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 20th 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 k**s, 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 c***d, 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 k**-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 c***d 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.
It was also about this time that the social requirements of the owner of a growing financial management company increased as well. As we took on larger clients, I found out that they liked to have parties so they can "spread the wealth" socially. At first it was awkward going solo. Most of the parties were fairly lame, so having a guest with you would have helped me to survive.
I also quickly learned that some of the men (and perhaps a woman or two) would attend these parties with a young, gorgeous little creature on their arm. I thought that was a pretty good trick, because usually the type of guys that had the young things with them probably would have had trouble scoring with women their own age, except for the excessive bulge they proudly displayed -- bank account bulge, not male package bulge.
It wasn't too long before I learned all about the escort service. For a fee, you can get a pretty young thing to accompany you just about anywhere at any time. The rules are specific -- no sex is involved, and if you get caught pursuing sex, then you could face a charge of solicitation for sex. I can't think of too many men in my position who would want a charge like that getting around.
Of course, I also learned that the escorts were free to "sweeten the deal." It was done outside of the escort agency (wink wink) so that they would not be responsible for something that went wrong. I honestly don't know if the agency got a cut of the extra deal or not. I just knew that once the price was set, nearly anything was possible.
My first escort was Robin. She was tall, blonde, and athletic, but in a sexy sort of way. I'm pretty sure I was more nervous on our first outing together than she was. Robin was escorting as a means of saving up to pay for the exotic honeymoon she and her fiancé were taking next year. Since she was engaged, it was strictly an escorting arrangement, and I was fine with that. I wasn't really looking for sex, although I certainly wouldn't have turned it down. In fact, some of my masturbatory fantasies were fucking her doggy style with a handful of that sexy blonde mane interwoven through my fingers. But Robin was more important to me as an escort than as a fuck buddy, so I never pursued her in a romantic way. I did, however, attend her wedding after she informed me that she was giving up the escort service, ready to start being a wife. I'm also pretty sure the fees I paid for her services alone would have covered the cost of her island honeymoon.
After Robin stopped, I waited a couple of months before requesting another escort. That's when Rachel came into my life. Rachel quickly became the fourth most important woman in my life, after my daughter, my wife, and my mother. I had requested another blonde, and they set me a short, sassy and spunky 21-year old that nearly turned my life upside down.
We had our first official outing together, and Rachel came back to my apartment and asked me about what she called "scoring the big contract." She was willing to be an escort with benefits, if I was willing to make the payment for services rendered at the level she requested.
I was not prepared to be offered this, quite frankly. Since Robin had been an escort only, I guess I had forgotten that the extra services were potentially available. I think Rachel sensed my surprise and confusion, because she made me an offer I couldn't refuse -- she would demonstrate her skill set right then and there, at no cost, and I could decide if I wanted to continue with the extra services.
Let me tell you, it had been over 27 years since I had fucked a 21-year-old woman, and I guarantee I was in much better shape back then. Rachel worked me over. She demonstrated each of the talents she was willing to share with me, including oral with swallow and fucking in any number of positions, performed with energy and enthusiasm that would have made me give her a score of 10 if I were judging her performance. The only thing she called off-limits was anal, and since I had never done that anyway, that was fine with me.
We came to an agreement on financial compensation and frequency of service. Basically, for the price we settled on, Rachel was my escort exclusively. She agreed to accompany me any time I requested her, regardless of the function. For instance, if I wanted to go and grab a burger with her, that was fine. If I wanted her to escort me to a concert or art gallery opening or other social function, that was fine as well. Her main function would be to accompany me to business events, where she knew I expected her to look hot and sexy dangling at my arm, which was a fairly close representation of how we looked together given the differences in our height, since she was only 5'3" to my 6'3". Her only request was that I gave her at least three days' notice for whenever I requested her services. I could call on shorter notice, and if she was available, she would meet me, but if she had something else planned, I could not expect her to change her plans.
Rachel was a perfect guest at the business parties to which I often attended. She was very confident in her ability to visit with some of the city's top financial planners as if she were on an equal basis with them. She knew she couldn't stack up to their vast financial knowledge. But she also knew that for the most part, they weren't there to talk business. In fact, many guests at these parties refused to mix business with social activities, which was all the better for Rachel. She was one of those rare persons would could find a way to make you happy to be with her, even if you didn't know why.
