Sinful Degrees of Separation

Special mention to Hatsuda for editing this series

In this story, knockout teen cheerleader Hailey meets an overweight and balding sixty-eight year old family friend in a trendy bar. He also happens to be the father to her ex.

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Her remarkable vital statistics, standing 5' 6" tall, weighing 110 pounds with measurements of 36DD-21-33 made the 18 year old cheerleader an absolute knock-out and every man's ultimate fantasy. Despite boys her age or older constantly asking her out, and older men in their 40's and 50's, even into their 80's offering to pamper and spoil her when she was out with friends at a trendy club, her thoughts were on her distinguished and very handsome father. Although she had boyfriends and was currently dating the star quarterback her mind was consumed with her distinguished seventy year old father.

One night she asked her father to come to her bedroom to give her his opinion on which pair of stockings would look the best on her. She had him and her mother believing she was going to a dance club with friends. Where she was really going would have shocked them both. Where their sexy eighteen year old daughter was going, dressed in a sinful mini dress with stockings and high heels, was to their very close friend, sixty-eight year old Will Powers. He also happened to be the father of her ex-boyfriend.

Will Powers was a wealthy billionaire who had been divorced for over fifteen years. He had a son named Josh who the sexy stunner had dated for almost a year when she was sixteen and he was eighteen. He was currently away at a very affluent private college on the east coast. She, having dated his son for almost a year and he, being good friend's with her parent's resulted in her visiting his home a lot and knowing Mr. Powers really well.

Although close in age to her father he wasn't even close to being anywhere near as handsome or in the physical shape of her father. In fact the wealthy Mr. Powers was the exact opposite of her father, being short in stature at 5'6"tall and way out of shape, weighing over 250 pounds.

Because of his height and weight he had the look of a Buddha statue, but if comparing him to a porn star, he more closely resembled the iconic Ron Jeremy, having a similar sizable belly and noticeably balding head of black hair. He had a mustache which drew attention to his large nose, a chubby face that looked bloated, showing bags under his eyes, and a substantial double chin. The sixty-eight year old friend of her parents and the father of her ex was definitely the opposite of her handsome and distinguished father.

In spite of his being overweight and having a chubby, bloated face he always had a sexy girl between eighteen and nineteen on his arm. He was very wealthy, contributing millions of dollars to a variety of charitable organizations, and was often seen at Galas, being one of the main benefactors making sizable contributions in the millions. Even at sixty-eight and retired, he was still active in his very lucrative business and still attended many corporate meetings of companies he still owned.

One night, while out at a trendy club he saw the knockout teen ex-girlfriend of his son. She was also the daughter of close friends, and was on the dance floor with some of her High School friends. He watched her with absolute rapt attention as she danced with a few of her girlfriends, dressed in a sinful mini-dress that was molded to her perfect body showcasing her amazing ass, her long tapered legs and her large, ample breasts.

'God what a body'

, he thought to himself, as he sipped his drink. He watched her moving on the dance floor, her smoking-hot body captivating every male present and even a lot of females. '

One of the few of Josh's girlfriend's I didn't get to fuck',

he thought to himself regretfully as he sipped his glass of wine, watching her amazing body.

His eyes were glued to her body starting from the most incredible pair of long tapered legs to her narrow waist then to her huge breasts which seemed to defy her slim frame. He watched her dancing with her drink in hand, unable to take his eyes off the amazing body of his good friend.

As she swayed to the music her eyes caught her ex-boyfriend's father sitting at the bar, deliberately watching her every move. Having known him for years as a very good friend of her parents and the father of her ex-boyfriend, she now saw him with his eyes glued to her body. He stared at her the way a guy looks at woman he wants to fuck, and it made a sudden thrill go through her body. As their eyes locked onto each other's, it seemed as if they were the only two in the room.

As he sipped his drink he caught a knowing look came over her face. It became apparent to him that she knew the effect that she was having on him, and began to see possibilities for some future adventures.

Being a little tipsy and knowing her ex-boyfriends father was watching her every move, she began to dance more deliberately, running her hands up her sexy hips to the sides of her amazing 36DD breasts, and even over the back of her delicious ass.

