The Keys Pt. 01

When I was a teenager, my father had a sailboat. He'd been going through something of a midlife crisis and was sure that a sailboat would solve it. We would sail down into the Florida Keys almost every weekend with my Mother and Sister in tow. We would always have fun doing it, but a twenty-five foot sailboat gets cramped easily and with four people aboard, bickering always results.

My Mother enjoyed it, but would end up having to discipline my Sister and I, so it wasn't always fun and games for her. Finally, the weekend I turned eighteen, my Father decided it would just be he and I. The girls would stay home and do their thing and we boys would go out and do ours.

I was closer to my mother, but got along ok with my Dad. I was beginning to become a halfway decent sailor due to all the trips we had taken. My Dad started the small motor on the back, I untied the cleats and stowed the lines, and we pushed away from the dock, headed for the channel. The morning was already getting warm. The summer sun could heat up the day the moment it showed its face above the horizon. There was a faint sea breeze, but nearly no chop at all as we motored out into Biscayne Bay.

We were headed over to Pumpkin Cay, which was a small area of tiny islands down south, just an hour or two's sail from where we were. The motor was cut and sails unfurled. I tightened up the sheets, the mainsail and the jib snapped at the wind and the boat listed a few degrees to the side, beginning our trip. The mild breeze moved us along easily, and I lowered the keel deeper into the water as a stabilizer. My Dad told me to take the tiller, so I hopped into the stern and grabbed the long wooden handle, careful to set an angle to maximize the wind we had at our side.

My Father was darkly tanned from so many boat trips. I was getting there as well since I was nearly on every one of them. He stripped off his shirt, putting on his wide brimmed hat, and kicked off his top-siders. We chatted on route and changed positions occasionally. I liked sitting up front as we raced through the water, watching the reef below. The water was clear that day and you could see all the way down.

Eventually we found our way to the small islands and had a secluded spot picked out on the lee side of the wind. We let out the anchor and settled. The sails were rolled up and the only thing heard was the lapping of small waves against the hull. The water was only about 10 feet deep or so, and as clear as it was, it was like being in a pool. My Dad pulled out a beer and I dove into the water. I saw the bottom of the boat from underneath, which always unnerved me for some reason. After a few minutes, I climbed back aboard and went down into the galley to grab a sandwich. My Dad was sitting in the stern doing the same. We ate and talked about assorted things. It was nice. Usually these conversations were more forced.

After a few minutes I felt I had to pee, so I headed down into the cabin to the head, which was merely a small toilet. There were these slatted doors you could close for scant privacy, and I reached for them out of habit. My Dad said from outside, "You know, there are no girls here. You don't need to do that." So I just whipped it out and went into the toilet. Once I emerged from the cabin, he said, "You don't even need to use the head, Son. You've got a whole ocean right here." He then stood up, pulled his shorts down and started peeing over the side into the water. I looked around the area, but there were no boats or any sign of other people for miles. He held his penis in his hand while he shot his stream into the bay and it was quite long, especially from the perspective of someone in their late teens, but still growing. I never had measured mine, but knew people spoke about their dicks in inches. He was uncircumcised, which I hadn't ever realized before. I hadn't really seen it before, or if I had, I didn't remember. Out here all alone, there were many details one could focus on.

He shook his penis off and plopped it back in his shorts. He sat back down and asked, "How's the water?"

"Fine," I responded. "It's pretty warm."

He asked, "Have you ever skinny dipped?"

I said, "No." That was a lie. We had a pool at home that I swam naked in sometimes when no one was around.

"Oh, you should try it sometime. You just glide through the water. You'd be amazed at how much resistance you get swimming just from your bathing suit," he said. I knew exactly what he was talking about.

"Yeah, maybe," I said.

"You know what, I'm going to do it. What the hell. There's no one around here but us guys!" he said. At that, he stood, and pulled off his shorts. He had a tiny bit of a belly, but the rest of him was average. He had muscular legs, a broad chest, and his dark curly hair glistened with sweat from the heat of the day. He stepped over the rail and his cock now swung freely between his legs. There was a tuft of pubic hair at the base and his testicles bounced back and forth as he stepped. He then dove into the water and popped up.

