Cool College Hallmates 03 (Patreon)

Everyone is 18+ and fully consenting.

From the diary of Tommy, the clueless jock.

When Wes came back from break, our room was a pig sty. I had not been good about cleaning up, and I had dirty clothes, cum rags, all that crap just lying around in piles. I had spent so much time at the gym that I had no energy left when it came time to clean the dorm. Working out was the only thing that made sense to me, made me feel like I knew what I was doing, building my muscles bigger. All I had to do was move heavy things, eat food, and make sure my body was growing bigger. If I was hitting those things, then my life was going right. It didn’t matter that nothing at school made sense to me, or that I was always getting into awkward situations with other guys. 

When Wes came through the door, I was sitting around naked, and threw on some dirty underwear off the floor as quickly as I could. My dick was so big and awkward and always in the way, that I barely got it stuffed into my boxer briefs in time for him to walk in. He stopped and scanned the room, and I looked at his big muscles in his tight shirt, noticing he must have been hitting the gym over break as much as I did. I wondered for a moment which one of us would win in a fight, in case he got really mad about the mess. I braced for him to take a look at the mess and yell at me, or at least be mad at me or something, but it turned out he was actually really cool about it. 

He took a deep breath in through his nose, and said, “Damn, it smells rank in here.”

The weird thing is that he had a smile on his face when he said it. I guess he was just a really cool dude after all, and I never had to worry. 

I laid back on my bed, not worried about my bulge sticking out, as he dropped his bag and started cleaning up immediately. He started with my dirtiest clothes first, ‘cause he is just that nice. He started sniffing them one by one, I guess because he wanted to sort them by how dirty they were. He put the sweatiest and nastiest clothes over by his own bed. He kept commenting things like “Oh this one’s a keeper” and “Wow best one yet”. He’s always so funny when he jokes around like that.

I just scrolled through my phone while he cleaned up, but when he reached for that one pair of underwear that I had been using as a cum rag, including one big load of cum right before he got home, I tensed up, watching him out of the corner of my eye.

Luckily, he didn’t seem to notice it was cum. He just paused and looked at it for a second, then adjusted his pants, making himself more comfortable for whatever reason, and threw them onto his bed, next to his pillow. I almost wanted to say something, but didn’t want to make him feel weird for having my cum rag on his bed. I realized he must be putting the extra dirty stuff on his bed for when he does laundry later. He just didn’t want to forget it, and having the pile right next to his pillow would be his reminder.

“So,” he said just as he was finishing stacking up the laundry piles, “Derek says you gave him a good massage over break.”

I gulped, nervous to talk about that. 

“Yeah,” I said, but I couldn’t think of a way to change the subject. “I always practiced on my brother, so I know how to give a good massage.”

“Lemme get one,” he said, dropping his pants and taking off his shirt quickly, standing there in his underwear. 

The first thing I noticed was that he had a boner, but I didn’t want to point it out and make him feel weird about it, so I ignored it.

“I would,” I said, scratching the back of my neck, “But the thing is. Last time was kind of bad. I accidentally got my dick caught in his ass.”

Wes didn’t even look surprised. He just laid down on his bed, sticking his bubble butt up in the air. “Go ahead.”

I wasn’t sure if he heard me right, so I went on. “No, like, I accidentally poked him right in the ass, and it even went inside. It was so embarrassing.”

Wes still didn't react. Almost like he already knew? 

What a cool guy, I thought to myself, He’s not even upset about that.

So I walked over and started rubbing him down, staying in my underwear since it was just us guys here anyway. I leaned into him strongly, since he was another muscular dude like myself, and I knew he needed me to push hard on his muscles. His underwear was still on, so there was no issue with pressing into him. 

He interrupted after a minute. “Can you do my glutes?”

It took me a second to remember that means the butt.

“You sure?” I asked. 

“Yeah,” he said. 

I started over the underwear, but he took them off after a second without saying anything. I didn’t want to make him self conscious, so I didn’t say anything, just kept rubbing his cheeks. 