'Oh Mr. Powers you naughty old man. I see you looking at me. Now that I'm all grown up. That's right, I'm 18 now Mr. Powers'

, she thought to herself. She was really feeling the effects of the alcohol now and loving the fact that he was drooling over her.

Grinning coyly at him while she moved to the music she pursed her lips and blew a soft kiss at him as a way to let him know his rapt attention to her every move was exciting her. He nodded his head in return as if to say that he knew he was dancing for him.

After the song ended the girls finished their drinks and began walking out of the club giddy and a little unsteady, undoubtedly due to them having had a few too many drinks. They were all wearing high heels as well, which contributed to their unsteadiness as well. Deciding to say hello to her ex-boyfriends father, she walked to the bar where he was sitting and gave him a warm hug.

"Hi Mr. Powers," she said in a slightly slurred voice. "Wow! Surprised to see you here."

"A nice surprise I hope, Hailey," he said, wrapping his chubby hands around her narrow waist.

"Yeah, but just don't tell mom and dad," she said with a wry grin, pulling away from their hug.

Even though she pulled away from hugging him he kept his hands on her waist. He noted that she didn't seem to mind and even gave him a nice smile.

"Our secret, I promise," he said with a devilish grin, sliding his hands from her waist, to her hips, and then over her stocking covered thighs.

Although a little light headed from the alcohol she still felt a tingle in her body from the way his hands seemed to boldly lay claim to her body.

"Pinky promise, Mr. Powers?" she slurred, hooking her index finger around his.

"Pinky promise, Hailey," he said with a little chuckle.

After hooking his finger he asked her to join him for a drink. Agreeing, she sat on the high bar stool beside him. As she sat she watched his eyes immediately drop to her long, tapered legs. On impulse, she crossed them and he instantly saw the lace top of her thigh high stocking as the ultra- short mini dress went way up her thigh. Mr. Powers' looking at her legs with a hunger in his eye suddenly made her feel very sexy.

Since her friends were waiting for her, she told her Mr. Powers that she had forgotten that she rode with them.

"I'll be happy to take you home, Hailey." He responded.

"Wow! Okay, Mr. Powers," she said thinking it would be nice to catch up with him.

She then signaled for one of her friends, Casey, to come over and told her she was going to get a ride home by him. Casey, along with a lot of her friend's in the group knew the older man from her dating his son and being good friend's with her parents so they left knowing she was in good company.

Another girl in the group, Shannon who also walked over to say hello to him. She was also an ex-girlfriend of his son, who'd one month ago spent an entire weekend fucking the overweight sixty-eight year old billionaire as she went insane for him.

Shannon was also a cheerleader and he knew her parents. Although she was eighteen she looked more like a twelve year old with a rail-thin body that couldn't weigh more than eighty pounds, with a flat-as-a board chest and tiny pink nipples with no discernible areola around them.

Standing 5'6" tall with freckles covering her body, wearing braces and always in pigtails, she was the image of an adolescent when dressed in casual clothes, but on a night like this when she was dressed in a skintight mini-dress and high heels she was every older man's teen fantasy.

If he didn't want to fuck the sexy stunner sitting next to him on the bar stool so bad he knew he would have taken the rail-thin eighty pound Shannon home and pounded the fuck out of her. His confidence came from the numerous text she had sent him after their sinful weekend telling him she missed being with him. In those texts were always pictures for her dressed in the naughtiest bikinis with high heel pumps or sexy lingerie.

As Hailey told Casey that she would be getting a ride home from her ex-boyfriends father, Shannon shot him a sly grin as if to say she wanted to fuck him. She even went so far as to hold her cell up and bat her eyes as a gesture for him to call her. While the two girls talked the 80 pound ex of his son started talking to him.

"Hi Mr. Powers."

"Hello Shannon"

"Surprised to see you here," she said in a little tipsy voice.

"Well I have heard a lot about this club and decided to come see what all the fuss was about.

"Umm. It's really nice to see you here," she said gazing at his crotch as she hungrily thought back to her weekend with him.

