I started college a couple of weeks ago. I have a roommate (whose name I won't mention for privacy reasons) who I've become pretty good friends with. He's not really my best friend or anything but he's good company. We've gone drinking together and shit like that. So onto my story...
Yesterday morning I woke up when he hopped out of bed because he was making noise and I noticed that he had a serious tent in his boxers. Of course I knew that he had morning wood and I didn't really care. I had morning wood too so it wasn't really that weird even though that is the first time I had ever seen a guy with a boner in just his boxers. Anyway he sat at his desk and powered up his computer and I tried to go back to sleep. I closed my eyes but I heard him stroking his dick through his boxers so I got curious and looked over at him very subtly so that he might think that I was still asleep. He was looking at ESPN on his computer and rubbing his dick which was all hidden except for the side of his head which I could see through the fly. I watched for a couple of minutes and got even harder than I was when I woke up. Even though I'm straight I was really turned on and wanted him to start really jerking off but he didn't. Instead he stood up and went to his closet to grab a towel for his shower. So I pretended to wake up and looked immediately right at his boner in his boxers. He saw me look and quickly turned away. I played it cool and said good morning and started talking. He slipped back into his desk chair facing away from me but I could still see his boner so I said: do you have wood too? He acted surprised and said "what?" I said "I have a huge hardon and it looks like you do too. I guess we are good roommates." I laughed but he looked really uncomfortable. So I said: "Don't worry, it's totally normal." He said "Yeah but I'm getting hard way too much. I gotta blow a load soon." So I told him to go jerk off in the shower. But he responded "I can't. I need to be sitting and I'm not sitting in that shower."
I suggested "Then jerk off in here. I could use it too. We'll just do it under the covers or something." So that's what we did. He got back into bed and we both went at it under our covers. It was really hot to be masturbating in the same room as somebody else, even if we couldn't see each others dicks. When I came I lifted up the covers to shoot on my stomach. It got all over my chest as my roommate watched. I hopped out of bed with my boner still tenting my boxers and cum running down my chest onto my boxers. I asked him for the tissues near his bed. He didn't respond. He just tensed up and started cumming into his sheets. I said "Well that will be hard to clean up" as I reached over to get the tissues.
He was pretty awkward until he left and showered off. While he was in the shower I smelled his sheets and got another boner so I quickly jerk off onto them to add my juices to his. When he got back he still looked a little pale but said that it was fun and thanked me for initiating it. He threw clothes on and took his sheets to the laundry because they were making the entire room smell like cum.
We haven't done anything since but we might. Especially if I see his boner again.