Hitting the Jackpot!

by Old Freak

Copyright© 2014 by Old Freak

Romantic Sex Story: Jack Gokker was a 45 year old man who built thick walls around himself following a very bitter divorce three years earlier. Little did he know when he walked into the casino that evening to play the penny slots, that his luck and his life would dramatically change for the better. If there is sufficient interest, I have some ideas for other stories involving these and other related characters that I may decide to explore in the future.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Consensual   Romantic   Fiction   Extra Sensory Perception   Mother   Daughter   Group Sex   Black Female   White Male   First   Oral Sex   Masturbation   Squirting   Cream Pie   Voyeurism   .

Jack Gokker smiled to himself, pleased that the parking lot wasn't very crowded as he pulled into a space near the entrance to the casino. Locking his car, he was hopeful that the luck he had in the parking lot would carry over to his coming adventures at the slot machines. Not knowing how lucky he would be that evening, Jack walked through the casino entrance and got onto the elevator which would take him to the casino floor.

Jack got off of the elevator and was greeted by the cacophony of sounds and flashing lights as he walked toward the casino floor. He stopped at the bill changing machine, converting a couple of twenties into five dollar bills, as he found that he was able to make sure he didn't spend too much money at one time on a machine that might just be hungry for his money and not willing to give him any kind of pay off for his bets.

Divorced for the previous three years and with a 17 year old daughter who he got to see every other weekend, Jack was fairly tall at just over six feet. Blessed with good genes, Jack looked younger than his 45 years of age, with a thick mane of light brown hair and a nice thick mustache of the same color, which several of his lady friends enjoyed riding to their mutual delight. Even though he was no body builder, Jack was in fairly good shape for a man in his mid forties. Because he hadn't been able to quit the habit yet, Jack walked through the non-smoking area and back toward where smoking was permitted, pleased that his first impressions he had in the parking lot about the lack of crowds still held. He stopped at the beverage dispenser and got himself a soda, then went back to find a machine he felt like playing.

Seeing the open seat, he sat down at the penny slot machine, inserting his membership card in its designated place, then putting a five into the slot set aside for deposits. As he did that, Jack said hello to the slender very attractive mocha colored woman sitting next to him. She gave him a big smile and greeted him, introducing herself as Keisha and wishing him luck. Jack told her his name and wished her luck as well.

Jack was hopeful that the results of his first spin were a sign of even better luck to come as he hit for $5 on a .30 cent bet. Keisha's luck on that spin was even better as she hit for a bonus of 25 free spins that paid triple her original bet during the bonus. With huge smiles on their faces, they turned toward each other and shook hands at their good luck so far. Keisha pressed the button to start the bonus, then reached into her purse and pulled out a cigarette. Jack saw her getting her smoke and reached into his pocket for his lighter, flicking it and teasingly saying to her, "Allow me to light your fire."

Smiling as she put the cigarette in her mouth, Keisha leaned toward Jack and lightly took his hand as she guided the lighter toward her smoke, lightly brushing her breast against his arm as she was doing so. She thanked him for the light, then looking him up and down, she said, "I think you just might be doing that."

Jack returned her gaze, checking out her sexy figure, noting that her outfit was sexy yet not slutty. He saw that she enhanced her figure with a top that just showed a hint of her cleavage, and a short skirt which showed off her legs to their greatest advantage. Jack had gone out with several black women in the past, both before he met his ex and since his divorce, so he had no problems appreciating Keisha's good looks and was open to more if it should develop that way.

He noticed that she had turned her seat toward him, and that her legs were slightly parted, giving him the slightest hints of the further delights she had hidden. Winking at her, Jack said, "Maybe we'll end up getting luckier than we had thought we would this evening."

Winking back at him while moistening her smiling lips with the tip of her tongue, Keisha responded, "This sounds like tonight could end up being a quite fun and entertaining evening." Hearing Jack's machine hit for a nice bonus while hers was going crazy as she hit for a $75 jackpot, she added that it looked like it could be a profitable evening as well.

