I walked up the front stairs of my apartment porch, and peeked into the windows. The lights were off, meaning that most likely none of my roommates were home yet, so I opened the door and entered, and became a little less nervous.
I had just left a friend's birthday party, earlier than everyone else. I slipped out quietly while everyone was too drunk and excited to notice. My mind and body were humming, since I was still pretty buzzed myself. The party had been fun, but no different than any other. I could tell everyone was planning to stay out and celebrate for a lot longer. Normally I loved doing that too, but tonight was different. Whether it was the drinks or the culmination of thoughts I'd been having more and more recently, I was feeling incredibly horny.
Over the past year or so, I had found myself getting more curious about what it would be like to have sex with a guy. I didn't really consider myself bisexual (not yet, at least), but I noticed that as I watched porn I enjoyed imagining what it would be like to be in the girls' position -- to be on my knees worshiping a nice cock, or being pinned down on the bed and having my ass fucked.
It was the summer between my junior and senior years at college in Boston. I was staying in town to take some necessary summer classes, so I subletted a room at a friend's apartment in the Allston neighborhood. As I walked through the apartment I passed through kitchen and pulled myself a beer out of the fridge. I popped the tab on the can, paused, and looked and listened one last time for any noise. All the bedroom lights were out -- no one was home, or if they were, they were already passed out for the night. I didn't want any of my roommates to find out what I was doing -- it was awkward enough figuring out my sexuality on my own. I walked into my room, and turned on my laptop as I took a nervous sip of beer. I had finally convinced myself to give this a try, and I didn't want to lose my courage.
Soon I had Craigslist personals up on the screen. This was something I'd done many times before, but usually I just read some m4m ads, fantasized about answering them, and masturbated before falling asleep. Tonight I was determined to follow through, to at least try to find someone patient and fun to explore with. I replied to a couple of ads for guys that seemed to live nearby, but I either got no response back, or really creepy, aggressive, off-putting ones. I wanted to hook up, but I wanted to feel the guy out first, and not just blindly meet up with a creep.
After a while, I was about to give up on the night, when I noticed a reply had come in from one of the first ads I responded to that night. The guy had written an ad describing himself as a bisexual guy in his early 30's, a who was a bit stocky. He was just what I was looking for, since I found myself fantasizing most often about older, heavier guys. I certainly wasn't an athlete or a model myself, being a few extra pounds above average. In my original email to him I had described my curiosity, and how I was eager to lose my virginity to a guy like him.
His reply read,
hey dude, nice stats and pics! i'm jim. i'm def interested in playing tonight if u still are. u being a virgin is not a problem, i'd love to help teach you the ropes. like i said in my ad i'm looking to top for a guy like u. i'm patient and we don't have to do anything u don't want to do. ive attached my pics too. let me know ;)
Jim definitely sounded like the type of guy I fantasized about. I replied with a few more pictures of myself that I took from my laptop, and tried my best to flirt about how excited I was to meet up. I told him I needed to travel to him, since I lived with roommates and I didn't know when they would be home. His original ad said that he lived in the same general neighborhood as me, but as we talked it turned out that his apartment was only two blocks away from mine. It was as good a sign as any that this was the night I was meant to give in to my curiosity. After some nervous hesitation, I replied that I would meet him at his apartment in about half an hour.
I chugged the remainder of my beer, and hopped in the shower to freshen up. As the water flowed over me, I took some time to trim my pubic area, and shave around my asshole. I wanted to make sure I felt sexy for my first time. While rinsing, my hand worked its way to my ass, and I fingered myself for a minute in excitement.
After drying myself off, I threw on a loose t-shirt and some basketball shorts with no underwear underneath. I could smell the shampoo drying with my hair, and I smelled fresh. Still riding my buzz, I took a deep breath, opened up the front door, and walked out into the cool night.
Even though Jim's apartment was only a short walk away, I was nervous and excited, so it seemed like it took an eternity to get there. I could feel adrenaline pulsing through me as I walked beneath the calmly rustling trees. When I arrived at his place, I was surprised to notice that the building was one of the red brick town houses that I passed by almost everyday on my way to class. He said he was on the first floor, in the first apartment to the right. After hesitating at the door for a moment, I took a deep breath and rung the bell to his unit. It couldn't have been a long time between me ringing and him answering, but at the time it seemed like an eternity. What am I doing? If there was any time to turn around this was it. But my horniness won out.
Soon front door latch buzzed, and the door unlocked. I walked into the harsh fluorescent-lit hallway, and saw the door to my right unlock and hinge open just a crack. I walked up to the door, and gave it a little tap as I pushed it open. On the other side was Jim, silhouetted by a lamp behind him in an otherwise dark living room. He was just as he described himself—about 10 years older, with a little bit of a belly, shaved bald head, and a stubbly, attractive face.
"Hi," he said. "You're cute."
Jim took my hand, led me inside the apartment, and closed the door behind me, locking it with a click. He started to gently run his hands over my chest, and then around my body, working his way to my ass, giving it a little squeeze. Then he leaned in towards me, brushed his lips against mine, and pulled me into a deep kiss. I had never kissed a man before, but it felt surprisingly natural, even in my nervous excitement. He pressed his lips to mine with a forceful masculinity, his tongue pushing its way into my mouth. I relaxed my lips and kissed him back, finding myself turned on by the rough feeling of his stubble against my face.
After a few minutes of making out just a step inside the front door of his apartment, I pulled back, sucking on his bottom lip.
