Driving Jackie Ch. 01

I could appreciate her concerns; however, since my clients normally took care of my expenses, I had not even given a thought to her situation. I remember being in that position early in my professional career, and could relate. "Don't worry about it. The rooms are really big and you don't look like you take up much space."

Jackie giggled again and asked, "Are you sure. I don't want to impose."

"You are not imposing, I don't mind at all. As I said, it will be a nice change to have someone along to talk to."

As I was speaking, I got an idea, but did not want to do anything that might hurt her feelings, so chose my words carefully. "You know, if money is tight, I can take care of your ticket..."

Jackie blurted out, "You can't pay for my ticket. I've got it covered."

I really did not want to embarrass her or make her feel inadequate, but continued slowly, "Hold on a second. I know you are capable of paying your own way, but I have an idea. While I wouldn't mind picking up the cost of your plane ticket, just as I would do for any other friend, I don't actually have to pay for anything. You know I travel a lot, and between the air fare, hotel, rental car, various promotions and bonus programs, I literally have a million frequent flyer miles. I rarely go anywhere a client is not paying my expenses, so the only time I use them is to upgrade my seat to first class if the flight is more than a couple of hours long. Nothing out of pocket and I will not have to use too many to get a ticket to Kansas City."

"You can do that?"

I continued, "I am a business traveler, and often do not know far enough in advance when I will fly, so never get the discounted tickets. The airlines love this kind of traveler since we pay full fare and do not give them any trouble. I am a member of the VIP club in all major airlines, and they bend over backwards to make me happy. I can make a call tomorrow and everything will be set. You will have a little extra money to spend in KC, and I will finally get some benefit from all this traveling." I hope my explanation was sufficient and she did not think I felt her a charity case.

She asked again, "Are you sure you can do this?" Besides the anxiety I saw on her face, I think I detected a glimmer of relief in her eyes as I again assured her it was no problem and something that was done all the time.

Jackie thanked me in a quiet voice, and was silent for a while. To try to get things more normal, I told her she could pick up dinner (greasy burgers stale fries and all) as a way to thank me. She smiled at the suggestion and joked that if I was this easy, she should have asked me for favors long ago. I was glad to see that she appeared to be back to her normal happy mood.

I called later that evening and made all the necessary arrangements. The flight was booked in coach, but there were still seats available in first class. I upgraded my own and reserved a second for Jackie. Everything was set and we would take an early commuter flight to Atlanta, then the regular run to Kansas City. Picking up an hour during the flight, we should be in before lunch on Monday.

*****

Bright and early on Monday morning, Jackie pulled into my driveway as I had asked, then we put her car into the garage for the week. I don't like leaving my own car in long term parking, so usually just called a cab to take me to the airport. Knowing women have the reputation for over packing, I was happy to see that Jackie had a nice, manageable suitcase so we would not be loaded down with excess luggage. I had my laptop in addition to my own case and a garment bag to hold the suits I needed to wear when I visited a client. I usually lost the coat and tie within 10 minutes of getting in the door, but initial appearances are important, so I had to make the effort. Jackie was wearing a sleeveless flower print blouse and a light green skirt, very fashionable and it looked comfortable for traveling. We got to the airport in plenty of time, checked in without problem, and soon were sitting on the little commuter plane. As we took off, Jackie looked a little nervous, but once in the air, she seemed more comfortable. I guess she had never flown on a small plane and the experience was new to her. We made the transfer in Atlanta, and were checking into the hotel in downtown Kansas City just before 11:30.

We took our bags up to the room and decided to have a quick lunch in the hotel restaurant. I had called my contact when we arrived, and expected to get to the client's site about 1. My plan was to meet with the staff I would be helping to get the application installed to work out any issues we might face tomorrow. I would be doing the install first thing tomorrow morning, and then the rest of the day would be testing. We would do data migration overnight, then more testing on Wednesday. I would also be tutoring the support staff that afternoon, and the new application would go live on Thursday morning. I would spend the rest of the day keeping tabs on things in case of problems, but didn't expect any. Friday was set aside in case things got crazy, but I expected to be flying home around noon.