"Why don't you try it?" he shouted.

"Well, alright!" I responded nervously. I stripped off my own shorts, again looking around and finding nothing. I jumped in and sliced through the water like a knife without the resistance of a bathing suit. We swam around and I was exhilarated at the feeling. I would plummet to the bottom, looking for crustaceans and fish and pop up to the surface over and over again. My Dad did the same, at one point, hopping back aboard the boat to grab some fins, masks and snorkels for us. He tossed them to me and I put them on in kind, which made swimming even easier. Looking down at myself with the mask made everything clearer. I noticed my smaller penis even smaller than usual because of the cool water. My dad still maintained his size as he cruised around the water looking around the bottom.

Eventually he got out of the water and lay out in the stern on one of the benches. I got out later and saw him asleep on his back with his had over his face. I lay down across from him. His dick was draped across his thigh and I noticed the thick foreskin covering the head completely. I was circumcised, so it was an anomaly for me. He appeared to be asleep, breathing deeply and slow, loudly though his mouth. I was curious about it, so I crept over near his sleeping body and stared at it. The sun shown on it and I saw how thick it was. I wondered what it felt like to have foreskin, and if my much smaller dick would grow to a similar size. It looked to be about half as long as his, but thin.

I had been leaning directly over his penis when suddenly I heard, "What on earth are you doing?" I fell over in shock and stammered, "Nothing!" I had no idea what to say.

He chuckled, "It's ok, Son. Were you just looking at me?"

I said, "Well, yeah. Sorry. I didn't mean to." I moved back to the other bench and looked away.

"It's ok to be curious about other peoples, um, equipment. Guys do it al the time. It's perfectly normal," he said, trying to reassure me. I remained mortified.

"No, I wasn't doing that. I was just kind of leaning over looking at the water," I said. That was easily the poorest excuse for a lie I had ever come up with.

My Dad laughed. "Oh, stop it. I know mine looks different than yours. Your Mom wanted you to be circumcised when you were born and I went along with it," he said. He sat up, leaning back against the railing. His dick loosely hung between his legs, and partially off the bench toward the floor. I was staring at it the whole time he spoke to me. "You know," he started, "I was about your size now when I was your age. It started growing a bit soon afterward."

I hardly had any hair on it, so my penis had a clean look to it whereas his had hair, and probably made it look even larger, I thought. Without hair, it must be enormous, I thought. We sat there across from each other, only feet away, me staring at his cock. It looked like it was swelling slightly. I looked away quickly, realizing he was looking at me staring at his cock. He shifted a little in his seat, leaning back a little more deliberately. His cock twitched against his thigh and was clearly getting bigger. Suddenly, I was aware of my own dick swelling, which it would do at the drop of a hat. Almost instantly it was fully erect, and I tried to turn to the side to hide it, pulling me knees up to my chest.

He stood, laughing under his breath, and his cock arced downward toward the floor. He bent backward, stretching his back and arms, allowing me a full view of his growing phallus. "So, what do we do, now?" he asked. The afternoon was waning, and the air was finally cooling down a little. As he spoke, he turned toward me, his cock pointing down at me. "You know, Son, you don't need to hide it. We're just two guys out here in the middle of the Keys with no one around. Nothing to be ashamed about. We all get erections sometimes, you know. Even your old man," he said.

"I know, but now you saw me staring at yours. You probably think I'm gay, or something." I looked down, ashamed.

"Of course not! I've looked at other guys' penises before, you know! All guys check each other out. It's perfectly normal. Hell, you staring at me was starting to me get one, too," he said.

I looked at him and said, "Really? If that happened at school, all the kids would laugh."

"Well, you're not at school now. We're just a couple guys hanging out on the boat. Nobody knows about this but us, right?"

"Yeah, I guess so," I said. I relaxed a little. The shame of what I had felt was now melting away, and my dick had shrunk down to its normal boy-size.

"Good," he said. "Hell, maybe we can get through the whole trip with no clothes on! Deal?" he asked. He held out his hand. I took it, smiling.

"Deal!" I said.

