Jackpot

"No, not really," Bobby admitted. "She's just a friend."

"But you'd like her to be more than that?"

"Sometimes yes, sometimes no."

"Have you ever had a girlfriend?"

"I guess that depends on how you define girlfriend," Bobby said, the alcohol having enough of an effect on him that he spoke more freely than he normally would.

"Someone you sleep with might be one definition," Shirley suggested, watching for the young man's reaction.

"No girlfriend then," he said, a strong sense of regret in his voice.

"Then you're a ..." Shirley started to ask.

"No, I'm not," he replied before she could even say the word.

"There wouldn't be anything wrong with it if you were," Shirley said with reassurance in her voice. "I was just curious, that's all."

Reaching for another snack, Bobby hadn't even realized that his glass had been refilled once more. He just picked it up and drained more than half of it without thinking.

"Are you tired?" Shirley asked.

"Actually no," he answered, almost surprised at his answer since he'd been up all day.

"Me neither," Shirley said, "I guess it must be the excitement of winning and all."

Bobby just nodded his head in agreement.

"What say we see what's on the TV?" Shirley said as, without waiting for an answer, she picked up the remote and began surfing through the channels.

As different stations appeared and disappeared on the large thirty-two inch screen, Bobby noted that the television up here had a lot more options than the one down in his own room. In addition to the single HBO and a few other premium channels, this television also seemed to have the pay for view channels also unlocked.

"Oh my, this is interesting," he heard Shirley say as his attention drifted from the screen to reach for another piece of cheese. Looking back at the screen, he almost swallowed the small cube whole.

Evidently, even the porn channel was free to guests lucky enough to be staying in one of the expensive suites. There, on the screen, was a large breasted blonde going down on a dark haired man. At the same time, another man, this one with blond hair and a beard, was entering her from behind. Not exactly the kind of must see TV he was used to at home.

Silently they watched the movie for another half minute or so, Shirley watching Bobby's reaction out of the corner of her eye. Finally, she asked him if the movie bothered him.

"I know that not everyone has a taste for this sort of thing," she clarified her question.

"No, it doesn't bother me," he haltingly replied, "not unless it bothers you."

"Why would it bother me," she asked with a grin. "Is there some kind of rule that a woman can't enjoy erotica, or is it that you think I'm too old?"

"I don't think you're too old," Bobby replied, not knowing what else to say.

"Really?" Shirley said, genuine surprise in her voice. "How old do you think I am?"

"I'm really not good at guessing someone's age," Bobby offered.

"Oh go on," Shirley encouraged him. "I won't be offended if you get it wrong."

Bobby had no idea what to guess. He remembered thinking earlier that Shirley was probably around his mother's age so he decided to guess that. Then he decided to shave off a year or two just to be sure he didn't offend her.

"Err.. Forty?" he said.

"You're kidding, right?" Shirley asked in disbelief.

"I didn't mean to offend you," he quickly apologized as a worried look appeared on his face. "I told you I wasn't any good at it."

"Offended...?" Shirley said as she burst out laughing. "Honey, I haven't felt this flattered in years."

Bobby let out a loud sigh of relief.

"I haven't seen forty since you were in diapers," Shirley added.

Now it was Bobby's face that filled with disbelief.

"I'm going to be sixty-one next month," she concluded.

-=-=-=-

"Would you like another drink?" Shirley asked an obviously stunned Bobby.

"I think that maybe I've had too many already," came his reply.

He sat there for a few moments, then asked if it would be okay if he turned off the television. Suddenly, he felt very uncomfortable watching porn with a woman older than his grandmother.

"Is there something wrong?" Shirley asked as she took note of his sudden change in demeanor.

"I just feel kind of funny," Bobby offered.

"Because I'm older than you thought I was?"

"I guess so," he replied meekly.

"Why is it suddenly any different?" Shirley asked. "We're still the same people we were five minutes ago."

"It just seems different, that's all," Bobby said.

"Why?"

Bobby didn't answer, but it was obvious that he was now embarrassed about something.

"Was it because of what was on the television?"

"Sort of."

Shirley thought about it for a few moments, then had a sudden revelation.

