Freshman Year in the Dorm

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My new roommate helps me lose my sexual inhibitions.
3.2k words
4.27
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Part 1 of the 9 part series

Updated 06/11/2023
Created 09/29/2022
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alan556
alan556
290 Followers

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.

He put his hand back on my dick. "Just helping a friend," he said, completely calm.

"I'm not gay," I said, pushing his hand away.

He looked at me sternly, as if he were going to lecture me. "No you're not," he said firmly, "and neither am I. Helping out a friend isn't gay. It's just nice."

The look on his face was so intimidating, but also friendly, that I had no choice but to be quiet. He put his hand back on my dick and resumed rubbing. "Close your eyes and think about Julia," he instructed.

I did close my eyes, and I tried (and failed) to think about Julia. I didn't know what to think, so I didn't think at all. I let him stroke me. And to tell you the truth, it felt really good. It actually felt better than when I do it myself.

He would stroke me for a minute or two, then take his hand away for a second, then bring it back and continue. "That's good, isn't it?" he asked. I nodded my head. It felt really good.

I wanted to know what he was doing - why he kept taking his hand away - so I opened my eyes. He had his own boner sticking out through his boxers, and was using his own pre-cum to lubricate my dick! He would take his hand away from my dick, stoke himself once or twice until his hand was wet with his pre-cum, then bring it back to my dick!

That's why it felt so good! I don't normally have much pre-cum, so I need to use a lot of lube. Real pre-cum felt so much better, even though it wasn't my own. God, was that weird. God, was that good! I took a deep breath, relaxed a lot, and closed my eyes. I should have freaked out, but it felt so damn good, and I really needed to cum.

After a little while, I felt my dick getting extra-hard and knew that the time was near. I whispered, "I'm cumming."

"Good for you," he said. "Make it a big one."

Just a few strokes later, I came, and it was, indeed, a big one. I opened my eyes to watch, and saw the squirts go into the air and fall down on his hand. Three big squirts. Jesus! What a relief!

I closed my eyes again, to rest. A minute or two later, he took his hand away from my dick, then I felt him yanking on my shirt.

I opened my eyes. "Are you wiping your hands on my shirt?" I laughed.

"Your cum, your shirt, he said."

We both laughed. "That's fair," I said. "You're really good at that, you know."

"I have lots of practice."

"Don't we all?" I said.

"No, I mean doing it for other people," he said. "It's a skill."

"You do it for your brother?" I asked.

"All the time," he said.

"Does he do it for you?" I asked.

"All the time," he said.

"Is he as good as you?" I asked.

"He's learning," he said. "He will be. It takes practice."

Then he added, "You were doing that thing with your nipple."

I hadn't realized that. I must have done it unconsciously. "You should try it," I said.

"I will," he answered.

He went back to his own bed, grabbed his towel, and, a minute or so later, let loose the biggest load of cum I'd ever seen. I told him, "That was a good one!"

"Glad you liked it," he said, smiling. He put the towel away, rolled over and went to sleep.

I was exhausted and relaxed. This night, I had no trouble sleeping. And I didn't need to wait till 11:30 to fall asleep.

The next day, I felt like a burden had been lifted from me. He and I joked and laughed at breakfast and after class, with no mention at all of what had happened the night before. Just two friends hanging out with other guys, enjoying life. Even better, that evening Julia was walking through the hall on the way to the bathroom wearing the most amazing night outfit. Her nipples weren't just sticking out through her shirt--you could actually see their darkness through the thin fabric. That, and tiny panties, was all. She was ready for bed and who knew what she was going to do there. Best of all, she smiled at me in the friendliest way and said "Hi." That would give me something to think about later tonight.

Back in our room, we did some studying, then stripped down to boxers and t-shirts, and turned off the lights. Instead of getting into his own bed, he came and sat down next to me, on my bed.

"You ok taking care of yourself?" he asked. "No more shyness?"

I thought about that. Much as I enjoyed last night, with him doing it for me, I knew that was a one-time thing, so I had to get over my embarrassment. I reached into my nightstand for my lube. "I'll try," I said.

He stopped me with his hand. "That stuff's no good. Use mine," he said. He moved my hand to his dick, already half hard. He wrapped my hand around it, using it to stroke just a few strokes, and the first drops of pre-cum leaked out.