I had a quick BLT in the restaurant while Jackie worked on a chicken Caesar salad. I asked what she would be doing for the afternoon, and her plan was to just take a walking tour of the immediate area. She was a little uncertain about being in a strange city, but the hotel was in a better part of town, mostly shopping, hotels and office buildings. I told her to have a good time, and I would probably be back around dinner time. I promised to take her to a good steakhouse, Kansas City is well known for good steaks. She was still finishing up her meal when I left to find the client's address.

The afternoon went well, and time passed quickly. I would be working with a team of 5 IT staff, all of whom seemed competent and capable. We did not foresee any issues that would become problematic, so set 9 AM tomorrow as our next meeting time, and I was back in the hotel room just after 5. Jackie was not there, so I got a beer from the mini bar and checked my phone for messages. None from Jackie, but I did need to return a few calls from other people who wanted to speak with me. Jackie got in about 5:30 and although she looked a little tired, seemed to have had a good time and greeted me with a big smile. She sat down to rest for a few minutes and I offered to get her a beer or some other beverage from the bar, but she declined, preferring to wait for dinner.

I had checked with the desk when I got back from my afternoon meeting, and found one of the city's better steakhouses was just 3 blocks over from the hotel. The clerk told me that I would have no problem getting a table on Monday night, so reservations would not be necessary. I asked Jackie if she was up to walking the 3 blocks, or if she wanted to get a cab.

"A cab for a three block ride? Are you nuts? Let's get going, I can taste those steaks already!"

We started to walk and the heat of the day was diminishing, but the temperature was still warm enough not to be unpleasant. The crowds on the street had lessened as well, and I saw the restaurant up ahead in the next block. About half a block away, I started to smell the odor of grilling meat, and my mouth was salivating before we got there. I think Jackie was having the same issues with the smell of the steaks, her pace had unconsciously quickened as we got nearer the door. Inside, the hostess seated us right away, finding a table that was a little out of the way, but not too far from the center of the dining room. There were a number of other patrons, and the aroma of steak was amazing. The waiter came by and gave us menus, each only a single page. The restaurant specialized in beef and aside from 1 chicken dish and a couple of seafood entrees, there were a dozen beef choices. I guess people did not come here to have anything but red meat.

The waiter asked if we would like anything from the bar, and although I gave a quick thought to another beer, I decided to wait for the meal. Jackie decided to think about what she might want, so he left us to peruse the menu and make our choice. I was looking at my menu when I heard a quick intake of breath from Jackie, and when I looked at her, her face seemed a little pale. I assume she had seen the prices on the menu and was not expecting something that expensive. The prices were on the high side, but not out of line with a first class restaurant. I did not want her to think she had to order a salad just to keep the cost down, but still did not want to embarrass her by making her choose a lesser meal just because her funds were more limited than my own.

"Kind of pricey, huh?"

""O my God! How can they get away with charging these prices? How can anyone afford to eat here?"

I did not want to make her feel bad, there were no restaurants at home anywhere near this fancy or pricey.

"Don't worry about the prices. I said I would take you to dinner tonight, and I will take care of the bill. It's not that big of a deal."

"I can't let you pay for me all the time. I didn't ask to come along expecting you to cover all the costs." Jackie blurted out.

I really did not want to upset her, but at the same time, I knew her financial situation was not such that she could afford to spend this kind of money on dinner, even if it might only be very rarely.

"Jackie, it is not that big a deal. I know the prices are high, but I want you to enjoy the meal, not worry about paying. I understand you can pay your own way, and if you really want to, I won't stop you. I did, however, invite you to the restaurant, and I picked it out without consulting you. I admit I did not know just how expensive it would be, but I can expense the cost. It won't cost me anything out of pocket and my client will pick up my expenses."

Her eyes got big and she asked, "They will pay for this kind of meal? They don't care if you eat out at fancy restaurants all the time?"

