A Day Trip For Work

Today was crazy. Or wonderful, maybe? Definitely weird. I don't know how I feel about it yet, to be honest. That's why I'm writing this to you, strangers. Hello people I don't know. For some reason I thought you could help me figure out what to do with this.

I like to drive. Which is good, because I drive a lot. I'm a photographer and videographer in ... let's say a mid-size city in one of those middle states. I work for a company that does professional photography and videography — corporate photos, wedding videos, all that kind of stuff. Since I like driving, and due to my wide range of skills, I've become kind of the de facto road guy. When there's a job out of town it gets assigned to me. It's not bad. I get to listen to audiobooks and lectures and podcasts. And I like the alone time, especially bracketing having to be social and engaged with our clients, which isn't my best skill.

I travel alone most of the time. But, when the job is video, at least one where sound is important, our sound engineer comes with me. It's a small company. Everyone does everything within their specialty. When I do photography, I do all the editing as well. She does the sound side of things. Because that extra dimension of video makes it more complicated, it takes another person to do it efficiently and well.

It has been about six weeks since Elisa and I were on the road together. Then today we did a job at a ranch a couple hours away. We get these kinds of jobs a few times a year, where people hire us to come and video their elderly parents or grandparents while they just talk, and tell all their stories. Then we turn it into something cohesive and nice and put in music that gives you the warm fuzzies.

It's always a little weird when Elisa is with me. For me, at least. I've had a thing for her since not long after I started working with my company around two years ago. Elisa and I have an easy rapport and share common interests in books and absurdist cinema, among other things, which we bonded over pretty quickly. She has long, dark hair with loose curls that you will never see unless she's letting it down to put it up tighter. She doesn't wear makeup, not that she particularly needs to. My point is that she doesn't seem to put much thought into her looks. She plays soccer in the state amateur league, which she told me is a fairly new hobby. She's not like a girly girl. She's cute as hell, and has a soccer player's thick thighs and ass. Would it be creepy for me to say I sometimes fantasize about her sitting on my lap? Yeah, after writing that I'm going to say it's creepy. But you're strangers, and I'm trying to he honest.

I don't listen to my audiobooks when Elisa travels with me, to not annoy her. We usually fill the time with conversation, but the silences aren't awkward. We get on pretty well. I've never said anything to her, but she'd have to be pretty dense not to notice I'm attracted to her. It's just that it doesn't matter because she's been serious with the same guy since I met her.

So, today...

After we wrapped up just short of 5 hours of shooting this fairly interesting old lady talking about growing up on this ranch during the Great Depression and the Dust Bowl, we got my car loaded up and headed back to the studio. The days are already getting much shorter, so the sun was setting as we were getting on the road.

I was tired, but I knew that if I asked her about her boyfriend she'd talk for a good half hour, and I wouldn't have to do anything but listen to her. Even if it is about her boyfriend, it's nice to listen to her.

"We broke up," she said, "about a month ago," a seriousness overtaking her.

"Oh," I responded, out of true shock. "I'm really sorry."

"It's okay," she said quickly. "I mean, it's not okay. It's been hard. And lonely. But it was for the best, I think. We grew apart, somehow. He's been concentrating on his career, and then he got a job offer in Lincoln. So... he left. And I stayed here. And that has pretty much been that."

I was heartbroken for her. I couldn't imagine losing someone that quickly after being together for years.

"That's really shitty," I said, honestly. "If there's anything I can do for you, cover a job or something on a hard day, let me know."

I looked over at her and she was looking straight ahead at the road, lips tight. We sat in silence for several minutes.

"Listen, you can say no to this," she said suddenly and quickly, her voice quivering, hands suddenly nervously animated. "I know you're attracted to me. And you're a good guy-"

I laughed. "What?"

"You don't have to be embarrassed. You take little glances at my ass all the time. I mean, you're pretty discreet about it, I guess. But I know when you're looking at my ass. And, other than that, we've known each other for years, and I like you, and I trust you."

"'Okay?" I responded, unsure still of where this was going.

"Right, so... " she paused. I looked over at her, she bit her lip, then said, "Would you mind getting me off?"

