I'm 16 and I've been masturbating since I was about 11, this site has been soo helpful with techniques, and after this story happened, I've loved hearing stories of guys getting themselves off, well, here it is.
I was 13 the summer that I did the summer theatre program with my acting coach, he had staff members who had graduated from high school, and my story concerns one of them, Kevin.
He and I are both natural redheads, so everyone in the group called us brother and sister, which sucked because I had the biggest crush on him. He was 18, and I think he knew I was totally too young for him, so he also treated me like I was his little sister. I would flirt with him, but he only responded to be nice. Every afternoon, when my mom drove me home, I would think about him and I'd have to run up to my bedroom, lock the door, strip, and touch myself, fantacisizing about him. I had just started getting red pubic hair, and I imagined him with me, naked, also with red hair, that would usually make me cum really fast.
The third week into the summer we were all put into groups and given staff members, I prayed to get him, and my prayers were answered (though I found out later, he had picked my group because he wanted to work with me and my scene partner Emmy). We were given scripts and rehearsal times, and we all went home. Emmy and I talked to our moms and convinced them to let Emmy come over so we could work on our script. We talked about the script the whole way home, but when we got up to my room, the conversation turned to Kevin. Our first rehearsal was at his house that Saturday morning. Emmy said she was so excited we were in his group, and confided in me that she had a crush on him. I laughed and told her I did too. she said, 'but he looks like he could be your brother.'
I said, 'I know, but he's not really my brother, so its ok.' She said she guessed I was right. I said to myself 'what the heck' and told her that I even touched myself thinking about him. Her jaw dropped, 'really?! You do?!' I smiled, 'Yeah, like everyday.' She grinned a little, 'I've only ever done it once or twice.'
Emmy was my age, but looked younger than me, she was skinnier, and had practically no chest, but perky nipples. She was definately cute though. We talked about masturbating most of that afternoon, we locked my door, stripped and I showed her what I did and helped her out a little bit, she had never cum, but she did a couple times that day. I did too seeing her hands rub her hairless mound. I told her I had thought about Kevin doing it, and what that would look like. She laughed and joked that we should ask to see.
That saturday, I had a plan, if Emmy and I did what we had done in my room, Kevin would watch and want to show us, she was scared, but she agreed. As we got to his house, his mom was leaving, we got dropped off and he took us to his room. We talked about our script for a while and he told us to show him what we'd rehearsed, I almost laughed out loud at the irony. I looked Emmy in the eyes, smiled, and started unbuttoning my jean shorts, she followed my lead, and in ten seconds, we were rubbing our clits and moaning. He was just watching, not even touching himself, so I stopped rubbing and started stripping Emmy, I pulled off her shirt and shorts, and panties, then mine. When we turned to face him totally naked, still touching ourselves, his shorts and boxers were down and he was rock hard. I came right away, but kept rubbing, moaning really loud. As Emmy started to cum, I saw him shake and four white streams shot out of his dick and landed on Emmy's thigh and my arm, I licked it off my arm, and loved the taste.
We had more rehearsals, but that's for another entry.