A country girl for a city boy (M/F) | 2016

In the mid '90s, America Online was the only portal I had to the wired world. Mostly this was used just for posting on various message boards and starting the occasional chatroom flame war over which bands sucked. As I became more comfortable with how chatrooms worked and more familiar with the various sub-chats, I ventured into more locally oriented rooms.

As a skinny 18-year-old senior in high school, I wasn't that popular with the girls, so this new realm of chats opened up some interesting pathways for me. Looking back on everything, I pretty much recall most conversations as being fairly innocent. Exchanging pictures was not the norm and a lot of times I was much too scared to dive into erotic pursuits with whoever was on the other side.

In the summer after I graduated from high school, I interacted with another 18-year-old girl who claimed to be from a nearby rural community. I knew the name of the high school she went to and where it was, but I was about 30 minutes away by car and from a much different cultural backdrop.

I can't say we hit it off at all at first. She was damn aggressive and acted as if she had something to prove. I was out of my depth and regularly ignored her because I was unclear of her motivations. One day, though, she sent me a sexy picture of her laying in a pile of hay with these incredibly short denim shorts and equally mind blowing cowboy boots. She had a flannel shirt on so I couldn't get a good read on her curves, but I was immediately enticed to talk to this girl on a more regular basis.

A short time after sending her picture (she didn't even ask for mine), she became more flirty and eventually that led to my first true cyber sex experience. In this scenario, she claimed to have snuck under my desk in the dark. She made it a point to say she had painted her finger nails with glow-in-the-dark green paint and then described how she pulled out my cock and made me watch her illuminated fingers pump away. A vivid description of a blow job followed, but by that time I had already blown my load twice. Again, this girl did not ask for anything in return, yet I had the sneaking suspicion she really wanted to meet me.

So, after a few more days of chatting (strangely we didn't go anywhere near cyber sex), she brought up how she wanted to meet, so we agreed to set up a face-to-face at a local mall. Shit ended up being awkward as hell and she really wasn't all what she was cracked up to be (I'm sure I wasn't either).

Despite having a bit of a butter face, I liked her eyes and her butt and legs were still smoking hot. We spent about 45 minutes with each other and went our separate ways. There really wasn't much chemistry there and I really doubted if we would ever chat again online.

So, one day I get an e-mail from her saying she wanted me to come over her house (which was on a farm). I'm thinking to myself, hell no, as I had no idea where I was going and how many of her brothers would be there to kick the shit out of me. She told me she would be alone. Her family went to church on Sunday mornings (and this was just about an all-day affair) and she would simply fake being sick to stay home. I had an excuse to go out that way because I sometimes played paintball with friends in the general vicinity.

I thought long and hard about this situation and figured I might as well take a shot at it. I had no reason to trust her, but the thought of pussy overwhelmed me and thankfully she gave me excellent directions to her place.

I remember pulling up on the dirt lane and seeing some fairly large silos and the random dog running around. I was way out of my element and almost turned around, but the dick wouldn't let me. I pulled my car near house and exited. I didn't hear the sound of anyone and wasn't quite sure what door to knock on.

At that moment, her head popped out of a window and told me to come to the back door. I walked nervously over to the entrance and was greeting by this girl wearing those sexy boots and Daisy Dukes. Oh and fairly raunchy red bra.

My cock almost leaped out of my jeans, but thankfully I was able to hold it together as she led me into an area which I guess looked like a living room area. She sat me down on the couch and I was tongue-tied. She flipped on MTV and started dancing to whatever random video popped on. I sat there and stared at her very sensual movements and couldn't believe what kind of situation I got myself into.

She stripped off her bra first and flung it on the ground. She was rather flat-chested, but I didn't mind one damn bit. She plopped down in my lap and started shoving them in my face. I grabbed a chunk of her ass as ground her body into my erection.

It was at that point where I pretty much broke away from whatever nervousness I had and pushed her down onto the couch and began kissing her. In the midst of all of this, I began fumbling with my pants in an attempt to free my cock. She was doing the same beneath me, struggling to get out of those shorts.

Eventually she got those off (while still wearing the boots!) and my bare ass was on top of her. Being ever responsible and scared shitless since my one friends had just avoided contracting the AIDS virus from a local country girl who would go on to become a national spokesperson (and also die from the disease), I brought several condoms with me that I had been given in a health class in high school.

Her hands were very skilled at putting on the rubber and I immediately had visions of that glow-in-the-dark hand pumping away at my cock. When the rubber was secured I pushed her back on the couch and didn't waste any time entering her. Her tightness sucked me in, although it took me a while to get a smooth rhythm going. She arched her back under me and let off all sorts of moans.

I humped away like her whole family was going to burst in at any minute. Of course, that didn't happen, but I made sure I was going to make this quick. I gave no thought about her pleasure. I just wanted my release. I think this got her off more though.

By the time I was sitting on the edge of an orgasm, I heard her say something about "blow your load" and that was enough to trigger me to cum. I filled the condom with my jizz and collapsed on her chest. She laughed a bit as did I and I pulled out of her, threw on my pants and made my way to the exit after she told me that her family would probably be home soon. I remember taking the condom with me and tossing it out the window on some country road. I wasn't sure if I could trust this one.

We chatted off and on after that, but I got a serious girlfriend closer to home soon after and all of that faded into a nice memory.