Carpool Problems

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Carpooling to help a friend leads to interesting places.
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m_storyman_x
m_storyman_x
10,433 Followers

I had to work to keep enough concentration on the twisting two lane highway and still look over at Julie sitting next to me. She had her skirt pulled all the way to her waist, exposing the lacy little thong panty she wore and the top of her dress pulled down to expose her incredibly sexy breasts. I could feel the heat of her pussy flowing into my fingers and the wetness of the material covering her crotch as she pressed my fingers between her slightly spread legs. It certainly wasn't the safest way to drive! I knew I was going to be in trouble with my wife if I did anything more than this. Hell, let's be honest, I was going to be in trouble for what I was ALREADY doing, even if it WASN'T my idea. As she pressed my fingers against her pussy with her right hand, she reached over to my lap with her left, gently running her fingers along the material covering my quickly hardening dick. If I was smart, I'd pull my hand from between her legs and tell her in no uncertain terms that this kind of thing was inappropriate. Instead, my fingers, almost of their own free will moved, stroking up and down her fabric covered pussy lips. She moaned softly in pleasure before whispering, to no one in particular, how good it felt.

How the hell did I get into this mess you ask? Well....it's actually a fairly long story, but it all stems from just being a nice guy.

One day after work I was coming out of the building and saw a young lady bent over the front of her car, the hood open. She wore a short red dress with white poke-a-dots, that pulled so far up her thighs when she bent that I swore I could almost see her panties. Yeah, I know. I can be a dirty old man sometimes. After enjoying the view as I walked towards my car, the fatherly side of me kicked in. She was clearly young enough to be my daughter, and she was just as clearly having car trouble. I'd always hoped that if one of my daughters was having trouble some nice guy would help them out instead of leaving them as prey for some lecherous predator. So I stopped.

I offered to help her which she eagerly accepted. It didn't take long before I had diagnosed a bad battery. It was going to have to be replaced, BUT, to get her home I could jump her car with the cables I kept in the trunk of my car. That would get her home, wherever that happened to be. I jumped her car and sent her on her way, driving out of the parking lot only two cars behind her. I was mildly curious and then amused as each turn she made was the same one I intended to make. I wondered if she thought I was stalking her when we both turned onto the same twisting two lane highway. Twenty-five miles later I saw her car slow and then pull into a gravel driveway. I was about to pass when her driver's side door opened, and she stepped out. I looked in my mirror and saw her put the hood up.

With a sigh, I found a driveway and turned around, driving back to where she was stopped. She was a little startled to see me pull up again, and admittedly a bit leery. I assured her that I hadn't been stalking her, but was headed home myself. Several exchanged comments later we realized that I lived just a bit farther than she did and we actually took the same route to work. Simply coincidence, and for her at the moment, a happy one. She explained that the car had started to stumble and sputter so she pulled off. With the battery still dead, there was no way to do much of anything. I couldn't get my car close enough to hers to jump it without blocking the moderately busy highway, something I wasn't anxious to do.

The driveway she had pulled into was the entrance to some farmer's field. So we called a tow truck and I sat with her, chatting until it arrived nearly an hour later. He hooked the car up and I gave him instructions to take it to a reasonably priced mechanic I knew of. I offered to drop her at her house instead of having to pay the tow truck driver the extra mileage to do so, and we were off.

My wife was somewhat miffed that I was nearly two hours late from work, but after I explained what had happened she realized that I was just doing what I always did, rescue someone in distress. Some people can't stand to see a turtle struggle across a road and have to stop and "help" it get across. For me, young women broken down are my weak spot. I have three daughters and I always hope that if they need help, someone kind will help them out. After I had explained the whole story she suggested that maybe I should offer her a ride to work, since her car was now at the shop. The fact that she was married made that decision a bit easier. I am after all, still a dirty old man!

