Jimmy's Luck

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Jimmy gets lucky - and mom's part of the luck!
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TryAnything
TryAnything
9,297 Followers

Jimmy's eyes almost popped out of his head when he saw the numbers for that week's Lotto drawing on the evening news. He had been playing the Lotto for the past 2 years, ever since he had turned 16 and gotten his first job. He had played faithfully every week, never winning so much as a penny. Until now, he thought. But he was seeing it on the television, the very numbers that he played each and every week, 1, 2, 3, 5, 8, 13, a Fibonacci progression.

Jimmy glanced over at his mother. As usual she had fallen asleep, sprawled in her favorite recliner. She worked a double shift as a waitress at the local IHOP every day, breakfast and lunch, and it wore her out. She would come home, take a shower, put on her favorite house robe, make dinner, and then fall asleep in front of the television.

Jimmy liked it when she fell asleep. For the past year he had been achingly aware of how beautiful she was, even though she was now 37, almost ancient by his newly mature standards. But many evenings, like this one, he would be rewarded by her robe becoming loosened by her moving around in the recliner and he would be able to see one, sometimes both of her breasts. And they were something to behold. Jimmy knew from going through the laundry that they were 38D in size, and he knew from having seen them that she had huge dark nipples twice the size of silver dollars.

Jimmy wanted to fuck his mother in the worst way, he just didn't know what to do. Of course he was afraid of her reaction. Would she think him a disgusting pervert and throw him out of the house? Would she hate him forever? He knew she hadn't dated anyone in years, having to work herself to death in order to support them. Now that Jimmy was working full time as a lifeguard at the beach, he was able to contribute to their meager funds and take some of the load off of her.

But now. Yes, what about now, he thought as he pulled his wallet from his pants pocket and extracted the Lotto ticket that he always kept in the same place. Yes, he was right, 1, 2, 3, 5, 8, 13. This week the jackpot was up to $13.4 million. Even after taxes he'd have over $7 million. All of his worries were over. And his mother's. The thought of being able to take care of her, enable her to quit her job, that filled him with pride and brought tears to his eyes.

But he'd find out all about that tomorrow, first thing, he thought. Now he had to get his mother upstairs to bed.

Quietly getting to his feet and going over to where she was sprawled in the recliner, Jimmy shook her shoulder to wake her, using the movement and opportunity to pull her robe completely open and expose her body. He sucked in his breath as he looked at her, her full breasts rising with her breath on her chest, and still the biggest surprise of all to him, especially in lieu of the fact that she never dated, her baby-smooth pussy, not a hair to be seen anywhere, just a pair of thick, fat pussy lips between which protruded a full inch of her inner pussy lips with the nub of her clit poking out above them.

"Oh, Jimmy, I must have fallen asleep," Judy Lawson said, automatically and instinctively pulling her robe closed about herself as she sat up. "What time is it?"

"You need to get to bed, mom," Jimmy told her. "It's late."

"Yes, tomorrow will be here before I know it," she sighed as she got to her feet.

"I sure wish you didn't work so hard, mom," Jimmy said to her. "Or work at all."

"Me, too, Jimmy," Judy said, reaching up and pulling his head down and kissing him on the side of the mouth. "But until someone gives me a million dollars, I don't really have a choice, do I?"

"So if I gave you a million dollars, you'd quit your job?" Jimmy asked with a laugh.

"I'd do anything you wanted me to do," she laughed.

"Anything?" Jimmy asked, looking at her sideways. "You're a beautiful woman and I've got a very active imagination," he said to her.

"Oh, Jimmy, you do know how to make an old woman feel good," she laughed, heading towards her bedroom.

"You're not old, mom," Jimmy assured her, "you're just not as young as me anymore."

"Good-night, Jimmy," she said.

Jimmy just stood there until he heard the bead curtain that doubled as her bedroom door swish as she went through it. His cock was rock hard in his pants and he almost ran to his room to get to his computer. Stroking his 8" cock as he logged on to his favorite porn site, a webcam belonging to a woman who was remarkably similar in build and looks to his mother, Jimmy once more pictured his mother sprawled in her recliner as he watched the woman on the webcam working a huge dildo in and out of her pussy. Before he knew it, his cock was erupting, cum shooting up to splash on his chest and stomach. By the time he finished cumming, his fist was covered in his cum and it was dripping down onto his seat.

