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Jerking with Jack Round 2

Posted by: Age: 18 Posted on: 11 comments
11 likes 9553 views Category: Masturbation Male-Male Tags: Friends, mutual, shaved, hotel
This is the second time I got to masturbate with Jack in a hotel room. I tried to cut out more of the boring parts for you this time.

This is a true story that happened just a few days ago. My relay team ended up making it to state track, so lucky me (and you). This meant my team got to stay in a hotel for three nights. Jack and I again decided to pair up. Now, for those of you that haven't read my previous story, Jack and I had a hotel room to ourselves, and we masturbated together. This time I prepared for the hotel room by not masturbating for five days before this. On the ride up to the hour and a half ride up to the hotel, the bumpy road gave me a hard on the whole way, so I know I needed to cum and bad. I was saving my self to try to cum as much as Jack can, but my plan went out the window as you'll see. The first night up there, all the others went out except for me and one senior girl from our track team. We stayed behind because we had both already eaten. Long story short, this girl, who will now be referred to as Katelyn, and I have been talking and we're beginning to really like each other. She is about five feet five inches tall and very tan. She is short and skinny, but had big D cup boobs and a nice shaved vagina. Katelyn is damn good looking. I'm getting off topic. Katelyn (who thought now was a great time to lose her virginity) and I had sex in her hotel room, and I shot my huge load of cum I was saving up on her instead of with Jack.It was Jack, a freshman, and I in our room. Jack and I didn't have our privacy we wanted at first. The next morning after my "fun time" with Katelyn, Jack and I woke up on separate beds. The freshman was on the floor. I'll call him Drake. Drake was the first one to get up, shower, and go down to breakfast. Once Drake left, Jack and I got up. He sat on the toilet to crap, and I started taking my clothes off too shower. I was getting a little hard standing in front of Jack with my hairless dick at the same level as his face. I got in and started washing my body. About five minutes later he got in the shower with me. I looked down and saw that he had shaved his dick. He said, "I thought you looked good shaven so I wanted to try". I said, "well it's working for you." We got that bathroom steaming. Both of our dicks and balls were sagging low. I was starting to get hard so I started stroking. I got rock hard and asked if Jack wants to jerk it. He said on the bed, so I got out and dried off with my raging hard on. I walked out of the bathroom followed by Jack drying off. I dropped my towel by my bag and stood naked as Jack walked out with a full hard on. His dick looked really good without hair. His balls were saggy as normal. His dick bounced with each step. He stopped next to me and I became rock solid. I asked,"Lets pre-race cum." He said,"Hell yea. We can relieve some stress now." We laid down on his bed and began stroking side by side. Our balls were bouncing with every tug. I reached over with my left hand and massaged his saggy balls. I love the feel of his soft shaven balls. He then reached over and started massaging my big hairless balls. He said,"heads up, I'm gonna cum." I said,"me too." we both clenched up and he began shooting his hot cum right before I did. I shot out three strands and then the rest dribbled out. I finished and saw that he was still cumming. There was almost a pool of cum on his chest. I got up and wiped off my cum. My dick was soft by now as I put on clothes. Jack was still there catching his breath. I walked over and began to milk the rest of the cum out of his cock. He eventually cleaned up and got dressed. Later that day we got back to the hotel. We we all sunburnt bad so we decided to go swim. Drake, Jack, and I were in the hotel room getting ready. I stripped naked right in front of the other two. Drake was staring blatantly. I wiggled my hips which whipped my cock from side to side and Drake and Jack laughed. I got my trunks on before Jack was naked. He whipped is cock around before he put his stuff on. Then we turned to Drake and said your turn. He hesitated then slowly took his clothes off. He finally pulled his underwear off to expose his hairy cock. He wiggled but it didn't move much. He got dressed real quick. We swam with the girls and Katelyn was really friendly. We played volleyball with a beach ball and the girls on our shoulders. I had Katelyn on my back. Just seeing her would have been enough to get me hard but having her sit on my shoulders get me really close. It