Driving Companion

My name is Bill. I'm middle-aged and married. My life is as conventional as you would expect. Nothing exciting.

I'm a senior manager in my company. Most of my work is in an office, but I sometimes travel to visit certain places relevant to my industry. Unfortunately the travel is not glamorous; just tedious and sometimes stressful. I'm usually just moving from one point to the next and can barely catch my breath.

Recently I needed to visit a facility in a small town a few hundred miles away called Brownville. The work looked interesting but getting there was a challenge. Normally I fly everywhere, but Brownville was remote enough to require flying the other way first, a long layover, another flight, and then a couple of hours in a rental car - almost an entire day lost. It was almost as fast to drive there directly. So I decided I would treat myself to a solo road trip, something I hadn't done for a long time. Like most men in my situation, my life is very busy with responsibilities at home and work. I rarely get time to myself.

The day of departure came. I left very early to beat traffic, and was soon cruising out of my own city. It was going to be a warm sunny day and looked great for a drive. I rolled down the windows, turned up the radio, and enjoyed the freedom of the road.

The first hours went fast, and by nine o'clock I was passing through a well-known college town. I was starting to feel the effects of my early start, and thought it was a good time to stop and have some coffee and more breakfast. I turned off the interstate and soon pulled into a funky-looking place that looked good. I ordered bacon and eggs from a friendly waitress and was soon enjoying them while checking my phone for the messages that were already piling up.

The restaurant was busy with students and others just waking up at nine in the morning. Nearby was a booth with three women in their twenties, laughing and talking away. They were attractive but half my age, so I didn't pay too much attention to them. But as one of them got up to use the restroom, I noticed her shirt said "There's Lots of Color in Brownville."

It caught my eye. If you haven't already checked, there aren't many Brownvilles.

As she was coming back, I called over to her, pointed at her shirt and asked if she was from Brownville. She warily said yes. I explained that I was headed there, holding up some papers to prove it, and that I just wanted to mention the coincidence. She smiled and said it was indeed quite the coincidence, and returned to her friends.

They kept talking but sounded quieter. A few minutes later she came back, accompanied by her friends, and asked, "Are you really driving to Brownville today?"

I confirmed it, again showing the papers She asked why, and I explained my work and where I was from. She kept looking at the papers with my name, company and destination, and finally spoke again.

"Would you be able to give me a ride?"

She started her own explanation. She lived in the college town but was going home to Brownville for a wedding. The bus connections were no better than the planes. She was planning to leave that afternoon, but had to change buses and travel overnight to get to Brownville the next day. She was not looking forward to it. But if I was going there anyway, and could get her to Brownville that evening...

I certainly hadn't expected this and had been enjoying my solo ride. But who was I to say no?

Her name was Kate. She seemed to be in her mid-twenties, about 5'5 with shoulder length brown hair. In most ways she was quite ordinary-looking, but I immediately found her very attractive. Perhaps that was just a dirty old man's thoughts after getting any attention from a young woman. And I'll admit that her Brownville T-shirt was on the tight side.

But I what really got me was her face and expression. It radiated an unusual calmness and confidence. She was appropriately cautious about requesting a ride from a total stranger, but not nervous - or flirtatious - about it. She seemed very mature, and certainly was no goofy college girl.

I had no problem saying yes, and she smiled and thanked me.

Her friends were more skeptical, interrogating me to ensure I really was legit, but eventually gave their assent to their friend going off with a strange man almost twice their age. In fact my age was probably the tipping point - I exuded responsibility and maturity. At least on the surface.

We left and I followed their car back to the house they all shared. Kate said she was mostly packed, so I waited outside, checking emails, and she soon emerged. I helped put her things in the trunk, and soon we were heading back to the interstate.

So my day had suddenly changed. Instead of the silent highway, I now had a driving companion on my road trip - a young woman.

