Father & Son, Mother & DaughterbyNYBoss©
As the romance blossoms, the sex ignites. This story is much longer than my previous stories. You will get a little taste of sex early on and as the love story continues to build and the relationships develop your patience will be rewarded.
Joshua Stern rode up the elevator to the 10th floor of the office building located at 475 Madison Avenue in New York City. He was meeting his dad Rich who is the CEO of JJ Promotions to discuss their upcoming vacation to Key West. Rich was very low key, so much so, that his name did not appear on any of the company web sites or social media outlets. He liked it that way. It enabled him to do business without telling people what his business was.
Joshua just finished his medical training and is working as a cardiologist at one of New York City's teaching hospitals. Ever since his mom passed away from a congenital heart condition while he was in high he decided to pursue a career in medicine, specifically in Cardiology. And while his dad had expressed the desire for Joshua to work in the family business, his dad was just as proud as his son was on his way to a great career in medicine. His sister, the other J in the JJ Promotions Company, was Jessica. Jessica Block was the President of the company her parents founded some twenty-five ago. Jessica was the face of the company. While Jessica was three years older than Joshua they were the best of friends. Jessica's husband, Mark was the CFO.
Every year Rich took the kids away for a family vacation. Last year it was skiing in Utah, this year the kids wanted to go some place warm. Unfortunately, Jessica was tied up with a very important client and would not be able to join her brother or dad this time. So it was only going to be Joshua and his dad on the April vacation this year. Rich promised his daughter that they would find time to get away during the summer. Jessica did not give this a second thought.
As Joshua got off the elevator on the 10th floor of the office building owned by his dad, his dad's administrative assistant, Holly Sanders, met him. Holly had been with his dad ever since he founded the company. Holly also happened to be the women with whom he spent many an evening, while in college and through medical school, fucking at either her apartment or his. Holly was a single, fun loving woman who only recently found the love of her life. She met her soul mate Jonathan at a business meeting a few years ago and finally, after years of remaining single, surprised everyone by tying the knot a few years ago. Everyone in the office was happy for Holly.
A striking redheaded woman with a curvaceous figure, Joshua knew Holly from the time she started working for his dad and all through puberty developed a secret crush on her. What was not to like. The stunning red head turned heads wherever she went, especially when she sat in on business meetings involving his dad and potential business partners. She never went over the line with business associates but Joshua did not, at the time, know that Holly had a preference for robbing the cradle and set Joshua in her sights. And while her boss was off limits, Joshua was another story. She decided it would be better to wait until Joshua was in college.
As he approached Holly he remembered their first day fucking as if it were yesterday. It was after the annual company holiday party during his winter break from NYU. While Joshua had a choice of colleges to attend, he wanted to stay close to his dad and sister, especially with his mom no longer around. Holly asked Joshua to walk her home from the party and at his dad's instance, did so. After walking her home, she asked him to come into the apartment under the false pretenses that she needed someone to take a look at a leaky faucet. Joshua was holding a flashlight, looking into the kitchen sink's cabinet looking for the leak.
"Holly, I can't see any problem here! Holly, he called again," but did not get a response. He pulled himself up from the floor only to be startled by the fact that Holly was standing in front of him, totally naked.
"Are you ready for your holiday present yet," Holly said as she posed with her hands on her hips, large tits, with nipples hard thrust out and with a flaming bush the same color of the hair on her head. Not bad for a women in her forties.
"I must admit, that you have been the object of my fantasies for a few years now."
The one thing Joshua never lacked was self-confidence, especially with women. He was a sturdy 6'2" and solidly built and very good looking. He never had problems with meeting women as they usually went out of their way trying to be with him.
"Well, do you want to act on those fantasies or just continue to stare at me?"
Joshua moved closer to her and pinned her arms behind her, holding her wrists together with one hand. He gradually moved his other hand over her tits, teasing her nipples and took his time moving down until his hand was over her thick pelted bush. He brushed his fingers across the coarse hair until he pried her legs apart. Gradually he moved his finger in and around the opening of what was now a very wet cunt. He began to finger fuck her slowly, ever so slowly.
