Jackpot

by Ann Douglas

Copyright© 2004 by Ann Douglas. All rights reserved.

Erotica Sex Story: On a trip to Atlantic City, Bobby Harrison learned that not all jackpots were won in the casinos

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Fiction   Oral Sex   .

"Hey Kid," Chuck Michaels called out from the other side of the seemingly endless row of slot machines, "you having a good time?"

Bobby Harrison turned in the direction of the familiar voice, giving a friendly wave in response to the inquiry before quickly disappearing down the row. The twenty-one year old really hated it when his co-workers called him "Kid", even though there was some truth to it since the majority of them were much older than him.

Once he was sure he was out of sight of his friend, Bobby turned his thoughts back to the matter at hand. His friendly wave to the contrary, he was having a lousy time. That was pretty hard to do considering he was on an all expenses paid trip to Atlantic City. But even so, he couldn't wait until the bus was headed back to New York tomorrow night.

These feelings hadn't been there a month ago when his boss had called him into his office and told him he'd been picked as one of the Employees of the Year for 1994. He'd been full of pride and excitement then, winning an award that only six others did, all of them with a lot more time at the firm.

That enthusiasm, however, had begun to fade a two weeks ago when he'd finally persuaded Caroline Kelly, one of his neighbors, to go along on the trip with him. He and the twenty-three year old brunette had gone out a few times, with mixed results. Their relationship had been friendly enough, but friendship seemed to be as far as she wanted to take it.

"I'd be happy to go with you," Caroline had said when Bobby had asked her to come along, "but I just want to make one thing real clear. If there aren't two beds in the hotel room, one of us is going to be sleeping on the couch."

Even with that disappointing precondition, Bobby was glad that she was going with him. Truth be told, his luck with the ladies wasn't all that great. He wasn't a virgin, thankfully. That was something he couldn't have dealt with only two months after his twenty-first birthday. Being the only single on the trip would've been too much to take, he'd thought.

Not that he ever shared it anyone else, but his two previous sexual experiences really hadn't added up to all that much. One had been with a professional, right after his eighteenth birthday. The guys on his first job had taken him out to a brothel one of them knew about as a belated gift. Bobby had been so drunk that he barely remembered losing his cherry.

The other occasion had been with Suzie Clancy, a girl his older brother had set him up with. It was pretty common belief among the guys in the neighborhood that a guy would have to be totally queer not to score with Suzie. Still, even with that in mind, Bobby spent most of their date worrying that he'd somehow be found wanting. In the end, Suzie hadn't disappointed him, but the brief incident in the back of his Dad's borrowed car was memorable only in that he actually remembered it.

What excitement that still remained for the trip to Atlantic City, faded even before the bus left the company's parking lot in Queens. He was just about to walk around the corner to pick up Caroline when she called and said that she couldn't go after all. Her supervisor at the hospital where she worked as a Nurse's Aide needed her to cancel the three days off she had taken and fill in for another Aide who had broken her leg. She was sorry of course, Caroline had said, but she couldn't turn down the request. Not with her quarterly review coming up, not to mention the promotion she was trying to get.

Bobby had lied and said that of course he understood. What he really was thinking was that it was too late for him to cancel his own place on the trip. Just before Caroline had called, he'd just gotten off the phone with Chuck to confirm that he and his wife were stopping by to pick up him and Caroline. Reluctantly, he put on his best face and climbed into the car alone when it pulled up in front of his house.

The two and a half-hour trip to the casino/hotel turned out to be not as bad as Bobby imagined it might be. No one made jokes about his suddenly going stag. In fact, two of the wives commented that he'd probably have more fun that way since the resort area was full of beautiful women and a cute guy like him wouldn't have any problem meeting someone to spend time with.

So many people had told Bobby that he was cute that he sometimes almost believed them. The dark haired young man stood five seven and weighed a hundred and forty-two pounds. He had a face that had changed little since his early teens, so much so that he was constantly being carded. His only real problem seemed to be an inability to overcome a sometimes almost incapacitating shyness around women. A shyness that hid his more attractive qualities.