I jumped back in the water and swam around for a bit while it was cooling off. My Dad was grilling something on the little portable grill we had in the galley. I got out after a while and we had dinner. The stars were coming out and my Dad said, "Have you swam at night? It's great. A little scary, but it'll be fine tonight because the moon's full."

"Cool," I thought. We jumped in again, and it was another world down under water. It was a little spooky not being able to see much, but eventually we got back aboard. I crawled into the V-berth in the bow of the boat under the hatch and closed my eyes.

I woke and it was still dark. I didn't have a watch on, so I had no idea of the time. I had to pee, so I started walking to the back of the boat to go over the side. Then I saw my Dad sitting in the stern of the boat. He was sitting on one of the benches and had his eyes closed. I thought he might be sleeping like that, and then I saw his hand moving. It was dark, so my eyes were still adjusting to the low light. His hand was grasping his fully erect cock and was he jacking it back and forth, slowly. His dick was completely hard and glistening in the faint moonlight. I was shocked and hid in the shadows of the cabin while he masturbated. I was completely absorbed in watching my Father do what I did every night in my room. His cock was huge compared to anything I had ever seen. I remembered watching a porno that a friend had pilfered from his Dad and seeing their cocks nearly this size. Maybe it seemed bigger since it was live and in front of me. Either way, I was transfixed. I heard him softly moaning as he stroked himself. I realized that I was still naked and my dick got hard instantly. I touched my own erect penis as I watched and it felt like it would burst.

I heard him softly moaning, "Yeah, suck it. Mmmm, that's good. Suck that dick." It was just like I'd seen on the videos. Suddenly, the table I was resting my arm on as I crouched in the darkness shifted and I lost my balance. I stumbled a little, falling forward. I froze in fear, and looked up at my Dad. He was looking directly down at me in the cabin, hand still around his shining, erect penis. "Hey!" he said, "What are you doing down there?"

"Um, I was just getting some water," I said. I was completely mortified. He told me to come out of the cabin. "It's ok, Dad, I'm just a little thirsty, really," I said in protest. He again told me to come out. I slowly walked out into the stern of the boat, trying to not show him my front, as my small dick was pointing straight to the heavens.

"How long were you down there?" he asked. I told him I was only there for a second. Seeing through the lie, he spoke, "Were you watching me? It's ok if you were, I was just wondering why you would have been leaning up against the table when you know the water faucet is on the other side." My head fell, and I sat on the bench opposite him. My penis was shrinking rapidly in my shame of being caught. "Look, I don't know how to explain this any better, but like I said before, guys do this all the time, and are always curious about other guys. There is nothing to be ashamed of. I'm sure you do this all the time, am I right?" he asked. I shrugged my shoulders in response. "Ok, then. So don't worry about it. It looked like you were about to do the same thing down there, am I right?" he asked. He leaned back into the bench, one arm draped over the side rail of the boat, and the other hand slid over to where his cock lay. It had softened during his questioning of me and now as his hand slid over to it, it started to firm again. He stroked it lightly and his legs parted a little. I forgot the shame of being noticed, and now was staring at his hardening package and his hand lightly caressed its length. The head began to poke out of its sheath of foreskin and it would twitch ever few seconds as it began to swell. The sight made my own dick harden and it was fully erect in seconds again. I attempted to cover it, still not used to such obvious displays of nudity and brazenness.

"Yeah, I guess I was right. You're a teenage boy. You probably did this several times already today. I do it all the time, myself. I guess being naked all makes me feel a little freer. Don't you think, Son?" he asked.

"I guess so," I said, still staring hard at his cock. My hand started moving against my own cock involuntarily. It almost hurt it was so hard. My Dad's dick was hardening rapidly and in no time appeared to be fully erect. He stroked it slowly up and down. His testicles rested on the bench between his legs and bobbed in time with his hand's movements. My hand started stroking my own dick up and down as well. It felt incredible doing this out here in the middle of the ocean, knowing there was not a soul in miles.

"Yeah, that's it. That feels good. Stroke that thing. Get it good and hard," he said. I was losing any inhibitions I had previously to the act of masturbating with my Father. I was watching his cock intently, focused on every detail that I could make out in the low light. "Have you ever seen anyone else do this before?" he asked.

"Just on videos," I replied.

