They had told me that college would be the best years of my life. For me they weren't. I was shy, insecure and not good at meeting new people. It was a nightmare for me. The first year I had two roommates who were heavy into drugs and partied almost every night in our room which made it impossible for me to stay there most of the time. Luckily, my sister lived off campus so I was able to stay with her when things were bad but I still felt like I should be enjoying the experience more. I had no problem getting drunk every so often but I was really not into the drug scene and that made the situation extremely uncomfortable for me.
Somehow I made it through that first year and as soon as it was over I put in for a transfer to another dorm. I got placed into the dorm for Liberal Arts majors and I was hoping that I might get a gay roommate so I could feel more comfortable with my living situation. The first day of the new semester, I was unpacking my things when John, my new roommate, arrived. He was about 5'10" with brown hair, green eyes and a little stocky. He wore old jeans and a faded green t-shirt and I knew instantly that I had not found my gay Adonis. He introduced himself and told me he was an aviation major. I wasn't sure how aviation fit into Liberal Arts but he seemed really nice though a little nervous. He talked a lot to mask his nervousness but I could tell that he was just as insecure as me and I was happy that I might have found a friend (or at least someone I could tolerate for nine months).
He was not the type of guy that I usually found attractive but he had such a likeable personality that it was hard not to be attracted to him on some level. Maybe it was because I knew that he was just as nervous as me. Anyway, I knew right away that I was going to have a good semester. I knew that he wasn't gay since he told me about his old girlfriend and made some veiled comments about being in the "Artist's" dorm but I didn't care. In a way it would have been much more difficult to deal with a situation where I was attracted to my roommate. He was just pleasant, somewhat goofy and somewhat cute. That was good enough for me.
Still, being in such close quarters it was difficult for me not to try to catch a glimpse of him when he was getting undressed or when he was wearing his jersey gym shorts that he wore to bed. I always liked the challenge of trying to see any man naked no matter who it was. And with him it was definitely a challenge. He seemed shy about his body and I don't think that I ever saw him completely naked that first semester. He would usually get dressed while I was in the shower or, if I was in the room, he'd go around to the other side of the dresser so I couldn't see him. I respected that, though I wasn't such a prude myself. There was nothing sexual about undressing in front of him for me so I never thought anything about it. But his shyness intrigued me and somehow made me want to see him even more.
Like I said, the closest I came to seeing him naked that first semester was when he would be in his briefs changing into his pants or when he wore the jersey gym shorts he slept in. They were the kind of shorts that clung just enough to the skin to show rough outlines of what was underneath if the lighting was just right and everything was positioned correctly. He usually got ready for bed pretty early and would do some reading before going to sleep so I had plenty of opportunities to see him in those shorts. When I was particularly horny I would make it a point to try to get a good look or hope that he would spread his legs enough to allow me to see inside. But generally it was just a habit to look like I'd look at any guy on the street.
I could tell, however, that it wasn't because he was small that he was embarrassed about changing in front of me. He didn't look huge but his bulge was respectable. I had thought for a while that he might have been shy because he had gay tendencies but he never looked at me when I was undressing so I quickly put that thought out of my mind. So I just chalked it up to good old fashioned shyness and let it go at that. Unless I was really horny I never thought about him in a sexual way anyway so it was not an issue and even then it was just the challenge of trying to get a good look at his dick. I was just glad we got along so well.
Our second semester we decided to remain roommates. We never really hung out together since we had such different friends but we still got along great. I never told him that I was gay but he might have figured it out at some point. If he knew he never mentioned it and he didn't seem to have a problem with it. I wasn't very sexually active but I did occasionally have friends over and he might have surmised that they were gay but he was always so nice to everyone. I think one of the reasons I was always so guarded was because I was so afraid that someone would find out that I was gay. Since he didn't seem to care I didn't feel like I had to be guarded around him and that allowed me to open up more than I usually did with people.
