One day, my friends Ray, Mike, Anthony, and I went sleigh riding on a huge hill near Ray's house. We recently had a snow storm that left about nine inches of perfect snow for sleigh riding on the ground. However we didn't know that we were going to end up going sleigh riding so none of us brought the right clothes for the occasion. We were all wearing sweat pants with our ski jackets, except for Ray because he had snow clothes at his house.
We rode down the hill for about an hour, until we all started to become cold and wet. Sweat pants did not keep any of the snow or water out. We decided that we would walk back to Ray's house now to warm up. However, none of us, except Ray again, had dry clothes to put on. So, when we got back to Ray's house, he told us that we should go in through the garage and take off our clothes in there, so we did not get our soaking wet clothes all over the house. We all explained to him that we didn't bring a change of clothes because we weren't planning on going sleigh riding. Ray told us that we could put our clothes in the dryer, meanwhile he would give us all a pair of dry boxers to wear while we were waiting. Ray was the smallest out of all of us so he couldn't really give us any other clothes to wear because they probably wouldn't fit.
Mike, Anthony, and I were somewhat muscular, bigger than Ray. Mike is asian, Anthony and I are white. Anthony has short brown hair, brown eyes. I have longer brown hair and brown eyes. All of us, besides Ray, about six feet tall.
We all began stripping our wet clothes in the garage until we got down to our boxers. Ray was perfectly dry underneath, wearing a pair of Christmas boxer-briefs, with his huge bulge showing. That was the advantage he had. He may have been the smallest, but his dick was the complete opposite. Mike, Ant, and I were soaked underneath. Mike had on a pair of white boxers that you could almost see through because they were wet. Ant had on a pair of green boxers that showed the outline of the tip of his dick. I had on a pair of gray boxer-briefs that showed my bulge clearly. We all stood there, waiting, freezing, while Ray went to get us a dry pair of boxers.
Ray finally came back with three pairs of boxer-briefs for us. Before Ray even made it down the stairs, we were already naked. We stood there, Ray still in his boxer-briefs, as he handed us the short boxer-briefs. I looked around me and saw Mike's three inch dick, not shaved in about two weeks. Ant and I, about the same size, four inches soft, both cleanly shaven. We put on the boxer-briefs, so now we all had a bulge showing. Ant asked Ray if his parents were home because he didn't want them to see his bulge. Mike and I agreed that would be kinda embarrassing. Ray told us that no one was home so we could come inside and go hang out in the basement while he took a shower.
We walked into the house, nice and warm, wearing nothing but short, American Eagle boxer-briefs. We headed down to the basement while Ray went upstairs to shower. We played xbox for a while, then, Anthony said we should play a prank on Ray. I asked him what he had in mind. He hesitantly said that we should all cum on Ray's boxers that we were wearing. I wasn't too sure about that, I thought it was kinda weird that he would bring that up. I looked over to see Anthony already sprouting a seven-inch boner, clearly visible in the boxer-briefs. I didn't say anything to him about it but I just looked over to Mike who was on the other side of me on the couch, and he just shrugged. I said to Ant that it would be weird jacking off together, since we have never done that before. (I always suspected Anthony of being bi.) Ant said who cares, we're all guys, and we just saw each other naked like 10 minutes ago anyway, plus, it would be funny to see him wear the boxers after we cum in them.
Ant decided just to do it anyway, so he stood up with a tent in his boxers. He walked away to the couch behind us and from what I could hear, pulled down the boxers and started to jack off. Mike looked at me a couple minutes later and said that maybe we should just do it, and slowly started to rub himself through the boxer-briefs. I finally agreed, since I hadn't jerked off in a while anyway. Mike and I simultaneously pulled down our boxers to our ankles. Mike's small, five-inch boner popped straight out. I was still soft, but starting to get hard. I am about the same size as Ant, so when I got a boner, it was about seven inches too. We both joined Ant on the other couch and jacked as hard as we could before Ray got out of the shower. Ant was the first to cum since he wad the first to start. He came the biggest load I have ever seen, all over his chest. I am not gay, but the thought of cumming made me cum. I dribbled all over my lap. Ant was leaned back on the couch, exhausted. I stood up just in time to see Mike shoot high, and it landed back down onto his lap. We quickly had to run upstairs to change back into our own, now dry clothes, before Ray got out of the shower. We were all still naked, covered in cum. We walked upstairs and over to the small laundry room and took our clothes out of the dryer. I took mine out first, but then, all of a sudden, we heard the front door open! The three of us piled into the laundry room and shut the door behind us. Ray's mom was home. The three of us were practically pressed up against each other, not to mention the fact that we were naked and still didn't clean the cum. Great. I told them both to shut up and get changed. We had to hurry so that Ray's mom wouldn't fling open the door to see three naked teen boys covered in cum in a room together.
We wiped ourselves off with Ray's boxers and threw them into the dirty laundry pile. We quickly changed back into our normal clothes and went back down into the basement. It was a close call. What was one of the most awkward moments of my life ended up being a great jacking session.