At that point, Jack hit the bonus for fifteen free spins and Keisha reached over to take his hand to congratulate him on his good luck. She placed his hand just above her knee and opened her legs slightly more just as her machine hit a re-trigger, adding ten more free spins to her bonus. She squealed in delight, stood up and wrapped her arms around Jack's neck as she gave him a huge, passionate kiss, quickly slipping her tongue between his lips and withdrawing it before they attracted too much attention.

Keisha sat back down in her chair, taking Jack's hand and placing it back on her leg just above her knee. Still holding his hand in place, she began moving it up and down the lower part of her thigh where he noted that she wasn't wearing any kind of stockings under her skirt. Once he continued caressing her lower thigh on his own, Keisha then placed her hand on Jack's leg just above his knee and stroked it. A very quiet moan escaped from her as she looked around the casino to make sure that no one was watching them.

While they were playing, Jack and Keisha talked as they began to get to know one another, with each liking what they found about the other, including that their homes were only fifteen minutes apart. Jack let her know that he was divorced and that his 17 year old daughter lived with his ex. He learned that Keisha's husband had been killed in an industrial accident several years before and that she lived alone with her daughter who just turned 18 a few days ago.

Jack was shocked to hear that Keisha's daughter was 18 years old as she did not look like she could have a daughter that old. He looked her up and down and asked her, "What were you, ten years old when you had her?"

She laughed as she replied, "No, I was 22 when Tamiqua, who we call Tammy, was born. I met my husband when he was a junior and I was a sophomore in college and we got married after he graduated. My husband had a very good job as an engineer, so we were able to live a very comfortable lifestyle. I became pregnant a few months after we were married, graduated a semester early and Tammy was born the following April. For some reason, we were never able to have any more children, but the three of us were a very loving and devoted family.

"Tammy and I had always been very close, and we were devastated when Tony was killed. I don't know how I would have made it through if it weren't for Tammy, and the two of us have gotten even closer since then."

Jack moved his hand from her lower thigh and took her hand in his as he squatted next to her. He wrapped his other arm around her, feeling her arms as she put them around him, gently holding her as soft sobs escaped from her and dampening his shoulder. After a minute or two, he leaned over and kissed her forehead as her sobbing ended and she was able to once again gain control of her emotions. She lifted her chin so that she was looking in his eyes, saw the caring there that he had for her, as she kissed him on his lips.

"Thank you," she quietly said to him as they continued to hold one another. "It's been a long time since a man has held me like you just did and I didn't realize until now just how much I missed that."

Jack smiled at her as he replied, "I can only imagine what you and Tammy have been going through and I'm glad I was able to help you. You are a very huggable woman and it feels really good holding you in my arms like this." He chuckled as he continued, "I'm not so sure I want to let you go yet."

She giggled, leaned in and gave him another quick kiss as she replied, "That's okay. I don't think I want to let you go either."She paused for a moment, then said, "Unfortunately, they're going to kick us out of here if we don't let each other go, at least for now."

Jack sighed as he released her and moved back into his seat, still holding her hand in his. He pressed the button to roll the slots another time and was startled to hear that he hit another bonus. He laughed as he said, "Damn, woman! I think I'm going to have to keep you close to me! You're good luck!"

Keisha pressed the button on her machine and started laughing as she hit for a $20 payoff. "You seem to be bringing me good luck too!"

They continued talking and getting to know one another as they played the slot machines. They stayed where they were for another half hour before they decided to move to another area after each cashing out with several hundred dollars in winnings.

Altogether, Jack and Keisha had a very pleasant evening playing on the slot machines for a couple more hours, although neither of them did as well as they had on the first machines. Keisha looked at her watch and said, "I've got to get going soon so I can catch the bus. It only runs every hour at this time of the night and my daughter will start worrying about me if I get home too late."

"I can give you a ride. We don't live that far from one another, so it wouldn't be a problem. I've had such a good time here with you, that I really don't want the evening to end just yet."

Keisha smiled at him, gave him yet another quick kiss and replied, "I don't want this evening to end yet either. I'd appreciate it if you could give me a ride home. Will you come in and meet my daughter?"