Well, I'm sure they would prefer me to eat at Taco bell or some other similar place, but mostly they just look at the bottom line when I submit my expenses. If the expense report I submit falls within their expected range, usually they don't worry about individual items. Once in a while I run across some anal bean counter who complains about this or that, but if the expense is disallowed, I have enough profit built into my charge that I can deal with it."

Still unsure, Jackie asked more questions. "How can you keep the total within their limits if you go to dinners like this? I can't imagine their approved range is that high?"

"Well, actually, they do expect some padding, but there are ways around it. I don't usually buy breakfast; I can always get coffee at the client's site. The IT staff practically mainlines caffeine and someone always has donuts or bagels around for the staff. For lunch, it is pretty easy to find a friendly manager to take me out and have the bill put on his expense account. That way, one expensive dinner is roughly equivalent to an average dinner along with a normal breakfast and lunch. It's all a game, and everyone does it. Companies expect things like that, and if I don't try to take advantage, normally they pay without question. Just relax, enjoy the meal and forget you saw the prices."

Jackie smiled again, although it was still a little hesitant. I could also see some relief in her eyes. I hoped my explanation had put her mind at ease, but I knew she felt somewhat indebted to me. I really did not want her to feel this way, but hopefully we could get over that with a nice dinner.

We had finished our salads just as the main course arrived. The conversation had returned to normal, Jackie had taken my advice and forgotten about the cost of the meal. I had eaten at quite a few good steakhouses in my career, and this was one of the better ones. I know Jackie enjoyed her meal as well, she would not stop saying how good the food was. We had decided to pass on beer or any other liquor, instead choosing to share a bottle of wine. We each had 2 glasses with the meal, so spread out over the 2 hours we sat there, the effect of the alcohol was minimal. We both got into the spirit of being out for the evening, forgetting about business (for me) the next day. Jackie did not have any specific plans for tomorrow, but she did say she had a few ideas. We finished and walked back to the hotel arm in arm, laughing and talking almost as if we had been on a date. I was glad she was along with me for this trip, it was much more enjoyable than my normal road experiences.

When we got back to the room, Jackie kicked off her shoes and turned the TV on, saying she wanted to catch the weather forecast to see what effect it might have on her plans for tomorrow. I got my laptop out to check my email and go over the next days work one last time. When I looked up as the computer was booting, I saw Jackie unbutton her blouse, then remove it, followed soon after by the filmy green bra she had underneath. The skirt came off next, and as she noticed me watching, she said she was just getting more comfortable. Here she was clad only in her panties, just as she had been earlier in my garage. She also looked just as good tonight as she had then.

I finished my task and the local weather reader promised warm and sunny for tomorrow, so it was time for bed. I stripped down to my boxers and we each climbed into the large king sized bed. I turned out the light, and except for a slight phosphor from the TV screen that was quickly fading, there was not a hint of light anywhere. The heavy drapes did their job, insulating us from both light and sound. I did not even hear the normal far off sounds one usually notices in hotels. The silence was a change from the hustle and bustle of the day, and I was starting to relax. As I lay there, Jackie slid over and put her arm across my chest, then her leg across my upper thighs.

"You don't have to do this, Jackie." I said as I felt a tongue in my ear.

"I know." "I don't expect anything in return for letting you stay here with me.", I continued, even as I withdrew my arm from between us, put it around her shoulders and pulled her closer to me.

"This isn't any kind of payback. I had such a good time this evening, both at dinner and during the walk back, I really don't want the good feeling to end just yet."

Her words pretty much echoed my own thoughts, I just did not want to seem like I was taking advantage of her or that I expected something from her in return for what I had done so far.

I turned my head to speak again, but her lips and tongue found my own lips, and she was kissing me, preventing me from saying anything else. Her tongue was looking for a way into my own mouth, and who am I to deny it entrance. Our tongues moved together, getting to know one another, as we each experienced the feel of the other's lips. I could still taste the faint traces of the evening's meal, and her increasing passion made that taste more enjoyable. I pulled her closer to me, hugging her tightly with my arms around her waist as she was moving her leg up and down over my crotch. This had the normal effect, and I was noticing an increasing pressure within my boxers.

