When I was 18 or 19, back in 2010, I lost my anal virginity to a Craigslist Hookup. I had already been with a few women, but this was my first time with a man. I found a slim, 30ish blond man with glasses to come over and teach me. First I remember stripping down to my boxers and letting him massage my back for a little while. After about 5 minutes, he pulled my boxers down and started to rub my ass. He put a finger inside of me. I was so nervous that I tensed up around his finger, and it hurt a bit. I winced and took it, because I wanted it. I offered to 69 so I could suck his cock, so I rolled on my back and he straddled me and took my cock in his mouth. He lowered his cock down into my mouth and I immediately choked on it. I slobbered all over his cock, pushed him off of me a bit. After I caught my breath for a few seconds, I let him trust back inside of my mouth. We sucked each other off for a few minutes, before he lifted up and put his shaved asshole just about my mouth. He would not quite let me reach it with my tongue, holding me down with his legs, as he slipped a condom on. I was the bitch here. Only my ass would be touched. I got on my hands and knees and put my face down. He pushed his cock to my asshole. He wasn't very big, 5 inches probably, medium girth. But, when he pushed inside of me, it hurt so bad. We probably didn't use enough lube at first, because I remember my asshole rubbing against that condom. He pushed his whole cock inside of me on the first thrust. I gasped in pain, and he held his cock all the way inside of me. He asked me how I was doing, and I said it hurt. He pulled out some more lube, pulled halfway out, and poured it on his sheathed cock. He started to fuck my sore, raw ass, and I took every pump. It hurt a lot, and I loved the pain, but it wasn't pleasureable in the way anal is for me now. He certainly wasn't paying attention to my prostate. That's what I deserved though, because I was his bitch that night. He reached down and jacked me off. I came almost right away, but he kept fucking me some more. After I came, the cock in my ass hurt even more. Every thrust was so intense. But, I held on to the bed and took it until he finished. He threw his condom out in my trash, and I asked him to leave. We never kissed. My ass hurt for days, and I was addicted.