Jack was a bit startled at that, and then his smile got even bigger than it had been. He winked at her and said, "Are you sure? I don't know how long I'm going to be able to resist you and I don't want to be accused of corrupting your innocent young daughter."

Keisha gave him a saucy look and answered, "I may not want you to resist me as it's been a long time since I've made love with a man." She smiled as she gave him a moment to contemplate what she had said. "Tammy may be inexperienced with men, but I'm not sure exactly how innocent she is. I do know that she is very curious about what goes on between men and women and I feel that she needs to learn." She paused for a moment before she said, "I need to go to the ladies' room before we go though."

"That's all right. I need to hit the men's room as well. Let's cash in our tickets first."

"Good. I'll meet you right outside of the rest rooms and then we can go." After they finished cashing in their tickets from the machines, the two of them walked toward the washrooms. Keisha gave Jack a quick kiss and then disappeared into the ladies' room while he went into the other side to relieve himself.

They met outside the rest rooms a few minutes later, then held hands as they walked to the parking lot to find Jack's car. Jack could have sworn that Keisha had been wearing a bra earlier, but the way her breasts moved as she walked indicated that she was now braless. Once they found it, Jack hit the key fob and unlocked it, walking to the passenger side to open the door for his lovely passenger. As he opened the door, Jack said, "Chivalry is not dead. It's only in critical condition."

Keisha laughed and rewarded Jack's chivalrous behavior by opening her legs as she got into the car. That caused the hem of her skirt to ride most of the way up her thighs, showing Jack that she was now going completely commando. She first looked at his eyes as she got into the car, pleased with where he was looking, then glanced lower, noting the size of the bulge that was developing there. Knowing the effect she was having on him, Keisha made sure that she took her time swinging her legs into the car. Once she was completely inside of the car, Jack closed the door and walked around the front of the car to the driver's side, adjusting himself as he walked.

Jack opened the driver's side door, got into the driver's seat, locked the doors after he had closed his, put the key in the ignition and started the car. He looked over at his passenger and noticed that she had not moved the hem of her short skirt any lower than it had been when she got into the car and that she was leaning somewhat toward him.

He turned to Keisha and leaned over to give her a quick kiss, but as soon as he moved toward her, she wrapped her arms around the back of his neck to hold him in place as their kiss rapidly grew in its intensity. He put his right arm around her back, drawing her closer to him as their kiss became even more passionate. Jack placed his left hand on her abdomen before sliding it up her body so that he could caress her breasts, feeling her rapidly hardening nipples under his fingertips.

After a few more minutes of dancing and dueling tongues, Keisha broke the kiss and emphatically said, "I need you inside of me! Let's go to my house. NOW!"

Jack wasn't about to argue with those sentiments, so he disengaged from their embrace and put on his seatbelt, made sure she had hers on, then backed out of the parking space and exited the parking lot. Once they were on the road, Keisha gave him the directions to her home, then took his right hand in hers and placed it on her thigh.

As they were driving toward Keisha's house, a thought popped into his head. "Shit!" he exclaimed. "I don't have any condoms with me. Is there anyplace along the way so that I can pick up some?"

Keisha looked at him and asked, "Are you clean and disease free? I haven't been with a man since my husband died and was tested when I had my last physical. Tammy is still a virgin so she is clean as well."

"I was tested last month and do not have any diseases. I have not been with anyone since then. What about birth control?"

"I put Tammy on the pill a couple of years ago, so we're okay there so you don't need to worry about that either." Keisha smiled at him and said, "Thank you for caring enough to ask about that. Just you asking me about birth control tells me that you are a good man." She giggled as she added, "Plus feeling you shooting your sperm into me is going to be SUCH a turn on for me!"

Keisha then took his hand and gently pushed it further up her thigh until his fingers were brushing her smooth, slick labia. Even with their windows down, Jack was able to detect the scent of her arousal as his fingers continued to explore the center of her soaked femininity. Jack slid two fingers inside of Keisha's sopping pussy and had just coated her erect clit with her juices when she told him to slow down and to then turn into her driveway. He pulled his fingers from her pussy, then drove into her driveway, parked the car under a large maple tree, turning off the lights before shutting off the car and releasing his seatbelt. As Keisha was about to get out of the car, Jack asked her to hold off for a moment as there was something he wanted to do first.