Because he was a big, muscular, good-looking guy, Jimmy never really had any trouble finding girls. And his job as a lifeguard on the most popular beach in the area made it even easier. At 6'4" and 220lbs, Jimmy's tanned and chiseled body was an easy magnet for the girls. And even though he got his fair share of pussy, he invariably found himself picturing his mother writhing beneath him as he fucked the current lucky girl.

Having cleaned himself up, Jimmy peeked through the bead curtain that was the door to his mother's bedroom before going into his own room for the night. The sight of her curled up beneath the blankets with one bare foot and leg sticking out almost made him groan with desire.

Laying down in his own bed, Jimmy began to plan his coming day, the thoughts of the millions of dollars making it almost impossible to go to sleep. When he finally woke up the following morning, it was to the sensation of his mother saying good-bye and kissing him on the forehead. Sitting up, Jimmy was aware of the fact that his cock was rock hard and was sticking straight up, tenting the sheet.

"Bye, mom," he said to her. "I hope you have a nice day."

"You, too, Jimmy," Judy answered her beautiful son, not unaware of his 'problem' poking up beneath the sheet.

As soon as Jimmy heard the door close, his fist was wrapped around his cock and he was stroking it for all it was worth, not stopping until he was rewarded with several nice, thick ropey squirts of cum. Not wanting to have to clean up a big mess, he caught it in his hand, feeling the heat of his seed and wishing it was his mother who was receiving it.

After taking a shower and getting dressed, Jimmy drove into town to the local Lotto office where he had his winning ticket validated. After a couple of hours of formalities, Jimmy had a check in his hand for $7,650,000. His legs were shaking so hard he had trouble driving to his bank. After making his deposit and getting a cashier's check for $1,000,000 made out to his mother, Jimmy drove to the newest ocean-side gated community that had just been completed.

Two hours later, after some very serious haggling, Jimmy left, the proud owner of a luxurious, brand-new, ground-level, 2-bedroom oceanfront condominium. He then drove home to await the moving van which he had insisted on as a condition of purchase. He wanted to have everything moved out before his mother got home from work.

Once he looked at their things, he decided that they wouldn't need most of it and had the movers only take their clothes and some personal things, leaving only his mother's robe and a small bath towel hanging in the bathroom. He then went to a modern furniture store and bought enough to fill the new place, paying a nice personal premium to the on-duty manager for immediate delivery and setup. Next stop was Crate & Barrel where he stocked the kitchen & dining room with service for 8.

He had only just made it back to their apartment when his mother arrived home from work, a bone-tired look of exhaustion on her face. Seeing Jimmy, her face brightened and she wrapped her arms around his neck and hugged him, kissing him on the cheek.

"The best part of my day is coming home and having you here," she told him, slumping into a chair at the dining room table.

"How about a glass of wine, mom?" Jimmy asked.

"That would be wonderful," Judy answered, smiling her appreciation at him.

"You go get in the shower," he said to her, "and I'll bring it to you."

"Jimmy, you're such a dear," she laughed. "You're always thinking of me."

"Well, you've sure paid your dues," Jimmy observed as she got to her feet. "It's nice to pay you back in whatever way I can."

"Thanks, sweetheart," she said, stroking his cheek with the palm of her hand as she went to the shower.

Jimmy's heart was pounding as he opened the bottle of wine and poured a glass for his mother, taking the liberty of a long hard swallow right from the bottle for himself. Going towards the shower, he deliberately waited until he heard the water shut off and the sound of the shower curtain being pulled aside before knocking and at the same time opening the door, the glass of wine in his hand.

As planned, he caught his mother just stepping out of the shower, dripping wet and very naked.

"Oh! Jimmy," she said, blushing as she realized that she was naked in front of him.

"Here's your wine," Jimmy said, holding the glass out to her, his eyes taking in her beautiful body.

"Oh, thank you," she said, feeling her nipples hardening into the huge knots that they became when she was excited as she reached for the glass with one hand and the towel with the other. "Mmm, nice," she said after taking a sip, holding the towel up against herself, barely covering her breasts and pussy.

His entire body aching with desire, Jimmy turned and went back into the kitchen to wait for his mother. Just like every evening, she returned wearing her house robe, her glass of wine in her hand, though it was almost empty.

"I'll get dinner ready," she said, going to the refrigerator and opening it and stopping, her mouth dropping open in surprise.