"Thank you and I have to say that I really love the dress you are wearing," he said as his eyes scanned up and down her body as he imagined her out of it with her flat-as-a board chest with the tiniest pair of pebble-stone nipples.

Like a lot of his son's girlfriends he had fucked the teen on a weekend one month ago while her parents were away and his son was at a sports camp. Although she was barely able to take half of his massive cock they fucked non-stop all weekend long.

During that weekend she'd told him over and over how she wanted to be his and that she would even break-up with his son. It was something he had heard hundreds of times from his son's girlfriends and other young teens once they fucked his huge cock.

The thought that these teenage girls who were still in High school willing to leave their parents' home to move in with him was amusing. Of the hundreds of endless teens who woke up in his bed the one he would surely accept if she asked to move in with him was the stacked and sexy ex-girlfriend of his son, Hailey Kane.

For years, since she first started dating his son, she was constantly on his mind. Her knockout body was pure perfection, and even while he pounded his twelve inch monster into every other teen, her amazing body taking his huge cock always stayed in his mind.

Of course it would mean severing all ties with her parents who were his close friends, but it would be absolutely worth it to have the young, teen stunner wake up every morning in his bed. His son would also be furious but knowing he could lose his multi-million dollar trust fund he was currently receiving he would be forced to love the idea of his ex-girlfriend living with his father.

As he listened to the sexy stunner tell the bartender what she wanted, his eyes scanned to take in the sight of her amazing body. Gazing at her incredible legs, narrow waist and big, suckable breasts he thought to himself how much he'd love to fuck the knockout teen. It wasn't the first time he'd had these thoughts about this hot teenager.

By a very young age when girls were still in training bras her body had already developed to the point where she was smoking-hot. The day his son brought her home when they started dating only increased his thoughts of fucking her, especially when she was at his pool wearing a bikini that barely covered her nipples and the front of her pussy. The thin string that went between her gorgeous ass cheeks was enough to give him a heart-attack. He'd learn later that she always wore a sinful bikini to catch his eye, as she had seen numerous other teens he'd dated wearing the most devilish bikinis and high heels when they were at his pool.

"I watched you dancing Hailey, and I have to say that without question you are the sexiest girl in this place tonight," he said, his eyes traveling up her crossed, stocking covered legs.

"Thanks Mr. Powers. I turned eighteen two days ago and my friends wanted to take me out to celebrate," she slurred.

"Well eighteen; such a perfect age," he replied with a little knowing laugh. It was apparent to her that he was letting her know she was now a legal fuck.

'Wow. Mr. Powers is really coming onto me'

, she thought, as her recollection of him being her parents close friend, and her ex-boyfriends father made her a little excited and she felt a spark ignite in her pussy.

While she listened to him chat about having just seen her parents at a dinner party she thought that he had a nice personality, but did nothing to convince her that he was anyway handsome or distinguished. Still, she was always surprised to see that he always had a bevy of young teenage girls on his arm. She always remembered him going out on dates or to functions in the community with very sexy girls and figured it had everything to do with him being a wealthy billionaire.

As she looked at him she did admit to herself that she imagined being on his arm more than a few times when she thought about how wealthy he was. There were even times when she was at his mansion-like home and imagined what it would be like to be Mrs. Will Powers. She also had a very good idea that he had fucked his son's recent girlfriend, her friend Shannon. She had heard that a friend of his son had gone over to leave a package for Josh when he came back from college and had seen Shannon's car in his driveway.

"Yeah, eighteen... Definitely old enough for a lot of fun things but not old enough to be in this club and especially not on a school night," she said with a pleading look, reminding him not to tell her parents.

'What a body. Sexy legs and the most amazing tits'

, he thought while the bartender mixed the drink she asked for. His cock was stirring in his pants and he could tell by how giddy she was that she'd already had a few drinks in her. This was just fine with him, especially as he thought about how much closer he'd be to taking her home and fucking her.

