Craigslist Descent

Disclaimer: Fiction

It started a couple of years into my marriage. Yes, she was the love of my life when we first met, but fast forward two years of boring and at times bitter cohabitation, and by that point, sex had become more of a chore than anything else. The fun and sexiness of the relationship had completely died. This is when i started exploring into my bi desires.

After catching a few text messages on my wife's phone of a guy telling her how great she was in bed, I finally came to realize that she had been cheating on me for quite some time and the texts had been going on for months, I just never had the guts to ask who it was.

Finally, one day after spending the night alone as my wife left to go out with her "friends", I decided to check out personals on craigslist just for the hell of it.

I started looking at the women for men personals.. they looked mostly like cute little whores of all sizes, shapes, and colors. It was hot to read and watch but I couldn't quite bring myself to cheat on my wife with a whore.

I went on to look at the men for men categories as those posts looked a lot more genuine. Some of the posts were extremely hot and had pictures of ass and hard cocks. One of them stuck out as he claimed to be located close to a mall nearby. I decided to respond on the post and he replied and we started texting. we agreed to meet up at a hardware store parking lot. An hour later I drove up to the lot, nervous but excited at the same time. He was already there and motioned me over to his truck.

I climbed in, we shook hands (awkward) and we started talking about our likes and dislikes. To my surprise, he was about twice my age in his 60's. He drove off and parked in a quiet private driveway and asked me if i wanted to see his cock. Being horny and convinced of what I wanted to do, I said yes. He said I would have to let him play with my ass first to get him hard.

I was hard as a rock and would have agreed to anything at this point. he reclined my seat all the way down and I shifted a little bit, first facing the passenger door, and then I turned completely face down on the passenger seat so he could feel my ass, and he aggressively pulled my pants and boxers all the way down to my knees. he squeezed and felt my ass up for a while and then spit on it and started pushing a finger inside. I buried my face in the headrest and jerked around a little in pain as he started finger fucking me harder and faster while calling me a whore.

"You like being dominated by a REAL man you dirty little whore?" he asked. The real answer to that was no, but I was so enjoying the stimulation that all I could mutter was yes. After spitting on my asshole some more and fingering me some more he jumped over me, pulled his pants down a little bit, and started penetrating me with the tip of his cock. I was thinking to myself -what am I doing? I'm about to get fucked up the ass in a truck by a complete stranger- the passion was overwhelming... and he started pounding away at my asshole.. slow at first and then he picked up the pace. I was adjusting and moaning as he held me down with both his arms pushing down on my back and fucked me in the ass mercilessly. A few minutes later, he grabbed my hair, pushed me down harder, and said 'i'm going to fill your ass with my cum' and I could feel my ass being pumped with shot after shot of cum until he finished and got off.

I asked if he had some tissue I can use to clean myself up and he said no so I just pulled my boxers and pants back up with all that jizz oozing out of my asshole in my ass cheeks and running down my legs. It was pretty gross but I was ready to get out of there. He dropped me back off to my car, said thank you, and drove off.

As soon as I got to my car, I took my cum-soaked boxers off and put them in my pocket. As I got home I realized that I didn't cum yet and was still hard. I laid down in my wife's bed, pulled out my dirty boxers, and sniffed the stranger's cum on them and fingered some of the cum still left in my asshole to taste. I came harder than I ever had jerking off.

This was the first of many craigslist hookups.