"Jimmy, what happened to all of the food?" she asked, turning to look at him.

"Oh, I threw it away," Jimmy said, seeing the color drain from her face and feeling guilty. "But I planned on taking you out to dinner," he said.

"But Jimmy, we can't afford that," she almost cried. "We can't afford to have all of that food thrown away, either."

"It'll be okay," Jimmy assured her. "Let's go, though."

"Let me change first," Judy said, draining her glass and going to her bedroom.

"Jimmy!" he heard her cry out. "Where are all of my things?" she cried. "What have you done?"

"I've just moved them, mom," Jimmy told her. "It's okay, I promise."

"But my clothes!" she wailed, tears forming in her eyes.

"Mom, I'll take you to your clothes right now," Jimmy said, feeling sick to his stomach at causing her to feel so upset.

"But I'm in my house robe," she sobbed.

"It's okay, nobody will see you if you're in the car," he told her. "Come on, I'll take you right now."

Judy was silent as they drove, holding the robe clutched tightly against herself. She didn't know what was happening and she was very confused. Jimmy was usually the most logical and rational of boys, but now he was frightening her.

When he turned the car into the new Breakers condominium and the security guard waved hello and let them through, Judy looked at her son.

"Jimmy, what is going on?" she asked. "You're behaving very strangely."

"I know, mom, but just another minute and you'll understand," he told her, casting her an imploring look.

Judy just sat back, not having any idea of what to expect. Her surprise increased when Jimmy produced a remote control and a garage door opened in front of them, into which he drove the car, parking it and closing the garage door behind them.

"Come on, mom," he said, getting out of the car.

"Jimmy, whose house is this?" she asked, almost in a whisper.

"You'll see," he told her. "It's okay, there's nobody here."

"Jimmy, are we going to get into trouble?" she asked.

"No, mom, we're not," he replied. "It's okay."

They stepped into the house and Judy gasped. Everything was new and beautiful. It looked like some luxurious showroom.

"Jimmy, what is this?" she asked.

"Here," he said, handing her an envelope.

Totally confused, Judy opened the envelope and extracted the check inside. She read it once, looked up at him with her mouth hanging open, then looked at it again.

"Jimmy, this can't possibly be real," she stammered.

"It's real, mom, and it's yours. All of it," he told her, a smile on his face. "And this house is mine. It's paid for. This is where we're going to live from now on. And you're not going back to work. And neither am I."

"But Jimmy, how is this possible?" Judy asked, looking around.

"Remember what you said yesterday," he asked her. "You said you'd do anything for a million dollars. Well, there's your million dollars."

"And what do you want me to do for this million dollars?" she asked him.

"Let me take care of you," he said. "And you take care of me, too."

"But Jimmy, how can I..." she began as the doorbell rang.

"I'll get it," Jimmy said, turning to the door.

"Mr. Lawson?"

"Yes," Jimmy replied.

"We're here for the massages."

"Wonderful. Please come in," he said, standing aside to allow them in.

"Oh!" Judy exclaimed when she saw them enter the room.

"Ready to get a massage?" Jimmy asked, a smile on his face at the look of astonishment on his mother's face, for the two masseurs were both coal black with finely chiseled features. Their skin was so ebony in color that it fairly glowed and they were both firmly muscular

"Where would you like us to set up?" the man asked. "I'm Ugado and this is Amari," he said, introducing them.

"I'm Jimmy and this is Judy," Jimmy replied before his mother could speak. "Why don't we do it out on the patio," he suggested, turning to lead the way.

Judy could only follow speechless, herself not having any idea of the layout of the house yet. She gasped when she saw the patio was a screened patio with a nice, intimate swimming pool with a Jacuzzi hot tub next to it. Outside the patio was the beach and the ocean.

"This is a perfect setting for a massage," Ugado said he began to set their table up.

"I've never seen a massage table like that," Judy observed.

"Yes, it's an extra-wide table, specially built for doing couples massages," Ugado explained. "If you please," Ugado said, holding out his hand towards the table when he had it set up. "Face down to start, please," he explained.

Feeling completely embarrassed, Judy let her robe slip from her shoulders. Ugado caught it and Judy lay down on the table on her stomach, acutely aware of the way Jimmy was looking at her and the fact that her nipples had hardened into knots before she could hide them by laying down.