"Holy fuck!" That was my reaction in my head and out loud.

She laughed nervously. "I mean, I masterbate, but it's not the same kind of orgasm when you masturbate as when someone else gets you off. There's science on that. Different endorphins are released." She continued, talking very quickly, "I understand if you aren't comfortable with it. It's weird, I know. And we have to work together. But I need to get off. And I don't want to just like hook up with someone on Tinder, which seems like it would be horrible. And, well..." she slowed down, "we've got the time."

And that's when it hit me what she was actually asking. "You mean, right now?"

"Yeah."

"While we're driving?"

"Yes. We've got almost two hours back to town. It's already dark, so nobody's going to see anything going on in here." I was silent for a moment. She added, "But, to be clear, I'm just asking you to finger me. This one time. I don't want to do anything else."

So, obviously this was weird. Of course I wanted to get her off. I also didn't want to ruin what relationship we have, or might have. But, then, considering there is pretty much no overlap between her ex and myself, so unlikely that she's all that attracted to me, I also figured this was probably the only chance I would ever get to touch her in any way. I made a rash decision.

"Okay," I said, swallowing, only half sure, but taking my chances.

"Really?" she responded with an odd mix of relief and excitement.

I nodded, then looked over at her. She was smiling at me. Fuck. There was no way this was going to end well for me.

"I'm not sure exactly how to do this," she said, looking at our surroundings. She unbuttoned several buttons that ran down the front of her loose black pants, then slouched in the seat a little. She reached over and took my right hand in hers, pausing. "You're sure about this?"

"Yeah," I said, nervously. "It's okay for me to be turned on, right?"

She laughed, then took my hand and placed it at the opening of her pants. We were both visibly nervous.

I think she expected me to put my hand down her pants right away, but I was too nervous to do that. I ran my hand down her thick thigh, squeezing firmly, feeling her. She breathed in quickly as my hand moved over her. I took some time, feeling her warmth in my hand, letting my fingers roam where they would never otherwise go. She seemed to be holding in a moan. As I felt back up toward the opening in her pants, she spread her legs. I moved my hand, awkwardly, to feel her far thigh, squeezing it while letting my wrist rub against her crotch. She pressed her hips softly into the pressure.

I took my eyes off the road for a moment to look at her as I asked, "Are you ready?" She was breathing deep already, her chest moving up and down steadily, lips slightly parted. She nodded at me in short, confident movements.

I pressed my fingers against her skin, running them along the elastic of her panties, which gave way and slipped over my fingers. Her skin was soft and warm. I was glad I had warmed my hand up feeling her thighs. Straight from the steering wheel might have been a shock.

As my hand slid into these unseen reaches, my fingers entered the forest of curly hair of her thick bush. Already, I wanted more. Images of what she might look like with her pants off flashed through my mind. My fingers delighted in it, spreading out and letting the curly strands roll over and between my fingers. After a minute I pressed forward and soon came to the cliff that would lead to her pussy. As I reached further, she angled her entire body toward me, putting my wrist at a less awkward angle.

"Just a moment," she said. She reached to her side and pressed the control to move her seat forward, further relieving the awkward angle of my wrist, and bring more of her into my periphery. She then leaned the seat back as far as it would go.

Now in a more comfortable position for both of us, I spread my fingers to take the dive and pass on each side of where her clit would be hiding. My fingers turned down and ran down the sides of her labia. With my fingers between her legs and my palm pressed into her mons, it was hard to concentrate on the road. I let my middle and ring fingers close in on her labia, and massage it in slow circles.

She moaned loudly as her hips pressed into me.

"I'm sorry," she said. "I'll try not to moan."

"Oh, please," I found myself saying. "Please moan for me. I want to enjoy you enjoying this." Then I added, more stoically, "Plus, I need feedback on what you like, of course."

She giggled. "Okay," she said, quietly. "Because you begged so nicely."

