Met up with 3 guys from craigslist this last week and a half, one of who fucked me bareback for the first time. Prior to this month I've only had 1 other semi-anon sex experiences and the whole process is still pretty novel to me so this is undoubtedly tame compared to many. Saw one guy twice, the first time he picked me up in a really roomy minivan and was wearing a nice dress shirt and pants, looked to be late 30s/early 40s. We drove around looking for a spot to park and found a Staples parking lot that was virtually empty. He parked in one of the far corners and we got in the back. I laid down and he took me into his mouth. After a while he flipped me over and rimmed me for about 10 mins before telling me to cum in his mouth. Never touched himself or took off a single article of clothing the entire time. He emailed me again a few days later asking to meet up. I was expecting a something similar to last time since we didn't discuss details beforehand but when I got in his car he told me that he had a motel room so we headed there. On the way he told me about a cabin he has about 6 hours out of town and wanted me to stay there for a few days with him, I told him I was too busy with school but in reality found the offer more strange than appealing. Images of a skull collection labeled with "craigslist people" or something flashed before my eyes. When we got to the motel room he asked me to take my clothes off and get face down on the bed. Started rimming me immediately and got really into it. After a bit he took his clothes off and I was able to observe his figure. He had a big belly that I hadn't noticed before while he was clothed, and was large in general. He started sucking me and running his tongue from my balls to my ass. He stopped playing with me abruptly and moved over to my head, and put his cock in my mouth. It surprised me because I took him for somewhat submissive based on his emails, combined with the fact he didn't touch himself or get naked during our first meeting. He was only in my mouth for a minute or two before going behind me again, and I was expecting more rimming. Instead, he slid a slimy finger in my ass. When I turned around I saw him put what I assume was a "travel size" bottle of lube on the bed that he must have produced from his disembodied pant's pants pocket. It felt good and didn't hurt, so I let it continue. Eventually he said that he wanted to fuck me. I considered it for a moment and asked if he had a condom. He didn't, but having his fingers already in my ass probably influenced my judgement and I said it was fine. His cock was modest and uncut, about 5 inches, and it took 4 or 5 minutes to work it into me. We went from doggy style to me flat on my stomach, his big gut was kind of crushing my back and I found it hard to breath while he was fucking me, which was kind of hot in a rough sort of way. I felt his thrusts getting faster and unintentionally tensed up in anticipation. It wasn't immediately obvious when he came in me, but I could see some of his cum on the ridges of his cock head when he pulled out. The spot underneath my dick was soaked with precum, and when I turned over and he blew me and swallowed my load again. It was exciting overall. Disappointed that I couldn't actually feel anything when he came but I loved the kind of primal feeling to it, and definitely want to start getting topped raw.