Helping to lift Keisha's left leg, Jack asked her to turn a bit more toward him. Once she was in position, he leaned over the padded console and gave her a quick kiss before leaning farther down so that his head was between her wide spread thighs. Jack began nibbling the back of her knee, feeling the goosebumps as they magically appeared on her thighs, and he suspected, other parts of her delectable body as well.

Normally Jack preferred to take his time in order to fully tease and arouse his partner, but he decided to forgo that this time. Jack knew that Keisha was already close to the edge, and he was anxious to drink her heavenly elixirs, so he quickly nibbled his way along her thigh until his face reached the Promised Land. Jack paused there for a moment, breathing in her heavenly aroma, then lowered his face and began to feast as if he was taking part in a pie eating contest. He used the flat part of his tongue to lap between her labia, rolling it back into his mouth from time to time so he could partake of her heavenly honey. He remembered the old saying, Be healthy, eat your honey as he turned his face from side to side, making sure that his mustache contacted her clit, pushing her arousal to ever increasing heights.

Jack had felt an amazing connection with this wonderful woman almost from the moment he met her, and that link seemed to be strengthening the more time they spent together. Through that connection, he could tell EXACTLY how close she was to climaxing. When she was within seconds of exploding, Jack did the unthinkable. He lifted his face from her pussy and said, "Let's go inside and do this right."

Keisha was so discomfited by Jack's refusal to let her climax that she was beside herself. She grabbed for him in an attempt to pull him back so he could finish taking her over the top, but he managed to avoid her, smiling at her frustration. She snarled at him, "Get back here! I was just about to cum when you stopped! You can't leave me like this!"

Jack knew that he was taking a chance of pissing her off so much that she would send him home without any nookie, but he felt fairly confident that she wouldn't do that. As it turned out, he was correct in his thinking. He reached for her hand and said, "Come on. Let's go inside. I would rather that our first time making love was somewhere other than in my car." He paused for a moment before adding, "Just think about how intense your orgasm will be when I finally do take you over the top because you are so close to the edge already."

Keisha grumbled a bit as she finally acceded to his desires and turned toward the passenger side car door. By that time, Jack had come over to her side and helped her out of his vehicle. After making sure that all of the windows were up, he used the key fob to lock the car doors and held Keisha's hand as they walked up the steps to the front porch of her home.

As Keisha and Jack approached the front door, they thought they heard something and halted. Keisha quietly walked across the unlit porch to an open window and was able to look through the window to see what was happening inside the house and what may have caused the sound they had heard. Keisha's bright teeth contrasted nicely against her coffee colored skin as a huge smile appeared on her face. She turned away from the window and toward Jack, motioning for him to come to her but that he should do so quietly. Jack silently approached the window and saw that the slight breeze was blowing the curtain open, enabling them to see what was happening inside the living room.

Jack stood behind Keisha, wrapping his arms around her and holding her back against his front as they peered through the window. Jack was astounded at what he saw and heard. He spied a young woman, who could only be Keisha's daughter Tammy, as she looked just like a younger version of her mother. Tammy was on a recliner, with it leaning completely back so that her legs were elevated. The recliner faced the window through which they were looking, providing Jack and Keisha with a bird's eye view of the younger woman.

What had astounded Jack was that although Tammy was wearing a silky light green robe which contrasted wonderfully with her dark skin, she had it untied and open. She had one hand pinching first one erect nipple then the other while caressing her swollen labia and clit with the other. While she was masturbating she said, "Oh Yes! That feels so good! Lick my virgin pussy as you prepare to make me a woman! I am so ready for this! I need you inside of me NOW!" With that, her entire body shuddered and quaked while a loud moan escaped from her lips as she obviously experienced an intense orgasm.