I know I was elated that she was with me. I don't know why, but with the sometimes pompous crowd of the business world, something as shallow as having an escort on your arm seemed to increase your standing. It became a status symbol, having Rachel with me, clinging to my arm, smiling at the fake friends I smiled at. It was never spoken between us, but she could tell which ones I didn't really like, and would seem extra friendly to those people, as if helping me cover up my disdain for them.
It wasn't long before I started what I guess were feelings for Rachel other than as an escort. I began to look for reasons to call her, even if just to have her over to talk. I remember the first time we met together and didn't have sex -- it was just a great day filled with a little shopping, a little eating, and a lot of just walking and holding hands. She made me feel young (well, except for the times where she wore me out with sex!), something I hadn't felt in many years. We had returned to my apartment and she had started getting undressed, but I stopped her. I didn't need that on that day. I had already gotten what I needed, which was companionship.
I knew it probably wasn't a good thing, especially considering she would never be with someone like me if I weren't paying her a large sum of money for her attention. I was kind of hoping that maybe she had started to develop some feelings for me as well, although deep down I felt that was probably impossible. I then began to wonder if I was just setting myself up for the reality that someday she would be gone, regardless of my feelings. I decided to just enjoy it while I could, even if it meant me pretending she liked me as much as I liked her.
******
The snow had started to fall a little more heavily now, and it was doing a pretty good job of making the city seem a bit more festive on this Christmas Eve. I was enjoying the feeling of having Kaysie leaning against my shoulder as we rode to the party. It seemed as though we didn't have enough time in our busy lives to really spend time together, and even though this was an awkward reason, it was good knowing that for the rest of this evening at least, she would be with me.
We rode in silence for the most part, before Kaysie asked the question that I had been anticipating. "Daddy, tell me about Rachel -- tell me about your relationship with her. I mean, I know she's an escort and all, but is there more between the two of you?"
I sighed, while searching for the answer to that question -- a question I had often asked myself. "I'm not really sure, Kaysie. I know that when I'm with her, she makes me feel special, and I don't know if that's appropriate or not. She is very kind to me, and I enjoy the time we hang out together just as much -- if not more -- than the time where she is fulfilling her duties as an escort. It's odd, I admit it -- after all, I am twice her age. It's really strange having someone special in your life that is the same age as your daughter. Does that bother you?"
"No, not really. If she is giving you happiness in any way, than I'm glad for it. I know how much you sacrificed for me raising me all by yourself. I know that there were times when you put my needs over your own. You never really dated while you were raising me, and I feel bad about that."
I quickly corrected her. "It was my decision to do that, Kaysie, so you shouldn't feel guilty about that at all. You were the only woman in my life, and I couldn't let anybody else interfere with that. Please don't blame yourself for that."
She looked up at me with those big, deep green eyes. "I know, daddy, and I love you so much for it. I'm just glad you have someone now to spend time with, even if she is my age. I can handle that part of it just fine."
She turned in her seat a little and rubbed her hand over my chest. At that moment, she was still my little girl, whom I would give my life for, just to keep her safe. I pulled her closer to me, and gave her a little kiss on her forehead. As strange as the circumstances were, I knew this was one of these moments I would remember forever.
As we rode along, I continued trying to describe my relationship with Rachel. "She is special, but I'm afraid my feelings for her are stronger than her feelings for me. After all, she is paid for what she is doing. She is paid to make it look like she has genuine feelings for me. And she's very good at what she does."
Kaysie raised her head and looked at me again. "I'm not so sure about that, daddy. When we visited earlier, I think I could tell that she had feelings for you as well."
I had forgotten that I had asked Rachel call Kaysie to explain what an escort's duties were at functions such as this one tonight. "Kaysie, she's not paid to have feelings like that. She's paid to make me look good, to please me in whatever way she can. Why do you think there's more than that?"
"I don't know, daddy -- it's just that girls can tell about things like this. It was the way she talked about you, the way she described some of the things she does for you. As we talked, I could detect some real feelings in her words. I think there's more there than you think. I think she has a crush on you!"
I shook my head. "Honey, that can't be. She has a boyfriend -- that's where she is tonight, spending time with him and his family. What she does for me is a job. The feelings she has are reserved for him."
"I don't know, daddy -- I think there's more there than you think!"
******
After another social event for the company, we were back at my apartment. Rachel and I were lying in bed, naked, holding each other after a round of mind-blowing sexual antics. As we snuggled under the covers, I decided I needed to know more about our time together.
