My Escort, My Daughter

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 kidding 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 children 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."