As this is my first submission, I'll tell you a little bit about myself to set the stage. At the time of writing, I'm 27 years old, tall, in good shape, white, and pretty much always horny. The point of me writing is to really explore, through writing, my sexual history. Until now I have experimented with lots of things, men and women, online relationships, dominance, submissive, oral, anal, vaginal, older, younger, and more I'm sure that I'll try and bring out in the stories. The first story, or first few stories will date back to when I was 18, out of high school. Also, my name's Sam. We'll see how it goes!
The beginning:
I was a virgin all through high school, including oral, and though I had made out with girls and 'fingerbanged' them as we used to say, nothing ever went further than that. I stuck to girls back then, though I was definitely curious about guys at that time as well.
The summer after HS graduation was fun - before we all left for college, just hanging out, going to parties, drinking, smoking, doing all the things an 18 year old guy would do. One party, in the middle of the hot summer, I finally had sex (with a chick). I lasted all of about 1 minute. I felt really bad (though I had expected this) and went down on her. I remember clearly thinking, 'holy shit, I love this!' I loved how it tasted, I loved her moans, I loved the fact that I was actually giving her pleasure. A few minutes in, I was hard again. Put another condom on, and fucked her. This time I lasted a little longer, though not much :(. Anyway, that was the first. Nothing else happened that summer, with her or anyone else. In August, it was time to head off to university. Leaving home was tough, but I was excited. I knew it was going to be a fun experience, and sex was on my mind - lord knows i'd watched enough Girls Gone Wild to have a vivid imagination with regard to hot college chicks.
Unfortunately, I didn't have as much luck as I'd hoped in the first part of school, but I did make an important discovery. In getting to know my roommates, one of them randomly mentioned craigslist as a place to get some cheap furniture, and joked about the casual encounters section. Believe it or not, I had not heard of this, despite having spend countless hours on the internet, my hard dick in hand. this was a real revelation.
I would browse CL when my roommates were out, in all of the personal ad categories. The most activity tended (and still is) on the m4m side of things. That was exciting. I had always been curious, but had never acted on it. I started communicating with a few guys, all older, all looking for 'College freshman' or 'College aged guys'. I guess school being back in session was a signal that young, open minded college guys were in town. It was true then and it's true now - I now use the 'college school year is starting' to turn the tables and have fun with younger guys (but that's a later story).
Anyway, I started communicating with a few guys, and a few stuck with me through long email chains. I had never done anything with a guy, so those wanting to meet up right away were out. I ended up sharing pics of myself with these guys, no face pics, always just of my dick, ass, body, etc. They'd send me pics too, which I'd jack off to. One guy really struck me as a good one - his name was Mark. He relayed the story of his first gay experience - freshman in college, older, local guy brought him into the fold. He told me he'd like to 'pay it forward' and help me gain experience. I ended up jerking off with him on cam a couple times, which was wildly fun. The thought of another guy jerking off to me , cumming at the same time, albeit digitally, was awesome.
After a few weeks of back and forth and numerous cam jackoff sessions, I ended up biting the bullet and agreed to meet up with him. He lived close to campus, easy walking distance from my dorm, in a condo complex. I was familiar enough with the area, and felt safe enough. It was a Friday night - all done with classes for the week. It was still not quite fall, and at 7 PM it was still light out. I was really nervous - I took a few shots of cheap (cheap) vodka (all the rage back then) to calm my nerves, which did help, and walked over. I texted him when I got there. he came to his door, which was on the second floor of his section of the complex, and waved down at me standing in the parking lot. I took a deep breath and climbed up to him.
While the details of *exactly* what was said are fuzzy ~9 years later, here's how it went:
Mark said, in a cheery voice, "Hey man, what's up?" He had a Heineken in his hand and gestured it toward me, "Want a beer?"
"Sure," I said, voice slightly cracking with nervousness, "that would be cool."
I crossed the threshold of his door, walking behind him as he made his way to the small galley style kitchen to grab my beer. His place was clean, with a nice living room complete with a black leather L shaped couch facing a media center with a big flat screen TV. Directly back from the front door and through the living room was a sliding glass door leading to a small patio overlooking the interior of the complex and the community pool.
I of course had seen mark on cam, but he was a good looking guy in person, too. He said he was 45, but he looked younger, maybe 35. He was wearing dark blue jeans that weren't tight, but fit well enough to show off his toned legs and slim waist. He was about 6'2, and likely about 180 lbs - in great shape. He was wearing a white patterned dress shirt, tucked in, like he'd just come from the office on casual Friday.
He popped the cap on the beer and handed it over to me. I immediately took a sip.
"How's school going?" He asked as he led me into the living room. He sat down and I followed suit, sitting a couple feet away from him on the couch.