"Rachel, if I ask you something, will you be absolutely truthful to me?"
"Of course, Wesley -- what do you need to ask?"
I swallowed, then asked the question I probably should have just ignored. "Do you have any feelings for me, or am I just another client who is paying for your services?"
It was out there now. In that question, I had just expressed my fears, and now I was waiting for an answer I probably didn't want to hear. If the bedroom was quiet before the question, it was deathly silent now.
Rachel separated from me a little bit so she could look straight into my eyes. I could tell she was searching for the right answer, just as I was searching to know it from her.
"Wesley, this is very hard for me, and I don't want it to be hard for you as well. You are an amazing lover. You have reached me in places that have never been touched before. I have never had a man who places my sexual satisfaction above his own -- especially a "client," as you put it. My body tingles every time you call and set up an appointment, because I know at the end of the night, I'm going to feel incredible.
"But this is my job -- it's what I do for a living, and if I let feelings interfere in any way, then I'm not really doing my job very well. My job is to give you pleasure, as an escort at your events, and then back here, between the sheets, or the couch, or wherever you rip my clothes off and attack me! I'm not sure that was the answer you wanted to hear, but I have to be truthful with you. You make me feel like a wanted woman, but at the end of the day, I have to remember that it's just my job."
She scooted back over close to me, and ran her hand over my naked chest. She quietly asked, "Do you hate me now?"
I squeezed her as I said, "No, I will never hate you. You're right -- it's not the answer I wanted to hear, but I knew it was the answer I was going to hear. However it is with us, I know I want it to continue. You make me feel young again, and that's worth more than any money I can pay you."
She reached down and ran her fingers over my sticky cock. "Wesley, I wasn't k**ding about the amazing lover part. If wanting to ride your cock each and every day means I have feelings for you, then yes, I have major feelings for you!"
Her actions and her words had started bringing my cock back to life. As I thought about what she said to me, I realized that things could be much worse. As much as I realized I wanted a serious relationship in my life, Rachel was providing everything else. She pulled back the covers and hovered over me to impale herself on my now rigid cock, and I realized that the line between love and lust was so narrow that for now, I could live with whichever side of the line we fell.
******
The sound of a soft buzzer interrupted the stillness of our ride. I reached over and put the privacy window down a few inches. "Yes, Jeff?"
The driver looked back at us through the rear view window. "I just wanted to let you know that we are about five minutes away from your destination."
"Thank you, Jeff." I put the window back up, and looked over at Kaysie, who was looking at me with inquisitive eyes. "It's a common courtesy. Jeff knows that sometimes the couple in the back is being...well, being frisky with each other, and so he gives us five minutes to get things back in order -- you know, like fixing makeup, or putting clothes back on, that kind of stuff."
Kaysie playfully punched my arm. "That's kind of kinky, daddy! Have you ever needed the five minute warning before?"
"Why Kaysie, my dear -- a gentleman never admits to those kind of things!"
The car began to pull over, meaning we had arrived at the club. It was a nondescript building on the outside. If you didn't know, you would have never expected what it was like on the inside. But the building had been designed that way. It was a place where the city elite could go and hang out with each other, yet the public would never have any idea what was going on behind its doors.
Jeff had exited the vehicle, and was now opening the back door. I glanced at Kaysie and asked, "Are you ready for this?" She nodded back at me and said, "I think so. Just stay with me, and I will do all I can to make you happy." As she said this, she gave me a kiss -- not on the cheek like a daughter, but on the lips, like an escort. My heart leaped as I felt her soft lips on mine. It was going to be an interesting evening indeed!
******
I was so pleased when Kaysie had decided to major in business management. We had talked about her future often while she was still in high school. I didn't want her to think she needed to focus on business just to make me happy. She assured me that even though she didn't know all about my company, she enjoyed knowing that I was good at what I did, and she wanted that for herself as well. I had helped her with the few business classes that were available to her at her high school. The time we spent together was very special for both her and me.
She had done well in college. Her volleyball career had taken off, and she had earned several awards for her play. But more important to me was her success in academics. She had always been a good student, but every parent fears that when their c***dren experience the independence college offers them for the first time, the "fun" aspect of college life sometimes affects the "work" aspect. Kaysie had proven to me that my fears were ungrounded. Her grades in college were stellar, and her passion for her academic work met or exceeded her passion for her volleyball.
