Donny, the new neighbor who moved into the double across the street, came over a lot and we soon became really good friends. He was a year or so younger than me, my brother's age, and we would play hide and seek, laser tag, and Nintendo until all hours of the night. We both had Commodore 64 computers and would stay up all night at each others' houses playing video games and eating garlic popcorn.
Before long, truth or dare became the game of choice between Donny, myself, my brother, and the occasional couple of other neighborhood boys, Jesse, Jimmy, or Jamie. The normal themes of course were truth questions about our limited or altogether nonexistent experience with girls and the dares involved nudity of some sort or another. The most popular and recurring dares often involved stripping naked and going outside into the yard in the night, which would inevitably be followed by a door being locked as a flood light was turned on... stripping naked and climbing into a chest... stripping naked and humping any random object be it a floor lamp, pillow, or the leg, bottom, or body of a randomly selected boy. How we managed to do as much as we did and never wake our parents I will never know.
After one such game, we were all staying the night at Donny's house and everyone had started falling asleep. With images of my friends' penises wagging through my mind, I found myself quite unable to sleep. My brother was asleep on the floor of the living room, Jesse had long gone home and Donny was on the couch. I slowly got up off my chair and quietly walked over to the couch and knelt down to see if he was really out. If he was, I planned on sneaking into the bathroom to jack off so I could go to sleep.
I put my hand on his arm and gently shook him. When he did not budge, I whispered his name... still no response. I realized he was a very heavy sleeper and I just could not resist touching my cock while I had my hand on his arm. I pulled it out of my shorts, already hard as I've ever been and lifted his hand and put it on my cock. The heat of his hand felt so good. I let go of his arm and just let his hand sort of hang there resting on my dick. Afraid he would wake up and catch me doing all this, I set everything back to normal just a few moments into it, laying his arm across his body.
As I did so, I realized I could touch him too. And I did. First through his clothes and then I reached up and under the loose leg of his shorts and lightly stroked him through his briefs. He still had not moved or made any sign of waking up... I watched his face intently looking for any sign at all of that changing, not really even thinking through what I would say or do if he did.
I always thought Donny had a bit of a girlish look to his facial features... he had eyelashes that were a little longer than normal and his lips almost looked like he was wearing lipstick even though he wasn't. Without thinking, my hand still in his pants, I leaned forward and kissed him. That did make him stir a little but he did not wake up so I did it again, this time licking his lips a little. My free hand had pulled my hard dick out again.
There I was, on my knees slowly stroking myself with my right hand, my best friend with my left, lips pressed to his, breathing in his breath as he exhaled and feeling him getting hard in his sleep. I grabbed one of his dirty socks from the floor and slipped it over my dick and started pumping myself faster, wishing I had some way to get his dick into my mouth. Afraid of waking him up, I had stopped stroking him and just held my hand still on his hard dick, feeling his balls with the tips of my fingers and lightly pressing my lips into his as I came in his sock.
I cleaned myself up with it and traded it for another dirty sock I had found in his bathroom hamper, kissed him goodnight and finally managed to get to sleep on the chair next to the couch. All the while, my brother lay sleeping a few feet behind us, I had just had an amazing time with my best friend and wished there were some sign he would ever feel the same enough to do more... preferably when he was awake.
While it never happened, I often thought of him when jacking off. When he would stay over at our house, I would sneak his socks and shoes into the bathroom and prop a school picture of him up on the toilet paper holder on the wall and tie my cock up in his shoe laces or hump the floor with my dick in his shoe with his socks tied up against my face with his other laces. Sometimes, I still think about him when I masturbate. Those certainly were very good times.