She had given me her number, so I called and after a short discussion I agreed to pick her up at her house since her husband had to leave for work before she did and she wouldn't have a ride to any place we could meet. I agreed, and the next morning I picked her up on my way to work, having to detour only a few blocks from my normal route. Wednesday led to Thursday which led to Friday which led to a week and longer. Her car was in the shop for nearly two weeks before she got it back. By that time we had discussed that we should carpool and save some money, which I was coming to understand was in short supply for her. I agreed, but suggested that maybe I should drive. Not that I didn't trust her car, but, well, I didn't trust her car. She thought that was amusing, but she agreed. I'd drive and when she could, she'd give me some gas money. My wife was, surprisingly, okay with it. But then she hadn't met Julie yet and had no idea just how attractive she was.

Julie always wore nice looking clothing to work. Dresses and skirts were her norm. Today's young ladies' 'professional' attire has much shorter hemlines than what 'professional' was for my generation. But then she was almost half my age. At twenty-six, she could easily be one of my daughters, but that didn't stop me from admiring her long shapely legs that were on display every morning and afternoon. Even as the cold winter months approached and bore down with their cold and wind, the skirts stayed provocatively short. Usually her skirt would hike up slightly as she sat in the seat only a few feet from me. Sometimes it would hike up more than slightly, and a few times I swore that I could make out the color of her panties, though I never made it at all obvious that I looked or even was interested in looking. But trust me, I LOOKED!

As the months passed, we talked about many things. Politics, work, family, and other things. Some days she spent much of the ride to work venting about her asshole husband. And based on the stories she told, he was just exactly that, an asshole, maybe a dickwad or even a shit head. But asshole really did fit him well. On one particularly warm summer Monday, she spent the ride to work in silence, clearly upset. It wasn't until the ride home that she finally opened up about what happened over the weekend. We had so far managed to avoid any sexually related discussions, but what happened over the weekend seemed to open the floodgate for her.

The two of them had gone to a pool party with some friends. Her asshole husband had, once again, had wayyyyy too much to drink, and thought it would be cute to flash his wife's tits at the other guys. She did after all, have a nice curvy chest. After he had pulled her bikini top off, exposing her to everyone, she ran into the house to the bathroom. He followed a few minutes later to 'apologize'. His idea of apologizing to her was to get her completely naked in the bathroom and fuck her. Unfortunately, he did what she described as his usual performance. He got her turned on, stuck his dick in her and fucked her until HE came, leaving her unfulfilled and alone, still naked, in the bathroom. She was once again left to finish herself off. This apparently was what he considered to be normal sex.

I assured her that was not 'normal' and that he was indeed an asshole, for both pulling off her top and for trying to apologize with sex. She wanted to know what I considered 'normal', in great detail. That discussion led her to a query about my sex life, which I dodged as well as I could before dropping her off at her house.

The next morning she quickly brought the topic of sex up again. I suggested that this wasn't the best subject for two married, but to different partners, people of the opposite sex to be discussing. She disagreed and insisted that discussing sex in general was a healthy topic for friends to discuss, since if you couldn't trust a friend with your secrets, who could you trust.

She badgered me all the way to work to tell me what I thought perfect sex was. It wasn't until the ride home after work that I finally gave in and described what I considered 'perfect' sex. Once that had been described she wanted to know when the last time I had perfect sex was and I had to admit that it had been many years ago. I was also forced to admit to her that sex was fairly infrequent. Not that I didn't WANT IT, but that my wife wasn't nearly as drawn to sex as she had been in our earlier days. Instead of several times a week, it was now several weeks per time. She seemed somewhat stunned by that admission. With some level of frustration she commiserated that we both suffered from a lack of satisfying sex. I quickly added that it was nothing that either of us COULD or SHOULD do anything about. I was glad that the conversation didn't come back up the rest of the week, or even the week after.

It was several weeks later, on a Monday again. It seemed that Mondays were when she was most upset because her jackass husband did stupid shit on the weekends. "I still don't believe what he did yesterday!" she said angrily.

"Oh? What did he do this time?"

"He made a bet with one of his buddies about whose wife was hotter," she said with a scowl.

"Where the hell did he do that?"

"We were at a barbeque with some friends."

"These the same friends as the pool party?"

"Yeah. Pretty much."

"I see. So he made a bet. That doesn't sound too bad."

"Oh. Trust me. It was bad. First off, both Sheila and I had to get naked in front of EVERYONE so they could vote on who had the hottest body."