He pulled up his computer by his head, and casually opened it, switching to a tab he already had open, and playing some porn. My eyes opened wide. So that’s why he has a boner, I thought, he was just having a horny day.

I didn’t want to say anything and make it feel weird, so I just kept massaging him, trying to pay attention to what he needed from me.

“She’s hot right?” he said.

“Um.. yeah,” I said, feeling myself getting hard already in my underwear.

I did my best to keep my hard boner away from touching him, but I couldn’t avoid it completely, not if he wanted a good massage. I guess it was cool that he wasn’t shy about that. 

He suddenly reached into his bag, and pulled out some “massage oil”, throwing it back to me.

“Use this,” he said, closing his eyes and resting his head on his arms. 

I squirted it onto my hands, and this gooey, slimy stuff came out, not like I was used to. I read the bottle and it said “sexual lubricant” on it. 

“Huh,” I said, “I didn’t know you could use the same stuff for massages.”

“Depends what you’re massaging,” he said without opening his eyes. 

I shrugged, not really knowing what he meant. 

I just reached back down and dug into his glutes, and he said it felt good, but needed me to work him “closer to the center”.

I actually kind of enjoyed how the “massage oil” felt. It made it much easier to dig into his muscles exactly where I wanted to.

I tried to listen to him and get “closer to the center”, but wasn’t sure exactly what he meant. He just kept saying, “More.”

My thumbs went all the way to the little, pink ring of his actual asshole before he finally told me, “That’s the spot.”

He made me push harder, and I did my best, trying to work out whatever weird kink he must have had in that muscle, until I accidentally slipped a thumb inside him. I didn’t say anything, but I felt him tense up a bit. I was going to apologize, but I didn’t want to make it weird, so I just pretended it didn’t happen. When it happened again, he didn’t tense up as much as before, so I figured it was no big deal. 

I kept accidentally inserting my thumb over and over, since it was the only way to massage his glutes the way he wanted, until it felt like I was stuffing a turkey. With the porn playing, I started to have naughty thoughts, and I hated that I had my hands were on my friend while I was thinking about it, but still, It hit me that his ass looked like a girl’s ass. He didn’t have any hair on it, unlike most guys. And, he had a big, meaty roundness to his butt too.

He suddenly leaned back so his body was pushing up against me, and said, “Get my shoulders now.” 

“I can’t,” I said quickly, “You have to move so I can reach .”

“I wouldn’t be able to see the computer,” he replied after hesitating for a minute, “Just do it from there.”

“But I,” I started, but decided to just go along with it.

If he didn’t care, then I didn’t either. I had to take off my underwear so I didn’t get the massage oil/sex lube on them.

I did what he said, trying my best to keep my hips back and not touch him with my big, awkward boner. But it was the Derek accident all over again, and my annoying meat rod kept touching his ass. But still, he was cool and didn’t say anything about it.

“Get my neck,” he said, but then he stretched out, making it even harder to reach. 

I pressed against his hole on accident, and I heard him make a noise. It was like a pleasured grunt, but that didn’t make sense since I’m a guy. I realized he must have not have liked that, so I said, “Sorry.”

He just grunted again. I shifted to lean off of him, but he reached an arm back and held me in place. I guess he really liked the massage. He quietly put my hand back on his neck, pulling my arm. He was as strong as me, and he held me there tightly. His other hand reached back and held my hip. I began rubbing his neck again as he basically held me where he wanted me.

He must really need this massage, I thought, so I just focused on working out whatever kinks he had in his body, not worrying about where my dick was.

Then he leaned back into me, and with my big, stupid penis being hard from the porn, it slipped right between his big, perky mounds of “glutes”. It was so warm, soft, smooth, and wet with “massage oil”. With the porn playing, it felt like I was hooking up with a girl basically, as weird as that sounds. 

He didn’t seem to be bothered, because he kept holding me in place while he shifted his body around, rubbing against me on accident in the process. It was cool that he didn’t seem to be bothered too much. His back, his ass, his abdomen all tensed under my palms, but I guess it was just from the massage.

