My name is Julian, but I go by Jules. At 18 I was rather unsure of myself. I was a shy, nerdy, gamer kid insecure/if not unaware of his sexuality. For the most part, I went unnoticed on the fringe of high school society. My small size didn't help me gain any attention either. I was barely 5'7" and 130 lbs. I had shoulder length brown hair, blue eyes, and a baby-smooth face. At the other end of spectrum there was DJ. He was the popular star athlete and he was absolutely built for it. The football roster had him listed at 6'1 and 200lbs, but his muscular stature made him seem even bigger. He was handsome and his kind, but mischievous, smile was award worthy. By 18, he was more mature looking than a lot of our teachers. Of course I knew who he was. Everyone did. But, I doubted he knew who I existed - until we became friends via the internet.
Our relationship started through online video games. When we talked while we played together, he showed genuine interest in me. We clicked. At first the relationship was strictly platonic. However, my loosely held notions of heterosexuality quickly began to fade. DJ was so likable that I found myself crushing hard. I was determined to keep these thoughts and feelings to myself so I wouldn't ruin the relationship. Then, the first time we spent the night together, things moved from platonic to physical. As it turns out, DJ harbored the same feelings toward me. Unfortunately, the societal pressures of high school made us star-crossed lovers. It wasn't ideal, but it was enough for me. For the first time, DJ made me feel seen.
The second time we messed around was just before Thanksgiving at his house. Then the fall break and DJ's basketball schedule caused a drought in get togethers. Our interactions were relegated to video games, snap-chat, and discrete glances in the halls of school. As eager as I was to engage in physical aspects of our budding romance, I really enjoyed talking with him too. It was really healthy. It boosted my self-confidence and developed the emotional aspects of our relationship. The more sexually charged conversations also helped us establish our physical boundaries and roles. I wanted him to take my virginity and he was just as eager to take it. We talked about it a lot and I thought about it even more.
I was determined to have a good first experience so I scoured the internet for guidance. After a lot of research I started to experiment with myself. I started with a finger in the shower. Then two. Then three. At first it was unbearable, but it got easier the more I tried. Eventually it became enjoyable. When I was comfortable with fingers, I decided to upgrade to a dildo. I went to a sex shop next to a truck stop on the highway outside of town. It was a thrilling experience just to go in the store and buy the dildo. After browsing for a while, I bought a life-like dildo that I estimated to be about the same size as DJ's cock - 7.5". I rushed home to try it out. It took some time, but with a lot of lube and patience I got the head past the threshold of my tight ass. The initial pain was unreal, but I was elated that I could get it in. After a few more nights of practice, I could push it inside with ease. After a week or so, I had the hang of it - at least well enough to have sex without any extreme discomfort.
After nearly a month, our schedules finally aligned the weekend before Christmas break. My parents were away for the weekend, traveling together for dad's work so I had the house to myself. DJ didn't have any games or practice for the weekend so we were good to go. We planned to make a weekend of it - exchanging Christmas gifts, watching movies, playing video games, ordering food, and just being together. Most importantly, sex. As cliche as it sounds, I wanted the weekend to be special - and it was.
I woke up early on Saturday morning. I showered, shaved, and cleaned my room. I had to keep myself busy for fear of overwhelming nerves. DJ texted me that he was on the way over and reality set in. I started to panic a bit. As DJ pulled in the driveway the butterflies in my stomach were so fierce I could have cried. I watched through the window as he walked confidently toward the door. He had a little duffle bag and was wearing sweats and his letter jacket. His jock swagger turned me on so much. I opened the door before he could knock, grabbed his shirt, and pulled him inside. I used my grip on his shirt to pull myself up and kiss him before he could speak. The tactic was a bit more aggressive than I had envisioned and had caught DJ off guard. But, within seconds he was kissing me back just as aggressively. It was the most passionately that we had kissed.
