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Madison And Jack

"Love develops between a young lady and an older man"

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6.0k Views 6.0k
3.5k words 3.5k words

Author's Notes

"The characters in this story are fictitious. Any similarity between them and a real couple is purely coincidental. <p> [ADVERT] </p>All characters are at least 16 years old."

Having graduated from college, I started my own business in commercial design and construction utilizing the skills I had learned while working in the construction industry and my studies in architecture and engineering while in college. Seven years along, I was doing very well in business but working long hours. I had been in a few rather serious relationships but eventually, the females I was involved with realized they came second to my career.

At age twenty-eight, my mother, who was now living a great distance from me, kept telling me that it was time to start stabilizing my life. I decided that owning a home instead of renting an apartment might be a great way to start. I found a very large, great home in a great area. Every home in the area sat on ten acres and each home was as private as private could be.

After moving in, I realized that lawn care and landscaping maintenance was more than I could possibly handle on my own. Not knowing who might be a reputable source in the area and not knowing any of my neighbors, I decided to have a little cocktail and cookout gathering at my place. I hand-delivered twenty invitations to my neighbors' mailboxes and asked for an RSVP. Surprisingly, I received sixteen positive responses.

At my little gathering I not only got to meet my neighbors and get some property maintenance recommendations but got to meet Larry and Lisa. As we talked, they told me that they had a sixteen-year-old daughter, Madison, who could probably do just about anything that I might need, and also it would be a good learning experience for her to be responsible and to see what a job commitment would entail.

I met Madison a few days later. She was a very pleasant sixteen-year-old who seemed a lot more mature than her chronological age. We agreed on what she would do and on what her pay would be. Her parents were more than satisfied with what I was willing to pay and also what their daughter would be doing.

For the next three years, Madison became somewhat of a fixture at my home. I often would be gone three, four and sometimes five days out of the week. We had reached a point that she would often have a dinner meal prepared for me when I arrived at home since she knew my schedule. It was rare when I actually would see her in person but we often talked, texted and left actual handwritten notes for each other. She was very trustworthy, and in my opinion, a great person and employee. From the onset, I had given her pool privileges if she would like to take a swim or use the whirlpool. I really didn’t know if and when she took advantage of it unless she would mention it to me. As those three years passed, I watched her begin to develop into quite a beautiful-looking young lady.

Madison graduated and decided to enroll in the local college. Surprisingly she told me she could still continue doing what she had been doing for me around the yard and house. Another year went by and she had now completed her first year of college and had made the Dean’s list for both semesters. We decided we should celebrate completing her first year. Plans were made for her to prepare an Italian dinner at my house, and her parents would attend as well. It was a Friday and I would not be getting back home from out of town until about four o’clock.

When I walked into the door, the aroma of Italian cooking filled the air. I had picked up a couple of bottles of fine Italian wine to go along with dinner and our little celebration. There were no cars in my drive and I wondered if anyone was even in the house.

"Madison?" I called out.

"Hi, Jack," her voice answered.

"I wasn’t sure if you were here or not. I didn’t see any cars in the drive."

"Oh, my parents dropped me off."

"They’re coming, aren’t they?"

"Well, no…there’s been a change in plans. My mother got a call earlier that her mother had fallen and broke her hip. She was going to have to have surgery and so my mom and dad were able to book a flight and they left to go to her."

"Oh! Well, what about our dinner? It was OK with them for just the two of us to dine together like this?"

"Oh yeah, they didn’t seem concerned about it at all."

"Perhaps I should call them."

Madison looked at the clock.

"You can probably reach them now. Their plane should have landed forty-five minutes ago."

I quickly grabbed my phone and called her father. I expressed my concern for his mother-in-law and hoped all would go well. He said he was sure everything would go okay and that he had no problem with me having dinner with Madison. All he asked was that I would drive her home when we were through, and I told him that would be no problem.

"Everything OK, Jack?" Madison asked.

"Yes, everything is fine. Just like you said."

"Good."  Madison smiled.

Looking at Madison, she was wearing a rather strange garment. I’m not sure what one would call it: a dress, a smock, maybe an apron. It actually looked like someone had taken a red and white checkered tablecloth and created something to wear. I didn’t say anything to Madison about it. I told her I was going to put my things away, wash up a bit and then be back to give her a hand with anything she needed in the kitchen.

Upon returning to the kitchen she told me to have a seat, as everything was about ready. She had taken the two bottles of wine that I had purchased out of the packaging and had set them on the counter.

"Which one shall we open first, Jack?"

"Do you think that you should be drinking wine?"

She smiled. "Of course, why not?  It’s just dinner. Not some drunken college drinking party."

"Well, OK. Let me do it."  And with that, I opened one of the bottles.

I took a seat at one end of the table and watched Madison. She obviously knew her way around the kitchen but I still couldn’t figure out what she was wearing. She must have noticed me staring at her.

"What’s the matter? Don’t you like my dinner attire?" she said with a big grin.

"Well…I’m just trying to figure it out."

"I think it belonged to my great grandmother or someone. It’s a very old kitchen apron. It does cover everything up quite well, don’t you think?"

