Some fun with a roommate
Starting at about age 13 I discovered masturbation, and soon after became addicted to it, sneaking off 2-3 times during the school day to do it. During this time I was attending a boarding school, and it was difficult to do it in my room because I had a roommate and he was kinda always around. So, one night after lights out, probably around February, I decided I would wait for him to sleep before getting in one last jerk before I went to sleep. I jerked furiously, but as quietly as I could manage, and came in about two minutes, it's then that I received the shock of my life when my roommate asked 'did you come?' I almost had a panic attack, but I answered, 'kinda' I said (I could have orgasms but didn't shoot anything yet), he then asked 'can I see?'. So I decided to turn on my bed lamp and show him, he looked for a minute and said 'cool', at this very moment our prefect came banging on the door yelling 'quiet in there its lights out!' we both kinda freaked and I shut off the light and we eventually went to sleep.
The next night as soon as it was lights out he turned on a little flash light and asked if he could watch me, I was kinda nervous as no one had ever watched me before. But, I said OK. He climbed out of his bed and sat on the ground next to mine watching, about a minute in he asked if I had ever measured it, I had never really thought of that until this moment so I said let's try. I took out my ruler from math class, you know the little six inch ones, and we measured it, about three and three quarters to four inches, I had just hit my first growth spurt, barely any wisps of hair or anything. I finally asked if I could see his, and he just froze up, and finally said 'let me watch you finish, maybe tomorrow', ok. I finished, and a little bit of clear fluid came out, I was so excited, he reached out and touched it with his fingers, I almost came again at that instant. He then went back over to his bed and we fell asleep.
The next night was Friday, and we didn't have as strict rules for lights out then, so we just kinda hung out in our room til about midnight, I was playing my gameboy and he figured it was a good time to do lots of exercise, he was on the soccer, wrestling and track team all-starter. I remember being kinda jealous of him as he had like a eight-pack, pretty big biceps and even pecs, no one else in our grade had pecs, and I still had my puppy fat. Well I guess now would be as good a time as any for a description, I'm pretty much 100% Italian, at the time I was about 5'3' or 5'4', chubby, black hair in a bowl cut, and had glasses. He was about the same height as me maybe an inch taller, totally ripped, well as ripped as you can get at that age anyway, black (I think he was Caribbean), and buzz cut hair. Anyway, he finished his exercise and went to take a shower, I figured now was as good a time as any and took out my dick and started working on it. Just as I was really getting into it he comes back in!, 'sorry I forgot my soap' and then he saw what I was doing and he hurriedly closed the door.
He sat down on his bed and started watching me, I finally said 'you know it's totally unfair that you keep watching but never let me watch you' his face froze up and I thought he would bolt, then a smile cracked, and he dropped his shorts. I was floored, it was huge and he had tons of hair around it, I ran for my ruler to see if I could measure it. I asked him if it was ok if I did, and he nodded yes. I reached out and touched it with a trembling hand, and wrapped my hand around it, it barely fit, as I put the ruler in place, it was actually a little bigger than my ruler maybe by half an inch or so. I asked him if he ever measured it and he went over to his desk and brought over his ruler, it was steel, the type they used for wood shop or metal shop. I measured it again, six and three-quarter inches almost exactly. I thought, it was definately bigger than my dads was when I spied on him and learned how to jerk off!
I looked up at him and he seemed to be off in another world enjoying the feeling of my hand on him. I asked him if I could watch? He said ok after some deliberation. So I sat on the ground next to his bed, he sat on his bed and I watched. He must have jerked off for a full 30-45 seconds before he came, it went everywhere!, tons of it! he picked up a t-shirt from his hamper and wiped it all off, and said 'now you' I came in about 20 seconds, it was definitely too much for my young mind to handle and I shot a little bit of clear fluid, with some white in it. He handed me the t-shirt and said 'clean up, I need to take a shower' and with that put his shorts back on and left the room, I fell asleep within minutes.
The next thing I notice is it's about 3am and he's waking me up, 'hey, lets do it again' he says. I woke right up, he took out his flashlight and we started at it again, and then he says 'can I do you?', I felt really unsure about it but thought 'why not?', and said yes. He came over and sat on my bed next to me and reached over, he grabbed my dick and I came just from that, but he kept jerking me and I soon came again about two minutes later. I reached over and grabbed his enormous penis, and began stroking, I tried to use the two-finger ring method I used on myself but found it inadequate on something this size, I switched over to how I saw him doing it, full-fisted, and he seemed to enjoy that much more. He started to get slipper with what I now know is pre-cum, but at the time I just couldn't figure it out, I thought he might have cum, but that didn't make sense since I saw him shoot before. So, I kept at it, my arm was definitely getting sore now but, he looked like he was really close so I kept going, about one minute after that he shot everywhere, most of it on his chest and stomach, some on my hands and his cock, and somehow a splash hit my nose. He reached over and wiped it off with his finger and then touched it to his tongue, he said 'I'm not doing that again, I think it tastes bad,' I started laughing, and he soon followed. I got another t-shirt from the hamper and we wiped him off, I took my finger to the last little bit on his stomach and tasted it as well, it was interesting I wouldn't say bad but I can't say it was good either. We quickly became tired and went to sleep.
From that time on until June when we left school I would watch him jerk as he watched me, and on the weekends we would jerk each other. It was fun, and sucked that we got different roommates the next year, but about once a month or so on weekends when one of our roommates would be gone we would sleep over at the others place and do it at least twice before we went to sleep and once more when we woke up before we took a shower. Those were the good old days, LOL.