When I was a freshman in college, Craigslist personals was still a thing. I was ALWAYS on there trying to find a hookup. I met a few guys from there before it was shit down, but up until this story takes place, it was always just swapping head. One day I happened across a post from an older guy, maybe late 50s, looking for a young masc bottom. I fit the bill and I had always been on the lookout for a top to fuck me. We chatted a bit and I told him I had never been fucked, and he said hed love to be the first and sent me his address. I headed over to his place, and was a bit nervous when I got there as it ended up being a trailer park, and not exactly a nice one. I kept on driving until I got to his trailer way in the back, swallowed my fear and got out and knocked on the door. A decent looking, older man answered the door, kind of hidden behind the door and told me to come in. So I did. When I walked in, I looked around and noticed that the room was basically empty except for a couch. Then I heard him tell me to turn around, and when I did, I saw that he was completely naked. He grabbed my shoulder and motioned me down. I got on my knees, and immediately slid his soft, clean shaven cock in my mouth. After a couple of minutes of getting him hard, he told me to get undressed and he walked down the hallway. I did as I was told, and when he came back, he was wearing a condom and holding a bottle of KY. He told me to get on the couch, so I got doggy style and waited for his cock. He lubed up a finger and played with my tight hole for a bit before I felt the tip of his cock resting against my pussy. After what felt like forever, he was finally able to skip inside me. He started slowly and got me loosened up before picking up the pace a little bit. After a few minutes, he flipped me over and pinned my legs back and slid back into my hole. After so long I was finally being fucked. I loved watching his cock slide in and out of my hole. It made me so hard, and I knew then that I would have to have more. After a couple minutes he filled the condom with his big load of cum, and told me to get dressed. He definitely wasn't one to hang out with, but I was fine with that. I got back in my vehicle and drove home with my freshly fucked hole, throbbing with pleasure.