tagMatureNaughty Teen & Fiances Grandfather

Naughty Teen & Fiances Grandfather


Please read my "Naughty High Class Mom" pt.1 & pt.2 and "Hot Girl Leaves The Trailer Park" series.


My name is Allison. I am from Southern Mississippi. I just turned 18 a month ago. People are always stunned to learn that I am 18 because I look like I could pass for a much younger teen. My body is almost boyish in build. I stand 5'7" tall and am extremely skinny. I only weigh 90 pound! I have a very flat chest with the tiniest pair of brown nipples that are smaller than miniature erasers. My nipples barely extend from my flat chest. My legs are long and skinny and my ass is small, but has a nice round curve to it. It is my only feature that gives people the impression that I am a girl. The other thing that gives me the appearance of looking so young is that I have freckles all over my body and my skin is pure milk white; almost pale. To add even more of a visual to my young girl look I wear braces too. I have long blond hair that I usually wear in pigtails. My measurements are 29AA -21-32. Yes I am very skinny, almost boney. In fact you can easily make out my ribs when I am standing nude in front of a mirror!

I am very active in my local community church and a few months ago I met a very sweet guy who is also active in the church. His name is Chase. He just graduated from law school and is 6 years older than me. He is very caring and generous and is always going out of his way to help people in any way he can. He is also very religious and has a very good moral and ethical nature. In the short time of being together Chase and I became engaged and planned on getting married in just a month. We realized that we were so in love and that our values were so much alike that we knew that it was the perfect thing to do.

After graduating law school Chase was offered a position to work for his grandfathers' prestigious law firm in Miami. Chase had told me that his grandfather was a very powerful man who built an empire by being ruthless in business; in fact he had a notorious reputation for getting everything and anything he wanted, at all cost. This was a man who was the exact opposite of my fiancé.

When Chase had showed me pictures of his grandfather I was surprised to learn that he was 76 years of age. He stood 6 feet tall and had a fantastic physique. I new he was in great shape because in one of the pictures he was standing in a bathing suit on the deck of a huge yacht holding a glass of Champaign . I learned that the yacht was his and that it was his 76th birthday party. Chases grandfather was very distinguished looking with salt and pepper hair and had an amazing build. He had a lean slim body. His stomach was like a chiseled rock and he didn't have an ounce of fat on him. Like his grandfather Chase is also 6 feet but is not in great shape. He never exercises and is slightly overweight.

In one of the pictures I noticed 2 young girls that looked to be about 20 years old who were standing on either side of my fiancés very handsome and distinguished grandfather. The girls were wearing almost nothing! They were dressed in the skimpiest bikinis I have ever seen. The only things covering up their breast were the tiny straps that crisscrossed over the nipples and the thong part of the bikini did absolutely nothing to cover their bottoms! In fact the thongs drew attention to their asses and actually made them look even more nude! Not only were they wearing the most sinful bikinis but they accented their sinful appearance by wearing high heels. This devilish look gave them an even more lewd appearance. One of the girls was wearing a pair of black high heel pumps with open toes and the other was wearing a sinful pair of glass- like platform high heels.

As I looked at the pictures with curiosity about this older man in the picture I began to think of how different my fiancé was to him. I then saw another picture where he was actually kissing both of the young girls. It was then that Chase told me that his grandfather was always in the company of young women. While my fiancé was remarking on how vulgar and trashy they looked and that he loathed his grandfathers lifestyle, something began to stir in me and I began to think to myself,

'God I can't believe that my fiancés grandfather is 76 years old! Just look at his perfectly toned body. He's in better shape than any guy I've ever met including his grandson! Wow he is so sexy too! It's no wonder that young girls are swarming all over him. With his distinguished looks and ruthless reputation and wealth it's no wonder that he gets so much attention. I'm sure my fiancés grandfather can have his pick of any girl he wants!'!

At that moment I almost felt ashamed at myself because I suddenly began to have a wicked thought of being dressed in a similar bikini and wearing a pair of sexy high heels and kissing him too!

