When I was in high school it was the boom of online chatting. I had met a girl in a chat room and we had a lot of fun; talking, playing, sending nudes, roleplaying, etc. Eventually this girl got a boyfriend. Her behavior toward me didn’t change much and we still enjoyed our fun together. Somewhere along the lines in our communication though she started telling me about how her boyfriend and his friends would give each other handjobs. This was a completely foreign idea to me. I had never considered touching a friend’s penis or vice versa. Over time, the idea became more intriguing and she even sent me pictures of her boyfriend naked and we’d Roleplay to include him. It was actually pretty hot.

Eventually she told me I should try it and convinced me to talk to my friend John about it. After a while, I got the courage to do that. John had known about the online girl so it was an easy conversation to begin. One night we were in the back seat of our friend’s car when I told him about the girl’s boyfriend and the things he’d do with his friends. Eventually leading myself up to the big question, “Is that something you’d consider doing with me?” His simple reply of “yes” was an easy enough answer. Now it was a matter of when.

Much time had passed and I had forgotten about the conversation and hadn’t really considered that it might actually happen. High school was ending and we were having a sleepover at our friend Mark’s house. Mark was the last of us to turn 18 and hosted us for the sleepover. John and I were forced to the pullout mattress on the floor. Sleep didn’t come until late into the night/morning. Mark was on his bed snoring and John and I were on the pullout mattress. I was finally asleep when I was awoken extremely aroused. Soon I realized the source of my raging hard-on was John’s hand. I froze. I didn’t know what to do or how to respond so I did nothing.

Soon John started stroking me faster and I was in pure bliss. Then he snaked his hand up my shorts and I couldn’t believe what was happening as John worked his hand under my underwear and directly onto my hard cock. John was giving me a handjob…and it felt amazing. My thoughts were no longer about how I felt about this but instead by how good it felt. John expertly worked my cock and I gave him better access by lowering my shorts and underwear.

My cock was his to play with. I was clearly awake as was he but neither of us spoke as I “pretended” to still sleep even though we both knew I wasn’t. John moved his hands lower and began massaging my balls. He knew what he was doing. And he was good at it. Then, to my further surprise, he went lower and sunk a finger into my tight hole. My best friend was fingering me! I couldn’t believe this and all I could think about was my need to release.

I took John’s hand and moved it back to my throbbing cock. I knew I needed it. John knew I needed it. Still no words but an unspoken desire needed to be relieved. I needed my best friend to make me cum. Now back on my cock, John expertly work me again. Stroking me, up and down, up and down. I felt my body reacting more and more. My hips moving to his touch. I was so close. I was ready.

Finally, after what felt like hours of teasing, massaging and fingering, it was the moment of truth. My best friend was the source of my orgasm. I began to shoot stream after stream of hot cum into my friend’s hand. He milked my cock until there was no more to milk. When my orgasm subsided, I discretely went to the bathroom and cleaned up. I got back in bed with John, my best friend, who I was a little bit closer to now.

….and it wasn’t long before his hand was back on my cock working it for round two.