My Journey with Laura

My journey with Laura -- how these sorts of things begin...

It's really odd how you can see these types of encounters happening in slow motion over the years. Little flirts, little glances, sly smiles... they all add up into the sexual energy that sometimes ends with a nice mental fantasy while pleasuring ourselves or sometimes they end up outside of the world of make believe where encounters take place in the flesh. This is one of those such journeys...

Laura had worked for me for nearly seven and a half years at my small accounting firm... She was a great employee in terms of the technical part of the job and was also a bit of a treat to have around the office... although sometimes a bit of a distraction to be honest. Laura was in 40s (maybe early 50s toward the end) in our professional time together. Laura is a single mom, small in stature at about 5 foot 4. Her hair is a different color about every month but usually settled somewhere in the dark red shade for most of our professional time together. She couldn't have weighed more than 125 pounds and dressed her small frame in some of the oddest, and sometimes bordering non-professional, outfits I have ever seen. I don't mean downright revealing, but the skirts were short, and she clearly didn't wear a bra under some of her outfits. Again, not revealing or trashy, but you get the idea... this was the distracting part...

I found myself thinking about her over the years when I masturbated. How those little nipples seemed to be hard in the office and how the skirts would creep up her legs when she would sit down for a meeting giving us all a quick glance of her underwear. Those toned legs down to cute little feet that were always in sandals and that tight ass that had just the right amount of wiggle. I found myself hoping she would wear jeans to work on casual Fridays so I could get a better look at the roundness of her bum. I couldn't help it. I mean after all; it was harmless fantasy!

But it did lead to some flirting on both of our parts. Just a little glance here or there, or she would catch me watching her walk by and give a slight wiggle to all the right parts. We were just having a bit of fun.

Time went on, and as people do, Laura got a different job and announced that she would be leaving. As we do, the other people in the office wanted to have a going away party for her, so I turned the company credit card over to the team to get something planned.

Fast forward two weeks and we were all out at a local casino having a big dinner and going to see a show. As the owner of the company, I stay sober for these sorts of outings out of a sense of responsibility to my team (a few of whom I have had to drive home from such events of the years) and honestly, it's sometimes fun to be the sober person in the room just to sit back and watch other folks lose some of their inhibitions (did I mention we were an accounting firm?) As the alcohol flowed through dinner and even through the show, people were laughing and having a great time, all hugging Laura and telling her how much they were going to miss her, and we really were! As the night was coming to an end, we were all saying goodbye and getting one last hug from Laura (my first for the night) and checking on people's condition to drive. Two of us were completely drink free, so we decided to drive the others home (three passengers in each car) to make sure everyone got home safely. We divided up our small team based on where people lived and I went off to my SUV with Laura, Tim from HR and our top sales guy Mark.

Tim got up front with me and took control of the radio, blasting some 80s hair bands and Mark settled into the back with Laura for our drive. Tim was home first after a short 10-minute drive leaving Mark and Laura in the back seat. I honestly felt like a chauffeur with kids on prom night as Mark was doing all he could to close the deal of the night with Laura. Apparently setting too close as I heard Laura say, "move your ass over" or maybe being a little touchy as I hear her say something about "breaking a finger off" and laying on his best drunk pickup speech about how he had "always had a thing for her". Long story short, she wasn't buying what he was selling, and I had to laugh a bit as we rolled up to Mark's house and Laura simply said "Get!".

Mark was quickly out the door, and I was on my way to drop off Laura without really thinking about the fact that it was just the two of us left in the car. She clearly didn't mind as she crawled up between the seats to take her spot in the passenger seat saying something about "not being able to listen to another shitty 80s song" while she found some sort of a metal station on the radio. We were quickly back up on the interstate heading for her next exit and she was dancing to some song about "feeling the air rush up inside of me"... as she danced, the little skirt she was wearing kept riding up more and more. Half a thigh all of a sudden was mostly exposed and she was still dancing. I couldn't help myself but to catch a quick glance while trying to be the "safe one" driving us home. The song changed as I exited the interstate a bit too fast (caught a bit off guard staring at nearly her entire leg) which resulted in her drunken giggles mixing with my nervous laughter as we rolled to a stop at a stop light.