The camaraderie Bobby enjoyed on the bus slowly faded over the next day and a half as the small group attended the scheduled company functions and got their awards. No one really acted any differently toward him, in fact, the Michaels and one of the other couples asked him to tag along when the last scheduled event was over. Bobby had politely declined because he never liked being a third, or in this case fifth wheel.


With the Employee Awards had come two hundred dollars for the honorees to gamble with. Not really understanding most of the games of chance, Bobby had most of it converted to coins and played the slot machines. It was as good a way as any to pass the time, he thought, at least better than sitting up in his room alone and watching cable television. For a while, he was even winning more than losing, but that soon changed. Eventually, he was down to his last silver dollar.

"Well at least it wasn't my money I was playing with," Bobby thought as he pocketed the last coin, deciding to keep it as a souvenir.

His play money now gone, Bobby decided that maybe catching a late movie on the tube might not be a bad end to the night after all. Leaving behind the slot machine he'd been playing, Bobby started to make his way to the bank of elevators outside the casino. He'd just about cleared the end of the row when he heard someone call out.

"Oh shit," a dark haired woman sitting at the oversized multi-coin slot machine cried out as she looked down at her near empty coin bucket. "I could've sworn that I had another dollar left."

Thinking at first that the woman in the blue dress had been talking to him, Bobby had stopped and looked at the machine she was playing. It was one of those Progressive Slots where you put in multiple coins, the payoff being a lot larger than the ordinary slots. Of course the odds were greater too. This machine in particular required ten silver dollars for a chance at the big prize, and the lady evidently only had nine.

"Damn, I promised my granddaughter that I'd play this for her before we headed home," the woman who Bobby now realized was talking to a blonde-haired woman who had been standing behind Bobby as he walked by. "You wouldn't happen to have a dollar left, would you Golda?"

"Sorry, Shirley," Golda said with a shrug, "they don't call these things one armed bandits for nothing. I'm totally tapped out. I guess you're just going to have to settle for second prize when you hit."

From the inflection in the second woman's voice, Bobby was pretty sure that Shirley hadn't ever come close to any prize on that machine, much less second, in all the times she'd played it. Still, he supposed it was making the attempt that mattered to the first woman, not if she actually won anything.

Without even thinking about it, which was of course was when he was at his best, Bobby reached into his pocket and pulled out his souvenir dollar. He took a step closer to the slot machine and caught the dark haired woman's attention as she put her first coin into the machine.

"Excuse me, Ma'am," he said as he held out the palm of his hand, the dollar in the center, as way of why he was interrupting her. "This probably means more to you than it ever would to me as a souvenir. I'd be happy if you'd use it."

"Why thank you, young man," Shirley said, her face lighting up in both surprise and gratitude. "It's nice to see that there are still knights in shining armor to come to a lady's rescue."

As Shirley took the coin from his hand, Bobby got a much better look at the older woman. Her hair was darker than his, but in an age of better living through chemistry, that didn't mean anything. If he had to guess, and he was notoriously bad at that, he'd say that she was about his mother's age,. Certainly she wasn't as old as his own grandmother, who was fifty-nine. It would come as a real shock to him to learn that she was in actuality a month short of her sixty-first birthday. A lifetime of taking care of herself had kept the worst effects of age at bay.

Turning around to face him had also given Bobby a better view of a quite impressive chest. She looked as big as Mrs. Turtledove who had lived next door when he was growing up. Once, on a dare, he had sneaked into her backyard and stolen a brassiere off the clothesline. He remembered examining it with his friends and reading the size off the little white tag. It had been a 38D.

Lost in that memory for a moment, Bobby totally missed the older woman's thank you as she smiled at him one last time before turning back to the machine. One by one, she dropped the coins into the machine, savoring the sound of each one dropping as an almost religious experience.

Glad that he had done something good for someone, Bobby turned and walked away, reaching the elevators before Shirley was even up to the fifth dollar. It was better, he thought, to remember how her face had lit up when he'd handed her that dollar than watching her disappointment when the machine came up empty once more.

"Sorry, the elevators are temporally out of service," one of the hotel workers told him as he reached for the closest call button. "One of the fire alarm bells went off on the third floor and everything has to be reset," he explained. "It shouldn't take more than a few minutes."

