My Escort, My Daughter

This is an entry into the Literotica Winter Holidays Story Contest 2016. It is not a quick jerk story. Rather, the characters are fully developed, because I think it is important to know them as the story plays out. There are some graphic sex scenes, but for the most part, this is just a true, old-fashioned romantic story centering around three people.

This story also contains scenes of incest, so if that bothers you, please read no further. As usual, all of the events depicted in the story are fiction.

If you like this story, please vote. I also enjoy hearing your comments!

******

I pulled my phone out of my pocket to check the time. It was already 7:00. Damn, what was she doing back there?

The Christmas Eve party started at 8:00. Not that it was really important to be there on time. In fact, the way these parties usually went, it really didn't get started until an hour or so later. But I didn't like to be late. I guess that was something my parents had ingrained in me. And even though I knew how the game was played, I at least tried to play by the rules.

I really didn't want to go to this party anyway, but in my profession, you have to schmooze with the big money people if you wanted a chance to play with their money. And since my profession was all about managing their money, it was an event I needed to attend.

My name is Wesley -- not Wes, but Wesley. I own a financial management company. The party tonight is being thrown by one of my biggest clients. As parties go, it will be good, with some of the city's wealthiest in attendance. There will be some boring conversation, some really off-color jokes, and the best food spread prepared by the best caterers in town. It's the kind of party that would make the social section of the City Times -- except no press will be allowed within 2,000 feet of the club tonight.

But the biggest reason I did not want to go to the party was that my usual companion Rachel would not be attending with me. She had called me this morning and begged to cancel at the last minute. It seems her boyfriend thought it was important that she attend his family's Christmas Eve gathering. I'm not sure if he really knows what Rachel does for a living. If that's the case, I'd be curious to see how she explains to him about the money she makes. Maybe he doesn't know about that part of it either.

So at the last minute, I had to scramble to find someone I could convince to go with me. Since I don't really have a lot of attractive young women as friends, and since the agency didn't have anyone available as a substitute for Rachel (and to tell the truth, I probably wouldn't have taken a sub anyway), I called the only person I knew who could fulfill the "aesthetic" requirements of being my companion. It was her that I was waiting on as the clock moved past 7:00.

I glanced out the window of my 20^th story apartment at the city below. Given the Christmas Eve holiday, traffic was understandably light. It's hard to tell being up so high, but there might have been a few flakes of snow falling in an attempt to make the concrete-gray environment below seem more festive and holiday-like. One good thing about the light traffic -- it wouldn't take as long to get to the club as it normally did, and since someone seemed to be taking her own sweet time getting ready, that was a very good thing.

Finally, at about 7:15, she called out, "Be honest, tell me what you think!" She stepped out of the guest bedroom, and my jaw dropped -- she was the most beautiful creature I had ever seen! The extra minutes getting ready were well worth it!

"What do you think, daddy? Will I do as your escort for tonight?"

******

Sometimes life just isn't fair.

You work hard, you make plans, you start finding the components to make those plans into reality, only then to find out that sometimes reality has its own plan, and it doesn't ever consult with you. I wasn't expecting the penthouse apartment, the daily car service to take me wherever I wanted to go, the multi-million dollar business that makes its money by making money for other people. Certainly I have been blessed. Granted, it has taken lots of hard work plus more than a couple of times when I blindly took a risk, only to have that risk pay off in a big way.

But I would have been happy just being Wesley -- the ordinary guy with a beautiful wife and a houseful of kids, which we would have lovingly raised together. Call me old fashioned, but one of my goals was to have the white picket fence surrounding the white-sided two story farm-style house on the big corner lot in a nice, quiet town.

That quiet town could have been the town I was raised in, and that would have been fine by me. I was an only child, born to a husband and wife who were a very small-town traditional couple. They taught me the value of hard work at an early age. I had regular chores and responsibilities beginning at the age of five. Now don't get me wrong -- I was also allowed most of the normal kid-type things, such as playing sports, hanging out with friends, working a part-time job to pay for my first car. I loved my parents very much, and never felt their traditional ways were a burden on my lifestyle.