"Ah, pornos. They're not anything like the real thing. Why don't you come over here so you can see better," he said. He slid to the back corner of the bench, his back facing the stern, and lifted his right leg onto the bench, stretching it out. His left leg rested on the floor, exposing himself to me better. I got up and sat on the other end of the same bench in much the same position, facing him, and stroked my own cock slowly. I felt I could cum instantly, but I wanted this to last longer, so I kept my movements to a very slow meter. "What kind of movies have you watched, I'm curious?" he asked.

"Just some movies that Steve had at his Dad's house one day," he said.

"Ok. There are all kinds of movies out there. There's guys and girls, there are movies where it's just two girls doing things, movies where there are just girls doing things, and even ones where it's just guys. What kind do you like?" he pressed.

"I don't know, all kinds I guess," I said. I couldn't keep my eyes off his huge cock. I loved watching the thick, veiny foreskin slide back and forth over his glistening cock head underneath. I also liked how his balls bobbed up and down with each stroke of his large hand on the long shaft.

"Well, everyone finds a type that they like more than others. I have a few, too. I like the ones where the girls put their mouth on the guys right here," he said, motioning to his thick member. "They're called 'blowjob' videos. They really get me going when I'm in the mood to do what we're doing now. What did you like about the video you saw?" he asked.

"Well, I guess I liked that, too. There was a girl sucking a guy's you know, and she made him shoot," I said. I couldn't believe I had just said shoot in front of my Dad like that.

"Ok, so there was a girl sucking another guy's dick, and he shot his load on her face? Is that what happened?" he asked as he jerked his dick more deliberately.

"Yeah," I said. "Some of it got in her mouth, but mostly on her face."

"Mmm, that sounds great. It sounds like you're into the same thing I like watching. How big was his cock? Was it as big as mine?" he asked. I was trying to relax, but it was difficult. This conversation was exciting me in ways I could have never dreamed. I was completely absorbed in it. Here was my Dad talking to me about blowjobs and cocks and cum while we were jerking off together. As much as I wanted to cum however, I actually wanted to see him cum more. I was leaning forward a little more to get a better view of his fat dick, and I stopped jerking my own, lest I shoot before I wanted to. I knew what happened after you came. You didn't want to do it anymore, and I wanted this to last.

"I think yours was bigger, and he wasn't uncircumcised like you," I said, as I stared at him.

"Did you like watching his dick?" he asked.

"I guess so," I said, bashfully.

"C'mon, you can tell me. Did you like watching his cock get sucked?" he asked again.

"Yeah, it was cool," I said.

"Which one did you like better, his or mine? Be honest, now," he said. He seemed as focused on me as I was on his cock.

"I think I liked his because he didn't have any hair on it, but I like yours because it's bigger and you're not circumcised," I said. My young cock was straining hard against my belly as I leaned forward, watching him stroke.

"Here, let me move closer so you can see it better. You shouldn't strain your eyes. So, you like mine better, huh? Yours is pretty nice, too. What else do you like about it?" he asked. He had slid right up next to me, sitting sideways to me. He angled his hips slightly toward me. His knee touched mine as he leaned toward me. I was in rapture now. My hand was resting on my balls and I moved it back and forth slightly, watching his large hand move up and down on his shaft.

"I like how it's thick and how the foreskin moves back and forth on it, and how your balls bounce around when you move it," I said.

"Yeah, I like that too. What else did you like about the movie you saw? Did you like when he came in her mouth and on her face?" he asked. He was sighing loudly and pulling on his balls. His cock stretched upward and seemed to be pointing right at me as he tugged.

"Yeah. Steven didn't like it, but I liked when it went all on her face and in her mouth. There was a lot of it-a lot more than I make when I do it," I responded.

"Yeah, I love when someone lets me do that to them. I wish someone was sucking mine right now." He was watching me stare intently at his rod and then asked, "Have you ever touched another guy's penis?"

"No," I said, unable to look away.

"Would you like to touch mine?" he asked.

"Ok," I said unsurely. I moved my left hand slowly over toward him and touched his huge cock. With my hand on it, it even looked bigger. It was hot and slick at the top, but the skin was soft and moved a little as I moved my hand down the shaft, stopping at his pubic hair.