"Bobby, did you think I was trying to seduce you?" she asked.

Again he remained silent, but the look on his face told her she had guessed right.

"Oh my," Shirley said on realizing she'd guessed right. "Now I'm the one who's embarrassed."

Bobby finally looked up at her and sort of smiled.

"Bobby, I swear, trying to seduce you was the furthest thing from my mind when I asked you up here," she said, then paused a few seconds, "At least I think it was."

Now she had the young man's full attention.

"I don't know, maybe subconsciously, I was trying a little," she confessed. "I mean it's not like I've never seduced a man before. I just usually know I'm doing it."

Again she paused for a few seconds, then asked, "Were you hoping I was going to seduce you?"

Silence again gave her an answer.

"But now that you know how old I am, you've changed your mind. Is that it? Now everything is different."

This time she waited for an answer, letting him know that silence was no longer an option.

"I guess it shouldn't be, but I don't know," he finally said.

"Have I grown less attractive to you in the last few minutes?"

"No."

"But now that I'm such an old lady, the thought of sleeping with me is repulsive," she said, moving closer to him, "is that it?"

Shirley took a deep breath, both to give him time to answer and to give herself of moment to think. Had she really, if only subconsciously, been planning to seduce this young man? Even at sixty, finding bed partners was hardly a problem, so why had this boy, because that's all he really was, interest her so?

Before she answer that question for herself, Bobby expressed the thought that maybe it might be a good idea if he left.

"If that's what you really want, then fine," Shirley said, "but be sure that you're leaving because this isn't something that you want, not because of some silly hang up about age or what people might say if they knew."

She gave him a second or two to digest that, then added, "Do you know what they call a sixty year old man who has a twenty-one year old woman in his bed?"

Bobby didn't have time to even guess before she answered for him.

"Lucky, that's what."

That single word told her that she'd made up her own mind, now it was just a matter of having Bobby make up his. Still, nothing said she couldn't nudge him in the right direction.

-=-=-=-

Stepping next to Bobby, who was on the far edge of the armless couch, Shirley placed her hand on the back of his neck and rubbed softly. She continued for a long minute then, feeling no objection, lifted her left leg and draped it across Booby's right one. He ran his hand up and down her stocking-covered calf, slowly moving up to her thigh. Looking up at her, his face now filled with a smile.

"I guess you've made up your mind," Shirley thought but didn't say. At this point, she was sure any words would break the mood.

She lifted her leg higher, placing the flat of her shoeless foot on his leg, inviting him to explore even higher. Never having had a steady girlfriend, Shirley was willing to bet that whatever sexual experience Bobby had, it had been limited to short, rushed encounters. What a boy his age really needed was someone willing to take the time to let him explore, to delve into the mysteries of the female body.

That thought had also answered her own question as to why this boy interested her so. Despite over three decades of sexual adventures, that was something she had never done. All of her lovers along the way, with the exception of Morty, had been experienced. In his case, she had known even less than he did. The idea of educating this young man excited her as few things had done for a long, long time.

A spark flashed between her legs as she felt Bobby's hand brush across her already damp panties. His fingers rested there for a moment, feeling the wetness. She flashed him a warm smile, letting him know that he could do whatever he wanted.

Bobby slid his hand back from under her dress, working his way back down Shirley's leg. The older woman turned around and sat on his lap, pressing the cheeks of her ass against his excited cock. Back and forth she moved, inviting him to explore the rest of her body.

An invitation Bobby eagerly accepted as his hand reached up and cupped her breasts, even as Shirley leaned back to meet his lips with her own. Her kiss was soft, yet full of fire. A passionate touch that Bobby had little to compare it to.

Her tongue worked its way deep into his mouth, filling him with even greater excitement. An arousal that more than doubled as Shirley undid the small clasp holding up the top of her dress. The blue material fell loose, exposing the pale blue bra that held her abounding mounds. The sight of the deep richness of her valley, coupled with the weight of her body against his cock, was almost enough to bring him to a premature climax.

Shirley was far too experienced to let that happen, and pulled back just enough to let his passions cool. She lifted herself off him, turning around to give him a deep hug, her breasts pressing hard against his chest.