I met the love of my life, Mandy (really Amanda, but she just seemed more like a 'Mandy' to me) during my junior year in college. We got hooked up together by common friends. I wasn't looking to find a freshman girl with which to start a relationship, but fate intervened, and it didn't take long for us to start looking at potential dates for a wedding. She was an only child like me, raised with very similar values. When I met her parents for the first time, I couldn't believe how much they were like my own. I felt my future with Mandy would be perfect.

We couldn't wait for Mandy to get her degree before we got married. It was a perfect day. There had never been a more beautiful bride than Mandy, and I seriously doubt there will ever be one more beautiful again. It was an ideal wedding, as we started our new life together surrounded by family and close friends. Following a honeymoon, we established our first home.

Well, first apartment, that is. I had taken business finance classes in college, with a specialty certification in financial management. I was fortunate enough to get a ground-floor job in a big brokerage house in a large city just 25 miles from our little small town. All we could afford was a two-bedroom apartment with a tiny kitchen - Mandy didn't know how she was going to be able to cook for me there. We managed, but it really didn't matter. We were so in love that even if we had to live in a hostel, we would have made it work.

I found my job challenging at first, but eventually fell into a good "groove," where the accounts I managed were doing quite well. This put me in line for promotions, increased responsibilities, and better salary. After two years of apartment living, we had saved enough money for our own little three bedroom house. It wasn't in the small town of which I had dreamed, but it was the next best thing.

With our own house now, it was time to begin our family. The mechanics of making a baby were never a problem. There was nothing better in the world than making love to Mandy. We weren't afraid to talk to each other about the things we liked and didn't like. We weren't afraid to try new things with each other, including a little role play from time to time. We each had our limits, and that was fine, because we each understood that our sex life was about love first. As long as we remembered that, everything else would be fine. The connection we had when we made love was more important than the sparks it created inside our bodies.

So when we set out to start our family, we were more than surprised when it didn't happen right away. We chalked it up to bad luck and kept on trying. Finally after more than a year, we were presented with the greatest news -- Mandy was pregnant! I'll never forget the day we were able to hear our little baby's heartbeat inside Mandy's womb for the first time -- I know Mandy was crying, and I'm pretty sure I was too. Our plans were being realized -- we were becoming the family I always envisioned us being!

As Mandy's pregnancy went along, we made changes in our house. We quickly converted one of the bedrooms into a nursery. We purchased all of the furniture it needed -- crib, bassinette, changing table, rocking chair where Mandy could sit to feed the baby -- you name it, we got it. We spared no expense -- well, we purchased what we could, given the fact that there still wasn't a lot of extra money going around, considering the home mortgage and all.

The day came when we would learn the gender of our baby. We had decided we wanted to know before it was born, so the nursery would be the right color when we brought the baby home. So when the sonogram tech told us that she was 100% certain we were having a girl, we were elated. We had been planning names since we first found out about the pregnancy, so as we looked at the monitor on the ultrasound machine, we were looking at our daughter Kaysie Grace. Now that she had a name, we were more anxious than ever to get through the pregnancy and hold our little Kaysie Grace in our arms.

Unfortunately, it was during that sonogram that we also found out that Mandy had some condition that put her in what was known as a "high-risk" pregnancy. I don't even remember the details of it now, but the doctor assured us that the risk was fairly light. Still, as a precaution she told Mandy that she needed complete bedrest until Kaysie was born. It was hard for us to adjust, but we knew in the long run it would be worth it.

The day of her birth was so exciting. I went into the delivery room to be with Mandy while Kaysie was born. When I first heard Kaysie's cries, I cried as well! Our beautiful daughter had finally made her arrival into our lives! I looked at my wife and said "I love you!" She answered back, "I love you, too!" and squeezed my hand.

