Once when I was 13 years old my best friend Garrett and I had just been in health class learning all about sex and masturbation. We had been at my house watching a movie and having some conversation about the stuff we heard today.
At about 10pm when my parents went to bed me and Garrett decided to make a pallet. After we made the pallet we got my comforter and laid down to watch the movie. After about 15 minutes I noticed a motion coming from underneath the covers. I could tell it was Garrett rubbing his penis. About 10 minutes after that he asked if I cared if he slept naked? Being straight this kind of scared me but I still said yes. He ended up throwing off his boxers half way through the movie and fell asleep (maybe faking). Thinking about what Garrett was doing instantly made me hard. Soon after I took off my boxers too and acted asleep.
About 10 minutes went by before I felt Garrett's hand nudging on my leg. I knew exactly then what he was thinking. After him rubbing my leg I gave him a nudge to acknowledge I was awake too. I then turned over towards Garrett to be face to face, yet I still kept my eyes close in case it was awkward. Garrett ended up being the first to rub his hand by my penis and grabbing it. Immediately I was stunned how much better it felt to have someone else hold my penis. After about two minutes of him stroking my penis and rubbing my leg I moved my hand toward his leg. I then began to rub up from his knee to his penis and started rubbing it. For about twenty minutes we shared this moment of masturbating together before he ended up cumming first on my hand and leg and then him finishing me off about five minutes later. We're now 19 and college roomates at OU and still to this day jerk each other off maybe once every two weeks. Much has happened since this but that's for another story.