The man’s completely trouble, cute, but big trouble. For a moment, Kathy imagined herself panty less, her ass held tight in the soft embrace of her shortest, tightest black skirt, killer heels…her legs wrapped around his waist eventually, that was a given.

Her body registered the image too. She could feel her nipples pucker under her caress now and the familiar heavy feeling beginning to increasingly gather between her legs. In fact, she let her other hand drop so she could feel her pussy getting saturated at the image and his words.

Kathy used one pussy-juice-covered finger now to tap her reply. It was her last flimsy attempt at indignation, defiance.

“Tell me again why I’m going to play dress up for you, John. I seem to perhaps have missed a step in our mating ritual?”

She was on the verge of orgasm, her rabbit buzzing over her labia, by the time his response came.

“Oh, that’s easy, Kathryn. Because you like to tease men and because you want to please me. You want to reward me for encouraging you to do what you really want to.” Kathy sighed deeply. She could almost hear him laughing, mocking, daring her. His text continued.

“Because I’m a great tease myself and all the other men ogling you will be worth it, trust me. Or perhaps because you’re aroused and you want to do something reckless. Because if you’re honest with yourself, you’re fascinated by my proposal. Enough reasons, or should I continue?”

Trouble, with a capital T. But the more he wrote, the wetter she got. She was desperately fighting off release now, trembling, her pussy gushing nectar onto her quilt.

He paused for a moment letting her digest his words. “You know you want to but you’re scared…Kathryn, I don’t care why you do it, just do it! Come on, do something rash, maybe even a little dangerous. It’s not too much to ask a sophisticated woman like you, is it?” He goaded her playfully, he may as well have said she was too prudish and conservative to take up his directive.

She abbreviated her own self-indulgence for a few precious seconds to hit the keys. She had the rest of the day to masturbate, which she probably would do for a good portion of it, she thought.

“That’s ironic coming from a control freak!” She laughed out loud at her words. She sounded like an adolescent. She recovered, lest her text be misinterpreted by the receiver.

A little breathlessly, she replied, “Tight short skirt, bare legs, heels, you want to see my ass, heck, who doesn’t? Tomorrow, meet you at the restaurant, yep, got it.” She nodded to herself as if signing off a checklist and giggled a little.

“No panties,” he quickly corrected.

“No panties, check,” she just as expediently replied.

“No panties, Kathryn. Good, we have an agreement then for our first dinner date. I’ll look forward to tomorrow.”

Okay, she thought, I think I can do this, play the game, the “Ass Game”…hey, it’s got to be a game, right? He seemed serious about it though. The devil in her couldn’t resist a little dig, tongue in cheek and smiling wickedly, eyes shining with excitement, she queried,

“So, Mr. Control Freak, I’ve just got ask, what happens to naughty girls who don’t obey… I mean, follow your instructions?”

John answered briefly, somewhat ominously, and Kathryn knew to play no more. “Oh, I’m sure you’ll make the right choice, Kathryn. If you want to please me. And be pleased. So I suggest you don’t disappoint me.”

Kathy groaned as she signed off of her phone and came in an explosive rush as she plunged the rabbit’s head into her anus. She passed out and when she awoke, it was night time. She glanced at her alarm clock. Eight o’clock. Twenty-four hours away.


By the time the next night arrived, anticipation and her vivid imagination had gone into overdrive. Kathy was very excited and just a little bit scared of what she’d let herself in for. “The Ass Game, eh?” she muttered to herself quietly, rummaging around in her wardrobe. She spent a good deal of time carefully choosing her outfit, mentally going over his instructions, which she had repeated over and over in her mind.

“A little black skirt, no panties, no stockings, bare legs, black high heels, I’ll leave the top to you. The skirt has to be tight, very tight and short, way above your knees short. I want to see your ass.”

Those outrageous requests, delivered in such a cavalier though cocky manner by a virtual stranger had sent little shocks of pleasure straight to her cunt for twenty-four long hours. Her pussy continued to be coated with a slippery sheen even now as she replayed his words over and over in her head, enjoying their effect.

Checking the reflection in her bedroom mirror she admired what he would see when she entered the restaurant. Short blonde spiky hair, which she had professionally attended to earlier today, gold hoops in her ears, a pretty, lightly made up face, a simple V-neck white tee shirt, a hint of creamy cleavage visible. And, of course, the coup de grace. A black skirt that ended high on her smooth thighs, long, bare legs and her favorite black patent leather pumps.

