My parents were out of town and my sister was having a party in the basement. Michael and I were camped in my room upstairs watching some shows.
One conversation led to another and soon we were on the topic of wet dreams and jerking off. Michael was clueless on both accounts.
I was excited to show him my new found joy and soon we were both stripped naked lying on my queen size bed.
Michael still hadn't gone through puberty(ends up he needed some hormone shots later on). His penis, though rock hard, was only about two inches long and he was completely hairless down there.
I started in on myself, showing him how to grip his shaft and start stroking up and down. He followed my actions but after a few minutes declared nothing was happening.
I then offered to show him and reached over to grab his dick. Because it was so small I could only use my index finger and thumb to stroke him.
In no time Michael was telling me how good it felt and what a wonderful feeling it was. He was lying completely flat on his back, with his eyes closed and and soft moan coming from his mouth.
I continued stroking him, listening to his moaning and breath increase with time. Less than five minutes into this Michael wanted to stop because something was happening. I told him to go with it, this was the best part.
Next thing I knew his breath got really hard and really deep as he arched his back and his entire body shuddered with his first ever orgasm. His eyes were big as he looked at me and grinned.
We both went to sleep after that and never talked about it again.