tagAnalThe Ass Game

The Ass Game


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.

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