I suppose at this point I should mention just how well I am equipped, but to tell the truth, I have never taken a yardstick to it. OK, so maybe I will never be mistaken for John Holmes in the locker room; I have what I have, it is what my parents gave me before I was born, it has never let me down and I have never had any complaints. Judging by the way things were going, I don't think it was going to let me down here either.

I pulled Jackie up onto me, lying directly underneath her warm body. I could feel her hard nipples at full attention, and not a cold beer bottle in sight. She started rubbing her pelvis across my crotch, making small groaning sounds with each push. By now my cock had grown to its full size, and each time she rubbed down its length, I felt a wave of pleasure go through my body. I am pretty sure Jackie was enjoying the feeling as well, besides the grunts of effort, she was making small whimpering sounds with each thrust. I reached up and ran my hands over her back, feeling the soft, smooth skin making her moans come more often. I then moved my hands down to her ass cheeks, feeling the roundness and firmness of the flesh. I pushed my hands under the waistband of her panties, and felt the same cheeks directly on bare skin. I was squeezing and caressing the warm skin and my actions made Jackie increase her tempo on my cock. I continued squeezing, but at the same time, I increased the pressure on her ass, pushing her down onto my cock more firmly.

Jackie responded by again increasing the speed, and putting her hands onto my shoulders, raised her torso up to gain more leverage for the single point of contact between us. This gave me an opportunity to get a grip on her tits, something I had only been imagining up until now. The nipples were hard and sticking out in anticipation of more direct stimulation. I squeezed the flesh, just as I had been doing with her ass cheeks just a minute earlier. I captured the nipples between my index and middle fingers, squeezing them together as I continued to massage the flesh of her breasts. She was still grunting each time she ground her pussy over my cock, but the grunts were mixed with louder moans of her own pleasure as both her pussy and her tits sent the neurons in her brain into overload.

Normally, when I have sex with a woman (and I don't do men), I like to be able to see what is going on. This room, however, was in total darkness. I was not able to look at Jackie's face, couldn't gauge what her thoughts were, and couldn't see if she was watching me as I would be watching her. I could only imagine what was going on in her mind. I wondered if she had her eyes open or if they were closed. Was she concentrating more on her own pleasure than on mine, or was she interested in making me feel good at the expense of her own enjoyment. So far, neither of us had said a word, just moans and grunting sounds. The experience was centered between our two bodies, no other sensations from the outside were present in the moment.

I was still squeezing and massaging her tits, but took a quick minute to move my hands down her back and start to slide her panties off her ass and down her legs. With Jackie lying on top of me, I could not get them far down her legs, so moved out from underneath her and positioned myself to the side to get a better angle, then completely removed the small cloth. Jackie realized what I was doing and with my body now in a position for her to do the same for me, my boxers went missing shortly after her panties hit the floor. I pulled her back on top of me, but this time we were not crotch to crotch, but rather face to crotch. I felt Jackie grab my cock and start to run her hand up and down its length. She had a good grip on me and I soon felt her warm breath on the head of my cock. Shortly after, her tongue made a few probing licks, then the head was drawn into her mouth. I enjoyed the sensation of the warm, wet orifice that covered my cock, giving me tingles and feelings of arousal within my entire body. I had not been acting entirely as a spectator myself, I pulled her legs apart and started exploring the inner beauty of her pussy with my tongue. Jackie was still just teasing the head of my cock as I started licking and sucking, and the moans and whimpering sounds I heard from her told me I was doing something right. Next thing I knew, she had moved her mouth down the length of my cock, bringing it completely into her mouth. The feeling was great, and I tried to reciprocate my appreciation by moving my tongue even faster, now getting her clit with every few strokes. I could feel her legs tremble and shake each time I ran my tongue over the hard nub, and her moans started increasing in both frequency and volume. My own cock was getting a good tongue lashing, and I decided that if I concentrated too much on my own pleasure, I would come very shortly, and I did not want that to happen, both to prolong the experience and to be sure Jackie received as much pleasure as she was providing to me.