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I was on a road trip in university for an away game with my varsity team. I was supposed to share a hotel room with two of my teammates but one of them got injured in practice, so he was taken out of the lineup and didn't end up traveling with us. It was just my buddy and I with the hotel room to ourselves.
It was pretty late. Each of us sitting up in our bed. TSN highlights were on the TV. We were talking about how we needed to get up early in the morning for our matches, but both of us were so wired from the drive that we were having trouble falling asleep. So, we just kept talking and eventually landed on the topic of sex.
We exchanged some stories about our past fucks and admitted that it had been a while (a couple of months) since either of us had gotten laid. We both said we watch a ton of porn and jerk off constantly when we're not fucking. We had a few laughs talking about our porn preferences and some of the most fucked up videos we've dropped loads to, and then agreed we needed to crash so that we weren't zombies the next day.
We were laying in our respective beds, lights off, and both on our phones. I heard some pretty consistent movement under my teammate's covers but didn't say anything at first. Then I heard a faint moan.
I said, "Dude, are you honestly jerking right now?" He burst out laughing and said that our chat had gotten him pretty horny and cumming would be the only way for him to fall asleep.
He asked, "Do you care?" I assured him I didn't give a shit as long as he didn't mind me jerking, too. He said he'd totally be fine with it, so I started tugging on my dick under the covers. Then I asked him what he was stroking to.
He said, "Just come watch it over here if you're gonna fap. It'll be easier to see." I was nervous and excited. I was always open to the idea of stroking with one of my buddies, but never knew how to approach the situation. My dick got even more hard when he asked me to join him.
I went to his bed, sat beside him, and started tugging under my boxers. We were watching a college girl get spitroasted by two fit guys. After a couple minutes of us commenting on the video, I said, "It's kind of weird jerking in our boxers. I feel like we're kids."
We both laughed and figured since we'd seen each other naked in the showers so many times, there was no point in wearing boxers, so we both ditched them. It was still dark but I could see my friend's dick from the light on his phone. He was packing, too. We jerked naked for another few minutes until we were both ready to cum.
We agreed to coordinate our loads so that we would both cum on our stomachs at the same time when the guys in the video finished. We both sped up our pace and let out a few big moans as we shot our loads. I couldn't see all his cum, but I heard it land on his stomach. It sounded so thick.
We didn't have any tissues around, so I just grabbed a towel from my bag beside the bed and wiped myself down quickly. I noticed that my buddy hadn't moved yet so I gave him the towel and he used the same one. We both remarked how good that felt, put our boxers back on, and said how fucked we'd be for the morning matches.
We're still friends to this day and ended up jerking a few more times throughout university. It was a great first experience jerking off with a teammate. Now I do it fairly regularly and have gotten much more into double teaming and gangbanging girls with my buddies!
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