Of Course, Craigslist!

I was a horny high school boy, looking to lose my anal virginity. Unfortunately, living in Southern Maryland AND in a Catholic household did not provide the best outlets for such activities. I nearly wasted away, trying to find some sort of way other than masturbation for release. In the end, I resorted to gay cruising sites. I nearly had my first with a 31-year-old in a car, but I got too scared, and told him of my virginity, and walked home. (Hookups needed to be within walking distance because I could not drive.)

The weekend after I got out of school, I answered a Craig list ad for a college kid in Charles County. I responded, and in a few hours, I got a reply. We texted for a couple of hours, until I finally told him the place and time where we should meet: a park at night at about four in the morning. I waited for my mom to fall asleep, before I snuck out of my house and walked all the way to the park, waiting for this guy.

He got lost, and so I had to nervously stand outside the park for ten minutes, before I saw him pull up. He was much more attractive in person than in the pictures he sent me. We drove up to the park, and ended up in a basketball court. In order to cool each of us down, we took a hit of weed. That was about 5 minutes.

Then he approached me. I didn't know exactly what I was doing, because I had never made out with someone, let alone an experienced college student. He made the first move, and slipped his tongue in my mouth. We made out for a couple more seconds, until I took his shirt off. A little more, and his shirt was off too. I made little pecks into his neck, and slid all the way down his body, kissing the nipples, the treasure trail, before finally pulling down his pants.

There was a penis in my face, and it wasn't mine. I looked at it, confused, before I felt the need to take it into my mouth, careful that my teeth not brush the sensitive skin. He moaned, prompting me to swallow more. It got to a point where I could not take it in anymore; tears coming to my eyes, gag reflex reacting, I was a few seconds from embarrassingly vomiting all over my first time. However, I took a deep breath, and sucked as hard as I could. I went up and down, making the shaft as wet as I could for the next part. He took my hand, and placed it onto the shaft, and I jerked it while swallowing it. Although it was only seven inches, it was still my first time, so I wasn't too worried.

I kissed my way back up his body, and met his lips again, tongues intertwining like they should never leave. He then kissed down my body, stopping just above my penis, before pulling my pants straight down and planting a wet kiss on it. It made me jerk back a bit, but not enough for him to question my virginity. He put his wet, warm mouth closer to my skin, down my shaft, and it felt heavenly. That took about two minutes, before I nearly cummed. He stopped before that moment came, and reached for the condom.

Unfortunately, I was not experienced enough to lube and prepare myself before it, so he was basically going in dry. He tried his best to lube it up with his spit, but it was not well done. I felt a huge stabbing pain at my prostrate, and I knew that someone was finally inside of me. All four years of confusion led up to this. He grunted, thrusting into my body harder. I panted, grasping for the air that was continually fucked right out of me. He slipped a couple of times, but his firmness was very welcome inside my butt. It pounded further, and further...

Until I sprayed all over the court beneath me. I fell to my knees, as did he, and he continued to pound me as I made out with him above. After about 10 minutes, he pulled out, threw the condom away into the woods, and pushed my head down. I sucked his dick in, my second time, and went as fast as I could to give him the same awesome pleasure he gave me. I moved rapidly, as his legs began to tremble from the movement. Eventually, I switched to my hands and he cummed all over me. I wiped it up with my discarded shirt, and returned his. He drove me home that night, and I was able to get back upstairs to my room before the lights came on in my mother's for her daily routine.

I have yet to see that guy again. I do not even know if I want to. How weird is it, when you don't even know your first time's name?