It turns out that those words were the final thing Mandy would ever say to me. She closed her eyes, and immediately I could tell something was wrong. Against my demands, I was ushered out of the delivery room. For a long time, I couldn't get anyone to answer my questions. I tried to sit down, but I couldn't -- so I paced the hallway outside of the delivery room. I don't know how long it was, but eventually our doctor came out, and by the look in her eyes, I knew she didn't have good news. All she said was, "I'm sorry," and came over to me to give me a hug. My world collapsed in front of my eyes.

Eventually, they brought Kaysie out to me for the first time. She was healthy, beautiful and perfect. I could already see her mother's features in her perfect face. She had a full head of dark hair, and the tiniest little fingers you could imagine, which were now resting around my pinkie finger. I fell madly in love with her, because she was all I had left. I made a vow right on that spot to do all in my power to love her, raise her properly, and provide for her well-being. It was those three goals to which I tied to my lifeline. As long as I had her, I would be okay.

If it weren't for my parents and Mandy's parents, I don't know what I would have done. I thank God every day for their love and support. I could always count on either my mom or Mandy's mom to help me learn how to be a good daddy, and to babysit for me when I was at work. My parents and Mandy's parents became great friends with each other out of their love for me and Kaysie. We spent most holidays together. It was through their selflessness that Kaysie and I turned out as well as we did.

At work, I became driven to be the best financial advisor the world had ever seen. My big break came during a two-year national recession. I had figured out ways to manage my portfolios well enough that while other funds were declining, I managed to at least maintain the baseline amount in my portfolios, and even in a couple of cases showed growth. While other companies were seeing sharp declines in the value of their employees' retirement funds, my companies didn't have to worry about their employees.

The companies whose funds I managed got together and came to me with an offer. They wanted to stake me to my own financial management company. They were willing to sign a five-year contract with me stating that I would be the exclusive manager of their company retirement accounts. They also allowed me to take on other clients, which they believed would happen rather quickly once the deal was made. I was to be the sole owner of the company, and as long as I maintained my record of managing their funds, I could do what I wanted to with the business.

So that's how KC Financial Management was born (KC for my daughter Kaysie, of course -- I wanted that name so I would always remember what had driven me to my success). My stakeholders were right -- if the companies that staked me had been willing to create my own business for me, other businesses figured out right away that I must be good. Within two years, I had 10 advisors working for me, and shortly thereafter, we reach a net profit of $1 million in a year's time. When we made that goal, I gave each of my advisors a $10,000 bonus as a way of rewarding them for their faithfulness and for their part in making my company a success.

As all of this was happening, my dear sweet Kaysie was blossoming into a very beautiful and talented young woman. By the time she was a freshman in high school, she had grown to nearly six feet tall, which given my own 6'3" frame, I shouldn't have been surprised. She used her height to excel in volleyball, and by her senior year in high school, she earned a full scholarship to a Division II school about four hours away from home. Since I could have easily afforded to pay for Kaysie's tuition and living expenses, I decided that I would fund a full-ride scholarship at that same school. That scholarship went to a young girl who had many of the qualities that Kaysie had, but could not have afforded to go to school otherwise. I still fund that scholarship to this day, and through the company, we have expanded to where we are now giving three scholarships each year. I let the spouses of my employees decide who will receive those scholarships. In doing so, they play an important role in the company. That means that in a typical year, there are 12 young women attending college that probably wouldn't have been able to go otherwise.

One of the drawbacks I experienced during this time was incredible loneliness. Kaysie had never spent more than a week away from me, and now she was moving to be four hours away on a full-time basis. I made it a point to go up to visit her as often as possible, but I also knew that as a maturing young woman, she needed her own time to begin to work out her life plans, just as I did when he was her age.

