The First Time I Cheated

Alright, time to get personal with a tale from my past. NSFW perhaps, depending on how closely someone is reading over your shoulder.

It was the summer before my senior year of high school and I had been dating my girlfriend for about a year and a half. Yeah, I was that guy with the long term girlfriend in high school. Spent a year thankful just to be getting pussy at all. As I’m sure you all know that feeling only lasts so long.

The relationship was of the semi-long distance variety. She lived a town away and we mostly saw each other on the weekends. There were pros and cons, but for the most part that old saying rang true: distance makes the heart grow fonder. And hornier. As intense as those weekends could be, a young man can’t help but wonder what he can get away with in that time in between. I soon found out that it was quite a lot.

Being somewhat shy, possessing little self confidence, and no game (oblivious to that really), but industrious nonetheless I turned, of course, to the Internet. I don’t remember how long it to took me to find it, most Internet excursions quickly turned into looking at porn and vigorous masturbation, so productivity was low. But eventually I stumbled upon a certain site at which adults can find friends.

The problem with this you would think is that I wasn’t yet an adult. Minor hiccup for the determined deviant, just select one more year down on that drop down box and I was good to go. As soon as I signed up I knew I had found something special. It was like being eight in Toys R Us, looking at all shiny toys that you could possibly want, but couldn’t possibly afford.

Here’s my first real bold move: in the dark of night with the rest of the family soundly sleeping I stealthily started breaking laws. I stole my mother’s credit card, copied the info just as quick as could be, and slipped it back with no one the wiser. The fact that my parents remained none the wiser perhaps says something about their fiscal diligence.

Now, stolen credit card info in hand, my hand shook slightly as I entered it all and clicked “Submit”, unlocking the gates to unlimited casual sex with all the women I could possibly want. Only it wasn’t quite like that. There were women, some even attractive, but mostly it was a big cockfest. It served to truly shatter the idealism of a young man in regards to finding strange on the Internet.

Of course a few hundred pics of cocks randomly appearing on my big CRT monitor wasn’t enough to dissuade. Neither was the lack of responses from what I hoped were real females; I was determined. The real problem was that of all the women on there that actually were looking for quick cock, few were looking for “18 year old” cock. But I kept casting my line and eventually I got a bite.

My heart was pounding as I read her message that contained her Yahoo Messenger info. The elapsed time of her sending that message and me sending her one back in Yahoo was probably somewhere around 2.42 seconds, give or take a millisecond. I may have come off as slightly eager.

She was 23, experienced, and… married. I expressed to her how this (ironically) clashed with my morality, trying for some reason to come off as the valiant type. She assured me that he knew she did this and was completely on board and okay with it. He just thought of sport fucking young cocks as a harmless hobby. Sounded completely logical. After maybe fifteen minutes of anxious conversation she asked if I wanted to meet, just to see if we click at all.

“Byemomheadedtothegasstationbebackinabit,” I yelled as I ran out the door. I did walk to the gas station. The time was probably around 2:30 or so in the afternoon when her Jeep Cherokee swung into parking lot. I looked around nervously like I had an FBI tail or the mob after me as I got in and we took off. The small talk in the Jeep was excruciatingly awkward, but when I found out the drive to her place was only about seven minutes I would have given anything for it to be just ten minutes longer. I followed her in, thinking I must have lost my mind.

Once inside she had her prey trapped, and she didn’t waste time taking me down. Well, actually she went down. I immediately knew she was special at that moment. As I stood there in her living room appreciating that quality, I also began appreciating the giant broadsword on the wall, and the guns on the other wall, and the ammo on the table. Suddenly I wasn’t feeling as good. “Don’t worry, he doesn’t know what the fuck he’s doing with that shit,” she assured me.

Somehow we ended up in her bedroom. To this day I don’t remember walking back there, but there we were. Room was a mess, and no sheets on the bed. I threw her on it anyway. Condom? What are those? My mind was no longer in control and everything was instinct. As I railed her against the mattress my unused mind actually began to wander. She’s so so wet, I thought to myself, thankful because it was helping me last so long. I felt like a porn star.

That feeling dissipated somewhat when after blowing my young unprotected load I stood up to see a filthy puddle of fresh blood more than a foot in diameter staining the mattress. I laughed, I didn’t care, felt like I had really slain that snatch.

Of course her reaction was a bit different. Her panic was immediate and intense. Perhaps her husband wasn’t quite on board with her activities? I never found out what happened with that mattress.

Not that I stopped fucking her. I began sneaking out mosts nights after everyone was asleep. She would pick me up at the end of the drive and into the night we’d go, parking random desolate places where I received a more practical sexual education. The first time she swallowed a load she said it was like a “warm Thanksgiving turkey dinner in her belly.”

I never did tell her my real age. See, it can happen to them too! After a few weeks my girlfriend decided to move to my town, and there the fun ends. For awhile, at least…

9 thoughts on “The First Time I Cheated

  1. Leap of a Beta

    Holy shit, this stuff really happens? I too, figured that this was the stuff of legends and porn plots.

    Hell, I’m struggling to get the kind of set up like this even at 27. Though I have a lead with three either lesbian or bisexual flight attendants right now….. Hopeful is where I’m at right now.

    1. Young Hunter Post author

      I had some things going for me that I didn’t really understand at the time. Truthfully the hours spent looking on the Internet would have been better spent out in real social settings. Not that I’m regretting it.

      1. Leap of a Beta

        That’s fair. Law of limited returns and all that.

        But you saw something you wanted and went after it. For a man of any age that’s admirable. For someone underage at the time it’s a really impressive feat.

  2. littlepdog (wrong link in username)

    As a very young dude myself, all I can say is that this post has especially intrigued me. Something tells me this was a one off occurence or she thought you were hawwwtt or something. If Adult Friend Finder were that easy it would be flooded by dudes to the point it’s no longer worth it.

      1. kristinskupcakes

        oh, the laws…. Trust me, I could write a best-selling novel on ages 14-18, but I don’t want to disclose that much personal information to society… I appreciate the fact we are on the same wave length thou.

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