My fingers continued massaging her labia while she let out soft purrs. I felt her labia slowly swell between my fingers. The thought of sexually exciting her quickly had me hard. After a few minutes her wetness began to spread into her bush and coat my fingers. I pressed my middle finger down a little more firmly and ran it sidelong across the lips of her labia, drawing a gasp from Elisa and a twitch of my erection. Her lips were wet and swollen with arousal. I ran my now wet fingers up and down her lips, spreading them, playing with them, squeezing them between fingers. Her hips fidgeted, letting me know she was enjoying it. But I wanted her to make more noises for me. Because of me.

I placed my middle finger at the bottom of her opening, my fingertip quickly lubricated with her wetness. I slowly bent it toward my palm, spreading her lips and slightly entering her pussy. Her wetness spread up my finger. Her pussy was smooth and soft. As my fingers explored her, applying pressure to the walls of pussy, she let out a slow, overwhelmed, vibratoed, "fuuuuuckk." As my fingertip approached my palm, I softly drug it up the short length of her clit, which was small and thin. A high pitched "oh" slipped past her lips as her hips jerked several times, pressing her clit into my finger over and over.

I looked over at her. Lit by the dash panel, I could see her eyes were closed, and a small, parted lips smile was on her face. Maybe it was the lighting, but she seemed to be glowing. I wanted to touch myself. Or, really, for her to grab my cock. No matter how much I masturbated when I got home, my balls were going to ache for a day, at least.

I wasn't sure if I should play with her clit first, or finger her first. She asked me to finger her, which made me think that she probably needed penetration to orgasm. So I decided that maybe playing with her clit a little would be the place to start.

I softly placed my two lubricated fingers on either side of her clit, protected by her labia to begin with. I faintly squeezed them together, while moving my hand in a small circle. Almost immediately her breathing grew deeper, which was promising. I continued for several minutes, slow and deliberate with a light touch. Soon she was moaning in rhythm with my movements. I pressed my fingers together a little tighter and changed from a circular motion to pressing my fingers into her fleshy mound, stroking up and down on her firm little clit. She gasped and moved her hips into my strokes over and over again. She began to breath harder, letting out little squeaks.

"Faster", she whispered after a few minutes. I did as she asked, moving faster up and down her clit. I could feel her entire body writhing under my touch. I looked over and she was fondling one of her breasts through her blouse. "Don't stop," she squealed. Nonsense sounds came out of her as she began to frantically press her hips into my movements, over and over and over.

Suddenly she placed her hand over mine hard enough to stop my movement. Her shoulders moved forward, bending in on herself. I could feel her muscles convulsing far under my fingers. Her breathing stopped for over 30 seconds before she gasped again, relaxing.

She let go of my hand, straightening herself out and looked at me. I took my eyes off the road to meet hers. "God, I needed that," she said, with gratitude in her voice and a sparkle in her eye.

I moved my hand down further in her pants and easily slid a finger into her now surprisingly wet pussy. Her eyes got wide and her lips parted.

"Oh?" she wondered.

"Yeah?" I asked, desperately.

"Yeah," she replied, lilting.

She spread her legs wide toward me, pulling her knees up and placing one foot on the dashboard and the other on the seat up close to her ass. I pressed my hand into her crotch, sinking my finger into her as deep as I could. I wanted to feel all of her. Her panties pulled down a little with this movement, exposing some of her curly public hair. I tried to push further, exposing more of her, but she pulled them back up over my hand, modestly and without comment.

She stared at me with eyes wide and most of her lower lip between her teeth as I held my palm firmly against her mons while sliding my middle finger slowly in and out of her by pressing into her firmly. Elisa is a small girl, and I could easily press up against her cervix with the tip of my finger. I made sure her little clit got to feel the pressure of my protruding finger pressing into her interior, as well. I wanted her to feel as good as possible. I told myself that the first orgasm wasn't the one she had been needing. She needed to cum a lot harder than that quick little thing.

She wrapped the fingers of her left hand around my forearm, as I kept the steady movement going. Little by little she squeezed my arm tighter, and little by little I sped up my pace. Soon, her moans weren't the only thing filling the car. I could smell her arousal in the air. Her wetness was spreading across my hand, coating it, running down my fingers. I peeked over and could see my knuckles painting dark spots on her thin cotton panties. I kept this up until the muscles in my arms were aching. Her obvious arousal kept me going through the pain.