During the week Chase informed me that we were going to meet his grandfather. As part of him coming into his grandfathers' law firm he was buying us a house in South Beach. This was going to be part of our wedding present form him. He also said that his grandfather wanted him to be present for a big business acquisition that he was finalizing to learn more about the business he was going to be doing once he joined the firm. I wanted to make a good first impression on my fiancés powerful grandfather so I dressed in a conservative flowerily sundress with a pair of flat shoes. We flew to Miami in his grandfathers' private jet. This was another sign of the vast wealth he had.

When we arrived in Miami, Chase's grandfather met us in one of his private limousines. I was instantly taken aback when he greeted us. The pictures of him did not do him justice. He was extremely handsome and dressed in a tight fitting white shirt with expensive tailored black dress pants. His presence was so magnetic. Anyone meeting him could instantly tell that this was a man who exuded confidence and commanded power and authority. I then noticed that had the most penetrating dark gray eyes. Before he shook my fiancés hand I could feel his grandfather's eyes scan my boyish body. It was as if he was stripping me with his eyes! Suddenly the images of the young girls dressed in those bikinis and high heels flashed before me and I got somewhat turned on myself. The strange thing was that by the brief sly grin he gave me I could feel that he was thinking about my body.

As he greeted his grandson and fiancé he began thinking to himself, "So this is my grandsons' fiancé. I can't believe she's 18! She looks so young! I must admit I like her young innocent look, especially her pale milk white skin and all of those lovely freckles. So skinny! And look at those amazing tiny tits on that perfectly flat chest! WONDERFUL…Just SPECTACULAR! And braces too! MAGNIFICANT! Oh yes…this one is really turning me on. I'm going to thoroughly enjoy introducing her to my 13 inch cock, which I'm quite sure is huge compared to my pathetic grandsons!'

In the limo my fiancés grandfather was so charismatic and charming. He was saying how pleased he was to have his grandson joining his law firm. He added that it was his dream to pass the baton of the firm over to my fiancé in the near future. As we were riding he gave my fiancé a file to read about the deal he was finalizing. While my fiancé was eagerly trying to impress his powerful grandfather by diving into the document he was asking me questions about myself. During our conversation I could feel those penetrating eyes piercing the fabric of my conservative sun dress. When I crossed my long thin legs his eyes lingered on them then he looked up at me again and gave me an approving smile. God I couldn't believe it but I was actually enjoying the fact that my fiancés grandfather was staring at my body so openly and with lust. I was getting turned on and began to think,

'God I can't believe how sexy my fiancés grandfather is. I can't believe that he is really 76 years old! He's got me so turned on just by the way he's looking at me. God I wish I was alone with him in the limo instead of with my fiancé.'

Just then I grinned at my fiancés grandfather devilishly and secretly wished I was dressed in one of those sexy bikinis and high heels and really getting acquainted with him and making a very, very naughty first impression'.

As we drove along South Beach I was so amazed by the enormous and expensive homes. We arrived at a large gate that opened to a driveway that went for about a quarter mile. It lead to my fiancés grandfathers' house. It was the most spectacular home I had ever seen. To me it was a mansion. It overlooked the ocean and had 14 bedrooms, two swimming pools, complete gym and a full wait staff. His grandfather had the limo driver bring us to one of the three guest condos that were on the propriety. It was clear that my fiancés grandfather was an incredibly wealthy man.

I began to think, 'To all this wealth one would have to have a take no prisoner's personality.'

His grandfather told us to enjoy ourselves and that the wait staff was assigned to us for anything we would like or need. He had business to attend to for a few hours and invited my fiancé and I to a private club he was attending later that evening.