I thought after a few initial words Kate might ignore me and bury herself in her phone. But she kept chatting. For a moment I thought I had made a bad mistake and was doomed to have my ears talked off for the rest of the day. But I quickly realized my original hunch was right and that she was worth talking to. In short order I learned she was indeed 25, a graduate of the local college who had never left, and now worked for herself as a photographer and artist. She missed Brownville and rarely got back because it was too far. I told her a bit about myself, my family and job. The conversation was easy.

Watching the road, I couldn't look much at Kate directly. But I couldn't help but keep thinking about how attractive my travelling companion was. As I said, she was rather plain in some ways and not an obvious hottie. But she had that striking presence and confidence that made her very appealing.

Admittedly, the tight-fitting shirt helped, as I could clearly see the outline of her breasts, along with a pink bra strap peeking out on one shoulder. I had gotten some better looks at the rest of her earlier and knew she had a well-proportioned body and a nicely rounded ass. I actually felt my cock growing a bit as I thought about her tight jeans.

I had certainly lucked out. My life doesn't have a lot of excitement or surprises, and certainly not cute 25 year-olds jumping into my car. I have employees around that age, but try to keep them off-limits, even in my mind. But Kate was just a stranger, and exuded that unusual maturity and presence. She felt more like an equal than someone about half my age. So I felt a bit more free to wonder what she looked like with that tight T-shirt off, and maybe the pink bra and jeans as well.

I certainly wasn't going to try anything. The whole reason she was with me was because she trusted me - a responsible older businessman. However, I wasn't going to tell my wife or anyone else about this either. It was just an exciting secret bonus for my road trip. And if I wanted to think about Kate with her clothes off, well, those were private thoughts for me to enjoy.

I asked about her work, and she promised to show me some of it when we stopped for lunch. She seemed passionate not only about the artistic side, but also the business aspects of trying to make a living from it - though it obviously wasn't very lucrative if she relied on buses and strangers for travel. But I got the idea she liked a challenge and being responsible for herself.

I felt there wasn't much to say about myself, but she surprised me by asking a lot of good questions about my work and career. At first I gave the superficial, non-committal answers that a life of business networking trains you to make. Lots of cliches, forced optimism, and occasional lies. But she kept asking. And so soon I began to surprise myself by giving deeper and deeper answers.

She was a very good listener, responding back in a way that showed she understood and was curious to know more. So I felt unusually relaxed with her. After so many years in the corporate world, disciplining myself to control everything I said, it felt good to open up so freely to someone about my choices, dreams and doubts. She was a random stranger, but again, there was just something about her...something that made me feel I could say anything without feeling guarded or defensive. So eventually I was quite comfortable telling her all kinds of things about my world, including how disillusioned and frustrated I sometimes felt.

She asked if I regretted my career path.

"Not really," I said. "But I always wonder if I'm really being true to myself. Rather than just trapped by the money and needing to provide for my family and all my obligations."

"I think I understand," she said. "But you have to make choices, right?"

"You do. And live with them. Which I can do most of the time."

"You just sometimes wonder what else could have happened," she said.

"Exactly. You can always wonder," I replied. It felt good to say these things out loud.

After a while we started to talk more about families and relationships. I had assumed she was a small town farm girl, but her parents sounded more like latter-day hippies who had relocated to Brownville to follow their own passions. I began to understand Kate better. She had grown up in a loose but affirming environment that gave her confidence but also a remarkably grounded self-awareness. She was very curious about other people, but also had a strong sense of herself and who she was. So she felt no need to compare or justify herself with anyone else. Nor did she feel a need to judge others. I noticed that she only talked about people in positive ways.

I was really impressed. Most 25 year-olds I know are either narrowly focused career types, very judgmental and fixed in their own ways...or just immature and drifting. Kate was neither. Frankly, in many ways she was more mature than me. I never really grew out of the judgmental career type myself.

I mentioned I had married young and we had been together for many years. She continued her probing questions, though carefully, and again I surprised myself by opening up. I was soon telling Kate things I had never said to anyone else about my wife, my marriage and some of our struggles. Somehow I didn't feel like I was betraying secrets or saying anything inappropriate. It just followed from the openness that she radiated herself. Just like with my career, I wanted to tell her these things - things I never said to anyone. She was so patient and, like I said, never judgmental.

