November 22, 2008 - Chris

Okay, so let me put it this way -- I have never had such passionate and honestly real sex before. I've only had sex a few times before, but the guys just never had the passion I was looking for. Yeah, you might be thinking, "well, not all guys are in it for the emotional aspect". But tonight was different.

Like usual, I took my daily late-night screening of the listings for cute guys on Craigslist. After unsuccessfully e-mailing away at the twilight hour of 1 am, and being turned down by a few because I wasn't their "type" (whatever the hell that means), I eventually got fed up and decided to post an old ad that I had saved for another time.

Without hesitation, I posted my AIM on the listing as an addition. Not a half hour later did I begin getting quite a few IMs popping up on my screen. Long names, short names, medium-length names ... all kinds. But one was special ... Chris was his name ... and he was my age, 18. The way he spoke over the IM was just like a person of our age group, so I knew I wasn't being duped. When I asked for him to send a pic, he sent two (one of him and one of his cock). He wasn't huge, nor was he small ... but I will say this, he was freaking hot!

We talked maybe for 15 minutes before deciding we were going to meet. Mind you, he found me. This is the first time I've been contacted by someone else, rather than me finding someone else. Anyhow, a little over 45 minutes passed before he got to my place. It was just past 3:00 when he called on my cell telling me he was a little lost -- turns out he turned onto the wrong street, the one before the Wawa, not after.

Eventually, he found my place and came inside. He looked a little shy, but that was okay -- I was completely freaking out! He was toned yet skinny, like me, with a slightly darker shade of skin. Those chocolate brown eyes could turn even the straightest of men on. His dark curly locks shone in the dim light of the fire I had set up in the wood-burning oven. After waiting a few moments, we got down onto the makeshift "bed" I had created by taking a few blankets and pillows from my own bed and laying them out on the floor.

Before we got down, he told me, "What do you want to do? You're the expert." I'm the expert? Please, I've only had sex four times before this. If anything, you'll teach me, I thought.

We started by feeling each other out -- I felt his slightly hairy chest while he worked my dick with my pants still on. Before I couldn't hold out much longer, I undid his belt, unbuttoned and unzipped his tight-fitting jeans, and pulled out his cock, beginning to slowly stroke it. At this point, he asked me if he should take off his shirt. I said yes, and not long after, we were making out. As our tongues wrestled in each others' mouths and our hands slid over each others' bodies, my shirt and pants eventually came off as well as his jeans, leaving us both vulnerable in our socks.

Anyway, won't bore you with the many details, but will say a few points to remember. He brought lubricated condoms with him, and for the first time I got a fucking hot pounding up my ass. This was after trying to figure out whether the condom was fitting on his dick right ... or whether it was open all the way. A little levity to level the intensity. Of course, I had never known what a cock felt like in my ass until he fucked me; only my own fingers. But fortunately, I was somewhat used to it.

By the time he was done fucking me, he had ejaculated into his condom and then slowly slid it off. After he finished, I put on a condom and asked if he was ready. He shrugged and got into the same position I had been in -- only one problem: either my dick was too big for his ass, or his ass was too small for my dick. After trying for about a minute or two, he just said, "I guess anal isn't for me" and laughed. That's okay, I wasn't offended or anything.

The majority of the time left was continuing to make out heavily and touchy-feely junk. Then he started jerking me off and sucking intermittently between his strokes. I knew I couldn't hold back much longer. It took a good five or so minutes for my cum to start to boil. After that, we held hands as he continued to jerk me off, squeezing hard and soft until at least five thick streams blew out of my cock and onto my chest. We kissed for another minute or so and then he told me it was a little past 4 and that he needed to go since his mom would be home at 5 and she didn't know he went out. "During the week, yes," he said, "But not on the weekends" and laughed.

I wiped the cum off my chest and dick with a bunch of tissues, and got dressed again. Once I was dressed, we shook hands and I walked him out to his car. At about 3/4 down the driveway, he turned back around and we kissed two quick times before he went to his car. It was that that made my night, and also proved to make this night different than any other I've had with a guy before. I said, "Drive safe" as he got into the front seat. "Will do," he replied.

Then he made a u-turn and drove away. I hope I'll be able to see him again sometime. There was really a chemistry that I had never felt before with him. Probably 1: because we're both the same age; 2: because we were both extremely horny; and 3: because not every man is the same sex-driven pig that I used to be. Some have emotions (me now included in that category) as well as Chris. God, I hope I see him again.


THE ABOVE IS A TRUE STORY FROM TONIGHT'S HAPPENINGS. Feel free to post comments.