"Oh my, that feels so fucking good."
Holly started to undulate her hips to gain maximum effect of the probing fingers. Joshua moved his fingers from her cunt to the clit that just began to peek out of that dense forest of hair. While he began to tease her, causing more and more animalistic sounds to emit from Holly's mouth, he decided that he had to taste this hairy cunt.
Joshua kneeled on the floor and separated Holly's legs so that they were straddling his shoulders. He took the tip of his tongue and started to move it up and down her moist slit, only touching the clit infrequently. Every time his tongue found Holly's throbbing clit, she shuttered and continued to hump her cunt against Joshua's face.
"More, more don't stop." And just as suddenly, her legs felt weak as she experienced a might orgasm. "Oh, yeahhhhhhhhhhhhhhhhhhhh. Yes, Yes, coming, coming" as she grabbed his shoulders for support.
Just as her orgasm began to subside, Joshua turned her around, bent her at the waist and kept he in that position as he unfastened his pants, letting them and his underwear fall to the floor. His cock was so very hard. And with one quick thrust, he shoved the 7' spear into the hairy snatch he had just eaten.
"Oh............., so big, so fucking big. Now fuck me, fuck me hard. Oh................"
Joshua had started having sex when he was a young kid, having lost his virginity to his nanny when he turned eighteen. The nanny taught him how to please a lady and he was an expert in doing so, even as a young man.
Joshua, began slowly, but then picked up the pace as he raced to provide Holly with a second orgasm as his cock was ready to shoot.
"Coming again, so fucking good. Harder, coming again."
"Come in my cunt, in my cunt. Want to feel you. Oh, I feel your cock getting bigger."
Both of them came with a loud cry, with Joshua spilling his seed into Holly's cunt and onto her bush. Holly held onto the sofa and Joshua held onto Holly as they began to come down off of the instant fuck.
A few minutes later they moved apart, panting heavily.
"The reality was much better than the fantasy," Joshua laughed.
"I've never been so thoroughly fucked," Holly said while continuing to stare at Joshua's deflated cock. "Even like this," she pointed to his flaccid cock, "you are huge."
They spent the rest of that night fucking and sucking each other into many orgasms. Joshua loved her hairy pussy, especially when she rode him in a reverse cowboy as her image was reflected into the mirror on the ceiling, over her bed. He loved the way her bush spread out over her entire mons. While she kept her bush trimmed on the sides, she never bothered to thin it out as the hair spread from the top of her pubis, in an inverted "vee" toward her rear end.
They continued to share a bed from time to time as Joshua moved through college and medical school. Their relationship was based on the passion of sex. There was many a night when all Holly wanted to do was suck his cock and have him cum on her bush. The sex was spontaneous and passionate. Nothing more and both understood and accepted those conditions.
Joshua was jolted back to the present, when Holly yelled to him, "Joshua, Well hello!"
Joshua blinked and said, "Sorry, I was day dreaming." He walked over to Holly and greeted her with a kiss on the cheek. "How have you been?"
It had been a few months since Joshua had been to the office as he had been busy with his work in the hospital. Joshua and Holly continued to make small talk, with Joshua asking how her husband was doing and making sure he complimented her on how she looked. The passion in both of their eyes was present, it would never go away, but both knew that they would no longer act on it, as Joshua was happy that Holly had found someone to love.
He had come to the office to finalize the last minute plans for their trip to Key West that was starting tomorrow.
"Your dad will be with you in a few minutes. He is going over some last minute items with Jackson," Holly remarked.
Jackson Freed was the head of the HR department. They had an opening for a Director of Events Planning and they wanted to fill the position sooner rather than later. They had a number of projects in the works but needed someone to take them from the planning to the implementation stage. The previous Director had left the company to return to the west coast to go into his family's wine producing business.
In a few minutes Jackson walked out of his dad's office, stopping to say hello to Joshua. They too, caught up on Joshua's work.
"Good to see you again Joshua. You know, and this is something that you probably already know, that your dad thinks the world of you and could not be happier with you becoming a Cardiologist."
