This site ROCKS
This happened about six months ago. My roommate from college and I had decided to do a road trip for a vacation. We figured the summer would be a good time to get away, and just enjoy some easy swimming/beach/dining time. Kevin and I have always enjoyed each other's company, and have always been honest with each other about almost everything.
We had begun by driving for about 10 hours, stopping in a small town just outside of Boston. What Kevin and I did not plan on was the influx of other vacationers, and we were only able to find one roadside motel with one room left. The clerk explained the room only had one double bed in it, one small sofa, and all the cots were in use. He also said motels pretty much keep in touch, and there was not another room in the area. Kevin and I talked, and decided since it was so late that we just take the room.
Now Kevin and I have roomed for three years, so there was not a lot of embarrassment, and certainly not much we haven't seen (or heard) between us, except for sleeping in the same bed or getting physical. (Although I had thought about it MANY times.) Kevin said the bed seemed kinda small, and said he would take the sofa. I said that since we both slept in our underwear, what was the difference, but Kevin seemed to get pretty freaked.
We went to bed about 1:00 AM, and I could hear Kevin was anything but comfortable. He tossed for about an hour and then asked if the bed offer was still open. I said sure, and Kevin joined me, but really kept his distance. He did ask if I could rub the knot out of his shoulder from the sofa, and I agreed. He laid on his stomach, (all in the dark) and I massaged it, straddling his back for about five minutes. (We had done this to each other on several occasions after working out, so it was no big deal.) Kevin had beautiful back and butt muscles, which were tight and filled up his briefs nicely. I was so horned up, though. He said that was much better, and I said that 'well, payback is a real bitch, and if you feel something strange in the night, don't worry, it's just me collecting payment.' We always joked around like that in the dorm.
A couple of minutes later, Kevin rolled over on his back, and I could feel him move closer. His shoulder touched mine, and his hand rested by my side, slipping into the leg of my briefs, and just ever so gently touched the hair on my leg which sent a shot of energy through me. I was immediately rock hard, and put my hand on the side of his abs. I slid it down a little further, and although I didn't actually feel his cock, I could tell he was hard now too. I suggested that since we had been through almost everything else together, that we could take care of this too, if he was willing. I told him that we should just face it and admit we had jerked off lots of times when we thought the other was 'asleep' knowing we were listening to each other jerk ourselves off, and how hot was that????
Kevin got nervous, said he was sorry, guessed this wasn't such a good idea after all, and he hoped he hadn't screwed up our friendship. I said 'no problem,' I understood, and still loved him like a brother. I was secretly disappointed that we had gotten so close and yet were so far away. I told him he shouldn't feel bad, and honestly, I had wondered too what it would be like to be with a guy, if nothing else but to give and get a handjob from another dude, and if he ever did want to try it with another guy, I would hope it would be with me. I told him I hoped he wouldn't think less of me for being honest. We rolled over away from each other, and tried to sleep. Probably half an hour or so later, Kevin asked if he could ask me something. He asked me if I thought we could just do it this one time to see what it would feel like, and to relieve the tension. I was elated, but played it cool, saying that it would only be as little or as much as he wanted to do.
With that, Kevin reached over, and put his hand on my abs, and started massaging them. Once again, I was immediately hard, and Kevin went a little lower, traced the outline of my cock through my briefs, and felt my nuts through the cloth. As he did that, I reached over to him and did the same. I felt some pre-cum leaking in the front of his shorts, and I could feel the head sticking out straight up from the waistband. He moaned, and said that felt soooooo good. I got up on my knees, and gently pulled his underwear off. There was only a small light from the clock radio, but I could see the outline of his beautiful dick on his tummy. Kevin reached up and pulled the waistband of my briefs down, revealing my member, and he began stroking it. I dropped my shorts to my knees, and begged him to keep it up. I continued to stroke his cock while he laid on his back as he kept moaning.
Kevin asked me if he was doing OK, too fast or too slow, and I told him he was perfect, just to do what he did to himself when he jerked off. Kevin kept this up, every once in a while feeling my tight nutsack, and then going back to masturbating me. I took this for about four minutes, and finally said I had to cum. Kevin kept up his stroke, and I shot three or four ropes of jiz all over his hand and his chest. All this time I was still stroking him while I was kneeling next to him.
After I finished, I laid down next to him. I went over on my left side so I could jerk him off with my right hand. I felt his hips, his inner legs, and back to his dick. He was so hot and hard, I thought he was going to explode. He started to buck his hips, and I could feel his dick start to twitch and swell up, just like mine, just a few strokes before an orgasm.
Kevin kept saying how good it felt, and to please keep it up. I told him that I wanted to feel his hot load all over us, and that whenever he was ready to give his excitement to me. Well, that seemed to put him over the edge, and he had his orgasm and shot his load. I had never cum that much in my life. Kevin let me continue to stroke him for another couple of seconds and said Man, that was the best of his life. I simply thanked him for letting me give him the pleasure, and for pleasing me.
We talked for a couple of minutes, and although initially embarrassed, said that this didn't have to screw up our friendship it we didn't let it. We agreed to look at it as simply two close friends expanding our lives, and getting even closer. Kevin and I cleaned up with a towel from the bathroom, and both rolled over in the same direction. Kevin put his arm around me, and asked if he could sleep like that.
I simply responded, 'Kevin.....we're friends, right............' and we both drifted off to sleep.