When their drinks arrived he toasted to her looking very sexy, saying he always thought she had an amazing body and was definitely the hottest looking of his son's girlfriend's. Loving the compliment from her ex-boyfriends father, she held her drink, leaned in and gave him a fast kiss on the lips.

"You're so sweet Mr. Powers," she said just before she kissed him.

Even with the fast, peck-like kiss he instantly felt his body come alive and his cock stir in his pants. She herself had felt a tingle throughout her body which surprised her a little. As they talked about his son and how he was doing in college she noticed his eyes roaming all over her body with a hungry, lustful look that instead of making her feel a little uncomfortable, made her feel sexy.

Seeing her dressed in the sinfully tight white mini dress that came just below her incredible ass showcasing her incredibly long, tapered legs was causing his breathing to speed up. Her classic black pumps drew even more attention to her amazing legs as she sat with her left pump anchored to the bottom rim of the high bar stool while her right leg was crossed over it.

She wore that sinfully tight dress because her father was home from a flight and she wanted to turn him on before she went out. For the past year she was having the most sinful thoughts about her and her handsome father and at every opportunity when he was home from flights she would purposely dress to excite him. Of course a lot of this had to do with her knowing her father was a magnet to teenage girls and that she recently found out he'd had fucked three of her best friends.

While they were talking she watched his eyes roam deliberately up the length of her stocking crossed legs, starting at her black high heel pumps which showed the high arches in her feet. Watching his eyes travel slowly up her narrow waist right to the top of the dress, accenting her luscious 36DD breasts started to really excite her. The fact that he didn't hide his stare from her excited her even more

'Ummm. I'm glad you like what you see Mr. Powers'

, she thought and for a second playfully imagined herself as one of the many teenage girls that she saw on his arm. At that moment he was having similar thoughts as his eyes continued to roam over her amazing body.

As they talked he motioned with two fingers to the bartender, who quicklybrought over a new round of drinks for them.

"Such an amazing body Hailey," he said clicking his glass against hers in another complimentary toast that had her grinning widely.

"Umm. Thank you Mr. Powers," she said, watching his eyes go up and down her figure, knowing he wanted her.

Being drawn to him she then leaned in and gave him another kiss on the lips, but this time let it linger a few seconds, ending it by running the tip of her tongue across his lips.

Even though he attributed her gesture to being a little inebriated from her night out with her friends, the kiss caused his big cock to stir even more as he imagined it sliding in and out of his good friend's daughter's pussy.

As she was sipping her second drink he said something about his son being crazy for letting her get away and commented that 'he must be gay.' This caused her to laugh and as she was laughing he put his hand on her thigh, sending a spark up her body.

Being even tipsier now, she was beginning to really enjoy hearing her ex-boyfriend's father whisper in her ear about how sexy she was and telling her he wished he was fifty years younger. Leaning in while holding her drink she whispered in his ear and told him she liked hearing him say that she was sexy then told him that fifty years was a sexy difference in age.

Feeling his hand go above the trim of her nylon tops to her bare skin caused her to throw her head back a little and bite her lower lip.

"Umm... that feels so nice Mr. Powers," she whispered, feeling his hand on her upper thigh send sparks through her body in a way she never felt before, certainly not by his son, nor her current boyfriend.

While he was telling her this, he continued to trace his finger along the edge of the lace trim and her nude flesh with a very lustful grin on his face.

"Are you feeling sexy tonight Hailey?" he asked as his finger slowly and deliberately traced the lace top of her thigh high stocking going around the edge from the bottom of her thigh over the top just a few inches away from her pussy.

Feeling the trill of his finger she threw her head back a little and pursed her lips showing her excitement.

"Oh God, that feels so sexy Mr. Powers," she whispered before playfully biting his earlobe.

After buying her another drink he asked her to dance. It was a slow song and as they walked to the dance floor he had his arm around her and noticed that her legs were a bit shaky. In her high heels she was easily four inches taller than him.

Although he was overweight, she was impressed with him as a dancer and even complimented him. Swaying to the slow love ballad she felt his hands drift from her narrow waist, run up her hips then over the sides of her stocking covered thighs to her lower back. They then dropped even lower to the tops of her ass cheeks.