Joshua had met Jackson when he came on board a few years ago and always thought very highly of him. When there was an opening for a key position within the company, Jackson seemed to work magic finding the right person to fit in with the culture of the organization and with the right qualifications.
"Thanks Jack. How's the family doing?"
"Doing very well. Fred is about to become the number one pitcher on his high school team and Betty is playing on the varsity soccer team as a freshman. Abby is also doing well." Abby was his wife who was our family dentist.
"That's great. Remember I want tickets to the games when he starts pitching for the Yankees!"
"You are on the list," Jackson laughed. "You and every other friend and relative I know."
Just then, Joshua's dad walked out of his office.
"Jackson, remember three resumes max, so I can review them on the plane."
"You'll have them by 3 pm."
Rich walked over to his son and embraced him. "Come let's go to lunch."
"Holly, I have nothing scheduled on my calendar. You can reach me on the cell if necessary. See you in a few hours. You want me to bring you anything?"
Holly nodded and said, "Nothing for me. Have fun."
"It was good seeing you again," Holly said to Joshua.
Joshua turned and smiled at her. Holly smiled back.
Over lunch the two of them discussed their trip that was going to begin with a flight to Key West via Miami the next day.
"It will be good getting back down to the Keys again," Rich said. "I need to spend more time down there. It is really a great place to eat and relax."
It had been two years since Rich and his kids were in the Keys. They had always liked the low-key, total uninhibited ways of Key West. From the lifestyle to the restaurants, Key West offered all that was needed to clear the heads of both Rich and his son. They were both working very hard and needed some down time. They were going to rent a house, but the one they had selected became "unavailable" at the last minute. Rich had called in some favors and was able to get a suite at the Westin Hotel, just off Duval Street.
On the plane flight Rich took the time to review four, not three resumes that Jackson had prepared for him. The Director of Events Planning was a position of great importance to the company. The company specialized in handling public relations for many public figures including the top athletes in the New York City area, politicians and celebrities. The other part of the business centered on the special events these people championed. The Director had to deal with the celebrities, their agents and their egos and put together successful programs.
Joshua looked over at what his dad was reading and noticed that there were no names on any of the resumes. His dad seemed to read his sons' mind.
"I deliberately leave the names off the resumes so I am not prejudiced by anything except by their experience and performance when I evaluate their qualifications. That way, I make the decision solely based on that."
"That makes sense. You get the best person and it saves you time."
They arrived in Key West in mid-afternoon. The late spring weather was perfect. With temperatures in the high 70's, there were no clouds in the sky. Perfect.
The concierge at the Westin showed them to the largest suite available. Complete with a small kitchen and three bedrooms it was better than the house they had originally rented. Plus the fact that there was a pool on the premises made it an ideal spot to chill out.
They settled in and headed for the pool. Later that afternoon they started to discuss plans for the evening.
"Dad, if you don't mind, I'm going to head to the Green Parrot Bar for a beer and some wings." I know you are meeting one of your golf friends for dinner at Louie's Backyard and don't want a long drawn out night. I'll see Bob another night."
"No problem. I'll catch up with you later, if it's not too late. Enjoy and be careful." They headed in different directions as Joshua had a short walk to the bar and his dad took a cab to the restaurant. With parking at a premium in downtown Key West, it was easier to either walk or take a taxi. When he arrived at the restaurant his cell phone went off.
"No, I understand. Don't worry we'll catch up another time." It was his friend Bob. He had become ill that afternoon and would not be able to join him for dinner.
As he entered the restaurant he began to move to the Maitre D who was having a lively conversation with a striking dark haired woman. "My friend was to meet me here and she had set up a reservation for the two of us. She left a message for me that I just received telling me that her flight was delayed and she may not make it for dinner.
After the woman gave the Maitre D her friend's name, he excused himself to check on the reservation book.
"I did see a reservation under your friend's name, but she called to cancel a few hours ago when she told me that her plane was delayed. I gave the reservation to a couple on our waiting list."
"You mean to tell me that there is no table for me?" The woman was angry with her friend for not telling her the reservation was canceled and she was angry with the Maitre D for treating her with indifference.
