Craziest one was my first one about 7 years ago. There was this bar I was a semi-regular at that was having some special event that a lot of people would be going to. My roommate at the time was out of town and I knew in the back of my mind that this meant I could stay out all night without him ever finding out (I liked maintaining the good boy persona). The idea of a one night stand was on my mind the whole night. Sitting at the bar I was playing with the latest iPhone, which I had received 2 days before the official release date. The girl next to me noticed it was the new iPhone asked me to see it. I immediately put it in my pocket afraid that she or somebody else might try to steal it. She then playfully started putting her hands in my front pocket, she moved her hand past the phone to grab onto my junk! It was turning me on and I was afraid about getting a public boner so I pulled out the phone so that she would stop. It worked but after a little while she wanted to leave and go back to her place where she said she was having a party. Well, it wasn't really a party, it was just a few of her friends, which didn't stay long. She asked if I wanted to watch a movie so we went downstairs to her bed. We really did watch a movie and I made no moves towards her. She became visibly frustrated by this and whipped out this large rabbit vibrator and started going to town on her own, saying something like, "if you're not going to fuck me, I'm going to take care of myself." I just laid there in disbelief and bewilderment. Finally, I couldn't take it anymore and started caressing her breasts. She continued with the vibrator and started massaging my cock through my boxers. I was already extremely aroused at this point and she quickly pulled off my boxers and got on top of me. Before I even knew what happened, I was deep insider her, without a condom, which made me pretty paranoid. I asked her if she had protection. I stupidly forgot to bring my own. She said that she's on the pill and not to worry about it. At this point carnal desire took over and I let her ride me until she came. She would then get off, nod off to sleep for a few minutes, wake up, start stroking me, ride me, cum. This repeated so many times I lost count. I was able to keep going because she always came before I could. Eventually the sun started coming up and she said it was my turn to cum. I got on top, missionary. She was still insanely wet and she kept yelling out "harder! harder!". I slammed into her as hard as I could, the bed ramming into the wall. I had effectively been edging all night so I knew I was going to cum really hard. Again, carnal instincts took over and with one last thrust I came deep insider her for what felt like eternity. Completely spent, I just laid on top of her, still inside, for probably 10 minutes, my cum pouring out as I softened. Soon after that she called a taxi for me and I never saw her again. We did text a few times and I got myself tested at least 3 times within 9 months after that. I look back at it as both the best and the worst sex I've ever had. The best being for what I described above and the worst because it was so reckless of me.