She also let me know that she was handling the social aspects of college life as well. She shared with me whenever she had a boyfriend, and even called me on the night she officially became a woman. I cringed at the news, hearing that a boy had stuck his dick in my daughter. At the same time, I loved that our relationship was so strong that she felt like she could tell me. I doubt many fathers and daughters would share that information with each other so willingly.
She had breezed through her first three years of college with no problems. As she entered her senior year, we looked over the coursework she was required to take. She only had three classes, but one of them was a big one -- in fact, it was a full year class. Her requirement for the class was to create a business start-up from conception to implementation. She had to research what kind of business would be successful, find a location to plant it, and demonstrate all the work required to get it off the ground. She didn't actually have to start the business, but her work had to be such that if she desired to start it, all would be ready.
The only problem with most college business programs is that they are often taught by someone who had never operated a business themselves. They know all about the theory of planning and opening a business, but had never actually done it. I could tell Kaysie was worried about going into this class, knowing that her success or failure in the class likely meant her success or failure in her degree.
Kaysie asked me for help in the class, and I readily agreed. We wouldn't have a lot of time to spend together, since there was still the four-hour gap between her at college and me at home. But I spent many weekends with her at her apartment near the campus, working hard on her project in the role of advisor. I didn't do the work for Kaysie, but I answered any question she had regarding the business aspects of it. Together we studied business locations, the capital needed to start a boutique like the one she was planning, advertising possibilities, fixed and fluctuating expenses -- all of the things she needed to address in her project.
For her birthday that March, I had chartered a helicopter to take me down to spend the evening with her, since it was on a Wednesday, and the four hours on the road wouldn't have allowed me any time to spend with her. I had taken her to a fancy restaurant to make her feel special. After we had eaten, we went back to her apartment where I gave her a necklace and matching earrings, as well as a couple of other little trinkets that I hoped made her feel special.
But for her big gift, I handed her a 9x12 envelope. She opened it to find a certificate that said, "I, Wesley Wilson Whitford (so my parents had a thing with the letter "W"), do hereby agree to provide the financial capital necessary to allow Kaysie Grace Whitford to actually open the boutique as outlined in her college business management class project. I also agree that this capital is a gift which does not require repayment, and that Kaysie Grace Whitford shall have 100% management rights to said boutique without any outside interference from me."
I watched with pride as she read it. Her facial expression immediately changed -- first her eyes opened really wide, then she opened her mouth and covered it with her hand. Finally she looked up at me and said, "Is this for real? Are you really going to stake me to let me open up the boutique?"
I nearly had tears in my eyes as I said, "Yes, Kaysie. I'm so very proud of the work you have done preparing this assignment. I can see that you have put everything you have into it, and all of the framework has been put in place for you to be successful. The least I can do is help you make your dream into a reality. That's been my entire purpose as a parent -- preparing you to be able to reach your dreams. If you really want to open your boutique, I want to help make that possible."
With that, she started crying, and rushed over to me to give me a big hug. "Oh daddy, I love you so much! I can't believe you are willing to do this for me! Thank you, daddy -- thank you!"
I choked back the tears as I whispered, "I love you, too, baby! I know you're going to be a great business woman. I'm so proud of you!"
We hugged for what seemed like hours. Finally she backed away and looked at me, and I reached up to brush the tears off her cheek. She said, "I promise to work so hard so I can pay you back, daddy. I want you to be so proud of me!"
"This isn't a loan, Kaysie -- it's a gift. And don't worry -- I already am proud. You are the best daughter in the whole world!"
I didn't want the night to end, but I knew that tomorrow was coming, so we parted and I flew back home. I spent the next day reliving the emotions of the evening before. I knew she was going to do well, and I was glad she had accepted my offer as her birthday gift.
She spent the last two months of class making sure her project was complete, going above and beyond the requirements of the professor. Knowing that her boutique was going to be a reality, she poured her heart and soul into its business plan. It was the most complete plan I had ever seen, and I felt that she couldn't help but be successful once the plan was realized in real life.
Her hard work paid off. Kaysie got an A+ on her project. Her professor wrote that it was the most complete and thorough project he had ever seen in the 20 years he had been making that assignment. Kaysie called me with the news, and I could hear the pride in her voice as she told me. My chest swelled with pride as well. It was an amazing day!
