Okay, So I basically posted this in another thread earlier, but it applies here, too. I'll go into more detail here, though.
I was 18 when I took my first anonymous load. Also, It was my first time doing anything with anyone. I had just moved into the dorms at college for my freshman year and decided I would explore and see what there was to do around campus. After methodically working my way back and forth, up and down the streets on the north end of campus, I came to a building that looked interesting. It was a club called the Carousel, and was 18 and up. "Great!" I thought, and I paid my $2-3 (or whatever the cover was) and went inside.
Turns out, it was a gay bar that was pretty much legendary in town, but I was new and had no idea until I walked inside. I followed a crowd up a double spiral staircase, watched my first drag show, and went back downstairs during intermission to see if I could talk someone into sneaking me a drink. That's when he found me. I got a tap on the shoulder and turned around to find a really hot frat-type guy (probably a junior of senior, not sure). He said he saw the big "X" on my hand and said if I wanted some booze, his apartment was just a couple of blocks away. I didn't even know his name, but I said "Sure!" Honestly, I was so naive and sheltered growing up that I didn't even have thoughts of something like this going down an hour earlier.
I was already somewhat confused as to where I was except for knowing the general direction of my dorm, but still, I followed him out the door, down a couple of streets and through an alley to the back door of an old Victorian that had been cut up into apartments. We climbed a flight of stairs and went inside his apartment, then he went to the fridge and he grabbed us a couple of beers. We sat on the sofa and talked about nothing, but he caught me looking at his bulge. He looked at me and asked "you want to see it?" I don't think I made a sound, but I remember nodding. He stood up, unbuckled his belt and dropped his shorts and boxers to the ground. It was the first time I had seen a hard dick other than my own. It was perfect. He sat back down next to me and said I could touch it if I wanted... I didn't even have to think, I just reached over and started slowly jacking him. He wasn't huge, probably about like mine.... 6 1/2 or 7 inches, medium thickness, cut... pretty average, I guess, but I was in heaven. Thats when he slid his hand down the back of my shorts. I knew he was trying to reach my asshole, so I shifted to give him better access. As soon as his finger touched my pucker, I knew what I wanted.
As I said earlier, the thought of hooking up that night hadn't even entered my mind. If it had, I probably would have bought some condoms. I think he knew I was unprepared, because he asked me if I had one. When I told him I didn't, he said "Damn. All I have is lube." He just kept fingering my hole for a few minutes while I jacked him, knowing he was turning me on. Eventually, he pulled is fingers out of my ass and looked me right in the eyes. When he asked if he could fuck me raw, I said that was fine. After we had been fucking for a while, he asked if I wanted him to pull out. I told him I wanted his cum in virgin ass. That did the trick. I had told him I was inexperienced because I was too embarrassed to tell him I was a virgin. When he realized what I was saying, that he was taking my virginity bare, he unleashed the biggest load I've ever had. I never knew getting bred could be so hot until that night. Honestly, I had never even considered going bare before, because in every other aspect of my life, I avoid risk.
Eventually, I found by way back to my dorm with a huge smile on my face and a leaky ass full of his anonymous load. I never knew his name, I never saw him at the club again, and as hard as I tried, I could never figure out exactly which house was his.