"I can see where that would be embarrassing. Why didn't you just go home?"

"Couldn't. Andrew wouldn't let me. He said I could strip or I could fucking walk home."

"Ouch. I suppose the other woman was just as upset?"

"Surprisingly, no. She didn't seem to mind at all. I think she used to be a stripper or something. Anyway, once she was naked I didn't have much choice."

"Sorry."

"Oh don't be. That isn't the worst of it. All the guys voted and I didn't win. Sheila did."

"Oh damn."

"Yeah. Well then I found out what the bet was. The loser had to watch his wife give the winner a hand job, right there in front of everyone! NAKED! God I've never been so embarrassed!"

"I can see why you would be."

"I had to stand there, with everyone watching, and jack off John. And when he tried to stick his fingers in my pussy, Andrew just laughed! I thought he was going to come over and stop him, but instead he walked over to Sheila, who was watching me jack off her husband, and he hugged her and put his fingers between HER legs!"

"I'll be honest. I don't know why you stay with that dick wad!" I said, feeling more than a little anger at how he had treated her.

"Sometimes I think that if I could afford it, I'd leave the asshole. But I can't," she said quietly, falling into silence the rest of the way to work. She sat in the passenger seat, looking out the window, apparently lost in thought until we parked. "Thanks. I'll see you after work," she said as we walked to the building doors.

"Sure. Have a good day. Well, as good as you can," I said, reaching out to wrap my arm around her as we walked, giving her shoulders a quick sideways hug.

After work we met as usual just inside the exterior door of work, where it was still cool, and then walked to my car. She seemed to have a bit more spring in her step than she did in the morning, which I considered a good thing. She had on a thigh length blue dress that had a halter style top, leaving her back bare. I suspected that was due to the heat forecast for today, which didn't disappoint. It had to be at least ninety-five degrees, but the heat boiling up off the asphalt parking lot made it feel like at least two hundred. I used the remote to start the car even before we got there, giving the air conditioning a chance to start to diminish the heat that assuredly had built up inside. I unlocked the door and dropped into the driver's seat.

I'd watched Julie climb into the car several hundred times over the last eight months. Every time she did exactly the same thing. She placed her left hand on her left butt cheek and swept her hand down to straighten her skirt as she lowered herself gracefully down into the low bucket seat on the passenger side. So when her routine changed, I noticed. Her left hand pressed to her thigh, just below the hem of her blue dress and swept up to her butt as she sat down, giving me a quick flash of bare thigh and butt cheek as she lowered herself down into the seat. "Oooo. Hot!" she said as her bare cheeks pressed on the tan leather seat.

I tried not to make a big deal of her change in habit, but my brain didn't seem to want to let go of it. I forced myself to put it aside as I pressed the ignition button to "start" the already running car. It only took a few moments for me to buckle up and twist in my seat to back out of the parking space. As I turned back to the front I couldn't help but notice just how far down the V of the front of her dress scooped, dipping well down between her breasts. My brain did the math and I realized that with the backless dress top, she couldn't possible have a bra on, unless of course it was one of those glue on things. Either way, my brain couldn't help but recognize that the seat belt was pulling the dress slightly to one side as it pressed between her breasts, exposing a considerable amount of the creamy white skin of her right breast.

I did my best to ignore what my body was doing, hoping that she wouldn't notice that there was now a bulge in my lap that I just didn't have any way to adjust or hide without her seeing it. I drove through the city streets, glancing over at her occasionally as she sat quietly, just staring out the windshield.

"Penny for your thoughts?" I said as I merged onto the four lane bypass that would take us to the two lane highway that made up most of the trip.

"Huh?" she asked, almost startled out of thought.

"I wondered what you were thinking about so intently," I asked her.

"Oh. Nothing really," she said softly, turning her head to look back out the windshield.

I'm not a completely clueless guy. I could tell it wasn't nothing. Her fingers were rolling and unrolling a portion of the hem of her skirt, making it a couple inches shorter before she unrolled it again. Up and down she rolled the hem of the skirt as we traveled down the road, finally slowing and exiting off onto the two lane highway. I knew that she'd talk when she was ready, so I didn't push.