I had no idea what the attire would be and what to expect at the club so I dressed in a similar way that I had earlier; a sun dress with flat shoes. The club was a very exclusive member's only club. It was in a very exclusive part of South Beach. Just to drive on the road leading to the club you had to go through a private security company that manned a huge gate. The club was established exclusively for the wealthiest men in the world. As we drove in two attendants immediately rushed to the limo and opened the door for us. My fiancées grandfather didn't even acknowledge them and just walked towards the entrance of the club. As I looked back I saw the parking lot filled with the most expensive cars in the world.

The next thing that happened was so shocking. As we were walking into the club an older black man walked out. He looked to be a man in his sixties. He was stylishly dressed in an expensive tailored business suit. The shocking thing was that he walked out with a young blond teenage girl who was dressed like one of the girls I had seen in the picture with my fiancés grandfather. She was dressed in the most sinful bikini and high heels! The two were arm in arm and as the attendant went for his Mercedes they turned to each other and they began kissing in a very sexy way. Both their tongues were out and just the tips were making contact with each other. This lasted for a few seconds and as we approached the older black man broke off the kiss because he recognized my fiancés grandfather. He immediately put out his hand and said hello. As Frank introduced him to my fiancé and me I could see the blond looking at me as if to say,

'What's with the little girl look.'

When Frank introduced my fiancé and me to the older black man I nearly died when he said that he was a Senator from a mid-western state. The man was very polite and said to my fiancé that his grandfather has always been very generous with campaign contributions. As the older black Senator went on about my fiancés grandfather being very generous I noticed the young blond making eye contact with him and smile seductively. I also noticed my fiancés grandfather taking in the sight of her body without any regard for the black Senator. It was so obvious that she would have preferred to be with my fiancés grandfather. Even though he was older then the black Senator, he looked a lot younger then him, and was in a lot better physical shape too.

When we went into the club I could not believe the different types of people that were there. There were many Middle-Eastern men and some were dressed in the cloths of Arab sheiks with the scarf head pieces. There were a lot of European men dressed like my fiancés grandfather in fine tailored suits. The men in the club were all older, in there late fifties to mid- seventies but the girls all seemed to be in there late teens and early twenties.

All of the girls were dressed in the most sinful cloths. Some were dressed like the blond who left with the black senator, in the most daring string bikinis and high heels while others wore short mini skirts with sheer white blouses and lacey bras with exposed thigh high stockings and high heel pumps. Some were dressed in ultra transparent dresses that clung to their bodies like a second skin. The obvious sign that they were not wearing a bra was when their breast were very visible and their nipples stuck out advertising the fact that they were there to be noticed and probably to leave with a very wealthy older gentleman. A few girls were even dressed like naughty school girls, wearing plaid skirts with white ankle socks and white high heel pumps with a transparent white blouse and sheer lace white or black bra.

I had to admit I felt very self conscious about being so out of place in this wealthy up-scale club. Here I was dressed so conservatively in comparison to all of the other girls my age in the club. I was wearing a long, loose fitting dress with a floral pattern that tied in the middle and had a collar that went up to my neck. I also was wearing a flat pair of white shoes which was very conservative in comparison to all the girls wearing high heels pumps or those glass platform high heels. A few of the girls were naughtily dressed in a pair of ultra-short shorts that lewdly exposed the bottoms of their ass cheeks. The high heels only added to their wanton look. My innocent look combined with my freckles, my 90 lb body and braces and an extremely flat chest must have made me look like a 12 year old girl instead of a recently turned 18 year old.

As my fiancés grandfather mingled throughout the room talking to various distinguished men I could see every girl checking him out as if to say,

'I wonder who is this sexy older man is. Wow is he hot or what?'

I even saw a few come over to him and give him a kiss and whisper something in his ear. It was so obvious what they were suggesting. My fiancés grandfather commanded attention. He exuded power and wealth beyond anyone in the room, and the room was made up of some of the most powerful and wealthy men in the world too. He was also the most distinguished looking man in the room. At 76 years of age he looked so much younger then most of the men in there late fifties. I had to admit I was getting a little jealous of all the attention he was getting from all of the girls. I couldn't show it because I was with my fiancé. My fiancé also could not get over the atmosphere in the club and the obvious exobishionist ways of the girls my age. My fiancé is a very faithful Church going practicing Christian, and to him this was appalling and disgusting aberrant behavior. As for me, a big part of me wished I was dressed like one of these girls and on the arm of my fiancés wealthy powerful grandfather.

