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First time on the Island

by JL


My first real sexual experience came when I was fifteen (I'm twenty now). We were spending a couple of weeks that summer at a lake in the mountains where my dad's company had a timeshare. Being an only child, I hadn't been looking forward to going and leaving my friends, especially when I found out that there were only four other cabins in the village and that they were mostly owned by older people with no kids. I had been curious about sex since I was about nine and felt some strange tingling when my best friend had slept over and we ended up curled up together in my bed. I had no idea at the time what that meant, but I wanted more of it. He obviously felt the same way and we spent a lot of time in my room wrestling and grabbing at each others crotch. Whenever we got together alone we would make that a part of our play and gradually came to be more comfortable with it. Over the next year, we graduated to flashing each other and giving glimpses of our little erections. He moved away soon after and we never did anything beyond basic groping. My sex education was at first gathered primarily by word of mouth from stories and jokes told by adolescents since time immemorial. I started masturbating when I was twelve and at my peak was up to four times a day. While most of my friends talked about this or that girl and claimed to fantasize over pilfered Playboys, I was much more aroused by thoughts of some male TV stars and models and even occasionally by some of those friends who used to pass around the centerfolds. Being bookish by nature, I hunting through a used bookshop during that winter and ran across a copy of a gay sex manual. I couldn't believe what I saw in the pictures and read in the text, and returned to that bookshop many times to read a few more pages while nervously keeping an eye out for the clerk. These sessions provided lots of material for my fantasies and also gave me at least a working knowledge of the mechanics of what I had been yearning for. We had been at the lake for about two days and I was already bored out of my mind - my parents had a whole program of sightseeing they wanted to do that didn't interest me a whit and I was facing two weeks of watching the three TV stations available there and reading the ten books I had brought. As I sat on the porch looking out over the green, I noticed a boy about my age idly kicking stones by the side of one of the other cabins. I watched for a while as he went about his task and soon noticed that I was horny. While this was a fairly constant state for me at the time, I realized that I was wondering what he looked like naked. I decided that I wanted to get to know him. I went outside (after gathering myself a bit) and asked him what his name was. We ended up having a long conversation. Steve was there with his grandparents for the summer. It turned out that he was almost fifteen, was starting high school that fall, had a little sister who was with him and a brother at college and was as bored as I was. He was a little shorter than I was (at the time, I was about 5'10), solidly built and very blond. What he was mainly into at home was boating, but there wasn't a lot of that at this lake, other than canoeing and a little sailing. His grandparents had a small sailboat at their dock and he asked me if I wanted to go out in it the next day. I said sure, that my parents were planning to be out all day and that I'd love something to do. My parents were delighted that I'd found someone my own age to hang out with and, after a quick call to his grandparents, gave permission for me to go. I had never been on a boat in my life and was really looking forward to it, but what occupied most of my thoughts as I drifted off to sleep that night was Steve. The next day was sunny and, after a quick breakfast, I went out to meet my new friend at the dock. He was already getting the boat ready. "Are you up for going out to the island?" he asked. I hadn't even noticed there was an island out there, but a quick glance showed that there was. "Sure. What's to do out there?" "Not much. But we can go explore a little." As he made the final adjustments to the mast and rigging, I looked at Steve closely. He was barefoot and wearing a nylon bathing suit, a grey t-shirt, a NY baseball cap and a black wristwatch. While thin, he was muscular and well defined for his age. He went through the motions of preparing the boat effortlessly and efficiently. He motioned for me to get on board. "Let's get started." As I climbed onto the deck of the small sailboat, I found myself really looking forward to getting out to the island. I wasn't sure where I wanted this to go, but I was willing to keep the options open. As the boat drifted across the lake, Steve began telling me about how bored he was this summer and how concerned he was about his parents, who had been having a lot of trouble lately. They had just moved that winter and he didn't have many friends where they lived now. I found something incredibly appealing about this guy - he was nice, cute and seemed a lot more sensitive than my friends back home. We beached the boat on a sandy stretch, secured it and walked inland a little. "Let's go over here," he said, "there's a neat little meadow beyond those trees." We walked a little way and found the grassy patch he was talking about. He pointed out some nests and rock formations that proved that he had spent some time here. "I come out here a lot - it's peaceful and I can get away from my sister." As I walked behind him, I couldn't help but to continue some of the fantasies I had developed about him the night before. I had never had such strong feelings for a guy before, and being alone with him on a relatively remote spot was fueling my desire. "Doesn't anyone live out here?" I asked. "No, it's too small, but there's a broken-down foundation on the other