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.