"What the hell," Bobby thought, deciding that maybe the movie wasn't a great idea after all. "maybe I'll just go for a walk down by the water."

He'd just turned in the opposite direction when some kind of commotion broke out behind him. A number of people ran past him to see what was going on, but he wasn't interested. He'd had enough of the noise of the casino for the night.

Ignoring the obvious excitement, he just about made it to the lobby door when a loud voice called out to him. He didn't recognize it, but the sheer volume of it made him come to a complete stop.

"Hold it right there, young man!" the booming voice cried out. "Don't you go one step further!"

Worried that he'd done something wrong, Bobby turned around and was surprised to see the woman from the slot machine barreling toward him. And barreling was indeed the word as the stocky five foot four woman looked loaded for bear.

"Did I do something wrong?" he stuttered, his awkwardness kicking in automatically.

"Wrong?" Shirley laughed as she came to a sudden stop just short of knocking him over. "Honey, you couldn't have done anything more right."

"Huh?"

"We won!" the buxom woman beamed. "We hit the jackpot!"

"We won?" Bobby repeated, still a little confused.

"Fifty thousand dollars," Shirley exclaimed, "and the way I see it, five thousand of that is yours."

"Oh wow!" Bobby said as understanding finally sunk in.


Two of the casino officials helped clear a path trough the crowd so that Shirley could talk to Bobby in a quieter setting. Once in the office, they cut two checks, one made out in his name for five thousand dollars, the other in Shirley's for the remainder of the prize. He still couldn't believe the older woman's generosity.

"We will also make available a line of credit for the both of you equal to your winnings if you'd care to continue to play," the well-dressed man who had produced the checks said and introduced himself as Mr. Rourke, his tone almost reflecting the hope that they'd go right out and lose what they'd won.

"It's been a real long day and to tell the truth, my friends and I were about to head home in a little while," Shirley offered, knowing exactly what he was trying to get her to do. "Our bus is heading back in about an hour in fact."

"If you wish," the gentleman continued, not willing to give up that easy and let her walk out with so much of the casino's money, "we would be happy to arrange a complimentary suite so that you could stay overnight, as well as make arrangements with your tour to have a place for you on tomorrow's bus."

Shirley briefly considered pointing out that if they really wanted to convince her, they'd arrange for a limousine to drive her back to New York. But she realized that it was their hope that she'd be leaving all of her winnings behind and would be happy for a place on the bus. She was hardly the innocent they took her for, but she saw some advantages to taking them up on at least part of their offer.

"What do you say, Kid," Shirley asked Bobby, turning her attention for the moment away from the Casino Manager, "Would you like to spend the night in a fancy suite?"

"Me?" Bobby replied, not evening noticing that she'd called him Kid.

"Sure, like I said before, I wouldn't have gotten any of this if it weren't for you."

"There are of course, two bedrooms in the suite," Mr. Rourke interjected, trying to make the idea seem more appealing to the younger man. The room cost the hotel nothing since it hadn't been rented for the weekend, and he was sure if they stayed so would their money by the time they were ready to leave.

Bobby thought about it for a few moments. The room the company had paid for was nice enough, but certainly nothing what a suite must be like. This might be the only time in his life that he'd be able to stay in one.

"I think that might be great," Bobby finally said.

"Excellent," Mr. Rourke said, "give me a few minutes to make the arrangements."

While he went off to do just that, Shirley stepped over to Bobby and stretched out her hand. "I don't think we've actually been introduced," she said with a smile. "I'm Shirley Klein."

"Bobby Harrison," he replied as he took her hand and returned the smile.

"So are you here with someone, Bobby," Shirley asked as she brought back her hand. "a young lady perhaps?"

"No, nothing like that," he replied, feeling a little of his awkwardness kicking in. "I was hoping I was going to be, but it didn't work out that way."

Seeing the puzzled look on Shirley's face, Bobby went on to explain that he was here with his company for the award dinner, and how his date canceled at the last minute.

"Well it was certainly her loss," Shirley smiled. "I can't imagine any young lady giving up the chance to spend time with a fine gentleman as yourself."