side, so there must have been some kind of house here at one time." We flopped down in the grass and stared up at the sky for a bit. I told him the pretty boring story of how I ended up there that summer and he grunted some sympathy. After another short pause, he told me about his brother, who was a college student but was right now visiting some friends in another state. Another pause - I was beginning to wonder if he was just a silent type or if he was uncomfortable. He seemed consciously to avoid looking at me. I rolled over onto my stomach and looked at him. I found myself staring at his wristwatch. It was a huge divers-style watch he had strapped loosely on his right wrist. I hadn't really noticed it until we laid down there so close to each other. He finally looked in my direction and saw my fascination. "It's my big brother's. Mine's busted and he didn't take this one with him. It's really too big, but I've always kinda liked it." I had no idea why, but there was something really attractive about him wearing it. "It's cool," I said, "I never wear mine." I had a computer watch that wasn't waterproof and anyway made me look pretty geeky. "I need one like this when I do races back home." He turned over slightly (I was laying to his right) and moved his arm so I could get a better look. I was still interested in seeing his watch, but when he turned I noticed the outline of a pretty developed hard-on through his bathing suit. I was in pretty much the same state, but being on my stomach it wasn't noticeable. I decided to show my hand, too. I rolled over to face him. "Looks like we have the same problem." He blushed furiously and looked back at the sky, but didn't retreat. I had to go on. "How often do you do it?" I asked. He tried to look down, but then turned his head away. "A couple of times a day." "Me too," I said. "Have you done it today?" He looked back at me, "No." I had, but I didn't think it necessary to mention it. "Looks like we both need to now," I said. He nodded his head. Wordlessly, we both pulled off our suits and shirts and surveyed each other's equipment. Except seeing my friend's when we were nine or ten, to that point I had only seen my own and those line drawings in the sex manual. I was kind of surprised at how small his was. He had about 51/2 inches with very little hair. On the other hand, mine, as I was beginning to realize, was pretty impressive. I had measured it at the beginning of the summer and found that it was about 8 inches fully erect with a lot of hair around it. He seemed pretty amazed and couldn't take his eyes away. "Go ahead," I said, "touch it." He gingerly reached over to my dick and stroked it with two fingers. "Take more of it." He then moved in a little closer and took the whole thing in his hand. Slowly at first he began to pump it a little and then more rapidly. I started heating up and began breathing faster and faster as his motion increased. Within a few seconds of having the incredible sensation of this cute guy fondling me, I exploded and blew my load all over his chest and hand. As I calmed down, he started rubbing his own and popped in about ten seconds, covering me. We both lay next to each other, recovering and gradually returning to normal breathing. I looked at him. "That was intense," he said with a grin. "Have you ever jerked off with another guy?" I asked. "No." "Me neither." While I was saying this, he took off his watch (I had covered that, too) and wiped it off on the grass. I idly reached over, taking it from him and slipped it on. The feeling of it around my wrist made me start to get hot and my tool started rising again. He saw, and his began getting hard, too. "What did you do to get your dink that big?" he asked. "Nothing - it just came that way from the factory," I said. "I wish mine were that size," he said. I smiled. "Just keep practicing." His hand moved down to start massaging his penis again. I decided to take another chance and moved in closer to him. I put my arms around him and rolled on top, so our cocks were rubbing each other between our bellies. This started felt incredibly good - I could feel him getting really turned on as well and we both started rubbing back and forth, faster and faster. I could feel the moment of truth coming quickly and backed off a little. He didn't, though and threw his arms around my neck, locking me in a bear-hug while cooing a little in my ear. Within a couple of more seconds, he let go again, covering me with a little less this time. As he relaxed in my arms, I instinctively put my lips against his and kissed him while I continued rubbing and pretty soon let go again . I continued kissing and was kind of relieved that he didn't recoil. Neither one of us knew that the tongue could be involved in such a proceeding, so we just dry-kissed for a minute. After we rested up a little bit, we both walked down to the water and rinsed off. While in the water, we embraced and kissed again. Back on the shore, we dried off with our t-shirts and got dressed. I gave him back his watch and we went down to the boat and went home. We didn't talk much on the return trip, but exchanged a few glances, each of which ended in grins, so I knew he wasn't horrified at what had just happened. I certainly wasn't, and was beginning to look forward to spending a lot of time together over the next week and a half. To be continued (maybe) . . .

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1 Gay Erotic Stories from JL

First time on the Island

My first real sexual experience came when I was fifteen (I'm twenty now). We were spending a couple of weeks that summer at a lake in the mountains where my dad's company had a timeshare. Being an only child, I hadn't been looking forward to going and leaving my friends, especially when I found out that there were only four other cabins in the village and that they were mostly

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