(This is a true story with all names changed and conversations as close to my memory as possible)
Throughout high school I had known I was attracted to guys but continued to pretend like it wasn't true. I was obviously into women and had been with them before, yet when I sat down by myself to watch some porn I would always find myself gravitating towards the gay sections of the websites. I had a very slender build, and my red hair was long enough to rest on my shoulders. Occasionally older men would hit on me at the gym and it always got me excited. The concept of being bisexual had not yet occurred to me and so I really struggled with my own feelings. By the time I had graduated my inner conflict and the tantalizing curiosity of being with a man had me at the end of my rope. I needed to get an answer on how I really felt.
I decided the best thing to do was to try and find someone to hook up with that didn't mind me being curious. Little did I know at the time that curious skinny twinks were in high demand. I ended up making a post on the personals tab of Craigslist. It said that I was a young skinny guy looking for my first experience with another man. I was mainly interested in giving head and was still very much on the fence about taking anal. In hindsight it was a crazy and dangerous thing for an 18 year old to have done, but luckily nothing horrible happened. Instead, my email began to flood with messages from horny men.
Most of then were simple messages with little more than a "You lookin to fuck right now?" Or something else along those lines. I had a few back and forths with some people but most of them were more than 45 minutes away by car. I was definitely not looking to drive across the state for a first hookup and so I started to lose hope in the whole deal. That was until I received an email from someone in the same town as me. He was a couple years older than me and had a place with some roommates. It sounded perfect and I was very glad that this guy was willing to plan a date and time instead of just pushing for me to rush over at that moment. We planned for the next day which was a Saturday and in the early morning. I had told him I was currently only interesting in giving head since I wanted to try it out first and he seemed to be totally fine with it.
When the time came I told my parents I was going to get an oil change in my car and headed towards this guy's house. I pulled into an empty driveway and started to get nervous that nobody was home when a head poked out the front door and he called me inside. I stepped out of my car and nervously started walking towards the door. I could feel my legs shaking and my mind was racing thinking about what was going to happen once I went inside. The house was old and rustic but had clearly been getting worked on as of recently. The faint smell of fresh paint permeated the air and I could see plastic wrap on some of the walls still. The man introduced himself as Eduardo, but told me I could call him Eddie.
Eddie was maybe two inches taller than me and had a good 40 pounds on me. He was Puerto Rican which was common in my town. He was wearing a baggy white t-shirt and some black basketball shorts that went down to his knees. We stood around awkwardly making chit-chat for a couple minutes before he finally made a move. He placed a hand on my lower back and slowly slid it up underneath my shirt. His fingers caressed my back which made it feel like electricity was coursing through me. I shuddered and giggled a little which he must have took as an invitation to go further. Not that it wasn't.
Eddie took me by the wrist and started to lead me through the house and into a bedroom on the first floor. It had not a lot of decorations and there were still cardboard boxes filled with things. I figured they must have just recently moved in and he was already checking out the local hookup scene. Once we were inside the room he closed the door behind him and the reality of it all set in for me. I had never hooked up with someone before, especially not another man. My only experiences with sex were in committed relationships. Having just come out of one only a couple months before though made me especially horny and so I wasn't all that scared. At this point I was nearly shaking with anticipation.
While I was taking in the room, Eddie took the opportunity to sit down on the bed and look me up and down. "You're pretty cute you know that?" He asked in a genuine sounding tone. The flattery instantly made my face turn red and I couldn't help but crack a smile. He had me in the palm of his hands already and I was pretty sure he knew it. He flashed a toothy grin and clapped his hands together.
"Enough messing around though, why don't you start to undress for me?" He said sounding pretty commanding. The sudden shift in atmosphere caught me off guard, but the way he spoke the words made me feel like I simply couldn't deny his request. I took my tight black t-shirt off and let it fall on the floor before looking back to see Eddie staring intently at me. He appeared to be rubbing his cock through his shorts as he watched me strip. "Keep going boy." He ordered with a huge smile across his face.
