"I can't believe I lost the bet" I told Ron. Oh, by the way, my name is John. I'm 17, about 5'8" tall, I have an average build and am average looking and am a Senior in high school. My Best Friend Ron is also 17, he is 6'1" tall and looks like Leonardo DiCaprio, the girls go nuts over him, although he's never had a steady girlfriend.
"A bet's a bet John" he replied.
"Isn't this, well, a little Gay?" I responded.
"No, and if you thought so, why'd you bet in the first place?" he asked.
"Dunno. I guess I didn't think I'd lose and I didn't think if I did you'd make me do it" I responded.
"Well, you thought wrong, so get to it!" he said.
"Okay fine." I answered.
Although we'd been friends for about a year, this was the first time he stayed at my house. My parents had gone on vacation and said I could have a friend stay over as long as we didn't have a party. I thought it would be cool to ask Ron to stay since we could play games, go swimming, and just goof off. The bet had been his idea; whoever lost would have to give the winner a full body massage.
I watched nervously as he started to take off his clothes.
"Hey, you don't get to stay clothed you know. I'm not stripping down if you don't; besides I'll probably fall asleep as you're giving me a rub down so you may as well get ready to go to bed as well." He said.
"Okay fine." I replied even more nervous than before. I didn't think I was gay, but watching him take off his clothes was making me feel slightly aroused. I'd never felt this way getting undressed in front of the other guys in Gym class.
When Ron took off his pants I was surprised to see him in a pair of white Hanes briefs. I thought I was one of the few guys left my age that still wore briefs. My heart started to beat faster as looked at him. He was really nicely built. Not muscle bound, more around what a swimmers build is. He looked really good in white briefs which is probably why he wore them. He also had a moderately impressive looking package. It seemed to be about average sized.
"Okay, lay down on the bed." I said pointing to my waterbed.
"This is cool", he said, "I've never slept on a waterbed before."
"I've had it for a while. It's great in the winter when it's cold. Getting into a warm bed I mean."
"Yeah, my Dad won't let me have one." He replied.
He lay down on the bed on his stomach and I straddled him sitting on his butt and started rubbing his shoulders with the massage oil. After a few minutes I worked my way down his body rubbing his upper, then lower back. I moved down so that I was straddling his feet and rubbed the large muscles of his upper legs and calves. It also surprised me that my gaze was drawn between his slightly parted legs to the bulge of his balls. I "accidentally" brushed up against them as I rubbed his inner thigh further surprising myself.
"Okay", I said, "I'm all done.
"No, you're only half done", he replied sleepily, "You still have to do the front.
"Whoa," I said, "No one said anything about the front. Where am I supposed to sit?"
"Same as on the back." he answered.
"I'm not sitting on your dick!" I said indignantly.
"No one said you had to sit, just straddle me and get to work" he answered testily.
"Okay fine." I said.
As he rolled over, I couldn't help but notice that the arrangement of his package was substantially different then when he lay down initially. His dick was now going up to the left instead of lying over his balls. His eyes were closed and as I looked at him my heart started racing. He really was a good looking guy and his body was awesome. I had never felt this way about another guy before and it was really freaking me out.
I straddled him again while trying to control my body's response to my excitement. As I rubbed his shoulders and upper chest I could feel his dick periodically touching my ass. As I slid down his legs to rub his stomach and upper legs, I noticed his dick looked to be completely hard. It seemed to have a pretty extreme bend to the left. I wondered if that was just because of the way it was positioned or if it really did have that extreme of a curve. Then I realized I was staring at the outline of my Best Friend's dick through his tighty whities and decided I had better just finish the massage and go to sleep.
"Okay Ron, that's it. Time for bed." I said quickly.
"Excellent job John. I'll have to win this type of bet with you more often." he muttered more sleepily.
I turned the lights out and got into bed. At this point, I let my dick get as hard as it wanted since Ron wouldn't be able to tell. It took awhile but I finally fell asleep.
I woke to what couldn't have been more than a little bit later. I was lying on my left side facing Ron. We were in a spooned position with my arm over the top of him and my hand on his stomach. I was groggy and confused (and a little surprised that he hadn't woken up and pushed me off of him) and was trying to figure out what had woken me up. I could feel Ron's heart beating very fast like he was nervous or scared. At first I thought he was having a nightmare and almost shook him to wake him up when I realized he was slowly moving his body up the bed toward the headboard. My hand was staying in place and since he was moving was now on his lower stomach.
I pretended to still be asleep to see what he was doing. I felt my hand moving lower on his body as he pushed his stomach out. I couldn't believe it. Here was my best friend maneuvering his body in such a way that my hand was being guided closer and closer to his dick. After having given him a massage, and having a raging hard-on myself, I let my hand be guided down his body. The feeling of the waistband of his briefs on my hand was strangely erotic. That feeling intensified as I felt the soft fabric under my fingers. When my fingertips finally brushed up against his dick, I couldn't help myself and closed my hand around it. The feeling of the soft cotton wrapped around his stiff cock nearly caused me to blow my load. I'm sure Ron thought that it was an involuntary reaction because he didn't say anything.
We lay that way for at least 5 minutes. I couldn't believe how great it was to hold another guys cock. I had jerked off often enough, but it was a totally different experience to have another guy's hard dick in your hand. After about 5 minutes, Ron began turning onto his back pushing me onto mine in the process. My right hand was still firmly attached to his dick. He very slowly put his hand on my stomach toward the left hand side and slowly slid his hand down toward the waistband of my briefs. I didn't want to give away that I was awake so I concentrated on controlling my heart so that its accelerated beating wouldn't alert him. He carefully slid his fingers under the waistband and into my underwear. Since I had never had sex with anyone and no one had ever touched my dick but me, it was all I could do not to start hyperventilating. As his hand slid into my briefs he missed my dick by about two inches to the left. It was then I realized two things, I was still holding his dick and it did have a pretty pronounced curve to the left which I hadn't noticed until just then. The second thing was that I must either be the first guy he had tried this with or he'd tried it with another guy that had a similar curve since he obviously thought all dicks were curved like his.
After a few seconds, I could feel his hand travel to the right were he finally intersected my very hard dick. I felt him run his index finger from the tip of my dick to the base; I figure he was trying to get a feel for how big I was. He then opened his hand and took both my nuts in them. Although my dick is about average sized, I have a pretty good sized set of nuts. They are each about the size of a large egg. I heard a small gasp come out of him as he felt how large they were. He then went back and grabbed my dick in his fist similarly to the way I had his. We stayed this way for about another five minutes. He finally let go and got out of bed going to the bathroom. I rolled over onto my other side and listened. He was in there for a couple of minutes came back and fell asleep. I'm guessing he went in there to jerk off, so I just went back to sleep.
If you'd like to hear how things progressed the next night.