Wrestling James

This all started around the time that I was sixteen. James (not his real name) and I lived in the same condo complex. Since this was the Nineties and there was only one way in and out of the complex, the kids could run free for most of the day, as long as they stayed inside the confines of the complex. There was a plethora of hiding spots, hidden back entrances to abandoned condos, and rarely visited common areas. Because we were the same age James and I spent most of our time together. James was a very popular boy in our school, while I was very much the opposite. James was athletic and sported a six pack before anyone else in our grade, had a beautiful red hair and just the right number of freckles around his eyes. I was a slightly overweight Latino boy, a late bloomer and stylistically deficient. At school, we pretended not to know each other; or he pretended not to know me. Either way we didn’t interact much. But the moment we stepped foot into our complex, the world belonged to us. We spent the night at each other’s houses, watched movies we shouldn’t have watched and talked about girls at our school. One night while spending the night at James’ house, we got on the topic of penis size. James claimed to have a bigger than average penis while I admitted that I didn’t know; I had never seen one other then my own. “Really!” James said in shock. James had a big family that he visited frequently. Plenty of opportunities to see a cousin’s while swimming or any kind of similar opportunity. I only had my mother, since I was first generation American. We got off the subject of penis size and watched whatever was on Nickelodeon at the time, as we sat next to each other on his twin bed. Out of the corner of my eye I could see a clearly enlarged bulge in James’ sweatpants. This sent a heat I had never felt before running through my body. My body reacted, and before I knew it my sweat pants had a bulge of its own. I looked at James and he looked at me. “Have you ever masturbated?” He asked me. The words spilled out one over the other like he had been waiting to ask me all night. His parents were drinkers, so the odds that they would walk in on us or listen into our conversations was slim. “Yes,” I answered, “But not in front of anyone else.” “Neither have I.” We giggled for a while, but the heat still spilled through my body and clouded my head. Now the next part of the story is up for debate. We don’t know who drew first blood. He claims it was me, I claim it was him. It will never be solved. But after our fits of giggles, we began to engage in one of our favorite pastimes; wrestling. By now both of us were fully erect, and through his sweatpants I could clearly tell that he was most definitely larger then I was. We took turns pinning each other and breaking out, spinning around and around on his bed until ONE of us, grabbed the other’s boyhood over their sweatpants. AGAIN, I am not sure who started this exchange. But the other responded by grabbing the other’s member. We quickly let go and scuttled to opposite corners of the bed. Our attention turned back to the tv. After all these years I can still feel how my heart beat faster then it had ever beat, and how the cloudy heat that filled my body intensified. All I knew is that I wanted to do THAT again. So, after a few minutes of panting, I tackled him from behind initiating another round of fevered wrestling. This time it was different. We made it a point to rub ourselves close together. Focusing on pelvic related moves. This round I know who struck first. James let me pin him to his bed and with a free hand he reached down and grabbed me again. I quickly responded by returning the favor. We held each other for a little longer this time before breaking out into giggles and running to a corner of the bed to pant and stare at each other’s erections through our sweatpants. What felt like an eternity past before James was on top of me again pinning me to his twin bed. His pale skin bright red, his significant shaft pressed up against my stomach. I wrestled my hand free with no effort and placed my hand on his impressive member. He reached behind himself and did the same. This time we did not let go. He slid his body with purpose down my own, sitting face to face with me. We did not make eye contact. We just stared at our own hands holding the boyhood of their closest friend. Then our hands began to move. We moved our hands up and down while firmly gripping one another through our sweatpants. We didn’t speak, we just stroked over and over until I felt the heat within myself center to my pelvis. This was a new, wonderful feeling. And we both moaned with pleasure. James briefly took his hand off my member, I was taken aback wondering if he had had enough. He reached lower to cup my balls, something I had never thought to do to myself. It felt spectacular and wrong all wrapped up into one glorious moment. Soon we picked up the pace of our stroking until he gave one final moan I can still hear clearly today, not a second later I had finished into my sweat pants as well. We panted and smiled at each other, each taking a turn in the bathroom to clean up the mess we had made in our own pants. Then we went back to watching tv and laughing as if nothing had changed between us. It had; our sessions after that became increasingly elaborate throughout our teen years. Every one of my first sexual experience was with James. Hundreds of close calls, bad excuses, and the best sleepovers of my life.