If you had told me a week ago that I would be stroking some other guy's boner, or even that I would jack myself off with him watching me, I'd have been grossed out beyond measure. But here I was, doing exactly that. And the most amazing thing about it was that it didn't feel at all strange or weird. It was like the most normal thing in the world. I guess, in some sense, it was.

I got my hand wet with his pre-cum, moved the hand to my own boner, and did what needed to be done. Every minute or two when I got dry, I'd move my hand back to him to get wet again, then back to myself to pick up where I'd left off. He, too, was stroking himself. When I brought my hand over, he'd move his away to let me stroke a little, then he'd bring his hand back to his own dick. I closed my eyes, and this time I had no trouble thinking about Julia.

I don't know why it felt so damn good. Maybe it was his pre-cum, maybe it was Julia, or maybe just having another guy's dick in my hand. But whatever it was, it was fantastic, and I wanted it to last. When I got close to cumming, I'd stop for a moment or two to rest. I'd open my eyes and watch him for a while, looking at the wetness at the tip of his dick, or looking at his foreskin moving as his hand was stroking, or his face with his eyes closed. Then I'd move his hand away, fetch some of his wetness, and stroke some more. He didn't seem to be in a hurry either, so I took my time.

Eventually, I couldn't hold back anymore, and I came, spurting my mess all over myself. I was quiet then, watching him. I could tell he was getting close, and I decided I wanted to be the one to finish him off. I moved his hand away and put mine in its place. It took only a few more strokes before he opened his eyes wide and squirted a nice load onto my hand and his own thigh. Then he smiled at me.

"Good job," he said. "You're a quick learner."

"That was fun," I said. Then I looked at my messy hands, and reached for his t-shirt, and started wiping. He laughed, and I told him the same thing he had told me yesterday. "Your cum, your shirt."

Then I added one more important thing. "We should do this again," I said.

"We will, he answered."

You can probably guess what happened after that. We roomed together for two years. Every night at bedtime, unless we had a girl, we'd either take care of ourselves or he'd take care of me or I'd take care of him. Sometimes, we'd do each other together. He taught me how to do it, and, if I can say so myself, I got pretty good at it. His pre-cum was a marvel.

He'd told me that it wasn't gay to jack off together, and he was right. Our relationship was nothing like romantic, and it never occurred to either of us to kiss or make out or even sleep in the same bed together. We both sometimes brought girls back to the room for normal straight masculine fun. We sometimes sucked on each other, just for variety, but hands worked better so we usually didn't do that. We had no interest in anal sex or anything related to assholes. We were friends, albeit with benefits, nothing more. Just like any two guys.

I wish I'd know years earlier about how nice it is to enjoy the simple, normal act of sexual pleasure with friends. Everybody should do it. I don't know why we all don't.

BTW: I forgot to tell you. His name was Dave.

And believe it or not, we both did get to see Julia's tits, for real. They were everything I'd hoped they would be. She and I got married after college. She still goes braless, and still likes to have her nipples poking through her shirt.

alan556
alan556
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5 Comments
roveroneroveroneover 1 year ago

Not sure what universe hj's/sucking cock/ not considered gay....

And while a 'healthy' fondness for having a tug don't recall every night for years-satyriasis- nor keeping a cum rag on bedside table-squicky

AnonymousAnonymousover 1 year ago

Quite a few believe that Helping out a friend isn't gay. It's just nice." and it is true,

AnonymousAnonymousover 1 year ago

When I started college, there was a big drought going on so we were supposed to save water. The first day, the dorm RA (a woman) gathered everybody together to give us dorm rules. One rule was. “Don’t flush pee.” Another was to keep showers to two minutes. We should “make arrangements with our roommate so we can masturbate in our rooms instead of the shower.” My roommate and I were too embarrassed so we didn’t do it. We did the wait till he’s asleep thing until we realized that we were both waiting for the other one to go to sleep. Then we just said fuck it, and decided to just do it whenever we wanted. We saw each other jacking hundreds of times over the year. Loved it. Everybody should do it.

AnonymousAnonymousover 1 year ago

Great story. I don’t understand why men are so embarrassed about masturbation. Who cares if somebody sees?

MCMaineNudistMCMaineNudistover 1 year ago

I liked this story. My brother and his best friend would wank each other and suck each other. And the best part was I got to watch. Thus began my love of watching guys playing with each other.

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