Sinful Degrees of Separation Pt. 08

In this chapter Hailey's seventy year old father is a magnet for sexy teens.

NERDY TEEN: SCHOOL BOOKWORM

Kate was the girl who told, Clare the story of her friends Crystal and Heather fucking her father. If anyone had told Hailey or her cheerleader friends that Kate had fucked her father they all would have thought it was a joke and would have laughed in total disbelief.

Although Kate was in the inner circle of friends with Hailey, Crystal, Heather and Clare she was what everyone in school thought of as a 'nerd.' She was a horror student with the highest of I.Q's and a total book worm. The girls on the cheerleading squad took Kate into their inner circle because she was very helpful in doing last minute homework assignments or term papers when one of the girls was out on a date. To make her feel like she was part of the team they voted her the cheerleading squad's manager.

Kate was the girl in class who was very shy, and had a very meek, timid voice. Except for the cheerleading squad she was very anti-social and was considered the school geek. She always came to class dressed conservatively in long ankle length skirts, flat shoes and loose fitting blouses or sweaters. Her hair was always done in pigtails, and her glasses were as wide around as saucers.

She wore braces and had freckles that covered her body. With the flattest of chest measuring 29A-21-31 she had the body of a thirteen year old boy. She stood five feet six inches tall and was rail-thin, weighing seventy five pounds with all of her cloths on and dripping wet.

Like Hailey's entire group of friend's, Kate had always thought her father was very handsome and in the privacy of her bedroom imagined doing the naughtiest things with him sexually. Along with being typecast as the quintessential bookworm, Kate was an avid reader of romance novels and found great fantasy in reading more graphic stories found on the Literotica website.

Her favorite writer on Literotica was Shoguy. The writers stories about confident young teens fucking much older men of power, stature and wealth were the ones she loved reading about. As she read these intense and lifelike stories she imagined herself as the young teen in the story fucking the enormous cock of the older man in the story.

Reading stories about confident, well-endowed older men fucking teenage girls was what turned her on the most. As she read these stories her mind always drifted to her good friend, Hailey's father as she imagined them passionately kissing then fucking all night, just like the older men in the stories she read on Literotica.

After hearing the story of how Crystal and Heather both fucked her friends father and especially after hearing how endowed he was, she could only think about what it would be like to be with him. A few days later something occurred that would give her the opportunity she had always wanted.

Her opportunity to fuck her friends father came together after she learned the entire cheerleading team was invited to a weekend stay-over party at one of the cheerleader's, Tiffany's house. There would be boys from the school who were on the football and basketball team who would also be staying over, as Tiffany's parents would be there to supervise.

Knowing Hailey would be out all weekend; because she agreed to do a paper for her and three other girls going to the party she came up with the perfect plan. During the week there was a basketball game. Haileys father came to the game and like all the cheerleaders, female teachers and girls in the seats their hearts started racing a million miles a second once they laid eyes on him. Dressed in a fitted Italian suit he looked like a professional model.

Getting up her nerve the nerdy, Kate went up to him and said hello.

"Well hello Kate,"

"Uhh, hi Mr. Kane," she said in her meek voice.

Being polite he asked her about school then told her she should come over for a swim again soon with Hailey. Kate had been to Hailey's house a few times and had been at the pool when he was there. Seeing him in his bathing suit had her teenage pussy as wet as the water she swam in. Noticing her rock hard nipples poking through her skimpy bikini top made him grin inside as he knew she was imagining being with him.

The seventy year old, Ted Kane had experience with every type of young teen and it was always the soft-spoken and shy types that fooled everyone. He had a very good idea that the shy and innocent bookworm teen had a side to her that her boyfriend and all her friends didn't realize and would have been shocked about.

Taking a chance she asked him if he would be home for the weekend as she had to drop off a paper for Hailey.

"Umm, Mr. Kane, by chance will you be home this weekend?" "I have a paper to drop off for Hailey."

"Well yes Kate. I'll be back from a flight on Friday and will be in the entire weekend," he said as he deliberately scanned her body.