She stretched a leg out toward the mirror, vamp style, enjoying the way the heels made her slim legs look impossibly long. “Beautiful, slutty, perfect for the occasion. Come-Fuck-My-Ass shoes. Shoes that could make a grown man weep, Kathy,” she laughed at her own far-fetched imagery.

Turning, she checked the view from behind. The skirt was tight, very tight, hugging her shapely ass, the stretchy fabric leaving very little to the imagination. She hitched the skirt a little higher and was satisfied with the effect. “All details in place, check,” she said out loud to her reflection.

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.

Leaning down, he placed a soft kiss on each smooth cheek, inhaling the tantalizing scent of her.

“Perfect, naughty Kathryn, just perfect.”

God, she knew he could see all of her now. As if reading her mind and wanting to illustrate the fact, John pulled his cock back and pressed his fingers to her exposed anus, so pink, so ripe. She gasped as he probed, tormenting her.

“Please… don’t.”

“Don’t what, Kathryn? Don’t touch you? Don’t play with your pretty little ass hole, is that what you’re begging for?” She moaned as his finger pushed deep into her slick folds.

“No,” she panted. She squeezed her sex flesh to grip his finger, moaning in disappointment when he withdrew it. “No, that’s not what I meant. I want your big dick in my tight ass hole, not your puny finger.”

She hissed back at him over her shoulder, her blond hair matted and sweaty on her forehead. “Don’t wait any longer. Fuck my ass. Take it.”

She felt her inner tunnel expand as his throbbing cock head entered her ass, perhaps an inch or two. “Splendid. Good girl. Let’s begin the game, shall we?” he said quietly, almost to himself.

She heard a loud swooshing sound as he raised his hand and bought it down hard on her right buttock. A little yelp escaped from her lips. He spanked her again, firmly spanking each cheek in turn, leaving pink hand prints on her skin. Again, his heavy hand met her bare ass. Three times, four, his hand fell. The stinging on the outside of her cheeks served to distract her from the pain inside of her ass as with each slap he went deeper into her anus.

“I think that’s exactly what you deserve isn’t, Kathryn? I do believe I’m going to enjoy giving you what you really need. This is a fun game, is it not?”


Kathy let out a moan as the sting of her flesh registered. The pain shocked and surprised her. She really thought he’d been playing, that maybe he’d give her a few playful spanks and all would be forgiven. His cock in her ass told her something very different. He seemed intent on really punishing her. He waited a moment before allowing his hand to fall again.

“Keep your bottom up, Kathryn. I’m not all the way in yet.” He pressed the small of her back gently, making her bottom tilt more invitingly upward. “Aah, yes, that’s better, much better.”

The spanks stung and she began to hurt worse on the outside than the now pleasurable reaming of her anus. Still he continued spanking her poor pink bottom, building the speed, harder and faster. He loved the way her reddened flesh bounced and jiggled under his hand.

“Ohhh…ow! Please…please…”

John paused for just a moment to clarify her request, enjoying the heat of her skin under his hand. “Please what, Kathryn? Spank you harder?”

“No, fuck me harder,” she sneered defiantly. “Is that all you got?”

He roughly placed a hand in the middle of her back and repositioned her. “Bend over, push your bottom out Kathryn, open your legs wider, I want to see all of you as I come in you. Be brave, sweet girl, I’m almost there. Your ass is just sensational.”. His voice soothed her somehow. She thought of Sally Field’s impassioned speech when she won the Academy Award, but with a twist.

“He likes my ass! He REALLY likes my ass.” She giggled despite the incredible dichotomy of intense pain and indescribable pleasure.

His hands rubbed over her hot flesh, reigniting the sting of his spanks. The speed of his thrusts increased, radiating as pleasure to her pussy. She balanced herself tenuously with one hand on the chair and began to rub her clit with the free hand. She was on the verge of the most explosive orgasm of her life.

She did as he asked, bending again, moving her legs a little wider apart, as far as they would allow without her falling over. She knew without doubt that she was about to squirt. She no longer cared. She wanted his punishment. Her pussy ached and her ass braced to accept him for one final violent thrust as the smoldering heat of his semen rushed into her.

She heard him groan, a deep, lust filled sound that escaped involuntarily from his mouth.

Kathy whimpered when he reluctantly withdrew, his cock deflating. Her ass, now empty, was still on fire. He might have been done, but she wasn’t.

She looked back at John, his face a bright crimson, his withering cock dripping the residue of his ejaculate on the floor.

“Could you do me a favor, John?” He looked down at her, noticing she hadn’t moved, except to clench his cum from her gaping hole with her pulsing sphincter muscles.

“Remind me to send you photos of my pussy tomorrow? I want to play that game next, OK?”

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