That second semester he still wore those jersey gym shorts to bed and I still tried to see what I could see. But he was still just as guarded as ever. Maybe he had figured out that I was gay and just didn't feel comfortable changing in front of me. That was fine with me. And if he ever noticed that I was looking at him he never let on. I tried not to be obvious about it but sometimes I couldn't help myself. Like I said I was not very sexually active at the time so I was always horny.
That second semester we decided to make our beds bunk beds. Before, they were each on opposite walls and it made masturbation difficult. He never said that that was the reason but I think we both appreciated the new arrangement. Before, whenever we wanted to jack off we either had to wait until the other was asleep or out of the room. Now we just had to be really quiet and really still. I remember nights when I had to stroke myself off with just the slightest movement of my hands against my cock so I didn't rock the bed too much. In a way it was kind of exciting getting off with him so close to me and possibly feeling the bed rock ever so slightly knowing that I was jacking off but most of the times it wasn't worth the effort. I had to be pretty horny to make myself cum like that and most nights I just fell asleep waiting to hear him snoring.
Most of all the new arrangement worked great though. He had the bottom bunk so I could still see him laying on his bed with his gym shorts on at night while I sat at my desk trying to do homework. Every time he moved I looked to see if I could see more of the outline of his cock or hopefully the beginnings of a hard on or better yet catch the head of his cock poking through the leg of his shorts. Most times it was just the same nondescript bulge with an occasional outline of the head of his cock.
I had never gotten used to having to wear clothes to bed since at home I had always slept naked. I tried everything from boxers to shorts but never really felt comfortable. I had finally settled on a pair of pajama bottoms that I brought from home. They were white cotton so thin that if you shined a light behind me you could see through them. But in regular light the best you could see was a shadow of my pubic hair. They had a fly front that never really closed properly so I had to be careful whenever I got up or sat down that everything was still inside. Those nights when I was watching John on his bed I had to keep adjusting myself to keep the head from poking through the hole and if I ever stood up when I was hard you could see my whole cock through the fabric as it pushed against the front. Needless to say, I sat down a lot.
One night I remember going to bed particularly horny. I waited and waited for John to go to sleep but he stayed up watching TV until at least midnight. I eventually forgot about it and drifted off. The next morning, I woke up still horny. I noticed my cock was hard as a rock and sticking through the hole in my pajamas. Unconsciously, I grabbed it and gave it a squeeze. I had never remembered being so hard. Right away I thought of John and put my cock back in my pants. At least, I thought, he was still sleeping. I climbed quietly out of bed and started to get my towel.
"You slept in," John said, startling me.
I turned around pulling my towel in front of my still throbbing cock. "Yeah", I said nervously. "Felt good." I noticed that he was already completely dressed. Had he seen my cock sticking out while I slept? All sorts of things started going through my mind.
"I got up early," he said. "Hope I didn't wake you."
"No," I stammered. "I was.ready."
He turned around, I took off my pajama bottoms and wrapped my towel around my waist and headed for the shower. Thank God the shower room was empty. I unwrapped my towel jumped into the shower stall and closed the curtain. My cock was still throbbing. I turned on the water, took some soap from the dish and rubbed it on my cock. It didn't take long to shoot my load. I swear I could hear it as it hit the shower curtain. The though of him seeing my hard cock like that was so exciting to me. I knew it was wrong but I wanted more. I wanted to know when he was looking or whether he was looking at all. I wanted to know how long he stared, whether it made him hard. I wanted to know if he touched himself while he watched me.
Unfortunately, John went home that weekend and I had to wait another week for my experiment. It was too difficult to try to manage it during the week. Our schedules were too different. But I planned and fantasized about the following Saturday all week. I had a plan - and every time I thought about it it made me hard.