Bobby grabbed the cheeks of her ass with both hands, lifting her dress up around her waist, exposing panties and a garter belt that matched her bra. His fingers ran across the smooth material undoing the snaps of her belt, slipping her undergarment down her legs. Shirley gave him a brief glimpse of her treasure as she moved, just enough to renew his desire.

Taking his hand in hers, Shirley led him from the couch, into the main bedroom, then to the large oversized bed. Sitting down on the edge, the dark-haired woman undid her bra and slid it down along her arms. Bobby's eyes opened wide at the now unrestricted view of her breasts, his gaze centering on the dark two inch circles that radiated out from the biggest nipples he'd ever seen. Years of reading his brother's Penthouse and Playboys had never shown him anything close.

Bobby pressed the flat of each hand against her rounded globes, rubbing his thumbs against Shirley's nipples. A loud, long moan slipped from her lips, spurred on by a tiny wave of delight washing across her chest. He continued to play with the supple flesh, feeling the rising warmth of her body.

Not content to just encourage him verbally, Shirley slipped her right hand between his legs, massaging the prominent bulge between them. Bobby responded with a loud cry of his own, one filled with the promise of the wonders to come. His measure became apparent as she brought a second hand into play, a length and width that filled her own face with anticipation.

Leaning back onto the bed, she pulled Bobby closer and spread her legs wide, giving the younger man a longer, totally clear view of her pussy. She worried for a moment that her bush, which, unlike the hair on her head, was totally gray, might remind him of her age and turn him off. She needn't have worried because at this point, the color barely registered to him. Her concern faded immediately, washed away by the look of wonderment on his face.

Shirley turned over onto all fours, lifting her bottom until it was only a foot away from Bobby, displaying her sex once more. Bobby eagerly reached out with both hands and spread her cheeks, exposing his prize even more. Dropping to his knees, he brought his head even closer, extending his tongue until it brushed against the outer walls of her core.

He paused for a heartbeat, taking it all in. Ever since he'd first become aware of the differences between men and women, he'd wondered what it would be like to taste that sweet nectar. He remembered all the stories guys in school used to pass around about eating pussy, but none of his friends had ever actually done it. At least, not outside of their dreams.

Well this was no dream, as the strong scent of womanhood filling his nostrils readily attested. He moved just a little bit closer, pressing his tongue between the folds to slide far inside. He was almost overwhelmed by the taste and smell of the mature woman, an ambrosia that colored his own many dreams of what it might be like. Unsure of what exactly he should do, now that the reality was upon him, the only thing he was totally sure of was that he wasn't about to stop.

"Oh yes," Shirley called to him over her shoulder, the wetness of his tongue colliding with her. "Right there, just keep doing it right there,"

Bobby followed her instruction, not exactly sure of what he was doing. That didn't seem to matter though, because whatever it was, Shirley was obviously enjoying it. He tried to concentrate his efforts on the spot she directed him to, but kept losing his way. At her suggestion, he used his hands to part the way even more, giving him more room to work his way inside her. In no time at all, Shirley's moans become even louder, assuring him that he was indeed doing it better.

"That's it, baby, you're doing fine," she offered between cries of pleasure, "push that tongue deep into my pussy."

Bobby's lesson in cunnilingus went on for a while longer. Shirley offered an occasional helpful word of advice, but for the most part was content just to enjoy the ride. The neophyte muff diver might not have the skill of the lovers she was used to, but she couldn't fault him for his willingness to learn.

Eventually, it was time to move on to other delights and Shirley disengaged herself and climbed off the bed. She let Bobby help her out of her dress and she stood before him clad in only her stockings and garter belt. He seemed so fascinated by the relics of another generation that she decided to leave them on.

From behind her, Bobby again closed his hands on her breasts, squeezing her flesh and playing with the rigid nipples, working them between his fingers. Shirley turned so that he could play with them easier from the front, then guided his mouth to the center of her left mound. She moaned appreciatively as his lips closed around the long tip, his tongue rubbing against it to produce tiny sparks that grew in intensity with each breath.