Bobby blushed with embarrassment at the remark.

"Well can I at least offer my congratulations for winning your award," Shirley said when she saw her reaction. "It's nice to see someone rewarded for their efforts."

"Thank you," came Bobby's reply.

"The room will ready in fifteen minutes," Mr. Rourke said as he returned from making a quick phone call. "Shall I have someone assist you in moving your things?"

"My things are what I have on," Shirley grinned, "this wasn't planned as an overnight trip."

Rourke's eyes turned to Bobby, silently asking the same question.

"I just have one bag," he replied. "I'll take care of it myself."

"Very well," the older man said as he handled each of them a key to the suite.

"I just have to go tell my girlfriend that I'm going to be staying the night," Shirley said to Bobby as she ran her fingers over the key, taking note of the room number. "What say you get your bag and meet me up there?"

"Okay," Bobby said, having totally forgotten for the moment the other woman that had been with Shirley at the slot machine. He wondered why she wasn't asking her to stay in the suite as well since as Mr. Rourke had said, there were two bedrooms. Well he concluded, that was her business.

Since he hadn't really unpacked his bag in the first place, it took only a few minutes to gather up his things from the bathroom. He wondered if he should call someone and let them know he was changing rooms, then decided not to. His boss had said, when the award ceremony ended, that they were on their own after that. All he asked was that they be at the bus when it was ready to leave. The traffic was going to be bad enough and he didn't want to get a late start. Locking the door behind him, he headed to the elevator and hit the button for the next to top floor.


The elevator doors opened to reveal only three rooms on the floor. Checking his key against the room number, Bobby turned to the one on his left and tried it. He opened the door halfway, then decided that he should make his presence known first.

"Hello?" he called out, waiting for an answer before opening the door the rest of the way.

"Come on in, Bobby," Shirley replied from inside. "I'm decent enough," she joked.

At least Bobby realized that it was a joke when he hesitantly stepped into the suite and saw Shirley standing in the center of it, dressed just as he'd left her a little while before.

"Pretty impressive, isn't it?" She said with a wave of her hand as she indicated where he could put down his bag.

Impressive wasn't the word. As she gave him a quick tour of the room she had only arrived at ten minutes before, Bobby found that the second bedroom, normally used for a personal maid, was as large as the room he'd just vacated. The entire suite, consisting of a living room, two bedrooms and an oversized bath was larger than the apartment he'd grown up in.

"And look what they were nice enough to send up for us," Shirley added as Bobby emerged from the second bedroom.

Sitting on the table of the living room was a basket filled with cheese and crackers along with a bottle of champagne set in ice. Shirley cracked open the bottle and poured them each a glass.

"You are old enough to drink, aren't you?" she asked, taking note of his more than youthful features.

"I'm twenty-one," he replied.

"I thought you were that old at least, seeing as you were in the casino," Shirley said as she handed him one of the glasses, "but I just wanted to be sure. I'd hate to be accused of corrupting the morals of a minor." She laughed.

Bobby had only had champagne once before, at his brother's wedding. He remembered it as having made him feel light-headed and this bottle proved to be no exception. He drained the glass and had it almost immediately refilled by Shirley.

"This place is even more impressive than the place I spent my honeymoon in," Shirley commented after refilling her own glass and putting the bottle back in the iced bucket, "but that was many years ago."

It hadn't occurred to Bobby that there might be a Mr. Klein. Putting his half empty glass down so that he didn't drain it as quickly as the first, he asked if her husband had stayed at home.

"You could sort of say that," Shirley said, taking another large sip of her drink, then alternating it with a piece of cheese on a cracker. "Morty passed away a long time ago."

"You never remarried?" Bobby asked as he followed her example, thinking that his own grandmother had done just that, and her husband had only died five years ago.

"I already had my children, and I really never found someone I loved as much as Morty," she explained.

"I can't imagine spending my life alone," Bobby noted, taking more of the champagne as she topped off his glass once more.

"I never said I was alone."

Before he could ask what exactly that meant, Shirley changed the subject.

"This girl that was supposed to come with you, she your girlfriend?"

"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.

 
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