[M]y first time cheating

I’m honestly not sure when it got out of hand. When it got to the point where I’d do just about anything for sex. When the risks became a part of the draw, and it didn’t matter if I was in a relationship, or who might be asleep in the next room, or if anyone had a condom. At some point, I just knew that I needed more sexual activity than one relationship could really provide me with, and cheating became just part of the deal. Or casual sex in general, really. Even when I was single. I just really enjoy fucking a stranger. One of my top five favorite things. Right up there with Blood on the Tracks. I’ve mourned few deaths in my life like that of Craigslist. A haven for the casually minded individual, but somehow cheating was always just… hotter. I’ve done it for years, and I’ve done it successfully, and the worst part is that I fucking like it. I’m good at it. I’m not sure if anything gets me off like fucking someone I shouldn’t. I wish it weren’t that way. Honestly, I do. But here we are.

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I think the first time I cheated was in college. I had been dating this girl for a while. We had a cute little apartment together, close to campus, we had a dog named Martin Sheen who I dearly miss to this day. Things were generally pretty good, I guess is what I’m saying. But at some point I must have drifted to craigslist, the call of casual encounters becoming too much to resist, because that’s where I met Sara. She lived in the same town, we went to the same college. Even better, she was also in a relationship. We messaged on AIM for a few days, when that was still a sentence that made sense to people, before we finally met up one Saturday at the library up on campus. Sara said she knew the perfect spot. I told my girlfriend I was gonna go work on a paper, kissed her, and off I went. I rode my bike up to campus and got to the library just as I got a text from Sara telling me where to meet her. It was some multimedia room up on the 4th floor. I was so nervous walking up. My heart was pounding. But she was right, it was the perfect spot. Here was this dark, secluded hallway with a bunch of multimedia rooms. I opened the door and there she was. We didn’t really waste much time as I recall. We just started kissing. Hard. Like really going at each other fiercely. Then she got right down on her knees and gave me the kind of blowjob that shakes the very foundations of a man. I still look back fondly on it. She was great at giving head. She blew me fully and completely in a way that few have recreated over the years. She smiled and swallowed my load and I knew I had to have more of this girl. We made out a little more after we got cleaned up, and I pinned her from behind down over the table… I slid my hand down the front of her denim shorts and she was soaking wet. I fingered her there as she kind of grinded on me, reaching behind to feel how hard I was. I thought I’d see how far I could take it so I started pulling down her shorts… then her panties… then my pants… then my underwear… until my bare cock is grinding on her bare ass and both of us are just waiting for the other to make a move. The problem was nobody had a condom. I certainly hadn’t expected things to go quite this far the first time we’d meet, hell, I didn’t even think I’d get a blowjob. I don’t think she expected it either, and being as this was my first cheating experience and I hadn’t yet completely abandoned any form of rational thought when it came to fucking, we decided we’d wait until we had a condom. So we did wait. Until the next night, when she picked me up from work and we fucked in the woods of a disc golf course. I saw Sara a few more times after that. Each time, meeting for this passionate, lustful, incredible sex, then both of us going home to our respective others. I don’t know for sure, but at some point I think the guilt got to Sara. She quit texting me, responding to facebook messages. I think she ended up marrying the guy a few years later. It was kind of a bummer at the time, but looking back on it now this is like the early days of the sport for me. Like when Tiger picked up a club for the first time, when Dirk first shot a basketball, I began to hone my skills. I learned how easily I could pull it off. How easily I could hide it. How and where to find like minded individuals.

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Worst of all, I knew I’d do it again. Sara was just the beginning.

Source: reddit.com/r/gonewildstories/comments/befwbx/my_first_time_cheating