At her graduation ceremony, her professor came over to talk to Kaysie and me. He took the time to tell me how impressed he was with her work. He also confessed to me to being a little nervous, knowing that I was a successful businessman in my own right. I thanked him for his part in her development, and during our conversation, he asked me if I would serve on the business department advisory board, with the possibility of coming and being a guest lecturer. I graciously accepted, and Kaysie beamed, knowing she was the main reason all of this was being established.
The very next day, she set out to find the perfect location for her boutique. She had already decided she wanted to be back in our city. We had survived the whole 4-hours-apart hitch in our relationship during her college years, but it had been difficult. I knew that her life would be extremely busy while she tried to get her boutique opened, and I knew my crazy schedule as well, but being in the same city together would at least offer us more opportunities to spend time with each other. In fact, we established a pact that at the least, we would have lunch together every Sunday. That way, not a week would go by without seeing each other.
She found what we both believed was a perfect location, and by October following her graduation, Grace Boutique was up and running. She endured a couple of tough years following her opening, but I was proud of her with the way she didn't get discouraged, and that she put her entire self into making it successful. The Christmas season of her second year was the real turning point. She had started getting the necessary "word-of-mouth" advertising from satisfied customers, and it made all the difference in the world. With timely advertising and a constant attention to keeping her inventory fresh and desirable at all times, her business took off. Her proudest day was when the local City Times featured her as one of the top 10 up-and-coming new young business women in the city. The copy of the photo that accompanied that article still hangs in my office to this day.
Her thoughts now are of expansion, which will be best solved by opening another location. She told me she wants to do this on her own, and I'm going to honor that. However, as a loving and proud father, I am always ready to step in and provide whatever she needs in order for her to remain successful. After all, that was my goal for her as I lovingly raised her.
******
I got out of the car first, and then extended my arm for her to hold onto as she climbed out. She pulled the hem of her skirt down and adjusted it to make sure it was straight. Together, we walked into the club. As plain as the building was in front, the opulence that awaited us inside was simply stunning.
We stopped first and checked our coats, the proceeded down a long hallway into the lavishly-decorated great room of the club. As we stepped through the doors, all eyes turned to us -- first to me, to see who was arriving, and then to Kaysie -- or I guess Grace now, since we were in the club and she was now my escort. I could tell that by waiting so late to arrive, the audience that watched us enter the building was a large as it could have possibly been.
I immediately spotted a couple of friends across the room, so we headed over to where they were standing, knowing that the eyes that were staring at Kaysie/Grace when we entered had not drifted as we walked across the room. I knew they were admiring her long legs as she gracefully walked with me, clinging to my arm with every step. I knew they were glancing as the swell of her ass, so tightly packed beneath the shiny silver and emerald green dress she was wearing. I knew they were mesmerized by the depth of the dark green of her eyes, highlighted by the length of her lashes and the flare of her makeup. I knew she had hooked them, and was dragging them along for the ride.
But she knew none of this. Instead, she felt self-conscious about the way the people staring at her. She whispered in my ear, "Daddy, why are all these people staring at me? Is there something wrong with my dress?"
I chuckled back at her as I whispered, "No, baby. They are staring at you because you are the most beautiful girl in the world!" She squeezed my arm and gave me a quick kiss on my cheek. I was showing off my prize to the world, and she was showing off back for me.
We spent the evening mingling. I introduced her to some of the most prestigious power players in our city. I was so proud of the way she carried on conversations with these people. She showed no intimidation whatsoever, and the depth of her knowledge in business surprised all of them. That, plus the fact that she was absolutely fucking gorgeous, meant that she didn't have to spend one single second of the evening alone.
About 30 minutes in, I asked her how she was doing. She smiled and said, "Pretty good. I'm still not used to all of this attention. Have you ever felt like a piece of meet at a barbeque convention, and all of the cooks are staring at you, thinking what they could do to you if they only had a chance with you? That's what I'm feeling like right now."
"So I take it you want to stay close to me? You can go off and mingle, if you want, but you have to realize that the farther away from me you get, the more likely you are to get groped by one of the old farts in the room."
She clutched me tighter, and said, "That's okay, Wesley -- I think I'll stay close to you." She smiled at me and winked as she called me by my first name. I knew what she was doing -- if she was Grace for the night, then she was playing the escort angle to the fullest. Plus, it probably wouldn't have been a good thing for people to overhear her calling me "daddy" too many times, although I'm sure some of these old guys who arrive with escorts probably play the daddy game with them after the party is over.