Keisha leaned over onto the window sill, causing the hem of her short skirt to rise so that it was just below what would be her panty line, if she had been wearing panties. She felt Jack's hands as they worked their way under her skirt, so she pushed her butt back against him, feeling his stiff erection as it rested between her butt cheeks. Not only had Jack totally aroused her, but watching her teenage daughter as she masturbated had Keisha at a fever pitch. Jack quickly discovered how excited Keisha was as his fingers walked up the insides of her wide spread thighs as he felt how drenched they were from Keisha's fluids.

Jack felt Keisha's hand reaching back to try to undo his belt. "Jack!" she hissed in an attempt at keeping her voice quiet. "I'm on fire here! I need you inside of me NOW!'

Jack continued to stimulate her clit and pussy with his one hand while he brought his other back to undo his belt and his pants. Thirty seconds later, he had managed to lower his pants and his silk boxers and had hold of the base of his petrified penis. He pushed the head of it between her wide spread thighs and slid it along her labia to ensure that it was totally lubricated, making sure that he bumped against her clit at least a half dozen times while he was doing so.

While Jack was lubricating his cock with Keisha's natural oils, he felt the fingers of one of her hands separating and holding open her lower lips while her other hand took hold of his manhood so she could aim it so that it would hit its target in one shot. When Jack felt that his penis had started to enter her heavenly portal, he was amazed at how tight her sheath felt, so he eased his way in to enable her to get used to his size. Slowly, inch by inch, he slid his sword into her slippery scabbard, further stimulating her senses as he stirred her steaming cauldron.

Once he was fully enveloped in her depths, Jack held in place, savoring the sensations he was feeling from this wonderful woman who had given herself to him. He leaned over Keisha's back and reached around to take her breasts in his hands, gently fondling them and rubbing her diamond like nipples between his thumb and index finger of each hand. He found that his face could reach her neck while they were in this position, so he began to lightly kiss, lick and nibble her neck and earlobes, feeling yet more goosebumps appearing on her back and hearing a low moan escaping from her.

Keisha pushed herself back even harder against Jack, indicating to him that she was acclimated to his size and that she was ready for him to begin moving in and out of her. As he slowly began moving back, he lifted his face from her neck and again looked through the window where he saw Tammy caressing her sexy teenage body, her whole body squirming as she pinched her nipples. He watched the young woman play with her nipples for a moment or two before she slid both of her hands down her body, using the fingers of one hand to hold her labia open while she stimulated her clitoris with the other.

Jack didn't think it was possible, but seeing the contrast between the bright red of her most intimate place and the dark skin surrounding it on this young teenage beauty aroused him even beyond the level where he had been. He listened as the young girl inside fantasized about having a man for the first time, moaning and shouting, "Yes! Yes! That's it! Fuck me! Fuck me and make me a woman!" He then heard Tammy screaming as fluids gushed from her vagina as her climax overwhelmed her teenage body.

Keisha moaned as she too watched Tammy reach the heights of Nirvana. She had never been as aroused as she now found herself as she watched her daughter cum while Jack's hard cock was sliding in and out of her. She began to thrust her hips faster and harder as she rapidly approached her point of no return. Jack however, was determined to take his time to keep from going off too soon and extend the pleasure they were each enjoying, so he moved his hands back to grasp Keisha's hips as she tried to get him to thrust faster.

She hissed, "Come on Jack! Faster! Harder! I'm almost there!"

Jack began thrusting slightly faster into Keisha's pussy, but not fast enough to satisfy her. He then took one hand from her hip and reached around to stimulate her clitoris as he maintained his slightly faster pace with his lunges into her body. That apparently did the trick as he felt her vagina squeezing and grasping his penis as she was overcome by her explosive orgasm.

Keisha then cried out, "Yes Jack! A little harder and faster! Oh God! That feels so good, baby! I'm cumming Jack! I'm cumming so hard!"

Keisha's pussy clamped down so hard that Jack was unable to move in or out of her while Keisha's body responded to all of the stimulation she had received that evening. He looked inside and saw Tammy putting down the lower part of the recliner, then standing and walking toward the open window while holding her robe closed before hearing her call out, "Mom? Mom? Is that you?"