When that Friday night finally came I made sure I went to bed early. John was still out when I went to sleep but he was never out late. I knew that if I woke up before him I would be able to follow through with my plan. I can't believe that I even got to sleep that night but I eventually did though I think I woke up every two hours. Finally about seven o'clock I woke up for good. I peeked my head down to John's bed and was relieved to see him still asleep. I was already half hard with the anticipation and it didn't take more than a few seconds to get myself hard as a rock. I pulled my cock through the hole in my pajamas and stroked it lightly. I practiced how I would lay so that I would look like I was still asleep but could still see his reactions. I tried several positions and finally settled on laying on my back with my head turned slightly toward the side of the bed he got out of. Now all I had to do was stay hard and wait.
About seven thirty I finally started to hear stirrings from underneath. I closed my eyes and gave my cock a few quick strokes to bring it back to full hardness then laid my hand on my side. After a few minutes I heard him get up. I only had my eyes opened a little so that he would think that I was still asleep but I could make out his outline against the light coming through the window. Soon, however, he was out of my sight. I couldn't move but I was so disappointed that he did not even look at me. I wanted to turn my head to see where he went but instead waited to hear the door close when he went to take his shower. Maybe he'd look when he came back, I thought, but I was way too hard to wait. I knew I'd have to jack off while he was in the shower or I'd never make it. I couldn't believe I hadn't shot my load just laying there.
As I laid there waiting to hear a noise I felt something soft brush up against my cock. I though perhaps that the wind had blown one of my sheets but soon it brushed back the other way. I laid still. I was pretty sure what was happening but I couldn't believe it. The stroking continued up and down my cock, soft at first then harder his finger pressing ever so slightly into the underside of my cock. I felt a drop of pre-cum roll down the head and my balls ached like they had never ached before. Carefully, he put his hand around my cock and worked the pre cum into the skin. He rubbed gently up and down afraid, I'm sure, of waking me.
I wanted so badly to turn my head to see his face but I resisted. Whatever he was doing felt so good and I didn't want to risk having him stop. He stroked me like this for about a minute and then I heard the creaking of mattress springs. After a few seconds I felt his warm wet tongue lick the head of my dick, lapping, I was sure at another drop of pre-cum that had formed there. I felt my dick leap as he licked my cock head and I was afraid that it might startle him. Instead he continued, running his tongue down the length of my shaft down to my balls and back up again. This time he opened his mouth around the head and slowly took it in his mouth. I ached for release and wanted so badly to thrust my cock down his throat but I kept up with the game. Nothing I could have added would have made what he was doing feel any better.
Slowly he took my whole cock in his mouth and came up for air. He hesitated for a minute then went down again. He was hungry for my cock and I was willing to offer it to him. This time he took my whole cock in his mouth and I could feel my cock head touch the back of his throat. As he pulled up again I knew I was close to shooting my load but knew I couldn't warn him. Once again he hesitated over my cock and I could feel his warm breath on it. He gave it a few more licks then slowly tasted it again. Eagerly, he engulfed the shaft and slowly he released it. This time, however, I had had all I could take. As he started back up the shaft I shot my load in his mouth and I could feel him swallowing the cum. His lips involuntarily squeezed my cock and I sent another load into his mouth. This time he released my cock and I unloaded the rest of my cum into the air, droplets landing on my stomach and the leg of my pajamas.
I don't know how he could have imagined that I had slept through all of that but I continued to feign sleep as he licked the few remaining droplets of cum from the head of my cock. Finally, I rolled over, hoping to see what kind of expression he wore on his face. I slowly turned, moaning a morning moan and stretching -- pretending, I guess, to be turning over in my sleep. As I made it to the other side of the bed, however, I saw the door closing as John made his way to the shower room.
I pulled my half hard dick back into the hole in my pajamas, pulled up the covers and fell asleep. By the time I woke up again John had left and I was hard again. I pulled my cock out of the hole in my pajamas and looked at it, imagining that John was still there looking at it with me. Then I rubbed my finger on the underside of the shaft feeling the same place he had felt a few hours before. I continued to jack off remembering what had happened that morning and planning next weekend's game.