The next day came and I was invited to come to the final meeting to observe the transaction with my fiancé. I learned that my fiancés grandfather was working on a very big deal to buy out an international company. His grandfather had negotiated a deal to buy the overseas company for twenty million dollars. The agreement was that all of the ten thousand employees would keep their positions in the company and that they would share profits in the growth of the company too. During the meeting to negotiate the sale transaction I was so impressed at my fiancés grandfather. The way he commanded authority was so impressive. At times the meeting turned negative regarding his intentions to for the company. Some of the upper management people were suspicious about his intentions. Chases grandfather assured everyone that the contract detailed all of the facts regarding the preservation of the company. What everyone in the room including my fiancé, and all of the twenty attorneys didn't know was that there was a clause in fine print that stated that the company could be sold immediately after the sale.

Once the documents were signed my fiancés grandfather picked up the phone and a security team came into the room armed with guns. With the shock on everyone's faces including mine and my fiancés his grandfather arrogantly announced that his signature was a legal proxy for an Arab company in the Middle East and that effective immediately the company was sold and that all employees were terminated. The room suddenly turned into a riotous atmosphere as everyone began screaming and shouting obscenities directed at my fiancés grandfather. As fast as the room went into an uproar the guards drew their weapons and circled my fiancé and I and all of his grandfathers attorneys and his grandfather. The sight was almost surreal. I will never forget the sadistic grin and smile that came over my fiancés grandfather face at the sight of grown adults crying, especially all of these powerful men in the room.

When we were escorted out by the security team my fiancés grandfather handed one of the men a case which I learned contained $250,000 for their work. When we entered the limo my fiancé had the look of shock written all over his face and I myself was still shaken by what had just transpired. The only one that appeared to be enjoying himself was my fiancés grandfather. In fact he was actually reveling in what took place in the board room! He then pooped a bottle of very expensive champaign and suggested that we toast the fact that he just made over 200 million dollars on the sale of a company that didn't cost him a dime.

When we each took our glass, my fiancé brought up his concern for all of the people that were going to loose their jobs and life savings. At that comment his grandfather just laughed and said menacingly,

"I could care less about their families or their losses. My only concern is the profit I make…The bottom line!"

He then looked at me then at my fiancé and said unsympathetically, "If you plan on building an empire and a future for yourself and your very lovely fiancé, then you better grow a thick skin and learn how to become ruthless very fast son. Very fast!"

I don't know what came over me, but at that exact moment I began to get very turned on by my fiancés powerful 76 year old grandfather. The two could not be more different. The idea that this man was so ruthless and cold-blooded with no regard for the fate of so many innocent people who worked their entire lives to build homes and families and that gave their all to a company that was just swept out from under them, and that their entire lives were instantly shattered and the fact that he was reveling in his success and their fate caused my tiny nipples to become instantly erect and sent shock waves way up into my tight 18 year old pussy. At that very instant Chase's grandfather and I made eye contact and it was as if he could read my very naughty thoughts. He grinned at me knowingly as I returned a sly grin at him for a few devilish seconds as my fiancé looked out the window in dismay at what his ruthless grandfather had just done to the lives of so many innocent families.

He then made a cell call and after disconnecting the call he said that he was sending Chase with one of his associates to the Middle East to deliver the signed documents of the take over. The trip would take two weeks to complete the legal transaction. He told my fiancé that I could stay behind to look at various real-estate for our relocation. When his grandfather dropped us off at the condo he informed Chase that his private jet was leaving in the hour. There wasn't much time for us to pack. I rode with Chase to the airport and gave him a big kiss goodbye and wished him good luck and told him that I would miss him.

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