Bobby soon moved to her other breast, copying his actions at the first. Again the reality of many nights dreams filled him with pleasures that, duplicated the delights his attentions were bringing Shirley. Back and forth he went, using both his mouth and hands to their full effect.

Releasing his hold on her breasts, Bobby worked his way back downward until once again he was between her legs. Shirley stepped back and then sat again on the bed. The twenty-one year old wasted no time as he followed her down, spreading her legs wide to given him even easier access than before. He parted the folds of her sex with his fingers and immediately returned to the ministrations that had brought them both such pleasures before.

Pleasures that washed over Shirley's body, to combine with secondary joys that she was producing as she played with her own breasts. Familiar with every inch of her flesh, she brought forth a warm satisfaction that Bobby couldn't equal. Still, as before, she gave him extra points for effort, especially as it was obvious that he was already applying the lessons he'd learned only a short while before.

Shirley lifted her legs high into the air, tilting them back and grabbing hold of them to give Bobby more room. It was obvious that, despite his inexperience, the young man took to cunnilingus like he'd been doing it for years. It was a talent that the older woman knew would serve him well as he journeyed through life.

But the aspect of that journey that concerned her most right now was the road that led them both to orgasm. She released her legs and dropped one hand until it came to rest against the back of his head. She guided his efforts for a few minutes more, savoring their effects, then gently lifted him up and away from his erotic repast.

She guided Bobby back to his feet, as she moved up into a sitting position. Her attention now focused once more on the prominence inside his pants, her fingers pulled down his zipper and pushed aside the underpants behind it. She leaned inward and kissed the hard flesh now exposed, then reached in with her fingers and pulled it free.

Her earlier guess about Bobby's size proved pretty accurate, but then she'd had decades to refine that particular talent. Closing her hand around his shaft, Shirley slowly ran her fingers up and down his length. The brush of her skin against his sent ripples up and down Bobby. Ripples that transformed into powerful waves as she again moved in closer and took him into her mouth.

"Omigod!" Bobby gasped as he felt his cock engulfed by her wet mouth.

It wasn't the first time he'd gotten a blow job, Suzie had certainly been willing enough to suck his cock. As had the hooker his friends set him up with. He might not remember all the details from that night but he remembered that much. Neither of those experiences compared to what he was feeling now.

Suzie had gone down on him for the purpose of getting him hard, not that he'd needed much in that area once she'd started taking off her clothes. Once she was satisfied he was ready to please her, she'd quickly moved on and climbed on top of him. From what he remembered of his first experience, it hadn't even lasted that long.

Shirley, on the other hand, or should that be mouth he found himself thinking, seemed in no hurry at all. Her tongue moved up and down his length with precision thrusts, tickling his flesh with its tip, sending tiny cascading waves up into and throughout his body. She took him whole, then slowly pulled back, sliding his hardness between her lips. Only to press forward once more.

Her hand cupped his balls, massaging that soft flesh, alternating her touch with a wet and warm envelopment as her mouth moved past his length to alternately take each of them inside her. Shirley's attention then split as she worked her way back upward, one hand continuing to play with his balls while the other dropped down between her own legs. The press of his hardness in her mouth muffled her soft cry as her fingers followed a well-worn path.

"Oh God, oh God!" Bobby kept repeating as every inch of his body came alive in erotic rapture.

Bobby had first thought he was going to pass out as Shirley wrapped her lips around his cock, but he soon calmed down enough to just relax and enjoy the wondrous sensations. Shirley's heart rate however seemed to double as her fingers continued to play between her legs, even as she took him deeper into her throat. Her head bobbed up and down on his hardness, her tongue swirling in every direction, covering every inch of his sensitive skin.

Bobby felt his heart begin to race as well as sensations that had first manifested in his early teens when he discovered self-pleasure asserted themselves. He knew he was nearing his limit and was going to explode much sooner than later.

"I... I'm going to come," he panted out, remembering that not coming in their mouth was one thing he clearly remembered both Suzie and the hooker warning him about.

At first, Bobby thought Shirley hadn't heard him as she worked even harder on his cock with her lips and tongue, driving him even wilder with pleasure. He felt the orgasm building uncontrollably inside him and repeated his warning with such intensity that the older woman couldn't ignore it.