"I can’t argue with that."

With that, she said that everything was done. She undid the tie that was holding the apron together and removed it. As she took it off, my eyes couldn’t believe what I was seeing. There she was, no longer the young sixteen-year-old girl that I had met four years ago, but she was now Madison, the young lady. She was wearing a short khaki skirt that came half-way down her thighs and a white button-down blouse that was somewhat sheer as I could easily see that she was wearing a purple, plunging, push-up bra.

Suddenly I was looking at Madison in a much different way. I was noticing things about her that I had never really paid attention to before. Madison was a tall girl, standing about five-foot-ten-inches tall and had very shapely legs. Breast-wise, she seemed to be taking after her mother, who had very nice breasts. I did notice that she had left perhaps one too many buttons unfastened on her blouse as she was revealing a considerable amount of cleavage.

I could not take my eyes off her as she set all the food she prepared on the table. The food all looked good and tasted great. We sat and ate and drank wine and talked for about an hour before we had finished our meal. I helped clear the table, put the food away and get the dishes into the dishwasher.

"Wow, Madison, that meal was really terrific. A lot more than I had expected."

"Well, I’m glad you liked it."

There was still some wine in the bottle so we decided to fill our glasses and go into the media room to watch some tv. I gave the controller to Madison and told her to put on whatever she wanted to. I sat down on the two-seat couch, and somewhat surprising to me, she decided to sit right next to me.

The movie she chose was a romantic thriller. I was a bit uneasy when they got to the nude and lovemaking scenes. I noticed that Madison moved around slightly as well, repositioning her body. As the movie ended, we had finished our wine. Madison was seated to my left. We looked at each other and then she caught me totally by surprise as she slung her left leg over my lap, faced me, put her arms around my neck and planted one of the most passionate kisses I have ever had on my lips.

She was straddling my lap as she faced me. I felt her tongue enter my mouth. I was completely overcome by her affection to me. Here I was, a thirty-two-year-old man French kissing a nineteen-year-old and feeling her lower torso rock against my lower body. Was it the wine? Was it the lovemaking scenes in the movie? Or was it that I actually had feelings for this young woman that had been buried deeply in my subconscious?

Madison suddenly broke our kissing. She pushed back a bit and unbuttoned and removed her blouse. She acted quickly to unbutton and push back my shirt so as to leave me bare-chested as she pushed her bra-covered breasts against me and then kissed me again. I was at a total loss to say anything or to try to stop her sudden and unexpected advances on me. I could actually feel the heat coming from her pubic area as she rocked against me.

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"Jack…I love you."

"Oh, Madison... Madison... you're only nineteen and I’m thirty-two, how can..."  And then I was silenced as she shoved her tongue back into my mouth, not allowing me to finish my sentence. She obviously was on a mission and as I look back, it was a very well-planned mission.

She quickly got off me and stood before me. She bent down slightly and began to unbuckle and undo my pants.

"No, no, no, Madison. Not here. Not here. Do you want to go into the bedroom?"

She nodded her head and then extended her hand as if to help me get up off the couch. I got up and we walked to my bedroom. We entered the room and I removed my shirt and watched as she removed her skirt. She was wearing a pair of purple bikini panties that matched her bra. She dropped to her knees in front of me and undid my pants. She removed them and my boxers in one quick movement. I stepped out of them and then watched as she removed her bra. Her breasts were beautiful, her nipples erect and hard like two bullets. She then slid her panties down, revealing a full bush of rather thin, light brown pubic hairs.

"Sit on the edge of the bed, Jack."

I felt unable to resist her command. I sat on the edge of the bed. I opened my legs and she knelt down between them. She gently grabbed my cock and lifted it slightly. I was at a full-blown erection and throbbing. She brought her lips to the tip of my mushroom and gently kissed it. Her tongue then extended from her mouth and she swirled it around my swollen mushroom head a few times. She opened her mouth and then took my entire length. I felt my cock hit the back of her throat. She put her left arm around me and grabbed the right cheek of my ass as if to hold me in place. Her right hand began to fondle and play with my balls. Her head began to bob back and forth as she fucked my cock with her mouth.

I was already beginning to feel that familiar tingle starting to build inside me, signaling that my cock was getting ready to explode. It was just then that she stopped. She pulled my cock out of her mouth, gently grabbed the head with the fingertips of her left hand that she had removed from my ass and pushed my cock slightly upward and against my body. She then began to lick the underside of my shaft from top to bottom as she continued to play with my balls. She then took turns licking and sucking each of my nuts.

At this time I was straining to hold back from exploding. With her right hand firmly grasping both of my balls, she took me back into her mouth and began to bob her head.

"I’m going to cum. I’m going to cum…" And with that, I exploded inside her mouth, shooting somewhere between five and seven healthy strands of thick, white, hot cum inside her mouth. It was a huge load and I expected to see some of it leak out of her mouth and down her chin but not a drop came out. Looking at her mouth, I could tell that she had swallowed my offering.

"WOW, you really had a lot!"  She smiled as our eyes locked on each other.

"Yeah, I guess I did."