"David. Can I ask you a question?" she said quietly, still looking intently out the windshield.

"Sure," I answered with a shrug.

"Do older guys like looking at younger women?"

I chuckled. "Yeah, right. Come on Julie. You know damn well that most old guys fantasize about younger women. What are you really asking?"

"Do YOU like how younger women look?"

"Of course," I replied.

"Do you like how I look?"

"You're a very pretty young woman."

She turned part way in her seat to look at me. "That isn't what I mean. I mean do I look sexy? If I took my clothes off in front of you, would you wanna have sex with someone that looked like me?"

"Julie, what makes you ask something like that? I mean, we're both married. This isn't exactly the kind of thing we should be talking about."

She looked down at her hands and was silent for several long seconds. She moved her hands from her lap to up behind her neck and in a few moments she pulled down the dress top, completely exposing her from her stomach to her neck. Her breasts were a nice full C cup and didn't look like they needed any support to hold their shape. Her areolae were bright pink and about as large as a silver dollar with a nickel sized flat nipple in the center. I could see that both nipples were puffed out from her areola, shaped almost like two small cones. "Do you think my body is hot?"

"Julie. This really isn't appropriate," I said quietly, not wanting to hurt her feelings. Truthfully, I didn't really want her to put her dress back up. I did like the way she looked and my body was making it clearly obvious, if she chose to look.

"I know. It's not like I'm asking you to have sex with me. I just wanted to know if you think my body is hot or not."

"Is this because of what happened yesterday?"

"Sort of," she answered quietly.

"Look Julie. You're a truly good looking young lady. Any guy would think so. So you don't have to prove anything to anyone. Just know you are."

She twisted back in her seat and looked out the windshield, leaving her breasts completely exposed. Not that anyone could see her anyway, I continued driving down the two lane highway. After she sat for several long minutes she reached down and pulled her skirt up to her waist, exposing all of her creamy thighs and the tiny lacy pair of pink thong panties she had on. She reached across to the steering wheel and gently pulled my right hand off the wheel and to her lap. She pressed my hand between her legs, spreading them as far as the foot well of the car would allow. She shifted her hand on mine, pressing my hand flat on her so my palm was pressed to her mound and my fingers were pressed against her pussy lips.

"If he doesn't care if a guy puts his hands on me, it might as well be someone I want to put their hands on me," she whispered.

I could feel the heat of her pussy flowing into my fingers and the wetness of the material covering her crotch as she pressed my fingers between her slightly spread legs. As she pressed my fingers against her pussy with her right hand, she reached over to my lap with her left, gently running her fingers along the material covering my quickly hardening dick. If I was smart I'd pull my hand from between her legs and tell her in no uncertain terms that this kind of thing was inappropriate. Instead, my fingers, almost of their own free will moved, stroking up and down her fabric covered pussy lips. She moaned softly in pleasure before whispering to no one in particular, how good it felt.

I could feel her hand grip my cock through my slacks, squeezing my fat shaft while my fingers gently stroked the wet crotch of her panties. She moved her hand from mine, waiting with her hand only a few scant fractions of an inch from mine, waiting to see if I was going to pull my hand away. I felt her squeeze my cock in what I took as appreciation that I wasn't jerking my hand from between her legs as her other hand moved farther from mine. I felt her body move and looked over briefly, her legs and back lifting her butt off the seat as she pushed the thong down her hips. She didn't try to move my hand, but pressed the waistband of her panty down between her legs until it cleared my fingers. Suddenly I could feel the softness of her skin, the smoothness of her outer lips and the wetness of her slightly protruding inner lips with my fingers.

Without any obvious instruction from me, my middle finger pressed between her wet lips, feeling her body close around my digit. She sighed slightly before lifting both feet from the foot well. She trapped my hand between her thighs as she pulled her knees to her chest and used her right hand to push her panties down her legs. In moments she had the tiny pink bit of lace laying on the dashboard. She must have discarded her shoes before she pulled her legs up, because when I looked over she had both bare feet on the dash, pushing her knees apart to give my fingers more room.

m_storyman_x
m_storyman_x
10,433 Followers