My friend Tim and I are both 18 and we've been best friends since first grade. We graduated high school this year. We've always been open with each other about sex and we talked about masturbating, and about what we did with our girlfriends, but we never did anything together. If we needed to jackoff when we were together we'd excused ourselves, go into the bathroom and do it alone. Ever since a middle school trip we both have enjoyed amusement parks and especially roller coasters. There's a big park about an hour away from home and we've gone there many times. A couple states away from us, there's another park that has a reputation for the most awesome coasters and we wanted to go there for a long time. We asked our parents if it would be okay for us to take a trip there together after graduation and they said that would be a great gift so they paid for the whole thing. We planned to spend three days at the park. A week or two after graduation we packed up the car and headed to the amusement park. It took us most of the day to get there but we were all set for the next day's adventure.
The first day was awesome and we rode all the coasters at least twice, plus a lot of other rides. When we got to the hotel at the end of the day, we were really sore from all the walking, standing, and bumpy rides. Tim stripped down to his boxers and laid down on his bed and I did the same on mine. Tim said 'I am so sore I can hardly move.' 'Me too' I said 'it's too bad we don't have a trainer here who could massage away the aches.' Then it dawned on me that we could do that for each other so I offered. Tim was more than willing. So I got up off my bed and sat on the edge of his bed and started giving him a rough kind of massage on his back and his legs and he said it really felt great. His head was turned away from me and I was glad because doing this was giving me a boner and I was embarrassed by it. Tim said the massage was really helping the aches to go away. After about ten minutes I jumped over to my bed quickly so he wouldn't see my boner and I laid down. 'My turn' I said. So he came over and did the same to me. I turned my head away from him just in case he got hard too. I guess I was afraid of either of us being embarrassed.
When he was done he went back and laid down on his bed. My boner had only gotten worse while Tim was massaging me and so I went into the bathroom to take care of business. After I got out, Tim went into the bathroom after me and was in there for awhile too.
The next morning when we were into our second day of coaster riding, while we were standing in line talking Tim mentioned that he wasn't sore at all that day, that the massage really helped. I agreed. Then he said 'I noticed we both took awhile in the bathroom afterwards. Did the massage do the same thing to you that it did to me?' I smiled and said 'I guess it did because I really had to take care of business quick and that was pretty awesome too.' He answered 'Yah, I really had a wet one last night and a pretty awesome jackoff.'
That night back at the hotel it started out pretty much the same. After laying on our beds for a few minutes I asked Tim if he wanted another massage and he said 'yes'. So I gave him one and, as I expected, I got hard. This time Tim was facing in my direction and probably could see what it was doing to me but I didn't care now since I presumed the same was happening to him. After I finished the rough massage I started doing it more gently all over his back and legs. I even put my fingers up the backside of his shorts and sort of massaged his butt cheeks and while I was rubbing his back I reached beneath the band of his boxers and did the same from the top. Finally I asked Tim if I should just take those off him and he said 'yes'. So I pulled his boxers all the way off him and he was lying there completely naked. I kept massaging him lightly and slowly all over and he spread his legs a little. I started going way up the inside of his legs and I could see and touch his balls. He spread his legs even further apart when I did that so I guessed he didn't mind. After few minutes he surprised me by turning over completely and I saw his huge boner. 'I don't care what you do now' he said 'knock yourself out.' So I began massaging him all over including his boner. In a few minutes was starting to get wet with precum so I put some spit in my fingers and stroked his dick up and down. His breathing got more intense and in a few minutes he said he was going to cum. Jizz shot straight up from him in several massive ropes and he was moaning with an intense orgasm. When he finally stopped cumming I went and got a towel and cleaned him off.
With a great big smile on his face he said 'your turn' and so I got on my bed and he did pretty much the same to me starting with the face down and him taking off my boxers and then me turning over. When I came, it was just as awesome as his. We went to bed but several hours later I woke up and went to the bathroom and Tim must have woke up because he went right after me. When he got back to bed he said 'are you still awake?' and I said 'yes'. 'I could really go for another round like before' he said and I replied 'me too!' So he took off his boxers and sat on the edge of my bed and took off my boxers and went right to it. This time I didn't wait very long before I turned around and when it was his turn, neither did he. This time was as incredible as the first.
Our last night at the park turned out as great as the night before. We got together at our houses during the summer since that trip and have had plenty more jackoff sessions.