was a constant struggle to stay soft until I got back to my room. Once we did get back to the room, Jack and I just stripped naked and jumped on the bed. Drake was in a different room. Jack said he wanted to try something new. He got up and walked over to me. He got on top of me and put his dick on mine. He stroked both ours together to get them hard. Once they were, he tried humping but it didn't work too well so he went back to stroking both. We were both rock solid by now. His balls were bouncing with mine as he stroked both our hairless cocks. I looked down at our evenly sized cocks. His red head was smashed with my purplish head when his hand reached the tops of our dicks. I was starting to get close and I could tell he was too. His breathing got much heavier as he stroked us faster. Jack then let out a loud grunt and shot his hot load of cum onto my stomach. Three sticky white strands shot out. He squeezed out the last few drops cum which landed on my cock. He rolled off of me and laid there catching his breath while his dick softened. I grabbed my cock and tried to use his cum as lube but there wasn't enough on there. Jack stayed next to me and watched me clench my butt cheeks and blow my load. Cum shot out and landed just short of his on my stomach. Jack then took a finger and wiped up some of his cum and ate it. He then did the same with mine. He shrugged and told me to try it. I tasted both our cum and couldn't tell the difference. Neither of us really liked it. I cleaned up and put on shorts while jack walked around naked. He eventually put on clothes to go to another room but he got naked as soon as he got back. We laid in my bed. I had on just shorts. Jack was naked. I laid on my side next to him and played with his dick and balls. His balls were shriveled up but I warmed them up and the went back to their saggy spots. I would stretch his balls out as far as they went then play with his semi hard cock that was laying on the shaved area. I did this until Drake came in at midnight. Jack just laid naked on my bed while Drake got ready for bed. Eventually we all went to bed. I took my shorts off to sleep. Next morning we all got up and jack and I roamed around naked the whole time. That night all three of us were in our room. I was flipping through the channels when I found and HBO channel with a hot naked chick on it. Needless to say we stopped there and watched. I was hard an I new Jack was. Drake stood up to go to the bathroom and I saw that his dick was making his shorts stick out. I said, "stop. You going in there to get rid of your hard on." he blushed bad. I said, "If you are gonna do it, you might as well do it with us." Jack got up and took his clothes off. His hard cock bounced out of his shorts. It looks really damn good without the hair. I followed suit and surprisingly enough, so did Drake without hesitation. We all laid on Jack's bed with Drake in the middle and me on his right side. Jack was on his left. Drake said, "wow. You guys have bigger dicks than I do." I said, "well yeah. We're older than you, so we are gonna have bigger dicks." Jack said, "yeah, my dick was the same size as yours when I was a freshman. It will get bigger don't worry." Then we all started stroking for real. Jack and I used our whole hand while Drake used two fingers and a thumb. After five minutes Drake came onto his stomach. There was one strand but it was a small strand. He caught his breath and then started stroking again. Jack and I looked at each other and shrugged. Five minutes later, Drake cums again. He shot one more small strand of cum. Then as his dick softened Jack shot his hot cum onto his chest. I followed soon behind. Having too people watch me cum really was exhilarating. I shot a normal sized load of cum onto my chest and stomach. Drake asked, "will I spurt as far as you guys do?" Jack said, "Maybe. It depends on the person. Logan doesn't normally shoot that far. We all showered together. We all masturbated four more times together. I can tell you I wasn't shooting much cum by the third or fourth time. Jack still managed to shoot a bigger load than me each time. The amount that kid can cum is ridiculous. I'm glad he can though because I love watching him cum. Especially since he shaved. Overall, it was a successful three nights. I had sex and jerked off a lot with Jack and a new freshman Drake. My dick has been soar ever since. I came for the first time since the last day writing this story. Thanks for reading. Feel free to ask me any questions. I'll try to answer them as best I can. I do want to ask what you guys think about shaving. What do you think looks better, a shaved dick or a hairy dick?

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