Sensing her thoughts he added," And Hailey's mother will also be at a convention in New York this weekend, so why don't you come over after Hailey is gone," he added with a sly grin.

Excited beyond words that she would be alone with the man she had nightly fantasies about she smiled from ear to ear. Her smile showed her silver braces and caused his mammoth cock to stir as he imagined fucking the teen friend of his daughter.

"Why don't you give me your cell number Kate and I'll call you right after Hailey leaves," he said as he took out his phone.

"Sure Mr. Kane, she said almost blushing as she gave him her cell number and watched him type it into her phone.

After giving him her number he said in a strong, confident voice," And why don't you bring your bathing suit so we could enjoy a swim in the pool, Kate?"

"Umm, I really like the sound of that, Mr. Kane," she said in a voice that suddenly had a lot more confidence in it.

He then took her breath away when he asked if she had plans for the weekend.

"Well just Saturday night I made plans to go to a movie with my boyfriend," she said but then grinned slyly, showing her braces, but added sheepishly, "but I could cancel."

"Something tells me that would be a great idea Kate," he said as he scanned her rail-thin body up and down in a way that sent her a very clear message.

"I'll call him later," she said in a throaty voice as the thought of being with her best friends father for the weekend made her body really excited.

" Maybe you should let your parents know you'll be out for the weekend staying at Hailey's house studying for an exam," he said looking her in her eyes, "tell them to call me and I'll let them know it's perfectly fine," he said in a deep, resonant voice.

"I will, Mr. Kane," she said biting her lower lip as she felt her nipples turn rock-hard.

During the game all she could think about was her friends father and how she couldn't wait to get the call from him that his daughter had left for the party. Her body was tingling in ways she never experienced just from the thought of being with him.

Although she came across as nerdy and shy, the young teen was far from being a prude. Although she had a boyfriend who was also the schools resident geek they never did anything more than kiss and hold hands. She on the other hand had fucked a number of older men who worked from her fathers limousine businesses.

One guy she was really drawn to was, Dan. He was fifty eight years old and was really good looking and in great shape. He was one of the drivers that picked her up from school. When Dan met Kate his impression was the same as everyone else's; Bookworm type. Along with being very plain looking, with very pale skin that looked like it had never seen an ounce of sun she was rail thin with a boyish shape.

She always dressed very plainly, in long skirts that went past her knees, and with her hair always in pigtails. She wore big, wide glasses and always wore unflattering flat shoes. Although he tried to make pleasant conversation with her, she mostly spoke in single word answers, 'yes,' 'no,' and 'I don't know,' being the extent of her replies.

Dan drove her every day for almost a month, with no conversation to speak of until one day she asked him to pull into a convenience store. Five minutes after she went into the store he saw a teenage girl come out that he couldn't take his eyes off. She was an absolute sexy, knockout that walked towards the limo.

The hot teen came out wearing the shortest pair of frayed shorts that clearly showed her long, thin legs. To further draw attention to her sexy, long, thin legs she wore a pair of black high heel pumps which added to the excitement of her amazing legs. Her wavy brown hair was down and she had on a white sheer blouse that was tied in a halter, exposing her flat, tight stomach. In her belly button was a diamond stud. It was clear that she was braless because he could easily see her ultra-flat chest and big pink nipples from 100 feet away.

The incredible sexy teen walked right in front of his limo. She was talking on her cell phone as he took in the sight of her amazing body. Those long sexy, tapered legs, so pale and looking even naughtier, because of the black high heel pumps she was wearing, was making his huge cock very excited and wanting to fuck.

She seemed oblivious to him starring right at her as she talked on her cell phone. As he took in the sight of her amazing body and her sinful look he had no idea that he was looking at the nerdy daughter he had driven to and from school for over a month. She was pretending to talk to someone, knowing the whole time that his eyes were all over her wild body.