At 10:00, we heard a bell ring. Oh, shit -- I had forgotten about the "tradition" that was coming. It was time for the mistletoe kiss. Lewis Chandler III and his lovely (read sarcasm) wife Patricia were calling us to attention. It was them that were throwing this party. Lewis would make a toast to all of his honored guests thanking us for their support throughout the year, followed by the distribution of "gifts," which were bonuses in varying amounts. The rule was that you couldn't open the bonus envelope to find out how much bonus you received until after the party was over.
Lewis Chandler was in his mid-60's, I would guess. He was heavy set, balding and generally looked unkempt. Some people just weren't born to wear a suit, and Lewis was one of those people, despite the fact that he wore only custom tailored clothing. He was also loud -- he talked too loud, laughed too loud -- hell, he probably even breathed too loud, if I allowed myself to get close enough to him to listen. He was the kind of rich person most people hated, and that was because he didn't do a damn thing to earn the money he now held. It was the hard work of his grandfather and father that built the banking empire upon which he now sat. But, I had control over a pretty sizable investment in which he had entrusted my company, which explains my presence at his party.
His wife Patricia wasn't as annoying as he was, but she was no catch either. Rumor had it that when she was younger, she was quite a knock-out. Another rumor had it that she had married Lewis not for his brains or for his looks, but for his money. She was probably a couple of years younger than he was, and was also heavy-set. She liked to wear expensive clothing with more expensive jewelry, and also liked to talk and laugh loud.
Since it was their party, and since we all appreciated the professional relationship we all had with him, Lewis ended his toast with the traditional "mistletoe lines." Standing underneath a fake version of the kissing vine, each person in attendance had to receive a kiss and a hug from Lewis and Patricia. Fortunately we were to kiss the one who wasn't our gender. But I had forgotten to tell Kaysie/Grace about this part, and as the lines were forming, I could see the look of concern in her eyes.
I figured I had better warn her about what was happening. "Grace, I forgot to tell you this part. Lewis Chandler expects you to kiss him underneath the mistletoe. And it's not going to be just any kiss -- he's going to try to stick his tongue in your mouth while he gropes at least your ass, and probably your breast as well. I'm going to get the same treatment from Patricia, and I'm not going to like it. But it's a good move for the company. If you don't want to do it, tell me now, and I will keep it from happening."
Kaysie/Grace sighed, and said, "Well, it certainly looks unappealing, but I'm sure it will help the company, right?"
I nodded, and she continued. "Tell you what -- I will let him kiss and grope me, but only if when the evening is over, you kiss and grope me the same way he does." She was smiling as she looked at me and waited for my answer.
Her request made me pause. I knew that Lewis Chandler was going to try to get away with as much as possible with Kaysie/Grace -- probably more than a father and daughter should be sharing with each other! At the same time, this would be good for the business, and other than being her father, why wouldn't I want to kiss and grope Kaysie/Grace?
So I looked back at her (which caused my heart to skip a beat) and said, "Sure, why not? You deserve a reward if you pull this off!" She squealed into my ear and grabbed my arm even harder than before, which I took as a gesture of thanks for what was coming once the evening was over.
Finally, it was our turn in line. It was always ladies first, so I stepped up to Patricia Chandler and said, "Merry Christmas" as I bent over to her waiting lips. The kiss was just as squeamish this year as it had been in the past, and she even slid her hand down my back to run it over my ass for a few seconds before the kiss was over. Pulling away, I heard her say, "Merry Christmas to you as well, Wesley, and thank you for my kiss!"
My service at the Chandler torture festival was over, and I stepped back to watch as Kaysie/Grace stepped up for her turn. She was a couple of inches taller than Lewis, which I figured might be a new treat for him. She bent down and he locked lips with hers, while at the same time his right hand found her breast and his left hand cupped her ass. Kaysie/Grace was kissing away, and poor Lewis had to take a step back to maintain his balance. She broke the kiss, and then planted another on the old fart, while cupping HIS ass at the same time! As disgusting as it was thinking that she was having to do this, I started getting aroused watching her flail away on him, and then I remembered I had that very same kiss awaiting me after the party was over!
Kaysie/Grace finally concluded the kiss, and walked over to me smiling, as if to let me know she had done her part for the company as well. The room was extremely hushed watching her kiss Lewis, and as she walked away, they could hear him whisper, "Merry Christmas." He was obviously out of breath after receiving probably the best kiss of his life!