She felt Jimmy getting onto the table next to her and then she felt the wonderful sensation of warm oil and large strong hands on her back and she relaxed. Judy drifted in and out of awareness as Ugado worked on her, relaxing her. This couldn't possibly be real, she thought as she gave in to the delicious sensations Ugado's hands were producing.

Glancing to her left, Judy saw that Jimmy was laying in the opposite direction, his feet opposite her head, and she could see that Amari was working on him while Ugado continued working on her.

Judy almost gasped out loud when she felt the warm oil being drizzled into the crack of her ass and she had to bite her tongue to avoid moaning out loud when she felt Ugado's huge, strong hands grip her ass cheeks, squeezing them and kneading them. But when his hand slid down the crack of her ass, one finger sliding easily into her soaking pussy, another gently pressing into her ass, Judy gasped, her pussy convulsing in a long overdue orgasm. She could feel Ugado adding one, two, three more fingers to her pussy as it clamped down on him, her juices flooding the table.

And then she stopped cumming and Ugado continued on down her legs, massaging them until she stopped trembling. She couldn't believe that she had just been brought off like that and with her son laying right next to her.

"Okay, time to turn you two over," Ugado said. "Better to put these eye covers on to protect you from the light. It will help you to relax, also," he explained as he handed Judy a silk eye mask.

Sitting up to put on the mask, Judy saw that Jimmy, too, was putting one on. What shocked her was seeing Amari's coal black hand wrapped around Jimmy's very hard and erect cock, slowly sliding up and down the shaft. Then her eye mask covered her eyes and she saw no more as Ugado gently helped her to lay back.

Her pussy was on fire as Ugado continued massaging her, paying special attention to her breasts whose nipples were harder than she ever remembered them being. He pinched and pulled them, sending sensations directly to her already sopping pussy.

Judy hadn't been sexually aroused in quite a few years. She just hadn't been able to afford the luxury of indulging herself, needing to work all of the time just to keep food on the table and clothes on their backs. The death of her husband in an accident had forced the harsh realities of life upon her and she hadn't been in the least bit prepared for them.

But now she was incredibly aroused. This complete stranger had gotten her off by playing with her pussy while she lay next to her equally naked son. She wondered if he had noticed as she remembered his beautiful hard cock in Amari's hand.

"Here, slide up a bit," Ugado said, gently pulling her arms up over her head.

With him helping, Judy slid up towards the head of the table, her head hanging over the edge yet supported by a face cradle which was lowered, allowing her head to hang back. As Ugado began to massage her neck, Judy was surprised when she felt a pair of hands begin to work on her lower legs, realizing that it must be Amari. She fleetingly wondered about Jimmy before giving in to the wonderful sensation of four hands on her body.

Then she felt the hands on her lower legs move to her upper legs, pushing her knees wide apart to work on her inner thighs. She knew she was completely exposed, but she was beyond caring as Ugado continued to work on her neck and chest at the same time.

Just as she felt her legs spread so wide that her feet slid off of the table, Judy moaned out loud as she felt what she knew was a tongue slide into her spread-open pussy. Instantly exploding into an orgasm, Judy arched her back and her mouth opened wide as she felt her pussy being devoured. At the same time, she felt her mouth being filled with a huge, hard cock.

Jimmy's eyes shined brightly as he watched his mother react to the now-changed massage. He could not get over how incredibly beautiful she was. When Amari had crawled up onto the table and pushed her knees up and apart, revealing her spread-open pussy to him for the first time, he had almost cum just from the sight of it. It had to be the most beautiful pussy he had ever seen.

When Amari lowered her face and stuck her tongue into Judy's pussy, Jimmy could take it no more and knelt behind her, driving his cock all the way in in one quick thrust, feeling the warm velvety smoothness of her pussy envelope him as she continued to eat his mother's pussy without interruption.

At the same time Jimmy had buried his raging cock in Amari's pussy, Ugado had released his cock from his pants and slid it into Judy's open, gaping mouth. As he continued to massage and pull on her breasts and nipples, Judy reached over and behind herself to fill her hands with Ugado's ass cheeks. As Jimmy watched in astonishment, Ugado's 10" of hard ebony cock slowly but surely disappeared into his mother's mouth, every single inch of it. He could see it bulging in her throat.

TryAnything
TryAnything
9,297 Followers