She stood up. Pressed her body against me and once again kissed me. She shoved her tongue into my mouth and for the first time I was tasting my own cum. We kissed for a bit and then she broke the kiss, pushed her head away from me and said, “Make love to me, Jack. Make love to me. I want you to fuck me.”

"Madison, no, no...it’s not right. This has gone too far already. We shouldn’t have...I shouldn’t have let this happen."

"But, Jack, I love you. I want you. I want to live the rest of my life with you."

"Madison, I’m much too old for you. You need to love someone more your age."

At that point, she took my hand and pushed it onto her pussy, which was sopping wet.

"Do you feel that, Jack? Do you? I want you. I need you. I don’t want anyone else but you. Do you love me? Do you...Jack? I want you to fuck me. I need you to fuck me. Are you going to make me beg for it?"

At that point, I realized that I really did want her. That maybe I actually did love her. She had been so good to me over the years and always did things to make me happy, and now she was asking me to do something for her. Asking me to make love to her. Asking me to fuck her. I realized that I could not refuse.

Without saying another word, I stood up and scooped her up in my arms like a bridegroom lifting his bride to carry her over the threshold on their wedding night. I laid her on the bed. I stood back for just a few seconds to admire her gorgeous, sexy, young body. She spread her legs open. I got onto the bed and knelt between her legs. I put my head down between her legs and began to make love to her pussy with my tongue.

Her moans signaled her enjoyment. After a few minutes, I looked up to see her playing with her tits. Her body began to shake slightly. Then her hips began to buck up and down as her moans became louder. My tongue was flicking her clit while my finger fucked her pussy.

"Oh fuck, Jack. Oh fuck. I’m gonna cum. I’m gonna cum. Oh fuck. Don’t stop."

And then her body went into a full-blown orgasm as she wildly tossed about. Her thighs locked onto my head. I felt like my head was in a vise as she squeezed it. Her loud moans of ecstasy soon subsided and her thighs loosened their grip on my head. She became still for a moment and then called out to me.

"Fuck me, Jack. Fuck me now. Give me that beautiful, big cock of yours."

I used my hand to wipe her sex juice from my face and then grabbed my cock. I guided my swollen mushroom to her opening, and as I began to slowly push it in, Madison blurted out, "Go slow, Jack. Please go slow. I've never done this before."

I quickly pulled back and knelt straight up and looked at her.

"Are you a virgin?"

She nodded her head. "Yes, I am. I’ve dated but I’ve never gone all the way. The reason was that I had made up my mind quite some time ago that I was going to wait for you."

I have to admit that I was stunned but I also knew that we had reached a point of no return. I once again pushed my mushroom into her opening and began to enter her.

"It’s going to hurt a bit when your hymen is broken."

"I know, Jack. I’m ready.  Give it to me.  Give me your beautiful cock.  Take my virginity.  Make me a woman."

I pushed forward and felt some resistance. I knew my cock was about to tear her hymen open and transform this beautiful young lady into a woman. I pushed in, tearing her hymen open. Madison squeezed her eyes shut and clenched her teeth as I’m sure the pain was a bit more than maybe she suspected. I saw some tears form at the corner of her eyes as my cock went all the way into her. I held my position and told her I would not move until she was ready.

My cock remained still inside her for a couple of minutes, and then I saw her breathe a couple of deep breaths.

"It’s OK now, Jack. It’s OK. You can move now.  Fuck me. Fuck me good."

With having received the go-ahead, I began to fuck her. Slow at first and then I picked up intensity. As I pounded her I watched her beautiful tits bounce back and forth with the same rhythm of my pounding.

"Oh fuck, Jack, this is good. Don’t ever stop. Fuck me. Fuck me. Give me all you got."

With that, I fucked her hard and fast. She began to orgasm again and as she did, I felt that familiar tingle in my balls and cock. I knew I was about to cum. Not wearing a condom, I knew I had to pull out but damn, I didn’t want to. I kept fucking her until the very last second. I barely had my cock out of her when I began to shoot. I quickly grabbed my cock and jerked it. I think I counted six long, thick ropes shooting out of me. One went as far as her tits while the others landed on her stomach and pubic area.

Once we both regained our senses, she asked why I pulled out. I simply told her that since I had not used a condom, I didn’t want her to get pregnant. To my surprise, she told me that she was hoping that I would get her pregnant.

Madison and I lay in bed for a while. She was lying on her side and I was on my side behind her. My arm was around her warm young body. It was hard for me to believe that I had just taken her virginity. My hand wandered over the front of her body. I grasped and played with her breasts. As my cock rested against the sweet cheeks of her ass, she occasionally would wiggle just a bit as if to tease me. I suggested that we get cleaned up as her pussy and my cock had some traces of blood on them from her hymen having been ripped open.

Madison opted to take a bubble bath while I showered. I changed the sheets while she was still in the tub. When she got out of the tub, the scent of her body was intoxicating. Both of us were back in the bedroom, nude. We looked at each other. It became obvious that she was going to spend the night.

 

 

Thanks for reading my story.  If you would like to hear more about Madison and Jack, leave a comment.  Please don't forget to vote.

 

 

Published 
Written by Carlo42
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