The March afternoon, despite being sunny, remained chilly. The deep woods did their best to block the breeze, but with my jeans lying around my ankles I was still cold. The only warmth came from his buttocks and thighs as I pressed against him. We were trying to have anal sex for the first time and we were getting nowhere.

Just a young teen, I had several months of fellatio experience, all with him, but the concept of anal sex was new to me. Apparently he’d seen images in magazines he’d found in his dad’s truck, but he only mentioned the possibility to me the previous night. Intrigued with the idea, I tried to make my way into his chubby butt the night before, but failed. I failed in that no penetration occurred, but succeeded in having a good time trying. The warmth of his crack, combined with the slipperiness of the soap we’d both applied in separate trips to the bathroom provided a quick orgasm.

Now, standing in the cold woods, we’d both forgotten to bring lube. We wouldn’t discover Vaseline for a few more weeks, and now were limited to my diminishing supply of saliva. Without the superb stiffness of an adolescent cock, we’d have failed, but on the tenth attempt I dribbled enough spit directly on the tip of my cock to make progress. I knew this immediately, when he stiffened up and asked me to slow down. This time when I eased back, the glans remained inside him. This was really going to happen, and it felt like I stiffened even more.

After a minute he encouraged me to push further, and each time I made a bit more progress. Within minutes, I felt my pubes bottom out on his cheeks, and my balls nestle in behind his. I savored the warmth, yet realized what a huge red line we’d just crossed. This was more than innocent sex play, this was full blown sex. Gay sex at that. I could tell myself we were just doing this because no females were available, but deep down I knew most boys without girlfriends weren’t doing fucking their make cousin in the butt.