******

Now my beautiful Kaysie was standing before me, ready to be my escort for the evening. I'm not a fashion writer by any means, but I can tell you that she was wearing an extremely clingy silver gown that had streaks of emerald green woven in and running vertically, giving off the image that she was taller than her 6' height. The dress came down just a little short of halfway between her ass and her knees, which perfectly displayed her long, tan legs, highlighted by her supple thighs. Every single sexy, womanly curve was on display, from the swell of her medium sized breasts to the flare of her luscious hips. I hadn't seen the back side yet, but I'm pretty sure the bubble of her perfectly shaped ass would be on full display as well.

She walked slowly over to me on her 3-inch heels. They had straps that were wrapped around her ankle. The straps looked like they were sequined in diamonds, which only added to the shimmer of the dress. In those heels, she was nearly as tall as me, and I was fine with that.

"Baby," I said softly as she approached me, "this may not be appropriate for me to say, but you are so damn sexy. Every man in the place tonight is going to be jealous of me because of the beauty that will be on my arm!"

She blushed, and I wasn't ready for her response. "Daddy, you're making me a little wet just saying things like that!"

"Just you remember - tonight, you are my prized possession. Some of those old drooling farts may try to do anything tonight to get you away from me. Just stay with me, and it won't happen."

She laughed, and said, "Don't worry, daddy -- the only person who can do anything they want to with me tonight is you!"

Her teasing caught me off-guard. I assumed she was just getting into the role she was playing for the night. Surely she didn't really mean that she was making herself available, did she?

"Kaysie, you know that your role tonight is only for the duration of the party. After that, you are back to being Kaysie, my beautiful and charming daughter."

She nodded her head and murmured, "We'll see."

I texted the car service and told them that we were ready to be picked up. As we were heading to the door, Kaysie stopped me and said, "If it's okay with you, tonight I want to be introduced as Grace. That will help me remember to stay in character. Can you handle that? Can you remember to introduce me to your friends as Grace?"

"I'll try to do the best I can. Actually, I like it -- kind of an alter-ego thing going on."

"Good," she said. "One more thing -- Grace is kind of a naughty girl, so she needs to show you something." With that, she hiked up her skirt, until she was showing her shaved pussy, visible because there were no panties to cover it up. "I hope you don't mind -- don't want any panty lines showing underneath this dress!" And with that image now burned into my eyes, she lowered her skirt, turned and patted herself on her ass, and walked on to the door.

It was going to be a long evening, and that could be very good, or very bad!

By the time we got to the ground floor, the car was waiting for us. I was pleased to see that Jeff was driving. He was one of the regulars the company sent to me anytime I called for a car. He was standing on the right side of the car, and as we approached, he opened the back door. Kaysie got in, and as I was preparing to follow her, he leaned down into my ear and said, "You got yourself a winner tonight, Mr. Wesley. She's amazing!"

I smiled back at him and said, "Thanks, Jeff. I always value your opinion. I just hope I can keep all of the lecherous hands off her tonight!"

The car pulled away, as Kaysie sat close to me and leaned her head against my chest. I put my arm around her as a loving father would, or as a loving boyfriend -- I wasn't sure which I was at the time, since we were kind of blurring those lines in her roleplay tonight. I did know one thing -- there would be no more beautiful woman at the party than Kaysie, and I wanted to make our entrance special, so I decided that for one night, we would be the last ones to arrive.

I lowered the privacy glass between the front and back of the car. "Jeff, would you take the scenic route to the club tonight? I don't want to be there before 8:30. While you're driving, we shall enjoy the sights of the city on Christmas Eve."

"Very good, Mr. Wesley. I shall make your drive smooth and festive!" With that, I returned the screen to privacy mode, and turned my attention back to my daughter.

******

To stem the loneliness of living alone with my daughter being off to college, I tried dating, but had little success. There were plenty of fish in the sea, but I was leery that my dates were only interested in my financial status, which was growing all the time. It's probably unfair to think that all of my potential dates viewed me only as a rich, single man, but I didn't have the time or the energy to try and sort out which ones were genuinely interested in me and which ones were only interested in the green I carried in my bank accounts.