Several minutes later, as I looked at her again, her fingers were wrapped firmly around my arm, her eyes were still closed, and she had unbone one button on her blouse and had her other hand inside, making circular motions over her left breast. I wanted to tell her how beautiful she was, how much she had me turned on. But, I didn't want to take the chance of breaking the mood for her. I kept silent and imagined what it would be like to feel her hard nipples between my fingers.

Her hips began to squirm a little as they softly pressed into my palm. I changed up what I was doing, from pressing into her, to letting my finger swirl around inside her, pushing against the tight walls of her pussy, my fingertip circling her cervix. She reacted to that with delight. Her moans went up several steps in pitch. Her hips bucked into my palm hard and fast.

"I don't know what you're doing," she whispered, "but don't stop. I'm about to cum so fucking hard." The last part breaking out of a whisper.

Her left hand pulled my palm into her harder as her hips moved into me. Her hand inside her blouse moved more frantically. Her breathing quickened. We were moving so hard against each other I could hear the suctioning sounds of my hand moving against her, both of us coated in her wetness. The puffy walls of her pussy clenched tight against my finger, then let loose, then clenched again. She moved her right hand from her breast to on top of my hand again, pressing firmly down on it. She screamed nonsense syllables as she leaned into me so far that her breasts pressed against my arm.

I took in all of this with awe and excitement. The movement of her lips as she came is forever burned into my memory. I held my hand still, finger still inside her, as she relaxed and laid back into the reclined seat.

"Holy hell," she said. "I guess I really needed that." She breathed. "That made me light headed," she added as she leaned back. I smiled at her, ecstatic but not knowing what to say. She smiled back, catching my eyes as I glanced back at her. "Thank you so much," she continued. "You really committed to getting me off."

"It was even more exciting than I had imagined," I said, slowly, trying to figure out how to put it.

Elisa laughed. I looked back at her. She bit her lip, then looked down at my hand still in her pants, my finger still inside her. "Your arm must be really tired," she said.

"It feels like it's going to fall off," I told her, honestly. "But I can keep going if you want..."

She exhaled. "I'm not gonna stop you." She added, after a moment, "I doubt I'm going to cum like that again, but it still feels really good."

I looked at the clock and noticed that, somehow, we only had about half an hour left, which meant about twenty minutes before we were back in the lights of the city. My finger felt pruny inside of her, but I kept it playing with her, moving in various patterns and speeds. The weirdest part was that, with my finger buried in her pussy, we had a fairly normal conversation the rest of the way back to the city, mostly discussing the latest movies we had to recommend to each other. Every now and then I would do something to elicit a moan or an expletive, followed by a smile, but it was otherwise a normal conversation.

"We should probably..." she said, as we approached the edge of the city.

"Right," I said.

I slowly slide my finger out of her pussy, which elicited a soft groan from her.

"I've really made a mess on you," she said, reaching into her purse and quickly pulling out a napkin and wiping her juices off my hand. Much to my disappointment, and with an embarrassed look from her.

She buttoned her pants and pulled them up. She moved the seat back to upright. Once this was done she turned the conversation back to work, asking when I would have the video edited and ready for her to work her magic on it.

As we pulled into the parking spot and I put my car in park, she looked at me, a bit embarrassed. "Thank you, again. You were..." she breathed in sharply, "You made me feel really good."

I smiled, awkwardly. "I couldn't have done it without you," I said, thinking it would be funny. She didn't laugh, though.

"Do you need help unloading?"

"No," I said. "Thank you," not wanting either of us to have to acknowledge the erection that would be bulging against my pants. "It's not much, I can get it in one trip." We both knew that was a lie.

She smiled at me, grabbing her purse. "Okay. Have a good night. I'll see you tomorrow." She got out quickly and went to her car. After a minute or two, she drove off.

And... now I'm here, writing about the whole thing, trying to make sense of what the fuck just happened. But I'm not sure that I have any more insight with it out of my head.