I nervously apologized for the rough ride as Laura put her hand over my hand that was resting on the center console gearshift telling me not to worry about it. As I started to say it was my responsibility to get my employees home, Laura interrupted me saying "as of 5 hours ago, I don't work for you" with a bit of a nervous laugh. She was correct, and somehow that made me both nervous as hell and completely aware that our relationship was immediately a bit different. The light turned green, we rolled through the intersection and her hand stayed put, right on top of mine.

Through a few more turns and we were basically holding hands as we pulled up in her driveway. I put the SUV in park (moving our hands apart to do so) and turned to tell Laura goodnight. We exchanged a few pleasantries and Laura leaned in to hug me across the console telling me how much she would miss the team.

An awkward hug, based on her small size and the distance across the console to my seat, but she really leaned in, and we hugged for clearly longer than the situation should allow. She pulled back a bit and we locked eyes, just staring and not saying a damn word. It seemed like 30 minutes past (it was probably less than 10 seconds) and Laura quickly leaned back in covering my mouth with hers and simultaneously grabbing my crotch that was barely hiding my semi-erect cock. In that second, all rules of engagement broke down and I quickly found that perfect little ass with my right hand, getting my first squeeze through a thin dress as our tongues explored each other's mouths. She leaned in more, basically getting on her knees in the seat, kissing me somehow deeper and fumbling with my belt, pants button and zipper.

My hand too explored more uncharted areas by pulling her short dress up over her back so that I caught a glimpse of her thong as my fingers found a wet spot through the silky fabric of her underwear. And just as I was starting to rub that wet little spot, Laura was able to free my cock and wrap her hand around the base giving me a hard squeeze.

She immediately dove downward toward my crotch and before my brain could connect the dots, her warm mouth was around the head of my cock as she milked my shaft at the base. Knowing my body, I knew that I was producing a huge amount of pre-cum at this point and I heard her moan, apparently savoring the taste. As she began swallowing more of my shaft, her position across the console gave me better access to parts of her body I had dreamed of touching, tasting... I slide down her thong with my right hand and used my fingers to trace a line down between those perfect ass cheeks, barely touching her little rose (which made her moan more) and into the wetness of her sex.

Exploring her with that single hand, I quickly realized a couple of things. First, she was clean shaven, I mean completely smooth. Second, she had very full outer lips and inner lips that protruded at least an inch out of her wetness! Finally, there was that wetness, she was soaked to the point that her inner thighs were slick with her juices. As I explored, her mouth never stopped working on my cock until I found her swollen little clit. One touch and my cock fell from her mouth as she arched her back and let out an amazing purring sound that seemed to be coming from her entire body. She fell forward a bit across my lap and spread her legs the best that she could to give me better access.

I was able to place the tip of my middle finger perfectly against her little button and slowly started to build up pressure and intensity. She repositioned a bit, pushing my cock flat against my belly, and began kissing and licking my balls, expertly sucking each into her mouth and providing just the right amount of pressure by tilting her head slightly back while sucking. I was in heaven, and I could tell from the gyration of her perfect ass that my attention to her ever-hardening clit was having the desired impact. She moaned louder and raised up slightly to take the head of my cock back in her mouth and quickly slide her lips down to the base of my cock, taking my entire length into her throat. Now I'm not huge, but at about 7.5 inches and a nice girth, I have never had a girl completely deep-throat me, but here I was, sitting in an employee's driveway with my cock being swallowed to the base.

As I was just starting to find the words to alert Laura I was nearing an orgasm, she let my cock fall from her mouth and quickly raised up to stand on her knees in the passenger seat. With a quick crossing of her arms, she pulled her dress off over her head and found her pussy with both hands. Pulling her thong to the side, she found her clit with the other hand and start violently rubbing as she almost whispered that she needed to cum. I quickly leaned in, finding a bright pink nipple with my mouth as my other hand grabbed my first handful of her perfectly shaped B-cup breast.

She was so close... she was leaning into me, and I was holding her up with my mouth and hands on her breasts. She moaned through it all saying "I need to cum" right before she pushed hard against me, forcing me back toward my seat and her against the passenger door. Just as I was going to lean back in, she mouthed "FUCK" as she started squirting against her hand that never left her crotch. Her eyes were closed, her mouth wide open, her nipples hard as rocks, and that hand never stopped rubbing through multiple squirts of liquid that were being thrown across the seat, dashboard and center consol. Finally, after multiple aftershocks, she fell across the console and into my lap.

"I made a mess," were her first words as she again found my cock with her right hand and leaned up to kiss my open mouth.

"You need to pull up these pants and come in" were the next words I heard...