"I'm truly sorry, but we are completely filled up for tonight. Perhaps next week. Or you can sit at the bar."
"I'm only here for the week. Next week won't work," she screamed back at the Maitre D. The woman did not like the idea of sitting at the bar by herself, but if that was her only option she may reconsider. She contemplated the decision she had to make.
"Excuse me for a second," the Maitre D said to the woman as he noticed Rich. He greeted me like a long, lost friend that I was as I always come to Louie's for dinner at least once or twice while I am in town.
"She is quite animated," Rich said.
"Her friend screwed things up," as the Maitre D, explained the situation to Rich.
"I may be able to help you so this doesn't turn into a scene."
"Be my guest."
"Excuse me," Rich said as he turned to the woman standing no more than six feet from him. I heard your dilemma and let me tell you that if you don't have dinner here you will be missing out on one of the best dining experiences anywhere. The menu at the bar is the same as they serve at the tables. Granted, the atmosphere is not as good. The tables look over the gulf and ocean and at the bar you are only looking at the bartender."
As she pointed to the Maitre D, "I know that. That's why I am pleading with the man over there to find a table for me."
"There are no tables available, but I may have a solution for you. You see I was to meet up with a friend of mine for dinner, but he took ill, so I am by myself for dinner with a table reserved for two. If you want, you are more than welcome to join me for dinner."
She looked at Rich skeptically.
"I'm not going to bite. The owners can vouch for me. I come here whenever I am in town."
"Rachel Evans" she said as she extended her right hand.
"Rich Stern. Pleased to meet you."
They were lead to an outdoor table, overlooking the water.
"The view is fantastic," Rachel remarked as she looked over the vast expanse of the water in front of her.
Rich was smitten by this dark haired, middle-aged beauty. "It is from my spot as well."
He was looking not at the water but at Rachel. He had not only noticed her beauty the minute she appeared in the restaurant, but her sparkling green eyes made her even more beautiful. Wearing a tight fitting, summer dress, bringing notice to her full chest, she wore a few simple gold bracelets on her wrists and tasteful high heels.
Rachel, slightly embarrassed, turned a lovely shade of pink. She nodded in his direction.
Menus were delivered.
"What do you recommend?"
"Any fish on the menu is great."
The waiter came by and Rich ordered for both of them. He chose a great Chardonnay to compliment the dinner.
The small talk came slowly.
Rich told her that he was down for a little R & R with his son, hoping to do nothing more than sit by the pool, read a book or two and enjoy the fine dining and nightlife in Key West.
"Your wife doesn't mind you going to dinner with a strange woman?" She had glanced and nodded at his wedding band on his left hand.
He noticed her looking and said, "my wife died a few years ago, cardiac problems. I haven't been able to remove it just yet."
"No need to be. My two kids give me great joy. And you, out on the town without your husband?" He noticed and nodded at the diamond wedding band on her finger.
"Touché! Divorced for 10 years. It's easier to keep the ring on then to fend off unwanted advances, if you know what I mean."
"Kids," Rich asked.
"One great daughter who is finishing her medical residency in Ohio, where we come from. Applying for a few fellowship programs all over the place. She will find out in a days where she will continue her training. With her schedule it was difficult to plan a vacation. This trip was planned at the last minute.
"I take it she decided not to join you tonight?"
"She had never been to Key West and did not want to join me and my friend for dinner. She just wanted to walk Duval Street and grab a beer and some bar food."
"My son said the same thing. He is running around on Duval as well."
As her mom was enjoying dinner with a new friend, her daughter Emma was just entering the Green Parrott Bar. Dressed in a tank top that seemed painted onto her skin, Emma was blessed, like her mother, with an ample set of tits. The tank top did little to hide the impressive cleavage accentuated by the bra she was wearing. That along with a very short skirt and sandals, with just a touch of make-up, made Emma look stunning. Her hair in a ponytail framed her sky blue eyes. Heads usually turned when Emma walked into a room. Coming into the Green Parrott was no exception. However, she knew she was attractive and was able to handle unwarranted situations that came up on occasions whenever she went out to dinner by herself.