I gently asked about her own romantic relationships. She said she had never had a "serious" relationship, though she had had "friends." She said the word slowly.

I mulled that over, staring out the windshield. Then, feeling totally open with her, I asked, "You mean like 'friends with benefits'?"

She laughed, "I think that's what the media calls it."

I replied, "You don't?"

She said, "Why call it anything? It just feels right to be with a guy sometimes. But it would feel really weird making a commitment...like, potentially saying you would be together forever. I couldn't imagine doing that...yet."

"I did...and way before I was 25." I paused. She was quiet too. Then I continued, "It just seemed to be the right thing to do back then."

"Does it still?"

I couldn't believe this woman. We had known each other less than two hours but were having incredibly personal conversations. I confessed, "I don't know. But it's like my job - even more, of course. I can't really change things now."

"But again...you sometimes wonder," she said. I looked over at her. She was looking back at me with open, piercing eyes.

"Yes," I said. "Though it's hard to admit to anyone."

She asked, "Do you ever tell anyone this stuff?"

"No," I said. In fact, I was getting embarrassed. I figured I had crossed the line a while ago and was just feeling sorry for myself. But in the spirit of our open conversation, I told that to Kate. She just smiled. So I went on to say I had even tried talking to a counselor once but it was just too hard to open up.

"You seem to be pretty open with me, though."

"I guess because you're a stranger who just got in my car." She smiled again.

***

The miles flew along. It was getting close to noon when we arrived in a small town I'd never heard of. We stopped at a roadside diner for lunch. It was an unqualified greasy spoon but appealed to both of us. Going inside, I held the door open and saw flashes of pink above her low-cut jeans, suggesting her underwear matched her bra.

As we settled into the booth, I finally got a good look at her again. After hours of talking while looking at the road, rather than face-to-face, I felt I had a pretty good sense of Kate as a person. But I wasn't used to actually looking right at her. Now I could, and I was so fascinated that it was hard to look away. She just had that warm, grounded presence.

Kate brought in her laptop, and while I spent time catching up on messages, she set it up to show her pictures. She was bent over looking at the screen, and I couldn't stop stealing glances at her exposed cleavage and her...well, her tits. Her pink strap was still showing, and now I knew there were pink panties to match. I knew that was no big deal for her generation, but I suppose I was trained in my own youth to get excited by the sight of a bra strap. I thought of the rest of it, holding in the firm breasts that were perfectly evident, and then about her bum shifting around in the seat, wrapped in matching pink.

I was definitely being a dirty old man, but it was hard not to look, especially after our intense conversation. We no longer felt like strangers and I was fascinated by this woman who could make me so unguarded and open. I don't know if she knew what I was doing. But I couldn't imagine Kate being naive that way. Probably she was just playing it cool and was used to men, older and younger, checking her out.

I hung up, put the phone away and looked at the laptop. The images were great. She had photographs of landscapes, people, everything. She had enhanced many of them with different effects and things that I didn't really understand, but it just made them more compelling. I could see they were much more than just iPhone shots. I told her that I didn't know much about art, but she seemed to have real talent.

She showed me some portrait shots. She hesitated over one and said,"I maybe should warn you this is a little different." She opened it. It was a shadowy silhouette of a naked woman. "Very, um, artistic," I said. I hoped for a second it was Kate herself naked, but I could tell it was another woman.

She smiled. "Does it bother you?"

"That's not exactly the right word," I replied.

"What is the right word?"

"Maybe 'fascinated'...but also maybe 'guilty' at being a bit too fascinated," I answered.

She smiled. "I know you're wired to feel that way, but you don't always have to. Have to feel guilty, that is."

I may have blushed. "I guess I am pretty wired that way."

"But you still like to look?" She was still smiling.

"Yes."