Keisha had a number of aftershocks from her orgasm flowing through her body, so it took her a minute or two to respond to her daughter. "Yes. It's. Me." she managed to gasp in response to her daughter's questions.

"Why are you out on the porch and who is that with you?"

Jack was totally embarrassed at Tammy catching him and her mother making love on the porch. His erection almost immediately shrank and fell out of Keisha's vagina. He didn't want to bring attention to the fact that his pants were down, so he wrapped his arms around Keisha's waist and stood up, pulling her with him so that his genital region was still blocked from Tammy's line of sight.

By this time, Keisha had recovered sufficiently to be able to answer her daughter's questions. "This is Jack. He and I met at the casino this evening and we seemed to bring each other good luck. We ended up sitting and playing the slots together all evening, with each of us winning a couple hundred dollars. We got to talking and found that we seemed to hit it off with each other. Neither of us wanted the evening to end, so he offered to give me a ride home as he doesn't live far from here.

"Now, as far as why we're still on the porch rather than inside the house, we came up onto the porch and as I was getting ready to put the key in the door lock, I heard what sounded like a moan." Tammy's mocha colored skin darkened as she blushed since she knew that she had been moaning quite loudly while she had been masturbating. Keisha then continued, "I noticed that the window was open, so I came over here to see what was causing the noise we heard. When I saw you on the recliner, I motioned him to come over. He and I had been flirting and teasing each other all night and we were both REALLY worked up by that time. When we saw you on the recliner, we couldn't hold off any longer, so I leaned over onto the window sill and pulled up the back of my skirt while Jack undid his pants. He teased me some more by taking forever to get his hard cock into me, but once he did, the feelings were divine!"

Keisha paused for a moment and smile as she recalled the sensations she had experienced. "We tried to be as quiet as possible, but I lost control when I climaxed and was louder than I thought I was. Jack made sure that he saw to my pleasure, but he hasn't cum yet and I'm sure that he is feeling a bit frustrated." She paused for a moment, turned her head and looked in Jack's eyes, smiled and said, "The last thing I want is for Jack to feel frustrated! He and I seem to hit it off right from the start and I for one want to get to know him much better to see what might develop."

Jack leaned forward a little bit and gave Keisha a light kiss on her lips before replying, "I want to get to know you better as I see that there's the possibility that we could be very happy together." He looked at Tammy, who by this time was not holding her robe as tightly closed as she had when she first walked to the window. "I also realize how close you and Tammy are and how important you each are to the other, so I would like to get to know you as well, Tammy."

Keisha then said, "We should get inside rather than talking through this window. Tammy, could you unlock the door for us, please?"

Tammy replied, "Sure, mom," then walked away from the window to unlock the front door. While she was doing that, Jack pulled up his pants and fastened them and Keisha pulled down her skirt. Once they had themselves situated, Keisha took Jack's hand in hers and the two lovers walked to the front door and entered the house.

After they had gotten inside, Keisha closed and locked the door, then turned toward her daughter. Tammy released the robe she had been holding closed and moved to her mother, greeting her with a hug and a short yet passionate kiss to her lips. She then moved her lips to her mother's ear, quickly flicked her tongue into her ear before she whispered, "Welcome home, Mom. I'm so glad you're here. I am so horny right now, I can't stand it! I called Debbie to see if she could come over, but she had some things she had to do and wasn't able to. Are you going to introduce me to your friend?"

Keisha removed one of her arms from around her daughter's waist while holding her close with the other and motioned to Jack with her free arm. Jack moved over toward the two women and Keisha put her free arm around his waist. This drew him closer to them while Tammy released her arms from around her mother and turned so that she was facing him. The younger woman made no secret that she was checking him out as she stood there with her robe loosely closed, yet open enough to hint at what was beneath it. Tammy smiled when she saw that Jack was checking her out as well, and how her semi-open robe was affecting the man.

Keisha had one arm around Jack and one around Tammy as she smiled and said, "Jack, I'd like to introduce you to my daughter Tammy. Tammy, this is my friend Jack, who I hope we will both get to know much better."

 
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