She grabbed my arm and led me away from the kissing area. I asked her if she was ok, and all she said was, "When can we go?"
I said, "Soon -- people will start leaving in a few minutes. Do you need to leave sooner than that?"
"No, I'm okay. The kissing was fine. I figured I could lessen the creepiness of it if I took the role as the aggressor. I think it worked! I just want to get out of here now because you have a deal to pay off, and I'm already looking forward to it!"
She wanted me to kiss her! "Kaysie, I..." but she stopped me short by placing her finger vertically across my lips.
"Listen to me," she said tersely. "Grace just did something pretty special for the company back there, and you owe her back. She is now ready to leave and collect her payment!" And with that, she reached down between us and cupped my cock through my pants, causing it to leap, and my heart to skip a beat.
I sent a text message to Jeff, telling him that we were ready to leave. I went to say goodbye to a couple of my friends, both of whom congratulated me on my date for the evening. When Kaysie/Grace heard them, she blushed and snuggled up even closer to me. I was on cloud nine, yet still thinking about where the remainder of the evening was going to lead.
We picked up our coats and headed outside, where Jeff was waiting to open the door for us. Kaysie climbed in first, and I quickly followed. Even though the car was warm inside, we were still a little bit chilly, so Kaysie sat on my lap and hugged me for warmth, although my cock saw her move as being for another reason, and started to make its presence known. When Kaysie felt this, she looked at me and grinned. This was not now I wanted the trip to begin! I patted her lovely ass, and she sat back down on the seat next to me.
The ride back home was uneventful, unless you count the two times when Kaysie "accidently" rubbed my crotch. Have you ever felt both anticipation and dread at the same time when thinking about a potential event happening? If she wasn't my daughter, my hands would be all over Kaysie on the ride home. I remembered that she had shown me her naked pussy right before we left, something I had forgotten about until this moment. If it was Rachel next to me now, my fingers would be so far lodged deep within her pussy that she couldn't help but scream out in ecstasy. Kaysie is even more beautiful than Rachel, more sexy, and just as exposed. What was stopping me from fingering her?
You know what is stopping you, you idiot -- she's your daughter! It's not right, especially taking advantage of her after she's been the object of sexual desire all evening long! Guys have been drooling over her -- some of the women as well! I bet Patricia Chandler would love to stick her tongue in my daughter's pussy -- it would be more action than she's getting from Lewis! If Kaysie is still swimming in the lust that was directed to her in that room tonight, she might be vulnerable and not able to fend off a level-headed sexual advance from me.
Then another thought occurred to me. With Rachel, I get sex. With Kaysie, I could get sex, if she were as willing as it seems she is. But Rachel admitted to me that there would be no emotional component. As a professional, she is paid to give me pleasure, but no more. With Kaysie, the emotional component is already built in -- just as it has been for the 25 years of her life. I love her more than anything else in the world. So the question then becomes -- would adding the sexual component with Kaysie cause problems for our emotional component?
I looked down at her, her head resting again on my shoulder, and I gave her a little kiss on her forehead. At the same time, I reached my hand around just a little, enough to touch the side of her left breast. I was curious to see how she would react, and it doesn't take long to find out. She looked up at me and smiled, as she took my hand and pulled it around even farther, then placed it directly on the top of her breast. I guess we now know the decision will be mine as to where this goes.
We arrived at my apartment building, and Jeff came around and opened the door. I got out first, then helped her out and guided her in the direction of the door. Before we could go in, I turned to Jeff.
"Thanks, Jeff, for driving us on Christmas Eve. Sorry to take you away from your family."
"That's ok, Mr. Wesley. It's always a pleasure to drive for you. I hope you and your lady friend have a merry Christmas!"
I reached in my pocket and pulled our five C-notes and pressed them in his hand. He looked down at them, then back at me. "I can't take these, Mr. Wesley!
I cut him off and pulled my hand away, leaving the cash in his. "Jeff, buy you and your family something nice for the holiday. Merry Christmas, my friend!
"Merry Christmas to you as well, Mr. Wesley!" With that, he literally hopped around to the driver's door of the car and climbed in, and then drove away in a rush.
Kaysie was smiling at me when I got to the door of the building. "You know, you're the most kind hearted man I have ever known. I'm not just saying that because I'm your daughter. You really care about people, don't you!"