But then another bad accident happened. He shifted again, and I felt the hole between his glutes actually push onto my dick. 

“Not again,” I muttered out loud. “I’m sorry dude.”

“Sorry for what?” he asked, keeping his eyes closed, his hand on my hip, even though his face tensed up a bit.

I guess he doesn’t notice! I thought, How lucky and awesome.

He kept pushing back, making my dick go further inside him while I rubbed his neck and his shoulders. To be honest, it started to feel kind of good, in a sexual way. The porn playing was making me horny, and the wet heat of his insides was giving me my own massage, right on my dick. I didn’t want to like it, but it was hard not to.

He started grunting and groaning as my dick pushed further into him. I felt so bad about it, but I guess he was just loving the feeling in his shoulders and neck so much that he didn’t even notice what was going on in his ass.

“Right there,” he said as he started breathing fast, “That feels so good.”

I tried to shift to dig my thumbs deeper into his shoulder, but he stopped me. “No, don’t move, just keep doing what you’re doing.”

I smiled, knowing that I was making his shoulders feel good, and just dug my thumbs in hard. I was really working him, but he still kept asking me to go “harder”, and I couldn’t say no to a friend in need, even though my thumbs were getting sore. My whole body shifted forward and back as I worked all my muscles trying to work out the kinks in his neck and shoulders. Unfortunately, my dick kept going deeper inside him with every movement, but he still didn’t notice yet, thankfully.

I felt like an idiot. Why does my dick always end up in these awkward positions?

“Is this how you did it with Wes?” he asked, breathing hard, like it was hard for him to even talk.

“Yeah,” I said quickly, hoping he still didn’t realize my dick was in his ass. It was such good luck that he hadn’t noticed so far. I was terrified that he was going to realize and we would have an awkward moment.

At least he didn’t say anything about it. He must have been too wrapped up in the massage to care, if he even noticed. 

I kept working him until I noticed another problem was happening. The feeling on my dick was getting so good that I was actually about to finish. I thought he would notice that, so I did everything in my power to stop it, but the porn was playing, with girls taking dicks making guys cum. That’s my weakness, 

I tried to hold it back, but Wes shifted again, getting up on all fours and jerking his own big dick, holding my hip so I stayed where I was. I don’t think he realized that my dick was buried deep inside him, or else he would have freaked out. I guess he wanted to keep getting massaged even while he was busting a nut. Seemed weird to me, but I guess guys do that sometimes. 

Even though he wasn’t watching it, the porn must have gotten him super worked up, just like me. He was stroking himself hard, like he was going for a quick one. He leaned back and accidentally pushed himself completely onto my big, annoying dick. I guess he didn’t even notice, because he started cumming right then. I felt his ass tightening on my shaft rhythmically, and I started to cum too. My abs tensed and I leaned forward, my sweaty abs touching his back, both of us cumming together and shaking a bit. All thoughts left my brain, like they always do, and I wasn’t worried for a moment.

It was the weirdest orgasm of my life, but it was kind of cool doing that with a friend, especially if he wasn’t bothered by my dick touching him like that, and even poking inside his ass on accident.

He finally pulled away from me, collapsing onto the bed, his body falling away from my dick. It slipped out quickly, and he made a sort of moan in a weird way. I guess he got comfortable with my dick in his ass, even if he didn’t realize it was in there during the massage.

“That was so good,” he said, still catching his breath. 

“You must really like massages,” I said.

“You’re the best at them,” he said back, winking at me. 

I looked at the pile of cum between us that he had made. I didn’t want to point it out and make it awkward, but my own cum was leaking out of his ass, already dripping to his balls. Maybe if I didn’t say anything, he would just think it was his own cum that landed down there, and it wouldn’t be awkward.

His muscles must’ve felt good after that, because he flexed a few times as he wiped the sweat from his body and his ass.

He was such a cool friend. I was glad to have such a chill dude as a roommate.