She then crossed one of her high heel pumps over the other and bent at the waist pretending to laugh during her fake conversation. He went crazy seeing her torn, ultra-short shorts creep up into her pussy and totally expose her sexy, round ass to his face. The sight of her incredible ass cheeks exposed to his eyes and her sexy long legs in those classic black pumps made his huge eleven inch dick ready to explode.

She stayed in that position for a few minutes, allowing him to savor her incredible ass and legs. She then turned to the side and his eyes nearly popped out of his sockets when he saw her flat, braless tits and her inch long nipples sticking right through her sheer white blouse. Now with a raging hard on, he still had no clue that this was the same teenager that he had been driving for over a month.

As she walked away from the front of the limo and out of his view he suddenly began to wonder where the nerdy bookworm was. All of a sudden the side door opened and the smoking, hot teen he was staring at got into the plush back seat. His huge cock was just about to rip through his pants as he watched, speechless as she crossed her amazing legs. Suddenly he put it all together and realized that the nerdy bookworm was the same smoking, hot sinful teen he was raging to fuck.

He could not believe his eyes at the transformation from nerdy bookworm to ultra-sexy and smoking hot and very fuckable teen.

When she got in the car she didn't say a word, and went back to reading a book that she was reading during the drive. He was speechless and didn't say anything and he just drove off. As he drove he kept looking at her in his rear view mirror and couldn't take his eyes off her sexy crossed legs and her braless tits. Even the way she purposely dangled her high heel pump was driving him crazy as he saw the high arch in the middle of her shoe clearly exposed.

After a few miles she smiled slyly at him. Her braces only made her hotter.

"So Dan, do you like what you see?" she asked in a throaty voice that had him almost cumming in his pants.

"You are fucking amazing," he groaned in response as his eyes leered at her smoking-hot body.

"Do you like my legs," she said with that sly voice as she turned to the side and crossed them and ran her finger nail up and down her thigh to her high heel pump.

His eyes were bulling out of his sockets and his eleven inch cock was bulging, wanting to be released.

"Very sexy," he snarled.

"The high heels too?" she teased as she dangled the size ten pump from her foot.

"Oh fuck...you are so hot."

She then knelt on the seat with her ass to him and asked if he liked her shorts. As she asked him she ran her manicured nail along her ass cheeks. He was groaning in a low voice.

"Fucking wild ass," he groaned as he watched her every move.

She then turned back around and as her nails circled her non-instant tits asked,

"So tiny, aren't they?" she said in a naughty voice as she showed her braces while licking her upper lip. "Do you wish they were bigger," she added in a raspy voice.

"Fuck...they're fucking perfect," he growled as his hand was now rubbing his huge cock through the confines of his pants.

"My nipples are big though, aren't they?" she groaned then started to pinch them causing him to almost drive off the road.

"You know, Dan I overheard a conversation from my mother who told her friend that she was fucking her driver and that he had the biggest cock she'd ever seen or fucked."

He was in fact fucking her mother twice a week for almost a year. After Kate overheard the conversation, she was instantly turned on to fuck him.

"So, Dan would you like to find out if I fuck as good as my mother," she asked in a teasing voice as she continued to circle her tiny tits wither finger nails.

He immediately drove to her to a repair garage that her father owned, and parked the limo and got into the back seat and for the next three hours fucked her like a wild man. He was so turned on to her that he came five times without ever losing his hard on.

As he fucked her he was amazed that her pussy could take him so deep and with little resistance. Her mother, like so many others he fucked could barely take more than a few inches of his huge cock. As he fucked the hot-skinny teen his mind was racing from the thrills that were shooting through his big cock. 'Fuck. Never had a pussy so good,' he thought to himself as he slammed his giant cock to the base with pile-driving force.

Before he fucked her he told her that he had a vasectomy and she laughed and told him that she was on the pill, letting him know that she had been fucking for some time already. As he was pounding her senseless he couldn't believe how she took his enormous cock. He had fuck hundreds of eighteen and nineteen year old teens in the last few years and no one took his monster cock as easily as she did.

"Fuck you can really take a big cock baby," he snarled as he pounded into her, way back into her deep pussy.

