This took place on my first day of college, a while back.
When I met my new roommate, he seemed like an ok guy. He arrived with his parents and his girlfriend and his brother, and he seemed like a friendly person. We unpacked, arranged the room, went to dinner, and did the normal things you're supposed to do on the first day of freshman year. It seemed like we were going to get along well.
When it got to be bedtime, I didn't know what to do. I'd brought pajamas, but I didn't know if that was cool so I waited to see what he would do. He stripped down to boxers and a t-shirt, so I did the same and left the pajamas in the drawer. When it came time to turn out the light, he looked at me like he wanted to say something, but he hesitated. I waited, and after a couple of seconds, he came out with it.
"I usually jack off at bedtime," he said. "Is that going to freak you out?"
Well, that caught me by surprise. Did he really say that? I didn't know what to say, but I didn't want to be disagreeable, so I just said sometime like "Whatever you want. Don't worry about it." I don't remember my exact words, but you get the idea. Actually, I didn't know if that was going to freak me out. It probably would.
Sure enough, as soon as the lights were out, he went at it, completely uncovered. There was enough light coming in from the window and hallway that I could easily see what he was doing, and he wasn't being shy. He wasn't making a lot of noise - no "Oh God" or anything like that -- but he wasn't trying to be quiet, and there was heavy breathing and a moving mattress and squishy sounds.
After a couple of minutes, he grabbed a small towel from beside the bed, put it on his chest, and let go a healthy stream of cum onto it. He rested for a minute, then used the towel to wipe himself off, then carefully folded the towel and put it back onto the nightstand.
Then he looked at me. "You ok over there? You said it was ok."
I couldn't resist asking. "Aren't you embarrassed to do that when somebody's watching?" I said.
"What's embarrassing?" he said. "It's not like I'm doing anything wrong."
That made sense, in a way, but not really. I'd never met anybody who was so casual about masturbation. It's not something you do around other people, is it? You don't even talk about it with other people. But there he was, with his dick still in his hand. I decided he could do what he wanted, but I certainly wasn't going to whip my own out and go at it with him watching.
Then he continued. "I share a room with my brother at home. What else can I do? A man's got to do what a man's got to do."
I don't know what I would have done if I'd shared a room with a brother. "I don't know," I said. "I couldn't do that, with somebody else in the room."
"You must do it somewhere. Where do you do it?" he said.
If he was going to talk about jacking off, I guessed I could too. So I answered. "Usually in my room at home. I have a room by myself."
"Every night?" he asked.
"Yeh, pretty much," I answered. "Sometimes in the morning too."
Then he asked a really good question. "What was your plan for what you were going to do here in the dorm?"
That was a good question. I'd been puzzling about that, but I didn't know, so that's what I told him. "I didn't have a plan."
"Well," he said, "don't worry about me. I don't care what you do. What needs to be done needs to be done."
Actually, I'd known I had to have a plan. As a matter of fact, I knew I had to have a plan that would work every day. Truth be told, that was my biggest worry going to college. How would I jack off every day when sharing a room with a roommate? I did some Internet research. There were recommendations to use the shower, but I have a lot of trouble cumming when I'm standing up. Somehow, I need to move my legs around or something. It doesn't work standing up. I really need to be lying down. I could wait for my roommate to leave the room, but that seemed too dangerous - he could come back unexpectedly. That left the final possibility, which was waiting for my roommate to be asleep. That was my only choice.
Over the next few days, we hung out a lot and went to meals together, and we even had one class together. We kind of latched onto each other as best friends. And I developed a plan for "what I was going to do." I waited till he was asleep, then quietly opened my bottle of lube and took care of myself. I figured that's what most guys did in the dorm. It isn't great having to be really quiet, but I did what I could.
And every night at bedtime, he took care of himself, sometimes even before I'd turned out my light. He didn't care what I saw. Sometimes, he'd even talk to me while he was going at it with his dick in his hand- not about sex, but ordinary stuff like classes and sports. Believe it or not, I got used to it. I'd usually sneak a peek while he was busy, usually when he was cumming. I sometimes felt guilting peeking, but everybody would, wouldn't they? He caught me looking a few times, but he didn't care.
About a week went by, with him doing it openly and me doing it privately, and one night I had a particularly good session with an extra-big load at the end. As I was quietly cleaning myself and hiding my lube, he spoke up, breaking the silence.
"That was a good one," he said.
Oh shit. "You were watching me?" I said.
"I watch you every night," he said. "Eleven thirty, like clock-work."
I was a busted as I could be, and I'm sure I was turning beet red in the dark. "I thought you were asleep. You should have said something."
"I didn't want to spoil your fun," he said. "You'd stop if you knew I was awake."
He was right about that. I kept quiet, trying to calm down.
"You don't need to wait till I'm asleep, you know. I don't care what you do. It's nothing I haven't seen a million times before," he said.
Shit. Could this get any more embarrassing? Yes, it could. He added, "That thing you do with your nipple looks like fun. I should try that." Then he looked at my face and saw sheer panic. He laughed and said "It's cool man, don't worry. Nobody cares. Have fun."
It took me hours to get back to sleep. The next day, I thought I was having a panic attack. I was nervous and brain-fogged all day. He and I went to meals and class together, like normal, and he tried being extra-friendly to get me to relax. It helped a bit, and by bedtime, I was almost normal. I was looking forward to lights-out, when I could hopefully be alone to think. Hopefully, he wouldn't want to chat while he was jacking.
We stripped to boxers and t-shirts, got into bed, and turned the lights out. Like normal, he pulled out his boner and started stroking. Thankfully, he wasn't talking.
Then he spoke. "You should take care of business now," he said. "No point waiting till 11:30."
I didn't answer.
"It's not a big deal," he said. He was trying to be encouraging. Then he added, "I won't see anything now that I haven't seen every night for a week. I'm busy over here, so I won't pay attention to you. Just ignore me."
I knew he was right. He'd seen everything there was to see, not once, but a bunch of times. What was there to worry about? He was looking away from me and was busy himself. So I fetched my lube, pulled my dick out of my boxers, and tried to stroke. I got hard, but I couldn't keep it up. I was too nervous. I stopped.
"I can't do it with you awake," I said. I knew it didn't make any sense, but there it was. I couldn't.
He rolled over and looked at me, still stroking himself. Then, believe it or not, he got out of his bed, came over to my bed, and sat next to me.
"Close your eyes," he said.
"What?"
"Close your eyes and think about Julia."
"Who's that?" I asked.
"The girl down the hall who never wears a bra. With the nipples poking through her shirt."
I knew who he meant. That was, indeed, a sight worth thinking about. I didn't know what he was doing. Maybe he was going to tell me a dirty story to help me get off. I closed my eyes and imagined what Julia would look like without the shirt.
Then I felt it. He had his hand on my dick and was rubbing it. Shit! My eyes flew open and I pushed his hand away. "What are you doing?!" I was almost shouting.