I looked at her and smiled. "It's a business lesson for you, my beautiful daughter. Always take care of the people who take care of you. Keep them happy, and they'll be there for you for a long, long time."
We rode the elevator to the top floor. I looked down at her long, sexy legs and noticed that the right one was twitching. I looked up at her, and she was just staring at me with this huge smile on her face. It was almost like she had spotted her prey, and couldn't wait for the attack.
I soon found out just how true my assessment was. Once the door of the apartment was closed, she attacked me with a sexual ferocity I hadn't previously experienced. She ran to me and jumped into my arms, wrapping her legs around my waist, which bunched her short skirt up and over her naked ass. She had one hand on the back of my head, and the other wrapped around my back. She pulled me to her lips and kissed me like a woman possessed, her tongue chasing mine all the way to the back of my throat.
It was hot, and it was passionate, but it was my daughter, and I still hadn't been able to convince myself that this was the right thing. I grabbed her hair and gently pulled her mouth away from mine, which slowed her kisses down, but didn't quite stop them. In between kisses, I tried to cry out, "Kaysie......stop for a minute.......sweetheart.......wait a little bit....."
She stopped for a little bit, and looked into my soul with her dark green eyes. "What, daddy? Am I doing something wrong?"
"No, baby, it's just that I think maybe we should talk about this. We are creating an entirely new relationship here, and I don't want to do anything to mess up the one we already have. I love being your daddy. Can you handle adding lover to that title?"
"Okay, daddy -- you want talk? Then listen to me talk for a little bit. I have always known that you love me. You have been the best daddy ever! You have always taken care of me, taught me, showed me experiences that have allowed me to become the person I am today. You have been the perfect dad, and I'll never be able to show you how much I love you for that.
"But you've kind of messed me up a little bit too. I've been searching for a man just like you that I could fall in love with -- someone that can treat me just like you have all my life. I've looked and looked, and I don't think that man is out there.
"Then you asked me to be your escort tonight, and you dressed me up in this sexy dress and paraded me around the snobby people of that party. I know all of them were looking at me and telling me how pretty I was. I know all of those men would have given anything to fuck me tonight -- even old man Chandler got hard as I was kissing him, because I could feel him pressing against my thigh. If he knew I didn't have panties on, I think he would have creamed in his suit right in front of everyone!
"All those men wanted to fuck me, daddy, but there was only one man there tonight that was going to get to experience that, and that man was you. Tonight, I realized that there is only one thing you could do to love me even more than you already do, and that was to be my lover. You have given up a good part of your life for me, daddy. Tonight, I'm giving myself up to you to show you how much I love you.
"Think about it -- it's just you and I left. My grandparents have all passed away, and we have no other relation living. We are the only ones who will be affected if we fuck each other. You know how badly I want to fuck you, and I think you feel the same way. It's time, tonight, right here."
Then she unwrapped her legs from around my waist and stood on her own two feet. She readjusted her skirt, pulling back down over her ass, covering her pussy once again. She looked at me once more with those soul-piercing emerald eyes, and with a shy smile, said, "If I were Rachel, you'd already be fucking me. If you are having trouble with the idea of fucking Kaysie, then why don't you fuck Grace? After all, she was your escort for the night!"
She turned around, with her back facing me, and said, "Wesley, would you help me pull my zipper down? I just can't quite reach it myself."
I walked over to her and grabbed the zipper tab and started pulling it down slowly. If Grace wanted to be fucked, I think I could handle that!
The zipper stopped right above the crack of her ass. She turned back around and shrugged her shoulders, which caused her dress to fall to the ground at her feet. For the first time, I was staring at my beautiful daughter, naked except for her heels. She was incredible! Medium sized breasts with upturned nipples standing firm and erect, pointing up to the ceiling. Her stomach was long and taut -- no fat appearing at all. As she had shown me now a couple of times, her pussy was shaved clean, and even from where I was standing, I could see the moisture that had built up from being aroused all night by the sexual tension that had surrounded her.
"Turn around." When she did, I saw the roundness of her perfect ass. She was so athletic and muscular that her hips were concave, as if to create a place to put my hands while I was fucking her from behind. The air was filled with two kinds of perfume -- the kind she put on before the evening started, and the kind that only an aroused pussy emits as it spills its moisture in preparation for fucking.
"Undress me."
Still in her heels, she stepped over her dress, now lying pooled on the ground. She took off my tie first, and then started with the buttons on my shirt. With each one, the sexual tension inside of me increa