"My grandfather has a real big cock too," she blurted, letting him know who she was fucking.

Kates grandfather was her mothers father. He was a very rich International banker who was 85 years old. He was responsible for getting her fathers limousine business started and also responsible for everything her family had, including a home in Beverly Hills, expensive cars, spa's and country club memberships and private school for her.

At 85 he looked decades younger. In fantastic shape from being a swimmer he was also very distinguished looking. He was always in the company of very sexy women, most of which were eighteen or nineteen, but never more than early twenties.

Kate was fucking him for months. She worked for him after school as an intern, and they started fucking on her eighteenth birthday a month earlier. One day when she came back to his private office because she had forgotten her book bag and caught him fucking one of his 20 year old secretaries. The sight of her grandfather fucking turned her on like crazy but even more when she saw the size of his cock. It was massive! Measuring twelve inches long and easily eight inches around, her grandfathers cock was a thing of absolute beauty to her.

The secretary had just gotten married and was back from her honeymoon. When Kate got out of the private elevator that she heard grunting sounds coming from her grandfathers private office. She could not believe the sight, as she watched in disbelief, as her grandfather pounded his incredibly huge cock into his secretaries pussy as she bent over his desk, with her tight skirt bunched up over her ass, as she stood in nude thigh high stockings and brown open toed high heel pumps.

She watched her grandfather fuck her so hard and like crazy for over an hour. It was a ruthless side to his personality that came out as he fucked. As she watched in total excitement she could not believe the size of his cock and his huge, hanging balls.

She watched in total disbelief as the girl shuddered through more than fifty wild orgasms as she shouted to her grandfather how much she loved fucking his huge cock, and that even while she was on her honeymoon all she could think about was getting back and fucking him.

She watched her grandfather cum all over her four times during the wild fuck, shooting a huge load that went from her ass, to her back and even into her hair. As soon as he came she squatted on her pumps and jerked him to another huge hard on until he sprayed all over her tits and her hungry mouth.

The next day was her eighteenth birthday and her grandfather was taking her to dinner at the exclusive club he belonged to. After work she changed from her nerdy school cloths into a skin tight, black mini dress that came down just below her ass. She wore nude thigh high stockings and high heels to highlight her long tapered legs and went braless. She really wanted to turn him on.

The material of her dress, although black, was so sheer that you could easily make out the skin tone of her braless tits, and because her nipples were huge they stuck through the fabric and made her look absolutely sinful.

As soon as she went into his office his eyes were all over her, with a hunger that caused his huge cock to balloon out. Knowing it was his granddaughter, but not recognizing her new, drove him wild. He knew why she dressed this way and he had to fuck her.

The sight of her long tapered legs accented by the nude thigh high stockings and the tight mini dress that showed her big nipples, and the sexy, classic black high heel pumps, caused him to get instantly hard. For the next minute he just took in the sexy sight of her from her pumps, up her sexy legs, to her huge nipples that were straining through the sheer material of her ultra-short mini-dress.

As he took in the sight of his smoking-hot granddaughter his twelve inch cock turned angry in his pants, pushing the material way out. As he was leering at her, she was staring at his enormous bulge, happy that she was what was turning him on. Within seconds they were kissing and for the next four hours they fucked in every position in his private office.

Her grandfathers great big cock was responsible for really stretching her out. To date she had fucked a few boys her age and her English teacher who was black who she babysat for. But none of them had a cock half as big as her grandfather, or fucked her as nearly as hard as he did. Even at 85, he was in better shape than all of her young boyfriends including the sports jocks, and he fucked harder than all of then combined, including the forty year old, black English teacher who had a real big cock.

Dan fucked her every day after school for almost a month, where she would change into something real sexy, and they would fuck for two straight hours. One day she came out in her conservative cloths and told him they had to stop fucking. He was devastated when she told him the reason was because she couldn't cheat on her grandfather anymore. It was a lie because she had plans on fucking her friend Hailey's father that weekend.