She was quiet for a moment. "With some guys it definitely gets out of hand. But I don't think that's the problem you have, Bill."

I looked at her. "What is my problem?" But then our food suddenly arrived, and Kate closed the laptop. She never answered my question.

We talked about other things. I got over my obsession with her breasts and managed to keep my eyes focused up top. She looked around at the other greasy spoon diners. I just saw a bunch of truckers and small-town people with nowhere much to go, but Kate mused about how each one of them probably had an interesting life story. She wasn't naive or flighty - just curious and deeply interested in others. I was ashamed at my own judgmental dismissiveness. I realized she was right.

We finished. I sent a last email and we got back on the road. Kate nestled back in her seat and raised her knees up to the dash, looking very comfortable. "We've got a long way to go, Bill. Let's pass the time - tell me more about yourself," she said.

I said there wasn't much else to say. I had told her so much already, and that frankly it had felt like I was having a pity party for myself.

She smiled and told me I was being silly. "There's a lot more to you, Bill. And I don't think you get to tell your own story much." I said that was probably true.

So I kept my eyes on the road rather than on her raised legs beside me, and started talking. It was rambling and I can't really remember all of it. Some of it was just silly, like telling her my favorite foods. But much was intense and personal, about career, family, my health - anything that came to mind.

I told her how my career seemed to have flatlined. That I had never slept with anyone but my wife. That I had lost much of my religious faith. That I had no close friends. I can't believe how much I told her. She just listened, sometimes asking a small question but nothing more. Yet I felt she understood everything I said. I felt listened to - and never judged or dismissed or told to get it together or to stop feeling sorry for myself.

After a while, I fell silent. Kate asked me, "Bill, are you lonely?"

"Yes. But isn't everyone sometimes?"

She said, "That doesn't make it okay." She reached over and rubbed my arm gently for a few seconds, then took her hand away again. We were both quiet.

I asked, "Are you ever lonely, Kate?"

"Only when I want to be."

I told her what I was thinking - that she seemed to have her life together much more than I did at her age, and for that matter at my age now. Now she was the one to blush a bit, but said "It's just how I feel, I guess."

I told her it was now time to say more about herself. She snuggled back in the seat and told me more of her own life. She had done far more than I had at her age, and yet her life seemed so uncomplicated. She told me about a happy upbringing, about exciting college years, and her choice to stay and pursue her creative side and just see what would happen with it. She mentioned mistakes and problems, but always in a positive light. She never complained. She seemed to learn and grow from everything.

She talked about friends, including ones "with benefits, as you call it". She seemed to have a core of good friends, both male and female, though she was clearly only attracted to men. She had been with a number of guys, but each sexual relationship was a bit different in its intensity. None were really boyfriends or committed relationships. She even confirmed to me another thing I had wondered about - that some sexual acts were not really considered a big deal. A handjob could be almost a friendly courtesy. A blowjob was more intimate but didn't signify a deep commitment, though it was polite for the male to reciprocate. (She winked when she said that.) Intercourse itself, or "fucking", as she put it, was more serious but again could still be a totally casual thing.

Naturally I was fascinated and my mind was aflame with thoughts of Kate sucking some lucky guy's cock and getting...fucked. It was so different from anything I had ever experienced when I was young. She seemed so casual about sex, yet not slutty or teasing either. She even admitted some encounters were perhaps mistakes, but it didn't seem to bug her or give her regrets.

As she talked, her legs still raised and ass almost off the seat, I thought about how exposed her pussy was right there in my car. I imagined slipping those pink panties off and eating her out - reciprocating, the way she wanted. And I was jealous, thinking of guys who had their way with this gorgeous woman. My cock was swelling again as I imagined myself penetrating and fucking Kate. I was sure she was an on-top sort of girl and thought about her riding cowgirl and grinding on top of me, moaning and taking my cock deep while I licked her swaying tits. My mind was getting overwhelmed as I listened, fantasized and drove all at once. And of course I felt guilty about my thoughts.